CA2420329A1 - Sulphonylaminocarbonyltriazolinones - Google Patents

Sulphonylaminocarbonyltriazolinones Download PDF

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Publication number
CA2420329A1
CA2420329A1 CA002420329A CA2420329A CA2420329A1 CA 2420329 A1 CA2420329 A1 CA 2420329A1 CA 002420329 A CA002420329 A CA 002420329A CA 2420329 A CA2420329 A CA 2420329A CA 2420329 A1 CA2420329 A1 CA 2420329A1
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CA
Canada
Prior art keywords
alkoxy
chlorine
fluorine
alkyl
bromine
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
CA002420329A
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French (fr)
Other versions
CA2420329C (en
Inventor
Klaus-Helmut Mueller
Peter Babczinski
Hans-Joachim Santel
Robert R. Schmidt
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Bayer AG
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Individual
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Publication date
Application filed by Individual filed Critical Individual
Publication of CA2420329A1 publication Critical patent/CA2420329A1/en
Application granted granted Critical
Publication of CA2420329C publication Critical patent/CA2420329C/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
    • 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

Abstract

This invention relates to a triazolinone of the general formula (IIa) (see figure IIa) in which either (1) R1 is C1-C6-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, phenyl, C1-C4-alkoxy or C1-C4-alkoxy carbonyl) or is C3-C4-alkenyloxy and R2 is hydrogen, or represents C1-C6-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy, C1-C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl, or represent C3-C6-cycloalkyl which is optionally substituted by fluorine, chlorine, bromine and/or C1-C4-alkyl, or represents phenyl-C1-C3-alkyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, and/or C1-C4-alkoxycarbonyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, methyl C1-C4-alkoxy, fluorine-and/or chlorine- substituted C1-C3-alkoxy, C1-C4-alkylthio, fluorine- and/or chlorine-substituted C1-C3-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl and/or C1-C4-alkoxycarbonyl; or in which (2) A1 represents and Az represents OCH3 CH(CH3)2 OCH2-CH=CH2 CH3 O-CH2-CH=CH2 C2H5 O-CH2-CH=CH2 C3H7 C3H7 OCH3 OCH3 OCH3 ~ OCH3 OC2H5 The compounds of formula (IIa) are novel intermediates useful in the preparation of herbicidal sulphonylaminocarbonyltriazolinones of the general formula (I)
CA002420329A 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones Expired - Lifetime CA2420329C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEP3934081.3 1989-10-12
DE3934081A DE3934081A1 (en) 1989-10-12 1989-10-12 SULFONYLAMINOCARBONYLTRIAZOLINONE
CA002302058A 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

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002302058A Division 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

Publications (2)

Publication Number Publication Date
CA2420329A1 true CA2420329A1 (en) 1991-04-13
CA2420329C CA2420329C (en) 2005-11-29

Family

ID=6391328

Family Applications (4)

Application Number Title Priority Date Filing Date
CA002027206A Expired - Lifetime CA2027206C (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
CA002420329A Expired - Lifetime CA2420329C (en) 1989-10-12 1990-10-10 Sulphonylaminocarbonyltriazolinones
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

Family Applications Before (2)

Application Number Title Priority Date Filing Date
CA002027206A Expired - Lifetime CA2027206C (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
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

Country Status (13)

Country Link
EP (2) EP0683157B1 (en)
JP (1) JPH03133966A (en)
KR (1) KR0171400B1 (en)
AU (1) AU627080B2 (en)
BR (1) BR9005095A (en)
CA (4) CA2027206C (en)
CZ (1) CZ281525B6 (en)
DE (3) DE3934081A1 (en)
DK (2) DK0683157T3 (en)
ES (2) ES2222457T3 (en)
HU (1) HU218976B (en)
PL (1) PL165494B1 (en)
SK (1) SK280209B6 (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
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
DE19845408A1 (en) * 1998-10-02 2000-04-27 Bayer Ag 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
US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
AU2013363398B2 (en) 2012-12-20 2017-06-01 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
BR112015031291A2 (en) 2013-06-20 2017-07-25 Bayer Cropscience Ag aryl sulfide derivatives and arylalkyl sulfoxide derivatives as acaricides and insecticides
EA201690230A1 (en) 2013-09-06 2016-07-29 Инсепшн 2, Инк. TRIAZOLONE COMPOUNDS AND THEIR APPLICATIONS
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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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
DE68917617T2 (en) * 1988-03-07 1994-12-22 Chugai Pharmaceutical Co Ltd Triazole compounds, processes for their preparation and herbicidal compositions containing them.

Also Published As

Publication number Publication date
KR910007893A (en) 1991-05-30
CA2027206A1 (en) 1991-04-13
CA2302058C (en) 2004-05-25
CA2420329C (en) 2005-11-29
DE3934081A1 (en) 1991-04-18
EP0683157B1 (en) 2004-05-26
AU627080B2 (en) 1992-08-13
CA2027206C (en) 1997-12-23
PL287259A1 (en) 1992-01-27
CZ495090A3 (en) 1996-07-17
ES2222457T3 (en) 2005-02-01
EP0683157A1 (en) 1995-11-22
SK495090A3 (en) 1999-09-10
BR9005095A (en) 1991-09-17
DE59010938D1 (en) 2004-07-01
EP0422469B1 (en) 1996-05-08
AU6459190A (en) 1991-04-18
SK280209B6 (en) 1999-09-10
DK0422469T3 (en) 1996-08-26
CA2189698C (en) 2003-05-06
CA2189698A1 (en) 1991-04-13
DE59010314D1 (en) 1996-06-13
CZ281525B6 (en) 1996-10-16
EP0422469A3 (en) 1992-01-08
EP0422469A2 (en) 1991-04-17
KR0171400B1 (en) 1999-02-01
JPH03133966A (en) 1991-06-07
ES2087107T3 (en) 1996-07-16
HU218976B (en) 2001-01-29
HUT55369A (en) 1991-05-28
HU906419D0 (en) 1991-04-29
DK0683157T3 (en) 2004-09-27
PL165494B1 (en) 1994-12-30
CA2302058A1 (en) 1991-04-13

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