JP2008517965A5 - - Google Patents
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- Publication number
- JP2008517965A5 JP2008517965A5 JP2007538323A JP2007538323A JP2008517965A5 JP 2008517965 A5 JP2008517965 A5 JP 2008517965A5 JP 2007538323 A JP2007538323 A JP 2007538323A JP 2007538323 A JP2007538323 A JP 2007538323A JP 2008517965 A5 JP2008517965 A5 JP 2008517965A5
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazepine
- process according
- alkyl
- hydrogen
- reaction mixture
- 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
- 238000000034 method Methods 0.000 claims 24
- NNHCFSLBNPIGQO-UHFFFAOYSA-N 1,4,5-oxadiazepine Chemical class O1C=CN=NC=C1 NNHCFSLBNPIGQO-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 239000002585 base Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 239000011541 reaction mixture Substances 0.000 claims 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000002798 polar solvent Substances 0.000 claims 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 239000003849 aromatic solvent Substances 0.000 claims 3
- 238000009835 boiling Methods 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000004009 herbicide Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 229940117389 dichlorobenzene Drugs 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- -1 phenyl radicals Chemical class 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17762004 | 2004-10-27 | ||
| CH1776/04 | 2004-10-27 | ||
| PCT/EP2005/011432 WO2006045587A1 (en) | 2004-10-27 | 2005-10-25 | A process for the preparation of [1,4,5]-oxadiazepine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008517965A JP2008517965A (ja) | 2008-05-29 |
| JP2008517965A5 true JP2008517965A5 (enExample) | 2011-09-08 |
| JP5117858B2 JP5117858B2 (ja) | 2013-01-16 |
Family
ID=35708855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007538323A Expired - Lifetime JP5117858B2 (ja) | 2004-10-27 | 2005-10-25 | １，４，５−オキサジアゼパン誘導体の調製方法 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20090124800A1 (enExample) |
| EP (1) | EP1838683B1 (enExample) |
| JP (1) | JP5117858B2 (enExample) |
| KR (1) | KR101317353B1 (enExample) |
| CN (2) | CN101039926B (enExample) |
| AR (1) | AR051341A1 (enExample) |
| AT (1) | ATE430140T1 (enExample) |
| BR (1) | BRPI0517390B8 (enExample) |
| CA (1) | CA2579742C (enExample) |
| DE (1) | DE602005014280D1 (enExample) |
| DK (1) | DK1838683T3 (enExample) |
| EA (1) | EA011555B1 (enExample) |
| ES (1) | ES2325382T3 (enExample) |
| IL (1) | IL181766A (enExample) |
| MX (1) | MX2007004591A (enExample) |
| PT (1) | PT1838683E (enExample) |
| TW (1) | TWI382021B (enExample) |
| UA (1) | UA87710C2 (enExample) |
| WO (1) | WO2006045587A1 (enExample) |
| ZA (1) | ZA200701997B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI316939B (en) * | 2001-12-18 | 2009-11-11 | Syngenta Participations Ag | Process for the preparation of organic compounds |
| AR087008A1 (es) | 2011-06-22 | 2014-02-05 | Syngenta Participations Ag | Derivados de n-oxi-pirazolo-triazepina-diona |
| CN104974106B (zh) * | 2014-04-04 | 2019-02-22 | 浙江普洛康裕制药有限公司 | 5-烷基-[1,3,4]-噁二唑-2-甲酸烷基酯的合成方法 |
| CN108264493B (zh) * | 2016-12-30 | 2022-09-30 | 泸州东方农化有限公司 | 一种制备氧二氮杂环化合物的工艺及其应用 |
| WO2018120093A1 (zh) * | 2016-12-30 | 2018-07-05 | 泸州东方农化有限公司 | 一种制备氧二氮杂环化合物的工艺及其应用 |
| CN108264492B (zh) * | 2016-12-30 | 2020-04-14 | 浙江省诸暨合力化学对外贸易有限公司 | 一种氧二氮杂环化合物的制备工艺及应用 |
| CN111386274B (zh) | 2017-12-05 | 2023-07-21 | 先正达参股股份有限公司 | 用于合成除草剂吡唑烷二酮化合物的化学方法 |
| CN112522340B (zh) * | 2019-09-19 | 2023-05-09 | 四川利尔生物科技有限公司 | 酶催化水解制备1-氧-4,5-二氮杂环庚烷的方法 |
| GB202206290D0 (en) * | 2022-04-29 | 2022-06-15 | Syngenta Crop Protection Ag | Process |
| CN119118946A (zh) * | 2023-06-13 | 2024-12-13 | 南京理工大学 | 一种安全高效制备[1,4,5]氧二氮杂庚烷的方法 |
| WO2025131957A1 (en) | 2023-12-22 | 2025-06-26 | Basf Se | Diazinone compounds for the control of invertebrate pests |
| EP4574819A1 (en) | 2023-12-22 | 2025-06-25 | Basf Se | Diazinone compounds for the control of invertebrate pests |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921068A (en) * | 1957-11-19 | 1960-01-12 | Sterling Drug Inc | Mercurated 1, 6-diazabicyclo[4, 4, o] decane-7, 10-diones |
| JPH1029981A (ja) * | 1996-07-15 | 1998-02-03 | Nippon Hidorajin Kogyo Kk | ヘキサヒドロピリダジン類の製造方法 |
| AU741365B2 (en) * | 1998-03-13 | 2001-11-29 | Syngenta Participations Ag | Herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives |
| PT1209972E (pt) * | 1999-09-07 | 2003-10-31 | Syngenta Participations Ag | Composicao herbicida |
| CA2382432A1 (en) * | 1999-09-07 | 2001-03-15 | Thomas Maetzke | Novel herbicides |
| TWI316939B (en) * | 2001-12-18 | 2009-11-11 | Syngenta Participations Ag | Process for the preparation of organic compounds |
-
2005
- 2005-10-25 BR BRPI0517390A patent/BRPI0517390B8/pt active IP Right Grant
- 2005-10-25 UA UAA200705420A patent/UA87710C2/ru unknown
- 2005-10-25 TW TW094137257A patent/TWI382021B/zh active
- 2005-10-25 DK DK05795620T patent/DK1838683T3/da active
- 2005-10-25 MX MX2007004591A patent/MX2007004591A/es active IP Right Grant
- 2005-10-25 EP EP05795620A patent/EP1838683B1/en not_active Expired - Lifetime
- 2005-10-25 CN CN2005800347444A patent/CN101039926B/zh not_active Expired - Lifetime
- 2005-10-25 EA EA200700766A patent/EA011555B1/ru not_active IP Right Cessation
- 2005-10-25 ES ES05795620T patent/ES2325382T3/es not_active Expired - Lifetime
- 2005-10-25 PT PT05795620T patent/PT1838683E/pt unknown
- 2005-10-25 DE DE602005014280T patent/DE602005014280D1/de not_active Expired - Lifetime
- 2005-10-25 WO PCT/EP2005/011432 patent/WO2006045587A1/en not_active Ceased
- 2005-10-25 US US11/577,805 patent/US20090124800A1/en not_active Abandoned
- 2005-10-25 AR ARP050104463A patent/AR051341A1/es active IP Right Grant
- 2005-10-25 CN CN2010102611497A patent/CN101914072A/zh active Pending
- 2005-10-25 KR KR1020077009539A patent/KR101317353B1/ko not_active Expired - Lifetime
- 2005-10-25 AT AT05795620T patent/ATE430140T1/de active
- 2005-10-25 CA CA2579742A patent/CA2579742C/en not_active Expired - Lifetime
- 2005-10-25 JP JP2007538323A patent/JP5117858B2/ja not_active Expired - Lifetime
-
2007
- 2007-03-07 IL IL181766A patent/IL181766A/en active IP Right Grant
- 2007-03-07 ZA ZA200701997A patent/ZA200701997B/en unknown
-
2011
- 2011-05-04 US US13/100,601 patent/US20110207925A1/en not_active Abandoned
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