EP1144380A4 - A meta-nitro phenol derivative and a process for producing it - Google Patents
A meta-nitro phenol derivative and a process for producing itInfo
- Publication number
- EP1144380A4 EP1144380A4 EP99965757A EP99965757A EP1144380A4 EP 1144380 A4 EP1144380 A4 EP 1144380A4 EP 99965757 A EP99965757 A EP 99965757A EP 99965757 A EP99965757 A EP 99965757A EP 1144380 A4 EP1144380 A4 EP 1144380A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- halogen
- cyano
- 6haloalkyl
- compound
- formula
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur 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
- C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/08—Six-membered rings
Definitions
- One aspect of the present invention is a meta-nitro phenol derivative of the formula (I):
- Halogenation reaction can be carried out by reacting the starting compound with a halogenating agent such as N-chlorosuccinimide, sulfuryl chloride, or chlorine in a solvent in the presence or absence of a dehydrohalogenating agent at a temperature of 10 to 150°C for a period of 1-24 hours.
- a halogenating agent such as N-chlorosuccinimide, sulfuryl chloride, or chlorine
- the amount of halogenating agent and dehydrohalogenating agent may be respectively from 1-4 equivalents and from 0.001 to 1 equivalent to the starting compound.
- the reaction is conducted, if necessary, in the presence of a solvent.
- the solvent may, for example, be a polar solvent such as dimethylsulfoxide, N,N- dimethylformamide or 1,3- ⁇ imethyl-imidazolinone; an aromatic solvent such as toluene, xylene or pyridine; an ethers such as tetrahydrofuran or dioxane.
- the reaction is preferably conducted in the presence of a catalyst, which increases the yield.
- the catalyst may, for example, be an alkali halide such as potassium iodide, potassium bromide or potassium chloride; a cuprous halide such as cuprous iodide, cuprous bromide or cuprous chloride; cupric halide such as cupric iodide, cupric bromide or cupric chloride; copper metal.
- an alkali halide such as potassium iodide, potassium bromide or potassium chloride
- a cuprous halide such as cuprous iodide, cuprous bromide or cuprous chloride
- cupric halide such as cupric iodide, cupric bromide or cupric chloride
- copper metal such as copper metal.
- the reaction is conducted, if necessary, under an azeotropic distillation.
- the reaction temperature is usually from 0 to 350°C, preferably from 100 to 200°C.
- the reaction time is usually from 1 to 12 hours.
- Iron powder (6.79 g) was added to a solution of 2-(2-chloro-4-fluoro-5- nitrophenoxy)pyrimidine (6.56 g) in acetic acid (70 ml) and the resulting mixture was stirred at room temperature for 3 hours (monitored by TLC).
- the reaction mixture was diluted with ethyl acetate (200 ml), washed with water (100 ml), then saturated sodium chloride solution (50 ml) twice.
- the aqueous phase was extracted with ethyl acetate (100 ml).
- the ethyl acetate extract was washed with saturated sodium chloride (20 ml) twice.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US281067 | 1994-07-27 | ||
US20318098A | 1998-11-30 | 1998-11-30 | |
US203180 | 1998-11-30 | ||
US28106799A | 1999-03-09 | 1999-03-09 | |
US42600099A | 1999-10-25 | 1999-10-25 | |
US426000 | 1999-10-25 | ||
PCT/US1999/026016 WO2000032573A1 (en) | 1998-11-30 | 1999-11-22 | A meta-nitro phenol derivative and a process for producing it |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1144380A1 EP1144380A1 (en) | 2001-10-17 |
EP1144380A4 true EP1144380A4 (en) | 2003-11-26 |
Family
ID=27394520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99965757A Withdrawn EP1144380A4 (en) | 1998-11-30 | 1999-11-22 | A meta-nitro phenol derivative and a process for producing it |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1144380A4 (en) |
JP (1) | JP2003506312A (en) |
CN (1) | CN1376145A (en) |
AU (1) | AU2145500A (en) |
WO (1) | WO2000032573A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL167956A (en) | 2000-02-04 | 2009-02-11 | Sumitomo Chemical Co | Isocyanate compound |
US6613718B2 (en) | 2001-10-01 | 2003-09-02 | Ishihara Sangyo Kaisha, Ltd. | Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them |
CN103265820B (en) * | 2013-05-23 | 2014-07-30 | 大连理工大学 | Method for preparing azo dye with alkalescent arylamine serving as diazotization ingredient |
CN103288763B (en) * | 2013-06-20 | 2015-06-03 | 郑州福源动物药业有限公司 | Industrial production method of 2,6-dichloropyrazine |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5686162A (en) * | 1979-12-17 | 1981-07-13 | Mitsui Toatsu Chem Inc | Pyridyl-2-oxy-benzene derivative |
EP0065374A1 (en) * | 1981-05-18 | 1982-11-24 | Zoecon Corporation | Substituted phosphinates and phosphinothioates and their use for the control of weeds |
EP0071572A2 (en) * | 1981-07-28 | 1983-02-09 | Ciba-Geigy Ag | Derivatives of 2-nitro-4- or-5-pyridyloxy-phenylphosphonic acid, process for their preparation, their use as herbicides and/or regulators of plant growth and/or microbicides, as well as the intermediates used for their preparation, the process for their preparation and their use as herbicides |
US4526608A (en) * | 1982-07-14 | 1985-07-02 | Zoecon Corporation | Certain 2-pyridyloxyphenyl-oximino-ether-carboxylates, herbicidal compositions containing same and their herbicidal method of use |
US4605434A (en) * | 1983-07-20 | 1986-08-12 | Ciba-Geigy Corporation | Herbicidal and plant-growth-regulating (2-nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivatives and compositions |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ188244A (en) * | 1977-09-13 | 1981-04-24 | Ici Australia Ltd | 2-substituted pyrimidines compositions growth regulating processes |
US4326880A (en) * | 1979-08-14 | 1982-04-27 | Ciba-Geigy Corporation | Derivatives of 5-(pyridyl-2-oxy)-2-nitrobenzoic acid, and herbicidal compositions containing them, and herbicidal methods for using same |
DE3173080D1 (en) * | 1980-01-10 | 1986-01-16 | Nyegaard & Co As | Pyrimidine-2-sulphides and their s-oxides for use in medicine, pharmaceutical compositions containing them, processes for their preparation and such compounds when novel per se |
US4371537A (en) * | 1981-08-13 | 1983-02-01 | The Dow Chemical Company | Sulfur-substituted phenoxypyridines having antiviral activity |
US4484941A (en) * | 1981-09-01 | 1984-11-27 | Sumitomo Chemical Company, Limited | Tetrahydrophthalimides, and their production and use as herbicides |
DE3614060A1 (en) * | 1986-04-23 | 1987-10-29 | Schering Ag | PYRIMIDINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS FUNGICIDES |
US4966622A (en) * | 1988-04-12 | 1990-10-30 | Ciba-Geigy Corporation | N-phenyl-N-pyrimidin-2-ylureas |
ID24479A (en) * | 1997-03-14 | 2000-07-20 | Isk Americas Inc | DIARIL ETERS AND THE PROCESS OF MAKING HERBICIDE COMPOSITIONS AND DRYER CONTAINING ETER DIARIL |
-
1999
- 1999-11-22 EP EP99965757A patent/EP1144380A4/en not_active Withdrawn
- 1999-11-22 CN CN 99815841 patent/CN1376145A/en active Pending
- 1999-11-22 JP JP2000585215A patent/JP2003506312A/en active Pending
- 1999-11-22 AU AU21455/00A patent/AU2145500A/en not_active Abandoned
- 1999-11-22 WO PCT/US1999/026016 patent/WO2000032573A1/en not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5686162A (en) * | 1979-12-17 | 1981-07-13 | Mitsui Toatsu Chem Inc | Pyridyl-2-oxy-benzene derivative |
EP0065374A1 (en) * | 1981-05-18 | 1982-11-24 | Zoecon Corporation | Substituted phosphinates and phosphinothioates and their use for the control of weeds |
EP0071572A2 (en) * | 1981-07-28 | 1983-02-09 | Ciba-Geigy Ag | Derivatives of 2-nitro-4- or-5-pyridyloxy-phenylphosphonic acid, process for their preparation, their use as herbicides and/or regulators of plant growth and/or microbicides, as well as the intermediates used for their preparation, the process for their preparation and their use as herbicides |
US4526608A (en) * | 1982-07-14 | 1985-07-02 | Zoecon Corporation | Certain 2-pyridyloxyphenyl-oximino-ether-carboxylates, herbicidal compositions containing same and their herbicidal method of use |
US4605434A (en) * | 1983-07-20 | 1986-08-12 | Ciba-Geigy Corporation | Herbicidal and plant-growth-regulating (2-nitro-5-aryloxy-phenylamino)-alkylphosphine oxide derivatives and compositions |
Non-Patent Citations (2)
Title |
---|
PATENT ABSTRACTS OF JAPAN vol. 005, no. 156 (C - 074) 6 October 1981 (1981-10-06) * |
See also references of WO0032573A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP1144380A1 (en) | 2001-10-17 |
WO2000032573A8 (en) | 2001-09-13 |
CN1376145A (en) | 2002-10-23 |
WO2000032573A1 (en) | 2000-06-08 |
AU2145500A (en) | 2000-06-19 |
JP2003506312A (en) | 2003-02-18 |
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Legal Events
Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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17P | Request for examination filed |
Effective date: 20010608 |
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AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE |
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AX | Request for extension of the european patent |
Free format text: AL;LT;LV;MK;RO;SI |
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RIC1 | Information provided on ipc code assigned before grant |
Ipc: 7C 07D 257/08 B Ipc: 7C 07D 251/30 B Ipc: 7C 07D 241/18 B Ipc: 7C 07D 237/14 B Ipc: 7C 07D 213/64 B Ipc: 7C 07D 239/42 B Ipc: 7C 07D 239/38 B Ipc: 7C 07D 239/34 B Ipc: 7C 07D 213/72 B Ipc: 7C 07D 213/70 B Ipc: 7C 07D 213/63 A |
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A4 | Supplementary search report drawn up and despatched |
Effective date: 20031007 |
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STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
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18W | Application withdrawn |
Effective date: 20031128 |