CA2302058A1 - A process for preparing 5-methoxy-4-methyl-2,4-dihydro-3h-1,2,4-triazol-3-one - Google Patents

A process for preparing 5-methoxy-4-methyl-2,4-dihydro-3h-1,2,4-triazol-3-one Download PDF

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Publication number
CA2302058A1
CA2302058A1 CA002302058A CA2302058A CA2302058A1 CA 2302058 A1 CA2302058 A1 CA 2302058A1 CA 002302058 A CA002302058 A CA 002302058A CA 2302058 A CA2302058 A CA 2302058A CA 2302058 A1 CA2302058 A1 CA 2302058A1
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CA
Canada
Prior art keywords
triazol
dihydro
methoxy
methyl
preparing
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
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CA002302058A
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French (fr)
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CA2302058C (en
Inventor
Klaus-Helmut Muller
Peter Babczinski
Hans-Joachim Santel
Robert R. Schmidt
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Bayer AG
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Individual
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Priority to CA002420329A priority Critical patent/CA2420329C/en
Publication of CA2302058A1 publication Critical patent/CA2302058A1/en
Application granted granted Critical
Publication of CA2302058C publication Critical patent/CA2302058C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • 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
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur 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
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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

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

Abstract

This invention relates to a process for preparing 5-methoxy-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula (II-118) (see formula II-118) which process comprises reacting hydrazino-formic acid phenyl ester with an about equimolar amount of O,N,N-trimethylimino-carbonate.
CA002302058A 1989-10-12 1990-10-10 A process for preparing 5-methoxy-4-methyl-2,4-dihydro-3h-1,2,4-triazol-3-one Expired - Lifetime CA2302058C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002420329A CA2420329C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3934081A DE3934081A1 (en) 1989-10-12 1989-10-12 SULFONYLAMINOCARBONYLTRIAZOLINONE
DEP3934081.3 1989-10-12
CA002189698A CA2189698C (en) 1989-10-12 1990-10-10 Substituted 1,2,3-triazol-3-ones

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002189698A Division CA2189698C (en) 1989-10-12 1990-10-10 Substituted 1,2,3-triazol-3-ones

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002420329A Division CA2420329C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones

Publications (2)

Publication Number Publication Date
CA2302058A1 true CA2302058A1 (en) 1991-04-13
CA2302058C CA2302058C (en) 2004-05-25

Family

ID=6391328

Family Applications (4)

Application Number Title Priority Date Filing Date
CA002420329A Expired - Lifetime CA2420329C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones
CA002189698A Expired - Lifetime CA2189698C (en) 1989-10-12 1990-10-10 Substituted 1,2,3-triazol-3-ones
CA002302058A Expired - Lifetime CA2302058C (en) 1989-10-12 1990-10-10 A process for preparing 5-methoxy-4-methyl-2,4-dihydro-3h-1,2,4-triazol-3-one
CA002027206A Expired - Lifetime CA2027206C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CA002420329A Expired - Lifetime CA2420329C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones
CA002189698A Expired - Lifetime CA2189698C (en) 1989-10-12 1990-10-10 Substituted 1,2,3-triazol-3-ones

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA002027206A Expired - Lifetime CA2027206C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones

Country Status (13)

Country Link
EP (2) EP0422469B1 (en)
JP (1) JPH03133966A (en)
KR (1) KR0171400B1 (en)
AU (1) AU627080B2 (en)
BR (1) BR9005095A (en)
CA (4) CA2420329C (en)
CZ (1) CZ281525B6 (en)
DE (3) DE3934081A1 (en)
DK (2) DK0422469T3 (en)
ES (2) ES2087107T3 (en)
HU (1) HU218976B (en)
PL (1) PL165494B1 (en)
SK (1) SK495090A3 (en)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3936622A1 (en) * 1989-11-03 1991-05-08 Bayer Ag HALOGENED SULFONYLAMINOCARBONYLTRIAZOLINONE
DE4030063A1 (en) * 1990-09-22 1992-03-26 Bayer Ag SUBSTITUTED 5-ALKOXY-1,2,4, -TRIAZOL-3- (THI) ONE
DE4110795A1 (en) * 1991-04-04 1992-10-08 Bayer Ag SULFONYLAMINOCARBONYLTRIAZOLINONE WITH OXYGEN SUBSTITUTES
DE4131842A1 (en) * 1991-09-25 1993-04-01 Bayer Ag SULFONYLAMINOCARBONYLTRIAZOLINONE WITH TWO OXYGEN SUBSTITUTES
DE4238125A1 (en) * 1992-11-12 1994-05-19 Bayer Ag Substituted triazolinones
US6906006B1 (en) 1988-11-23 2005-06-14 Bayer Aktiengesellschaft N-arly-substituted nitrogen-containing heterocycles, processes and novel intermediates for their preparation, and their use as herbicides and plant growth regulators
DE3928662A1 (en) * 1989-08-30 1991-03-07 Bayer Ag SUBSTITUTED 4,5-DIAMINO-1,2,4-TRIAZOL-3- (THI) ONE
US5534486A (en) * 1991-04-04 1996-07-09 Bayer Aktiengesellschaft Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen
DE4316430A1 (en) * 1993-05-17 1994-11-24 Bayer Ag Substituted triazolinones
DE4343595A1 (en) * 1993-12-21 1995-06-22 Bayer Ag Process for the preparation of sulfonylaminocarbonyltriazolinones
DE4411913A1 (en) * 1994-04-07 1995-10-12 Bayer Ag Substituted sulfonylaminocarbonyltriazolinones
DE4435547A1 (en) * 1994-10-05 1996-04-11 Bayer Ag Sulfonylaminocarbonyltriazolinone with substituents bonded via oxygen and sulfur
DE19502579A1 (en) * 1995-01-27 1996-08-01 Bayer Ag Sulfonylamino (thio) carbonyl-triazolin (thi) one
DE19525974A1 (en) * 1995-07-17 1997-01-23 Bayer Ag Substituted arylsulfonylamino (thio) carbonyltriazolin (thi) one
DE19530450A1 (en) * 1995-08-18 1997-02-20 Bayer Ag Process for the preparation of substituted aminotriazolinones
ZA974703B (en) * 1996-05-30 1997-12-30 Bayer Ag Substituted sulfonylamino(thio)carbonyl compounds.
DE19632945A1 (en) * 1996-08-16 1998-02-19 Bayer Ag Substituted sulfonylamino (thio) carbonyl compounds
DE19802697A1 (en) 1998-01-24 1999-07-29 Bayer Ag Selective, synergistic herbicidal composition, especially for weed control in wheat
DE19823131A1 (en) * 1998-05-23 1999-11-25 Bayer Ag New sulfonylaminocarbonyl-triazolinone derivatives, used as herbicides or as fungicides or bactericides for plant protection
DE19843766A1 (en) * 1998-09-24 2000-03-30 Bayer Ag Substituted thiazole (in) ylidene aminosulfonylamino (thio) carbonyl triazolinones
DE19845408A1 (en) 1998-10-02 2000-04-27 Bayer Ag Selective herbicides based on a substituted phenylsulfonylaminocarbonyl-triazolinone
DE19845407B4 (en) 1998-10-02 2012-06-28 Arysta LifeScience North America Corp.(n.d.Ges.d.Staates Californien) Selective herbicides based on a substituted phenylsulfonylaminocarbonyl-triazolinone
US5912354A (en) * 1998-12-11 1999-06-15 Bayer Corporation Process for preparing 4-amino-1,2,4-triazolin-5-ones
KR100704718B1 (en) * 1999-12-27 2007-04-09 바이엘 코포레이션 A process for the manufacture of the salts of sulfonylaminocarbonyl triazolinones
KR100431154B1 (en) * 2002-04-12 2004-05-12 (주)하나실업 Patterning method for denim
EP1717228A1 (en) 2005-04-28 2006-11-02 Bayer CropScience GmbH Sulfonylamino(thio)carbonylderivatives as herbicides or plant growth regulators
DE102008060967A1 (en) 2008-12-06 2010-06-10 Bayer Schering Pharma Aktiengesellschaft Substituted phenylsulfonyltriazolones and their use
WO2013134562A1 (en) 2012-03-09 2013-09-12 Inception 2, Inc. Triazolone compounds and uses thereof
EP2935228B9 (en) 2012-12-20 2017-12-06 Inception 2, Inc. Triazolone compounds and uses thereof
CN105473558B (en) 2013-06-20 2019-04-19 拜耳作物科学股份公司 Aromatic yl sulfide derivative and aryl oxysulfide derivative as acaricide and insecticide
CA2921420A1 (en) 2013-09-06 2015-03-12 Inception 2, Inc. Triazolone compounds and uses thereof
JOP20190094A1 (en) 2016-10-27 2019-04-25 Broad Inst Inc 2,4,5-trisubstituted 1,2,4-triazolones useful as inhibitors of dhodh

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
DE1126882B (en) * 1960-05-03 1962-04-05 Boehringer Sohn Ingelheim Process for the preparation of 1,2,4-triazolonen- (5)
US4487773A (en) * 1981-03-16 1984-12-11 Mead Johnson & Company 1,2,4-Triazol-3-one antidepressants
BE894856A (en) * 1982-10-28 1983-02-14 Fahlberg List Veb 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd.
US4575555A (en) * 1983-06-29 1986-03-11 Mead Johnson & Company 4-(3-Chlorophenyl)-1,2,3,6-tetrahydropyridine derivative
DE3709574A1 (en) * 1987-03-24 1988-10-06 Bayer Ag SUBSTITUTED TRIAZOLINONES
DE3815765A1 (en) * 1988-05-09 1989-11-23 Bayer Ag 2-SULFONYLAMINOCARBONYL-2,4-DIHYDRO-3H-1,2,4-TRIAZOL-3-ONE, INCLUDING 4,5-CONDENSED, BICYCLIC DERIVATIVES, METHODS AND NEW INTERMEDIATE PRODUCTS FOR THEIR PRODUCTION AND USE THEREOF AS ARE
ES2063065T3 (en) * 1988-03-07 1995-01-01 Chugai Pharmaceutical Co Ltd DERIVATIVES OF TRIAZOL, PROCEDURE FOR ITS PREPARATION AND HERBICIDE COMPOSITIONS THAT CONTAIN THEM.

Also Published As

Publication number Publication date
AU6459190A (en) 1991-04-18
HUT55369A (en) 1991-05-28
CA2189698A1 (en) 1991-04-13
DE59010314D1 (en) 1996-06-13
HU906419D0 (en) 1991-04-29
CA2027206C (en) 1997-12-23
KR910007893A (en) 1991-05-30
CA2027206A1 (en) 1991-04-13
DE3934081A1 (en) 1991-04-18
EP0683157B1 (en) 2004-05-26
CZ495090A3 (en) 1996-07-17
EP0422469B1 (en) 1996-05-08
SK280209B6 (en) 1999-09-10
DK0683157T3 (en) 2004-09-27
CZ281525B6 (en) 1996-10-16
CA2302058C (en) 2004-05-25
BR9005095A (en) 1991-09-17
KR0171400B1 (en) 1999-02-01
EP0422469A3 (en) 1992-01-08
CA2189698C (en) 2003-05-06
PL287259A1 (en) 1992-01-27
EP0683157A1 (en) 1995-11-22
DE59010938D1 (en) 2004-07-01
ES2087107T3 (en) 1996-07-16
HU218976B (en) 2001-01-29
AU627080B2 (en) 1992-08-13
CA2420329A1 (en) 1991-04-13
DK0422469T3 (en) 1996-08-26
EP0422469A2 (en) 1991-04-17
JPH03133966A (en) 1991-06-07
PL165494B1 (en) 1994-12-30
SK495090A3 (en) 1999-09-10
ES2222457T3 (en) 2005-02-01
CA2420329C (en) 2005-11-29

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