WO2009037242A2 - Combinations comprising a fungicidal strain and an active compound - Google Patents

Combinations comprising a fungicidal strain and an active compound Download PDF

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Publication number
WO2009037242A2
WO2009037242A2 PCT/EP2008/062279 EP2008062279W WO2009037242A2 WO 2009037242 A2 WO2009037242 A2 WO 2009037242A2 EP 2008062279 W EP2008062279 W EP 2008062279W WO 2009037242 A2 WO2009037242 A2 WO 2009037242A2
Authority
WO
WIPO (PCT)
Prior art keywords
ustilago
methyl
phenyl
carboxamide
tilletia
Prior art date
Application number
PCT/EP2008/062279
Other languages
French (fr)
Other versions
WO2009037242A3 (en
Inventor
Ulrich Schöfl
Maria Scherer
Egon Haden
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39111809&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2009037242(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to CA2698560A priority Critical patent/CA2698560A1/en
Priority to JP2010525324A priority patent/JP2010539213A/en
Priority to EP18165991.3A priority patent/EP3381289B1/en
Priority to MX2012012397A priority patent/MX348283B/en
Priority to EP19153453.6A priority patent/EP3510869A1/en
Priority to US12/678,543 priority patent/US9078447B2/en
Priority to EP08804238A priority patent/EP2192841A2/en
Priority to PL10171539T priority patent/PL2292098T3/en
Priority to MX2012012399A priority patent/MX348284B/en
Priority to EP10171539.9A priority patent/EP2292098B1/en
Priority to BRPI0816948-9A priority patent/BRPI0816948B1/en
Priority to MX2010002423A priority patent/MX2010002423A/en
Priority to AU2008300629A priority patent/AU2008300629B2/en
Priority to UAA201004084A priority patent/UA106719C2/en
Priority to BR122017018225A priority patent/BR122017018225B1/en
Priority to KR1020157013685A priority patent/KR20150066600A/en
Priority to CN2008801065684A priority patent/CN101917856A/en
Priority to NZ583686A priority patent/NZ583686A/en
Priority to MX2012012398A priority patent/MX349309B/en
Priority to EA201000430A priority patent/EA018247B1/en
Application filed by Basf Se filed Critical Basf Se
Publication of WO2009037242A2 publication Critical patent/WO2009037242A2/en
Priority to IL204151A priority patent/IL204151A/en
Priority to MA32766A priority patent/MA31773B1/en
Priority to ZA2010/02715A priority patent/ZA201002715B/en
Publication of WO2009037242A3 publication Critical patent/WO2009037242A3/en
Priority to US14/731,791 priority patent/US9392797B2/en
Priority to PH12015502617A priority patent/PH12015502617B1/en
Priority to US15/184,691 priority patent/US9743674B2/en
Priority to US15/656,089 priority patent/US10212942B2/en
Priority to PH12019500097A priority patent/PH12019500097A1/en

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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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
    • A01N63/22—Bacillus
    • 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
    • A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/10—Pentachlorophenol
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/06—Nitrogen directly attached to an aromatic ring system
    • 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
    • A01N35/04—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 aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic 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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters 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
    • 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
    • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S435/00—Chemistry: molecular biology and microbiology
    • Y10S435/8215—Microorganisms
    • Y10S435/822—Microorganisms using bacteria or actinomycetales
    • Y10S435/832—Bacillus

Definitions

  • Combinations comprising a fungicidal strain and an active compound
  • the present invention relates to fungicidal compositions for controlling phytopathogenic harmful fungi comprising, as active components,
  • fungicidal strain selected from a) the Bacillus substilis strain with NRRL Accession No. B-21661 , and b) the Bacillus pumilus strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, or a metabolite produced by the respective strain that exhibits activity against plant pathogenic fungi;
  • B) strobilurins selected from the group consisting of 2-(2-(6-(3-chloro-2-methyl- phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl- acetamide and 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclo- propanecarboximidoylsulfanylmethy ⁇ -pheny ⁇ -acrylic acid methyl ester;
  • C) carboxamides selected from the group consisting of benalaxyl, benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxamide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4- yl)-nicotinamide, N-(2-(1 ,3-dimethylbutyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide, N-(4'-chloro-3',5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-chloro-3',5-difluoro- biphenyl-2-yl)-3-trifluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-pheny
  • R 3 , R 4 and R 5 independently of one another are hydrogen, cyano, nitro, halogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy,
  • heterocyclic compounds selected from the group consisting of 5-chloro-7-(4- methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro-pyridine-2,6-di- carbonitrile, N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4-dichloro- nicotinamide, N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4-dichloro- nicotinamide, diflumetorim, nitrapyrin, dodemorph-acetate, fluoroimid, blasti- cidin-S, chinomethionat, debacarb, o
  • E 1 is C 3 -Ci2-alkyl, C 2 -Ci 2 -alkenyl, C 5 -Ci 2 -alkoxyalkyl, C 3 -C 6 -cycloalkyl, phenyl or phenyl-Ci-C 4 -alkyl;
  • E 2 is Ci-Ci2-alkyl, C 2 -Ci 2 -alkenyl, Ci-C 4 -haloalkyl or Ci-C 4 -alkoxy-Ci-C 4 - alkyl;
  • R a is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C 2 -Cio-alkenyl, C 2 -Cio-alkynyl, Ci-C ⁇ -alkoxy, Ci-C ⁇ - alkylthio, Ci-C 6 -alkoxy-Ci-C 6 -alkyl or NR A R B ; R A , R B independently of one another are hydrogen or Ci-C ⁇ -alkyl; where the cyclic groups in E 1 and/or R a may be substituted by one to four groups R b : R b is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci- C ⁇ -haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or
  • E 3 is hydrogen, halogen, cyano, NR A R B , hydroxyl, mercapto, d-C ⁇ -alkyl, d-Ce-haloalkyl, C 3 -C 8 -cycloalkyl, Ci-C 6 -alkoxy, Ci-C 6 -alkylthio, C 3 -C 8 - cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl, C-i-C-io-alkyl- carbonyl, C-i-C-io-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-C10- alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio or Ci-C 6 -alkyl-S(O)m-;
  • n 0, 1 or 2;
  • A is CH or N
  • carbamates selected from the group consisting of methasulphocarb and propamocarb hydrochlorid;
  • F) other fungicides selected from the group consisting of metrafenone, dodine free base, guazatine-acetate, iminoctadine-triacetate, iminoctadine- tris(albesilate), kasugamycin-hydrochlorid-hydrat, dichlorophen, pentachloro- phenol and its salts, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxin-copper, prohexadione calcium, N- (cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2- phenyl acetamide, N'-(4-(4-chloro-3
  • the invention relates to a method for controlling harmful fungi using a composition of components 1 ) and 2), to the use of a component 1 ) with a component 2) for preparing such compositions, and also to agents and seed comprising such compositions.
  • strains (I), their mutants and the metabolites produced by the strains that exhibit activity against plant pathogenic fungi, referred to above as component 1), their preparation and their action against harmful fungi are known from WO 98/50422, WO 00/29426 and WO 00/58442, therein also referred to as AQ713 (QST713) and QST2808.
  • Isolates of bacteria of species Bacillus subtilis and Bacillus pumilus which are effective in inhibiting the growth of fungi of species botrytis cinerea and/or Alternaria brassicicola and a method of obtaining those isolates are also known from WO 93/18654.
  • Example 13 of WO 98/50422 already discloses that synergistic activity is obtained by the combined treatment of component 1) a) and azoxystrobin.
  • NRRL is the abbreviation for the Agricultural Research Service Culture Collection, an international depositary authority for the purposes of deposing microorganism strains under the BUDAPEST TREATY ON THE INTERNATIONAL RECOGNITION OF THE DEPOSIT OF MICROORGANISMS FOR THE PURPOSES OF PATENT PROCE- DURE, having the address National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, Illinois 61604, USA.
  • Suitable formulations of the Bacillus subtilis strain 1) a) are commercially available un- der the tradenames RHAPSODY ® , SERENADE ® MAX and SERENADE ® ASO from AgraQuest, Inc., USA.
  • Suitable formulations of the Bacillus pumilus strain 1 ) b) are commercially available under the tradenames SONATA ® and BALLAD ® Plus from AgraQuest, Inc., USA.
  • the active compounds (II) mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • N-(2-bicycloprop-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide is known from WO 03/074491 and can be prepared in the manner described therein.
  • the fungicidal activity of said compound against various harmful fungi is known from WO 2006/015866.
  • Isopyrazam is known from WO 04/035589 and can be prepared in the manner described therein or as described in WO 2007/068417.
  • the 1-methyl-pyrazol-4-ylcarboxanilides of formula (III) are known from the literature (cf., for example, EP-A 545 099, EP-A 589 301 , WO 99/09013, WO 2003/70705 and WO 2006/087343), or they can be prepared in the manner described therein.
  • Metrafenone 3'-bromo-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone, is known from US 5,945,567.
  • compositions, of components 1) and 2) defined at the outset.
  • simultaneous, that is joint or separate, application of componentws 1 ) and 2) or successive application of the components 1) and 2) allows better control of harmful fungi than is possible with the strains, their mutants and the metabolites produced by the strains on the one hand and with the individual compounds (II) on the other hand, alone (synergistic mixtures).
  • Component 1 embraces not only the isolated, pure cultures of the Bacillus substilis strain and the Bacillus pumilus strain, but also their suspensions in a whole broth culture or as a metabolite-containing supernatant or a purified metabolite obtained from a whole broth culture of the strain.
  • Whole broth culture refers to a liquid culture containing both cells and media.
  • Supernatant refers to the liquid broth remaining when cells grown in broth are removed by centrifugation, filtration, sedimentation, or other means well known in the art.
  • metabolite refers to any compound, substance or byproduct of a fermentation or a microorganism that has fungicidal activity.
  • Preferred component 1) is a fungicidal strain 1 ) a), the Bacillus substilis strain with
  • NRRL Accession No. B-21661 a mutant thereof having all the identifying characteris- tics of the strain, or a metabolite produced by the strain that exhibits activity against plant pathogenic fungi.
  • active compounds Il can be present in different crystal modifications, which may differ in biological activity. They also form part of component 2).
  • compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of A) azoles.
  • compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of B) strobilurins.
  • compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of C) carboxamides.
  • halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
  • Ci-C4-alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2- methylpropyl or 1 ,1-dimethylethyl, preferably methyl or ethyl;
  • Ci-C4-haloalkyl is a partially or fully halogenated Ci-C4-alkyl radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl
  • Ci-C 4 -alkoxy is OCH 3 , OC 2 H 5 , OCH 2 -C 2 H 5 , OCH(CH 3 ) 2 , n-butoxy, OCH(CHs)-C 2 H 5 , OCH 2 -CH(CHs) 2 or OC(CHs) 3 , preferably OCH 3 or OC 2 H 5 ;
  • Ci-C4-haloalkoxy is a partially or fully halogenated Ci-C4-alkoxy radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chloro- difluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluor
  • Ci-C 4 -alkylthio is SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH(CH 3 ) 2 , n-butylthio, SCH(CHs)-C 2 H 5 , SCH 2 -CH(CHs) 2 or SC(CHs) 3 , preferably SCH 3 or SC 2 H 5 .
  • Ci-C4-haloalkylthio is a partially or fully halogenated Ci-C4-alkylthio radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoro- methylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichloro- fluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro- 2-fluoroethylthio, 2-chloro-2,2-difluoro
  • Preferred 1-methylpyrazol-4-ylcarboxanilides III are, on the one hand, those in which X is hydrogen.
  • preferred compounds III are those in which X is fluorine.
  • R 1 is methyl or halomethyl, in particular CH 3 , CHF 2 , CH 2 F, CF 3 , CHFCl Or CF 2 CI.
  • R 2 is hydrogen, fluorine or chlorine, in particular hydrogen.
  • R 3 is halogen, Ci-C 4 - alkyl, CrC 4 -haloalkyl, d-C 4 -alkoxy, d-C 4 -haloalkoxy or d-C 4 -alkylthio, preferably halogen, methyl, halomethyl, methoxy, halomethoxy or methylthio, in particular F, Cl, CH 3 , CF 3 , OCH 3 , OCHF 2 , OCF 3 Or SCH 3 , particularly preferably fluorine.
  • compositions of a component 1 ) with a compo- nent 2) consisting of at least one active compound (II) selected from the group of D) heterocyclic compounds.
  • halogen is fluorine, chlorine, bromine or iodine.
  • alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 1 to 6, 1 to 10, 1 to 12 or 3 to 12 carbon atoms, for example Ci-C ⁇ -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-
  • haloalkyl straight-chain or branched alkyl radicals having 1 to 4, 1 to 6 or 1 to 10 car- bon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by halogen atoms as mentioned above: in particular C 1 -C 2 - haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoro- methyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chloro- difluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroe
  • alkenyl unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6, 2 to 10 or 2 to 12 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- methyl-2-butenyl, 1-methyl-3-but
  • alkynyl straight-chain or branched hydrocarbon radicals having 2 to 6 or 2 to 10 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 -alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-
  • cycloalkyl mono- or bicyclic saturated hydrocarbon radicals having 3 to 6 or 3 to 8 carbon ring members, for example C 3 -C 8 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; cycloalkoxy: mono- or bicyclic saturated hydrocarbon radicals which are attached via an oxygen atom (-O-);
  • cycloalkylthio mono- or bicyclic, saturated hydrocarbon radicals which are attached via a sulfur atom (-S-);
  • alkylthio saturated, straight-chain or branched hydrocarbon radicals which are attached via a sulfur atom (-S-);
  • alkylcarbonyl straight-chain or branched alkyl radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (-CO-);
  • alkoxy straight-chain or branched alkyl radicals which are attached via an oxygen atom (-O-);
  • alkoxyalkyl straight-chain or branched alkoxy radicals which are attached to an alkyl radical;
  • haloalkoxy straight-chain or branched alkoxy radicals, where some or all of the hydro- gen atoms in these radicals may be replaced by halogen;
  • alkoxycarbonyl alkoxy radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (-CO-);
  • alkenyloxycarbonyl alkenyl radicals which are attached via an oxygen atom (-O-) to a carbonyl group (-CO-);
  • alkynyloxycarbonyl alkynyl radicals which are attached via an oxygen atom (-O-) to a carbonyl group (-CO-);
  • phenylalkyl a phenyl group which is attached via saturated, straight-chain or branched alkyl radicals.
  • Preferred azolopyrimidin-7-ylamines IV are those compounds in which E 1 is straight- chain or branched C3-Ci2-alkyl or phenyl which may be substituted by one to three halogen or Ci-C4-alkyl groups.
  • the aliphatic chains in E 1 and E 2 or in E 1 or E 2 are not substituted by R a .
  • a preferred embodiment relates to compounds IV in which E 1 is straight-chain or branched Cs-do-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl or n-decyl.
  • a further embodiment relates to compounds IV in which E 1 is phenyl which is unsubsti- tuted or substituted by one to four radicals R b .
  • Preferred compounds IV are those in which E 1 is a substituted phenyl group which corresponds to a group Ar
  • L 1 to L 3 are halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , Ci-Cio-alkyl, Ci-C ⁇ - haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-C ⁇ -alkoxy; r and q independently of one another may be 0 or 1 strig, where NR A R B is as defined in formula IV and # denotes the bond to the azolopyrimidine skeleton.
  • L 1 is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , d-C ⁇ -alkyl, halomethyl and Ci-C2-alkoxy, preferably halogen, cyano, d-C ⁇ -alkyl, halomethyl or Ci-C2-alkoxy.
  • q is 0 or L 2 is one of the groups mentioned above and q is 1.
  • r is 0 or L 3 is halogen, cyano, hydroxyl, mercapto, nitro, NR A R B , d-C ⁇ -alkyl, halomethyl or Ci-C2-alkoxy and r is 1.
  • r is zero.
  • E 2 is straight-chain or branched C1-C12- alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl or Ci-C 4 -haloalkyl.
  • E 2 is methyl, ethyl, n- propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoro- methyl or methoxymethyl.
  • E 3 is hydrogen.
  • E 3 is amino.
  • One embodiment of the compounds IV relates to those in which A is N. These compounds correspond to formula IVa in which the variables are as defined for formula IV:
  • the sum of the carbon atoms in the carbon radicals of E 1 and E 2 is not more than 12.
  • azolopyrimidin-7-ylamines IV are those listed in Table 1 :
  • compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of E) carbamates.
  • compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungicides.
  • compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungi- cides selected from the group consisting of metrafenone, dodine free base, guazatine- acetate, iminoctadine-triacetate, iminoctadine-tris(albesilate), kasugamycin- hydrochlorid-hydrat, dichlorophen, pentachlorophenol and its salts, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxin-copper and prohexadione cal- cium, in particular metrafenone, dodine free base, guazatine-acetate, iminoc
  • compositions comprising a component 1 ), wherein component 2) consists of two of the active compounds (II) mentioned above.
  • compositions comprising, in addition to component 1) and component 2) consisting of one active compound (II) mentioned above, a further fungicidally active compound V selected from active compound groups G) to M):
  • H) strobilurins selected from the group consisting of azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, methyl (2-chloro-5-[1-(3- methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methyl- pyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate and methyl 2-(ortho-(2,5-di- methylphenyloxymethylene)phenyl)-3-methoxyacrylate; J) carboxamides selected from the group consisting of carboxin, boscalid, fen- hexamid, flutolanil, furametpyr, mepro
  • heterocyclic compounds selected from the group consisting of fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropi- morph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iod
  • L) carbamates selected from the group consisting of mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flub- enthiavalicarb, propamocarb, 4-fluorophenyl N-(1-(1-(4-cyanophenyl)ethane- sulfonyl)but-2-yl)carbamate, methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonyl- amino-3-methylbutyrylamino)propanoate and carbamate oxime ethers of the formula Vl
  • Z is N or CH
  • M) other fungicides selected from the group consisting of guanidine, dodine, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane, organometallic compounds: fentin salts such as fentin acetate, organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlor- benzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, inorganic
  • the active compounds V mentioned above, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
  • an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, met
  • an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole,
  • an active compound selected from the group of the other fungicides M) selected from the group consisting of dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sul
  • Active compound combinations of a component 1) and a component 2) conprising a compound Il selected from group A): Mixture Component 1 ) Component 2)
  • compositions comprising the components 1 ) and 2), or the simultaneous, that is joint or separate, use of a component 1) and a component 2), are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi in particular from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomy- cetes (syn. Oomycetes). Some of them are systemically active and can be used in crop protection as foliar fungicides, as soil fungicides and as fungicides for seed dressing.
  • compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; beet, for example sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cu
  • compounds I and compositions thereof are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • field crops such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant propagation material is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be mentioned. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
  • cultivación of plant propagation materials with compounds I and composi- tions thereof is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
  • cultivated plants is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering.
  • Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • cultiva plants is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.
  • specific classes of herbicides such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • GS glutamine synthetase
  • EP-A-0242236, EP-A-242246) or oxynil herbi- cides see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering.
  • mutagenesis for example Clearfield ® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox.
  • cultiva plants is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as ⁇ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi ) or Cry ⁇ c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp.
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of sodium or calcium channels
  • these insecticidal pro- teins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
  • cultivars are to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solarium bulbocastanum) or T4-lyso- zym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solarium bulbocastanum
  • T4-lyso- zym e. g. potato cultivar
  • cultiva plants is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil con- tent or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • cultiva plants is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape).
  • cultiva plants is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora ® potato).
  • protein as used herein is to be understood as an oligopeptide or polypeptide or molecule made up of polypeptides including expressly also pre-proteins, hybrid proteins, peptides, truncated or otherwise modified proteins including those derived from post-transcriptional modifications such as acylation (e.g. acetylation, the addition of an acetyl group, usually at the N-terminus of the protein), alkylation, the addition of an alkyl group (e.g.
  • the plants or seed treated with the combinations comprising components 1 ) and 2) may by wildlife types, plants or seed obtained by breeding and transgenic plants as well as their seed.
  • Rhizoctonia cerealis Pyrenophora subalpina Rhizoctonia choussii Pyrenophora sudetica Rhizoctonia coniothecioides Pyrenophora suhantarctica Rhizoctonia cundida Pyrenophora syntrichiae Rhizoctonia dichoroma Pyrenophora szaferiana Rhizoctonia dimorpha Pyrenophora teres Rhizoctonia endophytica Pyrenophora teres f. makulata Rhizoctonia endophytica vor. filicata Pyrenophora teres subsp.
  • Rhizoctonia gracilis Pyrenophora tritici repentis Rhizoctonia griseo Pyricularia oryzae Rhizoctonia hiemalis Pythium aphanidermatum Rhizoctonia juniperi Pythium debaryanum Rhizoctonia lamallifera Pythium irregulare Rhizoctonia leguminicola Pythium myriotylum Rhizoctonia lilacina Pythium ultimum Rhizoctonia luoini Ramularia collocygni Rhizoctonia macrosclerotia Rhizoctonia aerea Rhizoctonia melongenae Rhizoctonia alba Rhizoctonia microsclerotia Rhizoctonia alpina Rhizoctonia monilioides Rhizoctonia anaticula Rhizoctonia monteithiana Rhizoctonia muneratii Tilletia aegop
  • Rhizoctonia solani f. paroketea Tilletia bangalorensis
  • Rhizoctonia solani forma specialis Tilletia barclayana
  • Rhizoctonia solani var. cedri-deodorae Tilletia biharica
  • Rhizoctonia tomato Tilletia brevifaciens Rhizoctonia tomato Tilletia brevifaciens
  • Ustilago flectens Ustilago hypodytes f. sporaboli
  • compositions comprising the components 1 ) and 2) are particularly suitable for controlling phytopathogenic fungi in barley (e.g. Pyrenophora teres, Rhynchosporium secalis,Puccinia hordei,Puccinia striiformis, Blumeria graminis, Ramularia collo-cygni / Physiological leaf spots, Microdochium nivale, Typhula incarnata, Pseudocercosporella herpotrichoides, Fusarium culmorum, Rhizoctonia cerealis, Gaeumannomyces graminis) and soybeans (e.g.
  • Phakopsora pachyrhizi Microsphaera diffusa, Septoria glycines, Cercospora sojina, Cercospora kikuchii, Corynespora cassiicola, Colletotrichum truncatum, Peronospora manshurica, Alternaria spp., Phomopsis phaseoli, Diaporthe phaseolorum, Phialophora gregata, Fusarium solani, Sclerotinia sclerotiorum, Sclerotinia rolfsii, Phytopthora megasperma, Rhizoctonia solani, Dematophora necatrix, Macrophomina phaseolina).
  • compositions are particularly suitable for controlling phytopathogenic fungi in soybeans, vegetables and fruit crops.
  • compositions according to the invention are furthermore suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
  • harmful fungi Ascomycetes, such as Ophio- stoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chae- tomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Po- ria spp., Serpula spp.
  • Tyromyces spp. Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.
  • compositions to useful plants may also lead to an increase in the crop yield.
  • the components 1) and 2) can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not hav- ing any effect on the result of the control measures.
  • compositions When preparing the compositions, it is preferred to employ the commercially available formulations of components 1 ) and 2), to which further compounds active against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbi- cidal or growth-regulating active compounds or fertilizers may be added.
  • harmful fungi or other pests such as insects, arachnids or nematodes, or else herbi- cidal or growth-regulating active compounds or fertilizers may be added.
  • compositions comprising component 1 ) and 2), wherein component 2) consists of only one active ingredient (II), are employed.
  • component 2) consists of two or, if appropriate, more active components may be advantageous.
  • Suitable further active components in the above sense are in particular the active compounds Il mentioned at the outset, and in particular the preferred active compounds Il mentioned above.
  • Components 1 ) and 2) are usually employed in a weight ratio of from 100:1 to 1 :100, preferably from 30:1 to 1 :30, in particular from 15:1 to 1 :15.
  • the further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to component 1 ).
  • the application rates for component 1 are generally from 1 I to 100 I broth containing the strain per hectare, preferably from 1 I to 50 I/ha, in particular from 1 to 20 I/ha.
  • the application rates for component 2) are generally from 1 to 2000 g/ha, preferably from 10 to 1500 g/ha, in particular from 40 to 1000 g/ha.
  • the method for controlling harmful fungi is carried out by the separate or joint applica- tion of a component 1 ) and a component 2), or a composition comprising components 1 ) and 2), by spraying or dusting the seeds, the plants or the soils before or after sowing of the plants or before or after emergence of the plants.
  • compositions according to the invention can be converted into customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • customary formulations for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the mixture according to the invention.
  • the formulations are prepared in a known manner, for example by extending the single components with solvents and/or carriers, if desired using emulsifiers and dispersants.
  • Solvents/auxiliaries suitable for this purpose are essentially:
  • aromatic solvents for example Solvesso ® products, xylene
  • paraffins for example mineral oil fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • pyrrolidones N-methylpyrrolidone, N-octylpyrrolidone
  • acetates glycols
  • fatty acid dimethylamides for fatty acids and fatty acid esters.
  • solvent mixtures may also be used.
  • ground natural minerals for example kaolins, clays, talc, chalk
  • ground synthetic minerals for example highly disperse silica, silicates
  • emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
  • Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene- sulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy- ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tribu
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin
  • Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth
  • compositions within the present invention it may be advantageous to formulate the whole broth culture, supernatant and/or metabolite with components that aid dispersion and adhesion.
  • the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the components.
  • the active compounds (II) are employed in a purity of from 90% to 100%, preferably
  • a composition according to the invention 10 parts by weight of a composition according to the invention are dissolved in 90 parts by weight of water or in a water-soluble solvent.
  • wetting agents or other auxiliaries are added. Dilution with water results in a formulation having a content of 10% by weight of components 1 ) and 2) is obtained.
  • a composition according to the invention 20 parts by weight of a composition according to the invention are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion having a content of 0% by weight of components 1 ) and 2).
  • a dispersant for example polyvinylpyrrolidone
  • compositions according to the invention 15 parts by weight of a composition according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion.
  • the formulation has a content of 15% by weight of components 1 ) and 2).
  • Emulsions 25 parts by weight of a composition according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This composition is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • the formulation has a content of 25% by weight of components 1 ) and 2).
  • a composition according to the invention 20 parts by weight of a composition according to the invention are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine suspension. Dilution with water gives a stable suspension having a content of 20% by weight of components 1 ) and 2).
  • Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a composition according to the invention are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution having a content of 50% by weight of components 1 ) and 2).
  • WP, SP Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a composition according to the invention are ground in a rotor- stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution having a content of 75% by weight of components 1 ) and 2).
  • a composition according to the invention is ground finely and associated with 99.5 parts by weight of carriers.
  • Current methods are extrusion, spray- drying or the fluidized bed. This gives granules to be applied undiluted having a content of 0.5% of weight of components 1 ) and 2).
  • Components 1 ) and 2) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring.
  • the use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of components 1) and 2) according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • a wetting agent e.g., tackifier, dispersant or emulsifier
  • concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.
  • concentrations of the components in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 100%, preferably from 0.01 to 100%.
  • Components 1 ) and 2) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply components 1 ) and 2) without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents or adjuvants may be added to the component 1 ) or 2), even, if appropriate, not until immediately prior to use (tank mix). These agents are typically admixed with component 1 ) or 2) according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1.
  • Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example Break Thru S 240 ® ; alcohol alkoxylates, for example Atplus 245 ® , Atplus MBA 1303 ® , Plurafac LF 300 ® and Lutensol ON 30 ® ; EO/PO block polymers, for example Pluronic RPE 2035 ® and Genapol B ® ; alcohol ethoxylates, for example Lutensol XP 80 ® ; and sodium dioctylsulfosuccinate, for example Leophen RA ® .
  • Components 1 ) and 2) or the composition comprising components 1) and 2), or the corresponding formulations, are applied by treating the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free from them with a fungicidally effective amount of the composition or, in the case of separate application, of the components 1 ) and 2) separately.
  • Application can be before or after the infection by harmful fungi.
  • Components 1 ) and 2) were prepared as a stock solution comprising 25 mg of active compound which was made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol ® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99:1. The mixture was then made up to 100 ml with water. This stock solution was diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.
  • Uniperol ® EL wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols
  • the efficacy (E) is calculated as follows using Abbot's formula:
  • An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.

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Abstract

Fungicidal mixtures, comprising 1) a fungicidal strain (I) selected from a) the Bacillus substilis strain with NRRL Accession No. B-21661, and b) the Bacillus pumilus strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, or a metabolite produced by the respective strain that exhibits activity against plant pathogenic fungi, and 2) at least one chemical compound (II), selected from the active compound groups A) to F): A) azoles; B) strobilurins; C) carboxamides; D) heterocyclic compounds; E) carbamates; F) other fungicides; in a synergistically effective amount, methods for controlling harmful fungi using compositions of components 1) and 2), the use of a component 1) with acomponent 2) for preparing such compositions, and also fungicidal agents and seed comprising such compositions.

Description

Combinations comprising a fungicidal strain and an active compound
Description
The present invention relates to fungicidal compositions for controlling phytopathogenic harmful fungi comprising, as active components,
1 ) a fungicidal strain (I) selected from a) the Bacillus substilis strain with NRRL Accession No. B-21661 , and b) the Bacillus pumilus strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, or a metabolite produced by the respective strain that exhibits activity against plant pathogenic fungi;
and
2) at least one chemical compound (II), selected from the active compound groups A) to F):
A) azoles selected from the group consisting of azaconazole, diniconazole-M, oxpoconazol, paclobutrazol, uniconazol, 1-(4-chloro-phenyl)-2-([1 ,2,4]triazol-1- yl)-cycloheptanol and imazalil-sulfphate;
B) strobilurins selected from the group consisting of 2-(2-(6-(3-chloro-2-methyl- phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N-methyl- acetamide and 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclo- propanecarboximidoylsulfanylmethy^-pheny^-acrylic acid methyl ester;
C) carboxamides selected from the group consisting of benalaxyl, benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxamide, 2-chloro-N-(1 ,1 ,3-trimethyl-indan-4- yl)-nicotinamide, N-(2-(1 ,3-dimethylbutyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H- pyrazole-4-carboxamide, N-(4'-chloro-3',5-difluoro-biphenyl-2-yl)-3- difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-chloro-3',5-difluoro- biphenyl-2-yl)-3-trifluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4- carboxamide, N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-
1 H-pyrazole-4-carboxamide, fluopyram, N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)- 3-formylamino-2-hydroxy-benzamide, oxytetracyclin, silthiofam, N-(6-methoxy- pyridin-3-yl) cyclopropanecarboxylic acid amide, penthiopyrad, isopyrazam and a 1-methyl-pyrazol-4-ylcarboxamide of the formula III
Figure imgf000003_0001
in which the substituents are as defined below: X is hydrogen or fluorine; R1 is Ci-C4-alkyl or Ci-C4-haloalkyl; R2 is hydrogen or halogen;
R3, R4 and R5 independently of one another are hydrogen, cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy,
Ci-C4-alkylthio or Ci-C4-haloalkyl;
heterocyclic compounds selected from the group consisting of 5-chloro-7-(4- methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5-trichloro-pyridine-2,6-di- carbonitrile, N-(1-(5-bromo-3-chloro-pyridin-2-yl)-ethyl)-2,4-dichloro- nicotinamide, N-((5-bromo-3-chloro-pyridin-2-yl)-methyl)-2,4-dichloro- nicotinamide, diflumetorim, nitrapyrin, dodemorph-acetate, fluoroimid, blasti- cidin-S, chinomethionat, debacarb, oxolinic acid, piperalin and an azolopyrimidin-7-ylamine of the formula IV
Figure imgf000003_0002
in which the substituents have the following meanings: E1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl; E2 is Ci-Ci2-alkyl, C2-Ci2-alkenyl, Ci-C4-haloalkyl or Ci-C4-alkoxy-Ci-C4- alkyl;
where the aliphatic chains in E1 and/or E2 may be substituted by one to four identical or different groups Ra:
Ra is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, Ci-Cio-haloalkyl, C3-C8-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-Cβ-alkoxy, Ci-Cβ- alkylthio, Ci-C6-alkoxy-Ci-C6-alkyl or NRARB; RA, RB independently of one another are hydrogen or Ci-Cβ-alkyl; where the cyclic groups in E1 and/or Ra may be substituted by one to four groups Rb: Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, Ci- Cβ-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-Cβ-alkoxy;
E3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, d-Cε-alkyl, d-Ce-haloalkyl, C3-C8-cycloalkyl, Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C8- cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl, C-i-C-io-alkyl- carbonyl, C-i-C-io-alkoxycarbonyl, C2-Cio-alkenyloxycarbonyl, C2-C10- alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio or Ci-C6-alkyl-S(O)m-;
m is 0, 1 or 2;
A is CH or N;
E) carbamates selected from the group consisting of methasulphocarb and propamocarb hydrochlorid;
F) other fungicides selected from the group consisting of metrafenone, dodine free base, guazatine-acetate, iminoctadine-triacetate, iminoctadine- tris(albesilate), kasugamycin-hydrochlorid-hydrat, dichlorophen, pentachloro- phenol and its salts, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxin-copper, prohexadione calcium, N- (cyclopropylmethoxyimino-(6-difluoromethoxy-2,3-difluoro-phenyl)-methyl)-2- phenyl acetamide, N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- phenyl)-N-ethyl-N-methyl formamidine, N'-(4-(4-fluoro-3-trifluoromethyl- phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine, N'-(2-methyl-5- trifluormethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine and N'-(5-difluormethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)- N-ethyl-N-methyl formamidine;
in a synergistically effective amount.
Moreover, the invention relates to a method for controlling harmful fungi using a composition of components 1 ) and 2), to the use of a component 1 ) with a component 2) for preparing such compositions, and also to agents and seed comprising such compositions.
The strains (I), their mutants and the metabolites produced by the strains that exhibit activity against plant pathogenic fungi, referred to above as component 1), their preparation and their action against harmful fungi are known from WO 98/50422, WO 00/29426 and WO 00/58442, therein also referred to as AQ713 (QST713) and QST2808.
Isolates of bacteria of species Bacillus subtilis and Bacillus pumilus which are effective in inhibiting the growth of fungi of species botrytis cinerea and/or Alternaria brassicicola and a method of obtaining those isolates are also known from WO 93/18654.
Example 13 of WO 98/50422 already discloses that synergistic activity is obtained by the combined treatment of component 1) a) and azoxystrobin.
NRRL is the abbreviation for the Agricultural Research Service Culture Collection, an international depositary authority for the purposes of deposing microorganism strains under the BUDAPEST TREATY ON THE INTERNATIONAL RECOGNITION OF THE DEPOSIT OF MICROORGANISMS FOR THE PURPOSES OF PATENT PROCE- DURE, having the address National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, Illinois 61604, USA.
Suitable formulations of the Bacillus subtilis strain 1) a) are commercially available un- der the tradenames RHAPSODY®, SERENADE® MAX and SERENADE® ASO from AgraQuest, Inc., USA.
Suitable formulations of the Bacillus pumilus strain 1 ) b) are commercially available under the tradenames SONATA® and BALLAD® Plus from AgraQuest, Inc., USA.
However, the known strains (I), their mutants and the metabolites produced by the strains are, in particular at low application rates, not entirely satisfactory.
The active compounds (II) mentioned above as component 2), their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
N-(2-bicycloprop-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide is known from WO 03/074491 and can be prepared in the manner described therein. The fungicidal activity of said compound against various harmful fungi is known from WO 2006/015866.
Isopyrazam is known from WO 04/035589 and can be prepared in the manner described therein or as described in WO 2007/068417.
The 1-methyl-pyrazol-4-ylcarboxanilides of formula (III) are known from the literature (cf., for example, EP-A 545 099, EP-A 589 301 , WO 99/09013, WO 2003/70705 and WO 2006/087343), or they can be prepared in the manner described therein.
The azolopyrimidin-7-ylamines IV, their preparation and their action against harmful fungi are known from the literature (EP-A 71 792; EP-A 141 317; WO 03/009687;
WO 05/087771 ; WO 05/087772; WO 05/087773; WO 2005/087772; WO 2006/087325; WO 2006/092428).
Metrafenone, 3'-bromo-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone, is known from US 5,945,567.
It was an object of the present invention, with a view to reducing the application rates and broadening the activity spectrum of the strains (I) and compounds (II), to provide compositions which, at a reduced total amount of active compounds applied, have improved activity against harmful fungi, in particular for certain indications.
We have accordingly found that this object is achieved by the compositions, of components 1) and 2), defined at the outset. Moreover, we have found that simultaneous, that is joint or separate, application of componentws 1 ) and 2) or successive application of the components 1) and 2) allows better control of harmful fungi than is possible with the strains, their mutants and the metabolites produced by the strains on the one hand and with the individual compounds (II) on the other hand, alone (synergistic mixtures).
By simultaneous, that is joint or separate, application of components 1 ) and 2), the fungicidal activity is increased in a superadditive manner.
Component 1 ) embraces not only the isolated, pure cultures of the Bacillus substilis strain and the Bacillus pumilus strain, but also their suspensions in a whole broth culture or as a metabolite-containing supernatant or a purified metabolite obtained from a whole broth culture of the strain.
" Whole broth culture" refers to a liquid culture containing both cells and media. " Supernatant" refers to the liquid broth remaining when cells grown in broth are removed by centrifugation, filtration, sedimentation, or other means well known in the art.
The term " metabolite" refers to any compound, substance or byproduct of a fermentation or a microorganism that has fungicidal activity.
Preferred component 1) is a fungicidal strain 1 ) a), the Bacillus substilis strain with
NRRL Accession No. B-21661 , a mutant thereof having all the identifying characteris- tics of the strain, or a metabolite produced by the strain that exhibits activity against plant pathogenic fungi.
Many of the active compounds Il can be present in different crystal modifications, which may differ in biological activity. They also form part of component 2).
Preference is given to compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of A) azoles.
Preference is also given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of B) strobilurins.
Preference is given to compositions of a component 1) with a component 2) consisting of at least one active compound (II) selected from the group of C) carboxamides.
Among the group of C) carboxamides, penthiopyrad, N-(2-(1 ,3-dimethylbutyl)-phenyl)- 1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(trans-2-bicyclopropyl-2-yl- phenyl)-3-difluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide and the 1-methyl- pyrazol-4-ylcarboxanilides of the formula III are preferred.
In the formula III, halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
Ci-C4-alkyl is methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2- methylpropyl or 1 ,1-dimethylethyl, preferably methyl or ethyl;
Ci-C4-haloalkyl is a partially or fully halogenated Ci-C4-alkyl radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, heptafluoropropyl or nonafluorobutyl, in particular halomethyl, with particular preference CH2-CI, CH(CI)2, CH2-F, CHF2, CF3, CHFCI, CF2CI or CF(CI)2, in particular CHF2 or CF3;
Ci-C4-alkoxy is OCH3, OC2H5, OCH2-C2H5, OCH(CH3)2, n-butoxy, OCH(CHs)-C2H5, OCH2-CH(CHs)2 or OC(CHs)3, preferably OCH3 or OC2H5; Ci-C4-haloalkoxy is a partially or fully halogenated Ci-C4-alkoxy radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chloro- difluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2- difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, heptafluoropropoxy or nonafluorobutoxy, in particular halomethoxy, particularly preferably OCH2-CI, OCH(CI)2, OCH2-F, OCH(F)2, OCF3, OCHFCI, OCF2CI Or OCF(CI)2;
Ci-C4-alkylthio is SCH3, SC2H5, SCH2-C2H5, SCH(CH3)2, n-butylthio, SCH(CHs)-C2H5, SCH2-CH(CHs)2 or SC(CHs)3, preferably SCH3 or SC2H5.
Ci-C4-haloalkylthio is a partially or fully halogenated Ci-C4-alkylthio radical, where the halogen atom(s) is/are in particular fluorine, chlorine and/or bromine, i.e., for example, chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoro- methylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichloro- fluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1- fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro- 2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-tri- chloroethylthio, pentafluoroethylthio, heptafluoropropylthio or nonafluorobutylthio, in particular halomethylthio, particularly preferably SCF3;
Preferred 1-methylpyrazol-4-ylcarboxanilides III are, on the one hand, those in which X is hydrogen.
On the other hand, preferred compounds III are those in which X is fluorine.
For the mixtures according to the invention, preference is given to compounds of the formula III in which R1 is methyl or halomethyl, in particular CH3, CHF2, CH2F, CF3, CHFCl Or CF2CI.
Preference is furthermore given to compounds III in which R2 is hydrogen, fluorine or chlorine, in particular hydrogen.
Preference is furthermore given to those compounds III in which R3 is halogen, Ci-C4- alkyl, CrC4-haloalkyl, d-C4-alkoxy, d-C4-haloalkoxy or d-C4-alkylthio, preferably halogen, methyl, halomethyl, methoxy, halomethoxy or methylthio, in particular F, Cl, CH3, CF3, OCH3, OCHF2, OCF3 Or SCH3, particularly preferably fluorine.
Moreover, preference is given to those compounds III in which R4 is halogen, in par- ticular fluorine. Preference is furthermore given to those compounds III in which R5 is halogen, in particular fluorine.
Among those 1-methylpyrazol-4-ylcarboxanilides III where X is hydrogen, particular preference is given to N-(2'-fluoro-4'-chloro-5'-methoxybiphenyl-2-yl)-3-trifluoromethyl-1- methyl-1 H-pyrazole-4-carboxamide, N-(2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl)- 3-trifluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(3',4',5'-trifluorobiphenyl-2-yl)- 3-trifluoromethyl-1-methyl-1 H-pyrazole-4-carboxamide, N-(2',4',5'-trifluorobiphenyl-2-yl)- 3-trifluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(2'-fluoro-4'-chloro-5'- methoxybiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-
(2',3',4'-trifluorobiphenyl-2-yl)-3-trifluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N- (2'-fluoro-4'-chloro-5'-methylbiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(2',4',5'-trifluorobiphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole- 4-carboxamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-fluoromethyl-1 -methyl-1 H-pyrazole-4- carboxamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorodifluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl-1- methyl-1 H-pyrazole-4-carboxamide, N-(2',3',4'-trifluorobiphenyl-2-yl)-3-fluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide, N-(2',4',5'-trifluorobiphenyl-2-yl)-3-fluoro-methyl- 1 -methyl-1 H-pyrazole-4-carboxamide, N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide and N-(4'-trifluoromethylthio-biphenyl-2-yl)- 1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide.
Among those 1-methylpyrazol-4-ylcarboxanilides I where X is fluorine, particular preference is given to N-(3',4'-dichloro-3-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl- 1 H-pyrazole-4-carboxamide, N-(3',4'-dichloro-3-fluorobiphenyl-2-yl)-1 -methyl-3- difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-difluoro-3-fluorobiphenyl-2-yl)-1 - methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-difluoro-3-fluorobiphenyl- 2-yl)-1 -methyl-3-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3'-chloro-4'-fluoro-3- fluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'- dichloro-4-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-difluoro-4-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H-pyrazole-4- carboxamide, N-(3',4'-dichloro-4-fluorobiphenyl-2-yl)-1 -methyl-3-difluoromethyl-1 H- pyrazole-4-carboxamide, N-(3',4'-difluoro-4-fluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3'-chloro-4'-fluoro-4-fluorobiphenyl-2-yl)- 1 -methyl-3-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-dichloro-5- fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-difluoro-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H-pyrazole-4- carboxamide, N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-1 -methyl-3-difluoromethyl-1 H- pyrazole-4-carboxamide, N-(3',4'-difluoro-5-fluorobiphenyl-2-yl)-1 -methyl-3- difluoromethyl-1 H-pyrazole-4-carboxamide, N-(3',4'-dichloro-5-fluorobiphenyl-2-yl)-1 ,3- dimethyl-1 H-pyrazole-4-carboxamide, N-(3'-chloro-4'-fluoro-5-fluorobiphenyl-2-yl)-1 - methyl-3-difluoromethyl-1 H-pyrazole-4-carboxamide, N-(4'-fluoro-4-fluorobiphenyl-2-yl)- 1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(4'-fluoro-5-fluorobiphenyl-2- yl)-1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(4'-chloro-5- fluorobiphenyl-2-yl)-1 -methyl-3-trifluoromethyl-1 H-pyrazole-4-carboxamide, N-(4'-methyl-5-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H-pyrazole-4- carboxamide, N-(4'-fluoro-5-fluorobiphenyl-2-yl)-1 ,3-dimethyl-1 H-pyrazole-4- carboxamide, N-(4'-chloro-5-fluorobiphenyl-2-yl)-1 ,3-dimethyl-1 H-pyrazole-4- carboxamide, N-(4'-methyl-5-fluorobiphenyl-2-yl)-1 ,3-dimethyl-1 H-pyrazole-4- carboxamide, N-(4'-fluoro-6-fluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1 H- pyrazole-4-carboxamide and N-(4'-chloro-6-fluorobiphenyl-2-yl)-1 -methyl-3- trifluoromethyl-1 H-pyrazole-4-carboxamide.
Preference is furthermore also given to compositions of a component 1 ) with a compo- nent 2) consisting of at least one active compound (II) selected from the group of D) heterocyclic compounds.
Among the D) heterocyclic compounds, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine and the azolopyrimidin-7-ylamines of the formula IV are preferred.
In the formula IV, halogen is fluorine, chlorine, bromine or iodine.
alkyl: saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 1 to 6, 1 to 10, 1 to 12 or 3 to 12 carbon atoms, for example Ci-Cβ-alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1 ,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2- methylpropyl;
haloalkyl: straight-chain or branched alkyl radicals having 1 to 4, 1 to 6 or 1 to 10 car- bon atoms (as mentioned above), where some or all of the hydrogen atoms in these radicals may be replaced by halogen atoms as mentioned above: in particular C1-C2- haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoro- methyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chloro- difluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl or 1 ,1 ,1 -trif luoroprop-2- yi;
alkenyl: unsaturated straight-chain or branched hydrocarbon radicals having 2 to 6, 2 to 10 or 2 to 12 carbon atoms and one or two double bonds in any position, for example C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2- methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3- methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1- dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2-dimethyl-2-propenyl, 1 -ethyl-1 - propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1- methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1- methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1- methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1- methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl-2-butenyl, 1 ,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2-dimethyl- 2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl- 2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1 -ethyl-1 -butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl- 2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1 -methyl-2-propenyl, 1-ethyl-2-methyl-1 -propenyl or 1-ethyl-2-methyl-2-propenyl;
alkynyl: straight-chain or branched hydrocarbon radicals having 2 to 6 or 2 to 10 carbon atoms and one or two triple bonds in any position, for example C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl- 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl- 1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1-dimethyl-3-butynyl, 1 ,2-dimethyl-3-butynyl, 2,2-dimethyl- 3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1 -ethyl-1 -methyl-2-propynyl;
cycloalkyl: mono- or bicyclic saturated hydrocarbon radicals having 3 to 6 or 3 to 8 carbon ring members, for example C3-C8-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl; cycloalkoxy: mono- or bicyclic saturated hydrocarbon radicals which are attached via an oxygen atom (-O-);
cycloalkylthio: mono- or bicyclic, saturated hydrocarbon radicals which are attached via a sulfur atom (-S-);
alkylthio: saturated, straight-chain or branched hydrocarbon radicals which are attached via a sulfur atom (-S-);
alkylcarbonyl: straight-chain or branched alkyl radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (-CO-);
alkoxy: straight-chain or branched alkyl radicals which are attached via an oxygen atom (-O-);
alkoxyalkyl: straight-chain or branched alkoxy radicals which are attached to an alkyl radical;
haloalkoxy: straight-chain or branched alkoxy radicals, where some or all of the hydro- gen atoms in these radicals may be replaced by halogen;
alkoxycarbonyl: alkoxy radicals which have 1 to 10 carbon atoms and are attached via a carbonyl group (-CO-);
alkenyloxycarbonyl: alkenyl radicals which are attached via an oxygen atom (-O-) to a carbonyl group (-CO-);
alkynyloxycarbonyl: alkynyl radicals which are attached via an oxygen atom (-O-) to a carbonyl group (-CO-);
phenylalkyl: a phenyl group which is attached via saturated, straight-chain or branched alkyl radicals.
Preferred azolopyrimidin-7-ylamines IV are those compounds in which E1 is straight- chain or branched C3-Ci2-alkyl or phenyl which may be substituted by one to three halogen or Ci-C4-alkyl groups.
In one embodiment of the compounds IV, the aliphatic chains in E1 and E2 or in E1 or E2 are not substituted by Ra. A preferred embodiment relates to compounds IV in which E1 is straight-chain or branched Cs-do-alkyl, in particular ethyl, 3,5,5-trimethylhexyl, n-heptyl, n-octyl, n-nonyl or n-decyl.
A further embodiment relates to compounds IV in which E1 is phenyl which is unsubsti- tuted or substituted by one to four radicals Rb.
Preferred compounds IV are those in which E1 is a substituted phenyl group which corresponds to a group Ar
Figure imgf000013_0001
in which
L1 to L3 are halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, Ci-Cβ- haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-Cβ-alkoxy; r and q independently of one another may be 0 or 1 sein, where NRARB is as defined in formula IV and # denotes the bond to the azolopyrimidine skeleton.
In a further embodiment of the compounds IV, L1 is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, d-Cε-alkyl, halomethyl and Ci-C2-alkoxy, preferably halogen, cyano, d-Cε-alkyl, halomethyl or Ci-C2-alkoxy.
In a further embodiment of the compounds IV, q is 0 or L2 is one of the groups mentioned above and q is 1.
In a further embodiment of the compounds IV, r is 0 or L3 is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, d-Cε-alkyl, halomethyl or Ci-C2-alkoxy and r is 1. Preferably, r is zero.
Preference is given to compounds IV in which E2 is straight-chain or branched C1-C12- alkyl, Ci-C4-alkoxy-Ci-C4-alkyl or Ci-C4-haloalkyl.
In a particularly preferred embodiment of the compounds IV, E2 is methyl, ethyl, n- propyl, n-octyl, trifluoromethyl or methoxymethyl, in particular methyl, ethyl, trifluoro- methyl or methoxymethyl. Preference is furthermore given to compounds IV in which E3 is hydrogen.
In a further embodiment of the compounds IV, E3 is amino. One embodiment of the compounds IV relates to those in which A is N. These compounds correspond to formula IVa in which the variables are as defined for formula IV:
Figure imgf000014_0001
Another embodiment of the compounds of the formula IV relates to those in which A is CH. These compounds correspond to formula IVb in which the variables are as defined for formula IV:
Figure imgf000014_0002
In a further embodiment of preferred compounds IV, the sum of the carbon atoms in the carbon radicals of E1 and E2 is not more than 12.
Very particularly preferred azolopyrimidin-7-ylamines IV are those listed in Table 1 :
Table 1
Figure imgf000014_0003
Preference is furthermore also given to compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of E) carbamates.
Preference is furthermore also given to compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungicides.
Preference is also given to compositions of a component 1 ) with a component 2) consisting of at least one active compound (II) selected from the group of F) other fungi- cides selected from the group consisting of metrafenone, dodine free base, guazatine- acetate, iminoctadine-triacetate, iminoctadine-tris(albesilate), kasugamycin- hydrochlorid-hydrat, dichlorophen, pentachlorophenol and its salts, N-(4-chloro-2-nitro- phenyl)-N-ethyl-4-methyl-benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, biphenyl, bronopol, diphenylamine, mildiomycin, oxin-copper and prohexadione cal- cium, in particular metrafenone, dodine free base, guazatine-acetate, iminoctadine- triacetate, iminoctadine-tris(albesilate), nitrothal-isopropyl, mildiomycin, oxin-copper and prohexadione calcium. Very particularly preferred is metrafenone.
Particular preference is given to compositions of a compound 1 ) with a component 2) consisting of at least one active compound (II) selected from groups C), D) and F), whereas each of C), D) and F) may consist of all members or the preferred embodiments.
Preference is also given to three-component compositions comprising a component 1 ), wherein component 2) consists of two of the active compounds (II) mentioned above.
Preference is also given to three-component compositions comprising, in addition to component 1) and component 2) consisting of one active compound (II) mentioned above, a further fungicidally active compound V selected from active compound groups G) to M):
G) azoles selected from the group consisting of bitertanol, bromuconazole, cypro- conazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquin- conazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothiocon- azole, simeconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triti- conazole, prochloraz, pefurazoate, imazalil, triflumizole, cyazofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, etridiazole and hymexa- zole;
H) strobilurins selected from the group consisting of azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, methyl (2-chloro-5-[1-(3- methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1 -(6-methyl- pyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate and methyl 2-(ortho-(2,5-di- methylphenyloxymethylene)phenyl)-3-methoxyacrylate; J) carboxamides selected from the group consisting of carboxin, boscalid, fen- hexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, thifluzamide, tiadinil, 3,4-dichloro-N-(2-cyanophenyl)iso-thiazole-5- carboxamide, penthiopyrad, dimethomorph, flumorph, flumetover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid,
N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-ethoxyphenyl)ethyl)-2-methane- sulfonylamino-3-methylbutyramide, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3- methoxyphenyl)ethyl)-2-ethanesulfonylamino-3-methylbutyramide, methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)- propionate, N-(4' -bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5- carbox-amide, N-(4' -trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2- methylthiazole-5-carboxamide, N-(4' -chloro-3' -fluorobiphenyl-2-yl)-4- difluoromethyl-2-methyl-thiazole-5-carboxamide, N-(3' ,4' -dichloro-4- fluorobiphenyl-2-yl)-3-difluoromethyl-1 -methylpyrazole-4-carboxamide and N-(2- cyanopheny^-S^-dichloroisothiazole-δ-carboxamide;
K) heterocyclic compounds selected from the group consisting of fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuarimol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropi- morph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6- trifluorophenyl)-[1 ,2,4]triazolo[1 ,5-a]pyrimidine, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4-one, acibenzolar-S- methyl, captafol, captan, dazomet, folpet, fenoxanil, quinoxyfen and N,N-dimethyl- 3-(3-bromo-6-fluoro-2-methylindole-1 -sulfonyl)-[1 ,2,4]triazole-1 -sulfonamide;
L) carbamates selected from the group consisting of mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flub- enthiavalicarb, propamocarb, 4-fluorophenyl N-(1-(1-(4-cyanophenyl)ethane- sulfonyl)but-2-yl)carbamate, methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonyl- amino-3-methylbutyrylamino)propanoate and carbamate oxime ethers of the formula Vl
Figure imgf000016_0001
in which Z is N or CH;
M) other fungicides selected from the group consisting of guanidine, dodine, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane, organometallic compounds: fentin salts such as fentin acetate, organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos-methyl, organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlor- benzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, inorganic active compounds: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl and spiroxamine.
The active compounds V mentioned above, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.
Preference is given to three-component compositions of components 1 ) and 2) with an active compound V selected from the group of the azoles G).
Preference is also given to three-component compositions of components 1 ) and 2) with an active compound V selected from the group of the strobilurins H).
Preference is given to three-component compositions of components 1 ) and 2) with an active compound V selected from the group of the carboxamides J).
Preference is furthermore also given to three-component compositions of components 1 ) and 2) with an active compound V selected from the group of the heterocyclic compounds K).
Preference is furthermore also given to three-component compositions of components 1 ) and 2) with an active compound V selected from the group of the carbamates L).
Preference is furthermore also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the other fungicides M).
Preference is furthermore also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl, carbendazim and ethaboxam. Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, metconazole, myclobutanil, propiconazole, prothioconazole, triadimefon, triadimenol, tebuconazole, tetraconazole, triticonazole, prochloraz, cyazofamid, benomyl and carbendazim.
Very particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the azoles G) selected from the group consisting of epoxiconazole, fluquinconazole, flutriafol, metconazole, tebuconazole, triticonazole, prochloraz and carbendazim.
Preference is also given to three-component compositions of components 1 ) and 2) with at least one active compound selected from the group of the strobilurins H) selected from the group consisting of azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, orysastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin.
Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the strobilurins H) selected from the group consisting of kresoxim-methyl, orysastrobin and pyraclostrobin.
Very particular preference is also given to three-component compositions of components 1 ) and 2) with pyraclostrobin.
Preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the carboxamides J) selected from the group consisting of fenhexamid, mefenoxam, ofurace, dimethomorph, flumorph, fluopicolide (picobenzamid), zoxamide, carpropamid and mandipropamid.
Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the carboxamides J) selected from the group consisting of fenhexamid, metalaxyl, mefenoxam, ofurace, dimethomorph, zoxamide and carpropamid.
Preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the heterocyclic compounds J) selected from the group consisting of fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforine, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen, in particular fluazinam, cyprodinil, fenarimol, mepanipyrim, pyrimethanil, triforine, fludioxonil, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, vinclozolin, famoxadone, fenamidone, probenazole, proquinazid, acibenzolar-S-methyl, captafol, folpet, fenoxanil and quinoxyfen.
Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the heterocyclic compounds K) selected from the group consisting of pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozolin and quinoxyfen, in particular pyrimethanil, dodemorph, fenpropimorph, tridemorph, iprodione, vinclozolin and quinoxyfen.
Preference is also given to three-component compositions of components 1 ) and 2) with at least one active compound selected from the group of the carbamates L) selected from the group consisting of mancozeb, metiram, propineb, thiram, iprovalicarb, flubenthiavalicarb and propamocarb.
Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the carbamates L) selected from the group consisting of mancozeb and metiram.
Preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the other fungicides M) selected from the group consisting of dithianon, fentin salts, such as fentin acetate, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, chlorothalonil, dichlofluanid, thiophanate-methyl, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, cymoxanil and spiroxamine.
Particular preference is also given to three-component compositions of components 1 ) and 2) with an active compound selected from the group of the other fungicides M) selected from the group consisting of phosphorous acid and its salts and chlorothalonil.
Preference is also given to four-component compositions of components 1 ) and 2) with two futher active compounds selected from compounds Il and V mentioned above.
Preferred active compound combinations are listed in tables 2 to 7 below:
Table 2
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group A):
Figure imgf000019_0001
Mixture Component 1 ) Component 2)
No. A.2 SERENADE® MAX azaconazole
No. A.3 SERENADE® ASO azaconazole
No. A.4 SONATA® azaconazole
No. A.5 BALLAD® Plus azaconazole
No. A 6 RHAPSODY® diniconazole-M
No. A 7 SERENADE® MAX diniconazole-M
No. A 8 SERENADE® ASO diniconazole-M
No. A 9 SONATA® diniconazole-M
No. A 10 BALLAD® Plus diniconazole-M
No. A 11 RHAPSODY® oxpoconazol
No. A 12 SERENADE® MAX oxpoconazol
No. A 13 SERENADE® ASO oxpoconazol
No. A 14 SONATA® oxpoconazol
No. A 15 BALLAD® Plus oxpoconazol
No. A 16 RHAPSODY® paclobutrazol
No. A 17 SERENADE® MAX paclobutrazol
No. A 18 SERENADE® ASO paclobutrazol
No. A 19 SONATA® paclobutrazol
No. A 20 BALLAD® Plus paclobutrazol
No. A 21 RHAPSODY® uniconazol
No. A 22 SERENADE® MAX uniconazol
No. A 23 SERENADE® ASO uniconazol
No. A 24 SONATA® uniconazol
No. A 25 BALLAD® Plus uniconazol
No. A 26 RHAPSODY® 1 -(4-chloro-phenyl)-2-([1 ,4]triazol-1-yl)- cycloheptanol
No. A 27 SERENADE® MAX 1 -(4-chloro-phenyl)-2-([1 ,2 ,4]triazol-1-yl)- cycloheptanol
No. A 28 SERENADE® ASO 1 -(4-chloro-phenyl)-2-([1 ,4]triazol-1-yl)- cycloheptanol
No. A 29 SONATA® 1 -(4-chloro-phenyl)-2-([1 ,4]triazol-1-yl)- cycloheptanol
No. A 30 BALLAD® Plus 1 -(4-chloro-phenyl)-2-([1 ,2 ,4]triazol-1-yl)- cycloheptanol
No. A.31 RHAPSODY® imazalil-sulfphate
No. A 32 SERENADE® MAX imazalil-sulfphate
No. A 33 SERENADE® ASO imazalil-sulfphate
No. A.34 SONATA® imazalil-sulfphate
Figure imgf000021_0001
Table 3
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group B):
Figure imgf000021_0002
Table 4
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group C):
Figure imgf000021_0003
Figure imgf000022_0001
Figure imgf000023_0001
Figure imgf000024_0001
Figure imgf000025_0001
Mixture Component 1 ) Component 2)
No. C. 100 BALLAD® Plus N-(2',4',5'-trifluorobiphenyl-2-yl)-1-methyl-3- difluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 101 RHAPSODY® N-(3\4\5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 102 SERENADE® MAX N-(3\4\5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 103 SERENADE® ASO N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 104 SONATA® N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 105 BALLAD® Plus N-(3',4',5'-trifluorobiphenyl-2-yl)-3-chlorofluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 106 RHAPSODY® N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 107 SERENADE® MAX N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 108 SERENADE® ASO N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 109 SONATA® N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 110 BALLAD® Plus N-(4'-trifluoromethylthio-biphenyl-2-yl)-3-difluoro- methyl-1 -methyl-1 H-pyrazole-4-carboxamide
No. C. 11 1 RHAPSODY® N-(4'-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 112 SERENADE® MAX N-(4'-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 113 SERENADE® ASO N-(4'-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 1 14 SONATA® N-(4'-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 115 BALLAD® Plus N-(4'-trifluoromethylthio-biphenyl-2-yl)-1-methyl- 3-trfluoromethyl-1 H-pyrazole-4-carboxamide
No. C. 1 16 RHAPSODY® isopyrazam
No. C. 1 17 SERENADE® MAX isopyrazam
No. C. 118 SERENADE® ASO isopyrazam
No. C. 1 19 SONATA® isopyrazam
No. C. 120 BALLAD® Plus isopyrazam Table 5
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group D):
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Table 6
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group E):
Figure imgf000032_0002
Figure imgf000033_0001
Table 7
Active compound combinations of a component 1) and a component 2), conprising a compound Il selected from group F):
Figure imgf000033_0002
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000036_0001
The compositions comprising the components 1 ) and 2), or the simultaneous, that is joint or separate, use of a component 1) and a component 2), are distinguished by excellent activity against a broad spectrum of phytopathogenic fungi in particular from the classes of the Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomy- cetes (syn. Oomycetes). Some of them are systemically active and can be used in crop protection as foliar fungicides, as soil fungicides and as fungicides for seed dressing.
The compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; beet, for example sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; laura- ceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, for example conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, compounds I and compositions thereof are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be mentioned. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with compounds I and composi- tions thereof is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans. The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
The term "cultivated plants" is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy- phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e. g. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e. g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e. g. EP-A-0242236, EP-A-242246) or oxynil herbi- cides (see e. g. US 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e. g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ -endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bi ) or Cryθc; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal pro- teins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
Genetically modified plants capable to synthesize one or more insecticidal proteins are, for example, described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CryiAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CryiAc toxin), Bollgard® I (cotton culti- vars producing the CryiAc toxin), Bollgard® Il (cotton cultivars producing CryiAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CryiAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called " pathogenesis-related proteins" (PR proteins, see, for example EP-A 0 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solarium bulbocastanum) or T4-lyso- zym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
The term "cultivated plants" is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil con- tent or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape).
The term "cultivated plants" is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato).
The term "protein" as used herein is to be understood as an oligopeptide or polypeptide or molecule made up of polypeptides including expressly also pre-proteins, hybrid proteins, peptides, truncated or otherwise modified proteins including those derived from post-transcriptional modifications such as acylation (e.g. acetylation, the addition of an acetyl group, usually at the N-terminus of the protein), alkylation, the addition of an alkyl group (e.g. addition of ethyl or methyl, usually at lysine or arginine residues) or demethylation, amidation at C-terminus, biotinylation (acylation of conserved lysine residues with a biotin appendage), formylation, y -carboxylation dependent on Vitamin K, glutamylation (covalent linkage of glutamic acid residues), glycosylation (addition of a glycosyl group to either asparagine, hydroxylysine, serine, or threonine, resulting in a glycoprotein), glycation (nonenzymatic attachment of sugars), glycylation (covalent linkage of one to more glycine residues), covalent attachment of a heme moiety, hydro- xylation, iodination, isoprenylation (addition of an isoprenoid group such as farnesol and geranylgeraniol), lipoylation (attachment of a lipoate functionality) including prenyl- ation, GPI anchor formation (e. g. myristoylation, farnesylation and geranylgeranyl- ation), covalent attachment of nucleotides or derivatives thereof including ADP-ribosyl- ation and flavin attachment, oxidation, pegylation, covalent attachment of phosphatidyl- inositol, phosphopantetheinylation (addition of a 4'-phosphopantetheinyl moiety from coenzyme A), phosphorylation (addition of a phosphate group, usually to serine, tyrosine, threonine or histidine), pyroglutamate formation, racemization of proline, tRNA- mediated addition of amino acids such as arginylation, sulfation (addition of a sulfate group to a tyrosine), selenoylation (co-translational incorporation of selenium in selenoproteins), ISGylation (covalent linkage to the ISG15 protein [Interferon- stimulated Gene 15]), SUMOylation (covalent linkage to the SUMO protein [Small Ubiquitin-related Modifier]), ubiquitination (covalent linkage to the protein ubiquitin or poly-ubiquitin), citrullination or deimination (conversion of arginine to citrulline), deamidation (conversion of glutamine to glutamic acid or asparagine to aspartic acid), formation of disulfide bridges (covalent linkage of two cysteine amino acids) or proteolytic cleavage (cleavage of a protein at a peptide bond).
The plants or seed treated with the combinations comprising components 1 ) and 2) may by wildlife types, plants or seed obtained by breeding and transgenic plants as well as their seed.
They are especially suitable for controlling the following phytopathogenic fungi:
Alternaria atrans tenuissima Diaporthe phaseolorum var. caulivora
Alternaria brassicae Drechslera glycini
Alternaria spp. Epicoccum spp.
Ascochyta tritici Erwinia amylovora
Blumeria graminis Erysiphe graminis
Botrytis cinerea Frogeye sojina
Bremia lactucae Fusarium solani
Bremia lucinae Fusarium culmorum
Calonectria crotalariae Fusarium graminearum
Cercospora canescens Gaeumannomyces graminis
Cercospora kikuchii Leptosphaeria nodorum
Cercospora sojina Leptosphaerulina trifolii
Cercospora canescens Macrophomina phaseolina
Choanephora infundibulifera Microdochium nivale
Cladosporium herbarum Microsphaera diffusa
Cochliobolus sativus Mycoleptodiscus terrestris
Cochliobolus sativus Neocosmospora vasinfecta
Colletotrichum truncatum Pellicularia sasakii
Corynespora cassiicola Peronospora brassicae
Dactuliophora glycines Peronospora manshurica
Dematophora necatrix Peronospora brassicae
Diaporthe phaseolorum Peronospora pisi Phakopsora pachyrhizi Pyrenophora convohuli
Phakopsora meibomiae Pyrenophora coppeyana
Phialophora gregata Pyrenophora cytisi
Phomopsis phaseoli Pyrenophora dactylidis
Phyllostica sojaecola Pyrenophora dictyoides
Physiological leaf spots Pyrenophora echinopis
Phythium ultimum Pyrenophora ephemera
Phytophthora megasperma Pyrenophora eryngicola
Phytophthora infestans Pyrenophora erythrospila
Phytopthora megasperma Pyrenophora euphorbiae
Plasmopara viticola Pyrenophora freticola
Podosphaera leucotricha Pyrenophora graminea
Podosphaera leucotricha Pyrenophora graminea
Pseudocercospora herpotrichoides Pyrenophora heraclei
Pseudomonas lachrymans Pyrenophora hordei
Pseudomonas syringae Pyrenophora horrida
Pseudoperonospora cubensis Pyrenophora hyperici
Pseudoperonospora humuli Pyrenophora japonica
Puccinia hordei Pyrenophora kugitangi
Puccinia recondita Pyrenophora lithophila
Puccinia striiformis Pyrenophora lolii
Puccinia triticina Pyrenophora macrospora
Pyrenochaeta glycines Pyrenophora metasequoiae
Pyrenophora allosuri Pyrenophora minuertiae hirsutae
Pyrenophora altermarina Pyrenophora moravica
Pyrenophora avenae Pyrenophora moroczkowskii
Pyrenophora bartramiae Pyrenophora muscorum
Pyrenophora bondarzevii Pyrenophora osmanthi
Pyrenophora bromi Pyrenophora phlei
Pyrenophora bryophila Pyrenophora pimpinellae
Pyrenophora buddleiae Pyrenophora pittospori
Pyrenophora bupleuri Pyrenophora polytrichia
Pyrenophora calvertii Pyrenophora pontresinerisis
Pyrenophora calvescens var. moravica Pyrenophora pulsatillae
Pyrenophora carthanie Pyrenophora raetica
Pyrenophora centranthi Pyrenophora rayssiae
Pyrenophora cerastii Pyrenophora rugosa
Pyrenophora chengii Pyrenophora ryohicola
Pyrenophora chrysamthemi Pyrenophora saviczii Pyrenophora schoeteri Rhizoctonia anomala Pyrenophora scholevskii Rhizoctonia apocynacearum Pyrenophora scirpi Rhizoctonia arachnion Pyrenophora scirpicola Rhizoctonia asclerotica Pyrenophora secalis Rhizoctonia batalicola Pyrenophora semeniperda Rhizoctonia borealis Pyrenophora semiusta Rhizoctonia callae Pyrenophora seseli Rhizoctonia carorae Pyrenophora seseli f. poterii Rhizoctonia cerealis Pyrenophora subalpina Rhizoctonia choussii Pyrenophora sudetica Rhizoctonia coniothecioides Pyrenophora suhantarctica Rhizoctonia cundida Pyrenophora syntrichiae Rhizoctonia dichoroma Pyrenophora szaferiana Rhizoctonia dimorpha Pyrenophora teres Rhizoctonia endophytica Pyrenophora teres f. makulata Rhizoctonia endophytica vor. filicata Pyrenophora teres subsp. graminea Rhizoctonia ferruginea Pyrenophora tetrahenae Rhizoctonia floccosa Pyrenophora tranzschelii Rhizoctonia fragariae Pyrenophora trifulii Rhizoctonia fraxini Pyrenophora triticil-repentis Rhizoctonia fuliginea Pyrenophora ushuwaiensis Rhizoctonia fumigata Pyrenophora villose Rhizoctonia globularis Pyrenophora graminea Rhizoctonia goodyerae-repentis Pyrenophora teres Rhizoctonia gossypii Pyrenophora teres Rhizoctonia gossypii vor. anatolica Pyrenophora teres Rhizoctonia gracilis Pyrenophora tritici repentis Rhizoctonia griseo Pyricularia oryzae Rhizoctonia hiemalis Pythium aphanidermatum Rhizoctonia juniperi Pythium debaryanum Rhizoctonia lamallifera Pythium irregulare Rhizoctonia leguminicola Pythium myriotylum Rhizoctonia lilacina Pythium ultimum Rhizoctonia luoini Ramularia collocygni Rhizoctonia macrosclerotia Rhizoctonia aerea Rhizoctonia melongenae Rhizoctonia alba Rhizoctonia microsclerotia Rhizoctonia alpina Rhizoctonia monilioides Rhizoctonia anaticula Rhizoctonia monteithiana Rhizoctonia muneratii Tilletia aegopogonis
Rhizoctonia nandorii Tilletia ahamadiana
Rhizoctonia oryzae Tilletia airina
Rhizoctonia oryzae-sativae Tilletia ajrekari
Rhizoctonia pallida Tilletia alopecuri
Rhizoctonia pini-insignis Tilletia anthaxanthi
Rhizoctonia praticola Tilletia apludae
Rhizoctonia quercus Tilletia armdinellae
Rhizoctonia ramicola Tilletia asperifolia
Rhizoctonia robusta Tilletia asperitolioides
Rhizoctonia rubi Tilletia atacamensis
Rhizoctonia ruhiginosa Tilletia baldrati
Rhizoctonia sclerotica Tilletia bambusae
Rhizoctonia solani Tilletia banarasae
Rhizoctonia solani f. paroketea Tilletia bangalorensis
Rhizoctonia solani forma specialis Tilletia barclayana
Rhizoctonia solani var. cedri-deodorae Tilletia biharica
Rhizoctonia solani var. fuchsiae Tilletia boliviensis
Rhizoctonia solani var. hortensis Tilletia boutelouae
Rhizoctonia stahlii Tilletia brachypodii
Rhizoctonia subtilis var. nigra Tilletia brachypodii-ramosi
Rhizoctonia subtlilis Tilletia braomi-tectorum
Rhizoctonia tomato Tilletia brevifaciens
Rhizoctonia tuliparum Tilletia bromi
Rhizoctonia veae Tilletia bromina
Rhizoctonia versicolor Tilletia brunkii
Rhizoctonia cerealis Tilletia buchloeana
Rhynchosporium secalis Tilletia bulayi
Sclerotina rolfsii Tilletia caries
Sclerotinia rolfsii Tilletia cathcariae
Sclerotinia sclerotiorum Tilletia cerebrina
Septoria glycines Tilletia chloridicola
Septoria nodorum Tilletia contaoversa
Septoria tritici Tilletia contraversa var. prostrata
Sphaerotheca fuliginea Tilletia contraversa var. elyni
Stagonospora nodorum Tilletia corona
Stemphylium botryosum Tilletia cynasuri
Thielaviopsis basicola Tilletia damacarae
Tilletia aegilopis Tilletia deyeuxiae Tilletia digitariicola Tilletia laguri
Tilletia durangensis Tilletia leptochlase
Tilletia earlei Tilletia lepturi
Tilletia echinochlave Tilletia macrotuberculata
Tilletia echinochloae Tilletia madeirensis
Tilletia echinosperma Tilletia maglagonii
Tilletia ehrhartae Tilletia makutensis
Tilletia eleusines Tilletia milti
Tilletia elymandrae Tilletia milti-vernalis
Tilletia elymicola Tilletia montana
Tilletia elyni Tilletia montemartinii
Tilletia elythrophori Tilletia nanifica
Tilletia eragrostidis Tilletia narasimhanii
Tilletia euphorbiae Tilletia narayanaoana
Tilletia fahrendorfii Tilletia narduri
Tilletia festinca-octoflorana Tilletia nigrifaciens
Tilletia foelida Tilletia obscura-reticulora
Tilletia foliicola Tilletia oklahomae
Tilletia fusca Tilletia okudoirae
Tilletia fusca var. bromi-tectorum Tilletia oplistneni-cristati
Tilletia fusca var. guyotiana Tilletia paae
Tilletia fusca var.paragonica Tilletia pachyderma
Tilletia georfischeri Tilletia pallida
Tilletia gigaspora Tilletia panici
Tilletia goloskokovii Tilletia panici. humilis
Tilletia haynaldiae Tilletia paonensis
Tilletia heterospora Tilletia paraloxa
Tilletia holci Tilletia paspali
Tilletia hordei var.spontanei Tilletia pennisetina
Tilletia horrida Tilletia peritidis
Tilletia hyalospora var.cuzcoensis Tilletia phalaridis
Tilletia hyparrheniae Tilletia polypoganis
Tilletia indica Tilletia prostrata
Tilletia iniermedia Tilletia pulcherrima var. brachiariae
Tilletia iovensis Tilletia redfieldiae
Tilletia ixophari Tilletia rhei
Tilletia koeleriae Tilletia rugispora
Tilletia kuznetzoviana Tilletia sabaudiae
Tilletia laevis Tilletia salzmanii Tilletia savilei Ustilago agrostis-palustris
Tilletia scrobiculata Ustilago airear-caespitosae
Tilletia setariae Ustilago alismatis
Tilletia setariae-palmiflorarae Ustilago almadina
Tilletia setariicola Ustilago alopecurivara
Tilletia sphaerococca Ustilago alsineae
Tilletia sphenopie Ustilago altilis
Tilletia sphenopodis Ustilago amadelpha var. glabriuscula
Tilletia sterilis Ustilago amphilophidis
Tilletia taiana Ustilago amplexa
Tilletia texana Ustilago amthoxanthi
Tilletia themedae-anatherae Ustilago andropogonis-tectorum
Tilletia themedicola Ustilago aneilemae
Tilletia toguateei Ustilago anhweiona
Tilletia trachypogonis Ustilago anomala var. avicularis
Tilletia transiliensis Ustilago anomala var. carnea
Tilletia transvaalensis Ustilago anomala var. cordai
Tilletia tritici f. monococci Ustilago anomala var. microspora
Tilletia tritici var. controversa Ustilago anomala var. muricata
Tilletia tritici var. nanifica Ustilago anomala var. tovarae
Tilletia tritici var. laevis Ustilago apscheronica
Tilletia tritici-repentis Ustilago arabidia.alpinae
Tilletia triticoides Ustilago arandinellae-hirtae
Tilletia tuberculare Ustilago arctica
Tilletia vertiveriae Ustilago argentina
Tilletia viermotii Ustilago aristidarius
Tilletia vittara Ustilago arotragostis
Tilletia vittara var. burmahnii Ustilago asparagi-pygmaei
Tilletia walkeri Ustilago asprellae
Tilletia youngii Ustilago avanae subsp. alba
Tilletia zundelii Ustilago avenae
Typhula incarnata Ustilago avenae
Uromyces appendiculatus Ustilago avenae f. sp. perennars
Ustilago aaeluropodis Ustilago avenariae-bryophyllae
Ustilago abstrusa Ustilago avicularis
Ustilago aegilopsidis Ustilago bahuichivoensis
Ustilago affinis var. hilariae Ustilago barbari
Ustilago agrestis Ustilago beckeropsis
Ustilago agropyrina Ustilago belgiana Ustilago bethelii Ustilago clelandii
Ustilago bicolor Ustilago clintoniana
Ustilago bistortarum ustiloginea Ustilago coloradensis
Ustilago bistortarum var. pustulata Ustilago commelinae
Ustilago boreatis Ustilago compacta
Ustilago bothriochloae Ustilago concelata
Ustilago bothriochloae-intermediae Ustilago condigna
Ustilago bouriqueti Ustilago consimilis
Ustilago braziliensis Ustilago constantineanui
Ustilago brisae Ustilago controversa
Ustilago bromi-arvensis Ustilago conventere-sexualis
Ustilago bromi-erecti Ustilago cordai
Ustilago bromi-mallis Ustilago corlarderiae var. araucana
Ustilago bromina Ustilago coronariaw
Ustilago bromivora f. brachypodii Ustilago coronata
Ustilago bromivora var. microspora Ustilago courtoisii
Ustilago bullata f. brachypodii-distachyi Ustilago crus-galli var. minor
Ustilago bullata var. bonariesis Ustilago cryptica
Ustilago bullata var. macrospora Ustilago curta
Ustilago bungeana Ustilago custanaica
Ustilago calanagrostidis Ustilago cynodontis
Ustilago calanagrostidis var. scrobiculata Ustilago cynodontis
Ustilago calanagrostidis var. typica Ustilago cyperi-lucidi
Ustilago cardamines Ustilago davisii
Ustilago cariciphila Ustilago deccanii
Ustilago caricis-wallichianae Ustilago decipiens
Ustilago carnea Ustilago deformitis
Ustilago catherimae Ustilago dehiscens
Ustilago caulicola Ustilago delicata
Ustilago cenrtodomis Ustilago deyeuxiae
Ustilago ceparum Ustilago dianthorum
Ustilago cephalariae Ustilago distichlidis
Ustilago chacoensis Ustilago dubiosa
Ustilago chloridii Ustilago dumosa
Ustilago chloridionis Ustilago earlei
Ustilago chrysopoganis Ustilago echinochloae
Ustilago chubulensis Ustilago ehrhartana
Ustilago cichorii Ustilago eleocharidis
Ustilago cilmodis Ustilago eleusines Ustilago elymicola Ustilago hilariicola
Ustilago elytrigiae Ustilago hilubii
Ustilago enneapogonis Ustilago himalensis
Ustilago epicampida Ustilago histortarum var. marginalis
Ustilago eragrostidis-japanicana Ustilago hitchcockiana
Ustilago eriocauli Ustilago holci-avanacei
Ustilago eriochloae Ustilago hordei
Ustilago euphorbiae Ustilago hordei f. sp. avenae
Ustilago fagopyri Ustilago hsuii
Ustilago festucae Ustilago hyalino-bipolaris
Ustilago festucorum Ustilago hydropiperis
Ustilago filamenticola Ustilago hyparrheniae
Ustilago fingerhuthiae Ustilago hypodyies f. congoensis
Ustilago flectens Ustilago hypodytes f. sporaboli
Ustilago flonersii Ustilago hypodytes var. agrestis
Ustilago foliorum Ustilago idonea
Ustilago formosana Ustilago imperatue
Ustilago fueguina Ustilago induia
Ustilago gageae Ustilago inouyei
Ustilago garcesi Ustilago intercedens
Ustilago gardneri Ustilago iranica
Ustilago gausenii Ustilago isachnes
Ustilago gayazana Ustilago ischaemi-akoensis
Ustilago gigantispora Ustilago ischaemi-anthephoroides
Ustilago glyceriae Ustilago ixiolirii
Ustilago gregaria Ustilago ixophori
Ustilago grossheimii Ustilago jacksonii
Ustilago gunnerae Ustilago jacksonii var. vintonesis
Ustilago haesendocki var. chloraphorae Ustilago jaczevskyana
Ustilago haesendocki var. vargasii Ustilago jaczevskyana van. typica
Ustilago halophiloides Ustilago jaczevskyana var. sibirica
Ustilago haynalodiae Ustilago jagdishwari
Ustilago heleochloae Ustilago jamalainentii
Ustilago helictotrichi Ustilago jehudana
Ustilago herteri var. Bicolor Ustilago johnstonii
Ustilago herteri var. vargasii Ustilago kairamoi
Ustilago hierochloae-adoratae Ustilago kasuchstemica
Ustilago hieronymi var. insularis Ustilago kenjiana
Ustilago hieronymi var. minor Ustilago kweichowensis Ustilago kylingae Ustilago mrucata
Ustilago lacjrymae-jobi Ustilago muda
Ustilago lepyrodiclidis Ustilago muehlenbergiae var. lucumanensis
Ustilago lidii Ustilago muscaribotryoidis
Ustilago liebenbergii Ustilago nagarnyi
Ustilago linderi Ustilago nannfeldtii
Ustilago linearis Ustilago nauda var. hordei
Ustilago lirove Ustilago nelsoniana
Ustilago loliicola Ustilago nepalensis
Ustilago longiflora Ustilago neyraudiae
Ustilago longiseti Ustilago nigra
Ustilago longissima var. dubiosa Ustilago nivalis
Ustilago longissima var. paludificans Ustilago nuda
Ustilago longissima var. typica Ustilago nuda
Ustilago lupini Ustilago nuda var.tritici
Ustilago lychnidis-dioicae Ustilago nyassae
Ustilago lycoperdiformis Ustilago okudairae
Ustilago lyginiae Ustilago olida
Ustilago machili Ustilago olivacea var. macrospora
Ustilago machringiae Ustilago onopordi
Ustilago magalaspora Ustilago onumae
Ustilago magellanica Ustilago opiziicola
Ustilago mariscana Ustilago oplismeni
Ustilago maydis Ustilago orientalis
Ustilago melicae Ustilago otophora
Ustilago merxmuellerana Ustilago ovariicola
Ustilago mesatlantica Ustilago overcemii
Ustilago michnoana Ustilago pamirica
Ustilago microspora Ustilago panici-geminati
Ustilago microspora var. paspalicola Ustilago panjabensis
Ustilago microstegii Ustilago pappophori
Ustilago microthelis Ustilago pappophori var. magdalensis
Ustilago milli Ustilago parasnothii
Ustilago mobtagnei var. minor Ustilago parodii
Ustilago modesta Ustilago parvula
Ustilago moenchiae-manticae Ustilago paspalidiicola
Ustilago monermae Ustilago patagonica
Ustilago morinae Ustilago penniseti var. verruculosa
Ustilago morobiana Ustilago perrara Ustilago persicariae Ustilago scitaminea
Ustilago petrakii Ustilago scitaminea var. sacchar-officinorum
Ustilago phalaridis Ustilago scleranthi
Ustilago phlei Ustilago scrobiculata
Ustilago phlei-protensis Ustilago scutulata
Ustilago phragmites Ustilago secalis var. elymi
Ustilago picacea Ustilago seitaminea var. sacchari-barberi
Ustilago pimprina Ustilago semenoviana
Ustilago piperi (var.) rosulata Ustilago serena
Ustilago poae Ustilago serpens
Ustilago poae-bulbosae Ustilago sesleriae
Ustilago poae-nemoralis Ustilago setariae-mambassanae
Ustilago polygoni-alati Ustilago shastensis
Ustilago polygoni-alpini Ustilago shimadae
Ustilago polygoni-punctari Ustilago silenes-inflatae
Ustilago polygoni-serrulati Ustilago silenes-nutantis
Ustilago polytocae Ustilago sinkiangensis
Ustilago polytocae-harbatas Ustilago sitanil
Ustilago pospelovii Ustilago sleuneri
Ustilago prostrata Ustilago sonoriana
Ustilago pseudohieronymi Ustilago sorghi-stipoidei
Ustilago puehlaensis Ustilago spadicea
Ustilago puellaris Ustilago sparoboli-indici
Ustilago pulvertulensa Ustilago sparti
Ustilago raciborskiana Ustilago speculariae
Ustilago radians Ustilago spegazzinii
Ustilago ravida Ustilago spegazzinii var. agrestis
Ustilago rechingeri Ustilago spermophora var. orientalis
Ustilago reticulara Ustilago spermophoroides
Ustilago reticulispora Ustilago spinulosa
Ustilago rhei Ustilago sporoboli-trenuli
Ustilago rhynchelytri Ustilago stellariae
Ustilago ruandenis Ustilago sterilis
Ustilago ruberculata Ustilago stewartli
Ustilago sabouriana Ustilago stipae
Ustilago salviae Ustilago striaeformis f. phlei
Ustilago sanctae-catharinae Ustilago striaeformis f. poa...
Ustilago scaura Ustilago striaeformis f. poae-pratensis
Ustilago scillae Ustilago striiformis f. hierochloes-odoratae Ustilago striiformis var. agrostidis Ustilago tucumariensis
Ustilago striiformis var. dactylidis Ustilago tumeformis
Ustilago striiformis var. holci Ustilago turcomanica
Ustilago striiformis var. phlei Ustilago turcomanica var. prostrata
Ustilago striiformis var. poae Ustilago turcomanica var. typica
Ustilago sumnevicziana Ustilago ugamica
Ustilago superha Ustilago ugandensis var. macrospora
Ustilago sydowiana Ustilago underwoodii
Ustilago symbiotica Ustilago urginede
Ustilago taenia Ustilago urochloana
Ustilago taiana Ustilago ustilaginea
Ustilago tanakue Ustilago ustriculosa var. cordai
Ustilago tenuispora Ustilago ustriculosa var. reticulata
Ustilago thaxteri Ustilago valentula
Ustilago tinontiae Ustilago vavilori
Ustilago togata Ustilago verecunda
Ustilago tournenxii Ustilago verruculosa
Ustilago tovarae Ustilago versatilis
Ustilago trachophora var. pacifica Ustilago vetiveriae
Ustilago trachyniae Ustilago violaceo-irregularis
Ustilago trachypogonis Ustilago violaceu var. stellariae
Ustilago tragana Ustilago violaceuverrucosa
Ustilago tragi Ustilago williamsii
Ustilago tragica Ustilago wynaadensis
Ustilago tragi-racemosi Ustilago zambettakisii
Ustilago trichoneurana Ustilago zernae
Ustilago trichophora var. crus-galli Venturia inaequalis
Ustilago trichophora var. panici-frumentacei Xanthomonas campestris
Ustilago triseti Xanthomonas oryzae
Ustilago tritici forma specialis
The compositions comprising the components 1 ) and 2) are particularly suitable for controlling phytopathogenic fungi in barley (e.g. Pyrenophora teres, Rhynchosporium secalis,Puccinia hordei,Puccinia striiformis, Blumeria graminis, Ramularia collo-cygni / Physiological leaf spots, Microdochium nivale, Typhula incarnata, Pseudocercosporella herpotrichoides, Fusarium culmorum, Rhizoctonia cerealis, Gaeumannomyces graminis) and soybeans (e.g. Phakopsora pachyrhizi, Microsphaera diffusa, Septoria glycines, Cercospora sojina, Cercospora kikuchii, Corynespora cassiicola, Colletotrichum truncatum, Peronospora manshurica, Alternaria spp., Phomopsis phaseoli, Diaporthe phaseolorum, Phialophora gregata, Fusarium solani, Sclerotinia sclerotiorum, Sclerotinia rolfsii, Phytopthora megasperma, Rhizoctonia solani, Dematophora necatrix, Macrophomina phaseolina).
The inventive compositions are particularly suitable for controlling phytopathogenic fungi in soybeans, vegetables and fruit crops.
The compositions according to the invention are furthermore suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophio- stoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chae- tomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Po- ria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.
Application of the inventive compositions to useful plants may also lead to an increase in the crop yield.
The components 1) and 2) can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not hav- ing any effect on the result of the control measures.
When preparing the compositions, it is preferred to employ the commercially available formulations of components 1 ) and 2), to which further compounds active against harmful fungi or other pests, such as insects, arachnids or nematodes, or else herbi- cidal or growth-regulating active compounds or fertilizers may be added.
Usually, compositions comprising component 1 ) and 2), wherein component 2) consists of only one active ingredient (II), are employed. However, in certain cases compositions wherein component 2) consists of two or, if appropriate, more active components may be advantageous.
Suitable further active components in the above sense are in particular the active compounds Il mentioned at the outset, and in particular the preferred active compounds Il mentioned above. Components 1 ) and 2) are usually employed in a weight ratio of from 100:1 to 1 :100, preferably from 30:1 to 1 :30, in particular from 15:1 to 1 :15.
The further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to component 1 ).
Depending on the particular components and the desired effect, the application rates for component 1 ) are generally from 1 I to 100 I broth containing the strain per hectare, preferably from 1 I to 50 I/ha, in particular from 1 to 20 I/ha.
Correspondingly, the application rates for component 2) are generally from 1 to 2000 g/ha, preferably from 10 to 1500 g/ha, in particular from 40 to 1000 g/ha.
The method for controlling harmful fungi is carried out by the separate or joint applica- tion of a component 1 ) and a component 2), or a composition comprising components 1 ) and 2), by spraying or dusting the seeds, the plants or the soils before or after sowing of the plants or before or after emergence of the plants.
The compositions according to the invention, or the single components separately, can be converted into customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the mixture according to the invention.
The formulations are prepared in a known manner, for example by extending the single components with solvents and/or carriers, if desired using emulsifiers and dispersants. Solvents/auxiliaries suitable for this purpose are essentially:
- water, aromatic solvents (for example Solvesso® products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (N-methylpyrrolidone, N-octylpyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
- carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example highly disperse silica, silicates); emulsifiers such as nonionogenic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants such as lignosulfite waste liquors and methylcellulose.
Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene- sulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy- ethylene octylphenyl ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether, tristearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.
Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone and water.
Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
In order to achieve good dispersion and adhesion of compositions within the present invention, it may be advantageous to formulate the whole broth culture, supernatant and/or metabolite with components that aid dispersion and adhesion.
In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the components.
The active compounds (II) are employed in a purity of from 90% to 100%, preferably
95% to 100% (according to NMR spectrum).
The following are examples of formulations: 1. Products for dilution with water A) Water-soluble concentrates (SL)
10 parts by weight of a composition according to the invention are dissolved in 90 parts by weight of water or in a water-soluble solvent. As an alternative, wetting agents or other auxiliaries are added. Dilution with water results in a formulation having a content of 10% by weight of components 1 ) and 2) is obtained.
B) Dispersible concentrates (DC)
20 parts by weight of a composition according to the invention are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion having a content of 0% by weight of components 1 ) and 2).
C) Emulsifiable concentrates (EC)
15 parts by weight of a composition according to the invention are dissolved in 75 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has a content of 15% by weight of components 1 ) and 2).
D) Emulsions (EW, EO) 25 parts by weight of a composition according to the invention are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This composition is introduced into 30 parts by weight of water by means of an emulsifying machine (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has a content of 25% by weight of components 1 ) and 2).
E) Suspensions (SC, OD)
In an agitated ball mill, 20 parts by weight of a composition according to the invention are comminuted with addition of 10 parts by weight of dispersants and wetting agents and 70 parts by weight of water or an organic solvent to give a fine suspension. Dilution with water gives a stable suspension having a content of 20% by weight of components 1 ) and 2).
F) Water-dispersible granules and water-soluble granules (WG, SG) 50 parts by weight of a composition according to the invention are ground finely with addition of 50 parts by weight of dispersants and wetting agents and prepared as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution having a content of 50% by weight of components 1 ) and 2). G) Water-dispersible powders and water-soluble powders (WP, SP) 75 parts by weight of a composition according to the invention are ground in a rotor- stator mill with addition of 25 parts by weight of dispersants, wetting agents and silica gel. Dilution with water gives a stable dispersion or solution having a content of 75% by weight of components 1 ) and 2).
2. Products to be applied undiluted
H) Dustable powders (DP)
5 parts by weight of a composition according to the invention are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having a content of 5% by weight of components 1 ) and 2).
J) Granules (GR, FG, GG, MG)
0.5 part by weight of a composition according to the invention is ground finely and associated with 99.5 parts by weight of carriers. Current methods are extrusion, spray- drying or the fluidized bed. This gives granules to be applied undiluted having a content of 0.5% of weight of components 1 ) and 2).
K) ULV solutions (UL)
10 parts by weight of a composition according to the invention are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted having a compound content of 10% by weight of components 1) and 2).
Components 1 ) and 2) can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of components 1) and 2) according to the invention.
Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetting agent, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water. The concentrations of the components in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 100%, preferably from 0.01 to 100%.
Components 1 ) and 2) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply components 1 ) and 2) without additives.
Oils of various types, wetting agents or adjuvants may be added to the component 1 ) or 2), even, if appropriate, not until immediately prior to use (tank mix). These agents are typically admixed with component 1 ) or 2) according to the invention in a weight ratio of from 1 :100 to 100:1 , preferably from 1 :10 to 10:1.
Suitable adjuvants in this sense are in particular: organically modified polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus 245®, Atplus MBA 1303®, Plurafac LF 300® and Lutensol ON 30®; EO/PO block polymers, for example Pluronic RPE 2035® and Genapol B®; alcohol ethoxylates, for example Lutensol XP 80®; and sodium dioctylsulfosuccinate, for example Leophen RA®.
Components 1 ) and 2) or the composition comprising components 1) and 2), or the corresponding formulations, are applied by treating the harmful fungi, the plants, seeds, soils, areas, materials or spaces to be kept free from them with a fungicidally effective amount of the composition or, in the case of separate application, of the components 1 ) and 2) separately. Application can be before or after the infection by harmful fungi.
The fungicidal action of components 1) and 2) and of the compositions according to the invention was demonstrated by the tests below.
Components 1 ) and 2), separately or jointly, were prepared as a stock solution comprising 25 mg of active compound which was made up to 10 ml using a mixture of acetone and/or DMSO and the emulsifier Uniperol® EL (wetting agent having an emulsifying and dispersing action based on ethoxylated alkylphenols) in a ratio by volume of solvent/emulsifier of 99:1. The mixture was then made up to 100 ml with water. This stock solution was diluted with the solvent/emulsifier/water mixture described to give the concentration of active compound stated below.
The visually determined percentages of infected leaf areas were converted into efficacies in % of the untreated control:
The efficacy (E) is calculated as follows using Abbot's formula:
E = (1 - α/β ) ■ 100 α corresponds to the fungicidal infection of the treated plants in % and β corresponds to the fungicidal infection of the untreated (control) plants in %
An efficacy of 0 means that the infection level of the treated plants corresponds to that of the untreated control plants; an efficacy of 100 means that the treated plants were not infected.
The expected efficacies of active compound combinations were determined using Colby's formula (Colby, S. R. " Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, 1J5, pp. 20-22, 1967) and compared with the observed efficacies.
Colby's formula: E = x + y - x° y/100
E expected efficacy, expressed in % of the untreated control, when using the mixture of the active compounds A and B at the concentrations a and b x efficacy, expressed in % of the untreated control, when using the active compound A at the concentration a y efficacy, expressed in % of the untreated control, when using the active compound B at the concentration b

Claims

Claims
1. A fungicidal composition for controlling phytopathogenic harmful fungi, comprising
1 ) a fungicidal strain (I) selected from a) the Bacillus substilis strain with NRRL Accession No. B-21661 , and b) the Bacillus pumilus strain with NRRL Accession No. B-30087, or a mutant of these strains having all the identifying characteristics of the respective strain, or a metabolite produced by the respective strain that exhibits activity against plant pathogenic fungi, and
2) at least one chemical compound (II), selected from the active compound groups A) to F):
A) azoles selected from the group consisting of azaconazole, diniconazole- M, oxpoconazol, paclobutrazol, uniconazol, 1-(4-chloro-phenyl)-2- ([1 ,2,4]triazol-1-yl)-cycloheptanol and imazalil-sulfphate;
B) strobilurins selected from the group consisting of 2-(2-(6-(3-chloro-2- methyl-phenoxy)-5-fluoro-pyrimidin-4-yloxy)-phenyl)-2-methoxyimino-N- methyl-acetamide and 3-methoxy-2-(2-(N-(4-methoxy-phenyl)-cyclo- propanecarboximidoylsulfanylmethyl)-phenyl)-acrylic acid methyl ester;
C) carboxamides selected from the group consisting of benalaxyl, benalaxyl-M, 2-amino-4-methyl-thiazole-5-carboxamide, 2-chloro-N- (1 ,1 ,3-trimethyl-indan-4-yl)-nicotinamide, N-(2-(1 ,3-dimethylbutyl)- phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, N-(4'-chloro- 3\5-difluoro-biphenyl-2-yl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4- carboxamide, N-(4'-chloro-3',5-difluoro-biphenyl-2-yl)-3-trifluoromethyl-1 - methyl-1 H-pyrazole-4-carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(trans-2-bi- cyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H-pyrazole-4- carboxamide, fluopyram, N-(3-ethyl-3,5-5-trimethyl-cyclohexyl)-3-formyl- amino-2-hydroxy-benzamide, oxytetracyclin, silthiofam, N-(6-methoxy- pyridin-3-yl) cyclopropanecarboxylic acid amide, penthiopyrad, isopyrazam and a 1-methyl-pyrazol-4-ylcarboxamide of the formula III
Figure imgf000060_0001
in which the substituents are as defined below: X is hydrogen or fluorine; R1 is Ci-C4-alkyl or Ci-C4-haloalkyl; R2 is hydrogen or halogen;
R3, R4 and R5 independently of one another are hydrogen, cyano, nitro, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy, CrC4- haloalkoxy or Ci-C4-alkylthio;
heterocyclic compounds selected from the group consisting of 5-chloro-
7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidine, 2,3,5,6-tetrachloro-4-methanesulfonyl-pyridine, 3,4,5- trichloro-pyridine-2,6-di-carbonitrile, N-(1-(5-bromo-3-chloro-pyridin-2-yl)- ethyl)-2,4-dichloro-nicotinamide, N-((5-bromo-3-chloro-pyridin-2-yl)- methyl)-2,4-dichloro-nicotinamide, diflumetorim, nitrapyrin, dodemorph- acetate, fluoroimid, blasticidin-S, chinomethionat, debacarb, oxolinic acid, piperalin and an azolopyrimidinylamine of the formula IV
Figure imgf000060_0002
in which the substituents have the following meanings: E1 is C3-Ci2-alkyl, C2-Ci2-alkenyl, C5-Ci2-alkoxyalkyl, C3-C6-cycloalkyl, phenyl or phenyl-Ci-C4-alkyl; E2 is Ci-Ci2-alkyl, C2-Ci2-alkenyl, Ci-C4-haloalkyl or Ci-C4-alkoxy-Ci-
C4-alkyl;
where the aliphatic chains in E1 and/or E2 may be substituted by one to four identical or different groups Ra: Ra is halogen, cyano, hydroxyl, mercapto, Ci-Cio-alkyl, C1-C10- haloalkyl, Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, Ci-Cβ- alkoxy, d-Ce-alkylthio, Ci-C6-alkoxy-Ci-C6-alkyl or NRARB; RA, RB independently of one another are hydrogen or Ci-Cβ-alkyl; where the cyclic groups in E1 and/or Ra may be substituted by one to four groups Rb: Rb is halogen, cyano, hydroxyl, mercapto, nitro, NRARB, Ci-Cio-alkyl, C-i-Cε-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl or Ci-Cβ-alkoxy;
E3 is hydrogen, halogen, cyano, NRARB, hydroxyl, mercapto, Ci-Cβ- alkyl, Ci-C6-haloalkyl, C3-C8-cycloalkyl, Ci-C6-alkoxy, CrC6- alkylthio, Cs-Cs-cycloalkoxy, Cs-Cs-cycloalkylthio, carboxyl, formyl, Ci-Cio-alkyl- carbonyl, C-i-C-io-alkoxycarbonyl, C2-C10- alkenyloxycarbonyl, C2-C10- alkynyloxycarbonyl, phenyl, phenoxy, phenylthio, benzyloxy, benzylthio or Ci-C6-alkyl-S(O)m-;
m is 0, 1 or 2;
A is CH or N;
E) carbamates selected from the group consisting of methasulphocarb and propamocarb hydrochlorid;
F) other fungicides selected from the group consisting of metrafenone, dodine free base, guazatine-acetate, iminoctadine-triacetate, iminoc- tadine-tris(albesilate), kasugamycin-hydrochlorid-hydrat, dichlorophen, pentachlorophenol and its salts, N-(4-chloro-2-nitro-phenyl)-N-ethyl-4- methyl-benzenesulfon-amide, dicloran, nitrothal-isopropyl, tecnazen, bi- phenyl, bronopol, diphenylamine, mildiomycin, oxin-copper, pro- hexadione calcium, N-(cyclopropylmethoxyimino-(6-difluoromethoxy-2,3- difluoro-phenyl)-methyl)-2-phenyl acetamide, N'-(4-(4-chloro-3- trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl forma- midine, N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)- N-ethyl-N-methyl formamidine, N'-(2-methyl-5-trifluormethyl-4-(3- trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine and N'- (5-difluormethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-
N-methyl formamidine;
in a synergistically effective amount.
2. The fungicidal composition according to claim 1 , comprising as component 1 ) a commercially available formulation of strain a) or b).
3. The fungicidal mixture according to claim 1 or 2, comprising as component 2) at least one chemical compound (II), selected from the active compound groups C),
D) and F).
4. The fungicidal mixture according to claim 1 or 2, comprising as component 2) 5-chloro-7-(4-methylpiperidin-1 -yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5- a]pyrimidine or an azolopyrimidin-7-ylamine of the formula IV.
5. The fungicidal composition according to claim 1 or 2, comprising as component 2) N-(2-(1 ,3-dimethylbutyl)-phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4- carboxamide, N-(cis-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl-1 -methyl-1 H- pyrazole-4-carboxamide, N-(trans-2-bicyclopropyl-2-yl-phenyl)-3-difluoromethyl- 1 -methyl-1 H-pyrazole-4-carboxamide, penthiopyrad or a 1-methyl-pyrazol-4-yl- carboxamide of the formula III.
6. The fungicidal composition according to claim 1 or 2, comprising an additional active compound V, selected from the groups G) to M):
G) azoles selected from the group consisting of bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, enilconazole, epoxiconazole, fluquinconazole, fenbuconazole, flusilazole, flutriafol, hexaconazole, imiben- conazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, triadimefon, triadimenol, tebuconazole, tet- raconazole, triticonazole, prochloraz, pefurazoate, imazalil, triflumizole, cya- zofamid, benomyl, carbendazim, thiabendazole, fuberidazole, ethaboxam, et- ridiazole and hymexazole;
H) strobilurins selected from the group consisting of azoxystrobin, dimoxy- strobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, enestroburin, methyl (2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl (2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)- carbamate and methyl 2-(ortho-(2,5-dimethylphenyloxymethylene)phenyl)-3- methoxyacrylate;
J) carboxamides selected from the group consisting of carboxin, boscalid, fen- hexamid, flutolanil, furametpyr, mepronil, metalaxyl, mefenoxam, ofurace, oxadixyl, oxycarboxin, penthiopyrad, thifluzamide, tiadinil, 3,4-dichloro-N-(2- cyanophenyl)isothiazole-5-carboxamide, dimethomorph, flumorph, flume- tover, fluopicolide (picobenzamid), zoxamide, carpropamid, diclocymet, mandipropamid, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxy- phenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-(4-[3-(4- chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethanesulfonyl- amino-3-methylbutyramide, methyl 3-(4-chlorophenyl)-3-(2-isopropoxy- carbonylamino-3-methylbutyrylamino)propionate, N-(4'-bromobiphenyl-2-yl)- 4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4'-trifluoromethyl- biphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4'-chloro- 3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methyl-thiazole-5-carboxamide, N- (3\4'-dichloro-4-fluorobiphenyl-2-yl)-3-difluoro-methyl-1-methylpyrazole-
4-carboxamide, N-(3\4'-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl- 1 -methylpyrazole-4-carboxamide and N-(2-cyano-phenyl)-3,4-dichloro- isothiazole-5-carboxamide;
K) heterocyclic compounds selected from the group consisting of fluazinam, pyrifenox, bupirimate, cyprodinil, fenarimol, ferimzone, mepanipyrim, nuari- mol, pyrimethanil, triforine, fenpiclonil, fludioxonil, aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, iprodione, procymidone, vinclozolin, famoxadone, fenamidone, octhilinone, probenazole, anilazine, diclomezine, pyroquilon, proquinazid, tricyclazole, 2-butoxy-6-iodo-3-propylchromen-4- one, acibenzolar-S-methyl, captafol, captan, dazomet, folpet, fenoxanil, quin- oxyfen and N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)- [1 ,2,4]triazole-1 -sulfonamide;
L) carbamates selected from the group consisting of mancozeb, maneb, metam, metiram, ferbam, propineb, thiram, zineb, ziram, diethofencarb, iprovalicarb, flubenthiavalicarb, propamocarb, 4-fluorophenyl N-(1-(1-(4- cyanophenyl)ethanesulfonyl)but-2-yl)carbamate, methyl 3-(4-chlorophenyl)- 3-(2-isopropoxycarbonylamino-3-methyl-butyrylamino)propanoate and carbamate oxime ethers of the formula Vl
Figure imgf000063_0001
in which Z is N or CH;
M) other fungicides selected from the group consisting of guanidine, dodine, iminoctadine, guazatine, antibiotics: kasugamycin, streptomycin, polyoxin, validamycin A, nitrophenyl derivatives: binapacryl, dinocap, dinobuton, sulfur-containing heterocyclyl compounds: dithianon, isoprothiolane, organometallic compounds: fentin salts, organophosphorus compounds: edifenphos, iprobenfos, fosetyl, fosetyl-aluminum, phosphorous acid and its salts, pyrazophos, tolclofos- methyl, organochlorine compounds: chlorothalonil, dichlofluanid, flusulfamide, hexachlorobenzene, phthalide, pencycuron, quintozene, thiophanate-methyl, tolylfluanid, inorganic active compounds: Bordeaux mixture, copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate, sulfur, others: cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl and spiroxamine.
7. The fungicidal composition according to any of claims 1 to 6, comprising the components 1 ) and 2) in a weight ratio of from 100:1 to 1 :100.
8. A fungicidal agent, comprising at least one liquid or solid carrier and a composition according to any of claims 1 to 6.
9. A method for controlling phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil, seed, areas, materials or spaces are/is treated with an effective amount of a component 1 ) and a component 2) according to any of claims 1 to 6.
10. The method according to claim 9, wherein components 1 ) and 2) according to any of claims 1 to 6 are applied simultaneously, that is jointly or separately, or in succession.
1 1. Seed, comprising a composition according to any of claims 1 to 6.
12. The use of components 1 ) and 2) according to any of claims 1 to 6 for preparing a fungicidal agent suitable for controlling harmful fungi.
13. The use of components 1 ) and 2) according to any of claims 1 to 6 for treating transgenic plants or the seed thereof.
PCT/EP2008/062279 2007-09-20 2008-09-16 Combinations comprising a fungicidal strain and an active compound WO2009037242A2 (en)

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BR122017018225A BR122017018225B1 (en) 2007-09-20 2008-09-16 fungicidal composition, its uses, fungicidal agent, method for controlling phytopathogenic harmful fungi, and seed resistant to phytopathogenic harmful fungi
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US20160295869A1 (en) 2016-10-13
PL2292098T3 (en) 2020-05-18
UA109036C2 (en) 2015-07-10
CL2012003628A1 (en) 2014-01-24
HUE048086T2 (en) 2020-05-28
US9743674B2 (en) 2017-08-29
UA106719C2 (en) 2014-10-10
BRPI0816948B1 (en) 2018-01-23
CA2698560A1 (en) 2009-03-26
CR11339A (en) 2010-04-21
EP2319319A1 (en) 2011-05-11
EP2292098B1 (en) 2019-11-06
ECSP17003592A (en) 2017-03-31
PH12015502617A1 (en) 2017-04-24
EA018247B1 (en) 2013-06-28
BRPI0816948A2 (en) 2014-10-07
EA201200511A1 (en) 2012-08-30
US10212942B2 (en) 2019-02-26
TW200922475A (en) 2009-06-01
CA3040432A1 (en) 2009-03-26
BR122017018225A8 (en) 2017-12-19
CL2012003627A1 (en) 2013-09-23
US20100209410A1 (en) 2010-08-19
EP3381289A1 (en) 2018-10-03
PT2292098T (en) 2020-01-21
EA201200508A1 (en) 2012-08-30
NZ600929A (en) 2014-02-28
KR20100061735A (en) 2010-06-08
AU2008300629A1 (en) 2009-03-26
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KR20150066600A (en) 2015-06-16
EA201200512A1 (en) 2012-08-30
IL204151A (en) 2015-04-30
EA201000430A1 (en) 2010-10-29
EP2614712A1 (en) 2013-07-17
EP2292098A1 (en) 2011-03-09
EA019915B1 (en) 2014-07-30
EA020182B1 (en) 2014-09-30
ES2766951T3 (en) 2020-06-15
PH12015502617B1 (en) 2017-04-24
NZ599174A (en) 2012-08-31
US9392797B2 (en) 2016-07-19
US20150264939A1 (en) 2015-09-24
EA201200510A1 (en) 2012-08-30
PE20090707A1 (en) 2009-07-17
EA020203B1 (en) 2014-09-30
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