CA2025939A1 - Carboxamides of isoxazole- and isothiazole-carboxylic acids - Google Patents

Carboxamides of isoxazole- and isothiazole-carboxylic acids

Info

Publication number
CA2025939A1
CA2025939A1 CA002025939A CA2025939A CA2025939A1 CA 2025939 A1 CA2025939 A1 CA 2025939A1 CA 002025939 A CA002025939 A CA 002025939A CA 2025939 A CA2025939 A CA 2025939A CA 2025939 A1 CA2025939 A1 CA 2025939A1
Authority
CA
Canada
Prior art keywords
substituted
unsubstituted
alkyl
cycloalkyl
chain
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
CA002025939A
Other languages
French (fr)
Other versions
CA2025939C (en
Inventor
Volker Maywald
Wolfgang Freund
Gerhard Hamprecht
Thomas Kuekenhoehner
Peter Plath
Bruno Wuerzer
Karl-Otto Westphalen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
Individual
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
Priority claimed from DE3931627A external-priority patent/DE3931627A1/en
Priority claimed from DE19893933898 external-priority patent/DE3933898A1/en
Application filed by Individual filed Critical Individual
Publication of CA2025939A1 publication Critical patent/CA2025939A1/en
Application granted granted Critical
Publication of CA2025939C publication Critical patent/CA2025939C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/12—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen

Landscapes

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

Abstract

Carboxamides Ia, Ib, Ic and Id (X = 0, S; R1 = H, halogen, substituted or unsubstituted alkyl, substi-tuted or unsubstituted benzyl, alkoxy, alkylthio, haloalkoxy, haloalkyl-thio, substituted or unsubstituted phenyl, substituted or unsubstituted phenoxy or phenylthio, a substituted or unsubstituted 5- or 6-membered heterocyclic radical containing one or two heteroatoms, cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl or cycloalkenyl; R1' - cycloalkyl-substituted alkyl, substituted or unsubstituted alkenyl which may be epoxidized, substituted or unsubstituted cycloalkenyl; R2 = CHO, 4,5-dihydrooxazol-2-yl, COYR5, CONR6R7; Y = 0, S; R5 = H, substituted or unsubstituted alkyl, cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsub-stituted cycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted phenyl, a 5- or 6-membered heterocyclic radical contain-ing up to 3 heteroatoms, benzotriazole, N-phthalimido, tetrahydrophthal-imido, succinimido, maleiimido, 2,2-dimethyl-1,3-dioxolan-4-ylmethyl, 1,3-dioxolan-2-on-4-ylmethyl, and when Y = 0: one equivalent of a cation from the group of the alkali or alkaline earth metals, Mn, Cu, Fe, ammonium and substituted ammonium, a radical -N=CR8R9 or -W-Z; R8, R9 = H, substituted or unsubstituted alkyl, substituted or unsubstituted halo-alkyl, cycloalkyl, alkoxy, furanyl, substituted or unsubstituted phenyl;
R8+R9 = 4-7-membered methylene chain; W = alkylene chain, ethoxyethylene chain, butylene, butynylene chain; Z = a molecular moiety bonded to W in the .omega.-position and is the same as that linked to W in the .alpha.-position of W;
R6=H, alkyl, cycloalkyl; R7=H; alkyl; -C(0-alkyl)=N-H or -C(0-alkyl)=N-alkyl; R6+R7 = 4-5-membered methylene chain; R3 = H, substituted or unsub-stituted alkyl, substituted or unsubstituted cycloalkyl; R4 = H, OH, alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsub-stituted alkynyl, di-(C1-C4)-alkylamino, a substituted or unsubstituted 5-or 6-membered heterocyclic radical containing one or two heteroatoms, sub-stituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
R3+R4 = 4-7-membered methylene chain which may be interrupted by 0, S or N-CH3, or -(CH2) 3-CO-) and their environmentally tolerated salts.
40 The compounds Ia to Id are suitable as herbicides.
CA002025939A 1989-09-22 1990-09-21 Carboxamides of isoxazole- and isothiazole-carboxylic acids Expired - Fee Related CA2025939C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE3931627A DE3931627A1 (en) 1989-09-22 1989-09-22 New amino-carbonyl-substd. iso-thiazole or isoxazole carboxylic acid d
DEP3931627.0 1989-09-22
DEP3933898.3 1989-10-11
DE19893933898 DE3933898A1 (en) 1989-10-11 1989-10-11 New amino-carbonyl-substd. iso-thiazole or isoxazole carboxylic acid d

Publications (2)

Publication Number Publication Date
CA2025939A1 true CA2025939A1 (en) 1991-03-23
CA2025939C CA2025939C (en) 2002-02-19

Family

ID=25885411

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002025939A Expired - Fee Related CA2025939C (en) 1989-09-22 1990-09-21 Carboxamides of isoxazole- and isothiazole-carboxylic acids

Country Status (7)

Country Link
EP (1) EP0418667B1 (en)
JP (1) JPH03130270A (en)
KR (1) KR910006253A (en)
BR (1) BR9004747A (en)
CA (1) CA2025939C (en)
DE (1) DE59009528D1 (en)
HU (1) HU207788B (en)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4108183A1 (en) * 1991-03-14 1992-09-17 Basf Ag ISOXAZOL AND ISOTHIAZOL 5-CARBON ACID AMIDE
DE4108181A1 (en) * 1991-03-14 1992-09-17 Basf Ag ISOXAZOL AND ISOTHIAZOL 5-CARBON ACID AMIDE
DE4201047A1 (en) * 1992-01-17 1993-07-22 Bayer Ag SUBSTITUTED ISOXAZOLE CARBONIC ACID AMIDES
DE4209849A1 (en) * 1992-03-26 1993-09-30 Basf Ag Preparation of isoxazole-3-carboxamide-4-carboxylic acid esters by selective amidation
DE4209848A1 (en) * 1992-03-26 1993-09-30 Basf Ag Process for the preparation of isoxazole-3,4-dicarboxylic acid derivatives
DE4214010A1 (en) * 1992-04-29 1993-11-04 Basf Ag ISOXAZOLE CARBOXYLENEAMIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE
DE4306962A1 (en) * 1993-03-05 1994-09-08 Bayer Ag Oxadiazolecarboxylic acid derivatives
CZ244394A3 (en) * 1993-10-08 1995-06-14 Shell Int Research Herbicidal 1,2,4-oxadiazolecarboxylic acids amides, esters or halides
DE4406209A1 (en) * 1994-02-25 1995-08-31 Basf Ag Cyanoisoxazoles
ATE243204T1 (en) * 1995-08-24 2003-07-15 Basf Ag ISOXAZOLE AND ISOTHIAZOLE-5-CARBOXAMIDE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS HERBICIDES
DE19614859A1 (en) * 1996-04-16 1997-10-23 Basf Ag Herbicidal benzoylisothiazoles
US6297198B1 (en) 1996-05-14 2001-10-02 Syngenta Participations Ag Isoxazole derivatives and their use as herbicides
AU7687998A (en) * 1997-05-19 1998-12-11 Sugen, Inc. Heteroarylcarboxamide compounds active against protein tyrosine kinase related disorders
US6727272B1 (en) * 2002-07-15 2004-04-27 Unitech Pharmaceuticals, Inc. Leflunomide analogs for treating rheumatoid arthritis
ES2368735T3 (en) * 2002-12-23 2011-11-21 4Sc Ag AROMATIC COMPOUNDS AS ANTI-INFLAMMATORY, IMMUNOMODULATING AND ANTIPROLIFERATIVE AGENTS.
US7071355B2 (en) 2002-12-23 2006-07-04 4 Sc Ag Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents
US7365094B2 (en) 2002-12-23 2008-04-29 4Sc Ag Compounds as anti-inflammatory, immunomodulatory and anti-proliferatory agents
ES2393483T3 (en) * 2003-02-11 2012-12-21 Vernalis (R&D) Limited Isoxazole compounds as heat shock protein inhibitors
TW200716576A (en) * 2005-06-07 2007-05-01 Shionogi & Co Heterocyclic derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1
WO2008046072A2 (en) * 2006-10-13 2008-04-17 The Board Of Regents Of The University Of Texas System Chemical inducers of neurogenesis
US8193225B2 (en) 2006-10-13 2012-06-05 The Board Of Regents Of The University Of Texas System Isoxazole amides, derivatives and methods of chemical induction of neurogenesis
US9284749B2 (en) 2012-04-17 2016-03-15 Schlage Lock Company Llc Door lock assembly
SI3233843T1 (en) 2014-12-16 2019-12-31 Novartis Ag Isoxazole hydroxamic acid compounds as lpxc inhibitors
BR112018074983A2 (en) 2016-06-14 2019-03-12 Novartis Ag (r) -4- (5-Cyclopropylethynyl) isoxazol-3-yl) -n-hydroxy-2-methyl-2- (methylsulfonyl) butanamide crystalline form as an antibacterial agent
WO2021183937A1 (en) * 2020-03-13 2021-09-16 Board Of Regents, The University Of Texas System Substituted isoxazoles as selective nav1.7 inhibitors for pain treatment and method of pain treatment

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3409616A (en) * 1966-07-27 1968-11-05 Pfizer & Co C 4-oxo-10-hydroxy-1, 2, 3, 4-tetrahydroanthracene-2-(alpha-amino)acetates
US4890053A (en) * 1988-04-15 1989-12-26 Philip Morris Incorporated Method and apparatus for detecting a missing object in a set of objects

Also Published As

Publication number Publication date
HU207788B (en) 1993-06-28
BR9004747A (en) 1991-09-10
CA2025939C (en) 2002-02-19
HU906009D0 (en) 1991-03-28
KR910006253A (en) 1991-04-29
EP0418667A2 (en) 1991-03-27
DE59009528D1 (en) 1995-09-21
EP0418667A3 (en) 1992-01-08
EP0418667B1 (en) 1995-08-16
HUT55955A (en) 1991-07-29
JPH03130270A (en) 1991-06-04

Similar Documents

Publication Publication Date Title
CA2025939A1 (en) Carboxamides of isoxazole- and isothiazole-carboxylic acids
RU93049322A (en) OXADIASINE DERIVATIVES
EP0355049A3 (en) Heterocyclic compounds
EP0119539A3 (en) Fungicidal agent, substituted glucopyranosyl amine and a method of combating moulds
EP1468683A3 (en) Pharmaceutical composition for oral use with angiotensin-II-antagonistic activity and method of preparing it
CA2027206A1 (en) Sulphonylaminocarbonyltriazolinones
CA2237273A1 (en) Angiogenesis inhibiting pyridazinamines
EP0398692A3 (en) Alkoxyiminoacetamide derivatives and their use as fungicides
DE3369134D1 (en) Substituted 5-trifluoromethyl-1,3,4-thiadiazol-2-yl oxiacetic-acid amides, process for their preparation and their use as herbicides
CA2291246A1 (en) Alkaline ether amine conveyor lubricant
CA2023858A1 (en) (+)-isomers of endoetheno/endoethano-epoxymorphinan derivatives as antitussive agents
RU95113597A (en) Insecticide composition, method of insect control
EP0398084A3 (en) Nitro-substituted heterocyclic compounds
EP0167768A3 (en) Fungicidal agents
EP0974347A4 (en) Antiviral agents
GB9302334D0 (en) Compositions and compounds
EP0333059A3 (en) Azolyl methyl allyl alcohols, and fungicides containing them
EP0978277A4 (en) Antirheumatic agents
EP0332156A3 (en) Cephem compounds and processes for preparation thereof
EP0238943A3 (en) Fungicidal agents based on triazolyl derivatives
EP0373461A3 (en) Benzazoles
EP0330016A3 (en) Azolyl methyl oxiranes and fungicides containing them
DE3784658D1 (en) AGENT FOR ABSCISSION OF PLANT PARTS.
EP0282893A3 (en) Pesticides based on 1,10-phenanthrolines
EP0227046A3 (en) Pyridine derivatives, process for their preparation, agents containing them and their use as pesticides

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed