CA2320676A1 - Process and intermediates for the preparation of aminotriazine derivatives - Google Patents

Process and intermediates for the preparation of aminotriazine derivatives Download PDF

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Publication number
CA2320676A1
CA2320676A1 CA002320676A CA2320676A CA2320676A1 CA 2320676 A1 CA2320676 A1 CA 2320676A1 CA 002320676 A CA002320676 A CA 002320676A CA 2320676 A CA2320676 A CA 2320676A CA 2320676 A1 CA2320676 A1 CA 2320676A1
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CA
Canada
Prior art keywords
phenyl
preparation
formula
radicals
substituted
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
Application number
CA002320676A
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French (fr)
Other versions
CA2320676C (en
Inventor
Ernst Beriger
Haukur Kristinsson
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Syngenta Participations AG
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Individual
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Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2320676A1 publication Critical patent/CA2320676A1/en
Application granted granted Critical
Publication of CA2320676C publication Critical patent/CA2320676C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

A process for the preparation of aminotriazine derivatives of the formula <See formula I>

wherein R is hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C4alkyl substituted by from 1 to 10 halogen atoms or by from 1 to 3 radicals from the group C1-C3alkoxy, C1-C3alkylthio and phenyl, phenyl or phenyl substituted by from 1 to 3 radicals from the group halogen, methyl, ethyl, methoxy, methylthio and nitro, which process comprises reacting with hydrazine hydrate a compound of formula II

<See formula II>

wherein R1 is hydrogen, C1-C4alkyl, C3-C6cycloalkyl, C1-C4alkyl substituted by from 1 to 9 chlorine atoms, C1-C3alkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, phenyl, phenyl substituted by from 1 to 3 radicals from the group halogen, methyl, ethyl, methoxy, methylthio and nitro, or pyridyl, and subjecting the resulting compound of formula III

(See formula III) to acid hydrolysis. The compounds prepared in accordance with the invention are suitable as starting materials for the preparation of effective pesticides.
CA002320676A 1989-11-15 1990-11-13 Process and intermediates for the preparation of aminotriazine derivatives Expired - Lifetime CA2320676C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH4107/89-7 1989-11-15
CH410789 1989-11-15
CA002029838A CA2029838C (en) 1989-11-15 1990-11-13 Process for the preparation of aminotriazine derivatives

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002029838A Division CA2029838C (en) 1989-11-15 1990-11-13 Process for the preparation of aminotriazine derivatives

Publications (2)

Publication Number Publication Date
CA2320676A1 true CA2320676A1 (en) 1991-05-16
CA2320676C CA2320676C (en) 2004-11-02

Family

ID=4269949

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002320676A Expired - Lifetime CA2320676C (en) 1989-11-15 1990-11-13 Process and intermediates for the preparation of aminotriazine derivatives
CA002029838A Expired - Lifetime CA2029838C (en) 1989-11-15 1990-11-13 Process for the preparation of aminotriazine derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002029838A Expired - Lifetime CA2029838C (en) 1989-11-15 1990-11-13 Process for the preparation of aminotriazine derivatives

Country Status (14)

Country Link
EP (1) EP0433218B1 (en)
JP (1) JP2943010B2 (en)
KR (1) KR0150208B1 (en)
CA (2) CA2320676C (en)
DE (1) DE59010496D1 (en)
DK (1) DK0433218T3 (en)
ES (1) ES2091815T3 (en)
GR (1) GR3020992T3 (en)
IE (1) IE73669B1 (en)
IL (3) IL96280A (en)
PT (1) PT95888B (en)
SG (1) SG43813A1 (en)
TW (1) TW199149B (en)
ZA (1) ZA909120B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9304178D0 (en) * 1993-03-02 1993-04-21 Ciba Geigy Ag Process for the preparation of 6-alkyl-4-(pyridin-3-yl-methyleneamino),5-dihydro-1,2,4-triazin-3(2h)-one
US5384403A (en) * 1993-03-31 1995-01-24 Ciba-Geigy Corporation Process for the preparation of aminotriazine derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5416515B1 (en) * 1968-08-19 1979-06-22
JPS6011478A (en) * 1983-06-30 1985-01-21 Showa Denko Kk Oxadiazolinon derivative and herbicide
US4699647A (en) * 1985-05-30 1987-10-13 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
DE3853662D1 (en) * 1987-10-16 1995-06-01 Ciba Geigy Ag Pesticides.

Also Published As

Publication number Publication date
CA2320676C (en) 2004-11-02
JPH03188070A (en) 1991-08-16
DE59010496D1 (en) 1996-10-17
PT95888A (en) 1991-09-13
IE73669B1 (en) 1997-07-02
KR910009677A (en) 1991-06-28
GR3020992T3 (en) 1996-12-31
CA2029838C (en) 2001-06-19
DK0433218T3 (en) 1996-09-30
PT95888B (en) 1997-11-28
IL111617A (en) 1996-05-14
IL111617A0 (en) 1995-01-24
IL96280A0 (en) 1991-08-16
TW199149B (en) 1993-02-01
ES2091815T3 (en) 1996-11-16
IL96280A (en) 1996-01-31
IE904113A1 (en) 1991-05-22
ZA909120B (en) 1991-07-31
EP0433218B1 (en) 1996-09-11
SG43813A1 (en) 1997-11-14
CA2029838A1 (en) 1991-05-16
KR0150208B1 (en) 1998-10-15
EP0433218A1 (en) 1991-06-19
JP2943010B2 (en) 1999-08-30

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