EP1680407A1 - Isopentyl carboxanilides for combating undesired micro-organisms - Google Patents

Isopentyl carboxanilides for combating undesired micro-organisms

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Publication number
EP1680407A1
EP1680407A1 EP04790302A EP04790302A EP1680407A1 EP 1680407 A1 EP1680407 A1 EP 1680407A1 EP 04790302 A EP04790302 A EP 04790302A EP 04790302 A EP04790302 A EP 04790302A EP 1680407 A1 EP1680407 A1 EP 1680407A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
chlorine
fluorine
haloalkyl
halogen
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Withdrawn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
EP04790302A
Other languages
German (de)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico GREUL
Benoit Hartmann
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
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 Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Priority claimed from DE10352067A external-priority patent/DE10352067A1/en
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1680407A1 publication Critical patent/EP1680407A1/en
Withdrawn legal-status Critical Current

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    • 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
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07C211/46—Aniline
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    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • 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
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

  • the present invention relates to new isopentylcarboxanilides, several processes for their preparation and their use for controlling unwanted microorganisms.
  • R 1 for hydrogen, CC 8 alkyl, C 1 -CVAl ylsulfinyl, dC 6 arylsulfonyl, C 1 -C 4 Alkoxy-C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl; C, -C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulf ⁇ nyl, C ⁇ -C4-haloalkylsulfonyl, halo-C ⁇ -C4-alkoxy-C ⁇ -C alkyl, C 3 -C 8- halo-cycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-C ⁇ -C 3 - alkyl, (CC 3 )
  • R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl
  • R 3 is hydrogen, halogen, C ⁇ -C8 alkyl, CC is 8 haloalkyl, R 4 is hydrogen, C r C 8 alkyl, CC 8 alkoxy, C r C 4 alkoxy-C, -C 4 - alkyl, C 3 -C 8 cycloalkyl; C r C 6 haloalkyl, C 1 -C 6 haloalkoxy, halogen ⁇ alkoxy-Ci-Gi-alkyl, C 3 -C 8 halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 5 and R 6 each independently are hydrogen, C 8 -alkyl, C 4 -alkoxy-C ⁇ -C 4 alkyl, C 3 -C 8 cycloalkyl; -Cs-haloalkyl, halo -CC 4 -alkoxy-C r C 4 -alkyl, C 3 -C 8 -halo-cycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 5 and R 6 together with the nitrogen atom to which they are attached, form a saturated heterocycle with 5 to 8 ring atoms which is optionally mono- or polysubstituted, identically or differently, by halogen or CC 4 -alkyl, the heterocycle 1 or 2 more may contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
  • R 7 and R 8 independently of one another for hydrogen, -CC 8 alkyl, C 3 -C 8 cycloalkyl; Q-Cs-haloalkyl, C 3 -C 8 -halogenocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 7 and R 8 together with the nitrogen atom to which they are attached form an optionally mono- or polysubstituted, identical or different, halogen or CC 4 alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, the heterocycle 1 or 2 more may contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
  • R 9 represents hydrogen or C r C 5 alkyl
  • (AI) is in which R 10 for hydrogen, hydroxy, formyl, cyano, halogen, nitro, CC 4 alkyl, CC 4 alkoxy, C r C 4 alkylthio, C 3 -C 6 cycloalkyl, C] -C 4 haloalkyl, -Q -Halogenalk- oxy or -CC 4 -haloalkylthio, each with 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl -CC-C 4 alkyl, R 11 represents hydrogen, halogen, cyano, C, -C 4 alkyl, - alkoxy , C 1 -C 4 alkylthio, - C 4 haloalkyl or CC 4 haloalkylthio, each with 1 to 5 halogen atoms, and R 12 for hydrogen, C, -C 4 alkyl, hydroxy-C C 4 alkyl, C 2 -C 6 alkenyl, C
  • A represents the rest of the formula (A2), in which 4 alkyl or C 4 -Halo-, R 13 and R 14 are independently hydrogen, halogen, CC genalkyl having 1 to 5 halogen atoms and R 15 represents halogen, cyano or C 4 -alkyl, or C ⁇ -C 4 haloalkyl or C 1 -C 4 -alkoxy, each with 1 to 5 halogen atoms, or
  • A stands for the rest of the formula (A3) (A3), in which R 16 and R 17 independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 haloalkyl having 1 to 5 halogen atoms and R 18 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 Haloalkyl having 1 to 5 halogen atoms, or A for the rest of the formula (A4)
  • (A4) is in which R 19 is hydrogen, halogen, hydroxy, cyano, -C ö -alkyl, C haloalkyl, CC 4 - represents halogenoalkoxy or C ⁇ -C4-haloalkylthio having in each case 1 to 5 halogen atoms, or A is the radical of the formula ( A5)
  • R represents CC alkyl or -CC 4 haloalkyl having 1 to 5 halogen atoms, or
  • R 24 and R 25 independently of one another are hydrogen, halogen, amino, CC 4 -alkyl or - C 4 -haloalkyl having 1 to 5 halogen atoms and R 26 is hydrogen, C r C 4 -alkyl or CC 4 -haloalkyl with 1 to 5 halogen atoms, with the proviso that R 24 and R 26 do not simultaneously stand for methyl if R 25 stands for hydrogen, or A for the rest of the formula (A 10) (A10) stands in which R 27 and R 28 independently represent hydrogen, halogen, amino, nitro, -GrAlkyl or CC 4 haloalkyl with 1 to 5 halogen atoms and R 29 for halogen, C r C 4 alkyl or CC 4 haloalkyl with 1 to 5 Halogen atoms, or
  • A stands for the rest of the formula (A1) (All), in which R 30 represents hydrogen, halogen, amino, CC 4 alkyl armno, di (C 1 -C 4 alkyl) amino, cyano, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl having 1 to 5 halogen atoms and R 31 represents halogen , Hydroxy, dQ-alkyl, Q- alkoxy, C 3 -C 6 cycloalkyl, -C 4 - haloalkyl or -C-C 4 haloalkoxy, each with 1 to 5 halogen atoms, with the proviso that R 31 is not trifluoromethyl , Difluoromethyl or methyl when R 3 is hydrogen and R 30 is methyl, or A is the rest of the formula (A12)
  • AI 2 stands in which R 32 is hydrogen, halogen, amino, ⁇ -Alkylarnino, di- (C ⁇ -C4 alkyl) amino, cyano, C 4 alkyl or C ⁇ -C 4 -halogenoalkyl having 1 to 5 halogen atoms is and R 33 is Halogen, C] -C 4 alkyl or Ci-G t -haloalkyl having 1 to 5 halogen atoms, or
  • A represents the rest of the formula (A 13) I 3), in which R 34 stands for hydrogen or C, -C 4 alkyl and R 35 stands for halogen or CC 4 alkyl, or
  • a for the rest of formula (A 14) (AI 4) is in which R represents hydrogen, halogen, -CC alkyl or -CC 4 haloalkyl having 1 to 5 halogen atoms, or
  • (AI 5) is in which R 37 represents halogen, hydroxy, CC 4 -alkyl, QQ-alkoxy, QQ-alkylthio, QQ-haloalkyl, QQ-haloalkylthio or QQ-haloalkoxy, each having 1 to 5 halogen atoms, or
  • R 38 for hydrogen, cyano, Ci-Q-alkyl, C ⁇ -C 4 haloalkyl with 1 to 5 halogen atoms, QQ-alkoxy-QQ-alkyl, hydroxy-QQ-alkyl, C ⁇ -C 4 alkylsulfonyl, di (Q- C 4 -alkyl) aminosulfonyl, Cj-Q-alkylcarbonyl or represents optionally substituted phenylsulfonyl or benzoyl, R 39 represents hydrogen, halogen, Ci-Q-alkyl or QQ-haloalkyl having 1 to 5 halogen atoms, R 40 represents hydrogen, Halogen, cyano, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, R 41 stands for hydrogen, halogen, Ci-Q-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, with the proviso that
  • (AI 7) is in which R 4 "stands for QQ-alkyl.
  • the compounds of the invention can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers are present. Both the E and the Z isomers, as well as the threo- and erythro- as well as the optical isomers, any mixtures of these isomers and the possible tautomeric forms are claimed.
  • isopentylcarboxanilides of the formula (I) are obtained by a) carboxylic acid derivatives of the formula (H) in which A has the meanings given above and X 1 represents halogen or hydroxy, with an aniline derivative of the formula (IU)
  • L, A and R 3 have the meanings given above with halides of the formula (TV) R 1-A_ ⁇ 2 (rV ) in which X 2 represents chlorine, bromine or iodine, R ' "A represents QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfinyl, QQ-haloalkylsulfonyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halogenocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QQ-alkyl) carbonyl-Q-C3-alkyl, (QQ-
  • R 1 , R 2 , R 3 and A have the meanings given above, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst, or e) isopentine derivatives of the formula (VH) in which R 1 , R 2 , R 3 and A have the meanings given above, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst.
  • Formula (I) generally defines the isopentylcarboxanilides according to the invention. Preferred radical definitions of the formulas mentioned above and below are given below. These definitions apply equally to the end products of the formula (I) and to all intermediates.
  • L preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings. L also preferably represents L-2.
  • L also preferably represents L-3.
  • L also preferably represents L-4.
  • L particularly preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings.
  • L is also particularly preferably L-2.
  • L very particularly preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings.
  • R 1 preferably represents hydrogen, QQ-alkyl, QQ-alkylsulfmyl, QQ-alkylsulfonyl, Q-Q-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, Q-Q-haloalkylsulfinyl, CrQ-haloalkylsulfonyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QQ-alkycarbonyl-QQ-alkyl, (QQ-alkoxy) carbonyl-QQ- alkyl; Halogen (QQ-alkyl) carbonyl-QC 3 -alkyl, halogen (-C-C 3 -alkoxy) carbonyl-
  • R 1 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloromethyl, trifluoromethyl, di
  • R 2 preferably represents hydrogen.
  • R 2 also preferably represents fluorine, fluorine being particularly preferably in the 4-, 5- or 6-position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide radical [cf. formula (I) above].
  • R 2 also preferably represents chlorine, chlorine being particularly preferably in the 5-position of the anilide residue [cf. formula (I) above]. Chlorine is also particularly preferably in the 4-position of the anilide residue. R 2 also preferably represents methyl, methyl being particularly preferably in the 3-position of the anilide radical [cf. formula (I) above]. R 2 also preferably stands for trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide residue [cf. formula (I) above].
  • R 3 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, QQ-alkyl, QQ-haloalkyl with 1 to 13 fluorine, chlorine and / or bromine atoms.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl or QC 4 -haloalkyl with 1 to 9 fluorine, chlorine - and / or bromine atoms.
  • R 3 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl.
  • R 4 preferably represents hydrogen, QQ-alkyl, QQ-alkoxy, QQ-alkoxy-QQ-alkyl, Q-Q-cycloalkyl; QQ-haloalkyl, QQ-haloalkoxy, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 4 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
  • R 5 and R 6 independently of one another preferably represent hydrogen, QQ-alkyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QQ-haloalkyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 5 and R 6 together with the nitrogen atom to which they are attached, preferably form a saturated heterocycle with 5 to 8 ring atoms, which is optionally monosubstituted to tetrasubstituted, identically or differently, by halogen or Q-Q-alkyl, the heterocycle 1 or 2 further, non-neighboring heteroatoms from the series oxygen, sulfur or NR 9 can contain.
  • R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 5 and R together with the nitrogen atom to which they are attached, particularly preferably form a saturated heterocycle from the morpholine series which may be monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine or methyl, Thiomorpholine or piperazine, where the piperazine on the second nitrogen atom can be substituted by R 9 .
  • R 7 and R 8 independently of one another preferably represent hydrogen, QQ-alkyl, C 3 -C 6 -cycloalkyl; QQ-haloalkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 7 and R 8 together with the nitrogen atom to which they are attached, preferably form a saturated heterocycle having 5 to 8 ring atoms, which may be mono- or polysubstituted, identically or differently, by halogen or Q-Q-alkyl, the heterocycle 1 or 2 further, non-neighboring heteroatoms from the series oxygen, sulfur or NR 9 can contain.
  • R 7 and R 8 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
  • R 7 and R 8 together with the nitrogen atom to which they are attached, particularly preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine or methyl, where the piperazine on the second nitrogen atom can be substituted by R 9 .
  • R 9 preferably represents hydrogen or QC 4 alkyl.
  • R 9 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
  • A preferably represents one of the radicals A1, A2, A3, A4, A5, A6, A9, A10, All, A12, A13, A14, A15 or A16.
  • A is also very particularly preferably the radical A2.
  • A also particularly preferably stands for the rest A4.
  • A also particularly preferably stands for the rest A5.
  • A also very particularly preferably represents the radical A6.
  • A also very particularly preferably represents the radical A9.
  • A also very particularly preferably represents the rest Al 1.
  • A also very particularly preferably represents the radical A12.
  • A also very particularly preferably represents the radical A 13.
  • A also very particularly preferably represents the radical A14.
  • A also very particularly preferably represents the rest of AI 6.
  • R 10 preferably represents hydrogen, hydroxyl, fo ⁇ rryl, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, QQ-haloalkyl, QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, difluoromethylthio, aminocarbonyl, ammocarbonylmethyl or aminocarbonylethyl with the proviso that R 10 is not iodine, if R n is hydrogen and with the proviso that R 10 is not for Trifluoromethyl or difluoromethyl is when R 3 and R ⁇ are hydrogen and R 12 is methyl.
  • R 10 particularly preferably represents hydrogen, hydroxy, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, monofluoromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, pentafluoroethyl, Cyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio, with the proviso that R 10 is not iodine, ⁇ venn R n is hydrogen, and with the proviso that R 10 is not represents trifluoromethyl or difluoromethyl when R 3 and R ⁇ are hydrogen and R 12 is methyl.
  • R 10 very particularly preferably represents hydrogen, hydroxyl, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, cyclopropyl, monofluoromethyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, -CHFCH 3 or difluoromethoxy, with the proviso that R 10 is not iodine, Rvenn R ⁇ is hydrogen, and with the proviso that R 10 is not trifluoromethyl or difluoromethyl when R 3 and R ⁇ are hydrogen and R 12 is methyl stand.
  • R 10 particularly preferably represents hydrogen, hydroxyl, formyl, chlorine, methyl, ethyl, methoxy, cyclopropyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, -CHFCH3 or difluoromethoxy, with the proviso that R 10 does not represent trifluoromethyl or difluoromethyl, when R 3 and R n are hydrogen and R 12 is methyl.
  • R ⁇ preferably represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
  • R ⁇ particularly preferably represents hydrogen, chlorine, bromine, iodine, methyl or -CHFCH 3 .
  • R 12 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl.
  • R 12 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
  • R 12 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.
  • R 12 particularly preferably represents methyl
  • R 13 and R 14 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 13 and R 14 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 13 and R 14 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 13 and R 14 particularly preferably each represent hydrogen.
  • R 1S preferably represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 15 particularly preferably represents fluorine, chlorine, bromine, iodine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
  • R 15 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.
  • R 15 particularly preferably represents chlorine or methyl.
  • R 16 and R 17 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 16 and R 17 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 16 and R 17 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine or methyl.
  • R 16 and R 17 particularly preferably each represent hydrogen.
  • R 18 preferably represents hydrogen, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 18 particularly preferably represents hydrogen, methyl or trifluoromethyl.
  • R 18 very particularly preferably represents methyl.
  • R 19 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, Q-Q-haloalkyl, QQ-haloalkoxy or QQ-haloalkylthio, each with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 19 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio.
  • R 19 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.
  • R 19 particularly preferably represents iodine, methyl, difluoromethyl or trifluoromethyl.
  • R 20 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QQ-haloalkyl or Q-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and or bromine atoms.
  • R 20 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, Difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.
  • R 20 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 21 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl or Ci-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms , QQ-Alkylsulf ⁇ nyl or QQ-Alkylsulfonyl.
  • R 21 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, Methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulfinyl or methylsulfonyl.
  • R 21 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methylsulfonyl , R 21 particularly preferably represents hydrogen.
  • R 22 preferably represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 22 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 22 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 23 preferably represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 23 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 23 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 24 and R 25 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 24 and R 25 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 24 and R 25 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine or methyl.
  • R 24 and R 25 particularly preferably each represent hydrogen.
  • R 26 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 26 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 26 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R 26 particularly preferably represents methyl or trifluoromethyl.
  • R 27 and R 28 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 27 and R 28 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 27 and R 28 particularly preferably each represent hydrogen.
  • R 29 preferably represents fluorine, chlorine, bromine, methyl, ethyl or QC 2 haloalkyl with 1 to 5 fluorine, chlorine and or bromine atoms.
  • R 29 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 29 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 29 particularly preferably represents methyl.
  • R 30 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-Q-alkylamino, di (QQ-alkyl) amino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 30 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
  • R 31 preferably represents fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, QQ-haloalkyl or QQ-haloalkoxy with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 31 particularly preferably represents fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxy, ethoxy, cyclopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 31 very particularly preferably represents fluorine, chlorine, bromine, hydroxy, methyl, methoxy, cyclopropyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 32 preferably represents hydrogen, fluorine, chlorine, bromine, amino, -CC alkylamino, di (QQ-alkyl) amino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 32 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 32 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 32 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
  • R 33 preferably represents fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 33 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 33 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 33 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
  • R preferably represents hydrogen, methyl or ethyl.
  • R> 3 particularly preferably represents methyl
  • R 35 preferably represents fluorine, chlorine, bromine, methyl or ethyl.
  • R 35 particularly preferably represents fluorine, chlorine or methyl.
  • R 36 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
  • R 37 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QC 2 -haloalkyl or Q-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 37 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl.
  • R 37 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 38 preferably represents hydrogen, methyl, ethyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, QQ-alkoxy-QQ-alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl.
  • R 38 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl.
  • R 38 very particularly preferably represents methyl or methoxymethyl.
  • R 39 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 39 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl.
  • R 39 very particularly preferably represents hydrogen or methyl.
  • R 40 preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 40 particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
  • R 40 very particularly preferably represents hydrogen, fluorine, methyl or trifluoromethyl.
  • R 41 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
  • R 41 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.
  • R 41 very particularly preferably represents hydrogen or trifluoromethyl.
  • R 42 preferably represents methyl, ethyl, n-propyl or isopropyl.
  • R 42 is particularly preferably methyl or ethyl.
  • R 3 is halogen, preferably fluorine, chlorine, bromine or iodine, particularly preferably fluorine, chlorine or bromine, very particularly preferably for
  • R 3 is for QQ-alkyl, preferably for
  • QQ-alkyl particularly preferably methyl, ethyl, n-, iso-propyl, n-, iso-, sec- or tert-butyl, very particularly preferably methyl or ethyl.
  • R 3 for QQ-haloalkyl preferably for QQ-haloalkyl with 1 to 13 fluorine, chlorine and / or bromine atoms, particularly preferably for QQ-haloalkyl with 1 to 9 fluorine, Chlorine and / or bromine atoms, very particularly preferably represents trifluoromethyl.
  • Saturated or unsaturated hydrocarbon tests such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • Halogen substituted residues such as e.g. Haloalkyl, are halogenated once or several times. In the case of multiple halogenation, the halogen atoms can be the same or different.
  • Halogen stands for fluorine, chlorine, bromine and iodine, in particular for fluorine, chlorine and bromine.
  • Preferred, particularly preferred or very particularly preferred are compounds of the formula (I) which each carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
  • process (a) If 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and [2- (3-methylbutyl) phenyl] amine are used as starting materials, process (a) according to the invention can be carried out by the following formula scheme can be illustrated:
  • Formula ( ⁇ ) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process (a) according to the invention.
  • A has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for A in connection with the description of the compounds of the formula (I) according to the invention.
  • X 1 preferably represents chlorine, bromine or hydroxy.
  • the carboxylic acid derivatives of the formula (11) are known and / or can be prepared by known processes (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313).
  • Formula (10) provides a general definition of the aniline derivatives which are further required as starting materials for carrying out process (a) according to the invention.
  • L, R 1 and R 3 have preferred, particularly preferably or very particularly preferably those meanings which have already occurred in connection with the description of the compounds of the formula according to the invention (I) for these radicals as preferred, particularly preferred or very particularly preferred.
  • aniline derivatives of the formula (IQ), in which L stands for L-1, are partly new.
  • Aniline derivatives of the formula (Uf) in which L is L-1 can be prepared by, f) cyanoanilines of the formula (V i)
  • R 1 , R 2 and R 3 have the meanings given above, in a second step with hydrazine (or hydrazine hydrate) in the presence of a base (for example alkali or alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide) and, if appropriate, in the presence of a Converts diluent.
  • a base for example alkali or alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide
  • the formula (VflT) provides a general definition of the cyanoanilines required as starting materials for carrying out process (f) according to the invention.
  • R 1 and R 2 have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (T>) as preferred, particularly preferred or very particularly preferred for these residues were specified.
  • the cyanoanilines of the formula (VIII) are known and / or can be prepared by known processes. Cyanoanilines of the formula (VTfl) in which R 1 is not hydrogen can be obtained by using cyanoanilines of the formula (Va)
  • Formula (IX) provides a general definition of the Grignard reagents which are further required as starting materials for carrying out process (f) according to the invention.
  • R 3 has preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, have been indicated as preferred, particularly preferred or very particularly preferred for this radical were.
  • X 3 preferably represents bromine.
  • the Grignard reagents of the formula (TX) are known or can be obtained by known processes.
  • alkanonanilines of the formula (X) which are run through as intermediates in process (f) according to the invention are new and likewise the subject of this application.
  • the radicals R 1 , R 2 and R 3 have preferred, particularly preferably or very particularly preferably, those meanings which are already preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention, were particularly preferred or very particularly preferably specified.
  • Hydrazine (or hydrazine hydrate), which is also required as a reagent in process (f) according to the invention, is a known synthetic chemical.
  • the method (f) according to the invention can be carried out in various variants. It is thus possible first to prepare cyanoanilines of the formula (Va) to give the corresponding alkanonanilines of the formula (VTI-a) in which R 2 and R 3 have the meanings given above, which is then optionally with halides of the formula (IV) D 1 -A v 2 R —X (iv) in which R 1_A has the meanings given above, in the presence of a Base and in the presence of a diluent to the corresponding alkanonanilines of the formula (X). [The reaction conditions of process (b) apply accordingly.]
  • R 1_B for QQ-alkyl, QQ-alkylsulfinyl, QC 6 -alkylsulfonyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; CC 6 -haloalkyl, CC 4 -haloalkylthio, QQ-haloalkylsulfinyl, QQ-haloalkylsulfonyl, halo -CC 4 -alkoxy-C r C -alkyl, C 3 -C 8 -halo-cycloalkyl, each with 1 to 9 fluoro-, Chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QC 3 -alkyl) carbonyl-QQ-alkyl, (QQ-alkoxy) carbonyl-QC 3 -alkyl; Halogen (QQ-alkyl) carbonyl-Q
  • R 3 are applied to R 1_B and R 3 "B accordingly, whereby in case a) R 1_B does not stand for hydrogen and in case b) R 3" B does not stand for hydrogen.
  • the preferred, particularly preferred or very particularly preferred meanings of R 2 , R 4 , R 5 , R 6 , R and R also apply to the new compounds of the formula (Dl-b).
  • Meanings have optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst.
  • Formula (XI) provides a general definition of the aniline halides required as starting materials for carrying out process (g) according to the invention.
  • R 2 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were.
  • R 1_A preferably, particularly preferably or very particularly preferably has those meanings which together with the description of the compounds of the formula (TV) as preferred, particularly preferred or very particularly preferred for this radical.
  • aniline halides of formula (XI) are known and / or can be prepared by known methods, e.g. can be obtained from the corresponding derivatives unsubstituted on nitrogen by reaction with the halides of the formula (IV).
  • Formula (XU) provides a general definition of the alkynes still required as starting materials for carrying out process (g) according to the invention.
  • R 3 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were.
  • the alkynes of the formula (XU) are known.
  • R 2 and R 3 have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these residues were specified.
  • R 1_A preferably, particularly preferably or very particularly preferably has those meanings which are given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (IV).
  • alkynanilines of the formula (XIO) are known. They are obtained by process (g) according to the invention.
  • R 1_A is selected accordingly in order to fulfill the function of a protective group which, after the process (g) according to the invention, is used again by customary methods can be removed.
  • Aniline derivatives of the formula (JE) in which L is L-2, L-3 or L-4 and R 1 is not hydrogen can be obtained by using anilines of the formula ( ⁇ i-c) in which
  • L 1 stands for L-2, L-3 or L-4 and
  • L-2, L-3, L-4 and R 3 have the meanings given above, with halides of the formula (IV) p1-A ⁇ 2 RX (rv) in which R ⁇ A and X 2 has the meanings indicated above, in In the presence of a base and in the presence of a diluent. [The reaction conditions of process (b) apply accordingly.]
  • Formula (Ia) provides a general definition of the isopentylcarboxanilides required as starting materials for carrying out process (b) according to the invention.
  • R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or were very particularly preferably specified for these radicals.
  • Formula (IV) provides a general definition of the halides which are further required as starting materials for carrying out process (b) according to the invention.
  • R 1_A preferably represents QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloal- kylsulfinyl, QQ-haloalkylsulfonyl, halo -CC 3 -alkoxy-C 3 -alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Q-Q-alkyl, (QQ-alkyl) carbonyl-QQ-alkyl, (QC 3 -alkoxy) carbonyl-QQ-alkyl; Halogen (CrC 3 -alkyl) carbonyl -CC 3 -alkyl, halogen- (
  • R 1_A particularly preferably represents methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso- , sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichl Trifluoroethyl,
  • X 2 preferably represents chlorine or bromine.
  • Formula (V) provides a general definition of the isopentone derivatives required as starting materials for carrying out process (c) according to the invention.
  • R 1 , R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which have already been given preference in connection with the description of the compounds of the formula (I) according to the invention were preferred or very particularly preferred for these radicals.
  • the isopentone derivatives of the formula (V) are new. They are obtained by h) carboxylic acid derivatives of the formula (H) O), A ⁇ . (H in which A has the meanings given above and X 1 represents halogen or hydroxy, with alkanonanilines of the formula (X)
  • R 1 , R 2 and R 3 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
  • Formula (VT) provides a general definition of the isopentene derivatives required as starting materials for carrying out process (d) according to the invention.
  • R 1 , R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which have been preferred, particularly preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were very particularly preferably indicated for these residues.
  • the isopentene derivatives of the formula (VI) are new. They are obtained by j) carboxamides of the formula (XTV)
  • R 1 , R 2 and A have preferred, particularly preferably or very particularly preferably those meanings which have been preferred, particularly preferred or very particularly in connection with the description of the compounds of the formula (I) according to the invention were preferably given for these residues.
  • X 5 preferably represents bromine or -OSO 2 CF 3 .
  • the carboxamides of the formula (XIV) are known or can be obtained by known methods (cf. WO 02/08195 and WO 02/08197).
  • Formula (XV) provides a general definition of the alkenes which are further required as starting materials for carrying out process (j) according to the invention.
  • R 3 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were.
  • the alkenes of the formula (XV) are known.
  • Formula (VE) provides a general definition of the isopentene derivatives required as starting materials for carrying out process (e) according to the invention.
  • R 1 , R 2 , R 3 and A have preferred, particularly preferred or very particularly preferred those meanings which have been preferred, particularly preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were very particularly preferably indicated for these residues.
  • the isopentin derivatives of the formula (VE), in which A is not AI, are new.
  • the isopentine derivatives of the formula (VE) are obtained by k) carboxamides of the formula (XIV)
  • R 1 , R 2 and A have the meanings given above and X 5 represents chlorine, bromine, iodine or -OSO 2 CF 3 , with alkynes of the formula (KE) R ⁇ CH, H ZZ ⁇ (x ⁇ ) CH 3 in which R 3 has the meanings given above, in the presence of a catalyst, if appropriate in the presence of a base and if appropriate in the presence of a diluent.
  • Suitable diluents for carrying out processes (a) and (h) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as 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 or amide, such as
  • Processes (a) and (h) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All common inorganic or organic bases come as such question.
  • These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triemylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine N-methyl
  • Processes (a) and (h) according to the invention are optionally carried out in the presence of a suitable condensing agent.
  • a suitable condensing agent All condensation agents that can normally be used for such amidation reactions are suitable as such.
  • Acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride may be mentioned as examples;
  • Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride;
  • Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-e
  • Processes (a) and (h) according to the invention are optionally carried out in the presence of a catalyst.
  • a catalyst examples include 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimemylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a) and (h) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • 0.2 to 5 mol, preferably 0.5 to 2 mol, of alkanonaniline of the formula are generally employed per mol of the carboxylic acid derivative of the formula (H) (X) a.
  • Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents.
  • aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-
  • Process (b) according to the invention is carried out in the presence of a base.
  • a base All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, N-methylpiperidine, N-methylmo holin, N, N
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C.
  • 0.2 to 5 mol, preferably 0.5 to 2 mol, of halide of the formula (TV) are generally employed per mole of the isopentylcarboxanilide of the formula (Ia) ) on.
  • inert organic solvents are suitable as diluents for carrying out process (c) according to the invention and the second step of process (f).
  • These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-arnyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, 1,2-diethoxyethane or ani
  • Process (c) according to the invention and the second step of process (f) are carried out in the presence of a base.
  • a base such as alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, are preferred.
  • reaction temperatures can be varied within a substantial range. In general, temperatures from 100 ° C to 300 ° C, preferably at temperatures from 150 ° C to 250 ° C.
  • 0.2 to 5 mol, preferably 0.5 to 3 mol, of hydrazine (or.) are generally employed per mole of the isopentone derivative of the formula (V) Hydrazine hydrate).
  • Suitable diluents for carrying out processes (d) and (e) according to the invention and the second step of process (g) are all inert organic solvents.
  • These preferably include aliphatic or alicyclic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; Alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol
  • Processes (d) and (e) according to the invention and the second step of process (g) are carried out in the presence of a catalyst.
  • a catalyst As such, all catalysts that are suitable for Hydrogenations are commonly used. Examples include: Raney nickel, palladium or platinum, optionally on a carrier material, such as activated carbon.
  • reaction temperatures can be varied within a substantial range. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C.
  • the processes (d) and (e) according to the invention and the second step of process (g) are carried out under a hydrogen pressure between 0.5 and 200 bar, preferably between 2 and 50 bar, particularly preferably between 3 and 10 bar.
  • Suitable diluents for carrying out the first step of process (f) are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane.
  • aliphatic or alicyclic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin
  • Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-a
  • reaction temperatures can be varied within a substantial range when carrying out the first step of process (f). In general, temperatures from 0 ° C to 200 ° C, preferably at temperatures from 20 ° C to 150 ° C.
  • inert organic solvents are suitable as diluents for carrying out the first step of process (g) and processes (j) and (k) according to the invention.
  • These preferably include nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Ethers, such as diethyl ether, diisopropyl ether, Methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-
  • the first step of process (g) and processes (j) and (k) according to the invention are optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butylate , Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine,
  • the first step of process (g) and processes (j) and (k) according to the invention are carried out in the presence of one or more catalysts.
  • Palladium salts or complexes are particularly suitable for this.
  • Palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride are preferably used for this purpose.
  • a palladium complex can also be generated in the reaction mixture if a palladium salt and a complex ligand are added separately to the reaction.
  • Organophosphorus compounds are preferred as ligands.
  • Examples include: triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis (diphenylphosphino) -l, r-binaphthyl, dicyclohexylphosphine biphenyl, 1,4-bis (diphenylphosphino) butane, bisdiphenylphosphinoferrocene, di (tert.
  • ligands can also be dispensed with.
  • the first step of process (g) and processes (j) and (k) according to the invention are also optionally carried out in the presence of a further metal salt, such as copper salts, for example copper (I) iodide.
  • a further metal salt such as copper salts, for example copper (I) iodide.
  • reaction temperatures can be varied within a substantial range. In the Generally one works at temperatures from 20 ° C to 180 ° C, preferably at temperatures from 50 ° C to 150 ° C.
  • the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
  • Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as, for example, Erwinia amylovora
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Altemaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides
  • Rhizoctonia species such as, for example, Rhizoctonia solani.
  • the active substances according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • plant-strengthening (resistance-inducing) substances are to be understood as substances which are able to stimulate the defense system of plants in such a way that the treated plants are subsequently inoculated with undesired microorganisms develop extensive resistance to these microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can thus be used to protect plants against the infestation by the named pathogens within a certain period of time after the treatment.
  • the period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds.
  • the active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Puccinia species, and for diseases in wine, fruit and vegetable cultivation, for example against Botrytis, Venturia or Altemaria species.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can, if appropriate in certain concentrations and application rates, also be used as herbicides, for influencing plant growth and for combating animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being 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, including for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are understood to mean non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms .
  • parts of production systems for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms.
  • technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.
  • Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials.
  • the active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
  • Microorganisms of the following genera may be mentioned, for example:
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Aspergillus niger
  • Chaetomium like 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 pullulans
  • 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 ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions
  • alcohols such as butanol or glycol
  • Ethers and esters ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and diethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • Solid carrier materials come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates.
  • Solid carriers for granules are possible: e.g.
  • Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: eg lignin sulfate and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can 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 can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • isoprothiolane Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone;
  • mepanipyrim mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam;
  • metiram metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron;
  • phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; Procymidones; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole;
  • pyraclostrobin Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl;
  • the compounds of the formula (I) according to the invention also have very good antimycotic effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus nig and Aspergillus , Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum eg against Aspergillus species such as Aspergillus nig and Aspergillus
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is in no way a limitation of
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to remove the active ingredients using the ultra-low-volume process. bring or inject the drug preparation or the drug itself into the soil. The seeds of the plants can also be treated.
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
  • the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • all plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or one Enhancing the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, Increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the Further and particularly highlighted 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 viruses as well as an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to the toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryUA, CryDIA, Gyi ⁇ B2, Cry9c Cry2Ab, Cry3Bb and CryTF as well as their combinations) are generated in the plants (hereinafter "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryUA, CryDIA, Gyi ⁇ B2, Cry9c Cry2Ab, Cry3Bb and CryTF as well as their combinations
  • the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
  • properties (“traits”) the increased tolerance of the plants to certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT" gene) are also particularly emphasized.
  • the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • t plants are corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (eg maize , Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g.
  • rapeseed rapeseed
  • IMI® tolerance to Imidazolinone
  • STS® tolerance to sulfonylureas such as maize
  • the herbicide-resistant plants include the varieties marketed under the name Clearf ⁇ eld® (eg maize). Of course, these statements also apply to those developed in the future or to the future
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • a solution of 29.5 g (0.25 mol) of antraniliconitrile in 150 ml of tetrahydrofuran is added dropwise to a suspension consisting of 18.2 g (0.75 mol) of magnesium, 375 ml of a 2 M solution of isobutylmagnesium bromide in tetrahydrofuran and 15 ml of diethyl ether.
  • 100 ml of water are added to the reaction mixture at 0 ° C., and the pH is adjusted to 6 using hydrochloric acid.
  • the organic phase is washed with water and dried over magnesium sulfate.
  • the logP values specified in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; 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 on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
  • Botrytis test (bean) / protective
  • Solvent 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Botrytis test (bean) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.
  • Evaluation is carried out 8 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

Abstract

The invention relates to novel isopentyl carboxanilides of formula (I), wherein L, R1, R3 and A have the meaning cited in the description, to several methods for the production of said substances and to the use thereof in order to combat undesired micro-organisms, in addition to intermediate products and to the production thereof.

Description

ISOPENTYLCARBOXANILIDE ZUR BEKÄMPFUNG VON UNTERWÜNSCHTEN MIKROORGANISMEN ISOPENTYLCARBOXANILIDES FOR CONTROLLING UNDESIRABLE MICROORGANISMS
Die vorliegende Erfindung betrifft neue Isopentylcarboxanilide, mehrere Verfahren zu deren Herstellung und deren Verwendung zur Bekämpfung von unerwünschten Mikroorganismen.The present invention relates to new isopentylcarboxanilides, several processes for their preparation and their use for controlling unwanted microorganisms.
Es ist bereits bekannt, dass zahlreiche Carboxanilide fungizide Eigenschaften besitzen (vgl. z.B. WO 02/059086, WO 00/09482, EP-A 0 824099, EP-A 0 755 927, EP-A 0 589 301, EP-A 0 545 099, JP 11-335364, JP 10-310577 und JP 10-251240). So sind beispielsweise l-Methyl-N-[2-(3-methylbu- tyl)phenyl]-3-(trifluormethyl)-m-pyrazol-4-carboxamid (aus EP-A 0 824 099) und 2,5-Dimethyl-N- [3-(3-methylbutyl)phenyl]-3-furamid (aus EP-A 0 755 927) bekannt. Die Wirksamkeit dieser Stoffe ist gut, lässt aber bei niedrigen Aufwandmengen in manchen Fällen zu wünschen übrig.It is already known that numerous carboxanilides have fungicidal properties (cf., for example, WO 02/059086, WO 00/09482, EP-A 0 824099, EP-A 0 755 927, EP-A 0 589 301, EP-A 0 545 099, JP 11-335364, JP 10-310577 and JP 10-251240). For example, l-methyl-N- [2- (3-methylbutyl) phenyl] -3- (trifluoromethyl) -m-pyrazole-4-carboxamide (from EP-A 0 824 099) and 2,5-dimethyl -N- [3- (3-methylbutyl) phenyl] -3-furamide (from EP-A 0 755 927) is known. The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.
Es wurden nun neue Isopentylcarboxanilide der Formel (I)New isopentylcarboxanilides of the formula (I)
gefunden, in welcher found in which
steht, wobei die mit * markierte Bindung mit dem Amid verbunden ist, während die mit # markierte Bindung mit der Alkylseitenkette verknüpft ist, R1 für Wasserstoff, C C8-Alkyl, C1-CVAl ylsulfinyl, d-C6-Arkylsulfonyl, C1-C4-Alkoxy-C1-C4- alkyl, C3-C8-Cycloalkyl; C,-C6-Halogenalkyl, CrC4-Halogenalkylthio, CrC4-Halogenalkyl- sulfϊnyl, Cι-C4-Halogenalkylsulfonyl, Halogen-Cι-C4-alkoxy-Cι-C -alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Cι-C3- alkyl, (C C3-Alkyl)carbonyl-CrC3-alkyl, (Cι-C3-Alkoxy)carbonyl-Cι-C3-alkyl; Halogen-(C C3-alkyl)carbonyl-C C3-alkyl, Halogen-(Cι-C3-alkoxy)carbonyl-Cι-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Cι-C8-Alkyl)carbonyl, (Cι-C8-Alkoxy)carbonyl, (C C -Alkoxy-C C4-alkyl)carbonyl, (C3- C8-Cycloalkyl)carbonyl; (Ci -C6-Halogenalkyl)carbonyl, (Ci -C6-Halogenalkoxy)carbonyl, (Halogen-C C -alkoxy-Cι -C4-alkyl)carbonyl, (C3-C8-Halogencycloalkyl)carbonyl mit j eweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, -COTMR5R6 oder -CH2NR7R8 steht,stands, wherein the bond marked with * is linked to the amide, while the bond marked with # is linked to the alkyl side chain, R 1 for hydrogen, CC 8 alkyl, C 1 -CVAl ylsulfinyl, dC 6 arylsulfonyl, C 1 -C 4 Alkoxy-C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl; C, -C 6 haloalkyl, C r C 4 haloalkylthio, C r C 4 haloalkyl sulfϊnyl, Cι-C4-haloalkylsulfonyl, halo-Cι-C4-alkoxy-Cι-C alkyl, C 3 -C 8- halo-cycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Cι-C 3 - alkyl, (CC 3 -alkyl) carbonyl-C r C 3 alkyl, (Cι-C3 alkoxy) carbonyl-Cι-C3-alkyl; Halogen (CC 3 -alkyl) carbonyl-C 3 -alkyl, halogen- (-C-C3-alkoxy) carbonyl-Cι-C 3 alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (-C 8 alkyl) carbonyl, (C 8 alkoxy) carbonyl, (CC alkoxy-C 4 alkyl) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Ci -C 6 haloalkyl) carbonyl, (Ci -C 6 haloalkoxy) carbonyl, (halo-C C -alkoxy-Cι -C 4 alkyl) carbonyl, (C 3 -C 8 halocycloalkyl) carbonyl with each 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 4 , -COTMR 5 R 6 or -CH 2 NR 7 R 8 ,
R2 für Wasserstoff, Fluor, Chlor, Methyl oder Trifluormerhyl steht,R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R3 für Wasserstoff, Halogen, Cι-C8-Alkyl, C C8-Halogenalkyl steht, R4 für Wasserstoff, CrC8-Alkyl, C C8-Alkoxy, CrC4-Alkoxy-C,-C4-alkyl, C3-C8-Cycloalkyl; CrC6-Halogenalkyl, Cι-C6-Halogenalkoxy, Halogen- ^-alkoxy-Ci-Gi-alkyl, C3-C8- Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,R 3 is hydrogen, halogen, Cι-C8 alkyl, CC is 8 haloalkyl, R 4 is hydrogen, C r C 8 alkyl, CC 8 alkoxy, C r C 4 alkoxy-C, -C 4 - alkyl, C 3 -C 8 cycloalkyl; C r C 6 haloalkyl, C 1 -C 6 haloalkoxy, halogen ^ alkoxy-Ci-Gi-alkyl, C 3 -C 8 halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 unabhängig voneinander jeweils für Wasserstoff, Cι-C8-Alkyl, Cι-C4-Alkoxy-Cι-C4-alkyl, C3-C8-Cycloalkyl; -Cs-Halogenalkyl, Halogen-Cι-C4-alkoxy-CrC4-alkyl, C3-C8-Halogen- cycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 5 and R 6 each independently are hydrogen, C 8 -alkyl, C 4 -alkoxy-Cι-C 4 alkyl, C 3 -C 8 cycloalkyl; -Cs-haloalkyl, halo -CC 4 -alkoxy-C r C 4 -alkyl, C 3 -C 8 -halo-cycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder C 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 NR9 enthalten kann,R 5 and R 6, together with the nitrogen atom to which they are attached, form a saturated heterocycle with 5 to 8 ring atoms which is optionally mono- or polysubstituted, identically or differently, by halogen or CC 4 -alkyl, the heterocycle 1 or 2 more may contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R7 und R8 unabhängig voneinander für Wasserstoff, Cι-C8-Alkyl, C3-C8-Cycloalkyl; Q-Cs-Halogenalkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 7 and R 8 independently of one another for hydrogen, -CC 8 alkyl, C 3 -C 8 cycloalkyl; Q-Cs-haloalkyl, C 3 -C 8 -halogenocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder C 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 NR9 enthalten kann,R 7 and R 8 together with the nitrogen atom to which they are attached form an optionally mono- or polysubstituted, identical or different, halogen or CC 4 alkyl-substituted saturated heterocycle having 5 to 8 ring atoms, the heterocycle 1 or 2 more may contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R9 für Wasserstoff oder CrC5-Alkyl steht,R 9 represents hydrogen or C r C 5 alkyl,
A für den Rest der Formel (AI)A for the rest of the formula (AI)
(AI) steht, in welcher R10 für Wasserstoff, Hydroxy, Formyl, Cyano, Halogen, Nitro, C C4-Alkyl, C C4- Alkoxy, CrC4-Alkylthio, C3-C6-Cycloalkyl, C]-C4-Halogenalkyl, -Q-Halogenalk- oxy oder Cι-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocarbonyl-Cι-C4-alkyl steht, R11 für Wasserstoff, Halogen, Cyano, C,-C4-Alkyl, - -Alkoxy, C1-C4-Alkylthio, - C4-Halogenalkyl oder C C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, steht und R12 für Wasserstoff, C,-C4-Alkyl, Hydroxy-C C4-alkyl, C2-C6-Alkenyl, C3-C6-Cyclo- alkyl, C,-C4-Alkylthio-CrC4-alkyl, CrC4-Alkoxy-CrC4-alkyl, C,-C4-Halogenalkyl, C C4-Halogenalkylthio-Cι-C4-alkyl, C C4-Halogenalkoxy-Cι-C4-alkyl mit jeweils 1 bis 5 Halogenatomen, oder für Phenyl steht, mit der Maßgabe, dass R10 nicht für lod steht, wenn R11 für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rn für Wasserstoff und R12 für Methyl stehen, oder(AI) is in which R 10 for hydrogen, hydroxy, formyl, cyano, halogen, nitro, CC 4 alkyl, CC 4 alkoxy, C r C 4 alkylthio, C 3 -C 6 cycloalkyl, C] -C 4 haloalkyl, -Q -Halogenalk- oxy or -CC 4 -haloalkylthio, each with 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl -CC-C 4 alkyl, R 11 represents hydrogen, halogen, cyano, C, -C 4 alkyl, - alkoxy , C 1 -C 4 alkylthio, - C 4 haloalkyl or CC 4 haloalkylthio, each with 1 to 5 halogen atoms, and R 12 for hydrogen, C, -C 4 alkyl, hydroxy-C C 4 alkyl, C 2 -C 6 alkenyl, C 3 -C 6 cycloalkyl, C, -C 4 alkylthio-CrC 4 - alkyl, C r C 4 -alkoxy-C r C 4 -alkyl, C, -C 4 -haloalkyl, CC 4 -haloalkylthio -CC 4 -alkyl, CC 4 -haloalkoxy -CC 4 -alkyl, each with 1 to 5 halogen atoms, or represents phenyl, with the proviso that R 10 is not iodine when R 11 is hydrogen and with the proviso that R 10 is not trifluoromethyl or difluoromethyl when R 3 and R n are Hydrogen and R 12 are methyl, or
A für den Rest der Formel (A2) steht, in welcher R13 und R14 unabhängig voneinander für Wasserstoff, Halogen, C C4-Alkyl oder C C4-Halo- genalkyl mit 1 bis 5 Halogenatomen stehen und R15 für Halogen, Cyano oder C C4-Alkyl, oder Cι-C4-Halogenalkyl oder Cι-C4-Halogen- alkoxy mit jeweils 1 bis 5 Halogenatomen steht, oderA represents the rest of the formula (A2), in which 4 alkyl or C 4 -Halo-, R 13 and R 14 are independently hydrogen, halogen, CC genalkyl having 1 to 5 halogen atoms and R 15 represents halogen, cyano or C 4 -alkyl, or Cι-C 4 haloalkyl or C 1 -C 4 -alkoxy, each with 1 to 5 halogen atoms, or
A für den Rest der Formel (A3) (A3) steht, in welcher R16 und R17 unabhängig voneinander für Wasserstoff, Halogen, Cι-C4-Alkyl oder Cι-C4-Halo- genalkyl mit 1 bis 5 Halogenatomen stehen und R18 für Wasserstoff, Cι-C4-Alkyl oder Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A4)A stands for the rest of the formula (A3) (A3), in which R 16 and R 17 independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 haloalkyl having 1 to 5 halogen atoms and R 18 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 Haloalkyl having 1 to 5 halogen atoms, or A for the rest of the formula (A4)
(A4) steht, in welcher R19 für Wasserstoff, Halogen, Hydroxy, Cyano, -Cö-Alkyl, Cι-C -Halogenalkyl, C C4- Halogenalkoxy oder Cι-C4-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A5)(A4) is in which R 19 is hydrogen, halogen, hydroxy, cyano, -C ö -alkyl, C haloalkyl, CC 4 - represents halogenoalkoxy or Cι-C4-haloalkylthio having in each case 1 to 5 halogen atoms, or A is the radical of the formula ( A5)
|| T (A5) steht, in welcher R20 für Halogen, Hydroxy, Cyano, C C4-Alkyl, -C4-Alkoxy, - -Alkylthio, C,-C4- Halogenalkyl, C]-C4-Halogenalkylthio oder Cι-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht und R21 für Wasserstoff, Halogen, Cyano, C C4-Alkyl, C C -Alkoxy, Cι-C4-Alkylthio, Cj- C4-Halogenalkyl, Cι-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, C C4- Alkylsulfinyl oder Cι-C4-Alkylsulfonyl steht, oder A für den Rest der Formel (A6)|| T (A5) stands in which R 20 for halogen, hydroxy, cyano, CC 4 -alkyl, -C 4 -alkoxy, - -alkylthio, C, -C 4 - haloalkyl, C] -C 4 -haloalkylthio or -C-C 4 -haloalkoxy, each with 1 to 5 halogen atoms, and R 21 is hydrogen, halogen, cyano, CC 4 alkyl, CC -alkoxy, C 4 alkylthio, CJ-C4 haloalkyl, Cι-C 4 -haloalkoxy having 1 to 5 halogen atoms, CC 4 - alkylsulfinyl or -CC 4 alkylsulfonyl, or A for the rest of the formula (A6)
(A6) steht, oder(A6) stands, or
A für den Rest der Formel (A7)A for the rest of formula (A7)
(A7) steht, in welcher R22 für C C4-Alkyl oder C C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A8)(A7) stands in which R 22 represents CC 4 alkyl or CC 4 haloalkyl having 1 to 5 halogen atoms, or A represents the rest of the formula (A8)
(A8) steht, in welcher R für C C -Alkyl oder Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder(A8) stands in which R represents CC alkyl or -CC 4 haloalkyl having 1 to 5 halogen atoms, or
A für den Rest der Formel (A9)A for the rest of formula (A9)
(A9) steht, in welcher R24 und R25 unabhängig voneinander für Wasserstoff, Halogen, Amino, C C4-Alkyl oder - C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht und R26 für Wasserstoff, CrC4-Alkyl oder C C4-Halogenalkyl mit 1 to 5 Halogenatomen steht, mit der Maßgabe, dass R24 und R26 nicht gleichzeitig für Methyl stehen, wenn R25 für Wasser- stoff steht, oder A für den Rest der Formel ( A 10) (A10) steht, in welcher R27 und R28 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, -GrAlkyl oder C C4-Halogenalkyl mit 1 bis 5 Halogenatomen stehen und R29 für Halogen, CrC4-Alkyl oder C C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder(A9) stands in which R 24 and R 25 independently of one another are hydrogen, halogen, amino, CC 4 -alkyl or - C 4 -haloalkyl having 1 to 5 halogen atoms and R 26 is hydrogen, C r C 4 -alkyl or CC 4 -haloalkyl with 1 to 5 halogen atoms, with the proviso that R 24 and R 26 do not simultaneously stand for methyl if R 25 stands for hydrogen, or A for the rest of the formula (A 10) (A10) stands in which R 27 and R 28 independently represent hydrogen, halogen, amino, nitro, -GrAlkyl or CC 4 haloalkyl with 1 to 5 halogen atoms and R 29 for halogen, C r C 4 alkyl or CC 4 haloalkyl with 1 to 5 Halogen atoms, or
A für den Rest der Formel (Al l) (All) steht, in welcher R30 für Wasserstoff, Halogen, Amino, C C4-Alkylarmno, Di-(Cι-C -alkyl)amino, Cyano, Cι-C -Alkyl oder Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht und R31 für Halogen, Hydroxy, d-Q-Alkyl, Q- -Alkoxy, C3-C6-Cycloalkyl, -C4- Halogenalkyl oder Cι-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, mit der Maßgabe, dass R31 nicht für Trifluormethyl, Difluormethyl oder Methyl steht, wenn R3 für Wasserstoff und R30 für Methyl stehen, oder A für den Rest der Formel (A12)A stands for the rest of the formula (A1) (All), in which R 30 represents hydrogen, halogen, amino, CC 4 alkyl armno, di (C 1 -C 4 alkyl) amino, cyano, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl having 1 to 5 halogen atoms and R 31 represents halogen , Hydroxy, dQ-alkyl, Q- alkoxy, C 3 -C 6 cycloalkyl, -C 4 - haloalkyl or -C-C 4 haloalkoxy, each with 1 to 5 halogen atoms, with the proviso that R 31 is not trifluoromethyl , Difluoromethyl or methyl when R 3 is hydrogen and R 30 is methyl, or A is the rest of the formula (A12)
(AI 2) steht, in welcher R32 für Wasserstoff, Halogen, Amino, ^-Alkylarnino, Di-(Cι-C4-alkyl)amino, Cyano, Cι-C4-Alkyl oder Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht und R33 für Halogen, C]-C4-Alkyl oder Ci-Gt-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder(AI 2) stands in which R 32 is hydrogen, halogen, amino, ^ -Alkylarnino, di- (Cι-C4 alkyl) amino, cyano, C 4 alkyl or Cι-C 4 -halogenoalkyl having 1 to 5 halogen atoms is and R 33 is Halogen, C] -C 4 alkyl or Ci-G t -haloalkyl having 1 to 5 halogen atoms, or
A für den Rest der Formel (A 13) I 3) steht, in welcher R34 für Wasserstoff oder C,-C4-Alkyl steht und R35 flir Halogen oder C C4-Alkyl steht, oderA represents the rest of the formula (A 13) I 3), in which R 34 stands for hydrogen or C, -C 4 alkyl and R 35 stands for halogen or CC 4 alkyl, or
A für den Rest der Formel (A 14) (AI 4) steht, in welcher R für Wasserstoff, Halogen, Cι-C -Alkyl oder Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oderA for the rest of formula (A 14) (AI 4) is in which R represents hydrogen, halogen, -CC alkyl or -CC 4 haloalkyl having 1 to 5 halogen atoms, or
A für den Rest der Formel (A 15)A for the rest of formula (A 15)
(AI 5) steht, in welcher R37 für Halogen, Hydroxy, C C4-Alkyl, Q-Q-Alkoxy, Q-Q-Alkylthio, Q-Q-Halogen- alkyl, Q-Q-Halogenalkylthio oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, oder(AI 5) is in which R 37 represents halogen, hydroxy, CC 4 -alkyl, QQ-alkoxy, QQ-alkylthio, QQ-haloalkyl, QQ-haloalkylthio or QQ-haloalkoxy, each having 1 to 5 halogen atoms, or
A für den Rest der Formel (A 16)A for the rest of the formula (A 16)
(A16) steht, in welcher R38 für Wasserstoff, Cyano, Ci-Q-Alkyl, Cι-C4-Halogenalkyl mit 1 bis 5 Halogenatomen, Q-Q-Alkoxy-Q-Q-alkyl, Hydroxy-Q-Q-alkyl, Cι-C4-Alkylsulfonyl, Di(Q- C4-alkyl)aminosulfonyl, Cj-Q-Alkylcarbonyl oder für jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht, R39 für Wasserstoff, Halogen, Ci-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R40 für Wasserstoff, Halogen, Cyano, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R41 für Wasserstoff, Halogen, Ci-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, mit der Maßgabe, dass R40 nicht für Trifluormethyl steht, oder A für den Rest der Formel (A 17)(A16) is in which R 38 for hydrogen, cyano, Ci-Q-alkyl, Cι-C 4 haloalkyl with 1 to 5 halogen atoms, QQ-alkoxy-QQ-alkyl, hydroxy-QQ-alkyl, Cι-C 4 alkylsulfonyl, di (Q- C 4 -alkyl) aminosulfonyl, Cj-Q-alkylcarbonyl or represents optionally substituted phenylsulfonyl or benzoyl, R 39 represents hydrogen, halogen, Ci-Q-alkyl or QQ-haloalkyl having 1 to 5 halogen atoms, R 40 represents hydrogen, Halogen, cyano, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, R 41 stands for hydrogen, halogen, Ci-Q-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, with the proviso that R 40 does not represent Trifluoromethyl, or A represents the rest of the formula (A 17)
(AI 7) steht, in welcher R4" für Q-Q-Alkyl steht. 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, be- liebige Mischungen dieser Isomeren, sowie die möglichen tautomeren Formen beansprucht.(AI 7) is in which R 4 "stands for QQ-alkyl. The compounds of the invention can optionally be used as mixtures of various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers are present. Both the E and the Z isomers, as well as the threo- and erythro- as well as the optical isomers, any mixtures of these isomers and the possible tautomeric forms are claimed.
Weiterhin wurde gefunden, dass man Isopentylcarboxanilide der Formel (I) erhält, indem man a) Carbonsäure-Derivate der Formel (H) in welcher A die oben angegebenen Bedeutungen hat und X1 für Halogen oder Hydroxy steht, mit einem Anilin-Derivat der Formel (IU)It has furthermore been found that isopentylcarboxanilides of the formula (I) are obtained by a) carboxylic acid derivatives of the formula (H) in which A has the meanings given above and X 1 represents halogen or hydroxy, with an aniline derivative of the formula (IU)
in welcher L, R1 und R3 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder b) Isopentylcarboxanilide der Formel (I-a) in which L, R 1 and R 3 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or b) isopentylcarboxanilides of the formula (Ia)
in welcher L, A und R3 die oben angegebenen Bedeutungen haben mit Halogeniden der Formel (TV) R1-A_χ2 (rV) in welcher X2 für Chlor, Brom oder lod steht, R'"A für Q-Q-Alkyl, Q-Q-Alkylsulfinyl, Q-Q-Alkylsulfonyl, Q-Q-Alkoxy-Q-Q- alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halo- genalkylsulfinyl, Q-Q-Halogenalkylsulfonyl, Halogen-Q-Q-alkoxy-Q-Q-alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-Q-Alkyl)carbonyl-Q-C3-alkyl, (Q-Q-Alkoxy)car- bonyl-Q-C3-alkyl; Halogen-(Q-C3-alkyl)carbonyl-CrC3-alkyl, Halogen-(Q-Q~ alkoxy)carbonyl-Cι-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-C8-Alkyι)carbonyl, (Q -C8-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)carbo- nyl, (C3-C8-Cycloalkyl)carbonyl; (C1-C6-Halogenalkyl)carbonyl, (Q-Q-Halogen- alkoxy)carbonyl, (Halogen-Cι-C4-alkoxy-Cι-C -alkyl)carbonyl, (Q-Q-Halogen- cycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=0)R4, CONR5R6 oder -CH2NR7R8 steht, wobei R4, R5, R6, R7 und R8 die oben angegebenen Bedeutungen haben, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt, oder c) Isopenton-Derivate der Formel (V) in which L, A and R 3 have the meanings given above with halides of the formula (TV) R 1-A_ χ 2 (rV ) in which X 2 represents chlorine, bromine or iodine, R '"A represents QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfinyl, QQ-haloalkylsulfonyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halogenocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QQ-alkyl) carbonyl-Q-C3-alkyl, (QQ-alkoxy) carbonyl-QC 3 -alkyl; Halogen (QC 3 alkyl) carbonyl-CrC 3 alkyl, halogen (QQ ~ alkoxy) carbonyl-C 3 -C 3 alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (QC 8 -alkyl) carbonyl, (Q -C 8 alkoxy) carbonyl, (QQ-alkoxy-QQ-alkyl) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (C 1 -C 6 haloalkyl) carbonyl, (QQ-halogeno-alkoxy) carbonyl, (halogen-C 4 -C 4 alkoxy-C 1 -C 6 -alkyl) carbonyl, (QQ-halogeno-cycloalkyl) carbonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= 0) R 4 , CONR 5 R 6 or -CH 2 NR 7 R 8 , where R 4 , R 5 , R 6 , R 7 and R 8 have the meanings given above, in the presence of a base and in the presence of a diluent, or c) isopentone derivatives of the formula (V)
in welcher R1, R2, R3 und A die oben angegebenen Bedeutungen haben, mit Hydrazin (oder Hydrazin-hydrat) in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder d) Isopenten-Derivate der Formel (VI) in which R 1 , R 2 , R 3 and A have the meanings given above, with hydrazine (or hydrazine hydrate) in the presence of a base and optionally in the presence of a diluent, or d) isopentene derivatives of the formula (VI)
in welcher R1, R2, R3 und A die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators hydriert, oder e) Isopentin-Derivate der Formel (VH) in welcher R1, R2, R3 und A die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators hydriert. in which R 1 , R 2 , R 3 and A have the meanings given above, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst, or e) isopentine derivatives of the formula (VH) in which R 1 , R 2 , R 3 and A have the meanings given above, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst.
Schließlich wurde gefunden, dass die neuen Isopentylcarboxanilide der Formel (I) sehr gute mikrobizide Eigenschaften besitzen und zur Bekämpfung unerwünschter Mikroorganismen sowohl im Pflanzenschutz als auch im Materialschutz verwendbar sind.Finally, it was found that the new isopentylcarboxanilides of the formula (I) have very good microbicidal properties and can be used to control unwanted microorganisms both in crop protection and in material protection.
Die erfmdungsgemäßen Isopentylcarboxanilide 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.Formula (I) generally defines the isopentylcarboxanilides according to the invention. Preferred radical definitions of the formulas mentioned above and below are given below. These definitions apply equally to the end products of the formula (I) and to all intermediates.
L steht bevorzugt für L-l, wobei R2 jeweils die allgemeinen, bevorzugten, besonders bevorzugten, ganz besonders bevorzugten oder insbesondere bevorzugten Bedeutungen haben kann. L steht außerdem bevorzugt für L-2.L preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings. L also preferably represents L-2.
L steht außerdem bevorzugt für L-3. L steht außerdem bevorzugt für L-4.L also preferably represents L-3. L also preferably represents L-4.
L steht besonders bevorzugt für L-l, wobei R2 jeweils die allgemeinen, bevorzugten, besonders bevorzugten, ganz besonders bevorzugten oder insbesondere bevorzugten Bedeutungen haben kann. L steht außerdem besonders bevorzugt für L-2. L steht ganz besonders bevorzugt für L-l, wobei R2 jeweils die allgemeinen, bevorzugten, besonders bevorzugten, ganz besonders bevorzugten oder insbesondere bevorzugten Bedeutungen haben kann.L particularly preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings. L is also particularly preferably L-2. L very particularly preferably represents L 1 , where R 2 can each have the general, preferred, particularly preferred, very particularly preferred or particularly preferred meanings.
R1 steht bevorzugt für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkylsulfmyl, Q-Q-Alkylsulfonyl, Q- Q-Alkoxy-Q-Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q- Q-Halogenalkylsulfinyl, CrQ-Halogenalkylsulfonyl, Halogen-Q-Q-alkoxy-Q-Q-alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-Q-Alky carbonyl-Q-Q-alkyl, (Q-Q-Alkoxy)carbonyl-Q-Q- alkyl; Halogen-(Q-Q-alkyl)carbonyl-Q-C3-alkyl, Halogen-(Cι-C3-alkoxy)carbonyl-Q-Q- alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-C6-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Cι-C3-Alkoxy-Cι-C3-alkyl)carbonyl, (Q- C6-Cycloalkyl)carbonyl; (C C4-Halogenalkyl)carbonyl, (Q-Q-Halogenalkoxy)carbonyl, (Ηalogen-Q-Q-alkoxy-Q-Q-alkyι)carborryl, (Q-Q-HalogencycloalkyTjcarbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, -CONR5R6 oder -CH2NR7R8.R 1 preferably represents hydrogen, QQ-alkyl, QQ-alkylsulfmyl, QQ-alkylsulfonyl, Q-Q-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, Q-Q-haloalkylsulfinyl, CrQ-haloalkylsulfonyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QQ-alkycarbonyl-QQ-alkyl, (QQ-alkoxy) carbonyl-QQ- alkyl; Halogen (QQ-alkyl) carbonyl-QC 3 -alkyl, halogen (-C-C 3 -alkoxy) carbonyl-QQ-alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (QC 6 alkyl) carbonyl, (QQ alkoxy) carbonyl, (C 1 -C 3 alkoxy C 1 -C 3 alkyl) carbonyl, (Q C 6 cycloalkyl) carbonyl; (CC 4 -haloalkyl) carbonyl, (QQ-haloalkoxy) carbonyl, (Ηalogen-QQ-alkoxy-QQ-alkyι) carborryl, (QQ-halocycloalkyTjcarbonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 4 , -CONR 5 R 6 or -CH 2 NR 7 R 8 .
R1 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propyl- sulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Tri- fluorethyl, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethyl- sulfinyl, Trifluormethylsulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CHCCH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-C02CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2)2-CO-CH2CF3, -(CH2)2-CO-CH2CCl3, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2)2-C02CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CCl3, -(CH2)2-CO2CCl2CCl3; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Bxitoxycarbonyl, Cyclopropylcarbonyl; Trifluorme- thylcarbonyl, Trifluormethoxycarbonyl, oder -C(=O)C(=O)R5, -CONRV oder -CH2NR8R9. R1 steht ganz besonders bevorzugt für "Wasserstoff, Methyl, Methoxymethyl, Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=O)C(=0)CH3, -C(=O)C(=O)CH2OCH3, -C(=O)CO2CH3, -C(=O)CO2CH2CH3.R 1 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, Trifluoromethyl, trichloromethyl, trifluoromethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , - (CH 2 ) 2 -CO-CH 3 , - (CH 2 ) 2 -CO-CH 2 CH 3 , - (CH 2 ) 2 -CO-CHCCH 3 ) 2 , -CH 2 -CO 2 CH 3 , - CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH 3 ) 2 , - (CH 2 ) 2 -C0 2 CH 3 , - (CH 2 ) 2 -CO 2 CH 2 CH 3 , - (CH 2 ) 2 -CO 2 CH (CH 3 ) 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 , -CH 2 -CO- CH 2 CCl 3 , - (CH 2 ) 2 -CO-CH 2 CF 3 , - (CH 2 ) 2 -CO-CH 2 CCl 3 , -CH 2 -CO 2 CH 2 CF 3 , -CH 2 -CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCl 2 CCl 3 , - (CH 2 ) 2 -C0 2 CH 2 CF 3 , - (CH 2 ) 2 -CO 2 CF 2 CF 3 , - (CH 2 ) 2 -CO 2 CH 2 CCl 3 , - (CH 2 ) 2 -CO 2 CCl 2 CCl 3 ; Methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-Bxitoxycarbonyl, cyclopropylcarbonyl; Trifluoromethylcarbonyl, Trifluormethoxycarbonyl, or -C (= O) C (= O) R 5 , -CONRV or -CH 2 NR 8 R 9 . R 1 very particularly preferably represents " hydrogen, methyl, methoxymethyl, formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , -C (= O) CHO, -C (= O) C (= 0) CH 3 , -C (= O) C (= O) CH 2 OCH 3 , -C (= O) CO 2 CH 3 , -C (= O) CO 2 CH 2 CH 3 .
R2 steht bevorzugt für Wasserstoff.R 2 preferably represents hydrogen.
R2 steht außerdem bevorzugt für Fluor, wobei Fluor besonders bevorzugt in 4-, 5- oder 6- Position, ganz besonders bevorzugt in 4- oder 6-Position, insbesondere in 4-Position des Anilidrestes steht [vgl. oben Formel (I)].R 2 also preferably represents fluorine, fluorine being particularly preferably in the 4-, 5- or 6-position, very particularly preferably in the 4- or 6-position, in particular in the 4-position of the anilide radical [cf. formula (I) above].
R2 steht außerdem bevorzugt für Chlor, wobei Chlor besonders bevorzugt in 5-Position des Anilidrestes steht [vgl. oben Formel (I)]. Chlor steht außerdem besonders bevorzugt in 4-Po- sition des Anilidrestes. R2 steht außerdem bevorzugt für Methyl, wobei Methyl besonders bevorzugt in 3-Position des Anilidrestes steht [vgl. oben Formel (I)]. R2 steht außerdem bevorzugt für Trifluormethyl, wobei Trifluormethyl besonders bevorzugt in 4- oder 5-Position des Anilidrestes steht [vgl. oben Formel (I)].R 2 also preferably represents chlorine, chlorine being particularly preferably in the 5-position of the anilide residue [cf. formula (I) above]. Chlorine is also particularly preferably in the 4-position of the anilide residue. R 2 also preferably represents methyl, methyl being particularly preferably in the 3-position of the anilide radical [cf. formula (I) above]. R 2 also preferably stands for trifluoromethyl, trifluoromethyl being particularly preferably in the 4- or 5-position of the anilide residue [cf. formula (I) above].
R3 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Q-Q-Alkyl, Q-Q-Halogenalkyl mit 1 bis 13 Fluor-, Chlor- und/oder Bromatomen. R3 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, n-, iso-Propyl, n-, iso-, sec-, tert-Butyl oder Q-C4-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen.R 3 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, QQ-alkyl, QQ-haloalkyl with 1 to 13 fluorine, chlorine and / or bromine atoms. R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl or QC 4 -haloalkyl with 1 to 9 fluorine, chlorine - and / or bromine atoms.
R3 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Methyl, Ethyl oder Trifluormethyl.R 3 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl or trifluoromethyl.
R4 steht bevorzugt für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Alkoxy-Q-Q-alkyl, Q- Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy, Halogen-Q-Q-alkoxy-Q-Q- alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R4 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, tert-Butyl, Methoxy, Ethoxy, n- oder iso-Propoxy, tert-Butoxy, Cyclopropyl; Trifluormethyl, Trifluor- methoxy.R 4 preferably represents hydrogen, QQ-alkyl, QQ-alkoxy, QQ-alkoxy-QQ-alkyl, Q-Q-cycloalkyl; QQ-haloalkyl, QQ-haloalkoxy, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms. R 4 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, n- or iso-propoxy, tert-butoxy, cyclopropyl; Trifluoromethyl, trifluoromethoxy.
R5 und R6 stehen unabhängig voneinander bevorzugt für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkoxy-Q- Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Halogen-Q-Q-alkoxy-Q-Q-alkyl, Q-Q- Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R5 und R6 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Q- Q-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR9 enthalten kann. R5 und R6 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopenτyl, Cyclohexyl; Trifluormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxymethyl. R5 und R bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R9 substituiert sein kann.R 5 and R 6 independently of one another preferably represent hydrogen, QQ-alkyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QQ-haloalkyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms. R 5 and R 6 , together with the nitrogen atom to which they are attached, preferably form a saturated heterocycle with 5 to 8 ring atoms, which is optionally monosubstituted to tetrasubstituted, identically or differently, by halogen or Q-Q-alkyl, the heterocycle 1 or 2 further, non-neighboring heteroatoms from the series oxygen, sulfur or NR 9 can contain. R 5 and R 6 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl. R 5 and R, together with the nitrogen atom to which they are attached, particularly preferably form a saturated heterocycle from the morpholine series which may be monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine or methyl, Thiomorpholine or piperazine, where the piperazine on the second nitrogen atom can be substituted by R 9 .
R7 und R8 stehen unabhängig voneinander bevorzugt für Wasserstoff, Q-Q-Alkyl, C3-C6-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen. R7 und R8 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, bevorzugt einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q- Q-Alkyl substituierten gesättigten Heterocyclus mit 5 bis 8 Ringatomen, wobei der Heterocyclus 1 oder 2 weitere, nicht benachbarte Heteroatome aus der Reihe Sauerstoff, Schwefel oder NR9 enthalten kann. R7 und R8 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl; Trifluormethyl, Trichlormethyl, Trifluorethyl, Trifluormethoxymethyl.R 7 and R 8 independently of one another preferably represent hydrogen, QQ-alkyl, C 3 -C 6 -cycloalkyl; QQ-haloalkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms. R 7 and R 8 , together with the nitrogen atom to which they are attached, preferably form a saturated heterocycle having 5 to 8 ring atoms, which may be mono- or polysubstituted, identically or differently, by halogen or Q-Q-alkyl, the heterocycle 1 or 2 further, non-neighboring heteroatoms from the series oxygen, sulfur or NR 9 can contain. R 7 and R 8 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl ; Trifluoromethyl, trichloromethyl, trifluoroethyl, trifluoromethoxymethyl.
R7 und R8 bilden außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, besonders bevorzugt einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Fluor, Chlor, Brom oder Methyl substituierten gesättigten Heterocyclus aus der Reihe Morpholin, Thiomorpholin oder Piperazin, wobei das Piperazin am zweiten Stickstoffatom durch R9 sub- stituiert sein kann.R 7 and R 8 , together with the nitrogen atom to which they are attached, particularly preferably form a saturated heterocycle from the series morpholine, thiomorpholine or piperazine, which is optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine or methyl, where the piperazine on the second nitrogen atom can be substituted by R 9 .
R9 steht bevorzugt für Wasserstoff oder Q-C4-Alkyl.R 9 preferably represents hydrogen or QC 4 alkyl.
R9 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl.R 9 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
A steht bevorzugt für einen der oben angegebenen Reste AI, A2, A3, A4, A5, A6, A9, A10, All, A12, A13, A14, A15 oder A16.A preferably represents one of the radicals A1, A2, A3, A4, A5, A6, A9, A10, All, A12, A13, A14, A15 or A16.
A steht besonders bevorzugt für einen der oben angegebenen Reste AI, A2, A4, A5, A6, A9, All, A12, AI 3, A14, AI 5 oder AI 6. A steht ganz besonders bevorzugt für den Rest A 1.A particularly preferably represents one of the radicals A1, A2, A4, A5, A6, A9, All, A12, AI 3, A14, AI 5 or AI 6 indicated above. A very particularly preferably represents the radical A 1.
A steht außerdem ganz besonders bevorzugt für den Rest A2.A is also very particularly preferably the radical A2.
A steht außerdem ganz besonders bevorzugt für den Rest A4.A also particularly preferably stands for the rest A4.
A steht außerdem ganz besonders bevorzugt für den Rest A5.A also particularly preferably stands for the rest A5.
A steht außerdem ganz besonders bevorzugt für den Rest A6. A steht außerdem ganz besonders bevorzugt für den Rest A9.A also very particularly preferably represents the radical A6. A also very particularly preferably represents the radical A9.
A steht außerdem ganz besonders bevorzugt für den Rest Al l. A steht außerdem ganz besonders bevorzugt für den Rest A12.A also very particularly preferably represents the rest Al 1. A also very particularly preferably represents the radical A12.
A steht außerdem ganz besonders bevorzugt für den Rest A 13.A also very particularly preferably represents the radical A 13.
A steht außerdem ganz besonders bevorzugt für den Rest A14.A also very particularly preferably represents the radical A14.
A steht außerdem ganz besonders bevorzugt für den Rest AI 6.A also very particularly preferably represents the rest of AI 6.
R10 steht bevorzugt für Wasserstoff, Hydroxy, Foπrryl, Cyano, Fluor, Chlor, Brom, lod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Cyclopropyl, Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Trifluorme- thylthio, Difluormethylthio, Aminocarbonyl, Ammocarbonylmethyl oder Aminocarbonylethyl mit der Maßgabe, dass R10 nicht für lod steht, -wenn Rn für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rπ für Wasserstoff und R12 für Methyl stehen. R10 steht besonders bevorzugt für Wasserstoff, Hydroxy, Formyl, Fluor, Chlor, Brom, lod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Monofluormethyl, Monofluorethyl, Difluor- methyl, Trifluormethyl, Difluorchlormethyl, Trichlormethyl, Dichlormethyl, Pentafluorethyl, Cyclopropyl, Methoxy, Ethoxy, Trifluormethoxy, Difluormethoxy, Trichlormethoxy, Me- thylthio, Ethylthio, Trifluormethylthio oder Difluormethylthio, mit der Maßgabe, dass R10 nicht für lod steht, Λvenn Rn für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rπ für Wasserstoff und R12 für Methyl stehen.R 10 preferably represents hydrogen, hydroxyl, foπrryl, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, QQ-haloalkyl, QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, trifluoromethylthio, difluoromethylthio, aminocarbonyl, ammocarbonylmethyl or aminocarbonylethyl with the proviso that R 10 is not iodine, if R n is hydrogen and with the proviso that R 10 is not for Trifluoromethyl or difluoromethyl is when R 3 and R π are hydrogen and R 12 is methyl. R 10 particularly preferably represents hydrogen, hydroxy, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, monofluoromethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, dichloromethyl, pentafluoroethyl, Cyclopropyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio, with the proviso that R 10 is not iodine, Λvenn R n is hydrogen, and with the proviso that R 10 is not represents trifluoromethyl or difluoromethyl when R 3 and R π are hydrogen and R 12 is methyl.
R10 steht ganz besonders bevorzugt für Wasserstoff, Hydroxy, Formyl, Fluor, Chlor, Brom, lod, Methyl, Ethyl, iso-Propyl, Methoxy, Cyclopropyl, Monofluormethyl, Monofluorethyl, Difluormethyl, Dichlormethyl, Trifluormethyl, Difluorchlormethyl, Trichlormethyl, -CHFCH3 oder Difluormethoxy, mit der Maßgabe, dass R10 nicht für lod steht, Λvenn Rπ für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rπ für Wasserstoff und R12 für Methyl stehen. R10 steht insbesondere bevorzu t für Wasserstoff, Hydroxy, Formyl, Chlor, Methyl, Ethyl, Methoxy, Cyclopropyl, Monofluormethyl, Difluormethyl, Dichlormethyl, Trifluormethyl, -CHFCH3 oder Difluormethoxy, mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rn für Wasserstoff und R12 für Methyl stehen.R 10 very particularly preferably represents hydrogen, hydroxyl, formyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, cyclopropyl, monofluoromethyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, -CHFCH 3 or difluoromethoxy, with the proviso that R 10 is not iodine, Rvenn R π is hydrogen, and with the proviso that R 10 is not trifluoromethyl or difluoromethyl when R 3 and R π are hydrogen and R 12 is methyl stand. R 10 particularly preferably represents hydrogen, hydroxyl, formyl, chlorine, methyl, ethyl, methoxy, cyclopropyl, monofluoromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, -CHFCH3 or difluoromethoxy, with the proviso that R 10 does not represent trifluoromethyl or difluoromethyl, when R 3 and R n are hydrogen and R 12 is methyl.
Rπ steht bevorzugt für Wasserstoff, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen,R π preferably represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms,
Rπ steht besonders bevorzugt für Wasserstoff, Chlor, Brom, lod, Methyl oder -CHFCH3. R1 ' steht ganz besonders bevorzugt für Wasserstoff, Chlor, Methyl oder -CHFCH3.R π particularly preferably represents hydrogen, chlorine, bromine, iodine, methyl or -CHFCH 3 . R 1 'very particularly preferably represents hydrogen, chlorine, methyl or -CHFCH 3 .
R12 steht bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl oder Phenyl.R 12 preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl.
R12 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, iso-Propyl, Trifluormethyl, Difluormethyl, Hydroxymethyl, Hydroxyethyl oder Phenyl.R 12 particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.
R12 steht ganz besonders bevorzugt für Wasserstoff, Methyl, Trifluormethyl oder Phenyl.R 12 very particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.
R12 steht insbesondere bevorzugt für Methyl.R 12 particularly preferably represents methyl.
R13 und R14 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 13 and R 14 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R13 und R14 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl. R13 und R14 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl oder Trichlormethyl.R 13 and R 14 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl. R 13 and R 14 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.
R13 und R14 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 13 and R 14 particularly preferably each represent hydrogen.
R1S steht bevorzugt für Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, Q-Q-Halogenalkyl oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 1S preferably represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms.
R15 steht besonders bevorzugt für Fluor, Chlor, Brom, lod, Cyano, Methyl, Trifluormethyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy. R15 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, lod, Methyl, Trifluormethyl oder Trifluormethoxy. R15 steht insbesondere bevorzugt für Chlor oder Methyl.R 15 particularly preferably represents fluorine, chlorine, bromine, iodine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 15 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy. R 15 particularly preferably represents chlorine or methyl.
R16 und R17 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 16 and R 17 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R16 und R17 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl oder Trichlormethyl.R 16 and R 17 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.
R16 und R17 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder Methyl.R 16 and R 17 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine or methyl.
R16 und R17 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 16 and R 17 particularly preferably each represent hydrogen.
R18 steht bevorzugt für Wasserstoff, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R18 steht besonders bevorzugt für Wasserstoff, Methyl oder Trifluormethyl. R18 steht ganz besonders bevorzugt für Methyl.R 18 preferably represents hydrogen, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 18 particularly preferably represents hydrogen, methyl or trifluoromethyl. R 18 very particularly preferably represents methyl.
R19 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Q-Q-Alkyl, Q- Q-Halogenalkyl, Q-Q-Halogenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen. R19 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Difluormethyl, Trifluormethyl, Difluorchlormethyl, Trichlormethyl, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Trifluormethylthio, Difluormethylthio, Difluorchlor- methylthio oder Trichlormethylthio. R19 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Difluormethyl, Trifluormethyl oder Trichlormethyl. R19 steht insbesondere bevorzugt für lod, Methyl, Difluormethyl oder Trifluormethyl.R 19 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, Q-Q-haloalkyl, QQ-haloalkoxy or QQ-haloalkylthio, each with 1 to 5 fluorine, chlorine and / or bromine atoms. R 19 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, difluoromethyl, Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio or trichloromethylthio. R 19 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl. R 19 particularly preferably represents iodine, methyl, difluoromethyl or trifluoromethyl.
R20 steht bevorzugt für Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Q-Q-Halogenalkyl oder Q- Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und oder Bromatomen. R20 steht besonders bevorzugt für Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Methyl, Ethyl, n- Propyl, iso-Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy oder Trichlormethoxy. R20 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, lod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 20 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QQ-haloalkyl or Q-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and or bromine atoms. R 20 particularly preferably represents fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, Difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy. R 20 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R21 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Q-Q-Halogenalkyl oder Ci-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Q-Q-Alkylsulfϊnyl oder Q-Q-Alkylsulfonyl. R21 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl, Trichlormethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Trifluormethoxy, Difluormethoxy, Difluorchlormethoxy, Trichlormethoxy, Methylsulfinyl oder Methylsulfonyl. R21 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, n-Propyl, iso- Propyl, n-Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Trichlormethyl, Methylsulfinyl oder Methylsulfonyl. R21 steht insbesondere bevorzugt für Wasserstoff.R 21 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl or Ci-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms , QQ-Alkylsulfϊnyl or QQ-Alkylsulfonyl. R 21 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, Methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulfinyl or methylsulfonyl. R 21 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulfinyl or methylsulfonyl , R 21 particularly preferably represents hydrogen.
R22 steht bevorzugt für Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R22 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 22 preferably represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 22 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R22 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 22 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R23 steht bevorzugt für Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R23 steht besonders bevorzugt für Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R23 steht ganz besonders bevorzugt für Methyl, Trifluormethyl, Difluormethyl oder Trichlor- methyl.R 23 preferably represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 23 particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 23 very particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R24 und R25 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 24 and R 25 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R24 und R25 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 24 and R 25 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R24 und R25 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder Methyl.R 24 and R 25 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine or methyl.
R24 und R25 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 24 and R 25 particularly preferably each represent hydrogen.
R26 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 26 preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R26 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R26 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Trifluormethyl.R 26 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 26 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R26 steht insbesondere bevorzugt für Methyl oder Trifluormethyl.R 26 particularly preferably represents methyl or trifluoromethyl.
R27 und R28 stehen unabhängig voneinander bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R27 und R28 stehen unabhängig voneinander besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Nitro, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 27 and R 28 independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 27 and R 28 independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R27 und R28 stehen unabhängig voneinander ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 27 and R 28 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R27 und R28 stehen insbesondere bevorzugt jeweils für Wasserstoff.R 27 and R 28 particularly preferably each represent hydrogen.
R29 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Q-C2-Halogenalkyl mit 1 bis 5 Fluor, Chlor und oder Bromatomen. R29 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R29 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R29 steht insbesondere bevorzugt für Methyl.R 29 preferably represents fluorine, chlorine, bromine, methyl, ethyl or QC 2 haloalkyl with 1 to 5 fluorine, chlorine and or bromine atoms. R 29 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 29 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 29 particularly preferably represents methyl.
R30 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Ci-Q-Alkylamino, Di(Q-Q- alkyl)amino, Cyano, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 30 preferably represents hydrogen, fluorine, chlorine, bromine, amino, Ci-Q-alkylamino, di (QQ-alkyl) amino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R30 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dime- thylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 30 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R30 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R30 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oder Tri- fluormethyl.R 30 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 30 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
R31 steht bevorzugt für Fluor, Chlor, Brom, Hydroxy, Methyl, Ethyl, Methoxy, Ethoxy, Cyclopropyl, Q-Q-Halogenalkyl oder Q-Q-Halogenalkoxy mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R31 steht besonders bevorzugt für Fluor, Chlor, Brom, Hydroxy, Methyl, Ethyl, Methoxy, Ethoxy, Cyclopropyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl. R31 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Hydroxy, Methyl, Methoxy, Cyclopropyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R32 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Cι-C -Alkylamino, Di(Q-Q- alkyl)amino, Cyano, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R32 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Cyano, Methyl, Ethyl, Trifluormethyl, Difluoimethyl, Difluorchlormethyl oder Trichlormethyl. R32 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Amino, Methylamino, Dimethylamino, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R32 steht insbesondere bevorzugt für Amino, Methylamino, Dimethylamino, Methyl oder Trifluormethyl.R 31 preferably represents fluorine, chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, QQ-haloalkyl or QQ-haloalkoxy with 1 to 5 fluorine, chlorine and / or bromine atoms. R 31 particularly preferably represents fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxy, ethoxy, cyclopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 31 very particularly preferably represents fluorine, chlorine, bromine, hydroxy, methyl, methoxy, cyclopropyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 32 preferably represents hydrogen, fluorine, chlorine, bromine, amino, -CC alkylamino, di (QQ-alkyl) amino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 32 particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl. R 32 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 32 particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.
R33 steht bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R33 steht besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 33 preferably represents fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 33 particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R33 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R33 steht insbesondere bevorzugt für Methyl, Trifluormethyl oder Difluormethyl.R 33 very particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 33 particularly preferably represents methyl, trifluoromethyl or difluoromethyl.
R steht bevorzugt für Wasserstoff, Methyl oder Ethyl.R preferably represents hydrogen, methyl or ethyl.
R >3 steht besonders bevorzugt für Methyl.R> 3 particularly preferably represents methyl.
R35 steht bevorzugt für Fluor, Chlor, Brom, Methyl oder Ethyl. R35 steht besonders bevorzugt für Fluor, Chlor oder Methyl.R 35 preferably represents fluorine, chlorine, bromine, methyl or ethyl. R 35 particularly preferably represents fluorine, chlorine or methyl.
R36 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R36 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl oder Trifluormethyl.R 36 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 36 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.
R37 steht bevorzugt für Fluor, Chlor, Brom, lod, Hydroxy, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Q-C2-Halogenalkyl oder Q- Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen.R 37 preferably represents fluorine, chlorine, bromine, iodine, hydroxy, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QC 2 -haloalkyl or Q-Q-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms.
R37 steht besonders bevorzugt für Fluor, Chlor, Brom, lod, Methyl, Ethyl, n-Propyl, iso-Propyl, n- Butyl, iso-Butyl, sec-Butyl, tert-Butyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl, Trichlormethyl. R37 steht ganz besonders bevorzugt für Fluor, Chlor, Brom, lod, Methyl, Trifluormethyl, Difluormethyl oder Trichlormethyl.R 37 particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl. R 37 very particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.
R38 steht bevorzugt für Wasserstoff, Methyl, Ethyl, Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, Q-Q-Alkoxy-Q-Q-alkyl, Hydroxymethyl, Hydroxyethyl, Methylsulfonyl oder Dimethylaminosulfonyl.R 38 preferably represents hydrogen, methyl, ethyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, QQ-alkoxy-QQ-alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl.
R38 steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, Trifluormethyl, Methoxymethyl, Ethoxymethyl, Hydroxymethyl oder Hydroxyethyl.R 38 particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl.
R38 steht ganz besonders bevorzugt für Methyl oder Methoxymethyl.R 38 very particularly preferably represents methyl or methoxymethyl.
R39 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen.R 39 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms.
R39 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl, Trifluormethyl, Difluormethyl oder Trichlormethyl. R39 steht ganz besonders bevorzugt für Wasserstoff oder Methyl.R 39 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl. R 39 very particularly preferably represents hydrogen or methyl.
R40 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso-Propyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen. R40 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso- Propyl, Trifluormethyl, Difluormethyl, Difluorchlormethyl oder Trichlormethyl.R 40 preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 40 particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.
R40 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Methyl oder Trifluormethyl.R 40 very particularly preferably represents hydrogen, fluorine, methyl or trifluoromethyl.
R41 steht bevorzugt für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen. R41 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl oder Trifluormethyl. R41 steht ganz besonders bevorzugt für Wasserstoff oder Trifluormethyl.R 41 preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms. R 41 particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl. R 41 very particularly preferably represents hydrogen or trifluoromethyl.
R42 steht bevorzugt für Methyl, Ethyl, n-Propyl oder iso-Propyl. R42 steht besonders bevorzugt Methyl oder Ethyl.R 42 preferably represents methyl, ethyl, n-propyl or isopropyl. R 42 is particularly preferably methyl or ethyl.
Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-l steht, wobei R2 die oben angegebenen allgemeinen Bedeutungen hat.Compounds of the formula (I) in which L represents L 1 are emphasized, where R 2 has the general meanings given above.
Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-l steht, wobei R2 die oben angegebenen bevorzugten Bedeutungen hat. Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-l steht, wobei R2 die oben angegebenen besonders bevorzugten Bedeutungen hat.Compounds of the formula (I) in which L represents L 1 are emphasized, where R 2 has the preferred meanings indicated above. Compounds of the formula (I) in which L represents L 1 are emphasized, where R 2 has the particularly preferred meanings given above.
Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-l steht, wobei R2 die oben angegebenen ganz besonders bevorzugten Bedeutungen hat. Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-l steht, wobei R2 die oben angegebenen insbesondere bevorzugten Bedeutungen hat.Compounds of the formula (I) in which L represents L1 are emphasized, where R 2 has the very particularly preferred meanings given above. Compounds of the formula (I) in which L represents L 1 are emphasized, where R 2 has the particularly preferred meanings given above.
Hervorgehoben sind Verbindungen der Formel (I), in welcher L für L-2 steht.Compounds of the formula (I) in which L represents L-2 are emphasized.
Hervorgehoben sind Verbindungen der Formel (I), in welcher R1 für Wasserstoff steht.Compounds of the formula (I) in which R 1 represents hydrogen are emphasized.
Hervorgehoben sind Verbindungen der Formel (I), in welcher R1 für Formyl steht. Hervorgehoben sind außerdem Verbindungen der Formel (I), in welcher R1 für -C(=0)C(=O)R4 steht, wobei R4 die oben angegebenen Bedeutungen hat.Compounds of formula (I) in which R 1 stands for formyl are emphasized. Also emphasized are compounds of the formula (I) in which R 1 represents -C (= 0) C (= O) R 4 , where R 4 has the meanings given above.
Hervorgehoben sind Verbindungen der Formel (I), in welcher A für AI steht.Compounds of formula (I) in which A stands for AI are emphasized.
Hervorgehoben sind Verbindungen der Formel (I), in welcher R3 für Wasserstoff steht.Compounds of the formula (I) in which R 3 represents hydrogen are emphasized.
Hervorgehoben sind Verbindungen der Formel (I), in welcher R3 für Halogen, bevorzugt für Fluor, Chlor, Brom oder lod, besonders bevorzugt für Fluor, Chlor oder Brom, ganz besonders bevorzugt fürCompounds of the formula (I) are emphasized in which R 3 is halogen, preferably fluorine, chlorine, bromine or iodine, particularly preferably fluorine, chlorine or bromine, very particularly preferably for
Fluor oder Chlor steht.Fluorine or chlorine.
Hervorgehoben sind Verbindungen der Formel (I), in welcher R3 für Q-Q-Alkyl, bevorzugt fürCompounds of formula (I) are emphasized in which R 3 is for QQ-alkyl, preferably for
Q-Q-Alkyl, besonders bevorzugt für Methyl, Ethyl, n-, iso-Propyl, n-, iso-, sec- oder tert-Butyl, ganz besonders bevorzugt für Methyl oder Ethyl steht. Hervorgehoben sind Verbindungen der Formel (I), in welcher R3 für Q-Q-Halogenalkyl, bevorzugt für Q-Q-Halogenalkyl mit 1 bis 13 Fluor-, Chlor- und/oder Bromatomen, besonders bevorzugt für Q-Q-Halogenalkyl mit 1 bis 9 Fluor-, Chlor- und/oder Bromatomen, ganz besonders bevorzugt für Trifluormethyl steht.QQ-alkyl, particularly preferably methyl, ethyl, n-, iso-propyl, n-, iso-, sec- or tert-butyl, very particularly preferably methyl or ethyl. Compounds of the formula (I) are emphasized in which R 3 for QQ-haloalkyl, preferably for QQ-haloalkyl with 1 to 13 fluorine, chlorine and / or bromine atoms, particularly preferably for QQ-haloalkyl with 1 to 9 fluorine, Chlorine and / or bromine atoms, very particularly preferably represents trifluoromethyl.
Gesättigte oder ungesättigte Kohlenwasserstoffteste wie Alkyl oder Alkenyl können, auch in Verbindung mit Heteroatomen, wie z.B. in Alkoxy, soweit möglich, jeweils geradkettig oder verzweigt sein.Saturated or unsaturated hydrocarbon tests such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
Gegebenenfalls substituierte Reste können einfach oder mehrfach substituiert sein, wobei bei Mehrfachsubstitutionen die Substituenten gleich oder verschieden sein können.Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
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 lod, insbesondere für Fluor, Chlor und Brom.Halogen substituted residues such as e.g. Haloalkyl, are halogenated once or several times. In the case of multiple halogenation, the halogen atoms can be the same or different. Halogen stands for fluorine, chlorine, bromine and iodine, in particular for 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.The general definitions or explanations of residues or explanations listed above or in preferred areas can, however, also be used with one another, ie between the respective areas and Preferred areas can be combined as desired. They apply accordingly to the end products as well as to the preliminary and intermediate products.
Die genannten Definitionen können untereinander in beliebiger Weise kombiniert werden. Außerdem können auch einzelne Definitionen entfallen.The definitions mentioned can be combined with one another in any way. In addition, individual definitions can also be omitted.
Bevorzugt, besonders bevorzugt oder ganz besonders bevorzugt sind Verbindungen der Formel (I), welche jeweils die unter bevorzugt, besonders bevorzugt oder ganz besonders bevorzugt genannten Substituenten tragen.Preferred, particularly preferred or very particularly preferred are compounds of the formula (I) which each carry the substituents mentioned under preferred, particularly preferred or very particularly preferred.
Beschreibung der erfindungsgemäßen Verfahren zum Herstellen der Isopentylcarboxanilide der Formel (T) sowie der ZwischenprodukteDescription of the processes according to the invention for producing the isopentylcarboxanilides of the formula (T) and the intermediates
Verfahren (a) Verwendet man 5-Fluor-l,3-dimethyl-lH-pyrazol-4-carbonyl-chlorid und [2-(3-Methylbutyl)phenyl]- amin als Ausgangsstoffe, so kann das erfindungsgemäße Verfahren (a) durch das folgende Formelschema veranschaulicht werden:Process (a) If 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and [2- (3-methylbutyl) phenyl] amine are used as starting materials, process (a) according to the invention can be carried out by the following formula scheme can be illustrated:
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe benötigten Carbonsäure-Derivate sind durch die Formel (π) allgemein definiert. In dieser Formel (H) hat A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für A angegeben wurden. X1 steht bevorzugt für Chlor, Brom oder Hydroxy.Formula (π) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out process (a) according to the invention. In this formula (H), A has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for A in connection with the description of the compounds of the formula (I) according to the invention. X 1 preferably represents chlorine, bromine or hydroxy.
Die Carbonsäure-Derivate der Formel (11) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen (vgl. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 und EP-A 0 589 313).The carboxylic acid derivatives of the formula (11) are known and / or can be prepared by known processes (cf. WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313).
Die zur Durchführung des erfindungsgemäßen Verfahrens (a) als Ausgangsstoffe weiterhin benötig- ten Anilin-Derivate sind durch die Formel (10) allgemein definiert. In dieser Formel (IH) haben L, R1 und R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) für diese Reste als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt angegeben wurden.Formula (10) provides a general definition of the aniline derivatives which are further required as starting materials for carrying out process (a) according to the invention. In this formula (IH), L, R 1 and R 3 have preferred, particularly preferably or very particularly preferably those meanings which have already occurred in connection with the description of the compounds of the formula according to the invention (I) for these radicals as preferred, particularly preferred or very particularly preferred.
Die Anilin-Derivate der Formel (IQ), in denen L für L-l steht, sind teilweise neu. Anilin-Derivate der Formel (Uf), in denen L für L-l steht, lassen sich herstellen, indem man, f) Cyanoaniline der Formel (V i)The aniline derivatives of the formula (IQ), in which L stands for L-1, are partly new. Aniline derivatives of the formula (Uf) in which L is L-1 can be prepared by, f) cyanoanilines of the formula (V i)
in welcher R1 und R2 die oben angegebenen Bedeutungen haben, in einem ersten Schritt mit einem Grignard-Reagenz der Formel (IX) X3Mg PP. OK) H3C CH, in welcher R3 die oben angegebenen Bedeutungen hat, X3 für Chlor, Brom oder lod steht, gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt und die so erhaltenen Alkanonaniline der Formel (X) in which R 1 and R 2 have the meanings given above, in a first step with a Grignard reagent of the formula (IX) X 3 Mg PP. OK) H 3 C CH, in which R 3 has the meanings given above, X 3 represents chlorine, bromine or iodine, if appropriate in the presence of a diluent, and the alkanonanilines of the formula (X) thus obtained
in welcher R1, R2 und R3 die oben angegebenen Bedeutungen haben, in einem zweiten Schritt mit Hydrazin (oder Hydrazin-hydrat) in Gegenwart einer Base (z.B. Alkali- oder Erdalkalimetallhydroxide wie Natriumhydroxid oder Kaliumhydroxid) und ge- gebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. in which R 1 , R 2 and R 3 have the meanings given above, in a second step with hydrazine (or hydrazine hydrate) in the presence of a base (for example alkali or alkaline earth metal hydroxides such as sodium hydroxide or potassium hydroxide) and, if appropriate, in the presence of a Converts diluent.
Die zur Durchführung des erfindungsgemäßen Verfahrens (f) als Ausgangsstoffe benötigten Cyanoaniline sind durch die Formel (VflT) allgemein definiert. In dieser Formel (VIH) haben R1 und R2 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (T> als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden. Die Cyanoaniline der Formel (VIII) sind bekannt und/oder lassen sich nach bekannten Verfahren herstellen. Cyanoaniline der Formel (VTfl), in welcher R1 nicht für Wasserstoff steht, können erhalten werden, indem man Cyanoaniline der Formel (V-a)The formula (VflT) provides a general definition of the cyanoanilines required as starting materials for carrying out process (f) according to the invention. In this formula (VIH), R 1 and R 2 have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (T>) as preferred, particularly preferred or very particularly preferred for these residues were specified. The cyanoanilines of the formula (VIII) are known and / or can be prepared by known processes. Cyanoanilines of the formula (VTfl) in which R 1 is not hydrogen can be obtained by using cyanoanilines of the formula (Va)
in welcher R die oben angegebenen Bedeutungen hat, mit Halogeniden der Formel (IV) D1-A v2 R —X (iv) in welcher R1_A die oben angegebenen Bedeutungen hat, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt. [Die Reaktions- bedingungen des Verfahrens (b) gelten entsprechend.] in which R has the meanings given above, with halides of the formula (IV) D 1 -A v 2 R —X (iv) in which R 1_A has the meanings given above, in the presence of a base and in the presence of a diluent. [The reaction conditions of process (b) apply accordingly.]
Die zur Durchführung des erfindungsgemäßen Verfahrens (f) als Ausgangsstoffe weiterhin benötigten Grignard-Reagenzien sind durch die Formel (IX) allgemein definiert. In dieser Formel (TX) hat R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) für diesen Rest als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt angegeben wurden. X3 steht bevorzugt für Brom.Formula (IX) provides a general definition of the Grignard reagents which are further required as starting materials for carrying out process (f) according to the invention. In this formula (TX), R 3 has preferably, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, have been indicated as preferred, particularly preferred or very particularly preferred for this radical were. X 3 preferably represents bromine.
Die Grignard-Reagenzien der Formel (TX) sind bekannt oder können nach bekannten Verfahren erhalten werden.The Grignard reagents of the formula (TX) are known or can be obtained by known processes.
Die Alkanonaniline der Formel (X), die im erfindungsgemäßen Verfahren (f) als Zwischenprodukte durchlaufen werden sind neu und ebenfalls Gegenstand dieser Anmeldung. In der Formel (X) haben die Reste R1, R2 und R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) für diese Reste als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt angegeben wurden.The alkanonanilines of the formula (X) which are run through as intermediates in process (f) according to the invention are new and likewise the subject of this application. In the formula (X), the radicals R 1 , R 2 and R 3 have preferred, particularly preferably or very particularly preferably, those meanings which are already preferred for these radicals in connection with the description of the compounds of the formula (I) according to the invention, were particularly preferred or very particularly preferably specified.
Hydrazin (oder Hydrazin-hydrat), welches ebenfalls als Reagenz im erfindungsgemäßen Verfahren (f) benötigt wird, ist eine bekannte Synthesechemikalie.Hydrazine (or hydrazine hydrate), which is also required as a reagent in process (f) according to the invention, is a known synthetic chemical.
Das erfindungsgemäße Verfahren (f) kann in verschiedenen Varianten durchgeführt werden. So ist es möglich, zunächst Cyanoaniline der Formel (V-a) zu den entsprechenden Alkanonanilinen der Formel (VTI-a) in welcher R2 und R3 die oben angegebenen Bedeutungen haben, umzusetzen, welche dann gegebenenfalls mit Halogeniden der Formel (IV) D1-A v2 R —X (iv) in welcher R1_A die oben angegebenen Bedeutungen hat, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels zu den entsprechenden Alkanonaniline der Formel (X) umgesetzt werden. [Die Reaktionsbedingungen des Verfahrens (b) gelten entsprechend.]The method (f) according to the invention can be carried out in various variants. It is thus possible first to prepare cyanoanilines of the formula (Va) to give the corresponding alkanonanilines of the formula (VTI-a) in which R 2 and R 3 have the meanings given above, which is then optionally with halides of the formula (IV) D 1 -A v 2 R —X (iv) in which R 1_A has the meanings given above, in the presence of a Base and in the presence of a diluent to the corresponding alkanonanilines of the formula (X). [The reaction conditions of process (b) apply accordingly.]
Es ist jedoch auch möglich, die Alkanonaniline der Formel (Vll-a) gemäß dem erfindungsgemäßen Verfahren (f) zu den entsprechenden Anilin-Derivaten der Formel (IQ-a)However, it is also possible to convert the alkanonanilines of the formula (VIII-a) into the corresponding aniline derivatives of the formula (IQ-a) according to process (f) according to the invention
in welcher R2 und R3 die oben angegebenen Bedeutungen haben, umzusetzen, welche dann gegebenenfalls mit Halogeniden der Formel (IV) R — x (IV) in welcher R1_A die oben angegebenen Bedeutungen hat, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels zu den entsprechenden Anilin- Derivaten der Formel (IU) umgesetzt werden. [Die Reaktionsbedingungen des Verfahrens (b) gelten entsprechend.] in which R 2 and R 3 have the meanings given above, which is then optionally with halides of the formula (IV) R - x (IV) in which R 1_A has the meanings given above, in the presence of a base and in the presence of a diluent to be converted to the corresponding aniline derivatives of the formula (IU). [The reaction conditions of process (b) apply accordingly.]
Anilin-Derivate der Formel (ITI-b)Aniline derivatives of the formula (ITI-b)
in welcher a) R1_B für Q-Q-Alkyl, Q-Q-Alkylsulfinyl, Q-C6-Alkylsulfonyl, Q-Q-Alkoxy-Q-Q- alkyl, Q-Q-Cycloalkyl; C C6-Halogenalkyl, C C4-Halogenalkylthio, Q-Q-Halo- genalkylsulfinyl, Q-Q-Halogenalkylsulfonyl, Halogen-Cι-C4-alkoxy-CrC -alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-C3-Alkyl)carbonyl-Q-Q-alkyl, (Q-Q-Alkoxy)car- bonyl-Q-C3-alkyl; Halogen-(Q-Q-alkyl)carbonyl-Q-Q-alkyl, Halogen-(Q-Q-alk- oxy)carbonyl-Q-Q-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)- carbonyl, (Q-Q-CycloalkyOcarbonyl; (Q-Q-Halogenalkyl)carbonyl, (Q-Q- Halogenalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyl)carbonyl, (Q-Q- Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=0)C(=O)R4, CONR5Rδ oder -CH2NR7R8 steht, und R3"B für Wasserstoff, Halogen, Q-Q-Alkyl, Q-Q-Halogenalkyl steht, oder b) R1_B für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkylsulfinyl, Q-Q-Alkylsulfonyl, Q-Q- Alkoxy-Q-Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halogenalkylsulfinyl, Q-Q-Halogenalkylsulfonyl, Halogen-Q-Q-alkoxy-Q- C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-C3-Alkyl)carbonyl-Q-Q-alkyl, (Q-Q- Alkoxy)carbonyl-Q-Q-alkyl; Halogen-(Q-Q-alkyι)carbonyl-Q-Q-alkyl, Halogen- (Cι-C3-alkoxy)carbonyl-Cι-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (C C8-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)carbo- nyl, (C3-C8-Cycloalkyl)carbonyl; (Cι-Q-Halogenalkyl)carbonyl, (Q-Q-Halogenalk- oxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-C4-alkyι)carbonyl, (Q-Q-Halogen- cycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, CONR5R6 oder -CH2NR7R8 steht, und R3 B für Halogen, Q-C3-Alkyl, CrC8-Halogenalkyl steht, und R2, R4, R5, R6, R7 und R8 jeweils die oben angegebenen Bedeutungen haben, sind neu und ebenfalls Gegenstand dieser Anmeldung. in which a) R 1_B for QQ-alkyl, QQ-alkylsulfinyl, QC 6 -alkylsulfonyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; CC 6 -haloalkyl, CC 4 -haloalkylthio, QQ-haloalkylsulfinyl, QQ-haloalkylsulfonyl, halo -CC 4 -alkoxy-C r C -alkyl, C 3 -C 8 -halo-cycloalkyl, each with 1 to 9 fluoro-, Chlorine and / or bromine atoms; Formyl, formyl-QQ-alkyl, (QC 3 -alkyl) carbonyl-QQ-alkyl, (QQ-alkoxy) carbonyl-QC 3 -alkyl; Halogen (QQ-alkyl) carbonyl-QQ-alkyl, halogen (QQ-alk-oxy) carbonyl-QQ-alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (QQ-alkyl) carbonyl, (QQ-alkoxy) carbonyl, (QQ-alkoxy-QQ-alkyl) - carbonyl, (QQ-cycloalkyOcarbonyl; (QQ-haloalkyl) carbonyl, (QQ- haloalkoxy) carbonyl, (halogen-QQ- alkoxy-QQ-alkyl) carbonyl, (QQ-halocycloalkyl) carbonyl each with 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= 0) C (= O) R 4 , CONR 5 R δ or - CH 2 NR 7 R 8 is and R 3 "B is hydrogen, halogen, QQ-alkyl, QQ-haloalkyl, or b) R 1_B is hydrogen, QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy -QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfinyl, QQ-haloalkylsulfonyl, halo-QQ-alkoxy-Q- C 4 -alkyl, C 3 -C 8 -halogenocycloalkyl, each with 1 to 9 Fluorine, chlorine and / or bromine atoms; formyl, formyl-QQ-alkyl, (QC 3 -alkyl) carbonyl-QQ-alkyl, (QQ- alkoxy) carbonyl-QQ-alkyl; halogen (QQ-alkyι) carbonyl- QQ-alkyl, halogen (-C-C 3 -alkoxy) carbonyl-Cι-C 3 -alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (CC 8 -alkyl) carbonyl, (QQ-alkoxy) carb onyl, (QQ-alkoxy-QQ-alkyl) carbonyl, (C 3 -C 8 cycloalkyl) carbonyl; (Cι-Q-haloalkyl) carbonyl, (QQ-haloalkoxy) carbonyl, (halogen-QQ-alkoxy-QC 4 -alkyl) carbonyl, (QQ-halo-cycloalkyl) carbonyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; or -C (= O) C (= O) R 4 , CONR 5 R 6 or -CH 2 NR 7 R 8 , and R 3 B represents halogen, QC 3 alkyl, C r C 8 haloalkyl, and R 2 , R 4 , R 5 , R 6 , R 7 and R 8 each have the meanings given above, are new and also the subject of this application.
Die bevorzugten, besonders bevorzugten bzw. ganz besonders bevorzugten Bedeutungen von R1 undThe preferred, particularly preferred or very particularly preferred meanings of R 1 and
R3 finden auf R1_B und R3"B entsprechend Anwendung, wobei im Fall a) R1_B jeweils nicht für Wasser- stoff steht und im Fall b) R3"B nicht für Wasserstoff steht. Die bevorzugten, besonders bevorzugten bzw. ganz besonders bevorzugten Bedeutungen von R2, R4, R5, R6, R und R gelten ebenfalls für die neuen Verbindungen der Formel (Dl-b).R 3 are applied to R 1_B and R 3 "B accordingly, whereby in case a) R 1_B does not stand for hydrogen and in case b) R 3" B does not stand for hydrogen. The preferred, particularly preferred or very particularly preferred meanings of R 2 , R 4 , R 5 , R 6 , R and R also apply to the new compounds of the formula (Dl-b).
Hervorgehoben sind Verbindungen der Formel (ITI-b), in welcher R und R jeweils für Wasserstoff und R3 für Fluor, Chlor, Methyl, Ethyl, Trifluormethyl oder Pentafluorethyl steht.Compounds of the formula (ITI-b) are emphasized, in which R and R each represent hydrogen and R 3 represents fluorine, chlorine, methyl, ethyl, trifluoromethyl or pentafluoroethyl.
Anilin-Derivate der Formel (HI), in denen L für L-l steht, werden außerdem erhalten, indem man g) Anilinhalogenide der Formel (XI)Aniline derivatives of the formula (HI) in which L represents L-1 are also obtained by g) aniline halides of the formula (XI)
in welcher R1_A und R2 die oben angegebenen Bedeutungen haben und X4 für Halogen steht, in einem ersten Schritt mit Alkinen der Formel (XU) R\ CH, (XU) CH, in welcher R3 die oben angegebenen Bedeutungen hat, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt und in einem zweiten Schritt die so erhaltenen Alkinaniline der Formel (XDI) in which R 1_A and R 2 have the meanings given above and X 4 represents halogen, in a first step with alkynes of the formula (XU) R \ CH, (XU) CH, in which R 3 has the meanings given above, in In the presence of a catalyst, if appropriate in the presence of a base and if appropriate in the presence of a diluent, and in a second step the alkynanilines of the formula (XDI) thus obtained
Bedeutungen haben gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators hydriert. Meanings have optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst.
Die zur Durchführung des erfindungsgemäßen Verfahrens (g) als Ausgangsstoffe benötigten Anilinhalogenide sind durch die Formel (XI) allgemein definiert. In dieser Formel (XI) hat R2 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden. R1_A hat bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die im Zu- sammehhang mit der Beschreibung der Verbindungen der Formel (TV) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben sind.Formula (XI) provides a general definition of the aniline halides required as starting materials for carrying out process (g) according to the invention. In this formula (XI), R 2 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were. R 1_A preferably, particularly preferably or very particularly preferably has those meanings which together with the description of the compounds of the formula (TV) as preferred, particularly preferred or very particularly preferred for this radical.
Die Anilinhalogenide der Formel (XI) sind bekannt und/oder können nach bekannten Verfahren, z.B. aus den entsprechenden am Stickstoff unsubstituierten Derivaten durch Umsetzung mit den Halogeniden der Formel (IV), erhalten werden.The aniline halides of formula (XI) are known and / or can be prepared by known methods, e.g. can be obtained from the corresponding derivatives unsubstituted on nitrogen by reaction with the halides of the formula (IV).
Die zur Durchführung des erfindungsgemäßen Verfahrens (g) als Ausgangsstoffe weiterhin benötigten Alkine sind durch die Formel (XU) allgemein definiert. In dieser Formel (XU) hat R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden.Formula (XU) provides a general definition of the alkynes still required as starting materials for carrying out process (g) according to the invention. In this formula (XU), R 3 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were.
Die Alkine der Formel (XU) sind bekannt.The alkynes of the formula (XU) are known.
Die bei der Durchführung des erfindungsgemäßen Verfahrens (g) als Zwischenprodukte durchlaufenen Alkinaniline sind durch die Formel (XTfl) allgemein definiert. In dieser Formel (XIO) haben R2 und R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden. R1_A hat bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die im Zusammenhang mit der Beschreibung der Verbindungen der Formel (IV) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben sind.The formula (XTfl) provides a general definition of the alkynanilines passed through as intermediates when carrying out process (g) according to the invention. In this formula (XIO), R 2 and R 3 have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or very particularly preferred for these residues were specified. R 1_A preferably, particularly preferably or very particularly preferably has those meanings which are given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (IV).
Die Alkinaniline der Formel (XIO) sind teilweise bekannt. Sie werden nach dem erfindungsgemäßen Verfahren (g) erhalten.Some of the alkynanilines of the formula (XIO) are known. They are obtained by process (g) according to the invention.
Sollen Anilin-Derivate der Formel (JE), in welcher R1 für Wasserstoff steht, erhalten werden, so wird R1_A entsprechend ausgewählt, um die Funktion einer Schutzgruppe zu erfüllen, welche im Anschluss an das erfindungsgemäße Verfahren (g) nach üblichen Methoden wieder entfernt werden kann.If aniline derivatives of the formula (JE) in which R 1 stands for hydrogen are to be obtained, R 1_A is selected accordingly in order to fulfill the function of a protective group which, after the process (g) according to the invention, is used again by customary methods can be removed.
Die Anilin-Derivate der Formel (JE), in denen L für L-2, L-3 oder L-4 steht, sind bekannt und/oder können nach bekannten Verfahren erhalten werden (vgl. z.B. EP-A 1 036 793 und EP-A 0 737 682).The aniline derivatives of the formula (JE) in which L represents L-2, L-3 or L-4 are known and / or can be obtained by known processes (cf. for example EP-A 1 036 793 and EP -A 0 737 682).
Anilin-Derivate der Formel (JE), in denen L für L-2, L-3 oder L-4 steht und R1 nicht für Wasserstoff steht, können erhalten werden, indem man Aniline der Formel (πi-c) in welcherAniline derivatives of the formula (JE) in which L is L-2, L-3 or L-4 and R 1 is not hydrogen can be obtained by using anilines of the formula (πi-c) in which
L1 für L-2, L-3 oder L-4 steht undL 1 stands for L-2, L-3 or L-4 and
L-2, L-3, L-4 und R3 die oben angegebenen Bedeutungen haben, mit Halogeniden der Formel (IV) p1-A γ2 R X (rv) in welcher RμA und X2 die oben angegebenen Bedeutungen hat, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt. [Die Reaktionsbedingungen des Verfahrens (b) gelten entsprechend.]L-2, L-3, L-4 and R 3 have the meanings given above, with halides of the formula (IV) p1-A γ 2 RX (rv) in which R μA and X 2 has the meanings indicated above, in In the presence of a base and in the presence of a diluent. [The reaction conditions of process (b) apply accordingly.]
Verfahren (b)Method (b)
Verwendet man 5-Fluor-l,3-dimethyl-N-[2-(3-methylbutyl)phenyl]-lH-pyrazol-4-carboxamid und Ethyl-chlor(oxo)acetat als Ausgangsstoffe, so kann der Verlauf des erfϊndungsgemäßen Verfahrens (b) durch das folgende Formelschema veranschaulicht werden:If 5-fluoro-1,3-dimethyl-N- [2- (3-methylbutyl) phenyl] -1H-pyrazole-4-carboxamide and ethyl chloro (oxo) acetate are used as starting materials, the course of the process according to the invention can (b) are illustrated by the following formula scheme:
Die zur Durchführung des erfϊndungsgemäßen Verfahrens (b) als Ausgangsstoffe benötigten Isopentylcarboxanilide sind durch die Formel (I-a) allgemein definiert. In dieser Formel (I-a) haben R2, R3 und A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindun- gen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden.Formula (Ia) provides a general definition of the isopentylcarboxanilides required as starting materials for carrying out process (b) according to the invention. In this formula (Ia), R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred, particularly preferred or were very particularly preferably specified for these radicals.
Die Isopentylcarboxanilide der Formel (I-a) sind ebenfalls erfindungsgemäße Verbindungen und ebenfalls Gegenstand dieser Anmeldung. Sie können nach einem der erfindungsgemäßen Verfahren (a), (c), (d) oder (e) erhalten werden (mit R1 = Wasserstoff).The isopentylcarboxanilides of the formula (Ia) are likewise compounds according to the invention and are also the subject of this application. They can be obtained by one of the processes (a), (c), (d) or (e) (with R 1 = hydrogen).
Die zur Durchführung des erfindungsgemäßen Verfahrens (b) als Ausgangsstoffe weiterhin benötigten Halogenide sind durch die Formel (IV) allgemein definiert.Formula (IV) provides a general definition of the halides which are further required as starting materials for carrying out process (b) according to the invention.
R1_A steht bevorzugt für Q-Q-Alkyl, Q-Q-Alkylsulfinyl, Q-Q-Alkylsulfonyl, Q-Q-Alkoxy-Q- Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halogenal- kylsulfinyl, Q-Q-Halogenalkylsulfonyl, Halogen-Cι-C3-alkoxy-C C3-alkyl, Q-Q-Halo- gencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q- Q-alkyl, (Q-Q-Alkyl)carbonyl-Q-Q-alkyl, (Q-C3-Alkoxy)carbonyl-Q-Q-alkyl; Halogen- (CrC3-alkyl)carbonyl-Cι-C3-alkyl, Halogen-(Q-Q-alkoxy)carbonyl-Q-Q-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Cι-C3-Alkoxy-CrC3-alkyl)carbonyl, (Q- C6-Cycloalkyl)carbonyl; (Cι-C -Halogenalkyl)carbonyl, (Q-Q-Halogenalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyl)carbonyl, (C3-C6-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen; oder -C(=O)C(=O)R4, -CONR5R6 oder -CH2NR7R8.R 1_A preferably represents QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloal- kylsulfinyl, QQ-haloalkylsulfonyl, halo -CC 3 -alkoxy-C 3 -alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; Formyl, formyl-Q-Q-alkyl, (QQ-alkyl) carbonyl-QQ-alkyl, (QC 3 -alkoxy) carbonyl-QQ-alkyl; Halogen (CrC 3 -alkyl) carbonyl -CC 3 -alkyl, halogen- (QQ-alkoxy) carbonyl-QQ-alkyl, each with 1 to 13 fluorine, chlorine and / or bromine atoms; (QQ-alkyl) carbonyl, (QQ-alkoxy) carbonyl, (-C-C3-alkoxy-C r C 3 alkyl) carbonyl, (Q- C 6 cycloalkyl) carbonyl; (-C-C-haloalkyl) carbonyl, (QQ-haloalkoxy) carbonyl, (halo-QQ-alkoxy-QQ-alkyl) carbonyl, (C 3 -C 6 halocycloalkyl) carbonyl, each with 1 to 9 fluorine, chlorine and or bromine atoms; or -C (= O) C (= O) R 4 , -CONR 5 R 6 or -CH 2 NR 7 R 8 .
R1_A steht besonders bevorzugt für Methyl, Ethyl, n- oder iso-Propyl, n-, iso-, sec- oder tert-Butyl, Pentyl oder Hexyl, Methylsulfinyl, Ethylsulfinyl, n- oder iso-Propylsulfinyl, n-, iso-, sec- oder tert-Butylsulfinyl, Methylsulfonyl, Ethylsulfonyl, n- oder iso-Propylsulfonyl, n-, iso-, sec- oder tert-Butylsulfonyl, Methoxymethyl, Methoxyethyl, Ethoxymethyl, Ethoxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Trichlormethyl, Trifluorethyl, Difluormethylthio, Difluorchlormethylthio, Trifluormethylthio, Trifluormethylsulfinyl, Tri- fluormethylsulfonyl, Trifluormethoxymethyl; Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -(CH2)2-CO-CH3, -(CH2)2-CO-CH2CH3, -(CH2)2-CO-CH(CH3)2, -CH2-CO2CH3, -CH2-CO2CH2CH3, -CH2-CO2CH(CH3)2, -(CH2)2-CO2CH3, -(CH2)2-CO2CH2CH3, -(CH2)2-CO2CH(CH3)2, -CH2-CO-CF3, -CH2-CO-CCl3, -CH2-CO-CH2CF3, -CH2-CO-CH2CCl3, -(CH2)2-CO-CH2CF3, -(CH2)2-C0-CH2CC13, -CH2-CO2CH2CF3, -CH2-CO2CF2CF3, -CH2-CO2CH2CCl3, -CH2-CO2CCl2CCl3, -(CH2)2-CO2CH2CF3, -(CH2)2-CO2CF2CF3, -(CH2)2-CO2CH2CCl3, -(CH2)2-C02CC12CC13; Methylcarbonyl, Ethylcarbonyl, n-Propylcarbonyl, iso-Propylcarbonyl, tert-Butylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Butoxycarbonyl, Cyclopropylcarbonyl; Trifluorme- thylcarbonyl, Trifluormethoxycarbonyl, oder -C(=O)C(=O)R5, -CONR^7 oder -CH2NR8R9.R 1_A particularly preferably represents methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfinyl, ethylsulfinyl, n- or iso-propylsulfinyl, n-, iso- , sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichl Trifluoroethyl, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl; Formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 , - (CH 2 ) 2 -CO-CH 3 , - (CH 2 ) 2 -CO-CH 2 CH 3 , - (CH 2 ) 2 -CO-CH (CH 3 ) 2 , -CH 2 -CO 2 CH 3 , -CH 2 -CO 2 CH 2 CH 3 , -CH 2 -CO 2 CH (CH 3 ) 2 , - (CH 2 ) 2 -CO 2 CH 3 , - (CH 2 ) 2 -CO 2 CH 2 CH 3 , - (CH 2 ) 2 -CO 2 CH (CH 3 ) 2 , -CH 2 -CO-CF 3 , -CH 2 -CO-CCl 3 , -CH 2 -CO-CH 2 CF 3 , -CH 2 - CO-CH 2 CCl 3 , - (CH 2 ) 2 -CO-CH 2 CF 3 , - (CH 2 ) 2 -C0-CH 2 CC1 3 , -CH 2 -CO 2 CH 2 CF 3 , -CH 2 - CO 2 CF 2 CF 3 , -CH 2 -CO 2 CH 2 CCl 3 , -CH 2 -CO 2 CCl 2 CCl 3 , - (CH 2 ) 2 -CO 2 CH 2 CF 3 , - (CH 2 ) 2 - CO 2 CF 2 CF 3 , - (CH 2 ) 2 -CO 2 CH 2 CCl 3 , - (CH 2 ) 2 -C0 2 CC1 2 CC1 3 ; Methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, cyclopropylcarbonyl; Trifluoromethyl carbonyl, trifluoromethoxycarbonyl, or -C (= O) C (= O) R 5 , -CONR ^ 7 or -CH 2 NR 8 R 9 .
R1 A steht ganz besonders bevorzugt für Methyl, Methoxymethyl, Formyl, -CH2-CHO, -(CH2)2-CHO, -CH2-CO-CH3, -CH2-CO-CH2CH3, -CH2-CO-CH(CH3)2, -C(=O)CHO, -C(=O)C(=0)CH3, -C(=O)C(=O)CH2OCH3, -C(=O)CO2CH3, -C(=0)CO2CH2CH3.R 1 A very particularly preferably represents methyl, methoxymethyl, formyl, -CH 2 -CHO, - (CH 2 ) 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , - CH 2 -CO-CH (CH 3 ) 2 , -C (= O) CHO, -C (= O) C (= 0) CH 3 , -C (= O) C (= O) CH 2 OCH 3 , -C (= O) CO 2 CH 3 , -C (= 0) CO 2 CH 2 CH 3 .
X2 steht bevorzugt für Chlor oder Brom.X 2 preferably represents chlorine or bromine.
Halogenide der Formel (IV) sind bekannt. Verfahren (c)Halides of the formula (IV) are known. Procedure (c)
Verwendet man 2-Iod-N-[2-(3-methylbutanoyl)phenyl]benzamid als Ausgangsstoff, sowie Hydrazin und eine Base so kann der Verlauf des erfindungsgemäßen Verfahrens (c) durch das folgende Formelschema veranschaulicht werden:If 2-iodo-N- [2- (3-methylbutanoyl) phenyl] benzamide is used as the starting material, and hydrazine and a base, the course of process (c) according to the invention can be illustrated by the following formula:
Die zur Durchführung des erfϊndungsgemäßen Verfahrens (c) als Ausgangsstoffe benötigten Isopenton- Derivate sind durch die Formel (V) allgemein definiert. In dieser Formel (V) haben R1, R2, R3 und A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevor- zugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden.Formula (V) provides a general definition of the isopentone derivatives required as starting materials for carrying out process (c) according to the invention. In this formula (V), R 1 , R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which have already been given preference in connection with the description of the compounds of the formula (I) according to the invention were preferred or very particularly preferred for these radicals.
Die Isopenton-Derivate der Formel (V) sind neu. Sie werden erhalten, indem man h) Carbonsäure-Derivate der Formel (H) O ), A Λ. (H in welcher A die oben angegebenen Bedeutungen hat und X1 für Halogen oder Hydroxy steht, mit Alkanonanilinen der Formel (X)The isopentone derivatives of the formula (V) are new. They are obtained by h) carboxylic acid derivatives of the formula (H) O), A Λ. (H in which A has the meanings given above and X 1 represents halogen or hydroxy, with alkanonanilines of the formula (X)
in welcher R1, R2 und R3 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. in which R 1 , R 2 and R 3 have the meanings given above, if appropriate in the presence of a catalyst, if appropriate in the presence of a condensing agent, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Die zur Durchführung des erfindungsgemäßen Verfahrens (h) als Ausgangsstoffe benötigten Carbonsäure-Derivate der Formel (H) wurden bereits im Zusammenhang mit dem erfϊndungsgemäßen Verfahren (a) beschrieben. Die zur Durchführung des erfindungsgemäßen Verfahrens (h) weiterhin als Ausgangsstoffe benötigten Alkanonaniline der Formel (X) wurden bereits im Zusammenhang mit dem erfϊndungsgemäßen Verfahren (f) beschrieben.The carboxylic acid derivatives of the formula (H) required as starting materials for carrying out process (h) according to the invention have already been described in connection with process (a) according to the invention. The alkanonanilines of the formula (X) which are furthermore required as starting materials for carrying out process (h) according to the invention have already been described in connection with process (f) according to the invention.
Verfahren (d)Method (d)
Verwendet man N-{2-[3,3-Dimethylbut-l-en-l-yl]phenyl}-5-fluor-l,3-dimethyl-lH-pyrazol-4-carb- oxamid als Ausgangsstoff, sowie Wasserstoff so kann der Verlauf des erfϊndungsgemäßen Verfahrens (d) durch das folgende Formelschema veranschaulicht werden:If N- {2- [3,3-dimethylbut-1-en-1-yl] phenyl} -5-fluoro-1, 3-dimethyl-1H-pyrazole-4-carboxamide is used as the starting material, and hydrogen is so the course of the process (d) according to the invention can be illustrated by the following formula:
Die zur Durchführung des erfindungsgemäßen Verfalirens (d) als Ausgangsstoffe benötigten Isopen- ten-Derivate sind durch die Formel (VT) allgemein definiert. In dieser Formel (VT) haben R1, R2, R3 und A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden. Formula (VT) provides a general definition of the isopentene derivatives required as starting materials for carrying out process (d) according to the invention. In this formula (VT), R 1 , R 2 , R 3 and A have preferred, particularly preferably or very particularly preferably those meanings which have been preferred, particularly preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were very particularly preferably indicated for these residues.
Die Isopenten-Derivate der Formel (VI) sind neu. Sie werden erhalten, indem man j) Carboxamide der Formel (XTV)The isopentene derivatives of the formula (VI) are new. They are obtained by j) carboxamides of the formula (XTV)
in welcher R1, R2 und A die oben angegebenen Bedeutungen haben und X5 für Chlor, Brom, lod oder -OSO2CF3 steht, mit Alkenen der Formel (XV) in welcher R3 die oben angegebenen Bedeutungen hat, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt. Die zur Durchführung des erfindungsgemäßen Verfahrens (j) a^s Ausgangsstoffe benötigten Carboxamide sind durch die Formel (XTV) allgemein definiert. In dieser Formel (XIV) haben R1, R2 und A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden. X5 steht bevorzugt für Brom oder -OSO2CF3. in which R 1 , R 2 and A have the meanings given above and X 5 represents chlorine, bromine, iodine or -OSO 2 CF 3 , with alkenes of the formula (XV) in which R 3 has the meanings given above, in the presence of a catalyst, if appropriate in the presence of a base and if appropriate in the presence of a diluent. The carboxamides required for carrying out the process (j) a ^ s starting materials according to the invention are generally defined by the formula (XIV). In this formula (XIV), R 1 , R 2 and A have preferred, particularly preferably or very particularly preferably those meanings which have been preferred, particularly preferred or very particularly in connection with the description of the compounds of the formula (I) according to the invention were preferably given for these residues. X 5 preferably represents bromine or -OSO 2 CF 3 .
Die Carboxamide der Formel (XIV) sind bekannt oder können nach bekannten Methoden erhalten werden (vgl. WO 02/08195 und WO 02/08197).The carboxamides of the formula (XIV) are known or can be obtained by known methods (cf. WO 02/08195 and WO 02/08197).
Die zur Durchführung des erfindungsgemäßen Verfahrens (j) als Ausgangsstoffe weiterhin benötigten Alkene sind durch die Formel (XV) allgemein definiert. In dieser Formel (XV) hat R3 bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diesen Rest angegeben wurden.Formula (XV) provides a general definition of the alkenes which are further required as starting materials for carrying out process (j) according to the invention. In this formula (XV), R 3 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for this radical in connection with the description of the compounds of the formula (I) according to the invention were.
Die Alkene der Formel (XV) sind bekannt.The alkenes of the formula (XV) are known.
Verfahren (e) Verwendet man N-[2-(3,3-Dimethylbut-l-in-l-yl)phenyl]-5-fluor-l,3-dimethyl-lH-pyrazol-4-carbox- amid als Ausgangsstoff, sowie Wasserstoff so kann der Verlauf des erfindungsgemäßen Verfahrens (e) durch das folgende Formelschema veranschaulicht werden:Process (e) If N- [2- (3,3-dimethylbut-1-in-1-yl) phenyl] -5-fluoro-1, 3-dimethyl-1H-pyrazole-4-carboxamide is used as starting material and hydrogen, the course of process (e) according to the invention can be illustrated by the following formula:
Die zur Durchführung des erfϊndungsgemäßen Verfahrens (e) als Ausgangsstoffe benötigten Isopen- tin-Derivate sind durch die Formel (VE) allgemein definiert. In dieser Formel (VE) haben R1, R2, R3 und A bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt diejenigen Bedeutungen, die bereits im Zusammenhang mit der Beschreibung der erfϊndungsgemäßen Verbindungen der Formel (I) als bevorzugt, besonders bevorzugt bzw. ganz besonders bevorzugt für diese Reste angegeben wurden.Formula (VE) provides a general definition of the isopentene derivatives required as starting materials for carrying out process (e) according to the invention. In this formula (VE), R 1 , R 2 , R 3 and A have preferred, particularly preferred or very particularly preferred those meanings which have been preferred, particularly preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention were very particularly preferably indicated for these residues.
Die Isopentin-Derivate der Formel (VE), in welcher A nicht für AI steht, sind neu. Die Isopentin- Derivate der Formel (VE) werden erhalten, indem man k) Carboxamide der Formel (XIV)The isopentin derivatives of the formula (VE), in which A is not AI, are new. The isopentine derivatives of the formula (VE) are obtained by k) carboxamides of the formula (XIV)
in welcher R1, R2 und A die oben angegebenen Bedeutungen haben und X5 für Chlor, Brom, lod oder -OSO2CF3 steht, mit Alkinen der Formel (KE) R\ CH, H ZZ ^ (xπ) CH3 in welcher R3 die oben angegebenen Bedeutungen hat, in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart einer Base und gegebenen- falls in Gegenwart eines Verdünnungsmittels umsetzt. in which R 1 , R 2 and A have the meanings given above and X 5 represents chlorine, bromine, iodine or -OSO 2 CF 3 , with alkynes of the formula (KE) R \ CH, H ZZ ^ (xπ) CH 3 in which R 3 has the meanings given above, in the presence of a catalyst, if appropriate in the presence of a base and if appropriate in the presence of a diluent.
Die zur Durchführung des erfindungsgemäßen Verfahrens (k) als Ausgangsstoffe benötigten Carboxamide der Formel (XIV) sind bereits im Zusammenhang mit dem erfindungsgemäßen Verfahren (j) beschrieben worden.The carboxamides of the formula (XIV) required as starting materials for carrying out process (k) according to the invention have already been described in connection with process (j) according to the invention.
Die zur Durchführung des erfindungsgemäßen Verfahrens (k) als Ausgangsstoffe weiterhin benötigten Alkine der Formel (XE) sind bereits im Zusammenhang mit dem erfindungsgemäßen Verfahren (g) beschrieben worden.The alkynes of the formula (XE) which are further required as starting materials for carrying out process (k) according to the invention have already been described in connection with process (g) according to the invention.
Reaktionsbedingungenreaction conditions
Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (a) und (h) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische, alicyc- lische oder aromatische Kohlenwasserstoffe, wie beispielsweise Petrolether, Hexan, Heptan, Cyclo- hexan, Methylcyclohexan, Benzol, Toluol, Xylol oder Decalin; halogenierte Kohlenwasserstoffe, wie beispielsweise Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlor- ethan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t- amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan, 1,2-Diethoxyethan oder Anisol oder Ami- de, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid.Suitable diluents for carrying out processes (a) and (h) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as 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 or amide, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
Die erfindungsgemäßen Verfahren (a) und (h) werden 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 beispielsweise Natriumhydrid, Natrium- amid, Natrium-methylat, Natrium-ethylat, Kalium-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, Kaliumacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbonat, Natriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Triemylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl- benzylamin, Pyridin, N-Methylpiperidin, N-Methylmorpholin, N,N-Dimemylaminopyridin, Diazabicyc- looctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).Processes (a) and (h) according to the invention are optionally carried out in the presence of a suitable acid acceptor. All common inorganic or organic bases come as such question. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triemylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine N-methylpiperidine, N-methylmorpholine, N, N-dimemylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
Die erfϊndungsgemäßen Verfahren (a) und (h) werden gegebenenfalls in Gegenwart eines geeigneten Kondensationsmittels durchgeführt. Als solche kommen alle üblicherweise für derartige Amidie- rungsreaktionen verwendbaren Kondensationsmittel infrage. Beispielhaft genannt seien Säurehaloge- nidbildner wie Phosgen, Phosphortribromid, Phosphortrichlorid, Phosphorpentachlorid, Phosphor- oxychlorid oder Thionylchlorid; Anhydridbildner wie Chlorameisensäureethylester, Chlorameisen- säuremethylester, Chlorameisensäureisopropylester, Chlorameisensäureisobutylester oder Methan- sulfonylchlorid; Carbodiimide, wie N,N'-Dicyclohexylcarbodiimid (DCC) oder andere übliche Kondensationsmittel, wie Phosphorpentoxid, Polyphosphorsäure, N,N'-Carbonyldiimidazol, 2-Ethoxy-N- ethoxycarbonyl-l,2-dihydrochinolin (EEDQ), Triphenylphosphin/Tetrachlorkohlenstoff oder Brom- tripyrrolidinophosphonium-hexafluorophosphat.Processes (a) and (h) according to the invention are optionally carried out in the presence of a suitable condensing agent. All condensation agents that can normally be used for such amidation reactions are suitable as such. Acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride may be mentioned as examples; Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloride Bromo-tripyrrolidinophosphonium hexafluorophosphate.
Die erfϊndungsgemäßen Verfahren (a) und (h) werden gegebenenfalls in Gegenwart eines Katalysators durchgeführt. Beispielsweise genannt seien 4-Dimethylaminopyridin, 1-Hydroxy-ben- zotriazol oder Dimemylformamid.Processes (a) and (h) according to the invention are optionally carried out in the presence of a catalyst. Examples include 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimemylformamide.
Die Reaktionstemperaturen können bei der Durchführung der erfϊndungsgemäßen Verfahren (a) und (h) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0°C bis 150°C, vorzugsweise bei Temperaturen von 0°C bis 80°QThe reaction temperatures can be varied within a substantial range when carrying out processes (a) and (h) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
Zur Durchführung des erfϊndungsgemäßen Verfahrens (a) zur Herstellung der Verbindungen der Formel (I) setzt man pro mol des Carbonsäure-Derivates der Formel (E) im allgemeinen 0,2 bis 5 mol, vorzugsweise 0,5 bis 2 mol an Anilin-Derivat der Formel (JE) ein.To carry out process (a) according to the invention for the preparation of the compounds of the formula (I), 0.2 to 5 mol, preferably 0.5 to 2 mol, of aniline derivative are generally employed per mol of the carboxylic acid derivative of the formula (E) of the formula (JE).
Zur Durchführung des erfindungsgemäßen Verfahrens (h) zur Herstellung der Verbindungen der Formel (V) setzt man pro mol des Carbonsäure-Derivates der Formel (H) im allgemeinen 0,2 bis 5 mol, vorzugsweise 0,5 bis 2 mol an Alkanonanilin der Formel (X) ein. 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; halogenierte Kohlenwasserstoffe, wie beispielsweise Chlorbenzol, Dichlorbenzol, Dichlormethan, Chloroform, Tetrachlormethan, Dichlorethan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-tert-butylether, Methyl- tert-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan, 1,2-Diethoxyethan oder Anisol oder Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methyl- pyrrolidon oder Hexamethylphosphorsäuretriamid.To carry out process (h) according to the invention for the preparation of the compounds of the formula (V), 0.2 to 5 mol, preferably 0.5 to 2 mol, of alkanonaniline of the formula are generally employed per mol of the carboxylic acid derivative of the formula (H) (X) a. Suitable diluents for carrying out process (b) according to the invention are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole or amides, such as N, N-dimethylformamide, N, N- Dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.
Das erfindungsgemäße Verfahren (b) wird in Gegenwart einer Base 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 beispielsweise Natriumhydrid, Natriumamid, Natrium-methylat, Natrium- ethylat, Kaliurn-tert.-butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natrium- acetat, Kaliumacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kalium- hydrogencarbonat, Natriumhydrogencarbonat oder Caesiumcarbonat, sowie tertiäre Amine, wie Tri- methylamin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpiperidin, N-Methylmo holin, N,N-Dimemylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU).Process (b) according to the invention is carried out in the presence of a base. All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or cesium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine, pyridine, N-methylpiperidine, N-methylmo holin, N, N-dimemylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
Die Reaktionstemperaturen können bei der Durchführung des erfϊndungsgemäßen Verfahrens (b) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0°C bis 150°C, vorzugsweise bei Temperaturen von 20°C bis 110°C.The reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 110 ° C.
Zur Durchführung des erfindungsgemäßen Verfahrens (b) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Isopentylcarboxanilids der Formel (I-a) im allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 2 Mol an Halogenid der Formel (TV) ein.To carry out process (b) according to the invention for the preparation of the compounds of the formula (I), 0.2 to 5 mol, preferably 0.5 to 2 mol, of halide of the formula (TV) are generally employed per mole of the isopentylcarboxanilide of the formula (Ia) ) on.
Als Verdünnungsmittel zur Durchführung des erfϊndungsgemäßen Verfahrens (c) sowie des zweiten Schrittes von Verfahren (f) 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; halogenierte Kohlenwasserstoffe, wie beispielsweise Chlorbenzol, Dichlorbenzol, Dichlor- methan, Chloroform, Tetrachlormethan, Dichlorethan oder Trichlorethan; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-arnylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxy- ethan, 1,2-Diethoxyethan oder Anisol; Ketone, wie Aceton, Butanon, Methyl-isobutylketon oder Cyclohexanon; Nitrile, wie Acetonitril, Propionitril, n- oder i-Butyronitril oder Benzonitril; Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Methylpyrrolidon oder Hexamethylphosphorsäuretriamid; Sulfoxide, wie Dimethylsulfoxid; Sulfone, wie Sulfolan; Alkohole, wie Methanol, Ethanol, n- oder i-Propanol, n-, i-, sek- oder tert-Butanol, Ethandiol, Propan- 1,2-diol, Ethoxyethanol, Methoxyethanol, Diethylenglykolmonomethylether, Diethylenglykolmono- ethylether, Triethylenglykol, deren Gemische mit Wasser oder reines Wasser.All inert organic solvents are suitable as diluents for carrying out process (c) according to the invention and the second step of process (f). These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-arnyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxy ethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol, their Mix with water or pure water.
Das erfindungsgemäße Verfahren (c) sowie des zweiten Schrittes von Verfahren (f) wird in Gegen- wart einer Base durchgeführt. Als solche kommen vorzugsweise Erdalkalimetall- oder Alkalime- tallhydroxide, wie beispielsweise Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid infrage.Process (c) according to the invention and the second step of process (f) are carried out in the presence of a base. As such, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, are preferred.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens (c) sowie des zweiten Schrittes von Verfahren (f) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 100°C bis 300°C, vorzugsweise bei Temperaturen von 150°C bis 250°C.When carrying out process (c) according to the invention and the second step of process (f), the reaction temperatures can be varied within a substantial range. In general, temperatures from 100 ° C to 300 ° C, preferably at temperatures from 150 ° C to 250 ° C.
Zur Durchführung des erfϊndungsgemäßen Verfahrens (c) zur Herstellung der Verbindungen der Formel (I) setzt man pro Mol des Isopenton-Derivatives der Formel (V) im allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 3 Mol an Hydrazin (oder Hydrazin-hydrat) ein.In order to carry out process (c) according to the invention for the preparation of the compounds of the formula (I), 0.2 to 5 mol, preferably 0.5 to 3 mol, of hydrazine (or.) Are generally employed per mole of the isopentone derivative of the formula (V) Hydrazine hydrate).
Zur Durchführung des zweiten Schrittes von Verfahren (f) zur Herstellung der Verbindungen der Anilin-Derivate der Formel (JE) setzt man pro Mol des Alkanonanilines der Formel (X) im allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 3 Mol an Hydrazin (oder Hydrazin-hydrat) ein.To carry out the second step of process (f) for the preparation of the compounds of the aniline derivatives of the formula (JE), 0.2 to 5 mol, preferably 0.5 to 3 mol, are generally employed per mol of the alkanonaniline of the formula (X) of hydrazine (or hydrazine hydrate).
Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (d) und (e) sowie des zweiten Schrittes von Verfahren (g) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische oder alicyclische Kohlenwasserstoffe, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan oder Decalin; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimeth- oxyethan oder 1,2-Diethoxyethan; Alkohole, wie Methanol, Ethanol, n- oder iso-Propanol, n-, iso-, sec- oder tert-Butanol, Ethandiol, Propan-l,2-diol, Ethoxyethanol, Methoxyethanol, Diethylenglykolmonomethylether, Diethylenglykolmonoethylether, deren Gemische mit Wasser oder reines Wasser.Suitable diluents for carrying out processes (d) and (e) according to the invention and the second step of process (g) are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane; Alcohols, such as methanol, ethanol, n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.
Die erfindungsgemäßen Verfahren (d) und (e) sowie der zweite Schritt von Verfahren (g) werden in Gegenwart eines Katalysators durchgeführt. Als solche kommen alle Katalysatoren infrage, die für Hydrierungen üblicherweise verwendet werden. Beispielhaft seien genannt: Raney-Nickel, Palladium oder Platin, gegebenenfalls auf einem Trägermaterial, wie beispielsweise Aktivkohle.Processes (d) and (e) according to the invention and the second step of process (g) are carried out in the presence of a catalyst. As such, all catalysts that are suitable for Hydrogenations are commonly used. Examples include: Raney nickel, palladium or platinum, optionally on a carrier material, such as activated carbon.
Die Hydrierung in den erfindungsgemäßen Verfahren (d) und (e) sowie im zweiten Schritt von Ver- fahren (g) kann statt in Gegenwart von Wasserstoff in Kombination mit einem Katalysator auch in Anwesenheit von Triethylsilan durchgeführt werden.The hydrogenation in processes (d) and (e) according to the invention and in the second step of process (g) can also be carried out in the presence of triethylsilane instead of in the presence of hydrogen in combination with a catalyst.
Die Reaktionstemperaturen können bei der Durchführung der erfindungsgemäßen Verfahren (d) und (e) sowie des zweiten Schrittes von Verfahren (g) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0°C bis 150°C, vorzugsweise bei Temperaturen von 20°C bis lOO°C.When carrying out processes (d) and (e) according to the invention and the second step of process (g), the reaction temperatures can be varied within a substantial range. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C.
Die erfindungsgemäßen Verfahren (d) und (e) sowie der zweite Schritt von Verfahren (g) werden unter einem Wasserstoffdruck zwischen 0.5 and 200 bar, bevorzugt zwischen 2 und 50 bar, besonders bevorzugt zwischen 3 und 10 bar durchgeführt.The processes (d) and (e) according to the invention and the second step of process (g) are carried out under a hydrogen pressure between 0.5 and 200 bar, preferably between 2 and 50 bar, particularly preferably between 3 and 10 bar.
Als Verdünnungsmittel zur Durchführung des ersten Schrittes von Verfahren (f) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise aliphatische oder alicyclische Kohlenwasserstoffe, wie beispielsweise Petrolether, Hexan, Heptan, Cyclohexan, Methylcyclohexan oder Decalin; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan oder 1,2-Diethoxyethan.Suitable diluents for carrying out the first step of process (f) are all inert organic solvents. These preferably include aliphatic or alicyclic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane.
Die Reaktionstemperaturen können bei der Durchführung des ersten Schrittes von Verfahren (f) in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man bei Temperaturen von 0°C bis 200°C, vorzugsweise bei Temperaturen von 20°C bis 150°C.The reaction temperatures can be varied within a substantial range when carrying out the first step of process (f). In general, temperatures from 0 ° C to 200 ° C, preferably at temperatures from 20 ° C to 150 ° C.
Zur Durchführung des ersten Schrittes von Verfahren (f) zur Herstellung der Verbindungen der Alkanonaniline der Formel (X) setzt man pro Mol des Cyanoanilines der Formel (VJ ) im allgemeinen 0,2 bis 5 Mol, vorzugsweise 0,5 bis 3 Mol an Grignard-Reagenz der Formel (IX) ein.To carry out the first step of process (f) for the preparation of the compounds of the alkanonanilines of the formula (X), 0.2 to 5 moles, preferably 0.5 to 3 moles, of Grignard are generally employed per mole of the cyanoaniline of the formula (VJ) Reagent of the formula (IX).
Als Verdünnungsmittel zur Durchführung des ersten Schrittes von Verfahren (g) und der erfϊndungsgemäßen Verfahren (j) und (k) kommen alle inerten organischen Lösungsmittel in Betracht. Hierzu gehören vorzugsweise Nitrile, wie Acetonitril, Propionitril, n- oder i-Butyronitril oder Benzo- nitril oder Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid, N-Methylformanilid, N-Me- thylpyrrolidon oder Hexamethylphosphorsäuretriamid; Ether, wie Diethylether, Diisopropylether, Methyl-t-butylether, Methyl-t-amylether, Dioxan, Tetrahydrofuran, 1,2-Dimethoxyethan oder 1,2-All inert organic solvents are suitable as diluents for carrying out the first step of process (g) and processes (j) and (k) according to the invention. These preferably include nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Ethers, such as diethyl ether, diisopropyl ether, Methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-
Diethoxyethan.Diethoxyethane.
Der erste Schritt von Verfahren (g) und die erfindungsgemäßen Verfahren (j) und (k) werden 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 -hydrogen- carbonate, wie beispielsweise Natriumhydrid, Natriumamid, Natrium-methylat, Natrium-ethylat, Ka- lium-tert.-buτylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, Kalium- acetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbo- nat, Natriumhydrogencarbonat oder Ammoniumcarbonat, sowie tertiäre Amine, wie Trimethylamin, Triethylamin, Tributylamin, N,N-Dimethylanilin, N,N-Dimethyl-benzylamin, Pyridin, N-Methylpipe- ridin, N-Methylmoφholin, N,N-Dimethylaminopyridin, Diazabicyclooctan (DABCO), Diazabicyclo- nonen (DBN) oder Diazabicycloundecen (DBU).The first step of process (g) and processes (j) and (k) according to the invention are optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butylate , Sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methylmoφholin, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
Der erste Schritt von Verfahren (g) und die erfindungsgemäßen Verfahren (j) und (k) werden in Gegenwart eines oder mehrerer Katalysatoren durchgeführt.The first step of process (g) and processes (j) and (k) according to the invention are carried out in the presence of one or more catalysts.
Dazu eignen sich besonders Palladiumsalze oder -komplexe. Hierzu kommen vorzugsweise Palladiumchlorid, Palladiumacetat, Tetrakis-(triphenylphosphin)-Palladium oder Bis-(triphenylphos- phin)-Palladiumdichlorid infrage. Es kann auch ein Palladiumkomplex in der Reaktionsmischung erzeugt werden, wenn man ein Palladiumsalz und ein Komplexligand getrennt zur Reaktion zugibt.Palladium salts or complexes are particularly suitable for this. Palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium or bis (triphenylphosphine) palladium dichloride are preferably used for this purpose. A palladium complex can also be generated in the reaction mixture if a palladium salt and a complex ligand are added separately to the reaction.
Als Liganden kommen vorzugsweise Organophosphorverbindungen infrage. Beispielhaft seien ge- nannt: Triphenylphosphin, tri-o-Tolylphosphin, 2,2'-Bis(diphenylphosphino)-l,r-binaphthyl, Di- cyclohexylphosphinebiphenyl, 1 ,4-Bis(diphenylphosphino)butan, Bisdiphenylphosphinoferrocen, Di(tert.-butylphosphino)biphenyl, Di(cyclohexylphosphino)biphenyl, 2-Dicyclohexylphosphino-2'- N,N-dimethylaminobiphenyl, Tricyclohexylphosphin, Tri-tert.-butylphosphin. Es kann aber auch auf Liganden verzichtet werden.Organophosphorus compounds are preferred as ligands. Examples include: triphenylphosphine, tri-o-tolylphosphine, 2,2'-bis (diphenylphosphino) -l, r-binaphthyl, dicyclohexylphosphine biphenyl, 1,4-bis (diphenylphosphino) butane, bisdiphenylphosphinoferrocene, di (tert. -butylphosphino) biphenyl, di (cyclohexylphosphino) biphenyl, 2-dicyclohexylphosphino-2'-N, N-dimethylaminobiphenyl, tricyclohexylphosphine, tri-tert-butylphosphine. However, ligands can also be dispensed with.
Der erste Schritt von Verfahren (g) und die erfϊndungsgemäßen Verfahren (j) und (k) werden ferner gegebenenfalls in Gegenwart eines weiteren Metallsalzes, wie Kupfersalzen, beispielsweise Kupfer- (I)-iodid durchgeführt.The first step of process (g) and processes (j) and (k) according to the invention are also optionally carried out in the presence of a further metal salt, such as copper salts, for example copper (I) iodide.
Die Reaktionstemperaturen können bei der Durchführung des ersten Schrittes von Verfahren (g) und der erfindungsgemäßen Verfahren (j) und (k) in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen von 20°C bis 180°C, vorzugsweise bei Temperaturen von 50°C bis l50°C.When carrying out the first step of process (g) and processes (j) and (k) according to the invention, the reaction temperatures can be varied within a substantial range. in the Generally one works at temperatures from 20 ° C to 180 ° C, preferably at temperatures from 50 ° C to 150 ° C.
Zur Durchführung des ersten Schrittes von Verfahren (g) zur Herstellung der Anilin-Derivate der Formel (JE) setzt man pro Mol des Anilinhalogenides der Formel (XI) im allgemeinen 1 bis 5 mol, vorzugsweise 1 bis 3 mol an Alkin der Formel (XU) ein.To carry out the first step of process (g) for the preparation of the aniline derivatives of the formula (JE), 1 to 5 mol, preferably 1 to 3 mol, of alkyne of the formula (XU) are generally employed per mole of the aniline halide of the formula (XI) ) on.
Zur Durchführung des erfindungsgemäßen Verfahrens (j) zur Herstellung der Isopenten-Derivate der Formel (VT) setzt man pro Mol des Carboxamids der Formel (XIV) im allgemeinen 1 bis 5 mol, vor- zugsweise 1 bis 3 mol an Alken der Formel (XV) ein.To carry out process (j) according to the invention for the preparation of the isopentene derivatives of the formula (VT), 1 to 5 mol, preferably 1 to 3 mol, of alkene of the formula (XV.) Are generally employed per mole of the carboxamide of the formula (XIV) ) on.
Zur Durchführung des erfindungsgemäßen Verfahrens (k) zur Herstellung der Isopentin-Derivate der Formel (VE) setzt man pro Mol des Carboxamids der Formel (XIV) im allgemeinen 1 bis 5 mol, vorzugsweise 1 bis 3 mol an Alkin der Formel (XU) ein.To carry out process (k) according to the invention for the preparation of the isopentine derivatives of the formula (VE), 1 to 5 mol, preferably 1 to 3 mol, of alkyne of the formula (XU) are generally employed per mol of the carboxamide of the formula (XIV) ,
Wenn nicht anders angegeben, werden alle erfϊndungsgemäßen Verfahren 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.Unless otherwise stated, all of the processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
Die erfindungsgemäßen Stoffe weisen eine starke mikrobizide Wirkung auf und können zur Bekämpfung von unerwünschten Mikroorganismen, wie Fungi und Bakterien, im Pflanzenschutz und im Materialschutz eingesetzt werden.The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
Fungizide lassen sich Pflanzenschutz zur Bekämpfung von Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes und Deuteromycetes einsetzen.Fungicides can be used to protect plants against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
Bakterizide lassen sich im Pflanzenschutz zur Bekämpfung von Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae und Streptomycetaceae einsetzen.Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
Beispielhaft aber nicht begrenzend seien einige Erreger von pilzlichen und bakteriellen Erkrankungen, die unter die oben aufgezählten Oberbegriffe fallen, genannt: Xanthomonas-Arten, wie beispielsweise Xanthomonas campestris pv. oryzae; Pseudomonas-Arten, wie beispielsweise Pseudomonas syringae pv. lachrymans; Erwinia-Arten, wie beispielsweise Erwinia amylovora; Pythium-Arten, wie beispielsweise Pythium ultimum;Some pathogens of fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation: Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae; Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans; Erwinia species, such as, for example, Erwinia amylovora; Pythium species, such as, for example, Pythium ultimum;
Phytophthora-Arten, wie beispielsweise Phytophthora infestans; Pseudoperonospora-Arten, wie beispielsweise Pseudoperonospora humuli oderPhytophthora species, such as, for example, Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or
Pseudoperonospora cubensis;Pseudoperonospora cubensis;
Plasmopara-Arten, wie beispielsweise Plasmopara viticola;Plasmopara species, such as, for example, Plasmopara viticola;
Bremia-Arten, wie beispielsweise Bremia lactucae; Peronospora-Arten, wie beispielsweise Peronospora pisi oder P. brassicae;Bremia species, such as, for example, Bremia lactucae; Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe-Arten, wie beispielsweise Erysiphe graminis;Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca-Arten, wie beispielsweise Sphaerotheca fuliginea;Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera-Arten, wie beispielsweise Podosphaera leucotricha;Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia-Arten, wie beispielsweise Venturia inaequalis; Pyrenophora-Arten, wie beispielsweise Pyrenophora teres oder P. gramineaVenturia species, such as, for example, Venturia inaequalis; Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea
(Konidienform: Drechslera, Syn: Helminthosporium);(Conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus-Arten, wie beispielsweise Cochliobolus sativusCochliobolus species, such as, for example, Cochliobolus sativus
(Konidienform: Drechslera, Syn: Helminthosporium);(Conidial form: Drechslera, Syn: Helminthosporium);
Uromyces-Arten, wie beispielsweise Uromyces appendiculatus; Puccinia-Arten, wie beispielsweise Puccinia recondita;Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia-Arten, wie beispielsweise Sclerotinia sclerotiorum;Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia-Arten, wie beispielsweise Tilletia caries;Tilletia species, such as, for example, Tilletia caries;
Ustilago-Arten, wie beispielsweise Ustilago nuda oder Ustilago avenae;Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia-Arten, wie beispielsweise Pellicularia sasakii; Pyricularia-Arten, wie beispielsweise Pyricularia oryzae;Pellicularia species, such as, for example, Pellicularia sasakii; Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium-Arten, wie beispielsweise Fusarium culmorum;Fusarium species, such as, for example, Fusarium culmorum;
Botrytis-Arten, wie beispielsweise Botrytis cinerea;Botrytis species, such as, for example, Botrytis cinerea;
Septoria-Arten, wie beispielsweise Septoria nodorum;Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria-Arten, wie beispielsweise Leptosphaeria nodorum; Cercospora-Arten, wie beispielsweise Cercospora canescens;Leptosphaeria species, such as, for example, Leptosphaeria nodorum; Cercospora species, such as, for example, Cercospora canescens;
Alternaria-Arten, wie beispielsweise Altemaria brassicae;Alternaria species, such as, for example, Altemaria brassicae;
Pseudocercosporella-Arten, wie beispielsweise Pseudocercosporella heφotrichoides,Pseudocercosporella species, such as, for example, Pseudocercosporella heφotrichoides,
Rhizoctonia-Arten, wie beispielsweise Rhizoctonia solani.Rhizoctonia species, such as, for example, Rhizoctonia solani.
Die erfϊndungsgemäßen 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 substances according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind im vorliegenden Zusammenhang sol- ehe 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 substances which are able to stimulate the defense system of plants in such a way that the treated plants are subsequently inoculated with undesired microorganisms develop extensive resistance to these microorganisms.
Unter unerwünschten Mikroorganismen sind im vorliegenden Fall phytopathogene Pilze, Bakterien und Viren zu verstehen. Die erfϊndungsgemäßen Stoffe können also eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch die genannten Schaderreger zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im allgemeinen von 1 bis 10 Tage, vorzugsweise 1 bis 7 Tage nach der Behandlung der Pflanzen mit den Wirkstoffen.Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses. The substances according to the invention can thus be used to protect plants against the infestation by the named pathogens within a certain period of time after the treatment. The period within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active compounds.
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 fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
Dabei lassen sich die erfϊndungsgemäßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Getreidekrankheiten, wie beispielsweise gegen Puccinia-Arten und von Krankheiten im Wein-, Obst- und Gemüseanbau, wie beispielsweise gegen Botrytis-, Venturia- oder Altemaria-Arten, einsetzen.The active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Puccinia species, and for diseases in wine, fruit and vegetable cultivation, for example against Botrytis, Venturia or Altemaria 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 the crop yield. They are also less toxic and have good plant tolerance.
Die erfϊndungsgemäßen 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 Voφrodukte für die Synthese weiterer Wirkstoffe einsetzen.The active compounds according to the invention can, if appropriate in certain concentrations and application rates, also be used as herbicides, for influencing plant growth and for combating animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further 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). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtköφer, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Vermehrungsmaterial, bei- spielsweise Stecklinge, Knollen, Rhizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being 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, including for example cuttings, tubers, rhizomes, offshoots and seeds.
Die erfϊndungsgemäße 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 parts of plants with the active compounds takes place directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
Im Materialschutz lassen sich die erfϊndungsgemäßen Stoffe zum Schutz von technischen Materialien gegen Befall und Zerstörung durch unerwünschte Mikroorganismen einsetzen.In material protection, the substances according to the invention can be used to protect technical materials against attack 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 Vermehrung von Mikroorganismen beeinträchtigt werden können. Im Rahmen der vorliegenden Erfindung seien als technische Materialien vorzugsweise Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Anstrichmittel, Kühlschmiermittel und Wärmeübertragungsflüssigkeiten genannt, besonders bevorzugt Holz.In the present context, technical materials are understood to mean non-living materials that have been prepared for use in technology. For example, technical materials which are to be protected against microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which can be attacked or decomposed by microorganisms , In the context of the materials to be protected, parts of production systems, for example cooling water circuits, are also mentioned which can be impaired by the multiplication of microorganisms. In the context of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants 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 erfϊndungsgemäßen Wirkstoffe gegen Pilze, insbesondere Schimmelpilze, holzverfärbende und holzzerstörende Pilze (Basidiomyceten) sowie gegen Schleimorganismen und Algen.Bacteria, fungi, yeasts, algae and mucilaginous organisms may be mentioned as microorganisms which can cause degradation or a change in the technical materials. The active compounds according to the invention preferably act against fungi, in particular mold, wood-discoloring and wood-destroying fungi (Basidiomycetes) and against mucus organisms and algae.
Es seien beispielsweise Mikroorganismen der folgenden Gattungen genannt:Microorganisms of the following genera may be mentioned, for example:
Alternaria, wie Alternaria tenuis,Alternaria, such as Alternaria tenuis,
Aspergillus, wie Aspergillus niger,Aspergillus, such as Aspergillus niger,
Chaetomium, wie Chaetomium globosum,Chaetomium, like Chaetomium globosum,
Coniophora, wie Coniophora puetana, Lentinus, wie Lentinus tigrinus,Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,
Penicillium, wie Penicillium glaucum, Polyporus, wie Polyporus versicolor,Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporus versicolor,
Aureobasidium, wie Aureobasidium pullulans,Aureobasidium, such as Aureobasidium pullulans,
Sclerophoma, wie Sclerophoma pityophila,Sclerophoma, such as Sclerophoma pityophila,
Trichoderma, wie Trichoderma viride, Escherichia, wie Escherichia coli,Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli,
Pseudomonas, wie Pseudomonas aeruginosa,Pseudomonas, such as Pseudomonas aeruginosa,
Staphylococcus, wie Staphylococcus aureus.Staphylococcus, such as Staphylococcus aureus.
Die Wirkstoffe können in Abhängigkeit von ihren jeweiligen physikalischen und/ oder chemischen Eigenschaften in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-Kalt- und Warmnebel-Formulierungen.Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel 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, Keto- ne, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Di ethylsulfoxid, sowie Wasser. Mit verflüssigten gasförmigen Streck- mittein oder Trägerstoffen sind solche Flüssigkeiten gemeint, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe sowie Butan, Propan, Stickstoff und Kohlendioxid. Als feste Trägerstoffe kommen infrage: z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate. Als feste Trägerstoffe für Granulate kommen infrage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Bims, Marmor, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnussschalen, Maiskolben und Tabakstängel. Als Emulgier und/oder schaumerzeugende Mittel kommen infrage: z.B. nichtionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fett- alkoholether, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweiß- hydrolysate. Als Dispergiermittel kommen infrage: z.B. Lignin-Sulfϊtablaugen und Methylcellulose. Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförrnige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and the like Ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and diethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Solid carrier materials come into question: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, pumice, marble, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems. Suitable emulsifiers and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are: eg lignin sulfate and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other additives can 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 can be used.
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 percent by weight of active compound, preferably between 0.5 and 90%.
Die erfϊndungsgemäßen 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 Fällen 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 a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, 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:The following compounds can be considered as mixing partners: Fungicides:
2-Phenylphenol; 8-Hydroxychinolinsulfat; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampro- pylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Beno- danil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos; Binapacryl; Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole; Bupirimate; Buthiobate; Burylamin; Calciumpoly- sulfide; Capsimycin; Captafol; Captan; Carbendazim; Carboxin; Caφropamid; Carvone; Chinomethio- nat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate; Clozylacon; Cyazofa- mid; Cyflufenamid; Cymoxanil; Cyproconazole; Cyprodinil; Qyprofuram; Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet; Diclomezine; Dicloran; Diethofencarb; Difeno- conazole; Diflumetorim; DimetHrimol; Dimethomoφh; Dimoxystrobin; Diniconazole; Diniconazole- M; Dinocap; Diphenylamine; Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon; Edifenphos; Epoxiconazole; Ethaboxam; Elhirimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole; Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin; Fenpropi- moφh; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumoφh; Fluoromide; Fluoxa- strobin; Fluquinconazole; Fluφrimidol; Flusilazole; Flusulfamide; Flutolanil; Flutriafol; Folpet; Fosetyl- AI; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; hnazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris(albesil); Iodocarb; Ipconazole; Iprobenfos; Iprodione; Iprovalicarb; Irumamycin;2-phenylphenol; 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate; Burylamin; Calcium polysulfides; capsimycin; captafol; captan; carbendazim; carboxin; Caφropamid; carvones; Quinomethionate; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; Cyazofamid; cyflufenamid; cymoxanil; cyproconazole; cyprodinil; Qyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; diflumetorim; DimetHrimol; Dimethomoφh; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam; Elhirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; Fenpropi-moφh; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; Flumoφh; fluoromides; Fluoxastrobin; fluquinconazole; Fluφrimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-AI; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; hnazalil; Imibenconazole; Iminoctadine triacetate; Iminoctadine tris (albesil); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; Irumamycin;
Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb; Maneb; Meferimzone;isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone;
Mepanipyrim; Mepronil; Metalaxyl; Metalaxyl-M; Metconazole; Methasulfocarb; Methfuroxam;mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam;
Metiram; Metominostrobin; Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen; Nitrothal-isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysastrobin; Oxadixyl; Oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate; Penconazole; Pencycuron;metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron;
Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; Polyoxorim; Probenazole; Prochloraz; Pro- cymidone; Propamocarb; Propanosine-sodium; Propiconazole; Propineb; Proquinazid; Prothioconazole;phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; Procymidones; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole;
Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quincon- azole; Quinoxyfen; Quintozene; Simeconazole; Spiroxamine; Sulfur; Tebuconazole; Tecloftalam; Tec- nazene; Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl;pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl;
Thiram; Tioxymid; Tolclofos-methyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutil; Triazoxide;thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide;
Tricyclamide; Tricyclazole; Tridemoφh; Trifloxystrobin; Triflumizole; Triforine; Triticonazole; Uni- conazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-[2-[4-[[3-(4-Chlθφhenyl)-2- propmyl]oxy]-3-memoxyphenyl]emyl]-3-me yl-2-[(memylsulfonyl)ammo]-bu1anamid; 1-(1-Naphthale- nyl)-lH-pyrrol-2,5-dion; 2,3,5,6-Tetrachlor-4-(methylsulfonyl)-pyridin; 2-Amino-4-methyl-N-phenyl-5- thiazolcarboxamid; 2-CUor-N-(2,3-dmydro-l,l,3-trimemyl-lH-mden -yl)-3-pyridmcarboxarnide;Tricyclamide; Tricyclazole; Tridemoφh; trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-Chlθφhenyl) -2-propmyl] oxy] -3-memoxyphenyl] emyl] -3-me yl-2 - [(memylsulfonyl) ammo] - bu1anamid; 1- (1-naphthalenyl) -IH-pyrrole-2,5-dione; 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-phenyl-5-thiazole carboxamide; 2-CUor-N- (2,3-dmydro-l, l, 3-trimemyl-lH-mdenyl) -3-pyridmcarboxarnide;
3,4,5-Trichlor-2,6-pyridindicarbonitril; Actinovate; cis-l-(4-Chlθφhenyl)-2-(lH-l,2,4-triazol-l-yl)- cycloheptanol; Methyl l-(2,3-dihydro-2,2-dimethyl-lH-inden-l-yl)-lH-imidazol-5-carboxylat; Mono- kaliumcarbonat; N-(6-Methoxy-3-pyridinyl)-cyclopropancarboxamid; N-Butyl-8-(l,l-dimethylethyl)-l- oxaspiro[4.5]decan-3-amin; Natriumtetrathiocarbonat; sowie Kupfersalze und -Zubereitungen, wie3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-l- (4-Chlθφhenyl) -2- (lH-l, 2,4-triazol-l-yl) cycloheptanol; Methyl l- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -IH-imidazole-5-carboxylate; Mono potassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (l, l-dimethylethyl) -l-oxaspiro [4.5] decan-3-amine; sodium tetrathiocarbonate; as well as copper salts and preparations, such as
Bordeaux mixture; Kupferhydroxid; Kupfernaphthenat; Kupferoxychlorid; Kupfersulfat; Cufraneb;Bordeaux mixture; copper; copper naphthenate; copper oxychloride; Copper sulfate; Cufraneb;
Kupferoxid; Mancopper; Oxine-copper.copper; mancopper; Oxine-copper.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen.Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations.
Insektizide / Akarizide / Nematizide:Insecticides / acaricides / nematicides:
Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, AKD-1022, AKD-3059, AKD-3088, Alanycarb, Aldicarb, Aldoxycarb, Allethrin, Allethrin lR-isomers, Alpha- Cypermethrin (Alphamethrin), Amidoflumet, Aminocarb, Amitraz, Avermectin, AZ-60541, Azadi- rachtin, Azamethiphos, Azinphos-methyl, Azinphos-ethyl, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus thuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821, Baculoviren, Beauveria bassiana, Beauveria tenella, Benclothiaz, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Beta- Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin-S- cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Bistrifluron, BPMC, Brofen- prox, Bromophos-ethyl, Bromopropylate, Bromfenvinfos (-methyl), BTG-504, BTG-505, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butoxycarboxim, Butylpyridaben, Cadusafos, Camphechlor, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA-50439, Chinomethionat, Chlordane, Chlordimeform, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluaz- uron, Chlormephos, Chlorobenzilate, Chloropicrin, Chloφroxyfen, Chloφyrifos-methyl, Chloφyri- fos (-ethyl), Chlovaporthrin, Chromafenozide, Cis-Cypeimethrin, Cis-Resmethrin, Cis-Permethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidin, Clothiazoben, Codlemone, Coumaphos, Cyano- fenphos, Cyanophos, Cycloprene, Cycloprothrin, Cydia pomonella, Cyfluthrin, Cyhalothrin, Cyhexa- tin, Cypermethrin, Cyphenothrin (lR-trans-isomer), Cyromazine, DDT, Deltamethrin, Demeton-S- methyl, Demeton-S-methylsulphon, Diafenthiuron, Dialifos, Diazinon, Dichlofenthion, Dichlorvos, Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimefluthrin, Dimethoate, Dimethylvinphos, Dino- buton, Dinocap, Dinotefuran, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emamectin, Emamectin-benzoate, Empenthrin (lR-isomer), Endosulfan, Entomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Famphur, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobu- carb, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenvalerate, Fipronil, Flonicamid, Fluacrypyrim, Fluazuron, Flubenzimine, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenerim, Flufenoxuron, Flufen- prox, Flumethrin, Flupyrazofos, Flutenzin (Flufenzine), Fluvalinate, Fonofos, Formetanate, Formo- thion, Fosmethilan, Fosthiazate, Fubfenprox (Fluproxyfen), Furathiocarb, Gamma-Cyhalothrin, Gamma-HCH, Gossyplure, Grandlure, Granuloseviren, Halfenprox, Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Japonilure, Kadethrin, Kernpolyederviren, Kinoprene, Lambda-Cyhalothrin, Lindane, Lufenuron, Malathion, Mecarbam, Mesulfenfos, Metaldehyd, Metam-sodium, Methacrifos, Methami- dophos, Metharhizium anisopliae, Metharhizium flavoviride, Methidathion, Methiocarb, Methomyl, Methoprene, Methoxychlor, Methoxyfenozide, Metofluthrin, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, MKI-245, MON-45700, Monocrotophos, Moxidectin, MΗ-800, Naled, NC-104, NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI- 0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton-methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (eis-, trans-), Petroleum, PH-6045, Phenothrin (lR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phospho- carb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Resmethrin, RH- 5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetrachlorvinphos, Tetradifon, Tetramethrin, Tetramethrin (lR-isomer), Tetrasul, Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringiensin, Tolfenpyrad, Tralo- cythrin, Tralomethrin, Transfluthrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlopheni- dine, Trichlorfon, Trichoderma atroviride, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, WL-108477, WL-40027, YI-5201, YI-5301, YI-5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, die Verbindung 3-Methyl-phenyl- propylcarbamat (Tsumacide Z), die Verbindung 3-(5-Chlor-3-pyridinyl)-8-(2,2,2-trifluorethyl)-8-aza- bicyclo[3.2.1]octan-3-carbonitril (CAS-Reg.-Nr. 185982-80-3) und das entsprechende 3-endo-Iso- mere (CAS-Reg.-Nr. 185984-60-5) (vgl. WO 96/37494, WO 98/25923), sowie Präparate, welche insektizid wirksame Pflanzenextrakte, Nematoden, Pilze oder Viren enthalten.Abamectin, ABG-9008, Acephate, Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, AKD-1022, AKD-3059, AKD-3088, Alanycarb, Aldicarb, Aldoxycarb, Allethrin, Allethrin lR-isomers, Alpha-Cidermlhrhrine Aminocarb, Amitraz, Avermectin, AZ-60541, Azadirachtin, Azamethiphos, Azinphos-methyl, Azinphos-ethyl, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Bacillus thuringiensis strain EG-2348, strain EG-2348, 91, Bacillus thuringiensis strain NCTC-11821, Baculoviruses, Beauveria bassiana, Beauveria tenella, Benclothiaz, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Beta-Cyfluthrin, Beta-Cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Biorethomomethrin, Biorethomomethrin, Biorethanomethrin, Biorethanomethrin, Biorethanomethhrin - prox, bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb, buprofezin, butathiofos, butocarboxim, butoxycarboxim, butylpyridaben, cadusafos, camphechlor, carbaryl, carbofuran, carbophenothione, carbosl -50,439, quinomethionate, chlordane, chlordimeform, Chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, Chlorfluaz- uron, Chlormephos, Chlorobenzilate, chloropicrin, Chloφroxyfen, Chloφyrifos-methyl, Chloφyrifos (ethyl), Chlovaporthrin, chromafenozide, cis-Cypeimethrin, cis -Resmethrin, cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidin, clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyphenothrin (IR-trans-isomer), cyromazine, DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphone, diafenthiuron, dialifos, diazinon, dichlloron, dichl Dicofol, Dicrotophos, Dicyclanil, Diflubenzuron, Dimefluthrin, Dimethoate, Dimethylvinphos, Dino-buton, Dinocap, Dinotefuran, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn, DOWCO-439, Eflusilanate, Emectin-isamin-Eminectin-Emamin-tin-In , Endosulfan, Entomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos, Famphur, Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenfluthrin, Fenitrothion, Fenobarbhrox, Fenacrarbox, Fenacrarbox, Fenacrubarboxy, Fenacrubox, Carbacrine, Fenacrubate, Fenacrubate, Fenacrubate, Fenacrubate, Fenacrubate, Fenacrubate Carbine Fenpyrad, Fenpyrithrin, Fenpyroximate, Fensulfothion, Fenthion, Fentrifanil, Fenvalerate, Fipronil, Flonicamid, Fluacrypyrim, Fluazuron, Flubenzimine, Flubrocythrinate, Flucycloxuron, Flucythrinate, Flufenerim, Fluufenoxuron fen-prox, flumethrin, flupyrazofos, flutenzin (flufenzine), fluvalinate, fonofos, formetanate, formothion, fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb, gamma-cyhalothrin, gamma-HCH, grandfile, halofurulul, granulurululure, gossyplore, gossyplore Halofenozide, HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydramethylnone, Hydroprene, IKA-2002, Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobefos, Isazofos, Isofenphos, Isoprocarb, Isoxathionopyrinirinopin, Iphoninophenirone, Kinoxeninophenirone Lambda-Cyhalothrin, Lindane, Lufenuron, Malathion, Mecarbam, Mesulfenfos, Metaldehyde, Metam-sodium, Methacrifos, Methamidophos, Metharhician anisopliae, Metharhician flavoviride, Methidathione, Methiocarb, Methomyl, Methoprene, Metoxyhrin, Methoxhloro, Methoxy Chloride, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chlorine, Methoxy Chloride Mevinphos, Milbemectin, Milbemycin, MKI-245, MON-45700, Monocrotophos, Moxidectin, MΗ-800, Naled, NC-104, NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazine, NNI- 0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron, OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, Omethoate, Oxamyl, Oxydemeton-methyl, Paecilomyces fumosoroseus, Parathion-methyl, Parathion (-ethyl), Permethrin (eis, trans-), Petroleum, PH-6045, Phenothrin (IR-trans isomer), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, phospho- carb, Phoxim, Piperonyl butoxide, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Potassium oleate, Prallethrin, Profenofos, Profluthrin, Promecarb, Propaphos, Propargite, Propetamphos, Propoxur, Prothiofos, Prothoate, Protrifenofhrin, Pyrotrophin, Pyrethrin, Pyrothrin, Pyrothrin, Pyrothrin Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathione, Pyrimidifen, Pyriproxyfen, Quinalphos, Resmethrin, RH- 5849, Ribavirin, RU-12457, RU-15525, S-421, S-1833, Salithion, Sebufos, SI-0009, Silafluofen, Spinosad, Spirodiclofen, Spiromesifen, Sulfluramid, Sulfotep, Sulprofos, SZI-121, Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimfos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbam, Terbufos, Tetretramethrinethronethramethrinethramethronethramethramethrinethramethrinethramethronethramethrinethramethrinethramethrinethramethrinethramethronethramethramethrinethramethrametone, Tetramethrinethrametone, Tetramethrinethrametone, Tetramethronetone , Theta-Cypermethrin, Thiacloprid, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thiometon, Thiosultap-sodium, Thuringiensin, Tolfenpyrad, Tralocythrin, Tralomethrin, Transfluthrin n, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Trichoderma atroviride, Triflumuron, Trimethacarb, Vamidothion, Vaniliprole, Verbutin, Verticillium lecanii, WL-108477, WL-4001, YI-530301, YI-5201 5302, XMC, Xylylcarb, ZA-3274, Zeta-Cypermethrin, Zolaprofos, ZXI-8901, the compound 3-methyl-phenyl-propylcarbamate (Tsumacide Z), the compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS Reg. No. 185984-60-5) (cf. WO 96/37494, WO 98/25923), as well as preparations which have an insecticidal action Contain plant extracts, nematodes, fungi or viruses.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden oder mit Düngemitteln und Wachstumsregulatoren, Safener bzw. Semiochemicals ist möglich.A mixture with other known active compounds, such as herbicides or with fertilizers and growth regulators, safeners or semiochemicals, is also possible.
Darüber hinaus weisen die erfϊndungsgemäßen Verbindungen der Formel (I) auch sehr gute antimy- kotische Wirkungen auf. Sie besitzen ein sehr breites antimykotisches Wirkungsspektrum, ins- besondere gegen Dermatophyten und Sprosspilze, Schimmel und diphasische Pilze (z.B. gegen Can- dida-Spezies wie Candida albicans, Candida glabrata) sowie Epidermophyton floccosum, Asper- gillus-Spezies wie Aspergillus niger und Aspergillus fümigatus, 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 antimycotic effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus nig and Aspergillus , Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these fungi is in no way a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
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, Bestreichen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume-Verfahren aus- zubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. Es kann auch das Saatgut der Pflanzen behandelt werden.The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to remove the active ingredients using the ultra-low-volume process. bring or inject the drug preparation or the drug itself into the soil. The seeds of the plants can also be treated.
Beim Einsatz der erfindungsgemäßen Wirkstoffe als Fungizide können die Aufwandmengen je nach Applikationsart innerhalb eines größeren Bereiches variiert werden. Bei der Behandlung von Pflanzenteilen liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 10 und 1.000 g/ha. Bei der Saatgutbehandlung liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,001 und 50 g pro Kilogramm Saatgut, vorzugsweise zwischen 0,01 und 10 g pro Kilogramm Saatgut. Bei der Behandlung des Bodens liegen die Aufwandmengen an Wirkstoff im allgemeinen zwischen 0,1 und 10.000 g/ha, vorzugsweise zwischen 1 und 5.000 g/ha.When the active compounds according to the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates 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 plant species or plant species and their parts obtained by conventional biological breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The term “parts” or “parts of plants” or “parts of plants” was 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.Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive („synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfϊndungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen. Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen) Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften („Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kultuφflanzen, 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), CryUA, CryDIA, GyiπB2, Cry9c Cry2Ab, Cry3Bb und CryTF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im Folgenden „Bt Pflanzen"). Als Eigenschaften („Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften („Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirk- Stoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"- Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für , t Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (Z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen 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 Clearfϊeld® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf denDepending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention can also cause superadditive (“synergistic”) effects. For example, reduced application rates and / or widening of the activity spectrum and / or one Enhancing the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected. The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, Increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the Further and particularly highlighted 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 viruses as well as an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted. The traits are particularly emphasized as the plants' increased defense against insects, arachnids, nematodes and snails due to the toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (eg by the genes CryΙA (a) , CryIA (b), CryΙA (c), CryUA, CryDIA, GyiπB2, Cry9c Cry2Ab, Cry3Bb and CryTF as well as their combinations) are generated in the plants (hereinafter "Bt plants"). The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”). As properties (“traits”) ) the increased tolerance of the plants to certain herbicidal active substances, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT" gene) are also particularly emphasized. The genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants. Examples of “t plants” are corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (eg maize , Cotton, soy), KnockOut® (e.g. maize), StarLink® (e.g. maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties marketed under the name Clearfϊeld® (eg maize). Of course, these statements also apply to those developed in the future or to the future
Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen EigenschaftenComing plant varieties with these or future-developed genetic properties
(„Traits").( "Traits").
Die aufgeführten Pflanzen können besonders vorteilhaft erfindungsgemäß mit den Verbindungen der allgemeinen Formel (I) bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
Die Herstellung und die Verwendung der erfindungsgemäßen Wirkstoffe geht aus den folgenden Beispielen hervor. The preparation and use of the active compounds according to the invention can be seen from the following examples.
HerstellungsbeispielePreparation Examples
Beispiel 1example 1
Zu einer Lösung bestehend aus 388.5 mg (2.2 mmol) 5-Fluor-l,3-dimethyl-lH-pyrazol-4-carbonyl- chlorid und 0.45 ml (3.2 mmol) Triethylamin in 20 ml Tetrahydrofuran werden 326.5 mg (2.0 mmol) [2-(3-Methylbutyl)phenyl]amin (EOH) gegeben. Die Reaktionslösung wird 90 min. bei 60°C gerührt, über Kieselgel filtriert und aufkonzentriert. Säulenchromatographie (Gradient Cyclohexan/Essig- säureethylester) liefert 592 mg (98 % der Theorie) an 5-Fluor-l,3-dimethyl-N-[2-(3- methylbutyl)phenyl]-lH-pyrazol-4-carboxamid mit dem logP (pH 2.3) = 3.12.To a solution consisting of 388.5 mg (2.2 mmol) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride and 0.45 ml (3.2 mmol) of triethylamine in 20 ml of tetrahydrofuran are 326.5 mg (2.0 mmol) [ 2- (3-Methylbutyl) phenyl] amine (EOH) added. The reaction solution is 90 min. Stirred at 60 ° C, filtered through silica gel and concentrated. Column chromatography (gradient cyclohexane / ethyl acetate) provides 592 mg (98% of theory) of 5-fluoro-1,3-dimethyl-N- [2- (3-methylbutyl) phenyl] -1H-pyrazole-4-carboxamide the logP (pH 2.3) = 3.12.
Analog Beispiel 1 sowie entsprechend den Angaben in den allgemeinen Verfahrensbeschreibungen, werden die in der nachstehenden Tabelle 1 genannten Verbindungen der Formel (I) erhalten.Analogously to Example 1 and in accordance with the information in the general process descriptions, the compounds of the formula (I) mentioned in Table 1 below are obtained.
Tabelle 1Table 1
Herstellung von Ausgangsstoffen der Formel (HT)Production of starting materials of the formula (HT)
Beispiel (111-1)Example (111-1)
Eine Lösung bestehend aus 8.0 g (0.045 mol) l-(2-Amino-phenyl)-3-methyl-butan-l-on (X-l), 6.8 g (0.135 mol) Hydrazin-hydrat und 7.6 g (0.135 mol) Kaliumhydroxid in 90 ml Triethylenglycol wird für 6 h auf 210°C erhitzt. Zur Aufarbeitung wird bei Raumtemperatur Wasser und Essigsäureethylester zugegeben. Die organische Phase wird erneut mit Wasser gewaschen, über Magnesiumsulfat getrocknet und unter vermindertem Druck aufkonzentriert. Reinigung durch Säulenchromatographie (Cyclohexan/Essigsäureethylester 3:1) liefert 5.3 g (71.5 % der Theorie) an [2-(3-Methylbutyl)- phenyl]amin. A solution consisting of 8.0 g (0.045 mol) l- (2-aminophenyl) -3-methyl-butan-l-one (Xl), 6.8 g (0.135 mol) hydrazine hydrate and 7.6 g (0.135 mol) potassium hydroxide in 90 ml of triethylene glycol is heated to 210 ° C. for 6 h. For working up, water and ethyl acetate are added at room temperature. The organic phase is washed again with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification by column chromatography (cyclohexane / ethyl acetate 3: 1) yields 5.3 g (71.5% of theory) of [2- (3-methylbutyl) phenyl] amine.
Beispiel (JE-2)Example (JE-2)
3.23 g (15 mmol) N-[2-(3,3-Dimethyl-but-l-inyl)-phenyl]-acetamid (XIH-1) wurden in 40 ml Methanol vorgelegt. Man gab 0.5 g Palladium-Kohle (5 %) zu und hydriert anschließend im Autoklaven 20 h bei 4 bar Wasserstoffdruck. Nach Abtrennung des Katalysators und Entfernung des Lösungsmittels erhielt man 3.1 g (94 % der Theorie) an N-[2-(3,3-Dimethyl-butyl)-phenyl]-acetamid mit dem logP (pH 2.3) = 2.69.3.23 g (15 mmol) of N- [2- (3,3-dimethyl-but-1-ynyl) phenyl] acetamide (XIH-1) were placed in 40 ml of methanol. 0.5 g of palladium-carbon (5%) was added and the mixture was then hydrogenated in an autoclave at 4 bar hydrogen pressure for 20 h. After removal of the catalyst and removal of the solvent, 3.1 g (94% of theory) of N- [2- (3,3-dimethylbutyl) phenyl] acetamide with the logP (pH 2.3) = 2.69 were obtained.
Beispiel (Tfl-3)Example (Tfl-3)
0.5 g (2.3 mmol) N-[2-(3,3-Dimethyl-butyl)-phenyl]-acetamid (ffl-2) wurden in 20 ml 2N Salzsäure 5 h bei 100°C gerührt. Nach dem Abkühlen wurde 3 mal mit je 20 ml Essigsäureethylester extrahiert. Die organische Phase wurde abgetrennt, über Natriumsulfat getrocknet und eingeengt. Man erhielt 390 mg (79 % der Theorie) an 2-(3,3-Dimethyl-butyl)-phenylamin-Hydrochlorid mit dem logP (pH 2.3) = 2.20. Herstellung von Ausgangsstoffen der Formel (V)0.5 g (2.3 mmol) of N- [2- (3,3-dimethylbutyl) phenyl] acetamide (ffl-2) was stirred in 20 ml of 2N hydrochloric acid at 100 ° C. for 5 h. After cooling, the mixture was extracted 3 times with 20 ml of ethyl acetate each time. The organic phase was separated, dried over sodium sulfate and concentrated. 390 mg (79% of theory) of 2- (3,3-dimethylbutyl) phenylamine hydrochloride with the logP (pH 2.3) = 2.20 were obtained. Production of starting materials of the formula (V)
Beispiel (V-l)Example (V-l)
Bei Raumtemperatur werden 355.0 mg (2.0 mmol) l-(2-Amino-phenyl)-3-methyl-butan-l-on zu einer Lösung bestehend aus 388.5 mg (2.2 mmol) 5-Fluor-l,3-dimethyl-lH-pyrazol-4-carbonyl-chlorid und 0.45 ml (3.2 mmol) Triethylamin in 20 ml Tetrahydrofuran gegeben. Die Reaktionsmischung wird für 1.5 h bei 60°C gerührt, über Kieselgel filtriert und aufkonzentriert. Säulenchromatographie (Cyclohexan/Essigester : 3/1) liefert 577.7 mg (1.8 mmol, 88 % der Theorie) an 5-Fluor-l,3- dimethyl-lH-pyrazol-4-carbonsäure-[2-(3-methyl-butyryl)-phenyl]-amid mit dem logP (pH = 2.3) = 3.42.At room temperature, 355.0 mg (2.0 mmol) of l- (2-aminophenyl) -3-methyl-butan-l-one become a solution consisting of 388.5 mg (2.2 mmol) of 5-fluoro-1,3-dimethyl-1H -pyrazole-4-carbonyl chloride and 0.45 ml (3.2 mmol) of triethylamine in 20 ml of tetrahydrofuran. The reaction mixture is stirred at 60 ° C. for 1.5 h, filtered through silica gel and concentrated. Column chromatography (cyclohexane / ethyl acetate: 3/1) provides 577.7 mg (1.8 mmol, 88% of theory) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid- [2- (3-methyl-butyryl ) -phenyl] -amide with the logP (pH = 2.3) = 3.42.
Analog Beispiel (V-l) sowie entsprechend den Angaben in den allgemeinen Verfahrensbeschreibungen, werden die in der nachstehenden Tabelle 2 genannten Verbindungen der Formel (V) erhalten.Analogously to Example (V-1) and in accordance with the information in the general process descriptions, the compounds of the formula (V) mentioned in Table 2 below are obtained.
Tabelle 2Table 2
Herstellung von Ausgangsstoffen der Formel (VH)Production of starting materials of the formula (VH)
Beispiel (NTi-l)Example (NTi-l)
190 mg (1.0 mmol) 2-Trifluormethylbenzoesäure, 178 mg (0.83 mmol) 2-(3,3-Dimethyl-but-l-inyl)- phenylamin, 215 mg (1.67 mmol) Ν,Ν-Diisopropylethylamin und 583 mg (1.25 mmol) PyBrOP wurden in 8 ml Acetonitril 4 Tage bei Raumtemperatur gerührt. Das Gemisch wurde mit 10 ml Essig- säureethylester/Wasser 1:1 versetzt, die organische Phase abgetrennt und mit 10 ml gesättigter Ammon mchlorid-Lösung und anschließend mit 10 ml Wasser gewaschen. Abtrennen, Einengen und Trocknen der organischen Phase lieferte 950 mg Rohprodukt. Nach säulenchromatographischer Reinigung über Kieselgel 60 (Petrolether/Essigsäureethylester 10:1 -^ Essigsäureethylester) wurden 110 mg lN-[2-(3,3-Dimemyl-but-l-myl)-phenyl]-2-trifluoromethyl-benzamid erhalten [logP (pH 2.3) = 4.55]. 190 mg (1.0 mmol) 2-trifluoromethylbenzoic acid, 178 mg (0.83 mmol) 2- (3,3-dimethyl-but-l-ynyl) phenylamine, 215 mg (1.67 mmol) Ν, Ν-diisopropylethylamine and 583 mg (1.25 mmol) PyBrOP were stirred in 8 ml acetonitrile for 4 days at room temperature. The mixture was mixed with 10 ml of ethyl acetate / water 1: 1, the organic phase was separated off and washed with 10 ml of saturated ammonium chloride solution and then with 10 ml of water. Separation, concentration and drying of the organic phase gave 950 mg of crude product. After purification by column chromatography on silica gel 60 (petroleum ether / ethyl acetate 10: 1 → ethyl acetate), 110 mg of IN - [2- (3,3-dimethyl-but-l-methyl) -phenyl] -2-trifluoromethyl-benzamide were obtained [logP (pH 2.3) = 4.55].
Analog Beispiel (VTI-1) sowie entsprechend den Angaben in den allgemeinen Verfahrensbeschreibungen, werden die in der nachstehenden Tabelle 3 genannten Verbindungen der Formel (VE) erhalten. Tabelle 3Analogously to Example (VTI-1) and in accordance with the information in the general process descriptions, the compounds of the formula (VE) mentioned in Table 3 below are obtained. Table 3
Herstellung von Ausgangsstoffen der Formel (X)Production of starting materials of the formula (X)
Beispiel (X-nExample (X-n
Eine Lösung aus 29.5 g (0.25 mol) Antranilsäurenitril in 150 ml Tetrahydrofuran wird bei Rückfluss zu einer Suspension bestehend aus 18.2 g (0.75 mol) Magnesium, 375 ml einer 2 M Lösung von Isobutylmagnesiumbromid in Tetrahydrofuran und 15 ml Diethylether getropft. Nach 5 h Erhitzen unter Rückfluss wird die Reaktionsmischung bei 0°C mit 100 ml Wasser versetzt, und der pH-Wert mit Salzsäure auf 6 eingestellt. Die organische Phase wird mit Wasser gewaschen und über Magnesiumsulfat getrocknet. Aufkonzentration im Vakuum und Reinigung an Kieselgel (Eluent: Petrolether/Aceton 95:5) liefert 11.0 g (25 % der Theorie) an l-(2-Amino-phenyl)-3-methyl-butan-l- on mit dem logP (pH 2.3) = 2.89.A solution of 29.5 g (0.25 mol) of antraniliconitrile in 150 ml of tetrahydrofuran is added dropwise to a suspension consisting of 18.2 g (0.75 mol) of magnesium, 375 ml of a 2 M solution of isobutylmagnesium bromide in tetrahydrofuran and 15 ml of diethyl ether. After heating under reflux for 5 h, 100 ml of water are added to the reaction mixture at 0 ° C., and the pH is adjusted to 6 using hydrochloric acid. The organic phase is washed with water and dried over magnesium sulfate. Concentration in vacuo and cleaning on silica gel (eluent: Petroleum ether / acetone 95: 5) provides 11.0 g (25% of theory) of l- (2-aminophenyl) -3-methyl-butan-l-one with the logP (pH 2.3) = 2.89.
Herstellung von Ausgangsstoffen der Formel (Xlll)Production of starting materials of the formula (Xlll)
Beispiel (XD3-nExample (XD3-n
25.7 g (120 mmol) ortho-Bromacetanilid, 5.05 g (7.2 mmol) Bis(triphenylphosphin)palladi- um(π)chlorid und 1.37 g (7.2 mmol) Kupfer(I)iodid wurden in 450 ml Triethylamin unter Argon vorgelegt. Anschließend wurde bei Raumtemperatur innerhalb von 10 min. 17.8 g (180 mmol) 3,3- Dimethyl-1-butin zugetropft und 5 h bei 50°C gerührt. Die Reaktionsmischung wurde auf 2 1 Wasser gegossen, 3 mal mit je 250 ml Diethylether extrahiert, über Natriumsulfat getrocknet und eingeengt. Nach säulenchromatographischer Reinigung über Kieselgel 60 mit Methylenchlorid erhält man 25.9 g an N-[2-(3,3-Dimethyl-but-l-inyl)-phenyl]-acetamid mit dem logP (pH 2.3) = 3.03.25.7 g (120 mmol) ortho-bromoacetanilide, 5.05 g (7.2 mmol) bis (triphenylphosphine) palladium (π) chloride and 1.37 g (7.2 mmol) copper (I) iodide were placed in 450 ml triethylamine under argon. Then was at room temperature within 10 min. 17.8 g (180 mmol) of 3,3-dimethyl-1-butyne was added dropwise and the mixture was stirred at 50 ° C. for 5 h. The reaction mixture was poured onto 2 l of water, extracted 3 times with 250 ml of diethyl ether, dried over sodium sulfate and concentrated. After purification by column chromatography on silica gel 60 with methylene chloride, 25.9 g of N- [2- (3,3-dimethyl-but-1-ynyl) phenyl] acetamide with the logP (pH 2.3) = 3.03 are obtained.
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. 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. 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). Die lambda-max-Werte wurden an Hand der UV-Spektren von 200 nm bis 400 nm in den Maxima der chromatographischen Signale ermittelt. Anwendungsbeispiele:The logP values specified in the tables and manufacturing examples above are determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C. The determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; 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 on the basis of the retention times by linear interpolation between two successive alkanones). The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. Application examples:
Beispiel AExample A
Podosphaera-Test (Apfel) / protektivPodosphaera test (apple) / protective
Lösungsmittel: 24,5 Gewichtsteile Aceton 24,5 Gewichtsteile Dimethylacetamid Emulgator : 1 Gewichtsteil Alkyl-Aryl-PolyglykoletherSolvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated 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 Apfelmehltauerregers Podosphaera leucotricha inokuliert. Die Pflanzen werden dann im Gewächshaus bei ca. 23 °C und einer relativen Luftfeuchtigkeit von ca. 70 % 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 the pod mildew pathogen Podosphaera leucotricha. The plants are then placed in the greenhouse at about 23 ° C. and a relative humidity of about 70%.
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. Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Tabelle A Podosphaera-Test (Apfel) / protektiv Table A Podosphaera test (apple) / protective
Podosphaera-Test (Apfel) / protektiv Podosphaera test (apple) / protective
Beispiel BExample B
Venturia - Test (Apfel) / protektivVenturia test (apple) / protective
Lösungsmittel: 24,5 Gewichtsteile Aceton 24,5 Gewichtsteile Dimethylacetamid Emulgator : 1 Gewichtsteil Alkyl-Aryl-PolyglykoletherSolvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated 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 Konidiensuspension des Apfelschorferregers Venturia inaequalis inokuliert und verbleiben dann 1 Tag bei ca. 20°C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine.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 conidia suspension of the Venturia inaequalis apple scab pathogen and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric humidity for 1 day.
Die Pflanzen werden dann im Gewächshaus bei ca. 21°C und einer relativen Luftfeuchtigkeit von ca. 90 % aufgestellt. The plants are then placed in the greenhouse at approximately 21.degree. C. and a relative atmospheric humidity of approximately 90%.
Tabelle B Venturia - Test (Apfel) / protektiv Table B Venturia test (apple) / protective
Venturia - Test (Apfel) / protektiv Venturia test (apple) / protective
Beispiel CExample C
Botrytis - Test (Bohne) / protektivBotrytis test (bean) / protective
Lösungsmittel: 24,5 Gewichtsteile Aceton 24,5 Gewichtsteile Dimethylacetamid Emulgator : 1 Gewichtsteil Alkyl-Aryl-PolyglykoletherSolvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide emulsifier: 1 part by weight of alkyl aryl 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated 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 auf jedes Blatt 2 kleine mit Botrytis cinerea bewachsene Agarstückchen aufgelegt. Die inokulierten Pflanzen werden in einer abgedunkelten Kammer bei ca. 20°C und 100 % relativer Luftfeuchtigkeit 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, 2 small pieces of agar covered with botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at approx. 20 ° C and 100% relative humidity.
2 Tage nach der Inokulation wird die Größe der Befallsflecken auf den Blättern ausgewertet. Dabei bedeutet 0 % ein Wirkungsgrad, der demjenigen der Kontrolle entspricht, während ein Wirkungsgrad von 100 % bedeutet, dass kein Befall beobachtet wird. 2 days after the inoculation, the size of the infection spots on the leaves is evaluated. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Tabelle C Botrytis - Test (Bohne) / protektiv Table C Botrytis test (bean) / protective
Botrytis - Test (Bohne) / protektiv Botrytis test (bean) / protective
Beispiel DExample D
Puccinia-Test (Weizen) / kurativPuccinia test (wheat) / curative
Lösungsmittel: 50 Gewichtsteile N,N-DimethylacetamidSolvent: 50 parts by weight of N, N-dimethylacetamide
Emulgator: 1 Gewichtsteile 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf kurative Wirksamkeit werden junge Pflanzen mit einer Konidiensuspension von Puccinia recondita besprüht. Die Pflanzen verbleiben 48 Stunden bei 20°C und 100 % relativer Luftfeuchtigkeit in einer Inkubationskabine. Anschließend werden die Pflanzen mit der Wirkstoff- Zubereitung in der angegebenen Aufwandmenge besprüht.To test for curative effectiveness, young plants are sprayed with a conidia suspension of Puccinia recondita. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours. The plants are then sprayed with the preparation of active compound in the application rate indicated.
Die Pflanzen werden dann in einem Gewächshaus bei einer Temperatur von ca. 20°C und einer relativen Luftfeuchtigkeit von 80 % aufgestellt, um die Entwicklung von Rostpusteln zu begünstigen.The plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.
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 kein Befall beobachtet wird. Evaluation is carried out 8 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Tabelle D Puccinia-Test (Weizen) / kurativ Table D Puccinia test (wheat) / curative
Puccinia-Test (Weizen) / kurativ Puccinia test (wheat) / curative
Beispiel EExample E
Sphaerofheca-Test (Gurke) / protektivSphaerofheca test (cucumber) / protective
Lösungsmittel: 49 Gewichtsteile N, N-DimethylformamidSolvent: 49 parts by weight of N, N-dimethylformamide
Emulgator: 1 Gewichtsteü 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
Zur Prüfung auf protektive Wirksamkeit bespritzt man junge Gurkenpflanzen mit der Wirkstoffzubereitung in der angegebenen Aufwandmenge. 1 Tag nach der Behandlung werden die Pflanzen mit einer Sporensuspension von Sphaerotheca fuliginea inokuliert. Anschließend werden die Pflanzen in einem Gewächshaus bei 70 % relativer Luftfeuchtigkeit und einer Temperatur von 23 °C aufgestellt.To test for protective effectiveness, young cucumber plants are sprayed with the preparation of active compound in the stated application rate. 1 day after the treatment, the plants are inoculated with a spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at 70% relative atmospheric humidity and a temperature of 23 ° 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. Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
Tabelle ETable E
Sphaerotheca-Test (Gurke) / protektiv Sphaerotheca test (cucumber) / protective

Claims

Patentansprüche Patent claims
1. Isopentylcarboxanilide der Formel (I)1. Isopentylcarboxanilides of the formula (I)
in welcher in which
steht, wobei die mit * markierte Bindung mit dem Amid verbunden ist, während die mit # markierte Bindung mit der Alkylseitenkette verknüpft ist, R1 für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkylsulfinyl, C C6-Alkylsulfonyl, Q-Q- Alkoxy-C C4-alkyl, C3-C8-Cycloalkyl; C C6-Halogenalkyl, Q-Q-Halogenalkyl- thio, Cι-C4-Halogenalkylsulfϊnyl, Cι-C -Halogenalkylsulfonyl, Halogen-Q-Q- alkoxy-Cι-C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Cι-C3-alkyl, (Q-Q-Alkyl)carbonyl-Q-Q- alkyl, (Cι-C3-Alkoxy)carbonyl-Cι-C3-alkyl; Halogen-(Q-Q-alkyl)carbonyl-Q-Q- alkyl, Halogen-(Cι-C3-alkoxy)carbonyl-Cι-C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)car- bonyl, (C3-C8-Cycloalkyl)carbonyl; (Q-Q-Halo- genalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyl)carbonyl, (Q-Q-Halo- gencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, -CONR5R6 oder -CH2NR7R8 steht, R2 für Wasserstoff, Fluor, Chlor, Methyl oder Trifluormethyl steht, R3 für Wasserstoff, Halogen, C C8-Alkyl, Cι-C8-Halogenalkyl steht, R4 für Wasserstoff, C C8-Alkyl, CrC8-Alkoxy, Q-Q-Alkoxy-Q-Q-alkyl, Q-Q- Cycloalkyl; Cι-C6-Halogenalkyl, CrC6-Halogenalkoxy, Halogen-Cι-C4-alkoxy-Cι- C4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht, R5 und R6 unabhängig voneinander jeweils für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkoxy- Q-Q-alkyl, Q-Q-Cycloalkyl; Q-C8-Fϊalogenalkyl, Halogen-Q-Q-alkoxy-Q-Q- alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,stands, where the bond marked * is linked to the amide while the bond marked # is linked to the alkyl side chain, R 1 for hydrogen, QQ-alkyl, QQ-alkylsulfinyl, CC 6 -alkylsulfonyl, QQ-alkoxy-C C 4 - alkyl, C3 -C8 cycloalkyl; CC 6 -haloalkyl, QQ-haloalkyl-thio, Cι-C 4 -haloalkylsulfϊnyl, Cι-C -haloalkylsulfonyl, halogen-QQ-alkoxy-Cι-C 4 -alkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine -, chlorine and/or bromine atoms; Formyl, formyl-Cι-C 3 -alkyl, (QQ-alkyl)carbonyl-QQ-alkyl, (Cι-C 3 -alkoxy)carbonyl-Cι-C 3 -alkyl; Halogen-(QQ-alkyl)carbonyl-QQ-alkyl, halogen-(Cι-C 3 -alkoxy)carbonyl-Cι-C 3 -alkyl, each with 1 to 13 fluorine, chlorine and/or bromine atoms; (QQ-alkyl)carbonyl, (QQ-alkoxy)carbonyl, (QQ-alkoxy-QQ-alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (QQ-haloalkoxy)carbonyl, (halogen-QQ-alkoxy-QQ-alkyl)carbonyl, (QQ-halocycloalkyl)carbonyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; or -C(=O)C(=O)R 4 , -CONR 5 R 6 or -CH 2 NR 7 R 8 , R 2 is hydrogen, fluorine, chlorine, methyl or trifluoromethyl, R 3 is hydrogen, halogen , CC 8 -alkyl, Cι-C 8 -haloalkyl, R 4 is hydrogen, CC 8 -alkyl, C r C 8 -alkoxy, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; Cι-C 6 -haloalkyl, C r C 6 -haloalkoxy, halogen-Cι-C 4 -alkoxy-Cι-C 4 -alkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, R 5 and R 6 independently of one another each represent hydrogen, QQ-alkyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; QC 8 -Fϊalogenalkyl, halogen-QQ-alkoxy-QQ- alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q-Q-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 NR9 enthalten kann,R 5 and R 6 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 to 8 ring atoms, optionally substituted once or more, identically or differently by halogen or QQ-alkyl, the heterocycle having 1 or 2 further, can contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R7 und R8 unabhängig voneinander für Wasserstoff, Q-Q-Alkyl, Q-Q-Cycloalkyl; Q-Q- Halogenalkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen stehen,R 7 and R 8 independently represent hydrogen, QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms,
R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q-Q-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 NR9 enthalten kann,R 7 and R 8 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 to 8 ring atoms, optionally substituted once or more, identically or differently by halogen or QQ-alkyl, the heterocycle having 1 or 2 further, can contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R9 für Wasserstoff oder Q-Q-Alkyl steht,R 9 represents hydrogen or QQ-alkyl,
A für den Rest der Formel (AI)A for the rest of the formula (AI)
(AI) steht, in welcher R10 für Wasserstoff, Hydroxy, Formyl, Cyano, Halogen, Nitro, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Alkylthio, Q-Q-Cycloalkyl, Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, Aminocarbonyl oder Aminocarbonyl-Q-Q-alkyl steht, Rn für Wasserstoff, Halogen, Cyano, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Al- kylthio, Q-Q-Halogenalkyl oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen, steht und R12 für Wasserstoff, Q-Q-Alkyl, Hydroxy-Q-Q-alkyl, Q-Q-Alkenyl, Q-Q- Cycloalkyl, Q-Q-Alkylthio-Q-Q-alkyl, Q-Q-Alkoxy-Q-Q-alkyl, Q- Q-Halogenalkyl, Q-C4-Halogenalkylthio-Cι-C -alkyl, Q-Q-Halogenalk- oxy-Q-Q-alkyl mit jeweils 1 bis 5 Halogenatomen, oder für Phenyl steht, mit der Maßgabe, dass R10 nicht für lod steht, wenn R11 für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und R" für Wasserstoff und R12 für Methyl stehen, oder A für den Rest der Formel (A2) (A2) steht, in welcher R13 und R14 unabhängig voneinander für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen stehen und R15 für Halogen, Cyano oder Q-Q-Alkyl, oder Q-Q-Halogenalkyl oder Q- Q-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, oder(AI) says in which R 10 for hydrogen, hydroxy, formyl, cyano, halogen, nitro, QQ-alkyl, QQ-alkoxy, QQ-alkylthio, QQ-cycloalkyl, QQ-haloalkyl, QQ-haloalkoxy or QQ-haloalkylthio, each with 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-QQ-alkyl, R n is hydrogen, halogen, cyano, QQ-alkyl, QQ-alkoxy, QQ-alkylthio, QQ-haloalkyl or QQ-haloalkylthio, each with 1 to 5 halogen atoms, and R 12 is Hydrogen, QQ-alkyl, hydroxy-QQ-alkyl, QQ-alkenyl, QQ-cycloalkyl, QQ-alkylthio-QQ-alkyl, QQ-alkoxy-QQ-alkyl, Q-Q-haloalkyl, QC 4 -haloalkylthio-Cι-C -alkyl, QQ-haloalk-oxy-QQ-alkyl, each with 1 to 5 halogen atoms, or represents phenyl, with the proviso that R 10 does not represent iodine when R 11 represents hydrogen, and with the proviso that R 10 does not represent trifluoromethyl or difluoromethyl if R 3 and R "are hydrogen and R 12 is methyl, or A represents the remainder of the formula (A2) (A2), in which R 13 and R 14 independently represent hydrogen, halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 15 represents halogen, cyano or QQ-alkyl, or QQ-haloalkyl or Q-Q-haloalkoxy with 1 each up to 5 halogen atoms, or
A für den Rest der Formel (A3)A for the rest of the formula (A3)
(A3) steht, in welcher R16 und R17 unabhängig voneinander für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen stehen und R1S für Wasserstoff, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A4)(A3) says in which R 16 and R 17 independently represent hydrogen, halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 1S represents hydrogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, or A represents the remainder the formula (A4)
(A4) steht, in welcher R19 für Wasserstoff, Halogen, Hydroxy, Cyano, Q-Q-Alkyl, Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Halogenatomen steht, oder(A4) says in which R 19 represents hydrogen, halogen, hydroxy, cyano, QQ-alkyl, QQ-haloalkyl, QQ-haloalkoxy or QQ-haloalkylthio, each with 1 to 5 halogen atoms, or
A für den Rest der Formel (A5)A for the rest of the formula (A5)
(A5) steht, in welcher R20 für Halogen, Hydroxy, Cyano, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Alkyl- thio, Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio oder Q-Q-Halogen- alkoxy mit jeweils 1 bis 5 Halogenatomen steht und R21 für Wasserstoff, Halogen, Cyano, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q- Alkylthio, Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen, Q-Q-Alkylsulfϊnyl oder Q-Q-Alkylsulfonyl steht, oder A für den Rest der Formel (A6)(A5) says in which R 20 represents halogen, hydroxy, cyano, QQ-alkyl, QQ-alkoxy, QQ-alkylthio, QQ-haloalkyl, QQ-haloalkylthio or QQ-haloalkoxy, each with 1 to 5 halogen atoms and R 21 represents hydrogen, halogen , Cyano, QQ-alkyl, QQ-alkoxy, QQ-alkylthio, QQ-haloalkyl, QQ-haloalkoxy each with 1 to 5 halogen atoms, QQ-alkylsulfϊnyl or QQ-alkylsulfonyl, or A for the rest of the formula (A6)
(A6) steht, oder(A6) stands, or
A für den Rest der Formel (A7)A for the rest of the formula (A7)
(A7) steht, in welcher R22 für Cι-C4-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A8)(A7) says in which R 22 is Cι-C 4 alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, or A is the rest of the formula (A8)
(A8) steht, in welcher R23 für Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A9) (A9) steht, in welcher R24 und R25 unabhängig voneinander für Wasserstoff, Halogen, Amino, Q-Q- Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht und R26 für Wasserstoff, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 to 5 Halogenatomen steht, mit der Maßgabe, dass R24 und R26 nicht gleichzeitig für Methyl stehen, wenn R25 für Wasserstoff steht, oder(A8) says in which R 23 represents QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, or A represents the rest of the formula (A9) (A9), in which R 24 and R 25 independently represent hydrogen, halogen, amino, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 26 represents hydrogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, with the proviso that R 24 and R 26 do not simultaneously represent methyl when R 25 represents hydrogen, or
A für den Rest der Formel (A 10)A for the rest of the formula (A 10)
(A10) steht, in welcher R27 und R28 unabhängig voneinander für Wasserstoff, Halogen, Amino, Nitro, Q- Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen stehen und R29 für Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (AI 1) (AI 1) steht, in welcher R30 für Wasserstoff, Halogen, Amino, Q-Q-Alkylamino, Di-(Q-Q-alkyl)- amino, Cyano, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenato- men steht und R31 für Halogen, Hydroxy, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Cycloalkyl, Q-Q- Halogenalkyl oder Q-C -Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, mit der Maßgabe, dass R31 nicht für Trifluormethyl, Difluormethyl oder Methyl steht, wenn R3 für Wasserstoff und R30 für Methyl stehen, oder A für den Rest der Formel (A12) (A12) steht, in welcher R32 für Wasserstoff, Halogen, Amino, Q-Q-Alkylamino, Di-(Q-Q-alkyl)- amino, Cyano, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht und R33 für Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder A für den Rest der Formel (A13)(A10) says in which R 27 and R 28 independently represent hydrogen, halogen, amino, nitro, Q-Q-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 29 represents halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms , or A stands for the remainder of the formula (AI 1) (AI 1), in which R 30 represents hydrogen, halogen, amino, QQ-alkylamino, di-(QQ-alkyl)-amino, cyano, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 31 represents halogen, hydroxy, QQ- alkyl, QQ-alkoxy, QQ-cycloalkyl, QQ-haloalkyl or QC-haloalkoxy, each with 1 to 5 halogen atoms, with the proviso that R 31 does not represent trifluoromethyl, difluoromethyl or methyl when R 3 is hydrogen and R 30 is Methyl, or A represents the rest of the formula (A12) (A12), in which R 32 is hydrogen, halogen, amino, QQ-alkylamino, di-(QQ-alkyl)-amino, cyano, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms and R 33 is halogen, QQ-alkyl or QQ- Haloalkyl with 1 to 5 halogen atoms, or A is the rest of the formula (A13)
(AI 3) steht, in welcher R34 für Wasserstoff oder Q-Q-Alkyl steht und R35 für Halogen oder Q-Q-Alkyl steht, oder A für den Rest der Formel (AI 4) (A14) steht, in welcher R36 für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, oder für den Rest der Formel (AI 5)(AI 3) says in which R 34 is hydrogen or QQ-alkyl and R 35 is halogen or QQ-alkyl, or A is the rest of the formula (AI 4) (A14), in which R 36 represents hydrogen, halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, or for the rest of the formula (AI 5)
(AI 5) steht, in welcher R ,3"7 für Halogen, Hydroxy, Q-Q-Alkyl, C Q-Alkoxy, Q-Q-Alkylthio, Q-Q- Halogenalkyl, Q-Q-Halogenalkyltbio oder C]-C4-Halogenalkoxy mit jeweils 1 bis 5 Halogenatomen steht, oder für den Rest der Formel (AI 6)(AI 5) says in which R,3"7 represents halogen, hydroxy, QQ-alkyl, C Q-alkoxy, QQ-alkylthio, QQ-haloalkyl, QQ-haloalkyltbio or C]-C 4 -haloalkoxy, each with 1 to 5 halogen atoms, or for the rest the formula (AI 6)
(AI 6) steht, in welcher R38 für Wasserstoff, Cyano, Q-Q-Alkyl, Q-Q-Halogenalkyl mit 1 bis 5 Halo- genatomen, Q-Q-Alkoxy-Q-Q-alkyl, Hydroxy-Q-Q-alkyl, Q-Q-Alkyl- sulfonyl, Di(Cι-C4-alkyl)aminosulfonyl, Cι-C6-Alkylcarbonyl oder für jeweils gegebenenfalls substituiertes Phenylsulfonyl oder Benzoyl steht, R39 für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R40 für Wasserstoff, Halogen, Cyano, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, R41 für Wasserstoff, Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl mit 1 bis 5 Halogenatomen steht, mit der Maßgabe, dass R40 nicht für Trifluormethyl steht, oder(AI 6) says in which R 38 for hydrogen, cyano, QQ-alkyl, QQ-haloalkyl with 1 to 5 halogen atoms, QQ-alkoxy-QQ-alkyl, hydroxy-QQ-alkyl, QQ-alkyl-sulfonyl, di (Cι-C 4 -alkyl )aminosulfonyl, Cι-C 6 alkylcarbonyl or represents optionally substituted phenylsulfonyl or benzoyl, R 39 represents hydrogen, halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, R 40 represents hydrogen, halogen, cyano, QQ -Alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, R 41 represents hydrogen, halogen, QQ-alkyl or QQ-haloalkyl with 1 to 5 halogen atoms, with the proviso that R 40 does not represent trifluoromethyl, or
A für den Rest der Formel (AI 7)A for the rest of the formula (AI 7)
(AI 7) steht, in welcher R2 für Q-Q-Alkyl steht.(AI 7) says in which R2 stands for QQ-alkyl.
Isopentylcarboxanilide der Formel (I) gemäß Anspruch 1, in welcherIsopentylcarboxanilides of the formula (I) according to claim 1, in which
steht, L-l L-2 L-3 L-4 wobei die mit * markierte Bindung mit dem Amid verbunden ist, während die mit # markierte Bindung mit der Alkylseitenkette verknüpft ist,stands, Ll L-2 L-3 L-4 where the bond marked * is linked to the amide while the bond marked # is linked to the alkyl side chain,
R1 für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkylsulfinyl, Q-Q-Alkylsulfonyl, Q-Q- Alkoxy-Q-Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halogenalkylsulfϊnyl, Q-C -Halogenalkylsulfonyl, Halogen-Q-Q-alkoxy-Q- Q-alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-Q-Alkyl)carbonyl-Q-Q-alkyl, (Q-Q- Alkoxy)carbonyl-Q-Q-alkyl; Halogen-(Q-Q-alkyl)carbonyl-Q-Q-alkyl, Halogen- (Q-Q-alkoxy)carbonyl-Q-C3-aιkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)car- bonyl, (Q-Q-Cycloalkyl)carbonyl; (Cι-C4-Halogenalkyl)carbonyl, (Q-Q-Halo- genalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyι)carbonyl, (Q-Q-Halo- gencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=0)R4, -CONR5R6 oder -CH2NR7R8 steht,R 1 for hydrogen, QQ-alkyl, QQ-alkylsulfinyl, QQ-alkylsulfonyl, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfϊnyl, QC -haloalkylsulfonyl, halogen-QQ-alkoxy-Q-Q-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-QQ-alkyl, (QQ-alkyl)carbonyl-QQ-alkyl, (QQ-alkoxy)carbonyl-QQ-alkyl; Halogen-(QQ-alkyl)carbonyl-QQ-alkyl, halogen-(QQ-alkoxy)carbonyl-QC 3 -aιkyl, each with 1 to 13 fluorine, chlorine and/or bromine atoms; (QQ-alkyl)carbonyl, (QQ-alkoxy)carbonyl, (QQ-alkoxy-QQ-alkyl)carbonyl, (QQ-cycloalkyl)carbonyl; (Cι-C 4 -haloalkyl)carbonyl, (QQ-haloalkoxy)carbonyl, (halogen-QQ-alkoxy-QQ-alkyι)carbonyl, (QQ-halogencycloalkyl)carbonyl, each with 1 to 9 fluoro-, chloro- and/or bromine atoms; or -C(=O)C(=0)R 4 , -CONR 5 R 6 or -CH 2 NR 7 R 8 ,
R2 für Wasserstoff, Fluor, Chlor, Methyl oder Trifluormethyl steht,R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
R3 für Wasserstoff, Fluor, Chlor, Brom, lod, Q-Q-Alkyl, Q-Q-Halogenalkyl mit 1 bis 13 Fluor-, Chlor- und/oder Bromatomen steht,R 3 represents hydrogen, fluorine, chlorine, bromine, iodine, QQ-alkyl, QQ-haloalkyl with 1 to 13 fluorine, chlorine and/or bromine atoms,
R4 für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkoxy, Q-Q-Alkoxy-Q-Q-alkyl, Q-Q- Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkoxy, Halogen-Q-Q-alkoxy-Q- Q-alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen steht,R 4 for hydrogen, QQ-alkyl, QQ-alkoxy, QQ-alkoxy-QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkoxy, halogen-QQ-alkoxy-Q-Q-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 unabhängig voneinander jeweils für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkoxy-Q- Q-alkyl, Q-Q-Cycloalkyl; Q-C4-Halogenalkyl, Halogen-Q-Q-alkoxy-Q-Q-alkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen,R 5 and R 6 independently each represent hydrogen, QQ-alkyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QC 4 -haloalkyl, halogen-QQ-alkoxy-QQ-alkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms,
R5 und R6 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach bis vierfach, gleich oder verschieden durch Halogen oder Q-Q-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 NR9 enthalten kann,R 5 and R 6 also, together with the nitrogen atom to which they are bonded, form a saturated heterocycle with 5 to 8 ring atoms, optionally mono- to quadruple-substituted, identically or differently substituted by halogen or QQ-alkyl, the heterocycle containing 1 or 2 further, can contain non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R7 und R8 unabhängig voneinander für Wasserstoff, Q-Q-Alkyl, Q-Q-Cycloalkyl; Q-Q- Halogenalkyl, Q-Q-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen stehen, R7 und R8 außerdem gemeinsam mit dem Stickstoffatom, an das sie gebunden sind, einen gegebenenfalls einfach oder mehrfach, gleich oder verschieden durch Halogen oder Q-Q-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 NR9 enthalten kann,R 7 and R 8 independently represent hydrogen, QQ-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-halocycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms, R 7 and R 8 also together with the nitrogen atom to which they are bonded, optionally single or multiple, identical or different halogen or QQ-alkyl substituted saturated heterocycle with 5 to 8 ring atoms, whereby the heterocycle can contain 1 or 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 9 ,
R9 für Wasserstoff oder Q-Q-Alkyl steht,R 9 represents hydrogen or QQ-alkyl,
A für den Rest der Formel (AI)A for the rest of the formula (AI)
(AI) steht, in welcher R10 für Wasserstoff, Hydroxy, Formyl, Cyano, Fluor, Chlor, Brom, lod, Methyl, Ethyl, iso-Propyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Cyclopropyl, Q- Q-Halogenalkyl, Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und oder Bromatomen, Trifluormethylthio, Difluormethylthio, Aminocarbo- nyl, Aminocarbonylmethyl oder Aminocarbonylethyl steht, Rπ für Wasserstoff, Chlor, Brom, lod, Methyl, Ethyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, steht und R12 für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen, Hydroxymethyl, Hydroxyethyl, Cyclopropyl, Cyclopentyl, Cyclohexyl oder Phenyl steht, mit der Maßgabe, dass R10 nicht für lod steht, wenn R11 für Wasserstoff steht, und mit der Maßgabe, dass R10 nicht für Trifluormethyl oder Difluormethyl steht, wenn R3 und Rn für Wasserstoff und R12 für Methyl stehen, oder A für den Rest der Formel (A2)(AI) says in which R 10 for hydrogen, hydroxy, formyl, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, iso-propyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, Q-Q-haloalkyl, QQ-haloalkoxy each with 1 to 5 Fluorine, chlorine and or bromine atoms, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl, R π is hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, and R 12 represents hydrogen, methyl, ethyl, n-propyl, iso-propyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl , cyclohexyl or phenyl, with the proviso that R 10 does not represent iodine when R 11 represents hydrogen, and with the proviso that R 10 does not represent trifluoromethyl or difluoromethyl when R 3 and R n represent hydrogen and R 12 represents methyl, or A represents the rest of the formula (A2)
(A2) steht, in welcher R13 und R14 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen und R15 für Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, Q-Q-Halogenalkyl oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (A3) (A3) steht, in welcher R16 und R17 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen und R18 für Wasserstoff, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (A4)(A2) says in which R 13 and R 14 independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms and R 15 represents fluorine, chlorine, bromine, iodine, cyano, methyl , ethyl, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, or A is the rest of the formula (A3) (A3) says in which R 16 and R 17 independently represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms and R 18 represents hydrogen, methyl, ethyl or QQ-haloalkyl with 1 up to 5 fluorine, chlorine and/or bromine atoms, or A represents the rest of the formula (A4)
(A4) steht, in welcher R19 für Wasserstoff, Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Q-Q-Alkyl, Q- Q-Halogenalkyl, Q-Q-Halogenalkoxy oder Q-Q-Halogenalkylthio mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder(A4) says in which R 19 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, Q-Q-haloalkyl, QQ-haloalkoxy or QQ-haloalkylthio, each with 1 to 5 fluorine, chlorine and / or bromine atoms, or
A für den Rest der Formel (A5)A for the rest of the formula (A5)
(A5) steht, in welcher R20 für Fluor, Chlor, Brom, lod, Hydroxy, Cyano, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Q-Q- Halogenalkyl oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht und R21 für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Q-Q-Halogenalkyl oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen, Q-Q-Alkyl- sulfϊnyl oder Q-Q-Alkylsulfonyl steht, oder A für den Rest der Formel (A6) (A6) steht, oder(A5) says in which R 20 for fluorine, chlorine, bromine, iodine, hydroxy, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms and R 21 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, QQ -Alkyl-sulfϊnyl or QQ-alkylsulfonyl, or A stands for the rest of the formula (A6) (A6), or
A für den Rest der Formel (A7) (A7) steht, in welcher R22 für Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (A8) (A8) steht, in welcher R23 für Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (A9) (A9) steht, in welcher R24 und R25 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Amino, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht und R26 für Wasserstoff, Fluor, Chlor, Brom, lod, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und oder Bromatomen, mit der Maßgabe, dass R24 und R26 nicht gleichzeitig für Methyl stehen, wenn R2S für Wasserstoff steht, oder A für den Rest der Formel (A 10)A for the rest of the formula (A7) (A7) says in which R 22 represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents the rest of the formula (A8) (A8), in which R 23 represents methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents the rest of the formula (A9) (A9), in which R 24 and R 25 independently represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms and R 26 represents hydrogen, fluorine, chlorine, bromine, iodine , methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and or bromine atoms, with the proviso that R 24 and R 26 do not simultaneously represent methyl when R 2S represents hydrogen, or A represents the rest of the formula ( A 10)
(A10) steht, in welcher R27 und R28 unabhängig voneinander für Wasserstoff, Fluor, Chlor, Brom, Amino, Nitro, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen stehen und R29 für Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (AI 1) (AI 1) steht, in welcher R30 für Wasserstoff, Fluor, Chlor, Brom, Amino, Q-Q-Alkylamino, Di(Q-Q- alkyhamino, Cyano, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht und R31 für Fluor, Chlor, Brom, Hydroxy, Methyl, Ethyl, Methoxy, Ethoxy, Cyclopropyl, Q-C2-Halogenalkyl oder Q-Q-Halogenalkoxy mit 1 bis 5 Fluor, Chlor und oder Bromatomen steht, mit der Maßgabe, dass R31 nicht für Trifluormethyl, Difluormethyl oder Methyl steht, wenn R3 für Wasserstoff und R30 für Methyl stehen, oder(A10) says in which R 27 and R 28 independently represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms and R 29 represents fluorine, chlorine, bromine, methyl , ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, or A is the rest of the formula (AI 1) (AI 1) says in which R 30 is hydrogen, fluorine, chlorine, bromine, amino, QQ-alkylamino, di (QQ-alkyhamino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms and R 31 is fluorine, Chlorine, bromine, hydroxy, methyl, ethyl, methoxy, ethoxy, cyclopropyl, QC 2 -haloalkyl or QQ-haloalkoxy with 1 to 5 fluorine, chlorine and or bromine atoms, with the proviso that R 31 does not represent trifluoromethyl, difluoromethyl or methyl is when R 3 is hydrogen and R 30 is methyl, or
A für den Rest der Formel (A 12) (AI 2) steht, in welcher R32 für Wasserstoff, Fluor, Chlor, Brom, Amino, Q-Q-Alkylamino, Di(Q-Q- alkyl)amino, Cyano, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht und R33 für Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oderA stands for the remainder of the formula (A 12) (AI 2), in which R 32 represents hydrogen, fluorine, chlorine, bromine, amino, QQ-alkylamino, di(QQ-alkyl)amino, cyano, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms and R 33 represents Fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and / or bromine atoms, or
A für den Rest der Formel (A 13 ) (A13) steht, in welcher R34 für Wasserstoff, Methyl oder Ethyl steht und R35 für Fluor, Chlor, Brom, Methyl oder Ethyl steht, oder A für den Rest der Formel (AI 4) (AI 4) steht, in welcher R36 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (AI 5) (AI 5) steht, in welcher R37 für Fluor, Chlor, Brom, lod, Hydroxy, Q-Q-Alkyl, Methoxy, Ethoxy, Methylthio, Ethylthio, Difluormethylthio, Trifluormethylthio, Q-Q-Halogenalkyl oder Q-Q-Halogenalkoxy mit jeweils 1 bis 5 Fluor, Chlor und/oder Bromatomen steht, oder A für den Rest der Formel (AI 6)A represents the remainder of the formula (A 13 ) (A13), in which R 34 represents hydrogen, methyl or ethyl and R 35 represents fluorine, chlorine, bromine, methyl or ethyl, or A represents the rest of the formula (AI 4) (AI 4), in which R 36 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, or A represents the rest of the formula (AI 5) (AI 5) says in which R 37 represents fluorine, chlorine, bromine, iodine, hydroxy, QQ-alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, QQ-haloalkyl or QQ-haloalkoxy, each with 1 to 5 fluorine, chlorine and / or bromine atoms, or A for the rest of the formula (AI 6)
(AI 6) steht, in welcher R38 für Wasserstoff, Methyl, Ethyl, Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen, Q-Q-Alkoxy-Q-Q-alkyl, Hydroxymethyl, Hydroxyethyl, methylsulfonyl oder Dimethylaminosulfonyl steht, R39 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen steht, R40 für Wasserstoff, Fluor, Chlor, Brom, Cyano, Methyl, Ethyl, iso-Propyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor-, Chlor- und/oder Bromatomen steht, R41 für Wasserstoff, Fluor, Chlor, Brom, Methyl, Ethyl oder Q-Q-Halogenalkyl mit 1 bis 5 Fluor, Chlor und oder Bromatomen steht, mit der Maßgabe, dass R40 nicht für Trifluormethyl steht, oder A für den Rest der Formel (A 17)(AI 6) says in which R 38 is hydrogen, methyl, ethyl, QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, QQ-alkoxy-QQ-alkyl, hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, R 39 is hydrogen, fluorine, Chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, R 40 represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, R 41 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or QQ-haloalkyl with 1 to 5 fluorine, chlorine and/or bromine atoms, with the proviso that R 40 is not trifluoromethyl, or A is the rest of the formula (A 17)
(AI 7) steht, in welcher R42 für Methyl, Ethyl, n-Propyl oder iso-Propyl steht.(AI 7) says in which R 42 represents methyl, ethyl, n-propyl or iso-propyl.
3. Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 oder 2, in welcher L für L-l steht.3. Isopentylcarboxanilides of the formula (I) according to points 1 or 2, in which L stands for L-l.
4. Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 oder 2, in welcher L für L-2 steht.4. Isopentylcarboxanilides of the formula (I) according to claim 1 or 2, in which L stands for L-2.
5. Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 oder 2, in welcher R1 für Wasserstoff, Formyl oder -C(=O)C(=O)R4 steht, wobei R4 die in Anspruch 1 oder 2 angegebenen Bedeutungen hat. 5. Isopentylcarboxanilides of the formula (I) according to claim 1 or 2, in which R 1 represents hydrogen, formyl or -C(=O)C(=O)R 4 , where R 4 has the meanings given in claim 1 or 2 .
6. Isopentylcarboxanilide der Formel (I) gemäß Anspruch 1 oder 2, in welcher A für AI steht.6. Isopentylcarboxanilides of the formula (I) according to claim 1 or 2, in which A stands for Al.
7. Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 oder 2, in welcher R3 für Wasserstoff steht.7. Isopentylcarboxanilides of the formula (I) according to points 1 or 2, in which R 3 represents hydrogen.
8. Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 oder 2, in welcher R3 für Halogen, Q-Q-Alkyl oder Q-Q-Halogenalkyl steht.8. Isopentylcarboxanilides of the formula (I) according to points 1 or 2, in which R 3 represents halogen, QQ-alkyl or QQ-haloalkyl.
9. Verfahren zum Herstellen der Verbindungen der Formel (I) gemäß Ansprach 1, dadurch gekennzeichnet, dass man a) Carbonsäure-Derivate der Formel (11)9. A process for producing the compounds of the formula (I) according to claim 1, characterized in that a) carboxylic acid derivatives of the formula (11)
A X X 1 <®> in welcher A die in Anspruch 1 angegebenen Bedeutungen hat und X1 für Halogen oder Hydroxy steht, mit einem Anilin-Derivat der Formel (JE)AXX 1 <® > in which A has the meanings given in claim 1 and X 1 represents halogen or hydroxy, with an aniline derivative of the formula (JE)
in welcher L, R1 und R3 die oben angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Katalysators, gegebenenfalls in Gegenwart eines Kondensationsmittels, gegebenenfalls in Gegenwart eines Säurebindemittels und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder b) Isopentylcarboxanilide der Formel (I-a) in which L, R 1 and R 3 have the meanings given above, optionally in the presence of a catalyst, optionally in the presence of a condensation agent, optionally in the presence of an acid binding agent and optionally in the presence of a diluent, or b) isopentylcarboxanilides of the formula (Ia)
in welcher L, A und R3 die in Anspruch 1 angegebenen Bedeutungen haben mit Halogeniden der Formel (IV) R1-A— X2 (IV) in welcher X2 für Chlor, Brom oder lod steht, R1_A für Q-Q-Alkyl, Q-Q-Alkylsulfϊnyl, Q-Q-Alkylsulfonyl, Q-Q-Alkoxy-Q- Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halogenalkylsulfϊnyl, Q-Q-Halogenalkylsulfonyl, Halogen-Q-Q- alkoxy-Q-Q-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Foimyl-Q-Q-alkyl, (Q-Q-Alkyl)- carbonyl-Cι-C3-alkyl, (Q-Q-Alkoxy)carbonyl-Q-Q-alkyl; Halogen-(Q-Q- alkyl)carbonyl-CrC3-alkyl, Halogen-(Q-Q-alkoxy)carbonyl-Q-Q-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-alkyl)- carbonyl, (C3-C8-Cycloalkyl)carbonyl; (CrC6-Halogenalkyl)carbonyl, (Q-Q- Halogenalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyOcarbonyl, (Q- C8-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, CONR5R6 oder -CH2NR7R8 steht, wobei R4, R5, R6, R7 und R8 die in Anspruch 1 angegebenen Bedeutungen haben, in Gegenwart einer Base und in Gegenwart eines Verdünnungsmittels umsetzt, oder c) Isopenton-Derivate der Formel (V) in which L, A and R 3 have the meanings given in claim 1 with halides of the formula (IV) R 1 - A - X 2 (IV) in which X 2 for chlorine, brom or lod stands, r 1_a for qq-alkyl, qq-alkylsulfϊnyl, qq-alkylsulfonyl, QQ-alkoxy-q-alkyl, qq-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfϊnyl, QQ-haloalkylsulfonyl, halogen-QQ-alkoxy-QQ-alkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms; formyl, foimyl-QQ-alkyl, (QQ-alkyl)-carbonyl-Cι-C 3 -alkyl, (QQ-alkoxy)carbonyl-QQ-alkyl; Halogen-(QQ-alkyl)carbonyl-C r C 3 -alkyl, halogen-(QQ-alkoxy)carbonyl-QQ-alkyl, each with 1 to 13 fluorine, chlorine and/or bromine atoms; (QQ-alkyl)carbonyl, (QQ-alkoxy)carbonyl, (QQ-alkoxy-QQ-alkyl)-carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (C r C 6 -haloalkyl)carbonyl, (QQ-haloalkoxy)carbonyl, (halogen-QQ-alkoxy-QQ-alkyOcarbonyl, (Q-C 8 -halocycloalkyl)carbonyl, each with 1 to 9 fluorine, chlorine and / or Bromine atoms; or -C(=O)C(=O)R 4 , CONR 5 R 6 or -CH 2 NR 7 R 8 , where R 4 , R 5 , R 6 , R 7 and R 8 are those in claim 1 have the meanings given, in the presence of a base and in the presence of a diluent, or c) isopentone derivatives of the formula (V)
in welcher R1, R2, R3 und A die in Anspruch 1 angegebenen Bedeutungen haben, mit Hydrazin (oder Hydrazin-hydrat) in Gegenwart einer Base und gegebenenfalls in Gegenwart eines Verdünnungsmittels umsetzt, oder d) Isopenten-Derivate der Formel (VT) in which R 1 , R 2 , R 3 and A have the meanings given in claim 1, reacted with hydrazine (or hydrazine hydrate) in the presence of a base and optionally in the presence of a diluent, or d) isopentene derivatives of the formula (VT )
in welcher R1, R2, R3 und A die in Anspruch 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators hydriert, oder e) Isopentin-Derivate der Formel (VE) in which R 1 , R 2 , R 3 and A have the meanings given in claim 1, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst, or e) isopentin derivatives of the formula (VE)
in welcher R1, R2, R3 und A die in Ansprach 1 angegebenen Bedeutungen haben, gegebenenfalls in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Katalysators hydriert. in which R 1 , R 2 , R 3 and A have the meanings given in claim 1, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst.
10. Mittel zum Bekämpfen unerwünschter Mikroorganismen, gekennzeichnet durch einen Gehalt an mindestens einem Isopentylcarboxanilid der Formel (1) gemäß Ansprach 1 neben Streckmitteln und/oder oberflächenaktiven Stoffen.10. Agent for combating undesirable microorganisms, characterized by a content of at least one isopentylcarboxanilide of the formula (1) according to address 1 in addition to extenders and / or surface-active substances.
11. Verwendung von Isopentylcarboxanihden der Formel (I) gemäß Ansprach 1 zum Bekämpfen unerwünschter Mikroorganismen.11. Use of isopentylcarboxanids of the formula (I) according to address 1 for combating undesirable microorganisms.
12. Verfahren zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Isopentylcarboxanilide der Formel (I) gemäß Ansprach 1 auf die Mikroorganismen und/oder deren Lebensraum ausbringt.12. A method for combating undesirable microorganisms, characterized in that isopentylcarboxanilides of the formula (I) according to paragraph 1 are applied to the microorganisms and / or their habitat.
13. Verfahren zum Herstellen von Mitteln zum Bekämpfen unerwünschter Mikroorganismen, dadurch gekennzeichnet, dass man Isopentylcarboxanilide der Fonnel (I) gemäß Anspruch 1 mit Streckmitteln und/oder oberflächenaktiven Stoffen vermischt.13. A process for producing agents for combating undesirable microorganisms, characterized in that isopentylcarboxanilides of the formula (I) according to claim 1 are mixed with extenders and/or surface-active substances.
14. Anilin-Derivate der Formel (ITI-b)14. Aniline derivatives of formula (ITI-b)
in welcher a) R B für Q-Q-Alkyl, Q-Q-Alkylsulfmyl, Q-Q-Alkylsulfonyl, Q-Q-Alkoxy-Q- Q-alkyl, Q-Q-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Q-Q-Halogenalkylsulfϊnyl, Q-Q-Halogenalkylsulfonyl, Halogen-Q-Q- alkoxy-CrC4-alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-Q-Alkyl)- carbonyl-Q-Q-alkyl, (Q-Q-Alkoxy)carbonyl-Q-Q-alkyl; Halogen-(Q-Q- alkyl)carbonyl-Q-Q-alkyl, Halogen-(Cι-C3-alkoxy)carbonyl-C C3-alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und/oder Bromatomen; (Q-Q-Alkyl)carbonyl, (Q-Q-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-al- kyl)carbonyl, (C3-C8-Cycloalkyl)carbonyl; (C C6-Halogenalkyl)carbonyl, (Q-Q-Halogenalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyl)carbo- nyl, (C3-C8-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; oder -C(=O)C(=O)R4, CONR5R6 oder -CH2NR7R8 steht, und R3"B für Wasserstoff, Halogen, Q-Q-Alkyl, Q-Q-Halogenalkyl steht, oder b) R!"B für Wasserstoff, Q-Q-Alkyl, Q-Q-Alkylsulfϊnyl, Q-Q-Alkylsulfonyl, Q- C4-Alkoxy-Cι-C4-alkyl, C3-C8-Cycloalkyl; Q-Q-Halogenalkyl, Q-Q-Halogenalkylthio, Cι-C -Halogenalkylsulfϊnyl, Cι-C4-Halogenalkylsulfonyl, Ha- logen-Cι-C4-alkoxy-Cι-C -alkyl, C3-C8-Halogencycloalkyl mit jeweils 1 bis 9 Fluor-, Chlor- und/oder Bromatomen; Formyl, Formyl-Q-Q-alkyl, (Q-Q- Alkyl)carbonyl-Q-Q-alkyl, (Q-Q-Alkoxy)carbonyl-Q-Q-alkyl; Halogen- (Cι-C3-alkyl)carbonyl-Cι-C3-alkyl, Halogen-(Q-Q-alkoxy)carbonyl-Q-Q- alkyl mit jeweils 1 bis 13 Fluor-, Chlor- und oder Bromatomen; (Q-Q-Alkyl)carbonyl, (CrC8-Alkoxy)carbonyl, (Q-Q-Alkoxy-Q-Q-al- kyl)carbonyl, (C3-C8-Cycloalkyl)carbonyl; (Q-QΗalogenalkyl)carbonyl, (Q-Q-Halogenalkoxy)carbonyl, (Halogen-Q-Q-alkoxy-Q-Q-alkyrjcarbo- nyl, (C3-C8-Halogencycloalkyl)carbonyl mit jeweils 1 bis 9 Fluor-, Chlor- und oder Bromatomen; oder -C(=O)C(=O)R4, CONR5R6 oder -CH2NR7R8 steht, und R3"B für Halogen, CrC8-Alkyl, Q-C8-Halogenalkyl steht, und R2, R4, R5, R6, R7 und R8 jeweils die in Anspruch 1 angegebenen Bedeutungen haben. in which a) R B for QQ-alkyl, QQ-alkylsulfmyl, QQ-alkylsulfonyl, QQ-alkoxy-Q-Q-alkyl, QQ-cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, QQ-haloalkylsulfϊnyl, QQ-haloalkylsulfonyl, halogen-QQ-alkoxy-C r C 4 -alkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms ; formyl, formyl-QQ-alkyl, (QQ-alkyl)-carbonyl-QQ-alkyl, (QQ-alkoxy)carbonyl-QQ-alkyl; Halogen-(QQ-alkyl)carbonyl-QQ-alkyl, halogen-(Cι-C 3 -alkoxy)carbonyl-C C 3 -alkyl, each with 1 to 13 fluorine, chlorine and/or bromine atoms; (QQ-alkyl)carbonyl, (QQ-alkoxy)carbonyl, (QQ-alkoxy-QQ-alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (CC 6 -haloalkyl)carbonyl, (QQ-haloalkoxy)carbonyl, (halogen-QQ-alkoxy-QQ-alkyl)carbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl, each with 1 to 9 fluoro-, chloro- and/or bromine atoms; or -C(=O)C(=O)R 4 , CONR 5 R 6 or -CH 2 NR 7 R 8 , and R 3"B represents hydrogen, halogen, QQ-alkyl, QQ-haloalkyl, or b ) R !"B for hydrogen, QQ-alkyl, QQ-alkylsulfϊnyl, QQ-alkylsulfonyl, Q-C 4 -alkoxy-Cι-C 4 -alkyl, C 3 -C 8 -cycloalkyl; QQ-haloalkyl, QQ-haloalkylthio, Cι-C -haloalkylsulfϊnyl, Cι-C 4 -haloalkylsulfonyl, halogen-Cι-C 4 -alkoxy-Cι-C -alkyl, C 3 -C 8 -halocycloalkyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms; formyl, formyl-QQ-alkyl, (QQ-alkyl)carbonyl-QQ-alkyl, (QQ-alkoxy)carbonyl-QQ-alkyl; Halogen-(Cι-C 3 -alkyl)carbonyl-Cι-C 3 -alkyl, halogen-(QQ-alkoxy)carbonyl-QQ-alkyl, each with 1 to 13 fluorine, chlorine and/or bromine atoms; (QQ-alkyl)carbonyl, (C r C 8 -alkoxy)carbonyl, (QQ-alkoxy-QQ-alkyl)carbonyl, (C 3 -C 8 -cycloalkyl)carbonyl; (Q-QΗaloalkyl)carbonyl, (QQ-haloalkoxy)carbonyl, (halogen-QQ-alkoxy-QQ-alkyrjcarbonyl, (C 3 -C 8 -halocycloalkyl)carbonyl, each with 1 to 9 fluorine, chlorine and/or bromine atoms ; or -C(=O)C(=O)R 4 , CONR 5 R 6 or -CH 2 NR 7 R 8 , and R 3"B represents halogen, C r C 8 alkyl, QC 8 haloalkyl , and R 2 , R 4 , R 5 , R 6 , R 7 and R 8 each have the meanings given in claim 1.
15. Isopenton-Derivate der Formel (V)15. Isopentone derivatives of formula (V)
in welcher R , R , R und A die in Anspruch 1 angegebenen Bedeutungen haben. in which R, R, R and A have the meanings given in claim 1.
16. Isopenten-Derivate der Formel (VI)16. Isopentene derivatives of formula (VI)
in welcher R , R , R und A die in Anspruch 1 angegebenen Bedeutungen haben. in which R, R, R and A have the meanings given in claim 1.
17. Isopentin-Derivate der Formel (VE)17. Isopentin derivatives of formula (VE)
in welcher R1, R2 und R3 die in Ansprach 1 angegebenen Bedeutungen haben, A die in Anspruch 1 angegebenen Bedeutungen mit Ausnahme von AI hat. in which R 1 , R 2 and R 3 have the meanings given in claim 1, A has the meanings given in claim 1 with the exception of AI.
18. Alkanonaniline der Formel (X)18. Alkanoneanilines of formula (X)
in welcher R , R und R die in Ansprach 1 angegebenen Bedeutungen haben. in which R , R and R have the meanings given in address 1.
EP04790302A 2003-10-23 2004-10-12 Isopentyl carboxanilides for combating undesired micro-organisms Withdrawn EP1680407A1 (en)

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