AU2004208875B2 - Amino 1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof and their use as herbicides and plant growth regulators - Google Patents
Amino 1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof and their use as herbicides and plant growth regulators Download PDFInfo
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- AU2004208875B2 AU2004208875B2 AU2004208875A AU2004208875A AU2004208875B2 AU 2004208875 B2 AU2004208875 B2 AU 2004208875B2 AU 2004208875 A AU2004208875 A AU 2004208875A AU 2004208875 A AU2004208875 A AU 2004208875A AU 2004208875 B2 AU2004208875 B2 AU 2004208875B2
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- Prior art keywords
- direct bond
- formula
- alkyl
- compounds
- methyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 50
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- 238000002360 preparation method Methods 0.000 title claims description 19
- 230000008569 process Effects 0.000 title claims description 19
- 239000005648 plant growth regulator Substances 0.000 title claims description 6
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 254
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- -1 biguanidine compound Chemical class 0.000 claims description 88
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 58
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
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- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000006660 (C3-C4) halocycloalkyl group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- OUZWORPRSQLJNP-UHFFFAOYSA-N carbonocyanidoyl cyanoformate Chemical compound N#CC(=O)OC(=O)C#N OUZWORPRSQLJNP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 150000001721 carbon Chemical group 0.000 description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Priority Applications (1)
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| AU2011201831A AU2011201831B2 (en) | 2003-02-05 | 2011-04-21 | Amino-1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03002438 | 2003-02-05 | ||
| EP03002438.4 | 2003-02-05 | ||
| EP03016680.5 | 2003-08-01 | ||
| EP03016680 | 2003-08-01 | ||
| PCT/EP2004/000538 WO2004069814A1 (en) | 2003-02-05 | 2004-01-23 | Amino 1, 3, 5-triazines n-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof and their use as herbicides and plant growth regulators |
Related Child Applications (1)
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| AU2011201831A Division AU2011201831B2 (en) | 2003-02-05 | 2011-04-21 | Amino-1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators |
Publications (2)
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| AU2004208875A1 AU2004208875A1 (en) | 2004-08-19 |
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| AU2011201831A Expired AU2011201831B2 (en) | 2003-02-05 | 2011-04-21 | Amino-1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators |
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| AU2011201831A Expired AU2011201831B2 (en) | 2003-02-05 | 2011-04-21 | Amino-1, 3, 5-triazines N-substituted with chiral bicyclic radicals, process for their preparation, compositions thereof, and their use as herbicides and plant growth regulators |
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| AR (1) | AR043014A1 (enExample) |
| AU (2) | AU2004208875B2 (enExample) |
| CA (1) | CA2515116C (enExample) |
| CO (1) | CO5590957A2 (enExample) |
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| EP1790227A1 (de) | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Wässrige Suspensionskonzentrate aus 2,4-Diamino-s-triazinherbiziden |
| US7989459B2 (en) * | 2006-02-17 | 2011-08-02 | Pharmacopeia, Llc | Purinones and 1H-imidazopyridinones as PKC-theta inhibitors |
| US20090281075A1 (en) * | 2006-02-17 | 2009-11-12 | Pharmacopeia, Inc. | Isomeric purinones and 1h-imidazopyridinones as pkc-theta inhibitors |
| DE102006016885A1 (de) * | 2006-04-11 | 2007-10-18 | Bayer Cropscience Ag | Mit bicyclischen Radikalen N-substituierte Diamino-1,3,5-triazine, Verfahren für ihre Herstellung, Zubereitungen davon und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE102006016884A1 (de) * | 2006-04-11 | 2007-10-25 | Bayer Cropscience Ag | Substituierte Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| US7915268B2 (en) | 2006-10-04 | 2011-03-29 | Wyeth Llc | 8-substituted 2-(benzimidazolyl)purine derivatives for immunosuppression |
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| DE102006059941A1 (de) | 2006-12-19 | 2008-06-26 | Bayer Cropscience Ag | Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
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| US20110034469A1 (en) | 2009-08-04 | 2011-02-10 | Takeda Pharmaceutical Company Limited | Heterocyclic Compound |
| US9723836B2 (en) * | 2009-11-19 | 2017-08-08 | Bayer Cropscience Ag | Synergistic pre-emergent and post-emergent weed control compositions and methods of use thereof |
| EP2327700A1 (de) | 2009-11-21 | 2011-06-01 | Bayer CropScience AG | Dialkyl-Triazinamine und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums |
| JP6062528B2 (ja) | 2012-03-29 | 2017-01-18 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | ５−アミノピリミジン誘導体及び望ましくない植物の成長を防除するためのそれらの使用 |
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| MX362690B (es) | 2014-01-28 | 2019-02-01 | Bayer Cropscience Ag | Metodo para producir 1-indanoles y 1-indanaminas. |
| BR112017010398A2 (pt) | 2014-11-18 | 2018-01-02 | Bayer Cropscience Ag | utilização de certas combinações de herbicidas em cultivo de plantas com raiz tuberosa |
| JP2018514536A (ja) | 2015-04-27 | 2018-06-07 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | グルホシネートおよびインダジフラムを含む除草剤組み合わせ |
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| BR112018004786B1 (pt) * | 2015-09-11 | 2020-12-08 | Bayer Cropscience Aktiengesellschaft | método para produzir sais de biguanida e s-triazinas |
| US10743540B2 (en) | 2016-06-24 | 2020-08-18 | Bayer Cropscience Aktiengesellschaft | 3-amino-1,2,4-triazine derivatives and their use for controlling undesired plant growth |
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-
2004
- 2004-01-23 KR KR1020127007595A patent/KR101224300B1/ko not_active Expired - Lifetime
- 2004-01-23 MX MXPA05008295A patent/MXPA05008295A/es active IP Right Grant
- 2004-01-23 EP EP04704591.9A patent/EP1592674B1/en not_active Expired - Lifetime
- 2004-01-23 PL PL378410A patent/PL222483B1/pl unknown
- 2004-01-23 PT PT47045919T patent/PT1592674E/pt unknown
- 2004-01-23 CA CA2515116A patent/CA2515116C/en not_active Expired - Lifetime
- 2004-01-23 HR HRP20050702AA patent/HRP20050702B1/hr not_active IP Right Cessation
- 2004-01-23 CN CNB2004800034746A patent/CN100448850C/zh not_active Expired - Lifetime
- 2004-01-23 RS YU20050596A patent/RS53108B/sr unknown
- 2004-01-23 KR KR1020057014463A patent/KR101213248B1/ko not_active Expired - Lifetime
- 2004-01-23 UA UAA200508497A patent/UA81141C2/uk unknown
- 2004-01-23 ES ES04704591.9T patent/ES2466245T3/es not_active Expired - Lifetime
- 2004-01-23 JP JP2006501582A patent/JP4753258B2/ja not_active Expired - Lifetime
- 2004-01-23 DK DK04704591.9T patent/DK1592674T3/da active
- 2004-01-23 OA OA1200500223A patent/OA13024A/en unknown
- 2004-01-23 EA EA200501161A patent/EA012406B1/ru not_active IP Right Cessation
- 2004-01-23 EP EP10185534A patent/EP2305655A3/en not_active Withdrawn
- 2004-01-23 AP AP2005003386A patent/AP1960A/xx active
- 2004-01-23 WO PCT/EP2004/000538 patent/WO2004069814A1/en not_active Ceased
- 2004-01-23 AU AU2004208875A patent/AU2004208875B2/en not_active Expired
- 2004-02-03 US US10/771,649 patent/US8114991B2/en not_active Expired - Lifetime
- 2004-02-03 TW TW093102423A patent/TWI357411B/zh not_active IP Right Cessation
- 2004-02-03 AR ARP040100332A patent/AR043014A1/es not_active Application Discontinuation
- 2004-02-03 TW TW100101093A patent/TWI391094B/zh not_active IP Right Cessation
- 2004-02-05 MY MYPI20040350A patent/MY140171A/en unknown
-
2005
- 2005-07-13 ZA ZA200505626A patent/ZA200505626B/xx unknown
- 2005-07-22 CR CR7920A patent/CR7920A/es unknown
- 2005-07-25 IL IL169877A patent/IL169877A/en active IP Right Grant
- 2005-07-27 EC EC2005005934A patent/ECSP055934A/es unknown
- 2005-08-03 CO CO05076616A patent/CO5590957A2/es not_active Application Discontinuation
-
2010
- 2010-09-30 JP JP2010220690A patent/JP2011037870A/ja active Pending
-
2011
- 2011-04-21 AU AU2011201831A patent/AU2011201831B2/en not_active Expired
- 2011-12-28 US US13/338,351 patent/US20120101287A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0864567A1 (en) * | 1995-11-27 | 1998-09-16 | Idemitsu Kosan Company Limited | Triazine derivatives |
| AU714187B2 (en) * | 1996-02-28 | 1999-12-23 | Bayer Intellectual Property Gmbh | 2-amino-4-bicycloamino-1,3,5-triazines as herbicides and plant growth regulators |
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