EP1628948A1 - Difluormethylbenzanilide und deren verwendung zur bekämpfung von mikroorganismen, sowie zwischenprodukte und deren herstellung - Google Patents

Difluormethylbenzanilide und deren verwendung zur bekämpfung von mikroorganismen, sowie zwischenprodukte und deren herstellung

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Publication number
EP1628948A1
EP1628948A1 EP04732289A EP04732289A EP1628948A1 EP 1628948 A1 EP1628948 A1 EP 1628948A1 EP 04732289 A EP04732289 A EP 04732289A EP 04732289 A EP04732289 A EP 04732289A EP 1628948 A1 EP1628948 A1 EP 1628948A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
formula
chlorine
cycloalkyl
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Withdrawn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
EP04732289A
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German (de)
English (en)
French (fr)
Inventor
Ralf Dunkel
Hans-Ludwig Elbe
Jörg Nico GREUL
Benoit Hartmann
Ulrike Wachendorff-Neumann
Peter Dahmen
Karl-Heinz Kuck
Heiko Rieck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Priority claimed from DE10325438A external-priority patent/DE10325438A1/de
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1628948A1 publication Critical patent/EP1628948A1/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • 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
    • 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
    • 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
    • C07C233/76—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 doubly-bound oxygen atoms
    • 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
    • C07C233/77—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 amino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C07C63/70—Monocarboxylic acids

Definitions

  • the present invention relates to new difluoromethylbenzanilides, several processes for their preparation and their use for controlling unwanted microorganisms.
  • EP-A 0 545 099 JP-A 2001-302605, JP-A 8-176112
  • EP-A 0 554099 already includes N- (4'-fluoro-l, l'-biphenyl-2-yl) -2- (trifluoromethyl) benzamide and N- (2-5ec-butylphenyl) -2- (trifluoromethyl) ) known benzamide.
  • the effectiveness of these substances is good, but in some cases, e.g. to be desired at low application rates.
  • Difluoromethylbenzanilides have so far not become known.
  • R 1 , R 2 , R 3 and R 4 independently of one another for hydrogen, fluorine, chlorine, methyl, iso-propyl or
  • R 5 is hydrogen, CC 8 -alkyl, -C-C 6 -alkylsulfmyl, CC 6 -alkylsulfonyl, C, -C 4 -alkoxy-C ⁇ - C 4 alkyl, C 3 -C 8 cycloalkyl; -C-C 6 -haloalkyl, - -haloalkylthio, CC 4 -haloalkyl -sulfinyl, C ⁇ -C 4 -haloalkylsulfonyl, halogen-C ⁇ -C 4 -alkoxy-C ⁇ -C -alkyl, C 3 -C 8 -halo-cycloalkyl with in each case 1 to 9 fluorine, chlorine and / or bromine atoms, formyl-C 3 -alkyl, (CC 3 -alkyl) carbonyl-C 3 -alkyl, (-CC 3 alkoxy) carbon
  • Halogencycloalkyl each with 1 to 9 fluorine, chlorine and / or bromine atoms; -COR 11 stands, R 7 and R 8 independently of one another for hydrogen, -CC 8 -alkyl, CC 4 -alkoxy -CC-C 4 alkyl, C 3 -C 8 - cycloalkyl; CC 8 -haloalkyl, halo -CC -alkoxy -CC-C 4 -alkyl, C 3 -C 8 -halogenocycloal yl 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 also form a saturated or heterocycle which has 5 to 8 ring atoms and may be mono- or polysubstituted, identically or differently, by halogen or C r C 4 -alkyl, where the
  • Heterocycle 1 or 2 further, non-adjacent heteroatoms from the series oxygen,
  • R 9 and R 10 independently of one another for hydrogen, -CC 8 alkyl, C 3 -C 8 cycloalkyl; CC 8 halogen al yl, C 3 -C 3 halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms,
  • R 9 and R 10 together with the nitrogen atom to which they are attached, form a saturated heterocycle having 5 to 8 ring atoms, which is optionally mono- or polysubstituted, identically or differently, by halogen or -CC alkyl, the heterocycle 1 or can contain 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 12 ,
  • R 11 is hydrogen, CC 8 alkyl, - alkoxy, C r C 4 alkoxy-C 1 -C 4 alkyl, C 3 -C 8 cycloalkyl; C 1 -C 6 -haloalkyl, dC 6 -haloalkoxy, halogen-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 3 -C 8 - halocycloalkyl, each with 1 to 9 fluorine, chlorine and or bromine atoms, R 12 represents hydrogen or Ci-Cg-alkyl,
  • Z stands for Z ⁇ Z 2 , Z 3 or Z 4 , wherein
  • Z 1 represents phenyl which is monosubstituted to pentas, identical or differently substituted
  • Z 2 is optionally monosubstituted or polysubstituted by identical or different substituents, cycloalkyl or bicycloalkyl
  • Z 3 represents unsubstituted C 2 -C 2 o alkyl or mono- or polysubstituted, identically or differently, by halogen and / or C 3 -C 6 cycloalkyl substituted - o-alkyl, where the cycloalkyl part in turn can optionally be substituted one or more times, identically or differently, by halogen and / or C r C 4 alkyl
  • Z 4 represents C 2 -C 20 alkenyl or C 2 -C 2 o-alkynyl which is optionally mono- or polysubstituted, identically or differently, by halogen and / or C 3 -C 6 -cycloalkyl, the cycloalkyl part in turn optionally single or can be substituted several times, identically or differently by halogen and / or C 1 -C 4 alkyl, or
  • R 1 , R 2 and R 3 independently represent hydrogen or fluorine and Z and R 4 together with the carbon atoms to which they are attached form an optionally substituted 5- or 6-membered carbocyclic or heterocyclic ring. It has furthermore been found that difluoromethylbenzanilides of the formula (I) are obtained by a) difluoromethylbenzoyl derivatives of the formula (II)
  • X 1 represents chlorine or hydroxy, with aniline derivatives of the formula (HI)
  • R, R 2 , R 3 , R 4 , R and Z have the meanings given above, optionally in the presence of a catalyst, optionally in the presence of a condensing agent, optionally in the presence of an acid binder and optionally in
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above, and X 2 represents chlorine, bromine, iodine or trifluoromethyl sulfonate, with boronic acid derivatives of the formula (V)
  • a 1 and A 2 each represent hydrogen or together represent tetramethylethylene, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or c) difluoromethylbenzamide-boronic acid-D
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above, and
  • a 3 and A 4 each represent hydrogen or together represent tetramethylethylene, with phenyl derivatives of the formula (VII) X 3 - Z 1 (Q) in which Z 1 has the meanings given above and
  • X 3 represents chlorine, bromine, iodine or trifluoromethyl sulfonate, in the presence of a catalyst, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, or d) halodifluoromethylbenzanilides of the formula (TV)
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above, and X 2 represents chlorine, bromine, iodine or trifluoromethyl sulfonate, with phenyl derivatives of the formula (VII)
  • X 3 represents chlorine, bromine, iodine or trifluoromethyl sulfonate, in the presence of a palladium or nickel catalyst and in the presence of
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above and
  • X 4 stands for C 2 -C 2 o-alkenyl or C 2 -C 2 o-alkynyl which is optionally mono- or polysubstituted, identically or differently, by halogen and / or C 3 -C 6 -cycloalkyl, the cycloalkyl part in turn being optionally substituted by Halogen and / or C r C 4 alkyl may be substituted, optionally hydrogenated in the presence of a diluent and optionally in the presence of a catalyst, or f) hydroxyalkyl-difluoromethylbenzanilides of the formula (VIII)
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above and X 5 for C 2 -C 2 which is optionally monosubstituted or polysubstituted, identically or differently, by halogen and / or C 3 -C 6 -cycloalkyl stands for o-hydroxyalkyl, where the cycloalkyl part in turn can optionally be substituted by halogen and / or C 1 -C 4 alkyl, optionally dehydrated in the presence of a diluent and optionally in the presence of an acid, or g) halodifluoromethylbenzanilides of the formula (TV)
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above, and
  • X 2 represents chlorine, bromine, iodine or trifluoromethyl sulfonate, with an alkyne of the formula (IX) HC ⁇ — A 5 (IX), in which
  • a 5 is in each case optionally mono- or polysubstituted, identically or differently, by halogen and / or C 3 -C 6 -cycloalkyl-substituted C 2 -C 8 -alkyl, the cycloalkyl part in turn optionally being substituted by halogen and or C r C 4 -alkyl or an alkene of the formula (X)
  • a 6 , A 7 and A 8 each independently represent hydrogen or optionally mono- or polysubstituted, identically or differently, alkyl substituted by halogen and / or C 3 -C 6 -cycloalkyl, the cycloalkyl part in turn optionally being substituted by halogen and / or C ⁇ - C - alkyl can be substituted and the total number of
  • R 1 , R 2 , R 3 , R 4 and R 5 have the meanings given above and
  • a 9 represents hydrogen or optionally mono- or polysubstituted, identically or differently, C 1 -C 8 -alkyl substituted by halogen and / or C 3 -Cycloalk l, where the cycloalkyl part in turn may optionally be substituted by halogen and or CC-alkyl, with a phosphorus compound of the general formula (Xu)
  • R 6 , R 7 , R 8 , R 9 and R 10 have the meanings given above and X 6 represents chlorine, bromine or iodine, in the presence of a base and in the presence of a diluent.
  • the difluoromethylbenzanilides of the formula (I) according to the invention show a substantially better fungicidal activity than the constitutionally most similar, known active substances of the same direction of action.
  • the compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as, for. 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 and optical isomers, any mixtures of these isomers and the possible tautomeric forms are claimed.
  • the difluoromethylbenzanilides according to the invention are generally defined by the formula (I).
  • 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.
  • R 1 , R 2 , R 3 and R 4 independently of one another preferably represent hydrogen, fluorine, chlorine or methyl.
  • R 1 particularly preferably represents hydrogen or fluorine.
  • R 1 very particularly preferably represents hydrogen.
  • R 1 also very particularly preferably represents fluorine.
  • R 2 particularly preferably represents hydrogen.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine or methylthio.
  • R 3 very particularly preferably represents hydrogen.
  • R 3 also very particularly preferably represents fluorine.
  • R 4 particularly preferably represents hydrogen, methyl or isopropyl.
  • R 4 very particularly preferably represents hydrogen.
  • R 4 also very particularly preferably represents methyl.
  • R 1 , R 2 , R 3 and R 4 very particularly preferably simultaneously represent hydrogen.
  • R 5 preferably represents hydrogen; -C 6 -alkyl, CC 4 -alkylsulfinyl, dC 4 -alkylsulfonyl, d- C3-alkoxy-C 3 -C 3 -alkyl, C 3 -C 6 -cycloalkyl; C r C 4 haloalkyl, dC 4 haloalkylthio, haloalkylsulfinyl dC, CC 4 -haloalkylsulfonyl, halo-C ⁇ -C3-alkoxy-C C 3 alkyl, C 3 -C ö halocycloalkyl having in each case 1 to 9 Fluorine, chlorine and / or bromine atoms, formyl-CC 3 -alkyl, (dC 3 -
  • R 5 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,
  • R 5 very particularly preferably represents hydrogen; Methyl, methoxymethyl, -CH 2 -CHO, -CH 2 CH 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 or -COR 6 .
  • R 6 preferably represents hydrogen, CC 6 alkyl, CC 4 alkoxy, CC 3 alkoxy-dC 3 alkyl, C 3 -
  • R 6 particularly preferably represents hydrogen, methyl, ethyl, n- or iso-propyl, tert-butyl, methoxy, ethoxy, iso-propoxy, tert-butoxy, cyclopropyl; Trifluoromethyl, trifluoromethoxy,
  • -COR 11 R 6 very particularly preferably represents hydrogen, -COCH 3 , -CHO, -COCH 2 OCH 3 ,
  • R 7 and R 8 independently of one another preferably represent hydrogen, CC 6 -alkyl, dC 3 -alkoxy-C r C 3 -alkyl, C 3 -C 6 -cycloalkyl; C, -C 4 haloalkyl, halo -CC 3 alkoxy-C r C 3 alkyl, C 3 -C 6 -
  • Halogencycloalkyl 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 is optionally monosubstituted to tetrasubstituted, identically or differently, by halogen or CQ-alkyl, the heterocycle 1 or can contain 2 further, non-adjacent heteroatoms from the series oxygen, sulfur or NR 12 .
  • 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 one optionally up to four times, identical or different by fluorine,
  • R 9 and R 10 independently of one another are preferably hydrogen, -CC 6 -alkyl, C 3 -C 6 -cycloal- yl; CC 4 haloalkyl, C 3 -C 6 halocycloalkyl each having 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R 9 and R 10 together with the nitrogen atom to which they are attached, preferably form one optionally one or more times, identically or differently, by halogen or C r
  • R 9 and R 10 independently of one another particularly preferably represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl,
  • R 9 and R 10 together with the nitrogen atom to which they are attached, particularly preferably form a saturated heterocycle from the series morpholine which may be mono- to tetrasubstituted, identically or differently, by fluorine, chlorine, bromine or methyl, Thiomo holin or piperazine, where the piperazine on the second nitrogen atom can be substituted by R 12 .
  • R 11 preferably represents hydrogen, CC 6 -alkyl, C r C 4 -alkoxy, C, -C 3 -alkoxy-C r C 3 -alkyl, C 3 - C 6 -cycloalkyl; CC 4 haloalkyl, CC 4 -haloalkoxy, halo-C C 3 alkoxy-C r C 3 - alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine and / or bromine atoms.
  • R ⁇ particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, tert-butyl,
  • R 12 preferably represents hydrogen or CC 4 alkyl.
  • R 12 particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl.
  • Z preferably represents Z 1 .
  • Z 1 preferably represents phenyl which is monosubstituted to pentas, identical or differently substituted, the substituents being selected from the list W 1 .
  • Z 1 particularly preferably represents monosubstituted phenyl, where the substituents from
  • List W 1 are selected.
  • Z 1 also particularly preferably represents phenyl which is substituted twice, identically or differently, the substituents being selected from the list W 1 .
  • Z 1 also particularly preferably represents triple, identical or differently substituted phenyl, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is monosubstituted in the 4-position, the
  • Substituents are selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is substituted twice, identically or differently in the 3,4-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is substituted twice, identically or differently in the 2,4-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is substituted twice, identically or differently in the 3,5-position, the substituents being selected from the list W 1 .
  • Z 1 very particularly preferably represents phenyl which is substituted three times, identically or differently in the 2,4,6-position, the substituents being selected from the list W 1 .
  • W 1 stands for halogen, cyano, nitro, amino, hydroxy, formyl, carboxyl, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy,
  • Haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms; each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dial ylaminocarbonyloxy with 1 to 6 carbon atoms in the respective hydrocarbon chains, alkenylcarbonyl or alkynylcarbonyl, with 2 to 6 carbon atoms hydrocarbon chains;
  • Q 1 represents hydrogen, hydroxyl, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms or cycloalkyl having 1 to 6 carbon atoms and Q 2 is hydroxyl, amino, methylamino, phenyl, benzyl or for alkyl or alkoxy with 1 to 4 carbon atoms, each optionally substituted by halogen, cyano, hydroxy, alkoxy, alkylthio, alkylamino, dialkylamino or phenyl, or for alkenyloxy or alkynyloxy each with 2 to 4 carbon atoms, and in each case optionally in the ring part simply to phenyl, phenoxy, phenyllthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthi
  • Q 1 represents hydrogen, methyl, ethyl, trifluoromethyl or cyclopropyl
  • Q 2 represents hydroxy, methoxy, ethoxy, propoxy or isopropoxy.
  • Z also preferably represents Z 2 .
  • Z 2 preferably represents optionally up to four times, identical or different, by C 1 -C 4 -
  • Z 2 particularly preferably represents cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, bicyclo [2.2. l] heptyl or bicyclo [2.2.2] octyl.
  • Z also preferably represents Z 3 .
  • Z 3 preferably stands for unsubstituted C 2 -C 20 alkyl or for mono- or polysubstituted, identically or differently, by fluorine, chlorine, bromine, iodine and / or C 3 -C 6 cycloalkyl-substituted -CC 20 alkyl, where the cycloalkyl part, in turn, may optionally be substituted up to four times, identically or differently, by fluorine, chlorine, bromine, iodine, CC 4 alkyl and / or CC 4 haloalkyl.
  • Z 3 particularly preferably represents unsubstituted C 2 -C 20 -alkyl.
  • Z 3 also particularly preferably represents d-do-alkyl substituted by chlorine, cyclopropyl, dichlorocyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • Z also preferably represents Z 4 .
  • Z 4 preferably represents C 2 -C 20 alkenyl or C 2 -C 20 alkynyl which is optionally substituted once or several times, identically or differently, by fluorine, chlorine, bromine, iodine and / or C 3 -C 6 cycloalkyl, the cycloalkyl part in turn optionally up to four times, identical or different by fluorine, chlorine, bromine, iodine, CC 4 alkyl and / or C
  • C 4 haloalkyl may be substituted.
  • Z 4 particularly preferably represents C 2 -C 20 alkenyl or C 2 -C 0 alkynyl.
  • Z and R 4 are also preferably, together with the carbon atoms to which they are attached, an optionally mono- to tetrasubstituted, identical or differently substituted 5- or
  • Z and R 4 are also particularly preferably, together with the carbon atoms to which they are attached, an optionally mono-, di- or trisubstituted by methyl-substituted 5- or 6-membered carbocyclic ring.
  • Compounds of the formula (Ic) are also preferred
  • R 5 "1 preferably represents CC 6 -alkyl, dC 4 -alkylsulfinyl, dC 4 -alkylsulfonyl, C r C 3 -alkoxy-dC 3 -alkyl, C 3 -C 6 -cycloalkyl; C ⁇ -C 4 -haloalkyl, CC 4 -haloalkylthio, CC 4 - haloalkylsulfmyl, CC 4 -haloalkylsulfonyl, halo-dd-alkoxy-Crd-alkyl, C 3 - C 6 -halo-cycloalkyl, each with 1 to 9 fluorine, chlorine and / or bromine atoms, formyl-d- d-alkyl, (-C-C 3 alkyl) carbonyl-dC 3 -alkyl, (CC 3 -alkoxy) carbonyl-C r C 3 -
  • R 5 "1 particularly preferably represents methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl, pentyl or hexyl, methylsulfmyl, ethylsulfmyl, n- or iso-propylsulfmyl, n-, iso-, sec- or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or iso-propylsulfonyl, n-, iso-, sec- or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, Trichloromethyl, trifluoroethyl,
  • R 5 "1 very particularly preferably represents methyl, methoxymethyl, -CH 2 -CHO, -CH 2 CH 2 -CHO, -CH 2 -CO-CH 3 , -CH 2 -CO-CH 2 CH 3 , -CH 2 -CO-CH (CH 3 ) 2 or -COR 6 .
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also be used in
  • C r C 20 alkyl encompasses the largest range defined here for an alkyl radical. Specifically, this definition includes the meanings methyl, ethyl, n-, iso-propyl, n-, iso-, sec-, tert-butyl, and all isomeric pentyls, hexyls, heptyls, octyls, nonyls, decyls, undecyls and dodecyls , Tridecyle, Tetradecyle, Pentadecyle, Hexadecyle, Heptadecyle, Octadecyle, Nonadecyle and Eicosyle.
  • alkenyl encompasses the largest range defined here for an alkenyl radical. Specifically, this definition includes the meanings ethenyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, l -Methyl-2-propenyl, 2-methyl-2-propenyl, 1-ethylethenyl, and in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls, nonenyls, decenyls, undecenyls, dodecenyls, tridecenyls, tetradecenyls, pentadecenyls, hexadecenyls, heptadecenyls , Nonadecenyl,
  • Preferred meanings are ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 4-pentenyl , 1-methyl-1-butenyl, 1,2-dimethyl-1-propenyl, 1-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 1,3-dimethyl-1-butenyl, 1-methyl-1 -hexenyl, 1,3,3 -trimethyl-1-butenyl.
  • C 2 -C 20 alkynyl encompasses the largest range defined here for an alkynyl radical. Specifically, this definition includes the meanings ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, as well as all isomeric pentynyls, hexinyls, heptinyls, octynyls, noninyls , Decinyle, Undecinyle, Dodecinyle, Tridecinyle, Tetradecinyle, Pentadecinyle, Hexadecinyle, Heptadecinyle, Octadecinyle, Nonadecinyle and Eicosinyle.
  • Preferred meanings are ethynyl, 1-propynyl, 1-butynyl, 3-butynyl, l-methyl-2-propynyl, 1-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, 3,3-dimethyl-l -butinyl, 4,4-dimethyl-1-pentynyl, 4,4-dimethyl-2-pentynyl, 1,4-dimethyl-2-pentynyl.
  • Optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • Residues substituted by halogen such as haloalkyl, are halogenated once or more than once. 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.
  • Formula (II) provides a general definition of the difluoromethylbenzoyl derivatives required as starting materials for carrying out process (a) according to the invention.
  • X 1 preferably represents chlorine or hydroxy.
  • Formula (HI) provides a general definition of the aniline derivatives which are further required as starting materials for carrying out process (a) according to the invention.
  • R 1 , R 2 , R 3 , R 4 , R 5 and Z have preferred, particularly preferably or very particularly preferably, those meanings which have already been associated with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for these radicals.
  • Halogen-difluoromethylbenzanilides are generally defined by the formula (TV).
  • R 1 , R 2 , R 3 , R 4 and R 5 have preferred, particularly preferably or very particularly preferably those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention , particularly preferred or very particularly preferred for these radicals.
  • X 2 stands for
  • halodifluoromethylbenzanilides of the formula (TV) are not yet known. As new chemical compounds, they are also the subject of the present application. They are obtained by k) difluoromethylbenzoyl derivatives of the formula (H)
  • R, R, R, R, R and X 2 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 (XVI) provides a general definition of the halogen anilines which are further required as starting materials for carrying out process (k) according to the invention.
  • R 1 , R 2 , R 3 , R 4 , R 5 and X 2 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 (I ), or the precursors of the formula (HI) were given as preferred, particularly preferred or very particularly preferred for these radicals.
  • haloanilines of the formula (XVI) are known synthetic chemicals or can be obtained by known processes.
  • R 5 is not hydrogen
  • the radical R 5 can be introduced at the level of the compounds of the formula (XVI) by customary derivatization methods. It is also possible first to prepare compounds of the formula (TV) in which R 5 is hydrogen and then to derivatize the products obtained by customary methods (cf. process (i) according to the invention).
  • Formula (V) provides a general definition of the boronic acid derivatives which are further required as starting materials for carrying out process (b) according to the invention.
  • Z 1 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for Z 1 in connection with the description of the compounds of the formula (I) according to the invention were.
  • a 1 and A 2 each represent hydrogen or together represent tetramethylethylene.
  • the boronic acid derivatives of the formula (V) are known and / or can be prepared by known processes (cf., for example, WO 01/90084 and US 5,633,218).
  • Difluoromethylbenzamide boronic acid derivatives are generally defined by the formula (VI).
  • R 1, R 2, R 3, R 4 and R 5 have preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of ER- inventive compounds of formula (I) as preferred, particularly preferred or very particularly preferred for these radicals.
  • a 3 and A 4 each represent hydrogen or together represent tetramethylethylene.
  • the difluoromethylbenzamide-boronic acid derivatives of the formula (VI) are not yet known. They are new chemical compounds and are also the subject of the present application. They are obtained by 1) difluoromethylbenzoyl derivatives of the formula (H)
  • R 1 , R 2 , R 3 , R 4 , R 5 , A 3 and A 4 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
  • Formula (XV ⁇ ) generally defines the aniline boronic acid derivatives which are further required as starting materials for carrying out process (1) according to the invention.
  • R 1 , R 2 , R 3 , R 4 and R 5 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 (I) according to the invention as preferred, particularly preferred or very particularly preferred for these radicals.
  • a 3 and A 4 each represent hydrogen or together represent tetramethylethylene.
  • aniline boronic acid derivatives of the formula (XVII) are known synthetic chemicals or can be obtained by known processes.
  • the radical R 5 can be introduced at the level of the compounds of the formula (XVH) by customary derivatization methods. It is also possible first to prepare compounds of the formula (VI) in which R 5 is hydrogen and then to derivatize the products obtained by customary methods (cf. process (i) according to the invention).
  • Formula (VII) provides a general definition of the phenyl derivatives which are furthermore required as starting materials for carrying out process (c) according to the invention.
  • Z 1 has preferred, particularly preferred or very particularly preferred those meanings which have already been given as preferred, particularly preferred or very particularly preferred for Z 1 in connection with the description of the compounds of the formula (I) according to the invention were.
  • X 3 stands for chlorine, bromine, iodine or trifluoromethyl sulfonate.
  • VTT The phenyl derivatives of the formula (VTT) are known synthetic chemicals.
  • the 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bis-l, 3,2-dioxaborolane required to carry out process (d) according to the invention is commercially available chemical for synthesis.
  • Formula (Ia) provides a general definition of the difluoromethylbenzanilides required as starting materials for carrying out process (e) according to the invention.
  • R 1 , R 2 , R 3 , R 4 and R 5 have preferred, particularly preferably or very particularly preferably those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention , particularly preferred or very particularly preferred for these radicals.
  • the compounds of the formula (Ia) are compounds according to the invention and can be prepared by processes (a), (f), (g) or (h). Method (f)
  • Formula (VHI) provides a general definition of the hydroxyalkyl difluoromethylbenzanilides required as starting materials for carrying out process (f) according to the invention.
  • R 1, R 2, R 3, R 4 and R 5 have preferred, particularly preferred and very particularly preferably have those meanings already mentioned in connection with the description of ER- inventive compounds of formula (I) as preferred, particularly preferred or very particularly preferred for these radicals.
  • X 5 preferably represents C 2 -C 2 -hydroxyalkyl which is optionally monosubstituted to tetrasubstituted, identically or differently, by chlorine, fluorine, bromine and / or dQ-cycloalkyl, the cycloalkyl part in turn optionally being halogen and / or dC 4 -alkyl can be substituted.
  • X 5 particularly preferably represents optionally up to four times, identically or differently, substituted by fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and / or cyclohexyl, in each case straight-chain or branched, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl,
  • VHI hydroxyalkyl difluoromethylbenzanilides
  • hydroxyalkyl difluoromethylbenzanilides of the formula (VHI) are obtained by m) difluoromethylbenzoyl derivatives of the formula (H) in which X 1 represents halogen or hydroxy, with hydroxyalkylaniline derivatives of the formula (XVHI)
  • R 1 , R 2 , R 3 , R 4 , R 5 and X 5 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 (XVHI) provides a general definition of the hydroxyalkylaniline derivatives which are further required as starting materials for carrying out process (1) according to the invention.
  • R 1 , R 2 , R 3 , R 4 , R 5 and X 5 have preferred, particularly preferably or very particularly preferably those meanings which have already been connected with the description of the compounds of the formulas (I ) or (VHT) as preferred, particularly preferred or very particularly preferred for these radicals.
  • the hydroxyalkylaniline derivatives of the formula (XVHI) are known and / or can be obtained by known methods (cf., for example, US Pat. No. 3,917,592 or EP-A 0 824099).
  • R 5 is not hydrogen
  • the radical R 5 can be introduced at the level of the compounds of the formula (XVIII) by customary derivatization methods. It is also possible to first prepare compounds of the formula (VIH) in which R 5 represents hydrogen and then to derivatize the products obtained by customary methods [cf. the inventive method (i)].
  • Formula (IX) provides a general definition of the alkynes further required as starting materials for carrying out process (g) according to the invention.
  • cycloalkyl moiety for its part is optionally substituted by halogen and / or CC - substituted alkyl can be.
  • alkynes of the formula (VI) are known synthetic chemicals.
  • Formula (X) provides a general definition of the alkenes which are alternatively required as starting materials for carrying out process (g) according to the invention.
  • a 6 , A 7 and A 8 independently of one another preferably each represent hydrogen or, if appropriate, up to four times, identically or differently, by fluorine, chlorine, bromine and / or C 3 -C 6 -
  • Cycloalkyl substituted alkyl the cycloalkyl part in turn optionally being replaced by
  • Halogen and / or C] -C alkyl may be substituted and the total number of
  • Carbon atoms of the open-chain part of the molecule does not exceed the number 12.
  • a 6 , A 7 and A 8 independently of one another particularly preferably each represent hydrogen or, if appropriate, one to four times, identically or differently, by fluorine, cyclopropyl,
  • Difluorocyclopropyl, cyclobutyl, cyclopentyl and / or cyclohexyl substituted, in each case straight-chain or branched, ethyl, propyl, butyl, pentyl, hexyl, heptyl or acrylic, each linked at any desired position, the total number of carbon atoms in the open-chain part of the molecule not exceeding 12.
  • the alkenes of the formula (VH) are known synthetic chemicals.
  • Formula (XI) provides a general definition of the ketones required as starting materials for carrying out process (h) according to the invention.
  • R 1 , R 2 , R 3 , R 4 and R 5 have preferred, particularly preferably or very particularly preferably, those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention, were particularly preferred or very particularly preferred for these radicals.
  • a 9 preferably represents optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, bromine and or C 3 -C 6 cycloalkyl-substituted C 2 -C ⁇ 0 - alkyl, where the cycloalkyl moiety for its part is optionally substituted by halogen and / or C ⁇ -C 4 alkyl may be substituted.
  • a 9 particularly preferably represents optionally up to four times, identical or different from fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and / or cyclohexyl Substituted, straight-chain or branched, in each case linked ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl.
  • ketones of the formula (VHI) are not yet known. As new chemical compounds, they are also the subject of the present application. They are obtained by n) difluoromethylbenzoyl derivatives of the formula (H)
  • Formula (XIX) provides a general definition of the ketoanilines which are further required as starting materials for carrying out process (s) according to the invention.
  • R 1, R 2, R 3, R 4, R 5 and A are 9 preferred, particularly preferred and very particularly preferred meanings, the gene already in connection with the description of the invention of formulas Verbindun- (I) or (XI) were given as preferred, particularly preferred or very particularly preferred for these radicals.
  • ketoanilines of the formula (XIX) are known (cf. J. Am. Chem. Soc. 1978, 100, 4842-4857 or US 4,032,573) and / or can be obtained by known methods.
  • R 5 is not hydrogen
  • the radical R 5 can be introduced at the level of the compounds of the formula (XXII) by customary derivatization methods. It is also possible first to prepare compounds of the formula (VIII) in which R 5 is hydrogen and then to derivatize the products obtained by customary methods (cf. process (i) according to the invention).
  • Formula (XII) provides a general definition of the phosphorus compounds which are further required as starting materials for carrying out process (h) according to the invention.
  • a 10 preferably represents optionally mono- to tetrasubstituted by identical or different substituents from chlorine, fluorine, bromine and / or C 3 -C 6 cycloalkyl-substituted C 2 -C ⁇ 0 alkyl, where the cycloalkyl moiety for its part may be substituted by halogen and / or C Q-alkyl can be substituted.
  • a 10 particularly preferably represents optionally up to four times, identical or different, substituted by fluorine, cyclopropyl, difluorocyclopropyl, cyclobutyl, cyclopentyl and / or cyclohexyl, in each case straight-chain or branched, ethyl, propyl, butyl, pentyl, hexyl, linked at any point, Heptyl or octyl.
  • the phosphorus compounds of the formula (XU) are known and / or can be prepared by known processes (cf. Justus Liebigs Ann. Chem. 1953, 580, 44-57 or Pure Appl. Chem. 1964, 9, 307-335).
  • Formula (Ib) provides a general definition of the difluoromethylbenzanilides required as starting materials for carrying out process (i) according to the invention.
  • R 1 , R 2 , R 3 , R 4 and Z have preferred, particularly preferably or very particularly preferably, those meanings which have already been preferred in connection with the description of the compounds of the formula (I) according to the invention, were particularly preferred or very particularly preferred for these radicals.
  • the compounds of the formula (Ib) are compounds according to the invention and can be prepared by processes (a) to (h).
  • Formula (XTTT) provides a general definition of the halides required as starting materials for carrying out process (i) according to the invention.
  • R 5 ′′ 1 is preferably, particularly preferably or very particularly preferably for those meanings which are already preferred, particularly preferred or very particularly preferred in connection with the description of the compounds of the formula (Ig) these residues have been indicated
  • X 6 represents chlorine, bromine or iodine.
  • Suitable diluents for carrying out processes (a), (k), (1), (m) and (n) 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
  • Processes (a), (k), (1), (m) and (n) 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, lithium diisopropylamide, narrium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide , Potassium hydroxide, sodium 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
  • Processes (a), (k), (1), (m) and (n) according to the invention are optionally carried out in the presence of a suitable condensing agent.
  • a suitable condensing agent all condensation agents which can usually be used for such amidation reactions are suitable.
  • acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride
  • 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-eth
  • Processes (a), (k), (1), (m) and (n) according to the invention are optionally carried out in the presence of a catalyst.
  • a catalyst examples include 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.
  • reaction temperatures can be varied within a substantial range when carrying out processes (a), (k), (1), (m) and (n). In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.
  • Formula (TT) is generally used per mole of the difluoromethylbenzoyl derivative of the formula (TT)
  • ketoaniline of the formula 0.8 to 15 mol, preferably 0.8 to 8 mol, of ketoaniline of the formula are generally employed per mole of the difluoromethylbenzoyl derivative of the formula (TT) (XVI) a.
  • Suitable diluents for carrying out processes (b), (c) and (d) are all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, e.g. Petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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; Nitriles such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-
  • reaction temperatures can be varied within a substantial range when carrying out processes (b), (c) and (d) according to the invention. In general, temperatures from 0 ° C to 180 ° C, preferably at temperatures from 20 ° C to 150 ° C.
  • the processes (b), (c) and (d) 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, fluorides, phosphates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, lithium diisopropyl amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide , Sodium acetate, sodium phosphate, potassium phosphate, potassium fluoride, cesium fluoride, 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
  • a catalyst such as, for example, a palladium salt or complex.
  • a catalyst such as, for example, a palladium salt or complex.
  • Palladium chloride, palladium acetate, tetrakis (triphenylphosphine) palladium, bis (triphenylphosphine) palladium dichloride or (l, l'-bis (diphenylphosphino) ferrocene palladium ( ⁇ ) chloride) are preferably suitable for this purpose.
  • a palladium complex can also be generated in the reaction mixture if a palladium salt and a complex ligand, e.g. Triethylphosphane, tri-tert-butylphosphine, tricyclohexylphosphine, 2- (dicyclohexylphosphine) biphenyl, 2- (di-tert-butylphosphine) biphenyl, 2- (dicyclohexylphosphine) -2 '- (N, N-dimethylamino) -biphenyl, triphenylphosphine, tris (o-tolyl) phosphine, sodium 3- (diphenylphosphino) benzenesulfonate, tris-2- (methoxyphenyl) phosphine, 2,2'-bis (diphenylphosphine) -l, l ' -bmaphthyl, 1,4-bis (diphenylpho
  • 0.8 to 15 mol, preferably 0.8 to 8 mol, of phenyl derivative are generally employed per mole of the halodifluoromethylbenzanilide of the formula (IV) of the formula (VH) and 0.8 to 15 mol, preferably 0.8 to 8 mol of 4,4,4 ', 4 l , 5,5,5', 5'-octamethyl-2,2'-bis- l, 3,2-dioxaborolane.
  • Suitable diluents for carrying out process (e) according to the invention are all inert organic solvents.
  • aliphatic or alicyclic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane or decalin; Ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tefrahydrofuran, 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.
  • aliphatic or alicyclic hydrocarbons such
  • the process (s) according to the invention is carried out in the presence of a catalyst.
  • All catalysts which are usually used for hydrogenations are suitable as such. Examples include: Raney nickel, palladium or platinum, optionally on a carrier material, such as activated carbon.
  • the hydrogenation in process (e) according to the invention can also be carried out in the presence of triethylsilane instead of in the presence of hydrogen in combination with a catalyst.
  • reaction temperatures can be varied within a substantial range when carrying out process (e) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 20 ° C to 100 ° C.
  • Process (e) according to the invention is 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 process (f) 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; Ketones such as ace
  • Process (f) according to the invention is optionally carried out in the presence of an acid.
  • All inorganic and organic protonic and Lewis acids, as well as all polymeric acids, are suitable as such. These include, for example, hydrogen chloride, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, toluenesulfonic acid, boron trifluoride (also as etherate), boron tribromide, aluminum trichloride, titanium tetrachloride, tetrabutyl orthide chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride, zinc chloride,
  • reaction temperatures can be varied within a substantial range when carrying out process (f) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 100 ° C.
  • Processes (f) and (e) according to the invention can also be carried out in a tandem reaction (“one-pot reaction”).
  • a compound of the formula (VHI) is optionally in the presence of a diluent (suitable solvents as for process (f)), optionally in the presence of an acid (suitable acids as for process (f)) and in the presence of triethylsilane.
  • Suitable diluents for carrying out process (g) according to the invention are all inert organic solvents. These preferably include nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile or amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide.
  • nitriles such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile
  • amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide.
  • Process (g) according to the invention is 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-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, triethylamine, tributylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine, N-methylpiperidine, N-
  • Process (g) according to the invention is 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 preferred 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, -binaphthyl, dicyclohexylphosphine biphenyl, 1,4-bis (diphenylphosphino) butane, bisdiphenylphosphinoferrocene, di (tert-butylphosphino) biphenyl, di (cyclohexylphosphino) biphenyl, 2-dicyclohexylphosphino-2'-N, N-dimethylaminobiphenyl, tricyclohexylphosphine, ttri-tert-butylphosphine.
  • ligands can also be dispensed with.
  • Process (g) according to the invention is 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 when carrying out process (g) according to the invention. In general, temperatures from 20 ° C to 180 ° C, preferably at temperatures from 50 ° C to 150 ° C.
  • Suitable diluents for carrying out process (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 tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Nitriles, like Acet
  • Process (h) according to the invention is optionally carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates or alkali metal hydrocarbon compounds, such as, for example, sodium hydride, sodium hydroxide, potassium hydroxide, sodium amide, lithium diisopropylamide, sodium methylate, sodium ethylate, potassium tert-butoxide, methylitium , Phenyllitium or butyllitium.
  • reaction temperatures can be varied within a substantial range when carrying out process (h) according to the invention. In general, temperatures from -80 ° C to 150 ° C, preferably at temperatures from -30 ° C to 80 ° C.
  • Suitable diluents for carrying out process (i) 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
  • Process (i) according to the invention is carried out in the presence of a base.
  • a base preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or
  • bicarbonates such as 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-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecen (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU
  • reaction temperatures can be varied within a substantial range when carrying out process (i) 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 (XTTT) are generally employed per mole of the iodopyrazolylcarboxanilide of the formula (Ib) ) on.
  • All 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.
  • 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, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella herpotrichoides.
  • the active compounds 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 in the present context as substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesired 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 attack by the pests mentioned within a certain period of time after the treatment.
  • the period of time within which protection is brought about generally extends from 1 to 10 days, preferably 1 to 7 days, after the plants have been treated with the active compounds.
  • the active compounds according to the invention can be used with particularly good success for combating cereal diseases, for example against Puccinia species and for diseases in wine, fruit and vegetable cultivation, for example for botrytis, Venturia or Alternaria 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 also be used in certain concentrations and application rates as herbicides, for influencing plant growth and for controlling animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of further active compounds.
  • 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 as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary methods
  • 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 are attacked or decomposed by microorganisms can be.
  • 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 slime 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 like 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 and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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.
  • emulsifiers and / or foam-generating 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 dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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 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.
  • iprodione iprovalicarb
  • Irumamycin isoprothiolane
  • Isovaledione kasugamycin
  • Kresoxim-methyl iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl;
  • mancozeb maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole;
  • methasulfocarb Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; Myclobutanil; myclozoline; natamycin; nicobifen; Nitro Thal-isopropyl; Noviflumuron; nuarimol; ofurace;
  • orysastrobin oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol;
  • Pefurazoate Pefurazoate; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins;
  • Butathiofos Butocarboxim, Butoxycarboxim, Butylpyridaben, Cadusafos, Camphechlor, Carbaryl,
  • Pirimiphos-methyl Pirimiphos-ethyl
  • Prallethrin Profenofos
  • Propetamphos Propoxur, Prothiofos, Prothoate, Protrifenbute, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridalyl, Pyridaphenthion, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Resmethrin, RH -725, RU-575, RU-575, RU-575, RU-575, RU-575, RU-R525, RU-575, RU-575, RU-R525, RU-255, RU-575, RU-R525, RU-255 S-421, S-1833, Salithion,
  • the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal effects, in particular against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillichophophophytony fumigton, fumigatus and Fumigyus mentagrophytes, microsporon species such as microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillichophophytony fumigton, fumigatus and Fumigyus mentagrophytes
  • microsporon species such as microsporon canis and audouinii.
  • 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 result in superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and or widening the spectrum of action and / or strengthening 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 dryness or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which is actually about the expected effects go beyond.
  • 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 ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Machinability of the harvested products 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 vire n and 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 increased defense of the plants against insects, arachnids, namatodes and snails by toxins which arise 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), CryllA, CrylHA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants”).
  • Bacillus thuringiensis eg by the genes Cry ⁇ A (a) , CryIA (b), Cry ⁇ A (c), CryllA, CrylHA, CryIHB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations
  • Trans are also used the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors as well as resistance genes and correspondingly expressed proteins and toxins are particularly emphasized.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), 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 sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • 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.
  • Step 2 A solution of 29.0 g (189 mmol) of 2-difluoromethyl-benzonitrile in 700 mL 4% sodium hydroxide solution was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature, poured onto ice and acidified with concentrated hydrochloric acid. The precipitate was filtered off and dried. 19.3 g (58% of theory) of 2-difluoromethylbenzoic acid were obtained in
  • the specified logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18).
  • Eluents for determination in the acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the lambda max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. applications
  • Botrytis test (bean) / protective
  • 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.
  • compounds 3 and 4 of the preparation examples show an efficiency of 95% or better at an application rate of 500 g / ha.
  • Emulsifier 0.6 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 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.
  • compound no. 5 of the preparation examples show an efficiency of 100% at an application rate of 500 g / ha.
  • 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.

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CA2526358A1 (en) 2004-12-02
KR20060017605A (ko) 2006-02-24
AU2004240721A1 (en) 2004-12-02
JP2007502312A (ja) 2007-02-08
MXPA05012438A (es) 2006-05-25
WO2004103953A1 (de) 2004-12-02

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