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DK2763993T3 - Heterocyclylpyri(mi)dinylpyrazol - Google Patents

Heterocyclylpyri(mi)dinylpyrazol Download PDF

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Publication number
DK2763993T3
DK2763993T3 DK12766993.5T DK12766993T DK2763993T3 DK 2763993 T3 DK2763993 T3 DK 2763993T3 DK 12766993 T DK12766993 T DK 12766993T DK 2763993 T3 DK2763993 T3 DK 2763993T3
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Denmark
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butyl
plants
iso
methyl
propyl
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DK12766993.5T
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Hendrik Helmke
Stefan Hillebrand
Amos Mattes
Lars Rodefeld
Pierre Wasnaire
Jürgen Benting
Peter Dahmen
Ulrike Wachendorff-Neumann
Philippe Desbordes
Anne-Sophie Rebstock
Alexander Sudau
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Bayer Ip Gmbh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (8)

1. Heterocyclylpyri(mi)dinylpyrazol med formel (I)
hvori U er strukturer med den qenerelle formel
X1 er C-H, X2 er S eller 0, W er C, N, son hver eventuelt er substitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, eller er 0, a, b er en enkelt- eller dobbeltbinding, med det forbehold at "a" og "b" er en enkeltbinding, hvis W er lig med 0, og "a" er en enkeltbinding, hvis Q er lig med C=C, n er 0, 1, 2, 3 eller 4, Q er C, C-C, C=C eller C-C-C, som hver eventuelt er monoeller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, R1 er C (0) OR7, C(0)SR7, C(S)0R7, C(0)R7, C(S)R7, C(0)NR7R8, C (S) NR7R8, C (=NR9) R10, C(=NR9)OR10, C (=NRS) NR9R10, SO(=NR9)R10, S02NR7R8, so2r7 eller er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH2CH=CH2, -C^CH, C=CCH3, -CH2C^CH, C6-Ci4-aryl, Cf-Cg-heterocyclyl, C2-C9- heteroaryl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R11, R2 er C (0) OR7, C (0) SR7, C(S)0R7, C(0)R7, C(S)R7 eller er Ci-C6-alkyl, C3-C8-cycloalkyl, C2-Ce-alkenyl, C2-C8- alkynyl, C6-Ci4-aryl, C2-C9-heterocyclyl, C2-Cg-heteroaryl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R11, med det forbehold at R1 ikke er Ci-C6~alkyl, Cs-Cs-cycloalkyl, Ci-C6-halogenalkyl, C3-C8-halogencycloalkyl, Ci-C4-alkoxy-Cl-C6-alkyl eller amino-Ci-C6-alkyl, hvis R2 er Ci-C6-alkyl, C3-C8-cycloalkyl, Ci-C6-halogenalkyl, C3-C8-halogencycloalkyl, C1-C4- alkoxy-Ci-C6-alkyl eller amino-Ci-C6-alkyl, og omvendt, R3 og R4 uafhængigt af hinanden er H, F, Cl, Br, I, cyano eller er methyl, ethyl, cyclopropyl, -CH=CH2, -CH2CH=CH2, CH2C=CH , -C=CH, phenyl, methoxy, som hver eventuelt er monoeller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R11, R5 som substituent for C er: H, cyano, halogen, OH, =0, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH2CH=CH2, -C=CH, -C=CCH3, -CH2C=CH, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, -0-CH2C^CH, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af OH, F, Cl, cyano, eller er C(0)NR9R10, C(0)R9, C(0)0R9, S(0)2R9, C(S)NR9R10, C(S)R9, S(0)2R9R10, =N(0R9), og som substituent for N er: H, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH2CH=CH2, - C^CH, -C^CCHa, -CH2C=CH, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af OH, F, Cl, cyano, eller er C(0)NR9R10, C(0)R9, C(0)0R9, S(0)2R9, C(S)NR9R10, C(S)R9, S (0) 2NR9R10, R5 er H, Cl, F, cyano eller er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, CH=CH2, -CH2CH=CH2, CH2C=CH, —C=CH, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, iso- propylthio, tertbutylthio, n-butylthio, sec-butylthio, iso-butylthio, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R11, R7 og R8 er H, C(S)R12, C(0)R12, S02R12, C(0)0R12, OR12 eller C (0) NR12R13 eller er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, CH=CH2, -CH2CH=CH2, -CH2C=CH, -C=CH, phenyl, naphthalenyl, benzyl, phenethyl, phenoxymethyl, pyridinyl, pyrazinyl, pyrimidinyl, furanyl, thienyl, thietanyl, oxetanyl, pyrazolyl, imidazolyl, tetrahydrofuranyl, tetrahydropyranyl, morpholinyl, pyrrolidinyl, piperidinyl, indanyl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af F, Cl, Br, OH, =0, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, eller methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, methylsulfanyl, nitro, trifluormethyl, difluormethyl, acetyl, methoxycarbonyl, ethoxycarbonyl, 0-C(0)R9, R9 og R10 er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH=CH2, -CH2CH=CH2, CH2C^CH, -C^CH, phenyl, benzyl, phenethyl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af F, Cl, Br, I, OH, carbonyl, cyano, eller er H, R11 er OH, =0, F, Cl, Br, I, cyano, NH-C(0)R9, NR9R10, C(0)R9, C (0) OR9, C (0) NR9R13, S02R9, 0C(0)R9 eller er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH=CH2, -CH2CH=CH2, CH2C^CH, -C=CH, phenyl, methoxy, ethoxy, tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3- isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-iso-thiazolidinyl, 3- pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2- oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4- isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 2-piperazinyl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, lH-pyrrol-l-yl, lH-pyrrol-2-yl, lH-pyrrol-3-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5- yl, pyrazol-l-yl, pyrazol-3-yl, pyrazol-4-yl, imidazol-l-yl, imidazol-2-yl, imidazol-4-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af F, Cl, Br, I, OH, carbonyl, cyano, methyl, ethyl, methoxy, R12 og R13 er H eller er methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, -CH=CH2, -CH2CH=CH2, CH2C=CH, -C=CH, phenyl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af F, Cl, Br, I, OH, carbonyl, cyano, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl eller methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, tert-butoxy, og endvidere agrokemisk aktive salte deraf.
2. Heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge krav 1, hvor U er strukturer med den generelle formel
X1 er C-H, X2 er S eller 0, W er C, N, som hver eventuelt er substitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, eller er 0, a, b er en enkelt- eller dobbeltbinding, med det forbehold at "a" og "b" er en enkeltbinding, hvis W er lig med 0, og "a" er en enkeltbinding, hvis Q er lig med C=C, n er 0, 1, 2, 3 eller 4, Q er C, C-C eller C=C, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, R1 og R2 uafhængigt af hinanden er formamido, formyl, acetyl, n-propionyl, isobutyryl, 2-methylbutanoyl, 3-methylbutanoyl, 3.3- dimethylbutanoyl, methoxyacetyl, (2-methoxyethoxy)acetyl, 3.3.3- trifluorpropanoyl, cyanoacetyl, lactoyl, 2-hydroxy-2- methylpropanoyl, (methylsulfanyl)acetyl, 2 — (4 — chlorphenoxy)propanoyl, phenylacetyl, 2-phenylpropanoyl, 2 — (4 — fluorphenyl)propanoyl, 2-fluorphenyl)propanoyl, 3- phenylpropanoyl, 3-(4-chlorphenyl)propanoyl, 2 — (4 — fluorphenyl)propanoyl, 2- (2-fluorphenyl)propanoyl, cyclopentylacetyl, cyclopropylacetyl, cyclopropylcarbonyl, (1- methylcyclopropyl) carbonyl, (2-methylcyclopropyl) carbonyl, (1- chlorcyclopropyl)carbonyl, cyclobutylcarbonyl, 2,3-dihydro-lH- inden-2-ylcarbonyl, (2-phenylcyclopropyl)carbonyl, methacryloyl, 3-methylbut-2-enoyl, 4-methylpent-3-enoyl, benzoyl, 4-fluorbenzoyl, 3-thienylcarbonyl, 2-thienylcarbonyl, tetrahydrofuran-2-ylcarbonyl, tetrahydrofuran-3-ylcarbonyl, tetrahydro-2H-pyran-4-ylcarbonyl, tetrahydro-2H-pyran-3- ylcarbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, tert-butoxycarbonyl, 1- cyc1opropy1cyclopropylcarbonyl, cyclopentylcarbonyl, trifluoracetyl, difluoracetyl, 1,3-dithiolan-2-ylcarbonyl, 2- fluor-2-methylpropanoyl, 2-fluorpropanoyl, 2-fluor-2- methylpropanoyl, 2-fluorpropanoyl, 5-oxohexanoyl, (4- oxocyclohexyl)carbonyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, propoxycarbonyl, sec-butoxycarbonyl, R3 er H, F, Cl, methyl, R4 er H, F, Cl, methyl, R5 som substituent for C er: H, cyano, F, OH, =0, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, cyclopropyl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af OH, F, Cl, cyano, og som substituent for N er: H, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af OH, F, Cl, cyano, eller er acetyl, propionyl, isobutyryl, methoxycarbonyl, ethoxycarbonyl, methylcarbamoyl, dimethylcarbamoyl, diethylcarbamoyl, methylsulfonyl, ethylsulfonyl, R5 er H, Cl, F, methyl, ethyl, cyano, difluormethyl, trifluormethyl, og endvidere agrokemisk aktive salte deraf.
3. Heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 2, hvor U er strukturer med den generelle formel
X1 er C-H, W er C, som eventuelt er substitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, a og b er en enkeltbinding, n er 0, 1 eller 2, Q er C eller C-C, som hver eventuelt er mono- eller polysubstitueret med identiske eller forskellige substituenter fra gruppen, der består af R5, R1 og R2 uafhængigt af hinanden er acetyl, n-propionyl, isobutyryl, 2-methylbutanoyl, 3-methylbutanoyl, lactoyl, phenylacetyl, cyclopropylacetyl, cyclopropylcarbonyl, (2- methylcyclopropyl)carbonyl, cyclobutylcarbonyl, benzoyl, 3-thienylcarbonyl, 2-thienylcarbonyl, tetrahydrofuran-3- ylcarbonyl, 3,3,3-trifluorpropanoyl, tetrahydro-2H-pyran-4- ylcarbonyl, 3-phenylpropanoyl, 2-phenylpropanoyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, propoxycarbonyl, sec-butoxycarbonyl, R3 er H, R4 er H, F, R5 er H, cyano, F, OH, =0, methyl, ethyl, n-propyl, cyclopropyl, halogenalkyl, cyanoalkyl, R5 er H, F, og endvidere agrokemisk aktive salte deraf.
4. Sammensætning til bekæmpelse af fytopatogene, skadelige og mykotoksindannende svampe i og/eller på planter eller i og/eller på frø fra planter, der er kendetegnet ved, at den omfatter mindst én heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 3 foruden fyldstoffer og/eller overfladeaktive stoffer.
5. Anvendelse af heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 3 til bekæmpelse af uønskede mikroorganismer i og/eller på planter eller i og/eller på frø fra planter.
6. Fremgangsmåde til bekæmpelse af fytopatogene, skadelige og mykotoksindannende svampe i og/eller på planter eller i og/eller på frø fra planter, der er kendetegnet ved, at heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 3 påføres mikroorganismerne og/eller deres habitat.
7. Fremgangsmåde til fremstilling af sammensætninger til bekæmpelse af uønskede mikroorganismer, der er kendetegnet ved, at en heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 3 blandes med fyldstoffer og/eller overfladeaktive stoffer.
8. Anvendelse af en heterocyclylpyri(mi)dinylpyrazol med formel (I) ifølge et hvilket som helst af kravene 1 til 3 til behandling af transgene planter.
DK12766993.5T 2011-10-06 2012-10-04 Heterocyclylpyri(mi)dinylpyrazol DK2763993T3 (da)

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