EP2410850A2 - Synergistische wirkstoffkombinationen - Google Patents

Synergistische wirkstoffkombinationen

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Publication number
EP2410850A2
EP2410850A2 EP09776472A EP09776472A EP2410850A2 EP 2410850 A2 EP2410850 A2 EP 2410850A2 EP 09776472 A EP09776472 A EP 09776472A EP 09776472 A EP09776472 A EP 09776472A EP 2410850 A2 EP2410850 A2 EP 2410850A2
Authority
EP
European Patent Office
Prior art keywords
spp
formula
methyl
chloro
plants
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP09776472A
Other languages
German (de)
English (en)
French (fr)
Inventor
Peter Jeschke
Robert Velten
Heike Hungenberg
Wolfgang Thielert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer CropScience AG
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
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP2410850A2 publication Critical patent/EP2410850A2/de
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/72—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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to novel drug combinations which contain a known compound of formula (I) on the one hand and at least one known fungicidal active ingredient on the other hand and are very well suited for controlling unwanted animal pests such as insects and unwanted phytopathogenic fungi.
  • A represents pyrid-2-yl or pyrid-4-yl or pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or for pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or 2-chloro-pyrazin-5-yl or l, 3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl, or
  • A is a radical pyrimidinyl, pyrazolyl, thiophenyl, oxazolyl, isoxazolyl, 1,2,4-oxadiazolyl, isothiazolyl, 1, 2,4-triazolyl or 1,2,5-thiadiazolyl, which is optionally substituted by fluorine, chlorine, Bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 3 -alkylthio (which is optionally substituted by fluorine and / or chlorine), or C 1 -C 3 - Alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine),
  • X is halogen, alkyl or haloalkyl
  • Y is halogen, alkyl, haloalkyl, haloalkoxy, azido or cyano and
  • R 1 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, halocycloalkyl, alkoxy, alkoxyalkyl, or halocycloalkylalkyl,
  • substituted halopyrimidines have fungicidal properties (cf., DE-Al-196 46 407, EP-B-712 396).
  • a 2 is NH or O
  • a 3 is N or CH
  • R 11 is in each case optionally monosubstituted or disubstituted by identical or different chlorine, cyano, methyl or trifluoromethyl-substituted phenyl, phenoxy or pyridinyl, or for 1- (4-chlorophenyl) -pyrazol-3-yl or for 1,2-propanedione bis (O-methyloxime) -1-yl,
  • R 12 is hydrogen or fluorine
  • Q is hydrogen or SH, m is 0 or 1,
  • R 13 is hydrogen, fluorine, chlorine, phenyl or 4-chlorophenoxy
  • R 14 is hydrogen or chlorine
  • R 15 and R 17 together then represent -CH 2 -CH 2 -CH [CH (CH 3 ) 2 ] - or -CH 2 -CH 2 -C (CHj) 2 -,
  • a 5 is C or Si (silicon),
  • R 15 is hydrogen, hydroxy or cyano
  • R 16 represents 1-cyclopropylethyl, 1-chlorocyclopropyl, dC 4 alkyl, C r C 6 hydroxyalkyl, C, -C 4 - alkylcarbonyl, Ci-C 2 -haloalkoxy-C r C 2 alkyl, trimethylsilyl-C 2- alkyl, monofluorophenyl, or phenyl,
  • R 15 and R 16 also together represent -0-CH 2 -CH (R 18 ) -O-, -O-CH 2 -CH (R 18 ) -CH 2 -, or
  • R 18 is hydrogen, C 1 -C 4 alkyl or bromo
  • X is 2-chloro-3-pyridinyl, 1-methylpyrazol-4-yl which is substituted in the 3-position by methyl, trifluoromethyl or difluoroethyl and in the 5-position by hydrogen or chlorine, for 4-ethyl-2 ethylamino-l, 3-thiazol-5-yl, for 1-methylcyclohexyl, for 2,2-dichloro-l-ethyl-3-methylcyclopropyl, for 2-fluoro-2-propyl, 3,4- Dichloroisothiazol-5-yl, 5,6-dihydro-2-methyl-1,4-oxathiin-3-yl, 4-methyl-1,2,3-thiadiazol-5-yl, 4,5-dimethyl 2-trimethylsilyl-thiophen-3-yl, 1-methylpyrrol-3-yl which is substituted in the 4-position by methyl or trifluoromethyl and in the 5-position by hydrogen or chlorine, or represents phenyl which is monosubstitute
  • Y is a direct bond, optionally substituted by chlorine, cyano or oxo substituted Q-C 6 alkanediyl (alkylene), C 2 -C 6 alkylenediyl (alkenylene) or thiophenediyl,
  • Z is hydrogen, CpC ⁇ -alkyl or the group stands in which
  • R is hydrogen, chlorine, cyano, C 1 -C 6 -alkyl, by phenyl which may be monosubstituted or disubstituted by identical or different substituents, chlorine or di (C 1 -C 3 -alkyl) aminocarbonyl, or a radical from the series
  • R 21 is hydrogen, chlorine or isopropoxy
  • R 22 represents hydrogen, chlorine, hydroxyl, methyl, trifluoromethyl or di (C 1 -C 3 -alkyl) aminocarbonyl
  • R 20 and R 21 also together represent * -CH (CH 3 ) -CH 2 -C (CH 3 ) 2 - or * -CH (CH 3 ) -OC (CH 3 ) 2 -, wherein the bond marked with * is linked to R 20 or out of line for a rest
  • R 23 is benzyl, furyl or methoxymethyl
  • R 24 is methyl, cyclopropyl or 1-propynyl
  • R 25 and R 26 are each hydrogen or together are -O-CF 2 -O-,
  • R 27 is hydrogen, C 1 -C 4 -alkylaminocarbonyl or 3,5-dimethylisoxazol-4-ylsulfonyl,
  • R 28 is chloro, methoxycarbonylamino, chlorophenyl, furyl or thiazolyl
  • R 29 is n- or iso-propyl
  • R 30 is di (C 1 -C 2 -alkyl) aminoC 2 -C 4 -alkyl or diethoxyphenyl,
  • R 31 and R 32 independently of one another represent hydrogen or methyl
  • R 33 is C r C 4 alkyl (preferably C 2 -C 4 alkyl), C 5 -C 12 cycloalkyl (preferably C 10 -C 2 -Cycloal- alkyl), phenyl-Ci-C 4 alkyl, which may be substituted in the phenyl moiety by halogen or C 1 -C 4 -alkyl, or by acrylyl which is substituted by chlorophenyl and dimethoxyphenyl;
  • R 34 is chlorine or cyano
  • R 35 is chlorine or nitro
  • R 36 is chlorine
  • R 35 and R 36 furthermore together represent -0-CF 2 -O-;
  • R 37 is phenyl, phenyl, 2-naphthyl, 1,2,3,4-tetrahydronaphthyl or indanyl unsubstituted or substituted by fluorine, chlorine, bromine, methyl or ethyl;
  • a 7 is a direct bond or -O-
  • R is hydrogen or C r C 4 alkyl
  • R 39 is Ci-C ⁇ -alkyl
  • R is C r C 6 alkyl or C 2 -C 6 alkenyl
  • R 41 is C r C 6 -alkyl
  • R 40 and R 41 furthermore together represent GrC 5 alkanediyl (alkylene) which is mono- or disubstituted by CpC ö alkyl,
  • R 42 is bromine or chlorine
  • R 43 and R 47 independently of one another represent hydrogen, fluorine, chlorine or methyl
  • R 44 and R 46 independently of one another represent hydrogen or fluorine
  • R 45 is hydrogen, fluorine or methyl
  • R 4 is C r C 6 -alkyl
  • R, 4 4 9 y is C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl;
  • R is hydrogen or fluorine
  • R 51 is fluorine, chlorine, bromine, methyl, trifluoromethyl, trifluoromethoxy
  • R 52 is hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl
  • Het stands for one of the following residues Hetl to Het7:
  • R 53 is iodine, methyl, difluoromethyl or trifluoromethyl
  • R 54 is hydrogen, fluorine, chlorine or methyl
  • R 55 is methyl, difluoromethyl or trifluoromethyl
  • R 56 represents chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl
  • R 57 is methyl or trifluoromethyl.
  • the fungicidal action of the active compound combinations according to the invention is substantially higher than the sum of the effects of the individual active compounds. So there is an unpredictable, true synergistic effect and not just an effect supplement.
  • the active compound combinations according to the invention contain, in addition to at least one compound of the formula (I), at least one active compound of the abovementioned groups (2) to (27).
  • the active compound combinations according to the invention preferably contain exactly one compound of the formula (I) and exactly one active compound of the groups (2) to (27) listed above. Further preferred are active compound combinations which contain a compound of the formula (I) and two active compounds of the groups (2) to (27) listed above. Also preferred are active compound combinations which comprise two compounds of the formula (I) and one active ingredient of the groups (2) to (27) listed above.
  • A is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-l, 3-thiazol-5-yl, 2-chloropyrimidin-5-yl, 2-trifluoromethyl-pyrimidin-5-yl, 5,6-difluoropyrid-3-yl, 5-Chloro-6-fluoro-pyrid-3-yl, 5-bromo-6-fluoro-pyrid-3-yl, 5-iodo-6-fluoro-pyrid-3-yl, 5-fluoro-6-chloro pyrid-3-y
  • R 1 preferably represents optionally fluorine-substituted C 1 -C 5 -alkyl, C 2 -C 5 -alkenyl, C 3 -C 5 -cycloalkyl, C 3 -C 5 -cycloalkylalkyl or C 1 -C 5 -alkoxy.
  • R 1 particularly preferably represents methyl, methoxy, ethyl, propyl, vinyl, allyl, propargyl, cyclopropyl, 2-fluoroethyl, 2,2-difluoroethyl or 2-fluorocyclopropyl.
  • R 1 very particularly preferably represents methyl, cyclopropyl, methoxy, 2-fluoroethyl or 2,2-difluoroethyl.
  • A most preferably represents the residue 6-chloro-pyrid-3-yl or S-fluoro- ⁇ -chloro-pyrid-S-yi.
  • R 1 is most preferably methyl, 2-fluoroethyl or 2,2-difluoro-ethyl.
  • A is 6-chloro-pyrid-3-yl
  • R 1 is methyl
  • R 1 is ethyl
  • R 1 is cyclopropyl
  • R 1 is 2-fluoroethyl
  • R 1 is 2,2-difluoroethyl.
  • a preferred subgroup of the compounds of the formula (I) are those of the formula (I-a)
  • B is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl, which may optionally be in 6-
  • Position is substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or pyrazine-3-yl or 2-chloro-pyrazine 5-yl or for l, 3-thiazol-5-yl which is optionally substituted in the 2-position by chlorine or methyl,
  • R 2 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl,
  • B is preferably 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.
  • R 2 preferably represents fluorine-substituted Ci-C 5 alkyl, C 2 -C 5 alkenyl, C 3 -C 5 - cycloalkyl or C 3 -C 5 cycloalkylalkyl.
  • B particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6
  • R 2 particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluorocyclopropyl.
  • B is very particularly preferably the radical 6-chloropyrid-3-yl.
  • R 2 is most preferably 2-fluoro-ethyl or 2,2-difluoro-ethyl.
  • B is 6-chloro-pyrid-3-yl
  • R 2 is 2-fluoroethyl
  • R 2 is 2,2-difluoroethyl.
  • Another preferred subgroup of the compounds of the formula (I) are those of the formula (I-b)
  • R 3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or alkoxy
  • D is preferably one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5-bromo-6-fluoropyrid-3-yl, 5-iodo 6-fluoro-pyrid-3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl , 5-iodo-6-chloro-pyrid-3-yl, 5-iodo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid 3-yl, 5-fluoro-6-iodo-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl
  • R 3 is preferably C r C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 cycloalkyl.
  • D is more preferably 5-fluoro-6-chloro-pyrid-3-yl, 5,6-dichloro-pyrid-3-yl, 5-bromo-6-chloro-pyrid-3-yl, 5-fluoro-6 bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5 Chloro-6-iodo-pyrid-3-yl or 5-difluoromethyl-6-chloro-pyrid-3-yl.
  • R 3 particularly preferably represents C 1 -C 4 -alkyl.
  • D is most preferably 5-fluoro-6-chloro-pyrid-3-yl or 5-fluoro-6-bromo-pyrid-3-yl.
  • R 3 very particularly preferably represents methyl, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
  • D is most preferably 5-fluoro-6-chloro-pyrid-3-yl.
  • R 3 most preferably represents methyl or cyclopropyl.
  • D is 5-fluoro-6-chloropyrid-3-yl
  • D is 5,6-dichloropyrid-3-yl
  • D is 5-bromo-6-chloro-pyrid-3-yl
  • D is 5-methyl-6-chloro-pyrid-3-yl
  • D is 5-chloro-6-bromo-pyrid-3-yl
  • D is 5-chloro-6-iodo-pyrid-3-yl
  • R 3 is methyl
  • R 3 is ethyl
  • R 3 is cyclopropyl
  • Another preferred subgroup of the compounds of the formula (I) are those of the formula (I-c)
  • R 4 is haloalkyl, haloalkenyl, halocycloalkyl or halocycloalkylalkyl.
  • E is preferably one of the radicals 5,6-difluoropyrid-3-yl, 5-chloro-6-fluoropyrid-3-yl, 5
  • R 4 preferably represents fluorine-substituted Ci-Cs-alkyl, C 2 -C 5 alkenyl, C 3 -C 5 - cycloalkyl or C r C 5 cycloalkylalkyl.
  • E particularly preferably represents 2-chloro-pyrimidin-5-yl, 5-fluoro-6-chloro-pyrid-3-yl, 5,6-
  • Dichloro-pyrid-3-yl 5-bromo-6-chloro-pyrid-3-yl, 5-fluoro-6-bromo-pyrid-3-yl, 5-chloro-6-bromo-pyrid-3-yl, 5,6-dibromo-pyrid-3-yl, 5-methyl-6-chloro-pyrid-3-yl, 5-chloro-6-iodo-pyrid-3-yl or 5-difluoromethyl-6-chloro-pyrid 3-yl.
  • R 4 particularly preferably represents 2-fluoroethyl, 2,2-difluoroethyl, 2-fluoro-cyclopropyl.
  • E is most preferably 5-fluoro-6-chloro-pyrid-3-yl.
  • R 4 is very particularly preferably 2-fluoroethyl or 2,2-difluoroethyl.
  • E is 5-bromo-6-chloro-pyrid-3-yl
  • E is 5-fluoro-6-bromo-pyrid-3-yl
  • E is 5-chloro-6-iodo-pyrid-3-yl
  • R 4 is 2-fluoroethyl
  • R 4 is 2,2-difluoroethyl.
  • a preferred subgroup of the compounds of the formula (I) are those of the formula (I-d)
  • G is pyrid-2-yl or pyrid-4-yl or pyrid-3-yl which is optionally substituted in the 6-position by fluorine, chlorine, bromine, methyl, trifluoromethyl or trifluoromethoxy or for pyridazin-3-yl, which is optionally substituted in the 6-position by chlorine or methyl or for pyrazine-3-yl or 2-chloro-pyrazin-5-yl or l, 3-thiazol-5-yl, which is optionally substituted in the 2-position by chlorine or methyl, and
  • R 5 is C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 4 cycloalkyl or C 1 -C 4 -alkoxy group,
  • G preferably represents 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid-3-yl, 6-methyl-pyrid-3-yl, 6-trifluoromethyl-pyridine 3-yl, 6-trifluoromethoxypyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 6-methyl-1,4-pyridazin-3-yl, 2-chloro-1,3-thiazole 5-yl or 2-methyl-1,3-thiazol-5-yl.
  • R 5 is preferably C r C 4 alkyl, C r alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl or C 3 -C 4 - cycloalkyl.
  • G particularly preferably represents the radical 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromopyrid-3-yl, 6-chloro-1, 4-pyridazin-3-yl, 2 chloro-l, 3-thiazol-5-yl,
  • R 5 particularly preferably represents methyl, methoxy, ethyl, propyl, vinyl, allyl, propargyl or cyclopropyl.
  • G is very particularly preferably the radical 6-chloropyrid-3-yl.
  • R 5 very particularly preferably represents methyl or cyclopropyl.
  • G is 6-chloro-pyrid-3-yl
  • G is 6-chloro-1, 4-pyridazin-3-yl
  • G is 2-chloro-1,3-thiazol-5-yl
  • R 5 is methyl
  • R 5 is cyclopropyl
  • the formula (H) comprises the following preferred combination partners of the group (2):
  • the formula (IH) comprises the following preferred combination partners of group (3):
  • the formula (IV) comprises the following preferred combination partners of group (4):
  • Preferred combination partners of group (5) are (5-1) Iprovalicarb (known from DE-A 40 26 966) of the formula
  • Penthiopyrad (known from EP-A 0 737 682) of the formula
  • Preferred combination partners of group (7) are
  • Zinc ammoniate ethylenebis (dithiocarbamate) - poly (ethylenethiuram disulfide)
  • the formula (VI) comprises the following preferred combination partners of the group (8):
  • the formula (VII) comprises the following preferred combination partners of the group (9):
  • the formula (VIII) comprises the following preferred combination partners of group (10):
  • the formula (DC) comprises the following preferred combination partners of the group (11):
  • Preferred combination partners of group (14) are:
  • the formula (X) comprises the following preferred combination partners of group (15):
  • Formula (XI) comprises the following preferred combination partners of group (16): (16-1) fenpiclonil (known from EP-A 0 236 272) of the formula
  • the formula (Xu) comprises the following preferred combination partners of group (18), which are known from WO 96/23793 and may each be present as (E) - or (Z) - ⁇ sovne ⁇ e.
  • Compounds of the formula (XS) can therefore be present as a mixture of different isomers or else in the form of a single isomer. Preference is given to compounds of the formula (Xu) in the form of their (E) -isomer:
  • Metrafenone (known from EP-A 0 897 904) of the formula
  • Preferred combination partners of group (20) are:
  • Preferred combination partners of the group (21) are:
  • Preferred combination partners of the group (22) are:
  • Preferred combination partners of group (24) are (24-1) N-O''-dichloro-S-fluoro-1,1'-biphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazole-4-carboxamide (known from WO 03/070705) of the formula
  • Meptyldinocap (RS) -2- (1-methylheptyl) -4,6-dinitrophenyl crotonate known from 'Meptyldinocap: a new active substance for control of powdery mildew Hufhagl, AE; Distler, B .; Bacci, L .; Valverde, P. Dow AgroSciences, Mougins, Fr. International Plant Protection Congress, Proceedings, 16th, Glasgow, United Kingdom, Oct. 15-18, 2007 (2007), 1 32-39 Publisher: British Crop Production Council, Alton, UK
  • the compound (6-7) carpropamid has three asymmetric substituted carbon atoms.
  • the compound (6-7) may therefore be present as a mixture of different isomers or in the form of a single component. Particularly preferred are the compounds
  • the active compound combinations according to the invention preferably comprise at least one of the compounds of the formula (I) which is selected from the group consisting of the compounds of the abovementioned formulas (Ia), (Ib), (Ic) or (Id), with the proviso that 4 - ⁇ [(6-chloropyrid-3-yl) methyl] (methyl) amino ⁇ furan-2 (5H) -one and 4 - ⁇ [(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino ⁇ furan -2 (5H) -one, and an active ingredient selected from the above-mentioned groups (2) to (27).
  • the active compound combinations according to the invention furthermore preferably contain at least one of the compounds of the formula (I) which is selected from the group consisting of the compounds of the abovementioned formulas (Ia), (Ib) or (Ic) and an active ingredient selected from the abovementioned groups (2) to (27).
  • the active compound combinations according to the invention particularly preferably contain at least one of the compounds of the formula (I) in which A is selected from the radicals 6-fluoropyrid-3-yl, 6-chloropyrid-3-yl, 6-bromo-pyrid 3-yl, 5-fluoro-6-chloro-pyrid-3-yl, 2-chloro-l, 3-thiazol-5-yl and 5,6-dichloro-pyrid-3-yl and R 1 is selected from the Radicals methyl, cyclopropyl, methoxy, 2-fluoroethyl or 2,2-difluoro-ethyl, with the proviso that 4 - ⁇ [(6-chloropyrid-3-yl) methyl] (methyl) amino ⁇ furan-2 (5H) -one and 4 - ⁇ [(6-chloropyrid-3-one] yl) methyl] (cyclopropyl) amino ⁇ furan-2 (5H) -one are excluded,
  • the active compound combinations according to the invention very particularly preferably comprise at least one compound of the formula (I) which is selected from the group consisting of the compounds of the formulas (1-1), (1-2), (1-3), (1-4 ), (1-5), (1-6), (1-7) and (1-8), and an active ingredient selected from the above-mentioned groups (2) to (27).
  • each combination represents a preferred erf ⁇ ndungswashe embodiment per se.
  • each combination represents a preferred embodiment of the invention itself.
  • Highlighted embodiments of the invention for the treatment of seed are further active ingredient combinations comprising the compound of formula (1-2) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole (3-17) and / or ipconazole (3-18) and / or triticonazole (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (2- l, 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfon
  • Highlighted embodiments of the invention for treating seed are active ingredient combinations comprising the compound of the formula (1-4) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole ( 3-17) and / or ipconazoles (3-18) and / or triticonazoles (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (1 , 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfonyl)
  • Preferred embodiments of the invention for treating seed are active ingredient combinations comprising the compound of the formula (1-5) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole ( 3-17) and / or ipconazoles (3-18) and / or triticonazoles (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (1 , 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfonyl)
  • Preferred embodiments of the invention for the treatment of seed are active ingredient combinations comprising the compound of the formula (1-6) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole ( 3-17) and / or ipconazoles (3-18) and / or triticonazoles (3-20) and / or triadimenol (3-22) and / or Ca ⁇ ropamid (6-7) and / or N- [2- (1,3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfon
  • Preferred embodiments of the invention for the treatment of seed are active ingredient combinations comprising the compound of the formula (1-7) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole ( 3-17) and / or ipconazoles (3-18) and / or triticonazoles (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (1 , 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfonyl
  • Highlighted embodiments of the invention for treating seed are active ingredient combinations comprising the compound of the formula (1-8) and fluoxastrobin (2-2) and / or trifloxystrobin (2-4) and / or prothioconazole (3-15) and / or tebuconazole ( 3-17) and / or ipconazoles (3-18) and / or triticonazoles (3-20) and / or triadimenol (3-22) and / or carpropamide (6-7) and / or N- [2- (1 , 3-dimethylbutyl) phenyl] -5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide (6-18) and / or thiram (7-5) and / or metalaxyl (8-3) and / or metalaxyl-M (8-4) and / or N- ( ⁇ 4 - [(cyclopropylamino) -carbonyl] -phenyl ⁇ -sulfonyl)
  • the active compound combinations according to the invention comprise, in addition to a compound of the formula (I), at least one active compound of the groups (2) to (27). You may also contain other fungicidal Zumischkomponenten.
  • the combinations according to the invention contain compounds of the formula (I) and a combination partner from one of the groups (2) to (27) in the mixing ratios exemplified in the table below.
  • the mixing ratios are based on weight ratios. The ratio is to be understood as compound of the formula (I): combination partner
  • Group (3) triazoles 125: 1 to 1: 2000 50: 1 to 1: 1000
  • Group (9) anilino-pyrimidines 500: 1 to 1: 100 250: 1 to 1:25
  • Group (11) Carbamate 500: 1 to 1: 100 250: 1 to 1:25
  • the compounds of the formula (I) or the active compounds from the abovementioned groups (2) to (27) having at least one basic center are capable of forming, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, eg perchloric acid, sulfuric acid , Nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids such as unsubstituted or substituted, eg halogen-substituted, C 1 -C 4 -alkanecarboxylic acids, for example acetic acid, saturated or unsaturated dicarboxylic acids, for example oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid and Phthalic acid, hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid and citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted,
  • the compounds of the formula (I) or the active compounds from the abovementioned groups (2) to (27) having at least one acidic group are capable of forming, for example, salts with bases, for example metal salts such as alkali metal or alkaline earth metal salts, eg Sodium, potassium or magnesium salts, or salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a lower mono-, di- or trialkylamine, for example ethyl, diethyl, triethyl or dimethylpropylamine, or a lower mono- , Di- or trihydroxyalkylamine, for example mono-, di- or triethanolamine.
  • bases for example metal salts such as alkali metal or alkaline earth metal salts, eg Sodium, potassium or magnesium salts, or salts with ammonia or an organic amine such as morpholine, piperidine, pyrrolidine, a lower mono-, di- or trialkylamine, for example
  • Agrochemically advantageous salts are preferred in the context of the invention.
  • any reference to the free compounds of formula (I ) or to free active compounds from the abovementioned groups (2) to (27) or their salts so that the corresponding salts or the free compounds of the formula (I) or the free active compounds from the groups listed above ( 2) to (27), if appropriate and appropriate.
  • This also applies correspondingly to tautomers of the compounds of the formula (I) or of the active compounds from the abovementioned groups (2) to (27) and to their salts.
  • active substance combination stands for various combinations of compounds of the formula (I) and active compounds from the abovementioned
  • Groups (2) to (27) eg in the form of a single ready-mix, in a combined spray mixture composed of separate formulations of individual active substances, for example a tank mix or in a combined use of the individual active substances, if they are applied sequentially, for example successively within a reasonably short period of time, eg a few hours or days
  • Application of the compounds of formula (I) and the active compounds from the groups listed above (2) to (27) for the execution of the present invention is not critical.
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rate of the active compound combinations according to the invention is in the treatment of parts of plants, e.g.
  • Leaves from 0.1 to 10,000 g / ha preferably from 10 to 1,000 g / ha, more preferably from 50 to 300 g / ha (when used by pouring or drop, the application rate can even be reduced, especially if inert substrates such as rock wool or perlite are used); in the seed treatment of 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12.5 g per 100 kg of seed; in the soil treatment from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.
  • the active compound combinations according to the invention can be used to plants within a certain period of time after the treatment against attack by phytopathogenic
  • the period of time within which protection is provided generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after
  • the active compound combinations according to the invention are suitable for plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling phytopathogenic fungi such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc., and animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the active compound combinations according to the invention have very good fungicidal properties and can be used for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.
  • the active compound combinations according to the invention are particularly suitable for controlling Phytophthora infestans, Plasmopara viticola and Botrytis cinerea.
  • Fungicides can be used in crop protection to combat Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • Blumeria species such as Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as Puccinia recondita
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Phytophthora species such as Phytophthora infestans
  • Plasmopara species such as Plasmopara viticola
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Pythium species such as Pythium ultimum; Leaf spot diseases and leaf wilt caused by e.g.
  • Alternaria species such as Alternaria solani;
  • Cercospora species such as Cercospora beticola
  • Cladiosporum species such as Cladiosporium cucumerinum
  • Cochliobolus species such as Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);
  • Colletotrichum species such as Colletotrichum lindemuthanium
  • Cycloconium species such as cycloconium oleaginum
  • Diaporthe species such as Diaporthe citri;
  • Elsinoe species such as Elsinoe fawcettii
  • Gloeosporium species such as, for example, Gloeosporium laeticolor
  • Glomerella species such as Glomerella cingulata
  • Guignardia species such as Guignardia bidwelli
  • Leptosphaeria species such as Leptosphaeria maculans
  • Magnaporthe species such as Magnaporthe grisea
  • Mycosphaerella species such as Mycosphaerelle graminicola
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium graminearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g.
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium spp .
  • Claviceps species such as Claviceps purpurea; Fusarium species such as Fusarium culmorum;
  • Gibberella species such as Gibberella zeae
  • Monographella species such as Monographella nivalis
  • Sphacelotheca species such as Sphacelotheca reiliana
  • Tilletia species such as Tilletia caries
  • Urocystis species such as Urocystis occulta
  • Ustilago species such as Ustilago nuda
  • Aspergillus species such as Aspergillus flavus
  • Botrytis species such as Botrytis cinerea
  • Penicillium species such as Penicillium expansum
  • Sclerotinia species such as Sclerotinia sclerotiorum
  • Verticilium species such as Verticilium alboatrum
  • Fusarium species such as Fusarium culmorum
  • Phytophthora species such as Phytophthora cactorum
  • Pythium species such as Pythium ultimum
  • Rhizoctonia species such as Rhizoctonia solani
  • Sclerotium species such as Sclerotium rolfsii
  • Nectria species such as Nectria galligena
  • Monilinia species such as Monilinia laxa
  • Taphrina species such as Taphrina deformans
  • Esca species such as Phaemoniella clamydospora
  • Botrytis species such as Botrytis cinerea
  • Rhizoctonia species such as Rhizoctonia solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as Erwinia amylovora
  • the following diseases of soybean beans can be controlled:
  • Alternaria leaf spot (Alternaria spec. Atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. Truncatum), Brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)) , Dactuliophora leaf spot (Dactuliophora glycines), Downy Mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), Frogeye leaf spot (Cercospora sojina), Leptosphaerulina Leaf Spot (Leptosphaerulina trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), Powdery Mildew (Phyllosticta sojaecola) Micros
  • Black Root Red (Calonectria crotalariae), Charcoal Red (Macrophomina phaseolina), Fusarium Blight or Wiit, Root Red, and Pod and Collar Red (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Red (Mycoleptodiscus terrestris), Neocosmospora (Neocosmopspora vasinfecta), Pod and Star Blight (Diaporthe phaseolorum), Stem Canker (Diaporthe phaseolorum var.
  • Phytophthora red (Phytophthora megasperma), Brown Stem Red (Phialophora gregata), Pythium Red (Pythium aphanidermatum, Pythium irregular, Pythium Debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • the active compound combinations according to the invention can be used particularly successfully for combating cereal diseases, such as, for example, against Puccinia species and diseases in wine, fruit and vegetable crops, such as against Botrytis, Venturia or Alternaria species.
  • the active compound combinations according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus fumigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means a limitation
  • the active compound combinations according to the invention also have very good insecticidal effects. They have a very broad insecticidal activity spectrum, in particular against the following animal pests:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Epitrimerus pyri Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Ceuthorhynchus spp. Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Mono

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AU2009342807A1 (en) 2011-10-13
KR101647703B1 (ko) 2016-08-11
BRPI0924425A8 (pt) 2016-06-21
EA020314B9 (ru) 2015-03-31
WO2010108507A8 (de) 2011-09-29
US9012360B2 (en) 2015-04-21
UA104887C2 (uk) 2014-03-25
CN102365018B (zh) 2014-10-29
WO2010108507A2 (de) 2010-09-30
BRPI0924425A2 (pt) 2015-08-11
WO2010108507A3 (de) 2011-05-05
ZA201106930B (en) 2012-12-27
KR20140014357A (ko) 2014-02-06
EA020314B1 (ru) 2014-10-30
AU2009342807B2 (en) 2015-04-02
EA201171136A1 (ru) 2012-05-30
BRPI0924425B1 (pt) 2017-05-16
US20120035050A1 (en) 2012-02-09
CN102365018A (zh) 2012-02-29

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