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GB1377319A - Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides - Google Patents

Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides

Info

Publication number
GB1377319A
GB1377319A GB3157773A GB3157773A GB1377319A GB 1377319 A GB1377319 A GB 1377319A GB 3157773 A GB3157773 A GB 3157773A GB 3157773 A GB3157773 A GB 3157773A GB 1377319 A GB1377319 A GB 1377319A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
halogen
dione
formula
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.)
Expired
Application number
GB3157773A
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
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB1377319A publication Critical patent/GB1377319A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

1377319 Substituted cyclohexane-2,6-dione and carboxylic acid analides and thioanalides and their use as insecticides, acaricides and fungicides BAYER AG 3 July 1973 [4 July 1972 2 Jan 1973 3 April 1973] 31577/73 Heading C2C The invention comprises compounds of Formula I: in which R<SP>1</SP>, R<SP>2</SP>, R<SP>5</SP> and R<SP>6</SP> are each hydrogen, halogen, carbalkoxy, or alkyl; R<SP>3</SP> and R<SP>4</SP> are each hydrogen, alkyl, alkenyl, cycloalkyl, or optionally substituted phenyl (with the proviso that R<SP>3</SP> and R<SP>4</SP> can both be hydrogen only if at least one of R<SP>1</SP>, R<SP>2</SP>, R<SP>5</SP> and R<SP>6</SP> is halogen, alkyl or carbalkoxy), or R<SP>4</SP> is hydrogen and R<SP>3</SP> is furyl, or R<SP>3</SP> and R<SP>4</SP> conjointly form an alkylene bridge with at most 5 members which forms a spiro bond with the adjoining carbon atom; R<SP>7</SP> is halogen, nitro, nitrile, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkoxycarbonyl, alkylsulphonyl, alkylsulphoxyl or optionally substituted aryloxy; R<SP>8</SP> is hydrogen, halogen, nitro, nitrile, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkoxycarbonyl or alkyluncondensed gas from the distillation apparatus at 12 and adding to the distillation vessel, the sulphonyl; n is an integer from 1 to 4, or R<SP>7</SP> and R<SP>8</SP>, with the proviso that they are in the orchoposition to one another and n represents 1 jointly form a fused aromatic or heteroaromatic ring system which can optionally be substituted, and X is oxygen or sulphur. These compounds ar obtained by reacting a cyclohexane-2,6-dione of Formula II: wherein R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> have the meanings stated above, M is hydrogen or one equivalent of a cation, with an isocyanate or isothiocyanate of Formula III: in which R<SP>7</SP>, R<SP>8</SP>, n, and X have the meanings stated above, optionally in the presence of an acid-binding agent and/or a diluent. Many compounds are specified in Tables 1-3. The invention also comprises an insecticidal, fungicidal or acaricidal composition containing as an active ingredient a compound according to Formula I, in admixture with a solid or liquified gaseous diluent or carrier in admixture with a liquid diluent or carrier containing a surface-active agent.
GB3157773A 1972-07-04 1973-07-03 Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides Expired GB1377319A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2232730A DE2232730A1 (en) 1972-07-04 1972-07-04 SUBSTITUTED CYCLOHEXANE-2,6-Dione-1CARBONIC ANILIDES AND THIOANILIDES, METHOD FOR THEIR MANUFACTURING AND USE AS INSECTICIDES, ACARICIDES AND FUNGICIDES

Publications (1)

Publication Number Publication Date
GB1377319A true GB1377319A (en) 1974-12-11

Family

ID=5849630

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3157773A Expired GB1377319A (en) 1972-07-04 1973-07-03 Cyclohexane-2,6-dione-1-carboxylic acid anilides and thioanilides a process for their preparation and their use as insecticides acaricides and fungicides

Country Status (14)

Country Link
JP (2) JPS49100225A (en)
AU (1) AU5760873A (en)
BE (1) BE801842A (en)
BR (1) BR7304833D0 (en)
CH (1) CH568963A5 (en)
DE (1) DE2232730A1 (en)
FR (1) FR2190806B1 (en)
GB (1) GB1377319A (en)
IE (1) IE37868B1 (en)
IL (1) IL42638A0 (en)
IT (1) IT990867B (en)
LU (1) LU67692A1 (en)
NL (1) NL7309198A (en)
ZA (1) ZA734470B (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2601780B2 (en) * 1976-01-20 1979-07-26 Bayer Ag, 5090 Leverkusen N-phenyl-N'-benzoylureas, process for their preparation and their use as insecticides
US4584013A (en) * 1983-05-18 1986-04-22 Ciba-Geigy Corporation Cyclohexanedionecarboxylic acid derivatives with herbicidal and plant growth regulating properties
MX5738A (en) * 1983-05-18 1993-10-01 Ciba Geigy Ag DERIVATIVES OF CYCLOHEXANDIONCARBOXILICO ACID AND PROCEDURE FOR ITS PREPARATION
DE3569104D1 (en) * 1984-10-02 1989-05-03 Ciba Geigy Ag Process for the preparation of cyclohexane dione carboxylic-acid derivatives with a herbicidal and plant-growth regulating effect
WO2023127808A1 (en) * 2021-12-28 2023-07-06 株式会社Adeka Arylcyclohexanedione derivative or salt thereof, pest control agent containing said compound, and method for using same
CN118613467A (en) * 2021-12-28 2024-09-06 株式会社艾迪科 Arylcyclohexanedione derivatives and salts thereof, pest control agents containing the same and methods of use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1327154A (en) * 1971-01-15 1973-08-15 American Cyanamid Co Dioxocyclohexenecarboxanilide insecticides and acaricides

Also Published As

Publication number Publication date
FR2190806B1 (en) 1977-02-18
LU67692A1 (en) 1973-08-02
IL42638A0 (en) 1973-10-25
BR7304833D0 (en) 1974-08-15
AU5760873A (en) 1975-01-09
JPS49100225A (en) 1974-09-21
IE37868B1 (en) 1977-10-26
IT990867B (en) 1975-07-10
NL7309198A (en) 1974-01-08
BE801842A (en) 1974-01-03
FR2190806A1 (en) 1974-02-01
IE37868L (en) 1974-01-04
ZA734470B (en) 1974-05-29
DE2232730A1 (en) 1974-01-24
JPS49100054A (en) 1974-09-20
CH568963A5 (en) 1975-11-14

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees