JP2010520866A5 - - Google Patents
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- Publication number
- JP2010520866A5 JP2010520866A5 JP2009552127A JP2009552127A JP2010520866A5 JP 2010520866 A5 JP2010520866 A5 JP 2010520866A5 JP 2009552127 A JP2009552127 A JP 2009552127A JP 2009552127 A JP2009552127 A JP 2009552127A JP 2010520866 A5 JP2010520866 A5 JP 2010520866A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- haloalkyl
- halogen
- haloalkoxy
- 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.)
- Granted
Links
- 229910052736 halogen Inorganic materials 0.000 claims description 100
- 150000002367 halogens Chemical class 0.000 claims description 99
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 90
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 87
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- -1 methoxy, ethoxy Chemical group 0.000 claims description 25
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 12
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 12
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 10
- 125000005240 diheteroarylamino group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 16
- 238000000034 method Methods 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 3
- 241000196324 Embryophyta Species 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 2
- 150000001543 aryl boronic acids Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000004969 haloethyl group Chemical group 0.000 claims 2
- 125000004970 halomethyl group Chemical group 0.000 claims 2
- 230000002363 herbicidal effect Effects 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006772 (C1-C6) haloalkylsulfonyloxy group Chemical group 0.000 claims 1
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 244000038559 crop plants Species 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000006410 propenylene group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 1
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0704653.5 | 2007-03-09 | ||
| GBGB0704653.5A GB0704653D0 (en) | 2007-03-09 | 2007-03-09 | Novel herbicides |
| PCT/EP2008/001840 WO2008110307A1 (en) | 2007-03-09 | 2008-03-07 | 2-aryl-5-heterocyclyl-cyclohexane-1,3-dione compounds and their use as herbicides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010520866A JP2010520866A (ja) | 2010-06-17 |
| JP2010520866A5 true JP2010520866A5 (OSRAM) | 2013-09-19 |
| JP5457200B2 JP5457200B2 (ja) | 2014-04-02 |
Family
ID=37988740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009552127A Expired - Fee Related JP5457200B2 (ja) | 2007-03-09 | 2008-03-07 | ２−アリール−ヘテロシクリル−シクロヘキサン−１，３−ジオン化合物及び除草剤としてのこれらの使用 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8536351B2 (OSRAM) |
| EP (1) | EP2134699B1 (OSRAM) |
| JP (1) | JP5457200B2 (OSRAM) |
| KR (1) | KR20090119991A (OSRAM) |
| CN (1) | CN101730688B (OSRAM) |
| AR (1) | AR065649A1 (OSRAM) |
| AT (1) | ATE509016T1 (OSRAM) |
| AU (1) | AU2008226073B2 (OSRAM) |
| BR (1) | BRPI0808683B1 (OSRAM) |
| CA (1) | CA2679343C (OSRAM) |
| CO (1) | CO6210770A2 (OSRAM) |
| DK (1) | DK2134699T3 (OSRAM) |
| ES (1) | ES2366596T3 (OSRAM) |
| GB (1) | GB0704653D0 (OSRAM) |
| HR (1) | HRP20110592T1 (OSRAM) |
| PL (1) | PL2134699T3 (OSRAM) |
| PT (1) | PT2134699E (OSRAM) |
| RU (1) | RU2009136668A (OSRAM) |
| WO (1) | WO2008110307A1 (OSRAM) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY152503A (en) | 2006-12-14 | 2014-10-15 | Syngenta Participations Ag | 4-phenyl-pyrane-3, 5-diones, 4-phenyl-thiopyrane-3, 5-diones and cyclohexanetriones as novel herbicides |
| GB0704652D0 (en) | 2007-03-09 | 2007-04-18 | Syngenta Participations Ag | Novel herbicides |
| GB0710223D0 (en) | 2007-05-29 | 2007-07-11 | Syngenta Ltd | Novel Herbicides |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| GB0714981D0 (en) | 2007-08-01 | 2007-09-12 | Syngenta Ltd | Novel herbicides |
| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| MX2010006279A (es) | 2007-12-13 | 2010-06-23 | Syngenta Ltd | 4-fenilpiran-3,5-dionas, 4-feniltiopiran-3,5-dionas y 2-fenil de ciclohexan-1,3,5-trionas como herbicidas. |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| GB0819205D0 (en) * | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
| GB0822834D0 (en) | 2008-12-15 | 2009-01-21 | Syngenta Ltd | Novel herbicides |
| GB0900641D0 (en) | 2009-01-15 | 2009-02-25 | Syngenta Ltd | Novel herbicides |
| WO2010081687A1 (en) * | 2009-01-19 | 2010-07-22 | Bayer Cropscience Ag | Use of 2-aryl-5-heterocyclyl-cyclohexane-l,3-dione compounds as insecticides, acaricides and / or fungicides |
| GB0901086D0 (en) | 2009-01-22 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| BRPI1008949B1 (pt) * | 2009-03-11 | 2018-07-10 | Bayer Intellectual Property Gmbh | Cetoenóis haloalquilmetilenóxi-fenil-substituídos e seu uso, composição, seu uso e seu método de produção, métodos para combate de pestes animais e/ou crescimento de plantas indesejadas |
| CN102471206B (zh) * | 2009-07-17 | 2014-08-20 | 辛根塔有限公司 | 除草剂 |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| US20130210625A1 (en) * | 2010-05-31 | 2013-08-15 | Syngenta Crop Protection Llc | Spiroheterocyclic pyrrolidine derivatives based pesticides |
| BR112014017239B1 (pt) | 2012-01-26 | 2019-05-14 | Bayer Intelectual Property Gmbh | Uso de compostos cetoenóis para o controle de parasitas em peixes |
| PL2935230T3 (pl) * | 2012-12-21 | 2018-07-31 | Syngenta Limited | Herbicydowo aktywne cykliczne związki dionowe, lub ich pochodne, podstawione fenylem, który ma podstawnik zawierający alkinyl |
| US10590143B2 (en) * | 2013-05-30 | 2020-03-17 | Syngenta Limited | Herbicidally active (alkynyl-phenyl)-substituted cyclic dione compounds and derivatives thereof |
| GB201411418D0 (en) * | 2014-06-26 | 2014-08-13 | Syngenta Participations Ag | Compounds |
| CN110734386A (zh) * | 2019-10-28 | 2020-01-31 | 新乡市锦源化工有限公司 | 一种对氨基乙酰苯胺的制备方法 |
| CN113121341A (zh) * | 2019-12-31 | 2021-07-16 | 江苏中旗科技股份有限公司 | 一种合成2,6-二乙基-4-甲基苯乙酸酯的方法 |
| CN113754613B (zh) * | 2021-09-27 | 2023-06-30 | 北京工商大学 | 一种4-烯醇的苯硫基环醚化方法 |
| CN115819228A (zh) * | 2022-11-29 | 2023-03-21 | 南方医科大学 | 一种2-芳基-2-环己二酮烯醇酯类化合物的合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4659372A (en) | 1977-03-28 | 1987-04-21 | Union Carbide Corporation | Biocidal 2-aryl-1,3-cyclohexanedione enol ester compounds |
| US4256659A (en) * | 1977-03-28 | 1981-03-17 | Union Carbide Corporation | Method of preparing 2-aryl-1,3-cyclohexanedione compounds |
| US4409153A (en) * | 1980-03-28 | 1983-10-11 | Union Carbide Corporation | O-(2-Aryl-3-oxo-1-cyclohexenyl) phosphates |
| US4351666A (en) * | 1980-06-27 | 1982-09-28 | Union Carbide Corporation | Enol derivatives of 2-aryl-1,3-cyclohexanedione compound as sugar enhancer for plants |
| ZW12488A1 (en) * | 1987-09-25 | 1988-11-23 | Chevron Res | 2-/1-(5-halothienylmethoxyimino)ethyl/-3-hydroxy-5-(tetrahydro-2h-thiopyranyl)-cyclohex-2-en-1-one and derivatives thereof and their use as selective herbicides and to control lateral buds in tobacco plants |
| JPH02726A (ja) * | 1987-11-28 | 1990-01-05 | Nippon Soda Co Ltd | シクロヘキセノン誘導体、その製造方法及び除草剤 |
| ATE109458T1 (de) * | 1990-10-19 | 1994-08-15 | Basf Ag | Ungesättigte cyclohexenonoximether. |
| DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
-
2007
- 2007-03-09 GB GBGB0704653.5A patent/GB0704653D0/en not_active Ceased
-
2008
- 2008-03-07 EP EP08716354A patent/EP2134699B1/en not_active Not-in-force
- 2008-03-07 HR HR20110592T patent/HRP20110592T1/hr unknown
- 2008-03-07 WO PCT/EP2008/001840 patent/WO2008110307A1/en not_active Ceased
- 2008-03-07 CN CN2008800137859A patent/CN101730688B/zh not_active Expired - Fee Related
- 2008-03-07 AR ARP080100955A patent/AR065649A1/es active IP Right Grant
- 2008-03-07 DK DK08716354.9T patent/DK2134699T3/da active
- 2008-03-07 PT PT08716354T patent/PT2134699E/pt unknown
- 2008-03-07 JP JP2009552127A patent/JP5457200B2/ja not_active Expired - Fee Related
- 2008-03-07 AT AT08716354T patent/ATE509016T1/de active
- 2008-03-07 CA CA2679343A patent/CA2679343C/en not_active Expired - Fee Related
- 2008-03-07 KR KR1020097021081A patent/KR20090119991A/ko not_active Withdrawn
- 2008-03-07 BR BRPI0808683A patent/BRPI0808683B1/pt not_active IP Right Cessation
- 2008-03-07 US US12/530,476 patent/US8536351B2/en not_active Expired - Fee Related
- 2008-03-07 AU AU2008226073A patent/AU2008226073B2/en not_active Ceased
- 2008-03-07 PL PL08716354T patent/PL2134699T3/pl unknown
- 2008-03-07 ES ES08716354T patent/ES2366596T3/es active Active
- 2008-03-07 RU RU2009136668/04A patent/RU2009136668A/ru not_active Application Discontinuation
-
2009
- 2009-09-07 CO CO09095057A patent/CO6210770A2/es not_active Application Discontinuation
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