CA2074155A1 - Herbicidal 4-acyl-5-arylisoxazoles - Google Patents

Herbicidal 4-acyl-5-arylisoxazoles

Info

Publication number
CA2074155A1
CA2074155A1 CA002074155A CA2074155A CA2074155A1 CA 2074155 A1 CA2074155 A1 CA 2074155A1 CA 002074155 A CA002074155 A CA 002074155A CA 2074155 A CA2074155 A CA 2074155A CA 2074155 A1 CA2074155 A1 CA 2074155A1
Authority
CA
Canada
Prior art keywords
alkyl
haloalkyl
substituted
co2r3
groups
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
CA002074155A
Other languages
French (fr)
Other versions
CA2074155C (en
Inventor
Paul A. Cain
Susan M. Cramp
Claude Lambert
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.)
Bayer Agriculture Ltd
Original Assignee
Paul A. Cain
Susan M. Cramp
Claude Lambert
Rhone-Poulenc Agriculture Limited
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
Application filed by Paul A. Cain, Susan M. Cramp, Claude Lambert, Rhone-Poulenc Agriculture Limited filed Critical Paul A. Cain
Publication of CA2074155A1 publication Critical patent/CA2074155A1/en
Application granted granted Critical
Publication of CA2074155C publication Critical patent/CA2074155C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • C07D261/08—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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

Abstract

5-Aryl isoxazole derivatives of general formula (I):

wherein:
Ar represents phenyl optionally substituted substituted by one or more groups R2 or pyridyl substituted by one or more groups R2;
R represents :-hydrogen, -CO2R3, -COR4, cyano, halogen, alkyl or haloalkyl;
R1 represents :-alkyl, haloalkyl or cycloalkyl;
R2 represents :-a halogen atom, R4, nitro, -CO2R3, -OR4, -S(O)m R4, -S(O)m R5, -O-(CH2)p-OR4 or an alkyl group substituted by -OR4;
R3 and R4, which may be the same or different, each represent alkyl or haloalkyl;
R5 represents optionally substituted phenyl;
p represents an integer from 1 to 3; and m represents zero, 1 or 2;
-the herbicidal properties of these derivatives and their application to crop protection is described.
CA002074155A 1991-07-17 1992-07-17 Herbicidal 4-acyl-5-arylisoxazoles Expired - Fee Related CA2074155C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919115377A GB9115377D0 (en) 1991-07-17 1991-07-17 New compositions of matter
GB9115377 1991-07-17

Publications (2)

Publication Number Publication Date
CA2074155A1 true CA2074155A1 (en) 1993-01-18
CA2074155C CA2074155C (en) 2003-10-21

Family

ID=10698466

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002074155A Expired - Fee Related CA2074155C (en) 1991-07-17 1992-07-17 Herbicidal 4-acyl-5-arylisoxazoles

Country Status (35)

Country Link
US (2) US5366957A (en)
EP (1) EP0524018B1 (en)
JP (1) JP3122533B2 (en)
KR (1) KR100247841B1 (en)
CN (1) CN1039081C (en)
AT (1) ATE197045T1 (en)
AU (1) AU649550B2 (en)
BG (1) BG61263B1 (en)
BR (1) BR9202701A (en)
CA (1) CA2074155C (en)
CZ (1) CZ224592A3 (en)
DE (1) DE69231510T2 (en)
DK (1) DK0524018T3 (en)
EG (1) EG19781A (en)
ES (1) ES2150910T3 (en)
FI (1) FI923264A (en)
GB (1) GB9115377D0 (en)
GR (1) GR3035151T3 (en)
HU (1) HU212608B (en)
IE (1) IE922320A1 (en)
IL (1) IL102488A (en)
MA (1) MA22594A1 (en)
MX (1) MX9204137A (en)
MY (1) MY108800A (en)
NZ (1) NZ243581A (en)
PL (1) PL168873B1 (en)
PT (1) PT524018E (en)
RO (1) RO109335B1 (en)
RU (1) RU2060251C1 (en)
SK (1) SK224592A3 (en)
TR (1) TR26180A (en)
TW (1) TW221054B (en)
UA (1) UA27725C2 (en)
ZA (1) ZA925376B (en)
ZW (1) ZW11392A1 (en)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9116834D0 (en) * 1991-08-05 1991-09-18 Rhone Poulenc Agriculture Compositions of new matter
KR950704274A (en) * 1992-12-18 1995-11-17 프랑소와 크라티엥 4-benzoyl isoxazole derivatives and their use as herbicides [4-BENZOYL ISOXAZOLES DERIVATIVES AND THEIR USE AS HERBICIDES]
CA2117413C (en) * 1993-07-30 2006-11-21 Neil Geach Herbicidal isoxazole-4-yl-methanone derivatives
GB9316689D0 (en) * 1993-08-11 1993-09-29 Rhone Poulenc Agriculture New compositions of matter
WO1995022904A1 (en) * 1994-02-25 1995-08-31 Rhone Poulenc Agrochimie Pesticidal method
AU1758495A (en) * 1994-02-25 1995-09-11 Rhone-Poulenc Agrochimie New pesticidal method
GB9405234D0 (en) * 1994-03-17 1994-04-27 Rhone Poulenc Agriculture New compositions of matter
DE19548428C1 (en) * 1995-12-22 1997-08-28 Hoechst Ag 2-alkylmerkapto-4- (trifluoromethyl) benzoic acid ester and a process for its preparation
GB9526435D0 (en) * 1995-12-22 1996-02-21 Rhone Poulenc Agriculture New herbicides
WO1997027187A1 (en) * 1996-01-26 1997-07-31 Rhone-Poulenc Agriculture Ltd. Isoxazole and 2-cyano-1,3-diones derivatives and their use as herbicides
WO1997028136A1 (en) * 1996-01-30 1997-08-07 Rhone-Poulenc Agriculture Ltd. Benzoylisoxazoles and 2-cyano-1,3-dione derivatives and their use as herbicides
EP0880498B1 (en) * 1996-02-01 2001-11-21 Aventis Cropscience S.A. Process for preparing diketone compounds
GB9606015D0 (en) * 1996-03-22 1996-05-22 Rhone Poulenc Agriculture New herbicides
US5719103A (en) * 1996-05-02 1998-02-17 Uniroyal Chemical Company, Inc. Powder formulation useful for seed treatment and foliar treatment of plants
US6297198B1 (en) * 1996-05-14 2001-10-02 Syngenta Participations Ag Isoxazole derivatives and their use as herbicides
AU8863798A (en) * 1997-07-18 1999-02-10 Rhone-Poulenc Agriculture Limited 4-benzoyl-isoxazole- and -pyrazole derivatives and 2-cyano 1,3-dione derivativesas herbicides
AU1561599A (en) * 1997-11-12 1999-05-31 Novartis Ag Isoxazole derivatives and their use as herbicides
US6392099B1 (en) 1998-11-19 2002-05-21 Eagleview Technologies, Inc. Method and apparatus for the preparation of ketones
US6369276B1 (en) 1998-11-19 2002-04-09 Eagleview Technologies, Inc. Catalyst structure for ketone production and method of making and using the same
FR2815969B1 (en) 2000-10-30 2004-12-10 Aventis Cropscience Sa TOLERANT PLANTS WITH HERBICIDES BY METABOLIC BYPASS
US6545185B1 (en) 2001-03-29 2003-04-08 Eagleview Technologies, Inc. Preparation of ketones from aldehydes
US6589997B2 (en) * 2001-06-29 2003-07-08 North Shore-Long Island Jewish Health System Small-molecule modulators of hepatocyte growth factor/scatter factor activities
FR2844142B1 (en) * 2002-09-11 2007-08-17 Bayer Cropscience Sa TRANSFORMED PLANTS WITH ENHANCED PRENYLQUINON BIOSYNTHESIS
DE102004029309A1 (en) * 2004-06-17 2005-12-29 Bayer Cropscience Gmbh Pyridinylisoxazoles and their use as herbicides
AR074941A1 (en) 2009-01-07 2011-02-23 Bayer Cropscience Sa TRANSPLASTOMIC PLANTS EXEMPTED FROM SELECTOR MARKER
US8153132B2 (en) 2009-10-30 2012-04-10 Ms Technologies, Inc. Antibodies immunoreactive with mutant hydroxypenylpyruvate dioxygenase
AR080105A1 (en) 2010-02-02 2012-03-14 Bayer Cropscience Ag SOFT TRANSFORMATION USING HYDROPHENYL PIRUVATO DIOXYGENASE (HPPD) INHIBITORS AS SELECTION AGENTS
EA201291165A1 (en) 2010-05-04 2013-05-30 Басф Се PLANTS WITH ENHANCED STABILITY TO HERBICIDES
WO2012074868A2 (en) 2010-12-03 2012-06-07 Ms Technologies, Llc Optimized expression of glyphosate resistance encoding nucleic acid molecules in plant cells
US8648230B2 (en) 2011-03-18 2014-02-11 Ms Technologies, Llc Regulatory regions preferentially expressing in non-pollen plant tissue
AR090418A1 (en) 2012-02-01 2014-11-12 Dow Agrosciences Llc TRANSIT PEPTIDE
AR091901A1 (en) * 2012-07-25 2015-03-11 Amvac Chemical Corp AVAILABLE HERBICIDE COMPOSITIONS AND METHODS OF THE SAME USE
BR102014027466B1 (en) 2013-11-04 2022-09-27 Dow Agrosciences Llc RECOMBINANT NUCLEIC ACID MOLECULE, METHOD FOR PRODUCING A TRANSGENIC PLANT CELL AND USES OF A SOYBEAN PLANT, PART OF A SOYBEAN PLANT, OR A TRANSGENIC SOYBEAN PLANT CELL
CA2928855A1 (en) 2013-11-04 2015-05-07 Dow Agrosciences Llc Optimal maize loci
RU2709734C2 (en) 2013-11-04 2019-12-19 ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи Optimum maize loci
TW201527312A (en) 2013-12-31 2015-07-16 Dow Agrosciences Llc Novel maize ubiquitin promoters
TW201527313A (en) 2013-12-31 2015-07-16 Dow Agrosciences Llc Novel maize ubiquitin promoters
TW201527314A (en) 2013-12-31 2015-07-16 Dow Agrosciences Llc Novel maize ubiquitin promoters
TW201527316A (en) 2013-12-31 2015-07-16 Dow Agrosciences Llc Novel maize ubiquitin promoters
TW201538518A (en) 2014-02-28 2015-10-16 Dow Agrosciences Llc Root specific expression conferred by chimeric gene regulatory elements

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3345375A (en) * 1963-03-25 1967-10-03 Squibb & Sons Inc 3-lower alkyl-5-(4-pyridyl)-isoxazole-4-carbonyl derivatives
US4173650A (en) * 1978-11-03 1979-11-06 American Cyanamid Company Cis-2-benzoyl-3-hydroxy-2-alkenonitriles as anti-inflammatory agents
US4243406A (en) * 1978-12-26 1981-01-06 Monsanto Company 5-Aryl-4-isoxazolecarboxylate-safening agents
GB8920519D0 (en) * 1989-09-11 1989-10-25 Rhone Poulenc Ltd New compositions of matter
GB9025469D0 (en) * 1990-11-22 1991-01-09 Rhone Poulenc Agriculture New compositions of matter
US5334753A (en) * 1992-03-12 1994-08-02 Rhone-Poulenc Agriculture Ltd Processes for preparing ortho-substituted benzoic acids

Also Published As

Publication number Publication date
BR9202701A (en) 1993-03-23
DE69231510T2 (en) 2001-05-17
KR100247841B1 (en) 2000-04-01
RO109335B1 (en) 1995-01-30
MA22594A1 (en) 1993-04-01
MX9204137A (en) 1993-01-01
IL102488A0 (en) 1993-01-14
EP0524018B1 (en) 2000-10-18
FI923264A (en) 1993-01-18
US5424276A (en) 1995-06-13
RU2060251C1 (en) 1996-05-20
HU212608B (en) 1996-09-30
GB9115377D0 (en) 1991-09-04
ZW11392A1 (en) 1993-09-15
SK224592A3 (en) 1995-02-08
MY108800A (en) 1996-11-30
UA27725C2 (en) 2000-10-16
HUT61656A (en) 1993-03-01
AU1951592A (en) 1993-01-21
ES2150910T3 (en) 2000-12-16
US5366957A (en) 1994-11-22
CN1039081C (en) 1998-07-15
ZA925376B (en) 1993-04-02
EG19781A (en) 1996-01-31
EP0524018A1 (en) 1993-01-20
CA2074155C (en) 2003-10-21
IL102488A (en) 1996-03-31
BG61263B1 (en) 1997-04-30
JP3122533B2 (en) 2001-01-09
DK0524018T3 (en) 2000-11-13
GR3035151T3 (en) 2001-04-30
CZ224592A3 (en) 1993-02-17
ATE197045T1 (en) 2000-11-15
AU649550B2 (en) 1994-05-26
KR930002328A (en) 1993-02-23
PT524018E (en) 2001-01-31
PL168873B1 (en) 1996-04-30
DE69231510D1 (en) 2000-11-23
CN1068567A (en) 1993-02-03
PL295288A1 (en) 1993-07-26
IE922320A1 (en) 1993-01-27
FI923264A0 (en) 1992-07-16
JPH05186440A (en) 1993-07-27
TR26180A (en) 1995-02-15
NZ243581A (en) 1995-01-27
TW221054B (en) 1994-02-11

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Legal Events

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EEER Examination request
MKLA Lapsed