WO2003059065A1 - Ceto-enols cycliques substitues par un biphenyle - Google Patents

Ceto-enols cycliques substitues par un biphenyle Download PDF

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Publication number
WO2003059065A1
WO2003059065A1 PCT/EP2003/000026 EP0300026W WO03059065A1 WO 2003059065 A1 WO2003059065 A1 WO 2003059065A1 EP 0300026 W EP0300026 W EP 0300026W WO 03059065 A1 WO03059065 A1 WO 03059065A1
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Prior art keywords
alkyl
alkoxy
optionally
substituted
methyl
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PCT/EP2003/000026
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German (de)
English (en)
Inventor
Reiner Fischer
Astrid Ullmann
Thomas Bretschneider
Astrid Mauler-Machnik
Karl-Heinz Kuck
Ulrike Wachendorff-Neumann
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Bayer Cropscience Aktiengesellschaft
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Priority to AU2003206693A priority Critical patent/AU2003206693A1/en
Publication of WO2003059065A1 publication Critical patent/WO2003059065A1/fr

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    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • 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
    • A01N43/02—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
    • A01N43/02—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
    • A01N43/12—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 condensed with a carbocyclic ring
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Definitions

  • the present invention relates to known biphenyl-substituted cyclic ketoenols and their use as fungicides.
  • biphenyl-substituted ketoenols have herbicidal, acaricidal and insecticidal properties: WO 99/48 869. Surprisingly, fungicidal properties have now also been found for the compounds described in WO 99/48869.
  • X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano
  • Z represents optionally substituted aryl
  • W and Y independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, nitro or cyano, CKE for one of the groups
  • halogen alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl, in which at least one ring atom is optionally replaced by a heteroatom, or in each case optionally by halogen, alkyl, haloalkyl, alkoxy, Halogenoalkoxy, cyano or nitro substituted aryl, arylalkyl or hetaryl,
  • B represents hydrogen or alkyl, or A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, optionally containing at least one heteroatom unsubstituted or substituted cycle,
  • D represents hydrogen or an optionally substituted radical from the series
  • a and D together with the atoms to which they are attached represent a saturated or unsaturated and optionally at least one heteroatom-containing cycle which is unsubstituted or substituted in the A, D part, or
  • a and Q 1 together represent in each case alkanediyl or alkenediyl optionally substituted by optionally substituted alkyl, hydroxy, alkoxy, alkylthio, cycloalkyl, benzyloxy or aryl, or
  • Q 1 represents hydrogen or alkyl
  • OQ 4 > Q 5 and d 6 independently of one another represent hydrogen or alkyl
  • Q 3 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl (in which a methylene group is optionally replaced by oxygen or sulfur) or optionally substituted phenyl, or
  • Q 3 and Q 4 together with the carbon atom to which they are attached represent a saturated or unsaturated, optionally a heteroatom-containing unsubstituted or substituted cycle, for hydrogen (a) or for one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • Rl for alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl optionally substituted by halogen, alkyl or alkoxy, which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
  • R2 represents in each case optionally substituted by halogen, alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl, ⁇ , R ⁇ and R ⁇ independently of one another each optionally by
  • R6 and R ⁇ independently of one another for hydrogen, in each case optionally substituted by halogen alkyl, cycloalkyl, alkenyl, alkoxy,
  • Alkoxyalkyl for optionally substituted phenyl, for optionally substituted benzyl, or together with the N atom to which they are attached, for an optionally substituted cycle interrupted by oxygen or sulfur.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the use of the pure isomers and that of the isomer mixtures as fungicides and compositions comprising them are the subject of the present invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • A, B, D, G, Q 1 , Q 2 , Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y and Z have the meaning given above.
  • A, B, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • A, B, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R R5, R6 and R 7 have the meaning given above.
  • the compounds of the formula (1-4) can exist in the two isomeric forms of the formulas (I-4-A) and (I-4-B),
  • the compounds of the formulas (1-4-A) and (I-4-B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-4-A) and (I-4-B) can optionally be separated by physical methods, for example by chromatographic methods. For reasons of better clarity, only one of the possible isomers is listed below. This does not exclude that the compounds may optionally be in the form of the isomer mixtures or in the other isomeric form.
  • A, B, Q ⁇ Q 2 , E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R5, R6 and R 7 have the meanings given above.
  • the compounds of the formula (1-5) can be present in the two isomeric forms of the formulas (I-5-A) or (I-5-B), which is indicated by the dashed line in the Formula (1-5) to be expressed:
  • the compounds of the formulas (1-5 -A) or (1-5 -B) can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulas (I-5-A) and (I-5-B) can optionally be separated by physical methods, for example by chromatographic methods.
  • A, B, E, L, M, Q 3 , Q 4 , Q 5 , Q 6 , W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R5, R6 and R 7 die have the meanings given above.
  • X preferably represents halogen, C ⁇ -C ⁇ - alkyl, Ci-COE-haloalkyl, C j -Cg- alkoxy, Ci-Cg-halogenoalkoxy, nitro or cyano,
  • V 1 is preferably hydrogen, halogen, C r C 1 - alkyl, C r C 6 - alkoxy, C r C 6 alkylthio, C r C 6 -Alkylsulf ⁇ nyl, C r C 6 alkylsulfonyl, C r C 4 -halogen - alkyl, C ⁇ -C4-haloalkoxy, nitro, cyano or in each case optionally mono- or polysubstituted by halogen, C Cg-alkyl, C Cg-alkoxy, C1-C4 haloalkyl, C j -C haloalkoxy, nitro or cyano, phenyl, Phenoxy, phenoxy-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkoxy, phenylthio-C 1 -C 4 -alkyl or phenyl-C 1 -
  • V 2 and V 3 are preferably each independently hydrogen, halogen, CJ-Cg alkyl, C j -Cg- alkoxy, C j -C 4 haloalkyl or haloalkoxy O j,
  • W and Y are preferably independently of one another hydrogen, halogen, Cj-Cg-alkyl, C j- Cg-haloalkyl, C Cg-alkoxy, C j - -haloalkoxy, nitro or cyano,
  • CKE preferably stands for one of the groups
  • B preferably represents hydrogen or C ⁇ -C - alkyl
  • A, B and the carbon atom to which they are attached preferably represent saturated C3-C j o-cycloalkyl or unsaturated C 5 -C ⁇ 0 cycloalkyl, in which optionally one ring member is replaced by oxygen or sulfur and which is optionally monosubstituted or disubstituted by C ⁇ -Cg-alkyl, C3-C10-cycloalkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-alkylthio, halogen or phenyl are substituted or
  • A, B and the carbon atom to which they are attached are preferably C3-C ⁇ -cycloalkyl, which is obtained by means of an alkylene diyl or optionally containing one or two oxygen and / or sulfur atoms which are not directly adjacent, or by an alkylenedioxyl or by an Alkylenedithioyl group is substituted, which forms a further five- to eight-membered ring with the carbon atom to which it is attached or
  • A, B and the carbon atom to which they are attached are preferably C3-
  • Cg-cycloalkyl or C5-Cg-cycloalkenyl in which two substituents together with the carbon atoms to which they are attached, for C2-C6-alkanediyl, C2 which are optionally substituted by C -C6-alkyl, Ci-Cg-alkoxy or halogen -C6-alkenediyl or C4-Cg-alkanedienediyl, in which a methylene group is optionally replaced by oxygen or sulfur, D preferably represents hydrogen, in each case optionally substituted by halogen -CC 2 -alkyl, C3-Cg-alkenyl, C3-Cg-alkynyl, C ⁇ -C ⁇ ) -alkoxy-C2-Cg-alkyl, poly-C ⁇ -Cg-alkoxy- C 2 -CG-alkyl, C ⁇ -C ⁇ 0 -alkylthio-C 2 -CG-alkyl, optionally substituted by
  • Haloalkyl substituted C3-Cg-cycloalkyl in which a ring member is optionally replaced by oxygen or sulfur or in each case optionally by halogen, Cj-Cß-alkyl, Cj-Cg-haloalkyl, Cj-Cg-alkoxy, Ci-Cg-haloalkoxy, cyano or nitro substituted phenyl, hetaryl with 5 or 6 ring atoms (for example furanyl, imidazolyl, pyridyl, thiazolyl,
  • a and D together preferably represent in each case optionally substituted C3-Cg-alkanediyl or C3-Cg-alkenediyl, in which a methylene group is optionally replaced by oxygen or sulfur and where the following are possible substituents: in each case Cj-Cg- which is optionally substituted by halogen Alkyl, C ⁇ -Cg alkoxy or another
  • a and Q 1 together preferably represent in each case optionally one to three times, identical or different by halogen, by in each case optionally mono- to trisubstituted by identical or different halogen-substituted C ⁇ -Cio-alkyl or Cj-Cg-alkoxy-substituted C3-C6 alkanediyl or C4-COE-alkenediyl, also optionally substituted j by a C ⁇ alkanediyl group or by an oxygen atom is bridged or
  • Q! preferably represents hydrogen or C 1 -C 4 alkyl
  • Q 2 > O ⁇ Q 5 and Q 6 independently of one another preferably represent hydrogen or C r C 4 alkyl
  • Q 3 preferably represents hydrogen, C r C 6 -alkyl, C r C 6 -alkoxy-C r C2-alkyl, C 1 -C 6 -alkylthio-C 1 -C 2 -alkyl, phenyl, optionally by C r C 4 - alkyl or C1-C4-alkoxy substituted C -Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur or optionally by halogen, CJ-C4-alkyl, C1-C4-alkoxy, C j ⁇ -haloalkyl, C C2-haloalkoxy, cyano or nitro substituted phenyl or
  • Q 3 and Q 4 together with the carbon atom to which they are attached, preferably represent a C3-C7 ring, optionally substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C2-haloalkyl, in which one Ring member is replaced by oxygen or sulfur,
  • G preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • phenyl optionally substituted by halogen, cyano, nitro, Cj-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-haloalkyl, Cj-Cg-haloalkoxy, Cj-Cg-alkylthio or C ⁇ - Cg-alkylsulfonyl,
  • phenyl optionally substituted by halogen, nitro, cyano, Cj-Cg-alkyl, Ci-Cg-alkoxy, Cj-Cg-haloalkyl or Cj-Cg-haloalkoxy
  • hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl),
  • phenoxy-Ci-Cg-alkyl optionally substituted by halogen or Cj-Cg-alkyl or for 5- or 6-membered hetaryloxy-Cj-Cg-alkyl optionally substituted by halogen, amino or Cj-Cg-alkyl (for example pyridyloxy-C ⁇ -C 6 -alkyl, pyrimidyloxy-C ⁇ -C 6 -alkyl or thiazolyloxy-C ⁇ - C 6 alkyl),
  • R 2 preferably represents in each case optionally substituted by halogen C ⁇ -
  • C20-alkyl C2-C20-alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl, poly-Ci-Cg-alk-oxy-C2-Cg-alkyl,
  • C3-Cg-cycloalkyl which is optionally substituted by halogen, Ci-Cg-alkyl or Cj-Cg-alkoxy or
  • R 3 preferably represents optionally substituted by halogen Cj-Cg-alkyl or in each case optionally substituted by halogen, C ⁇ -Cg-alkyl, Ci-Cg-alkoxy, C ⁇ -C4-haloalkyl, C ⁇ -C4-haloalkoxy, cyano or nitro Phenyl or benzyl,
  • R4 and R5 preferably independently of one another each represent optionally substituted by halogen C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, Cj-Cg-alkylthio, C2-Cg-alkenylthio, C3-C -cycloalkylthio or for each optionally by halogen, nitro, cyano, C1-C4- alkoxy, C ⁇ -C4-haloalkoxy, C ⁇ -C4-alkylthio, C1-C4-
  • R "and R 7 are, independently of one another, preferably hydrogen, for each Ci-Cg-alkyl optionally substituted by halogen, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl, -C-Cg-alkoxy- C ⁇ -Cg-alkyl, for counter phenyl optionally substituted by halogen, Ci-Cg-haloalkyl, C ⁇ -Cg-alkyl or Cj-Cg-alkoxy, benzyl optionally substituted by halogen, Cj-Cg-alkyl, Cj-Cg -haloalkyl or Cj-Cg-alkoxy or together to which they are bound to the nitrogen atom is substituted for a optionally substituted by C j ⁇ alkyl C3-Cg-alkylene radical in which optionally one carbon atom is replaced by oxygen or sulfur.
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • X particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C1-C4-alkoxy, C 1 -C 4 -haloalkyl, Oj ⁇ -haloalkoxy, nitro or cyano,
  • Z particularly preferably represents a radical
  • V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C Cg-alkyl, Nitro, cyano or in each case optionally once or twice by fluorine, chlorine, bromine, -C 4 -alkyl, C j -C -alkoxy, C ] -C 2 -haloalkyl, Ci ⁇ -haloalkoxy,
  • V 2 and V 3 are particularly preferably independently of one another hydrogen
  • CKE particularly preferably stands for one of the groups
  • B particularly preferably represents hydrogen or C j -C - alkyl or A, B and the carbon atom to which they are attached are particularly preferably saturated C -C -cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which is optionally mono- or disubstituted by Cj-Cg-alkyl, trifluoromethyl or Cj- Cg-alkoxy is substituted or
  • A, B and the carbon atom to which they are bonded are particularly preferably C5-Cg-cycloalkyl or C5-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are bonded are each optionally Methyl, methoxy, fluorine, chlorine or bromine substituted C2-C4-alkanediyl, C2-C4-alkenediyl, in which a methylene group is optionally replaced by oxygen or sulfur or butadiene diyl
  • D particularly preferably represents hydrogen, in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Cj-Cg-alkyl, C3 ⁇ Cg-alkenyl, Ci -C4-alkoxy-C2-C3-alkyl or -C-C4-alkylthio-C2- C3-alkyl, for optionally mono- to disubstituted by fluorine, chlorine, C1-C4-alkyl, C j - C4-alkoxy or -C-C2-haloalkyl, C3-C7-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur .
  • a and D together particularly preferably represent optionally substituted C3-C5-alkanediyl in which a methylene group is substituted by oxygen or
  • Sulfur can be replaced, methyl or methoxy being suitable as substituents or A and D (in the case of the compounds of the formula (II)) together with the atoms to which they are bonded represent one of the groups AD-1 to AD-10:
  • a and Q 1 together are particularly preferably each C 1 -C 4 -alkyl or C C2-alkoxy which is optionally mono- to trisubstituted by fluorine or C3-C4-alkanediyl or C3-C 4 -alkenediyl or
  • Q 1 particularly preferably represents hydrogen
  • Q 2 particularly preferably represents hydrogen
  • Q 4 , Q 5 and Q 6 are particularly preferably independently of one another hydrogen, methyl or ethyl
  • Q 3 particularly preferably represents hydrogen, C1-C 4 - alkyl, C ⁇ -C4-alkoxy-C ⁇ -
  • Q 3 and Q 4 particularly preferably together with the carbon atom to which they are attached, represent a saturated C5-C6- ing which is optionally simply substituted by methyl, methoxy or trifluoromethyl and in which a ring member is optionally replaced by oxygen or sulfur,
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M represents oxygen or sulfur
  • Rl particularly preferably represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine or optionally C3 to C7 cycloalkyl which is monosubstituted or disubstituted by fluorine, chlorine, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy and in which one or two ring members which are not directly adjacent are replaced by oxygen and / or sulfur,
  • phenyl-C4-C4-alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C1-C4-alkyl, Cj-C4-alkoxy, C-C3-haloalkyl or C1-C3-haloalkoxy,
  • R 2 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine-substituted C 1 -C 12 -alkyl, C2-C 2 -alkenyl, C 1 -C 4 -alkoxy-C2-C3-alkyl or poly-C 1 -C 4 -alkoxy-C2 -C3 alkyl,
  • C3-C7-cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C1-C4-alkyl or C1-C4-alkoxy or
  • R 3 particularly preferably represents Ci to Cg alkyl which is optionally three to five times substituted by fluorine or in each case optionally single to phenyl substituted twice by fluorine, chlorine, bromine, C1-C4-alkyl, C ⁇ -C alkoxy, C1-C3-haloalkyl, C ⁇ -C3-haloalkoxy, cyano or nitro,
  • R and R5 are particularly preferably independently of one another Ci-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (-C -Cg-alkyl) amino, Ci -Cg-alkylthio, C3-C4- Alkenylthio, C3-Cg-Cycloalkylthio or for each optionally single to double by fluorine, chlorine, bromine, nitro, cyano, C ⁇ - C3- alkoxy, C ⁇ -C3-haloalkoxy, C ⁇ -C3-alkylthio, C ⁇ -C3-haloalkyl- thio, -C-C3-alkyl or C1-C3 -haloalkyl-substituted phenyl, phenoxy or phenylthio,
  • R ° and R 7 independently of one another particularly preferably represent hydrogen, Ci-Cg-alkyl, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl, Cj-Cg-alkoxy-Cj-Cg-alkyl, for phenyl optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C j -C 3 haloalkyl, C 1 -C 4 -alkyl or C1-C4 alkoxy, for monosubstituted or disubstituted by fluorine, chlorine, bromine, C1-C 4 - Alkyl, C1-C3-haloalkyl or C1-C4-alkoxy-substituted benzyl, or together with the nitrogen atom to which they are attached for a C4-C5-alkyl radical which is optionally substituted by methyl or ethyl, in which,
  • halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • X very particularly preferably represents chlorine, methyl, ethyl, n-propyl, iso-
  • Z very particularly preferably represents a radical
  • V 1 very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso- Propoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano,
  • V 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,
  • W and Y very particularly preferably independently of one another represent hydrogen
  • CKE very particularly preferably stands for one of the groups
  • B very particularly preferably represents hydrogen, methyl or ethyl or A
  • B and the carbon atom to which they are attached very particularly preferably represent saturated C 3 -C 7 -cycloalkyl, in which a ring member is optionally replaced by oxygen or sulfur and which, if appropriate, is substituted once or twice by methyl, ethyl, n Propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy or tert .-Butoxy is substituted or
  • A, B and the carbon atom to which they are attached very particularly preferably represent C5-C6-cycloalkyl or Cs-Cg-cycloalkenyl, in which two substituents together with the carbon atoms to which they are attached represent C2-C4-alkanediyl or C 2 -C 4 -alkenediyl, where in each case one methylene group is optionally replaced by oxygen or sulfur or are butadiene diyl,
  • D very particularly preferably represents hydrogen, Cj-Cg-alkyl, C3-C4-alkenyl, C ⁇ -C3-alkoxy-C2-alkyl, C ⁇ -C3-alkylthio-C2-alkyl or C3-Cg-cycloalkyl, in which optionally a methylene group is replaced by oxygen or sulfur, or
  • a and D together very particularly preferably represent C3-C4-alkanediyl, in which a carbon atom is optionally replaced by sulfur or
  • a and D in the case of the compounds of the formula (II) together with the atoms to which they are attached very particularly preferably stand for one of the following groups AD:
  • a and Q 1 together very particularly preferably represent C3-C4-alkanediyl or butenediyl or optionally substituted by methyl or methoxy
  • Q 1 very particularly preferably represents hydrogen
  • Q 2 very particularly preferably represents hydrogen
  • Q 4 , Q 5 and Q 6 very particularly preferably independently of one another represent hydrogen, methyl or ethyl
  • Q 3 very particularly preferably represents hydrogen, methyl, ethyl, propyl, n-butyl, phenyl or C3-Cg-cycloalkyl, in which a methylene group is optionally replaced by oxygen or sulfur or
  • Q 3 and Q 4 very particularly preferably, together with the carbon to which they are attached, represent a saturated C 5 -C 6 ring which is optionally monosubstituted by methyl or methoxy and in which a ring member is optionally replaced by oxygen or sulfur,
  • G very particularly preferably represents hydrogen (a) or one of the groups ° L 4 "'0 *' * '(C, / S0 ⁇ R3 (d) . ⁇ / ⁇ E),
  • E represents a metal ion equivalent or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • Rl very particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C - C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 alkyl or optionally for C3-Cg-cycloalkyl which is simply substituted by fluorine, chlorine, methyl, ethyl, n-propyl, i-propyl or methoxy and in which one or two ring members which are not directly adjacent are optionally replaced by oxygen and / or sulfur,
  • R 2 very particularly preferably represents C 1 -C 6 -alkyl, C2-Cg-alkenyl, C 1 -C 4 -alkoxy-C2-alkyl or poly-C 1 -C 4 -alkoxy-C2-alkyl,
  • C3-Cg-cycloalkyl or for phenyl or benzyl which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl which is optionally trisubstituted by fluorine or in each case phenyl which is substituted by fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro .
  • R and R ⁇ very particularly preferably independently of one another for C1-C4-alkyl, Cj-C4-alkoxy, C ⁇ ⁇ C4-alkylamino, di- (C ⁇ -C4-alkyl) amino, C1-C4-alkyl- or for each optionally phenyl, phenoxy or phenylthio substituted once or twice by fluorine, chlorine, bromine, nitro, cyano, methoxy, methyl, trifluoromethyl, trifluoromethoxy,
  • R6 and R 7 independently of one another very particularly preferably represent hydrogen, for C 1 -C 4 -alkyl, C3-Cg-cycloalkyl, C 1 -C 4 -alkoxy, C3-C 4 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl , for phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, methyl or methoxy, or together with the nitrogen atom to which they are attached for a C5-Cg-alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur ,
  • X particularly preferably represents chlorine, methyl or methoxy
  • Z very particularly preferably represents a radical V 1 particularly preferably represents hydrogen, fluorine, chlorine, methyl, tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy or nitro,
  • V 2 particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl
  • W and Y are particularly preferably, independently of one another, hydrogen or methyl
  • CKE very particularly preferably stands for one of the groups
  • B particularly preferably represents hydrogen or methyl
  • A, B and the carbon atom to which they are attached are particularly preferably saturated C3-C7-cycloalkyl, in which a ring member is optionally replaced by oxygen and which is optionally mono- or disubstituted by methyl, ethyl, n-propyl, isopropyl, tert .
  • -Butyl, methoxy, ethoxy, n-propoxy, n-butoxy or iso-butoxy is substituted or
  • A, B and the carbon atom to which they are attached are particularly preferably C5-C6-cycloalkyl, where two substituents together with the carbon atoms to which they are attached are C 3 -C 4 -alkenediyl,
  • D particularly preferably represents hydrogen
  • Q 1 particularly preferably represents hydrogen
  • Q 2 particularly preferably represents hydrogen
  • Q 4 , Q 5 and Q 6 are particularly preferably independently of one another hydrogen, methyl or ethyl
  • Q 3 particularly preferably represents hydrogen, methyl, ethyl, propyl, n-butyl,
  • Q 3 and Q 4 particularly preferably together with the carbon to which they are attached represent a saturated Cs-Cg ring which is optionally monosubstituted by methyl or methoxy,
  • G particularly preferably represents hydrogen (a) or one of the groups in which
  • M represents oxygen or sulfur
  • Rl particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl or, if appropriate, simply by fluorine, chlorine , Methyl or methoxy substituted C3-Cg-cycloalkyl,
  • phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 2 particularly preferably represents Ci-Cg-alkyl, C2-Cg-alkenyl or C1-C4-alkoxy-C2-alkyl,
  • W stands for hydrogen or methyl
  • X stands for methyl, methoxy or chlorine
  • Y stands for hydrogen or methyl
  • A stands for methyl, i-propyl, s-butyl or cyclopropyl;
  • A stands for hydrogen or methyl, if Het stands for group (5),
  • A, B and the carbon atom to which they are attached are highlighted for saturated C3-C7-cycloalkyl, in which a ring member is optionally through
  • Oxygen is replaced and which one or two if necessary by
  • Q 3 stands for hydrogen, methyl, ethyl, n-butyl or phenyl
  • Q 4 stands for hydrogen or methyl
  • Q 3 and Q 4 are highlighted together with the carbon atom to which they are attached for a saturated Cs-Cg ring, Q 5 stands for hydrogen,
  • G stands for hydrogen (a) or for one of the groups
  • R 1 stands for C 1 -C 4 -alkyl or C 1 -C 2 alkoxy-C 1 -C 2 -alkyl
  • R 2 stands for C 1 -C 4 -alkyl or phenyl.
  • Saturated or unsaturated hydrocarbon radicals 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.
  • Cyclohexyl 1.18 (s, 3H, CH 3 cyclohexyl); 2.02 (s, 3H, Ar-CH3); 2.21 (s, 3H, Ar-CH3); 2.41 (d, IH, CH 2 CO); 2.47 (d, IH, CH 2 CO); 2.67 (s, 2H, CH 2 CO); 4.08 (q, 2H, CH 2 CH 3 ); 6.72 (s, IH, Ar-H); 7.17 (s, IH, Ar-H); 7.29 (d, 2H, Ar-H); 7.50 (d, 2H, Ar-H) ppm.
  • Eluents for determination in the acidic range 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration was 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 on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • 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 control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and
  • Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Some pathogens of fungal and bacterial are exemplary but not limiting
  • 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;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Sportsiginea;
  • 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 very good 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 those substances which are able to stimulate the defense system of plants in such a way that the treated plants largely undergo subsequent inocolation with undesirable microorganisms
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to remove plants within a certain period of time
  • 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 to combat diseases in wine, fruit and vegetable cultivation, such as, for example, against Venturia or Podosphaera species.
  • the active compounds according to the invention are also suitable for increasing the crop yield.
  • the active compounds according to the invention can also be used 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 and parts of plants can be treated with the active compounds according to the invention.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated 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 ones
  • Plants and including plant varieties that 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 sprout, leaf, flower and root, 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 takes place directly or by acting on their environment, habitat or Storage space according to the usual treatment methods, for example by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by means of single-layer or multi-layer coating.
  • the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
  • technical materials are to be understood as non-living materials that have been prepared for use in technology.
  • technical materials which are to be protected from 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.
  • 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.
  • Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation 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 slime 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:
  • 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.
  • 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.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include 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 pressure, e.g. aerosol
  • Propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.
  • Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates.
  • the following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, 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.
  • Possible emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phosphohpides, such as cephalins and lecithins, and synthetic phosphohpides.
  • 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
  • Active ingredient 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.
  • Famoxadon Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimo ⁇ h, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu ⁇ rimidol, Flusrimidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Flusrilidol, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione, Iprovalicarb,
  • Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Paclobutrazole pefurazoate, penconazole, pencycuron, phosdiphen, picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidone,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetcyclacis, tetraconazole, thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram, dioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutichl, triazoxid, triazoxid, triazoxide, triazoxide
  • Tridemo ⁇ h Trifloxystrobin, triflumizole, triforin, triticonazole,
  • N-formyl-N-hydroxy-DL-alanine sodium salt O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
  • Cadusafos Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron,
  • Chlormephos Chlo ⁇ yrifos, Chlo ⁇ yrifos M, Chlovaporthrin, Chromafenozide, Cis- Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Clothianidine, Cyanophos, Cycloprene, Cycloprothrin, Cyfluthrin, Cyhalothrinomethine, Cyatin
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrine, Pothrohrinate , Pyridaben, pyridathione,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoots, mold and diphasic fungi (e.g. against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as
  • 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 use the active compounds
  • 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
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • plants and their parts can be treated with active substances according to the invention.
  • plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” 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 varieties are plants with new properties ("traits"), which have been grown by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, breeds, bio and genotypes.
  • 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 an increase in the action of the substances and agents which can be used according to the invention, better plant growth, are increased
  • transgenic plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which contains them
  • traits 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, accelerated ripening, higher crop yields, higher quality and / or higher
  • Nutritional value of the crop products higher shelf life and / or workability of the crop 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 viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • the important ones are examples of transgenic plants Cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pumice, citrus fruits and grapes) are mentioned, with corn, soybeans, potatoes, cotton and rapeseed being particularly emphasized.
  • the properties (“traits”) are particularly emphasized of the plants' increased defense against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b ), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • the 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 e.g. "PAT” gene.
  • the genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soybeans), KnockOut®
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against
  • Phosphinotricin such as rapeseed
  • IMI® tolerance against imidazolinones
  • STS® tolerance against 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 future developed or future plant varieties with these or future-developed genetic traits.
  • the plants listed can be treated particularly advantageously with the compounds of the general formula (I) according to the invention.
  • the preferred ranges given above for the active ingredients also apply to the treatment of these plants.
  • Plant treatment with the compounds specifically listed in the present text should be particularly emphasized.
  • dimethylacetamide emulsifier 1.0 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.
  • Apple scab pathogen Venturia inaequalis and then remain in an incubation cabin for 1 day at approx. 20 ° C and 100% relative humidity.
  • the plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.
  • Botrytis test (bean) / protective
  • dimethylacetamide emulsifier 1.0 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 inoculated plants are placed in a darkened chamber at approx. 20 ° C and 100% relative humidity.
  • Botrytis test (bean) / protective
  • the medium was previously treated with a suitable concentration of spores or
  • Mycelium of the fungus to be tested is offset.
  • the resulting concentrations of the active ingredient are 0.1, 1, 10 and 100 ppm.
  • the resulting concentration of the emulsifier is 300 ppm.
  • the plates are then incubated for 3-5 days on a shaker at a temperature of 22 ° C. until sufficient growth can be determined in the untreated control.
  • the evaluation is carried out photometrically at a wavelength of 620 nm
  • Measured data of the various concentrations are used to calculate the dose of active ingredient which leads to a 50% inhibition of fungal growth compared to the untreated control (ED 50 ).
  • 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.
  • Temperature of about 20 ° C and a relative humidity of about 80% set up to promote the development of mildew pustules.
  • 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.
  • Solvent 50 parts by weight of N, N-dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water and the stated amount of emulsifier.
  • 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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  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne l'utilisation comme fongicides des composés de la formule (I) où W, X, Y, Z et CKE ont la signification donnée précédement.
PCT/EP2003/000026 2002-01-15 2003-01-03 Ceto-enols cycliques substitues par un biphenyle WO2003059065A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003206693A AU2003206693A1 (en) 2002-01-15 2003-01-03 Fungicidal biphenyl substituted cyclic ketoenols

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Application Number Priority Date Filing Date Title
DE10201239.3 2002-01-15
DE2002101239 DE10201239A1 (de) 2002-01-15 2002-01-15 Fungizide biphenylsubstituierte cyclische Ketoenole

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WO2003059065A1 true WO2003059065A1 (fr) 2003-07-24

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AU (1) AU2003206693A1 (fr)
DE (1) DE10201239A1 (fr)
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WO2008067910A1 (fr) * 2006-12-04 2008-06-12 Bayer Cropscience Ag Dérivés d'acide tétramique cis-alcoxyspirocycliques substitués par le biphényle
WO2008067911A1 (fr) * 2006-12-04 2008-06-12 Bayer Cropscience Ag Cétoénols spirocycliques substitués par le biphényle
EP2071952A1 (fr) 2007-12-21 2009-06-24 Bayer CropScience AG Utilisation de dérivés d'acide tétramique pour lutter contre les phytopathogènes par une application par irrigation ou au goutte-à-goutte
JP2009538844A (ja) * 2006-06-02 2009-11-12 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト アルコキシアルキル置換環状ケトエノール
EP2127522A1 (fr) * 2008-05-29 2009-12-02 Bayer CropScience AG Combinaisons de principes actifs presentant des propriétés insecticides et acaricides
WO2010081686A1 (fr) * 2009-01-19 2010-07-22 Bayer Cropscience Ag 1,3-diones bicycliques et leur utilisation comme insecticides, acaricides et/ou fongicides
WO2010127797A3 (fr) * 2009-05-06 2011-04-14 Bayer Cropscience Ag Composés de cyclopentanedione et leur utilisation comme insecticides, acaricides et/ou fongicides
WO2010081688A3 (fr) * 2009-01-19 2011-05-05 Bayer Cropscience Ag 4-phényl-pyrane-3,5-diones, 4-phényl-thiopyrane-3,5-diones et cyclohexanetriones et leur utilisation comme insecticides, acaricides et/ou fongicides
WO2011098440A2 (fr) 2010-02-10 2011-08-18 Bayer Cropscience Ag Cétoénols cyliques à substitution biphényle
JP2012515190A (ja) * 2009-01-19 2012-07-05 シンジェンタ リミテッド シクロペンタジオン由来の除草剤
WO2012101047A1 (fr) 2011-01-25 2012-08-02 Bayer Cropscience Ag Procédé de production de dérivés de la 1-h-pyrrolidine-2,4-dione
WO2012110519A1 (fr) 2011-02-17 2012-08-23 Bayer Cropscience Ag 3-(biphényle-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4,5]dec-3-en-2-ones substituées pour la thérapie et des cétoénols spirocycliques substitués par des halogènes
WO2012116960A1 (fr) 2011-03-01 2012-09-07 Bayer Cropscience Ag 2-acyloxy-pyrrolin-4-ones
WO2012165648A1 (fr) 2011-05-30 2012-12-06 Sumitomo Chemical Company, Limited Composés cyclohexanones et herbicides les comprenant
WO2013020888A1 (fr) 2011-08-05 2013-02-14 Bayer Intellectual Property Gmbh Utilisation de dérivés d'acide tétramique pour la lutte contre les pathogènes par application foliaire
US8389443B2 (en) 2008-12-02 2013-03-05 Bayer Cropscience Ag Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives
US8435549B2 (en) 2007-09-25 2013-05-07 Bayer Cropscience Ag Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives
US8518985B2 (en) 2009-03-11 2013-08-27 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
JP2014504624A (ja) * 2011-02-06 2014-02-24 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 処置用の（５ｓ，８ｓ）−３−（４’−クロロ−３’−フルオロ−４−メチルビフェニル−３−イル）−４−ヒドロキシ−８−メトキシ−１−アザスピロ［４．５］デカ−３−エン−２−オン（化合物Ａ）
JP2014040436A (ja) * 2003-08-14 2014-03-06 Bayer Cropscience Ag ４−ビフェニル置換ピラゾリジン−３，５−ジオン誘導体
WO2014084410A1 (fr) 2012-11-30 2014-06-05 Sumitomo Chemical Company, Limited Composés cyclohexanones et herbicides les comprenant
US8846946B2 (en) 2008-12-02 2014-09-30 Bayer Cropscience Ag Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives
US8859466B2 (en) 2007-08-02 2014-10-14 Bayer Cropscience Ag Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives

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JP2001026578A (ja) * 1999-05-11 2001-01-30 Sankyo Co Ltd Ｎ−置換ジヒドロピロール誘導体
WO2001009092A1 (fr) * 1999-07-30 2001-02-08 Bayer Aktiengesellschaft Ceto-enols cycliques a substitution biphenyle comme produits antiparasites

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US8173697B2 (en) 2006-06-02 2012-05-08 Bayer Cropscience Ag Alkoxyalkyl-substituted cyclic keto-enols
US20110130284A1 (en) * 2006-12-04 2011-06-02 Bayer Cropscience Ag Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives
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AU2007327961B2 (en) * 2006-12-04 2013-08-22 Bayer Intellectual Property Gmbh Biphenyl-substituted spirocyclic ketoenols
WO2008067910A1 (fr) * 2006-12-04 2008-06-12 Bayer Cropscience Ag Dérivés d'acide tétramique cis-alcoxyspirocycliques substitués par le biphényle
JP2010511642A (ja) * 2006-12-04 2010-04-15 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト シス−アルコキシスピロ環式ビフェニル置換されたテトラミン酸誘導体
JP2010511643A (ja) * 2006-12-04 2010-04-15 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト ビフェニル置換されたスピロ環式ケトエノール
US8993782B2 (en) * 2006-12-04 2015-03-31 Bayer Cropscience Ag Cis-alkoxyspirocyclic biphenyl-substituted tetramic acid derivatives
US9000189B2 (en) 2006-12-04 2015-04-07 Bayer Cropscience Ag Biphenyl-substituted spirocyclic ketoenols
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US8859466B2 (en) 2007-08-02 2014-10-14 Bayer Cropscience Ag Oxaspirocyclic spiro-substituted tetramic acid and tetronic acid derivatives
US8435549B2 (en) 2007-09-25 2013-05-07 Bayer Cropscience Ag Halogen alkoxy spirocyclic tetramic and tetronic acid derivatives
EP2071952A1 (fr) 2007-12-21 2009-06-24 Bayer CropScience AG Utilisation de dérivés d'acide tétramique pour lutter contre les phytopathogènes par une application par irrigation ou au goutte-à-goutte
WO2009146793A3 (fr) * 2008-05-29 2010-05-14 Bayer Cropscience Ag Combinaisons de principes actifs à propriétés insecticides et acaricides
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CN102281760B (zh) * 2009-01-19 2014-06-11 拜尔农作物科学股份公司 二环1，3-二酮及其作为杀昆虫剂、杀螨剂和/或杀菌剂的用途
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JP2012515190A (ja) * 2009-01-19 2012-07-05 シンジェンタ リミテッド シクロペンタジオン由来の除草剤
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AU2003206693A1 (en) 2003-07-30

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