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filingDate 1968-12-12^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1971-12-15^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1256653-A
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.
priorityDate 1967-12-18^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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