Halogen In Acid Moiety Patents (Class 560/226)
  • Patent number: 4665226
    Abstract: An improved two-step process for preparing 5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid (gemfibrozil) which regularly affords gembibrozil in overall yields in excess of 80% comprises reacting an alkali metal salt of a lower alkyl ester of 2-methylpropanoic acid with 1,3-dibromopropane or 1-bromo-3-chloropropane in a polar aprotic solvent such as tetrahydrofuran, and then reacting the intermediate thus formed with an alkali metal salt of 2,5-dimethylphenol in a mixed toluene/dimethylsulfoxide solvent system.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: May 12, 1987
    Assignee: Warner-Lambert Company
    Inventor: Francis R. Kearney
  • Patent number: 4647691
    Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4640802
    Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.
    Type: Grant
    Filed: July 7, 1982
    Date of Patent: February 3, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4638000
    Abstract: Novel condensed seven-membered ring compounds of the formula: ##STR1## [wherein R.sup.1 and R.sup.2 are independently hydrogen, halogen, trifluoromethyl, lower alkyl or lower alkoxy, or both jointly form tri- or tetramethylene; R.sup.3 and R.sup.5 are independently hydrogen, lower alkyl or aralkyl; R.sup.4 is hydrogen or lower alkyl; R.sup.6 is a condensed or non-condensed hetero-alicyclic containing at least one atom of N, O and S as a ring-forming atom which may be substituted; A is an alkylene chain; n is 1 or 2] and salts thereof.These compounds exhibit inhibitory activity on angiotensin converting enzyme and so forth, and are of value as an agent for diagnosis, prevention and treatment of circulatory diseases, such as hypertension, cardiopathy and cerebral apoploxy.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: January 20, 1987
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Kohei Nishikawa, Katsumi Ito
  • Patent number: 4609673
    Abstract: The present invention provides carboxylic acid derivatives of the general formula: ##STR1## wherein R is a hydrogen atom, alkyl, a metal cation or an ammonium or alkylammonium ion, R.sub.1 is a hydrogen atom, a hydroxyl group or an alkyl, O-alkyl,O-benzyl or O-acyl radical, R.sub.2 is a hydrogen atom or an alkyl, aryl or aralkyl radical, n is 0, 1 or 2 and R.sub.
    Type: Grant
    Filed: December 18, 1984
    Date of Patent: September 2, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Hermann Eggerer, Bernd Hagenbruch, Tran G. Nguyen, Karlheinz Stegmeier, Johannes Pill
  • Patent number: 4582526
    Abstract: Carbamic acid ester compounds of the formula ##STR1## wherein A represents the group (a) or (b) ##STR2## wherein R.sup.1 -R.sup.8, X and Y are as defined hereinafter, processes for their preparation, herbicidal compositions containing these compounds and methods for the use of the compounds and the herbicidal compositions are disclosed.
    Type: Grant
    Filed: December 9, 1983
    Date of Patent: April 15, 1986
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Jean Wenger, Rene Zurfluh
  • Patent number: 4546200
    Abstract: 2,2-Dinitrobutane-1,4-diol and 4-monoesters thereof.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: October 8, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, Horst G. Adolph
  • Patent number: 4541858
    Abstract: Novel chlorinated phosphorylmethylcarbonyl derivatives of the formula ##STR1## in which R.sup.1 represents an optionally substituted radical from the series comprising alkyl, aryl, aralkyl, alkoxy and aralkoxy andR.sup.2 represents an optionally substituted radical from the series comprising alkoxy and aralkoxy, orR.sup.1 and R.sup.2 together represent an alkanedioxy radical,X represents hydrogen or chlorine andR.sup.3 represents the grouping ##STR2## in which R.sup.4 represents hydrogen or optionally substituted alkyl andR.sup.5 represents optionally substituted alkoxycarbonyl radical or an optionally substituted pyrazolyl radical; orif X represents chlorine, R.sup.3 also may represent optionally substituted radical from the series comprising alkyl, cycloalkyl, alkylamino and cycloalkylamino,which possesses fungicidal activity as well as herbicidal activity, but not against rice. Some intermediates are also new.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: September 17, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Theodor Pfister, Ludwig Eue, Robert R. Schmidt, Gerd Hanssler
  • Patent number: 4540810
    Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: September 10, 1985
    Assignee: Texaco Development Corporation
    Inventor: John F. Knifton
  • Patent number: 4539424
    Abstract: Linear esters, e.g., alkyl adipates, are facilely prepared by reacting an alcohol and carbon monoxide with a monoolefin, in the presence of cobalt, optionally hydrogen, and a tertiary nitrogen base, and in a reaction solvent which comprises a 5- or 6-membered monoheterocycle containing from 1 to 3 identical or different, non-adjacent oxygen and divalent sulfur heteroatoms, with the proviso that such heterocycle can also contain from one to two carbon-carbon double bonds, and, if a 5-membered heterocycle, can also contain a nitrogen heteroatom separated from an oxygen or sulfur heteroatom by at least one ring carbon atom and linked to one of the adjacent carbon atoms by a double bond.
    Type: Grant
    Filed: October 19, 1983
    Date of Patent: September 3, 1985
    Assignee: Rhone-Poulenc Chimie de Base
    Inventor: Jean Jenck
  • Patent number: 4521614
    Abstract: Esters, e.g., alkyl adipates, are facilely prepared by carbonylation among an alcohol, carbon monoxide and a monoolefin, e.g., an alkyl pentenoate, in the presence of a catalytically effective amount of cobalt and a tertiary nitrogen base, and optionally hydrogen, said reaction being carried out in an aromatic hydrocarbon reaction medium bearing from 1 to 3 nuclear substituents, and said substituents comprising cyano or a radical of the formula R--Y-- having up to 20 carbon atoms, wherein Y is a direct valence bond, an oxygen atom, a sulfur atom, a carbonyl group or a carbonyloxy group (--CO--O--), with R being bonded to the oxygen of the group --CO--O--, and R is alkyl, aralkyl or or aryl, or a cyano substituted such R--Y-- radical, or a radical R--Y-- which includes one of the divalent bridges --O--, --CO-- or --CO--O-- along its skeletal carbon chain, with the proviso that at least one of said substituents is either cyano or a radical R--Y-- wherein Y is other than a direct valence bond.
    Type: Grant
    Filed: May 3, 1983
    Date of Patent: June 4, 1985
    Assignee: Rhone-Poulenc Chimie De Base
    Inventor: Jean Jenck
  • Patent number: 4500346
    Abstract: Novel substituted phenoxypropionates of the formula ##STR1## in which Ar represents the group ##STR2## or the group ##STR3## in which Y represents a halogen atom or a trifluoromethyl group andb is 1 or 2,R represents a hydrogen atom or a methyl group,X represents a hydrogen atom, a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group,a and m each independently is 1 or 2, andn is 0, 1 or 2,and their use as herbicides.Novel intermediates of the formulae ##STR4## in which formulae R, X, m, n and a have the meanings given above,Z.sup.1 is a halogen atom andm is a hydrogen atom or an alkali metal atom.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: February 19, 1985
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Junichi Saito, Kazuomi Yasui, Kozo Shiokawa, Atsumi Kamochi
  • Patent number: 4487957
    Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.
    Type: Grant
    Filed: April 21, 1983
    Date of Patent: December 11, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4465852
    Abstract: A process for producing carboxylic acid esters by reacting an olefin and a carboxylic acid in the presence of a crystalline metallosilicate catalyst. The catalyst has a mole ratio of silica to metal oxide of at least 12. The metal of the metal oxide is an element selected from the group consisting of the elements belonging to Groups III, IV, V, VI B, and VIII of the Periodic Table. The catalyst is preferably zeolitic, for example zeolitic aluminosilicate. The process is particularly effective when reacting relatively inactive olefins such as methylene and propylene.
    Type: Grant
    Filed: December 11, 1981
    Date of Patent: August 14, 1984
    Assignee: Idemitsu Kosan Company Limited
    Inventor: Haruhito Sato
  • Patent number: 4454343
    Abstract: Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a .gamma.-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.
    Type: Grant
    Filed: December 3, 1982
    Date of Patent: June 12, 1984
    Assignee: FMC Corporation
    Inventors: Kiyoshi Kondo, Kiyohide Matsui
  • Patent number: 4443475
    Abstract: Novel amides of acyl-carnitines having general formula ##STR1## wherein R' is acetyl, propionyl, butyryl (unsubstituted or halogen-substituted) isobutyryl, .beta.-hydroxybutyryl, acetoacetyl, pantothenyl, and linoleyl, and R" is either an unsubstituted amino radical (provided that R' is ather than acetyl) or a substituted amino radical, are therapeutically effective in treatment of functional arrythmias or arrhythmias secondary to myocardialsclerotic diseases and as psychosti-mulants.
    Type: Grant
    Filed: May 26, 1982
    Date of Patent: April 17, 1984
    Inventor: Claudio Cavazza
  • Patent number: 4442303
    Abstract: In one of its embodiments this invention provides a process for recovering C.sub.4 -C.sub.6 dicarboxylic acid components contained in a waste byproduct stream derived from a reaction system in which adipic acid is produced by nitric acid oxidation of cyclohexanone/cyclohexanol.An important aspect of the process is the esterification and extraction of the C.sub.4 -C.sub.6 dicarboxylic acids in the aqueous byproduct stream with a mixture of C.sub.1 -C.sub.3 alkanol and C.sub.6 -C.sub.20 alkanol, and the subsequent recovery of di(C.sub.6 -C.sub.20 alkyl) esters of succinic acid, glutaric acid and adipic acid.In a broader aspect this invention provides a process for recovery of water miscible organic acid components contained in an aqueous solution as C.sub.6 -C.sub.20 alkyl esters of the organic acids.
    Type: Grant
    Filed: December 9, 1980
    Date of Patent: April 10, 1984
    Assignee: El Paso Products Company
    Inventor: Samuel S. Mims
  • Patent number: 4440946
    Abstract: This invention is a process for producing a carboxylate ester which involves contacting mixtures of alcohol and aldehyde in vapor phase with a reduced silver-cadmium-zinc-zirconium catalyst composition.
    Type: Grant
    Filed: July 26, 1982
    Date of Patent: April 3, 1984
    Assignee: Celanese Corporation
    Inventors: Richard H. Summerville, deceased, James E. Summerville, Jr., administrator
  • Patent number: 4440947
    Abstract: Substituted .alpha.-halogenopropionic acids and their derivatives of the general formula ##STR1## wherein R.sup.1 to R.sup.3, Y and X have the meanings given in the description, are prepared by a process which is characterized in that substituted vinylidene chlorides of the general formula ##STR2## are reacted with chlorine or bromine chloride in the presence of compounds of the formulaR.sup.5 --SO.sub.3 R.sup.6 (III)wherein R.sup.5 and R.sup.6 have the meaning given in the description, and the products obtained are treated, if appropriate, with water or alcohol. Certain of the substituted .alpha.-halogeno-propionic acids and the substituted vinylidene chloride of the formula ##STR3## are new. The end products are useful as herbicides and intermediates for insecticides.
    Type: Grant
    Filed: March 5, 1982
    Date of Patent: April 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 4425277
    Abstract: A novel and effective catalyst system is provided for application in the preparation of alkenyl esters of carboxylic acids by transesterification reaction. The catalyst system consists of a palladium compound as the main ingredient and a cocatalyst formed of an alkali metal compound and a copper compound, at least one of which is a halide. The catalyst ingredients are adsorbed on a solid catalyst carrier, so that repeated use of the combined catalyst or a continuous operation of the reaction can easily be facilitated.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: January 10, 1984
    Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.
    Inventors: Fumiaki Kawamoto, Shozo Tanaka, Yoshihiro Honma
  • Patent number: 4414410
    Abstract: Alkyl esters, such as ethyl acetate, are prepared by contacting the corresponding next lower carbon number alkyl ester, such as methyl acetate, with carbon monoxide and hydrogen in the presence of an iodine or iodide-free catalyst composition comprising a ruthenium-containing compound, a cobalt containing compound and a quaternary phosphonium salt or base, and heating the mixture to an elevated temperature and pressure for sufficient time to produce the desired higher alkyl ester, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: November 8, 1983
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4408068
    Abstract: What is disclosed is a process for the preparation of optically active 2-chloropropionic acid esters by the decomposition of optically active 2-chlorosulfinoxypropionic acid esters in the presence of quaternary ammonium or phosphonium salts as catalysts.
    Type: Grant
    Filed: January 25, 1982
    Date of Patent: October 4, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Manfred Koch
  • Patent number: 4401827
    Abstract: Novel acyl-derivatives of the .beta.-hydroxy-.gamma.-butyrobetaine are disclosed (typically pyruvyl carnitine hydrochloride) which are useful therapeutic agents in the treatment of cardiac disorders, hyperlipidoemias and hyperlipoproteinemias.
    Type: Grant
    Filed: December 28, 1981
    Date of Patent: August 30, 1983
    Assignee: Sigma-Tau
    Inventor: Paolo de Witt
  • Patent number: 4400517
    Abstract: 1,2,4-triazol-(5)-yl-[thio] phosphates are disclosed having the formula ##STR1## wherein R.sup.1 =alkyl with from 1 to 5 carbon atoms;R.sup.2 =OR.sup.1, R.sup.1, C.sub.6 H.sub.5, NHR.sup.1, N(R.sup.1).sub.2 ;X=O, SR.sup.3 =H, alkyl with from 1 to 5 carbon atoms, C.sub.6 H.sub.5, benzyl, alkenyl with from 2 to 6 carbon atoms, alkynyl with from 2 to 6 carbon atoms; andR.sup.4 =vinyl, halovinyl, polyhalovinyl, vinyl substituted with aryl groups, alkyl groups with from 1 to 4 carbon atoms, O-alkyl groups with from 1 to 4 carbon atoms, S-alkyl groups with from 1 to 4 carbon atoms; haloalkyl, acetyl, cyclohexenyl, benzoyl ##STR2## Also disclosed are 1,2,4-triazole intermediates having the formula ##STR3## wherein: X, R.sup.3 and R.sup.4 have the same meanings as indicated above. The phosphate esters are useful in combatting infestations of pests such as orthoptera, aphides, diptera, lepidoptera, coleoptera, acari, nematodes.
    Type: Grant
    Filed: January 29, 1980
    Date of Patent: August 23, 1983
    Assignee: Montedison S.p.A.
    Inventors: Franco Gozzo, Pier M. Boschi, Angelo Longoni
  • Patent number: 4370497
    Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.
    Type: Grant
    Filed: August 7, 1980
    Date of Patent: January 25, 1983
    Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
  • Patent number: 4365083
    Abstract: A method for preparation of alkyl carboxylate compounds, and especially methylalkyl carboxylate compounds, by reaction of an olefin and a carboxylic acid compound in the presence of a mordenite catalyst.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: December 21, 1982
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4365084
    Abstract: A method for preparation of alkyl carboxylate compounds, and especially .alpha.-methylalkyl carboxylate compounds, by reaction of an olefin and a carboxylic acid compound in the presence of a particular type of zeolite catalyst. The zeolites are characterized by a silica to alumina mole ratio of at least 12 and a constraint index of 1 to 12. Zeolites ZSM-5 and ZSM-12 are particularly preferred.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: December 21, 1982
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4348535
    Abstract: There are disclosed substituted lactones of the formula ##STR1## wherein A stands for --CH--CH.sub.2 X (X being Cl, Br or OH), --CHY--CHY-- (Y being Cl or Br), or ##STR2## and R.sup.1, R.sup.2 and R.sup.3 are the same or different radicals from the group of hydrogen and C.sub.1 to C.sub.10 alkyls, at least one of the radicals R.sup.1, R.sup.2 and R.sup.3 being such an alkyl radical, and process for making the same.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: September 7, 1982
    Assignee: Dynamit Nobel AG
    Inventor: Hans-Georg Schmidt
  • Patent number: 4334083
    Abstract: A racemic or optically active alkyl 2-chloropropionate is prepared, respectively, from a racemic or optically active alkyl lactate by, in a first step, gradually bringing the alkyl lactate into contact with the thionyl chloride, in the presence of an organic base, while maintaining, in the reaction mixture, an excess of thionyl chloride, relative to the amount of alkyl lactate introduced into this mixture, at a temperature below the decomposition point of the chlorosulphinate of the alkyl lactate, which is formed as an intermediate, and then, in a second step, in heating the reaction mixture resulting from the first step at a temperature which is at least equal to the decomposition point of the chlorosulphinate of the alkyl lactate.The alkyl 2-chloropropionates can be used for the manufacture of the racemic or optically active 2-phenoxypropionic acids.
    Type: Grant
    Filed: May 21, 1980
    Date of Patent: June 8, 1982
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Bernard Buathier, Andre Bernard
  • Patent number: 4310464
    Abstract: 4-.beta., .beta.-dichlorovinyl (or dibromovinyl)-3,3-dimethylbutyrolactones are prepared from 1,1-dichloro (or dibromo)-4-methylpenta-1,3-diene by reacting with an acid of formula CH.sub.2 R.CO.sub.2 H in presence of a salt of a metal in one of its higher valency states, especially manganese (III), cerium (IV), or vanadium (V). Higher yields are obtained in the presence of the anhydride of the acid and of the sodium or potassium salt of the acid. Treatment of the lactones with an inorganic acid halide opens the lactone ring with formation of the corresponding 4-haloacid halide, which with alcohols affords the corresponding 4-haloacid ester, cyclised by bases to a 3-.beta.,.beta.-dichloro (or dibromo)vinyl-2,2-dimethylcyclopropanecarboxylic ester, intermediate for insecticides such as the m-phenoxybenzyl ester.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: January 12, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Winston Costain, Bernard W. H. Terry, Nazim Punja, Peter J. V. Cleare
  • Patent number: 4305876
    Abstract: A process for asymmetrically hydrogenating through the use of microorganisms a double bond connected to tertiary carbon atom in an olefinic aliphatic compound to produce a tertiary, optically active aliphatic compound useful as an intermediate for optically active Vitamins E and K.
    Type: Grant
    Filed: November 24, 1978
    Date of Patent: December 15, 1981
    Assignee: Hoffmann-La Roche, Inc.
    Inventors: Richard Barner, Walter Boguth, Hans G. W. Leuenberger, Max Schmid, Reinhard Zell
  • Patent number: 4303792
    Abstract: N-substituted haloacyloxyacetamide compounds having the following formula: ##STR1## in which R.sub.1 is selected from the group consisting of chlorine and bromomethyl;R.sub.2 is selected from the group consisting of hydrogen, chlorine and bromine;R.sub.3 is selected from the group consisting of hydrogen, 1-4 carbon alkyl, 2-10 carbon alkenyl, and methylene malononitrile;R.sub.4 is selected from the group consisting of 1-10 carbon alkyl, 2-10 carbon alkenyl, 2-10 carbon alkynyl, and substituted phenyl wherein said substituents are chloro or 1-6 chloro alkyl; orR.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are selected from the group consisting of 4-10 carbon alkylene ring and 4-10 carbon alkyl substituted oxazolidine ring; provided that when R.sub.1 and R.sub.2 are chlorine, then R.sub.3 and R.sub.4 are other than allyl. The compounds are useful as herbicidal antidotes for protection of crops from thiocarbamate herbicidal injury.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: December 1, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Hsaio-Ling Lam
  • Patent number: 4301084
    Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: November 17, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Laas, Axel Nissen, Bernd Meissner
  • Patent number: 4289711
    Abstract: A novel process is described for the preparation of compounds of formula ##STR1## wherein R.sup.2 and R.sup.3 are each chloro or bromo; X is carboxyl, nitrile, optionally substituted carbonamide, carbonyl halide or an ester group. Those compounds wherein X is an appropriate ester group --COOB where B is an aryl group such as m-phenoxybenzyl are known insecticides; compounds where X is other than --COOB may be suitably converted thereto.The novel process consists of a series of steps from the corresponding acetyl compound of formula ##STR2## which comprises halogenation, reduction, esterification and finally elimination reactions.
    Type: Grant
    Filed: September 3, 1976
    Date of Patent: September 15, 1981
    Assignee: Burroughs Wellcome Co.
    Inventor: Grahame R. Lee
  • Patent number: 4283536
    Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of among other alkaloids vincamine and other similar compounds possessing interesting psychopharmacologic properties.A tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide a 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (III). Then compound (III) is reduced to give a 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido-(3,4-b)-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into a chloroindolenine derivative (V) which is immediately treated with a metal dialkylmalonate such as thallium t-butyl methyl malonate to give a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-(4,5-b)-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into a alkyl 3-benzyl-1,2,3,4,5,6-hexahydro-(4,5-b) indole-5-carboxylate (VII).
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: August 11, 1981
    Assignee: University of Vermont
    Inventor: Martin E. Kuehne
  • Patent number: 4281176
    Abstract: Carboxylic acids are esterified with ethylene gas, to effect the formation of ethyl esters, by acid catalysis in the presence of at least one dissociating, inert and stable solvent which increases the acidity of the reaction medium.
    Type: Grant
    Filed: January 16, 1979
    Date of Patent: July 28, 1981
    Assignee: Rhone-Poulenc Industries
    Inventors: Max Gruffaz, Odile Micaelli
  • Patent number: 4270015
    Abstract: This invention concerns a two-step process for the preparation of ethylene from mixture of carbon monoxide and hydrogen (commonly known as synthesis gas) by reaction of said carbon monoxide/hydrogen mixtures with a carboxylic acid in the presence of one or more ruthenium catalyst complexes to form an ethyl ester of said carboxylic acid coreactant, followed by pyrolysis of said ethyl ester intermediate to ethylene.
    Type: Grant
    Filed: July 14, 1980
    Date of Patent: May 26, 1981
    Assignee: Texaco Inc.
    Inventor: John F. Knifton
  • Patent number: 4267330
    Abstract: This invention relates to the preparation of vincadifformine and related derivatives which are useful as starting material for the synthesis of vincamine and other related compounds possessing interesting psychopharmacologic properties.A N-benzyl-tetrahydro-.gamma.-carboline compound (III) is halogenated with t-butyl hypochlorite to obtain a haloindolenine compound which is directly treated with a metal dialkyl malonate such as thallium dialkyl malonate to provide a dialkyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5,5-dicarboxylate compound, said latter compound being hydrogenated to provide a dialkyl 1,2,3,4,5,6 hexahydroazepino (4,5-b) indole-5,5-dicarboxylate, said latter compound being condensed with a functionalized aldehyde, typically a haloaldehyde, to provide vincadifformine or a related derivative by passing through an intermediate compound being a salt of a dialkyl 3,3-(alkenyl)-1,2,3,4,5,6-hexahydroazepino(4,5-b) indolinium-(5,5)-dicarboxylate.
    Type: Grant
    Filed: August 24, 1978
    Date of Patent: May 12, 1981
    Assignee: Omnium Chimique Societe Anonyme
    Inventor: Martin E. Kuehne
  • Patent number: 4263157
    Abstract: Compounds of the general formula I ##STR1## in which R.sub.1 is chlorine or --CH.sub.2 --CCl.sub.3, andR.sub.2 is --N(R.sub.3)R.sub.4, --OH.N(R.sub.3)(R.sub.4)R.sub.5 or --OR.sub.6,R.sub.3 is C.sub.1 -C.sub.24 alkyl which can be interrupted once or several times by oxygen,R.sub.4 and R.sub.5 independently of one another are hydrogen or C.sub.1 -C.sub.24 alkyl, with R.sub.3 and R.sub.4 together having at least 8 C atoms,R.sub.6 is C.sub.8 -C.sub.20 alkyl, phenyl or C.sub.7 -C.sub.15 alkylphenyl, a group of the formula --(A)R.sub.7 or --CH.sub.2 CH.sub.2 --N(R.sub.10)--CH.sub.2 CH.sub.2 --O--C(O)--CH(R.sub.1)CH.sub.2 CCl.sub.3, whereinR.sub.7 is a radical of the formula --(R.sub.8)C(R.sub.9)--O--C(O)--CH(R.sub.1)--CH.sub.2 --CCl.sub.3, whereinR.sub.8 and R.sub.9 independently of one another are hydrogen, methyl or ethyl, and R.sub.1 has the meaning defined above,A is a C.sub.1 -C.sub.7 alkylene group which is unsubstituted or substituted by one or two radicals R.sub.
    Type: Grant
    Filed: April 18, 1979
    Date of Patent: April 21, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Eginhard Steiner, Andreas Schmidt
  • Patent number: 4228109
    Abstract: This invention relates to aliphatic phosphorous containing compounds which are useful as herbicides. Additionally, they demonstrate tolerance towards desired, crops, e.g. wheat and rice.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: October 14, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4225521
    Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: September 30, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4221921
    Abstract: A process for producing monochloroacetic acid from hydroxyacetic acid which comprises feeding hydroxyacetic acid and aqueous hydrogen chloride to a reaction zone and contacting the hydroxyacetic acid with the aqueous hydrogen chloride in the presence of hydrogen iodide catalyst at a temperature between 100.degree. and 250.degree. C. and a pressure sufficient to maintain the aqueous hydrogen chloride in liquid phase. Preferably the reaction is carried out at a temperature between about 130.degree. and 200.degree. C.
    Type: Grant
    Filed: May 10, 1978
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4217312
    Abstract: This invention relates to phosphorus containing compounds which are useful as herbicides.Additionally, they demonstrate tolerance towards desired crops, e.g., cotton, soybeans and sugarbeets.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: August 12, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard F. Sauers
  • Patent number: 4196300
    Abstract: Glycidates and thioglycidates substituted in the .alpha.-position with a long chain alkyl of from 11 to 16 carbons having hypoglycemic activity.
    Type: Grant
    Filed: August 18, 1978
    Date of Patent: April 1, 1980
    Assignee: McNeilabs, Inc.
    Inventors: Richard J. Mohrbacher, Winston Ho, Gene Tutwiler
  • Patent number: 4159991
    Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: July 3, 1979
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
  • Patent number: 4156090
    Abstract: 15,15'-Didehydro-astaxanthin and ester derivatives thereof useful as coloring agents and intermediates for astaxanthin and a method for preparing astaxanthin from keto .alpha.-isophorone and intermediates therein.
    Type: Grant
    Filed: November 12, 1976
    Date of Patent: May 22, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Frank Kienzle
  • Patent number: 4123443
    Abstract: New economically valuable and convenient methods for preparing bromoacetic acid and its esters from chloroacetic acid are disclosed.
    Type: Grant
    Filed: March 6, 1978
    Date of Patent: October 31, 1978
    Assignee: Katayama Chemical Works Co., Ltd.
    Inventors: Umekawa Osamu, Takemori Koji, Katayama Sakae
  • Patent number: 4113968
    Abstract: When 1-halogeno-3-alkene-2-ol is reacted with an ortho-carboxylic ester and/or a ketene acetal, a .gamma.-halogeno-.delta.-unsaturated-carboxylic ester is obtained as a main reaction product. When this intermediate is treated with a basic substance, a substituted cyclopropane-carboxylic ester is formed. This ester can be used as an insecticide or an agricultural chemical as it is or after the alcohol residue of the ester has been converted to other alcohol residue.
    Type: Grant
    Filed: September 26, 1975
    Date of Patent: September 12, 1978
    Assignee: Kuraray Co., Ltd.
    Inventors: Fumio Mori, Yoshiaki Omura, Takashi Nishida, Kazuo Itoi
  • Patent number: 4112228
    Abstract: 7-(D-.alpha.-Hydroxy-2-arylacetamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triaz olo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids and derivatives containing blocking groups on the .alpha.-hydroxy group and their nontoxic, pharmaceutically acceptable salts are valuable as antibacterial agents and are particularly valuable as therapeutic agents in poultry and in animals, including man, in the treatment of infectious diseases caused by many Gram-positive and Gram-negative bacteria. A preferred compound is 7-(D-mandelamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin -3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acid.
    Type: Grant
    Filed: March 16, 1977
    Date of Patent: September 5, 1978
    Assignee: Bristol-Myers Company
    Inventors: Takayuki Naito, Jun Okumura, Hajime Kamachi
  • Patent number: 4111683
    Abstract: Compounds of the formula ##STR1## wherein R is aliphatic hydrocarbyl, alicyclic hydrocarbyl or aryl suitably substituted, if desired, or a heterocyclic group, R.sup.1 is hydrogen or alkyl, R.sup.2 is alkyl or alkoxy, R.sup.3 is ##STR2## wherein a is 0 or 1, R.sup.4 is hydrogen or CW'.sub.3, the W' being hydrogen or halogen, Z is halogen and X is halogen, hydroxy, alkoxy, acetoxy, carbethoxyalkoxy, phenoxy, alkylthio, carbethoxyalkylthio, phenylthio, phosphono, dithiophosphonoxy, phosphoramido, isocyanato, isothiocyanato, alkyl- and dialkylthiocarbamoylthio, alkyl- and dialkylcarbamoyloxy, alkylsulfonyl, etc., have herbicidal activity.
    Type: Grant
    Filed: November 12, 1976
    Date of Patent: September 5, 1978
    Assignee: Chevron Research Company
    Inventor: Malcolm Scott Singer