GB1256653A - - Google Patents
Info
- Publication number
- GB1256653A GB1256653A GB1256653DA GB1256653A GB 1256653 A GB1256653 A GB 1256653A GB 1256653D A GB1256653D A GB 1256653DA GB 1256653 A GB1256653 A GB 1256653A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- epoxy
- hydrogen
- oic acid
- trans
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/287—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
- C07D303/40—Compounds containing oxirane rings with hydrocarbon 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 by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
- C07D303/46—Compounds containing oxirane rings with hydrocarbon 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 by amide or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epoxy Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Earth Drilling (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Securing Of Glass Panes Or The Like (AREA)
Abstract
1,256,653. Unsaturated epoxyamides. F. HOFFMANN-LA ROCHE & CO. A.G. 12 Dec., 1968 [18 Dec., 1967], No. 24558/70. Divided out of 1,255,650. Heading C2C. Novel epoxides of the formula in which R is hydrogen or C 1-6 alkyl, R<SP>1</SP> and R<SP>2</SP> are each hydrogen or C 1-6 alkyl or together complete a 5- or 6-membered ring which may contain a further nitrogen or oxygen or sulphur atom and A and B are hydrogen or together represent a carbon-carbon bond or an oxygen bridge, are prepared either by reacting a ketone of the formula in which A<SP>1</SP> and B<SP>1</SP> are hydrogen or together represent a carbon-carbon bond, with a phosphorane of the formula or with a phosphine or phosphonate of the formula in which R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> are aryl or dialkylamino groups, R<SP>7</SP> and R<SP>8</SP> are aryl, alkoxy or aryloxy groups and X<SP>1</SP> is -CO.OR<SP>10</SP> or -CO.NR<SP>1</SP>R<SP>2</SP>, where R<SP>10</SP> is C 1-6 alkyl or phenyl, in the presence of a base and an organic solvent and, where necessary after transforming any product containing an alkoxycarbonyl or phenyloxycarbonyl group in a product containing an aminocarbonyl group by saponification, conversion to the acid halide and reaction with ammonia or appropriate amine, and epoxidizing the product with an organic peracid or by treatment with N-bromosuccinimide, water and a base, or converting the ketone of the Formula II to an epoxide by the above methods and reacting the epoxide with a phosphine oxide or phosphonate IV in which X<SP>1</SP> is -CONR<SP>1</SP>R<SP>2</SP> in the presence of a base and an organic solvent. Examples relate to the preparation of amides derived from 10,11 - epoxy - 3,7,11 - trimethyldodec - 2 - cis/trans - en - 1 - oic acid, 10,11- epoxy - 3,7,11 - trimethyltrideca - 2 - en - 1 - oic acid, 10,11 - epoxy - 3,7,11 - trimethyldodeca-2- cis/trans, 6 - trans - dien - 1 - oic acid and 10,11 - epoxy - 3,7,11 - trimethyltrideca - 2,6- dien - 1 - oic acid and ammonia, diethylamine and isobutylamine, including intermediate compounds. The novel amides interfere with the hormonal system-of arthropods, particularly insects, and can be used to control such pests by disrupting metamorphosis and the sequence of generations. The compounds are used in conventional pesticidal forms to protect textiles, seeds, grain and plants from insect attack. Reference has been directed by the Comptroller to Specification 1,209,905.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1779667A CH508613A (en) | 1967-12-18 | 1967-12-18 | Process for the preparation of epoxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1256653A true GB1256653A (en) | 1971-12-15 |
Family
ID=4428163
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1250647D Expired GB1250647A (en) | 1967-12-18 | 1968-12-12 | |
| GB1257431D Expired GB1257431A (en) | 1967-12-18 | 1968-12-12 | |
| GB1256653D Expired GB1256653A (en) | 1967-12-18 | 1968-12-12 | |
| GB2455770A Expired GB1263651A (en) | 1967-12-18 | 1968-12-12 | Epoxy compounds and a process for the production thereof |
| GB5907168A Expired GB1255650A (en) | 1967-12-18 | 1968-12-12 | Epoxy compounds and a process for the production thereof |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1250647D Expired GB1250647A (en) | 1967-12-18 | 1968-12-12 | |
| GB1257431D Expired GB1257431A (en) | 1967-12-18 | 1968-12-12 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2455770A Expired GB1263651A (en) | 1967-12-18 | 1968-12-12 | Epoxy compounds and a process for the production thereof |
| GB5907168A Expired GB1255650A (en) | 1967-12-18 | 1968-12-12 | Epoxy compounds and a process for the production thereof |
Country Status (19)
| Country | Link |
|---|---|
| AT (2) | AT294489B (en) |
| BE (2) | BE725578A (en) |
| BR (2) | BR6804902D0 (en) |
| CA (2) | CA933528A (en) |
| CH (3) | CH544487A (en) |
| CS (1) | CS154600B2 (en) |
| DE (2) | DE1814875A1 (en) |
| DK (2) | DK126940B (en) |
| ES (1) | ES361552A1 (en) |
| FR (2) | FR1599304A (en) |
| GB (5) | GB1250647A (en) |
| IE (2) | IE32588B1 (en) |
| IL (2) | IL31196A (en) |
| IT (2) | IT988509B (en) |
| NL (2) | NL6818045A (en) |
| NO (2) | NO124992B (en) |
| PH (1) | PH9348A (en) |
| SE (2) | SE376919B (en) |
| TR (1) | TR16999A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL36505A0 (en) * | 1970-03-31 | 1971-11-29 | Sparamedica Ag | Pest control agents containing terpenoid and/or propargyl derivatives |
| US4456603A (en) * | 1979-08-14 | 1984-06-26 | Eisai Co., Ltd. | Polyprenylcarboxylic acid amides useful for treating liver dysfunction |
-
1967
- 1967-12-18 CH CH360370A patent/CH544487A/en not_active IP Right Cessation
- 1967-12-18 CH CH360470A patent/CH544488A/en not_active IP Right Cessation
- 1967-12-18 CH CH1779667A patent/CH508613A/en not_active IP Right Cessation
-
1968
- 1968-12-02 IL IL31196A patent/IL31196A/en unknown
- 1968-12-03 CA CA036724A patent/CA933528A/en not_active Expired
- 1968-12-03 CA CA036,725A patent/CA942764A/en not_active Expired
- 1968-12-04 IL IL31224A patent/IL31224A/en unknown
- 1968-12-05 PH PH9802*UA patent/PH9348A/en unknown
- 1968-12-08 FR FR1599304D patent/FR1599304A/fr not_active Expired
- 1968-12-12 GB GB1250647D patent/GB1250647A/en not_active Expired
- 1968-12-12 GB GB1257431D patent/GB1257431A/en not_active Expired
- 1968-12-12 GB GB1256653D patent/GB1256653A/en not_active Expired
- 1968-12-12 GB GB2455770A patent/GB1263651A/en not_active Expired
- 1968-12-12 GB GB5907168A patent/GB1255650A/en not_active Expired
- 1968-12-16 DE DE19681814875 patent/DE1814875A1/en active Pending
- 1968-12-16 NL NL6818045A patent/NL6818045A/xx unknown
- 1968-12-16 DE DE19681814872 patent/DE1814872A1/en active Pending
- 1968-12-16 IE IE1520/68A patent/IE32588B1/en unknown
- 1968-12-16 IE IE1521/68A patent/IE32897B1/en unknown
- 1968-12-17 IT IT2522268A patent/IT988509B/en active
- 1968-12-17 BR BR20490268A patent/BR6804902D0/en unknown
- 1968-12-17 IT IT2522368A patent/IT947013B/en active
- 1968-12-17 BE BE725578D patent/BE725578A/xx unknown
- 1968-12-17 DK DK617968A patent/DK126940B/en unknown
- 1968-12-17 SE SE1727168A patent/SE376919B/xx unknown
- 1968-12-17 CS CS856268A patent/CS154600B2/cs unknown
- 1968-12-17 SE SE1727268A patent/SE362245B/xx unknown
- 1968-12-17 AT AT1225568A patent/AT294489B/en active
- 1968-12-17 BR BR20490168A patent/BR6804901D0/en unknown
- 1968-12-17 DK DK617868A patent/DK124332B/en unknown
- 1968-12-17 BE BE725579D patent/BE725579A/xx unknown
- 1968-12-17 ES ES361552A patent/ES361552A1/en not_active Expired
- 1968-12-17 AT AT1225668A patent/AT291674B/en active
- 1968-12-17 NO NO5050/68A patent/NO124992B/no unknown
- 1968-12-17 NO NO05051/68A patent/NO126226B/no unknown
- 1968-12-18 TR TR1699968A patent/TR16999A/en unknown
- 1968-12-18 NL NL6818162A patent/NL6818162A/xx unknown
- 1968-12-18 FR FR1599302D patent/FR1599302A/fr not_active Expired
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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 |