PT782997E - Derivados de triazolopirimidina - Google Patents

Derivados de triazolopirimidina Download PDF

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Publication number
PT782997E
PT782997E PT97105710T PT97105710T PT782997E PT 782997 E PT782997 E PT 782997E PT 97105710 T PT97105710 T PT 97105710T PT 97105710 T PT97105710 T PT 97105710T PT 782997 E PT782997 E PT 782997E
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Prior art keywords
triazolo
dichloro
pyrimidine
phenyl
fluorophenyl
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PT97105710T
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English (en)
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Guido Albert
Klaus-Jurgen Pees
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Shell Int Research
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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

Description

-1 - -^8 ZOQ>
DESCRIÇÃO "DERIVADOS DE TRIAZOLOPIRIMIDINA"
Esta invenção refere-se a certos derivados de triazolopirimidina e a um processo para a sua preparação.
De acordo com a invenção é assim fornecido um composto da
na qual R3 representa um grupo fenilo ou naftilo opcionalmente substituído, em que os substituintes opcionais são seleccionados de átomos de halogénio, grupos nitro, ciano, tiocianato, cianato, hidroxilo, alquilo haloalquilo C1.12, alcoxi C1.12, haloalcoxi Cj.12, amino, alquil Ci_i2-amino, di-alquil Ci.n-amino, formilo, alcoxi Ci.i2-carbonilo, carboxilo, alcanoílo alquil Ci.i2-tio, alquil Ci_i2- sulfinilo, alqui Ci.i2-sulfonilo, carbamoílo, alquil Ci.i2-amido e heterociclilo de 3 a 6 membros e grupos fenilo, fenoxi, benzilo, benziloxi e cicloalquilo C3.8 opcionalmente substituídos, cada um opcionalmente substituído por um ou mais átomos de halogénio ou grupos nitro, ciano, alquilo C1-12, haloalquilo C1.12, alcoxi Ci_i2 ou haloalcoxi C\.n, e Hal representa um átomo de cloro ou bromo. É preferido que R3 represente um grupo fenilo ou naftilo, sendo cada grupo opcionalmente substituído por um ou mais substituintes seleccionados -2- de átomos de halogénio ou de grupos nitro, ciano, hidroxilo, alquilo Ci_i2, haloalquilo Cm2» alcoxi Cm2, haloalcoxi Cm2, amino, alquil Ci_4-amino, di-alquil Ci.4-amino, formilo, alcoxi Ci.4-carbonilo, carboxilo, fenilo, fenoxi e benziloxi.
Mais preferencialmente, R3 representa um grupo fenilo opcionalmente substituído por até três substituintes seleccionados de átomos de halogénio ou de grupos alquilo C1.4, haloalquilo Cm, alcoxi Cm, haloalcoxi Cm, fenilo, fenoxi e benziloxi, ou um grupo naftilo.
Um subgrupo de compostos de fórmula II particularmente preferido é aquele no qual R3 representa um grupo fenilo, fluorofenilo, clorofenilo, bromo-fenilo,cloro-fluorofenilo, metilfenilo, propilfenilo, trifluorometilfenilo, metoxife-nilo, etoxifenilo, dimetoxifenilo, trimetoxifenilo, trifluorometoxifenilo, bifenililo, fenoxifenilo, benziloxifenilo ou naftilo. É especialmente preferido que o composto de fórmula II seja seleccionado a partir de 5.7- dicloro-6-(4-metilfenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dibromo-6-fenil-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-metoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-metoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-metoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-etoxifenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-fenil-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(3-clorofenil)-l ,2,4-triazolo[l ,5-a]pirimidina, 5.7- dicloro-6-(3-trifluorometilfenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-isopropilfenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(4-trifluorometoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-naft-2-il-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3,4-dimetoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-clorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina5 5.7- dicloro-6-(4-fluorofenil)-l,2,4-triazolo[l,5-a]pirimidina, 557-dicloro-6-(4-bifenilil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(2-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-fenoxifenil)-l,2,4-triazolo[l,5-a]pirimidina,
5.7- dicloro-6-(4-benziloxifenil)-1,2,4-triazolo[ 1,5-a]pirimidinaJ 5.7- dicloro-6-(4-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-fluorofenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(2-benziloxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2,3-dimetoxifenil)-l ,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3,4,5-trimetoxifenil)-1,2,4-triazolo[l ,5-a]pirimidina, e 5.7- dicloro-6-(2-cloro-6-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina. A presente invenção proporciona também um processo para a preparação de um composto de fórmula II conforme anteriormente definido que compreende a reacção de um composto com a fórmula geral
na qual R3 é como anteriormente definido, com um agente de cloração ou bromação, tal como oxicloreto de fósforo ou oxibrometo de fósforo. -4-
Os compostos de fórmula V podem ser preparados por reacção de 3-amino-1,2,4-triazol com um éster de ácido malónico apropriado sob condições alcalinas de acordo com o método de Y. Makisumi, Chem. Pharm. Buli., 9, 801, (1961).
Os compostos de fórmula II são úteis como intermediários na preparação de certos derivados de triazolopirimidina fungicidas que são o tema da patente EP-B-0 550 113, da qual a presente patente é dividida.
Lisboa, 3 de Julho de 2000
JORGE CRUZ
Agente Oficial da Propriedade Industrial RUA VICTOR CORDON, 14 1200 LISBOA

Claims (6)

  1. REIVINDICAÇÕES 1. Um composto da fórmula geral II
    <3 t t na qual R representa um grupo fenilo ou naftilo opcionalmente substituído, em que os substituintes opcionais são seleccionados de átomos de halogénio, grupos nitro, ciano, tiocianato, cianato, hidroxilo, alquilo Q.12, haloalquilo C1.12, alcoxi CM2, haloalcoxi C1.12, amino, alquil Ci_i2-amino, di-alquil Ci_i2-amino, formilo, alcoxi Ci_i2-carbonilo, carboxilo, alcanoílo C1.12, alquil Ci_i2-tio, alquil C1.12-sulfinilo, alqui C1.12-sulfonilo, carbamoílo, alquil Ci_i2-amido e heterociclilo de 3 a 6 membros e grupos fenilo, fenoxi, benzilo, benziloxi e cicloalquilo C3.8 opcionalmente substituídos, cada um opcionalmente substituído por um ou mais átomos de halogénio ou grupos nitro, ciano, alquilo C1.12, haloalquilo Ci_i2, alcoxi C1-12 ou haloalcoxi C1.12; e Hal representa um átomo de cloro ou bromo.
  2. 2. Um composto de acordo com a Reivindicação 1 no qual R1 representa um grupo fenilo ou naftilo, sendo cada grupo opcionalmente substituído por um ou mais substituintes seleccionados de átomos de halogénio ou de grupos nitro, ciano, hidroxilo, alquilo Cm2, haloalquilo Ci_i2, alcoxi Q.12, haloalcoxi C1.12, amino, alquil Ci.4-amino, di-alquil Ci^-amino, formilo, alcoxi Ci.4-carbonilo, carboxilo, fenilo, fenoxi, benzilo e benziloxi. 1 Um composto de acordo com a Reivindicação 1 ou Reivindicação 2 no qual R1 representa um grupo fenilo opcionalmente substituído por até três substituintes seleccionados de átomos de halogénio ou de grupos alquilo Ci_4, haloalquilo Cm, alcoxi Cm» haloalcoxi Cm» fenilo, fenoxi e benziloxi, ou um grupo naftilo.
  3. 4. Um composto de acordo com qualquer uma das Reivindi-cações 1 a 3 no qual R representa um grupo fenilo, fluorofenilo, clorofenilo, bromofenilo, clorofluorofenilo, metilfenilo, propilfenilo, trifluorometilfenilo, metoxifenilo, etoxifenilo, dimetoxifenilo, trimetoxifenilo, trifluorometoxifenilo, bifenililo, fenoxifenilo, benziloxifenilo ou naftilo.
  4. 5. Um composto de acordo com qualquer uma das reivindicações precedentes seleccionado a partir de 5.7- dicloro-6-(4-metilfenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dibromo-6-fenil-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-metoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-metoxifenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(3-metoxifenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(4-etoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-fenil-1,2,4-triazolo[l ,5-a]pirimidina, 5.7- dicloro-6-(3-clorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-trifluorometilfenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-isopropilfenil)-l ,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-trifluorometoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-naft-2-il-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3,4-dimetoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-clorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-bifenilil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, -3- 5.7- dicloro-6-(4-fenoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(4-benziloxifenil)-l,2,4-triazolo[l,5-a]pirimidina, 5.7- dicloro-6-(4-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-bromofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2-benziloxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(2,3-dimetoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, 5.7- dicloro-6-(3,4,5-trimetoxifenil)-1,2,4-triazolo[ 1,5-a]pirimidina, e 5.7- dicloro-6-(2-cloro-6-fluorofenil)-1,2,4-triazolo[ 1,5-a]pirimidina.
  5. 6. Um processo para a preparação de um composto de fórmula II conforme definido em qualquer uma das reivindicações precedentes que compreende a reacção de um composto da fórmula geral (V)
    na qual R3 é como definido em qualquer uma das reivindicações precedentes, com um agente de cloração ou bromação.
  6. 7. Um processo de acordo com a reivindicação 6 no qual o agente de cloração ou bromação é oxicloreto de fósforo ou oxibrometo de fósforo. Lisboa, 3 de Julho de 2000
    JORGE CRUZ Agente Oficial da Propriedade Industrie RUA V1CTOR CORDON, 14 1200 LISBOA
PT97105710T 1991-12-30 1992-12-28 Derivados de triazolopirimidina PT782997E (pt)

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JP (1) JP3347170B2 (pt)
KR (1) KR100271913B1 (pt)
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