ZA200405643B - Bicyclic fused pyridinyl amides and advantageous compositions thereof for use as fungicidal. - Google Patents

Info

Publication number

ZA200405643B

ZA200405643B ZA200405643A ZA200405643A ZA200405643B ZA 200405643 B ZA200405643 B ZA 200405643B ZA 200405643 A ZA200405643 A ZA 200405643A ZA 200405643 A ZA200405643 A ZA 200405643A ZA 200405643 B ZA200405643 B ZA 200405643B

Authority

ZA

South Africa

Prior art keywords

compound

halogen

group

component

compounds

Prior art date

2002-03-19

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• 239000000203 mixture Substances 0.000 title claims description 111
• 230000000855 fungicidal effect Effects 0.000 title claims description 9
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical class NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 title description 3
• 125000002619 bicyclic group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 229
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 71
• 239000000417 fungicide Substances 0.000 claims description 48
• -1 3-bromo-N-[1 -(3-bromo-3-chloro-2-pyridinyl)ethyl]-4-isoquinolinecarboxamide Chemical compound 0.000 claims description 46
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 38
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 201000010099 disease Diseases 0.000 claims description 27
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 27
• 125000001188 haloalkyl group Chemical group 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 19
• XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 239000005756 Cymoxanil Substances 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 238000000034 method Methods 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 16
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
• 229930182558 Sterol Natural products 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 150000003432 sterols Chemical class 0.000 claims description 15
• 235000003702 sterols Nutrition 0.000 claims description 15
• 125000004414 alkyl thio group Chemical group 0.000 claims description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
• 150000001204 N-oxides Chemical class 0.000 claims description 10
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 10
• 239000007787 solid Substances 0.000 claims description 10
• 239000004094 surface-active agent Substances 0.000 claims description 10
• YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 230000006696 biosynthetic metabolic pathway Effects 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 9
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 9
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 9
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 150000003839 salts Chemical class 0.000 claims description 8
• 102000004190 Enzymes Human genes 0.000 claims description 7
• 108090000790 Enzymes Proteins 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
• 125000002837 carbocyclic group Chemical group 0.000 claims description 7
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
• 239000007788 liquid Substances 0.000 claims description 7
• 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 claims description 6
• 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 claims description 6
• DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
• 239000012990 dithiocarbamate Substances 0.000 claims description 6
• 244000000004 fungal plant pathogen Species 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 150000003053 piperidines Chemical class 0.000 claims description 5
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
• 230000002538 fungal effect Effects 0.000 claims description 4
• 230000027756 respiratory electron transport chain Effects 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 230000002438 mitochondrial effect Effects 0.000 claims description 3
• 125000005543 phthalimide group Chemical class 0.000 claims description 3
• 230000000241 respiratory effect Effects 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• BBCAHRBPRAIHNL-UHFFFAOYSA-N 2,4-dichloro-n-[[3-chloro-5-(trifluoromethyl)pyridin-2-yl]methyl]-5,6,7,8-tetrahydroquinoline-3-carboxamide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)N=C(CCCC2)C2=C1Cl BBCAHRBPRAIHNL-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 239000000460 chlorine Substances 0.000 description 83
• 229940126214 compound 3 Drugs 0.000 description 40
• 229940125898 compound 5 Drugs 0.000 description 40
• 238000012360 testing method Methods 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 21
• 241000196324 Embryophyta Species 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• 239000005802 Mancozeb Substances 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 13
• 239000005772 Famoxadone Substances 0.000 description 13
• 239000005807 Metalaxyl Substances 0.000 description 13
• ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 13
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 12
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• 239000005789 Folpet Substances 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 12
• YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 12
• 229920000940 maneb Polymers 0.000 description 12
• 239000005730 Azoxystrobin Substances 0.000 description 11
• 239000005857 Trifloxystrobin Substances 0.000 description 11
• WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 11
• ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• 239000005823 Propineb Substances 0.000 description 10
• 239000005869 Pyraclostrobin Substances 0.000 description 10
• 239000011717 all-trans-retinol Substances 0.000 description 10
• 235000019169 all-trans-retinol Nutrition 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 10
• HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 10
• 239000005774 Fenamidone Substances 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 description 9
• 239000003112 inhibitor Substances 0.000 description 9
• UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 8
• 239000005745 Captan Substances 0.000 description 8
• 239000005800 Kresoxim-methyl Substances 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 241000233622 Phytophthora infestans Species 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 229940117949 captan Drugs 0.000 description 8
• ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 239000005734 Benalaxyl Substances 0.000 description 7
• 239000012677 causal agent Substances 0.000 description 7
• 239000008187 granular material Substances 0.000 description 7
• CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 6
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 6
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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• 102100038239 Protein Churchill Human genes 0.000 description 6
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• 230000001276 controlling effect Effects 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 230000006540 mitochondrial respiration Effects 0.000 description 6
• FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
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• 240000003768 Solanum lycopersicum Species 0.000 description 5
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• 229930182692 Strobilurin Natural products 0.000 description 5
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• 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 239000001257 hydrogen Substances 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
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• IXRUZEMDNAMNFO-UHFFFAOYSA-N 6-chloro-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4-one Chemical compound O=C1N(CCC)C(OCCC)=NC2=C1C=C(Cl)S2 IXRUZEMDNAMNFO-UHFFFAOYSA-N 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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• 239000005750 Copper hydroxide Substances 0.000 description 4
• 241000233866 Fungi Species 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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• RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 4
• MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
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• 239000003153 chemical reaction reagent Substances 0.000 description 4
• CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 4
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• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
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• 230000005764 inhibitory process Effects 0.000 description 4
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• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 235000019341 magnesium sulphate Nutrition 0.000 description 4
• 150000002780 morpholines Chemical class 0.000 description 4
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• PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 3
• MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 3
• UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 3
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