PL139633B1 - Method of obtaining novel derivatives of 1,2,4-triazole - Google Patents

Method of obtaining novel derivatives of 1,2,4-triazole Download PDF

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Publication number
PL139633B1
PL139633B1 PL1983243409A PL24340983A PL139633B1 PL 139633 B1 PL139633 B1 PL 139633B1 PL 1983243409 A PL1983243409 A PL 1983243409A PL 24340983 A PL24340983 A PL 24340983A PL 139633 B1 PL139633 B1 PL 139633B1
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PL
Poland
Prior art keywords
triazole
formula
fluorophenyl
compound
scheme
Prior art date
Application number
PL1983243409A
Other languages
English (en)
Other versions
PL243409A1 (en
Inventor
Kenneth Richardson
Peter J Whittle
Original Assignee
Pfizer
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 Pfizer filed Critical Pfizer
Publication of PL243409A1 publication Critical patent/PL243409A1/xx
Publication of PL139633B1 publication Critical patent/PL139633B1/pl

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Claims (4)

1. Zastrzezenia patentowe 1. Sposób wytwarzania nowych pochodnych 1,2,4-triazolu o ogólnym wzorze 1, w którym R oznacza grupe fenylowa ewentualnie podstawiona 1-3 jednakowymi lub róznymi podstawnikami, takimi jak atom fluoru, chloru, bromu lub jodu albo grupa trójfluorometylowa, oraz soli tych zwiazków, znamienny tym, ze 1,2,4-triazol lub jego sól z metalem alkalicznym poddaje sie reakcji ze zwiazkiem o ogólnym wzorze 2, w którym R ma wyzej podane znaczenie, po czym powstaly zwiazek o wzorze 1 ewentualnie przeprowadza sie w soli
2. Sposób wedlug zastrz* 1, znamienny tym, ze reakcje przeprowadza sie albo stosujac 1,2,4-triazol w obecnosci zasady albo sól potasowa 1,2,4-triazolui
3. * Sposób wedlug zastrz. 2, znamienny tym, ze jako zasade stosuje sie weglan potasu.
4. Sposób wedlug zastrz* 1, znamienny tym, ze jako substrat stosuje sie zwiazek o wzorze 2, w którym R oznacza grupe 4-fluorofenylowa, 4-chlorofenylowa, 4-trój- fluorometylofenylowa, 2-fluorofenylowa, 2,4-dwuchlorofenyIowa, 2,4-dwufluorofenylowa, 2-flu- oro-4-chlorofenylowa, 2,5-dwufluorofenylowa, 2,4,6-trójfluorofenylowa lub 4-bromo-2,5-dwu- fluorofenylowa. 5i Sposób wedlug zastrz. 1 albo 2, znamienny tym, ze reakcje prze¬ prowadza sie w rozpuszczalniku organicznym w temperaturze do 130°C. 9H N^N-CH2-C- CF3 WN R Wzór 1 Cf^-C—CH2 R Wzór 2139 633 Mg] 1 MQ , r|rCi focotf) CR Cl Schemat 1 ci n O C^^O^1 " CF3C^CH2 OH CR-C-CH,-! Cl 1 K2C03 O N Schemat Z CF,-C=0 Cl Cl JO CF3-C/-CH2 Cl f Cl 1,2,4-triazol K2C03 OH f |-CH2-Ó-CF3 luJ i Cl N Cl Schemat 3 Pracownia Poligraficzna UP PRL. Naklad 100 egz Cena 220 zl PL PL
PL1983243409A 1982-08-14 1983-08-12 Method of obtaining novel derivatives of 1,2,4-triazole PL139633B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8223459 1982-08-14
GB8231309 1982-11-02

Publications (2)

Publication Number Publication Date
PL243409A1 PL243409A1 (en) 1985-07-16
PL139633B1 true PL139633B1 (en) 1987-02-28

Family

ID=26283600

Family Applications (2)

Application Number Title Priority Date Filing Date
PL1983252362A PL140540B1 (en) 1982-08-14 1983-08-12 Method of obtaining novel derivatives of 1,2,4-triazole
PL1983243409A PL139633B1 (en) 1982-08-14 1983-08-12 Method of obtaining novel derivatives of 1,2,4-triazole

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PL1983252362A PL140540B1 (en) 1982-08-14 1983-08-12 Method of obtaining novel derivatives of 1,2,4-triazole

Country Status (22)

Country Link
US (1) US4616027A (pl)
EP (1) EP0104734B1 (pl)
KR (1) KR880001046B1 (pl)
AU (1) AU542692B2 (pl)
CA (1) CA1249827A (pl)
DD (1) DD207715A5 (pl)
DE (1) DE3372481D1 (pl)
DK (1) DK162842C (pl)
ES (2) ES8600256A1 (pl)
FI (1) FI82933C (pl)
GR (1) GR78905B (pl)
HU (1) HU188943B (pl)
IE (1) IE55845B1 (pl)
IL (1) IL69485A (pl)
IN (1) IN160173B (pl)
NO (1) NO159086C (pl)
NZ (1) NZ205243A (pl)
PH (1) PH18645A (pl)
PL (2) PL140540B1 (pl)
PT (1) PT77193B (pl)
SU (1) SU1468416A3 (pl)
YU (1) YU42874B (pl)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BG48681A3 (en) * 1982-12-14 1991-04-15 Ciba Geigy Ag Fungicide means
GB8302498D0 (en) * 1983-01-29 1983-03-02 Pfizer Ltd Antifungal agents
US4584307A (en) * 1983-08-10 1986-04-22 Pfizer Inc. Antifungal 2-aryl-2-hydroxy perfluoro-1-(1H-1,2,4-triazol-1-yl) alkanones and alkanols
GB8322983D0 (en) * 1983-08-26 1983-09-28 Pfizer Ltd Triazole antifungal agents
FR2622582B1 (fr) * 1987-10-29 1990-01-19 Rhone Poulenc Agrochimie Composes a groupe imidazole ou triazole, utilisation de ceux-ci a titre de fongicide, procede de preparation
IT1186784B (it) * 1985-11-04 1987-12-16 Montedison Spa Azoliderivati ad attivita' antufungina
IT1196528B (it) * 1986-07-21 1988-11-16 Donegani Guido Ist Azolilderivati ad attivita' antifungina
IT1198240B (it) * 1986-12-23 1988-12-21 Agrimont Spa Azolilderivati fungicidi
US4935436A (en) * 1989-01-23 1990-06-19 The Dow Chemical Company Substituted triazoles and their use as fungicides
EP0470466A3 (en) * 1990-08-09 1992-07-29 Bayer Ag Halogenalkyl-azolyl derivatives
US5262434A (en) * 1990-08-09 1993-11-16 Bayer Aktiengesellschaft Halogenoalkyl-azolyl derivatives
JP3471831B2 (ja) * 1991-12-09 2003-12-02 富山化学工業株式会社 新規なトリアゾール誘導体およびその塩
US5611210A (en) * 1993-03-05 1997-03-18 Ikon Corporation Fluoroiodocarbon blends as CFC and halon replacements
US6270689B1 (en) 1998-03-26 2001-08-07 Ikon Corporation Blend compositions of trifluoroiodomethane, tetrafluoroethane and difluoroethane
WO2008124132A1 (en) * 2007-04-05 2008-10-16 The Johns Hopkins University Chirally pure isomers of itraconazole and inhibitors of lanosterol 14a- demethylase for use as angiogenesis inhibitors
US9095589B2 (en) 2007-04-05 2015-08-04 Johns Hopkins University Chirally pure isomers of itraconazole for use as angiogenesis inhibitors
US10071971B2 (en) 2012-12-19 2018-09-11 Basf Se Substituted [1,2,4]triazole compounds and their use as fungicides

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IE45765B1 (en) * 1976-08-19 1982-11-17 Ici Ltd Triazoles and imidazoles useful as plant fungicides and growth regulating agents
DE2832234A1 (de) * 1978-07-21 1980-01-31 Bayer Ag Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
US4654332A (en) * 1979-03-07 1987-03-31 Imperial Chemical Industries Plc Heterocyclic compounds
DE2951164A1 (de) * 1979-12-19 1981-07-16 Bayer Ag, 5090 Leverkusen Substituierte triazolylmethyl-tert.-butyl-ketone, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte
EP0123160B1 (en) * 1980-08-18 1992-10-28 Zeneca Limited Triazole compounds, a process for preparing them, their use as plant fungicides and plant growth regulators and compositions containing them
IE51533B1 (en) * 1980-08-28 1987-01-07 Ici Ltd Pharmaceutical compositions of fungicidal triazole derivatives

Also Published As

Publication number Publication date
NO832915L (no) 1984-02-15
CA1249827A (en) 1989-02-07
DD207715A5 (de) 1984-03-14
YU168283A (en) 1986-02-28
AU1793083A (en) 1984-02-16
ES524873A0 (es) 1985-10-01
PT77193B (en) 1986-03-21
NO159086C (no) 1988-11-30
FI832904A (fi) 1984-02-15
KR880001046B1 (ko) 1988-06-18
IN160173B (pl) 1987-06-27
DE3372481D1 (en) 1987-08-20
PT77193A (en) 1983-09-01
IE831889L (en) 1984-02-14
US4616027A (en) 1986-10-07
FI82933B (fi) 1991-01-31
FI832904A0 (fi) 1983-08-11
SU1468416A3 (ru) 1989-03-23
DK162842B (da) 1991-12-16
PH18645A (en) 1985-08-23
NZ205243A (en) 1986-04-11
IL69485A0 (en) 1983-11-30
GR78905B (pl) 1984-10-02
DK367883A (da) 1984-02-15
DK367883D0 (da) 1983-08-12
HU188943B (en) 1986-05-28
AU542692B2 (en) 1985-03-07
IE55845B1 (en) 1991-01-30
NO159086B (no) 1988-08-22
YU42874B (en) 1988-12-31
IL69485A (en) 1987-09-16
FI82933C (fi) 1991-05-10
PL243409A1 (en) 1985-07-16
EP0104734B1 (en) 1987-07-15
ES540857A0 (es) 1985-11-16
PL252362A1 (en) 1985-11-19
ES8601932A1 (es) 1985-11-16
EP0104734A1 (en) 1984-04-04
KR840005719A (ko) 1984-11-15
PL140540B1 (en) 1987-05-30
ES8600256A1 (es) 1985-10-01
DK162842C (da) 1992-05-04

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