CA2256508A1 - 3-cyanoaryl-pyrazoles et leur utilisation comme herbicides - Google Patents

3-cyanoaryl-pyrazoles et leur utilisation comme herbicides Download PDF

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Publication number
CA2256508A1
CA2256508A1 CA002256508A CA2256508A CA2256508A1 CA 2256508 A1 CA2256508 A1 CA 2256508A1 CA 002256508 A CA002256508 A CA 002256508A CA 2256508 A CA2256508 A CA 2256508A CA 2256508 A1 CA2256508 A1 CA 2256508A1
Authority
CA
Canada
Prior art keywords
cyano
methyl
chloro
phenyl
fluoro
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.)
Abandoned
Application number
CA002256508A
Other languages
English (en)
Inventor
Otto Schallner
Karl-Heinz Linker
Karl-Julius Reubke
Markus Dollinger
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 AG
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
Application filed by Individual filed Critical Individual
Publication of CA2256508A1 publication Critical patent/CA2256508A1/fr
Abandoned legal-status Critical Current

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Classifications

    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux 3-cyanoaryl-pyrazoles de formule générale (I), dans laquelle Q représente oxygène (O), soufre (S), SO ou SO¿2?; R?1¿ représente hydrogène ou l'un des radicaux suivants éventuellement substitués: alkyle, alcényle, alcynyle, cycloalkyle ou cycloalkylalkyle; R?2¿ représente hydrogène ou l'un des radicaux suivants éventuellement substitués: alkyle, alcényle, alcynyle, cycloalkyle ou cycloalkylalkyle; R?3¿ représente hydrogène, halogène ou alkyle éventuellement substitué; R?4¿ représente hydrogène ou halogène; et R?5¿ représente hydrogène, hydroxy, mercapto, amino, hydroxyamino, halogène ou l'un des radicaux suivants: -Q-R?6¿, -NH-R?6¿, -NH-O-R?6¿, -NH-SO¿2?-R?6¿, -N(SO¿2?-R?6¿)¿2?, -CQ?1¿-R?6¿, -CQ?1¿-Q?2¿-R?6¿, -CQ?1¿-NH-R?6¿, -Q?2¿-CQ?1¿-R?6¿, -NH-CQ?1¿-R?6¿, -N(SO¿2?-R?6¿)(CQ?1¿-R?6¿), -Q?2¿-CQ?1¿-Q?2¿-R?6¿, -NH-CQ?1¿-Q?2¿-R?6¿ ou -Q?2¿-CQ?1¿-NH-R?6¿, où Q?1¿ et Q?2¿ représente oxygène ou soufre, et R?6¿ représente l'un des radicaux suivants éventuellement substitués: alkyle, alcényle, alcynyle, cycloalkyle, cycloalkylalkyle, aryle, arylalkyle, hétérocyclyle ou hétérocyclylalkyle; les composés 1-méthyl-3-(4-cyano-2-fluorophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluorophényl)-4-bromo-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-nitrophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-éthylsulfonylaminophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-éthoxycarbonylméthoxyphényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-chlorophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-méthylthiophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-aminophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-hydroxyphényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-chlorophényl)-4-chloro-5-difluorométhoxy-pyrazole, 1-méthyl-3-(4-cyano-2-fluoro-5-aminosulfonylphényl)-4-chloro-5-difluorométhoxy-pyrazole et 1-méthyl-3-(4-cyano-2-fluoro-5-fluorosulfonylphényl)-4-chloro-5-difluorométhoxy-pyrazole étant exclus par renonciation. L'invention concerne également un procédé pour la production desdits composés, de nouveaux produits intermédiaires et l'utilisation des 3-cyanoarylpyrazoles comme herbicides.
CA002256508A 1996-06-03 1997-05-21 3-cyanoaryl-pyrazoles et leur utilisation comme herbicides Abandoned CA2256508A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1996122189 DE19622189A1 (de) 1996-06-03 1996-06-03 3-Cyanaryl-pyrazole
DE19622189.7 1996-06-03
PCT/EP1997/002580 WO1997046535A1 (fr) 1996-06-03 1997-05-21 3-cyanoaryl-pyrazoles et leur utilisation comme herbicides

Publications (1)

Publication Number Publication Date
CA2256508A1 true CA2256508A1 (fr) 1997-12-11

Family

ID=7795979

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002256508A Abandoned CA2256508A1 (fr) 1996-06-03 1997-05-21 3-cyanoaryl-pyrazoles et leur utilisation comme herbicides

Country Status (8)

Country Link
EP (1) EP0906285A1 (fr)
JP (1) JP2000512275A (fr)
CN (1) CN1227545A (fr)
AU (1) AU2958597A (fr)
BR (1) BR9709521A (fr)
CA (1) CA2256508A1 (fr)
DE (1) DE19622189A1 (fr)
WO (1) WO1997046535A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19838706A1 (de) 1998-08-26 2000-03-02 Bayer Ag Substituierte 3-Aryl-pyrazole
IT1313601B1 (it) 1999-08-05 2002-09-09 Isagro Ricerca Srl Fenilpirazoli ad attivita' erbicida
DE19937772A1 (de) 1999-08-10 2001-02-15 Bayer Ag Substituierte Heterocyclyl-2GH-chromene
DE10032633A1 (de) * 2000-07-05 2002-01-17 Bayer Ag Verfahren zum Auffinden von Hemmstoffen der Protoporphyrinogen-Oxidase
GB0016787D0 (en) 2000-07-07 2000-08-30 Pfizer Ltd Compounds useful in therapy
WO2002055504A1 (fr) * 2001-01-16 2002-07-18 Basf Aktiengesellschaft Procede de production de 1-alkyl-3-aryl-5-difluoromethoxy-1h-pyrazoles
CN101870677A (zh) * 2010-06-28 2010-10-27 大连理工大学 一种5-芳甲氧基苯基吡唑类化合物及其制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2537047A1 (de) * 1975-08-20 1977-03-03 Bayer Ag Vinylthionophosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
US4546113A (en) * 1983-04-14 1985-10-08 Pfizer Inc. Antiprotozoal diamidines
GB8703975D0 (en) * 1987-02-20 1987-03-25 Wellcome Found Pesticidal compounds
PT656348E (pt) * 1993-12-03 2000-10-31 Hoffmann La Roche Derivados do acido acetico como medicamentos
DE4417837A1 (de) * 1994-05-20 1995-11-23 Basf Ag Substituierte 3-Phenylpyrazole
GB9413237D0 (en) * 1994-07-01 1994-08-24 Zeneca Ltd Herbicides
EP0708107B1 (fr) * 1994-10-20 2001-02-28 Shin-Etsu Chemical Co., Ltd. Nouveaux composés de silacyclohexane, une composition de cristaux liquides les comprenant et un dispositif à cristaux liquides contenant ladite composition
GB9422667D0 (en) * 1994-11-10 1995-01-04 Zeneca Ltd Herbicides
EP0832070A1 (fr) * 1995-06-15 1998-04-01 Novartis AG Nouveaux herbicides

Also Published As

Publication number Publication date
DE19622189A1 (de) 1997-12-04
JP2000512275A (ja) 2000-09-19
WO1997046535A1 (fr) 1997-12-11
EP0906285A1 (fr) 1999-04-07
BR9709521A (pt) 1999-08-10
CN1227545A (zh) 1999-09-01
AU2958597A (en) 1998-01-05

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Legal Events

Date Code Title Description
FZDE Discontinued