GB1255650A - Epoxy compounds and a process for the production thereof - Google Patents
Epoxy compounds and a process for the production thereofInfo
- Publication number
- GB1255650A GB1255650A GB5907168A GB5907168A GB1255650A GB 1255650 A GB1255650 A GB 1255650A GB 5907168 A GB5907168 A GB 5907168A GB 5907168 A GB5907168 A GB 5907168A GB 1255650 A GB1255650 A GB 1255650A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- formula
- alkyl
- trans
- epoxy
- 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)
- Securing Of Glass Panes Or The Like (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Earth Drilling (AREA)
Abstract
1,255,650. Esters of unsaturated epoxy acids. F. HOFFMANN-LA ROCHE & CO. A.G. 12 Dec., 1968 [18 Dec., 1967], No. 59071/68. Heading C2C. Novel epoxides of the formula in which R is hydrogen or C 1 _ 6 alkyl, R<SP>1</SP> is hydrogen, C 1 _ 6 alkyl, phenyl or di- (C 1 _ 6 alkyl)- aminoalkyl and A and B are hydrogen or together represent a double bond or an oxygen bridge, provided that when R is hydrogen and A and B, represent ,a double bond R<SP>1</SP> is not hydrogen or a methyl group, are prepared by reacting a ketone of the formula in which A<SP>1</SP> and B<SP>1</SP> are hydrogen or a double bond, with a phosphorane of the formula or with a phosphine oxide or phosphinate of the formula in which R<SP>4</SP>, R<SP>5</SP> and R<SP>6</SP> are aryl or dialkylarriino groups, R<SP>7</SP> and R<SP>8</SP> are aryl, alkoxy or aryloxy groups and R<SP>10</SP> is C 1-6 alkyl, phenyl or di- (C 1 _ 6 alkyl) aminoalkyl, in the presence of a base and an organic solvent and epoxidizing the product obtained either by treatment with an organic peracid or by treatment with N- bromosuccinimide, water and a base, or epoxidizing the ketone of the Formula (II) by the above methods and reacting the resultant 5,6-epoxide with a phosphine oxide or phosphonate of the Formula (IV), in either ease, if desired, hydrolysing the resultant ester to the free acid. The reaction with the phosphorane (III) may be catalysed by an organic acid, e.g. acetic or benzoic acid. Preferred basic catalysts for the reactants (IV) are sodium hydride and sodium methoxide. Examples relate to the preparation of 10,11 -epoxy-3,7, 11 -trimethyldodec - 2 - cis/trans - en - 1 - oic acid ethyl ester, cis/trans - 10,11 - epoxy 3,7,11 - trimethyltrideca - 2,6 - dien - 1 - oic acid methyl and ethyl esters, and 10,11-epoxy-3,7,11- trimethyldodeca - 2 - cis/trans - 6 - trans - dien- 1-oic acid ethyl ester. The novel esters 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 the form of conventional pesticidal compositions. Reference has been directed by the Comptroller to Specification 1,209,903.
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 |
|---|---|
| GB1255650A true GB1255650A (en) | 1971-12-01 |
Family
ID=4428163
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5907168A Expired GB1255650A (en) | 1967-12-18 | 1968-12-12 | Epoxy compounds and a process for the production thereof |
| GB1257431D Expired GB1257431A (en) | 1967-12-18 | 1968-12-12 | |
| GB1250647D Expired GB1250647A (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 |
| GB1256653D Expired GB1256653A (en) | 1967-12-18 | 1968-12-12 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1257431D Expired GB1257431A (en) | 1967-12-18 | 1968-12-12 | |
| GB1250647D Expired GB1250647A (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 |
| GB1256653D Expired GB1256653A (en) | 1967-12-18 | 1968-12-12 |
Country Status (19)
| Country | Link |
|---|---|
| AT (2) | AT294489B (en) |
| BE (2) | BE725578A (en) |
| BR (2) | BR6804902D0 (en) |
| CA (2) | CA942764A (en) |
| CH (3) | CH508613A (en) |
| CS (1) | CS154600B2 (en) |
| DE (2) | DE1814872A1 (en) |
| DK (2) | DK124332B (en) |
| ES (1) | ES361552A1 (en) |
| FR (2) | FR1599304A (en) |
| GB (5) | GB1255650A (en) |
| IE (2) | IE32588B1 (en) |
| IL (2) | IL31196A (en) |
| IT (2) | IT988509B (en) |
| NL (2) | NL6818045A (en) |
| NO (2) | NO126226B (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 |
|---|---|---|---|---|
| ZA712023B (en) * | 1970-03-31 | 1971-12-29 | Hoffmann La Roche | Pest control agent |
| US4456603A (en) * | 1979-08-14 | 1984-06-26 | Eisai Co., Ltd. | Polyprenylcarboxylic acid amides useful for treating liver dysfunction |
-
1967
- 1967-12-18 CH CH1779667A patent/CH508613A/en not_active IP Right Cessation
- 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
-
1968
- 1968-12-02 IL IL31196A patent/IL31196A/en unknown
- 1968-12-03 CA CA036,725A patent/CA942764A/en not_active Expired
- 1968-12-03 CA CA036724A patent/CA933528A/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 GB5907168A patent/GB1255650A/en not_active Expired
- 1968-12-12 GB GB1257431D patent/GB1257431A/en not_active Expired
- 1968-12-12 GB GB1250647D patent/GB1250647A/en not_active Expired
- 1968-12-12 GB GB2455770A patent/GB1263651A/en not_active Expired
- 1968-12-12 GB GB1256653D patent/GB1256653A/en not_active Expired
- 1968-12-16 DE DE19681814872 patent/DE1814872A1/en active Pending
- 1968-12-16 NL NL6818045A patent/NL6818045A/xx unknown
- 1968-12-16 DE DE19681814875 patent/DE1814875A1/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 SE SE1727168A patent/SE376919B/xx unknown
- 1968-12-17 AT AT1225568A patent/AT294489B/en active
- 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 DK DK617868A patent/DK124332B/en unknown
- 1968-12-17 CS CS856268A patent/CS154600B2/cs unknown
- 1968-12-17 DK DK617968A patent/DK126940B/en unknown
- 1968-12-17 NO NO05051/68A patent/NO126226B/no unknown
- 1968-12-17 NO NO5050/68A patent/NO124992B/no unknown
- 1968-12-17 ES ES361552A patent/ES361552A1/en not_active Expired
- 1968-12-17 BE BE725578D patent/BE725578A/xx unknown
- 1968-12-17 AT AT1225668A patent/AT291674B/en active
- 1968-12-17 BR BR20490168A patent/BR6804901D0/en unknown
- 1968-12-17 SE SE1727268A patent/SE362245B/xx unknown
- 1968-12-17 BE BE725579D patent/BE725579A/xx unknown
- 1968-12-18 NL NL6818162A patent/NL6818162A/xx unknown
- 1968-12-18 FR FR1599302D patent/FR1599302A/fr not_active Expired
- 1968-12-18 TR TR1699968A patent/TR16999A/en unknown
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