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 fungicidesInfo
- 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
Links
- 230000000895 acaricidal effect Effects 0.000 title abstract 3
- 239000000642 acaricide Substances 0.000 title abstract 2
- 239000000417 fungicide Substances 0.000 title abstract 2
- 239000002917 insecticide Substances 0.000 title abstract 2
- UDJIPUWKNJRKBB-UHFFFAOYSA-N 2,6-dioxo-N-phenylcyclohexane-1-carboxamide Chemical class O=C(Nc1ccccc1)C1C(=O)CCCC1=O UDJIPUWKNJRKBB-UHFFFAOYSA-N 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 239000003085 diluting agent Substances 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 abstract 2
- 238000004821 distillation Methods 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
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)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (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.
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4458817A4 (en) * | 2021-12-28 | 2025-11-26 | Adeka Corp | Aryldihydropyran derivative or salt thereof, pesticides thereof and methods for using thereof |
Families Citing this family (6)
| 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 |
| EP0126713B1 (en) * | 1983-05-18 | 1989-01-18 | Ciba-Geigy Ag | Cyclohexanedione-carboxylic-acid derivatives having a herbicidal and plant growth regulating activity |
| MX5738A (en) * | 1983-05-18 | 1993-10-01 | Ciba Geigy Ag | DERIVATIVES OF CYCLOHEXANDIONCARBOXILICO ACID AND PROCEDURE FOR ITS PREPARATION |
| EP0177450B1 (en) * | 1984-10-02 | 1989-03-29 | Ciba-Geigy Ag | Process for the preparation of cyclohexane dione carboxylic-acid derivatives with a herbicidal and plant-growth regulating effect |
| EP4458807A4 (en) * | 2021-12-28 | 2026-02-11 | Adeka Corp | ARYLCYCLOHEXANEDIONE DERIVATIVE OR SALT OF IT, PEST CONTROL AGENT OF IT AND METHOD FOR USE OF IT |
| CA3244680A1 (en) * | 2021-12-28 | 2025-06-13 | Nihon Nohyaku Co., Ltd. | Arylcyclohexanedione derivative or salt thereof, pest control agent containing said compound, and method for using same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1327154A (en) * | 1971-01-15 | 1973-08-15 | American Cyanamid Co | Dioxocyclohexenecarboxanilide insecticides and acaricides |
-
1972
- 1972-07-04 DE DE2232730A patent/DE2232730A1/en active Pending
-
1973
- 1973-05-29 LU LU67692A patent/LU67692A1/xx unknown
- 1973-06-29 BR BR4833/73A patent/BR7304833D0/en unknown
- 1973-07-02 AU AU57608/73A patent/AU5760873A/en not_active Expired
- 1973-07-02 IL IL42638A patent/IL42638A0/en unknown
- 1973-07-02 IT IT26104/73A patent/IT990867B/en active
- 1973-07-02 CH CH963873A patent/CH568963A5/xx not_active IP Right Cessation
- 1973-07-02 NL NL7309198A patent/NL7309198A/xx unknown
- 1973-07-03 IE IE1104/73A patent/IE37868B1/en unknown
- 1973-07-03 ZA ZA734470A patent/ZA734470B/en unknown
- 1973-07-03 BE BE133061A patent/BE801842A/en unknown
- 1973-07-03 GB GB3157773A patent/GB1377319A/en not_active Expired
- 1973-07-04 JP JP48074948A patent/JPS49100225A/ja active Pending
- 1973-07-04 FR FR737324599A patent/FR2190806B1/fr not_active Expired
- 1973-07-04 JP JP48074947A patent/JPS49100054A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4458817A4 (en) * | 2021-12-28 | 2025-11-26 | Adeka Corp | Aryldihydropyran derivative or salt thereof, pesticides thereof and methods for using thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA734470B (en) | 1974-05-29 |
| IE37868L (en) | 1974-01-04 |
| CH568963A5 (en) | 1975-11-14 |
| BR7304833D0 (en) | 1974-08-15 |
| NL7309198A (en) | 1974-01-08 |
| JPS49100225A (en) | 1974-09-21 |
| BE801842A (en) | 1974-01-03 |
| LU67692A1 (en) | 1973-08-02 |
| IL42638A0 (en) | 1973-10-25 |
| IT990867B (en) | 1975-07-10 |
| AU5760873A (en) | 1975-01-09 |
| FR2190806A1 (en) | 1974-02-01 |
| JPS49100054A (en) | 1974-09-20 |
| IE37868B1 (en) | 1977-10-26 |
| FR2190806B1 (en) | 1977-02-18 |
| DE2232730A1 (en) | 1974-01-24 |
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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 |