EP1144380A4 - Derive de meta-nitrophenol et procede de production correspondant - Google Patents

Derive de meta-nitrophenol et procede de production correspondant

Info

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Withdrawn
Application number
EP99965757A
Other languages
German (de)
English (en)
Other versions
EP1144380A1 (fr
Inventor
Bai-Ping Ying
Sandeep Gupta
Masamitsu Tsukamoto
David A Pulman
Takahiro Haga
Masahiko Ikeguchi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Publication of EP1144380A1 publication Critical patent/EP1144380A1/fr
Publication of EP1144380A4 publication Critical patent/EP1144380A4/fr
Withdrawn legal-status Critical Current

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

L'invention concerne un dérivé de méta-nitrophénol représenté par la formule (I) dans laquelle X représente halogène, cyano, nitro, haloalkyle C1-6 ou haloalcoxy C1-6; Y représente hydrogène, halogène, cyano, nitro, haloalcoxy C1-6; Z représente oxygène, soufre ou NR; R représente hydrogène ou alkyle C1-6; Ar représente pyridinyle, pyrimidinyle, pyridazinyle, pyrazinyle, s-triazinyle ou s-tétrazinyle où Ar peut être substitué par au moins un substituant choisi dans le groupe constitué par halogène, cyano, alkyle C1-6, haloalkyle C1-6, alcoxy C1-6, haloalcoxy C1-6, alkylsulfonyle C1-6 et haloalkylsulfonyle C1-6.
EP99965757A 1998-11-30 1999-11-22 Derive de meta-nitrophenol et procede de production correspondant Withdrawn EP1144380A4 (fr)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US20318098A 1998-11-30 1998-11-30
US203180 1998-11-30
US28106799A 1999-03-09 1999-03-09
US281067 1999-03-09
US42600099A 1999-10-25 1999-10-25
US426000 1999-10-25
PCT/US1999/026016 WO2000032573A1 (fr) 1998-11-30 1999-11-22 Derive de meta-nitrophenol et procede de production correspondant

Publications (2)

Publication Number Publication Date
EP1144380A1 EP1144380A1 (fr) 2001-10-17
EP1144380A4 true EP1144380A4 (fr) 2003-11-26

Family

ID=27394520

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99965757A Withdrawn EP1144380A4 (fr) 1998-11-30 1999-11-22 Derive de meta-nitrophenol et procede de production correspondant

Country Status (5)

Country Link
EP (1) EP1144380A4 (fr)
JP (1) JP2003506312A (fr)
CN (1) CN1376145A (fr)
AU (1) AU2145500A (fr)
WO (1) WO2000032573A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL167957A (en) 2000-02-04 2009-07-20 Sumitomo Chemical Co Hydroxypyridine compounds
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 (zh) * 2013-05-23 2014-07-30 大连理工大学 弱碱性芳胺为重氮组分的偶氮染料制备方法
CN103288763B (zh) * 2013-06-20 2015-06-03 郑州福源动物药业有限公司 一种2,6-二氯吡嗪的工业化生产方法

Citations (5)

* Cited by examiner, † Cited by third party
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 (fr) * 1981-05-18 1982-11-24 Zoecon Corporation Phosphinates et phosphinothioates substitués et leur utilisation pour la lutte contr les mauvaises herbes
EP0071572A2 (fr) * 1981-07-28 1983-02-09 Ciba-Geigy Ag Dérivés de l'acide nitro-2 pyridyloxy-4 ou -5 phosphonique, leur procédé de préparation, leur utilisation comme herbicides et/ou régulateurs de la croissance des plantes et/ou microbicides, ainsi que les intermédiaires utilisés pour leur préparation, leur procédé de préparation et leur utilisation comme 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)

* Cited by examiner, † Cited by third party
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
JPS56154467A (en) * 1980-01-10 1981-11-30 Nyegaard & Co As Novel pyrimidine-2-sulfide compound
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 (de) * 1986-04-23 1987-10-29 Schering Ag Pyrimidin-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US4966622A (en) * 1988-04-12 1990-10-30 Ciba-Geigy Corporation N-phenyl-N-pyrimidin-2-ylureas
EP0973395B1 (fr) * 1997-03-14 2003-12-03 ISK Americas Incorporated Diaryl ethers, procedes d'elaboration, et compositions herbicides et desiccantes les contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
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 (fr) * 1981-05-18 1982-11-24 Zoecon Corporation Phosphinates et phosphinothioates substitués et leur utilisation pour la lutte contr les mauvaises herbes
EP0071572A2 (fr) * 1981-07-28 1983-02-09 Ciba-Geigy Ag Dérivés de l'acide nitro-2 pyridyloxy-4 ou -5 phosphonique, leur procédé de préparation, leur utilisation comme herbicides et/ou régulateurs de la croissance des plantes et/ou microbicides, ainsi que les intermédiaires utilisés pour leur préparation, leur procédé de préparation et leur utilisation comme 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)

* Cited by examiner, † Cited by third party
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
WO2000032573A1 (fr) 2000-06-08
WO2000032573A8 (fr) 2001-09-13
CN1376145A (zh) 2002-10-23
JP2003506312A (ja) 2003-02-18
AU2145500A (en) 2000-06-19
EP1144380A1 (fr) 2001-10-17

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