Halogen Patents (Class 562/472)
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Patent number: 4786732Abstract: A method for the effective chromatographic resolution and analysis of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids which comprises dissolving a 2-(4-aryloxyphenoxy)propionic acid in a suitable solvent, injecting the solution into a liquid chromatographic system and eluting the components from the column using an eluent contain R-(-)- or S-(+)-2-pyrrolidinemethanol and an alkanoic acid in a suitable solvent.Type: GrantFiled: August 5, 1987Date of Patent: November 22, 1988Assignee: The Dow Chemical CompanyInventor: John W. Russell
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Patent number: 4767784Abstract: The invention relates to novel crystalline salts of aryloxypropanolamines with diphenylacetic acid, a process for their preparation and the use of these salts for the preparation of chemically pure aryloxy-propanolamines or pharmaceutically acceptable salts thereof.Type: GrantFiled: November 28, 1986Date of Patent: August 30, 1988Inventors: Gerhard Zolss, Gerhard Pfarrhofer
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Patent number: 4766220Abstract: The invention relates to the preparation of optically active aryloxyalkanoic acid derivatives of the formula ##STR1## in which Ar represents an optionally substituted phenyl, naphthyl, phenoxy or pyridyloxy radical, R represents a C.sub.1 -C.sub.4 -alkyl radical and A represents a --COOR.sub.1, ##STR2## or --CO--Z radical, Z being halogen. It consists in reacting an aqueous or aqueous-organic solution of an optically active alkali metal salt of a 2-halogeno-alkanoic acid with an aqueous solution of an alkali metal salt of the phenol of the formula Ar-OH at an elevated temperature under a pressure less than the vapor pressure of water at the chosen temperature.It permits the preparation of aryloxyalkanoic acid derivatives with a very high content of the isomer having the D configuration, which can be used as herbicides.Type: GrantFiled: July 30, 1985Date of Patent: August 23, 1988Assignee: Rhone-Poulenc AgrochimieInventor: Georges Gras
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Patent number: 4757155Abstract: A process for the preparation of optically active 2-[4-(2',4'-dihalophenoxy)phenoxy]propionic acids of at least 75 percent enantiomeric excess of the desired optical isomer which comprises contacting a 2-chloropropionic acid or a lower alkyl ester or an alkali metal salt thereof, having an optical purity of greater than 90 percent of the opposite configuration, with from 2 to 10 molar equivalents of a 4-(2',4'-dihalphenoxy)phenol in an aqueous base.Type: GrantFiled: December 22, 1986Date of Patent: July 12, 1988Assignee: The Dow Chemical CompanyInventor: Jimmy J. Tai
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Patent number: 4727181Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.Type: GrantFiled: April 21, 1986Date of Patent: February 23, 1988Assignee: The Dow Chemical CompanyInventor: William J. Kruper, Jr.
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Patent number: 4699920Abstract: The invention relates to 9-halo-.DELTA..sup.2 -prostane derivatives of general Formula I ##STR1## wherein Hal is a fluorine or chlorine atom in the .alpha.- or .beta.-position,R.sub.1 is the residue OR.sub.2 with R.sub.2 meaning a hydrogen atom, alkyl, cycloalkyl, aryl or a heterocyclic residue; or the residue NHR.sub.3 wherein R.sub.3 means an acid residue or the residue R.sub.2 andA is a --CH.sub.2 --CH.sub.2 -- or cis-CH.dbd.CH--group,B is a --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH-- or --C.tbd.C--group,W is a free or functionally modified hydroxymethylene or ##STR2## wherein the respective OH-groups can be in the .alpha.- or .beta.-position,D and E jointly mean a direct bond orD is a straight- or branched-chain alkylene group of 1-10 carbon atoms, which can optionally be substituted by fluorine atoms,E is an oxygen or sulfur atom, a direct bond, a --C.tbd.C--bond or a --CR.sub.6 .dbd.CR.sub.7 --group wherein R.sub.6 is a hydrogen atom or an alkyl group and R.sub.Type: GrantFiled: September 17, 1985Date of Patent: October 13, 1987Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge
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Patent number: 4691020Abstract: Optically active carboxylic acids ##STR1## where R.sup.1 is an organic radical which is linked to the asymmetric C' atom via a carbon atom and R.sup.2 is one of the radicals R.sup.1 (but not the same radical), halogen or an organic radical which is bonded to the asymmetric C' atom via an oxygen atom, are prepared by reacting a ketene II ##STR2## with an alcohol in a homogeneous liquid phase in the presence of a tertiary amine III and then converting the resulting ester into the acid, using an optically active alcohol IV.Type: GrantFiled: July 23, 1984Date of Patent: September 1, 1987Assignee: BASF AktiengesellschaftInventors: Christoph Ruechardt, Joachim Jaehme, Ulrich Salz
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Patent number: 4622415Abstract: There is disclosed an R enantiomer of phenoxypropionic acid compound of the formula ##STR1## in which X represents hydrogen or halogen, and R represents hydroxyl, alkoxy, halogen or the radical of the formula ##STR2## wherein R.sup.1 and R.sup.2 independently of one another represent hydrogen or methyl, n represents 0, 1 or 2 and Y represents trimethylsilyl, or optionally substituted azolyl bonded via nitrogen, or represents alkoxy, alkoxycarbonyl or the radical of the formula ##STR3## wherein Q represents oxygen, sulphur, SO or SO.sub.2 and R.sup.3 and R.sup.4 independently of one another represent hydrogen, halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, nitro, cyano or alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy group; compositions containing herbicidally effective amounts of such R enantiomers and the use of such R enantiomers as herbicides.Type: GrantFiled: July 31, 1985Date of Patent: November 11, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Bernd Gallenkamp, Uwe Priesnitz, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt
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Patent number: 4601797Abstract: Hydroxyibuprofen is produced in good yield by reduction of p-isobutylacetophenone at the cathode in the presence of carbon dioxide. Hydroxyibuprofen is readily hydrogenolyzed to ibuprofen. Electrochemical carboxylation of other selected aryl methyl ketones is also effected.Type: GrantFiled: March 1, 1985Date of Patent: July 22, 1986Assignee: Monsanto CompanyInventor: John H. Wagenknecht
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Patent number: 4589907Abstract: Compounds having the formula ##STR1## in which Z is ##STR2## wherein X is hydrogen or halogen and Y is --CH or N; R is alkyl, phenyl, trihalomethylphenyl, cyanomethyl, carboalkoxymethyl, ##STR3## alkenyl; and R.sub.1 is hydrogen, lower alkyl, halo-(lower alkyl), or Z; and intermediate alkyl onium salts of the type ##STR4## in which R.sub.3 is C.sub.1 -C.sub.8 alkyl, G is nitrogen or phosphorus and Z' is ##STR5## wherein X is hydrogen or halogen and Y is --CH or N; are herbicides.Type: GrantFiled: September 17, 1985Date of Patent: May 20, 1986Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4568497Abstract: Preparation of monoethers of dihydroxybenzenes from an alkenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.Type: GrantFiled: May 29, 1984Date of Patent: February 4, 1986Assignee: The Dow Chemical CompanyInventors: Abel Mendoza, Eric W. Otterbacher
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4552977Abstract: Process for the preparation of (phenoxy- or benzyl-)-phenoxypropionic acids and the alkali metal salts thereof by adding a double molar amount of an aqueous alkali hydroxide to a boiling mixture of a (benzyl- or phenoxy-)-phenol and 2-chloropropionic acid (ester), with simultaneous azeotropic distillation of the water introduced or formed in the reaction.Type: GrantFiled: September 24, 1982Date of Patent: November 12, 1985Assignee: Hoechst AktiengesellschaftInventors: Manfred Koch, Peter Herbrechtsmeier
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Patent number: 4536483Abstract: Iron-antimony metallic oxide catalysts which have become deactivated after being used for the production of aldehydes, acids, nitriles, or dienes through oxidation, ammoxidation, or oxidative dehydrogenation of organic compounds in fluidized-bed reactors are regenerated by adding to the catalyst a solid molybdenum component which is volatile or capable of forming a volatile compound under reaction conditions. The metallic oxide catalysts contain as essential components (I) Fe, (II) Sb, (III) at least one element selected from the group consisting of V, MO, and W, and (IV) Te.Type: GrantFiled: October 26, 1983Date of Patent: August 20, 1985Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yutaka Sasaki, Yutaka Kiyomiya, Toshio Nakamura, Yoshimi Nakamura, Masanori Yamaguchi
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Patent number: 4531969Abstract: Optically active enantiomers of the formula I ##STR1## where R is a group of the formulae ##STR2## R.sub.1 and R.sub.2, among others, are halogen or CF.sub.3 and Z is a carboxyl, carboxylate, carboxylic acid ester, thioester, carbonamide, carboxylic acid anilide, carbohydrazide or thioamide group, are interesting herbicides the effect of which is considerably superior to that of the optically inactive racemates.Type: GrantFiled: December 20, 1978Date of Patent: July 30, 1985Assignee: Hoechst AktiengesellschaftInventors: Hans J. Nestler, Gerhard Horlein, Reinhard Handte, Hermann Bieringer, Friedhelm Schwerdtle, Peter Langeluddeke
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Patent number: 4515985Abstract: A process for the preparation of 2,4-dichloro- or 2-methyl-4-chlorophenoxyacetic acid or .alpha.-2,4-dichloro- or .alpha.-2-methyl-4-chlorophenoxypropionic acid by reacting phenoxyacetic or 2-methylphenoxyacetic acid or .alpha.-phenoxypropionic or .alpha.-2-methylphenoxypropionic acid with chlorine in water, wherein phenoxyacetic acid or phenoxypropionic acid is precipitated from an aqueous solution thereof, chlorine gas is passed into the resulting suspension of phenoxyacetic or 2-methylphenoxyacetic acid or .alpha.-phenoxypropionic or .alpha.-2-methylphenoxypropionic acid in water at from 30.degree. to 70.degree. C. at a rate not exceeding the rate at which it is consumed in the suspension, until from 100 to 110% of the theoretically required amount of chlorine gas has been taken up by the suspension, and the 2,4-dichloro- or 2-methyl-4-chloro-phenoxyacetic acid or .alpha.-2,4-dichloro- or .alpha.-2-methyl-4-chloro-phenoxypropionic acid is isolated from the suspension.Type: GrantFiled: December 16, 1981Date of Patent: May 7, 1985Assignee: BASF AktiengesellschaftInventors: Gerd Husslein, Gerhard Hamprecht, Karl-Heinz Koenig, Walter Boehm, Manfred Gaeng
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Patent number: 4492799Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.Type: GrantFiled: July 2, 1979Date of Patent: January 8, 1985Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4479900Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is lower alkyl or benzyl. R.sup.2 is lower alkoxy, benzyloxy, or the group ##STR2## where R.sup.3 is lower alkoxy; and Ar is phenyl optionally substituted with 1 to 3 substituents independently selected from halogen, trihalomethyl, nitro or lower alkyl, show plant growth regulating activity.Type: GrantFiled: April 29, 1983Date of Patent: October 30, 1984Assignee: Chevron Research CompanyInventor: Tatao Luo
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Patent number: 4468247Abstract: Salts, esters, amides, hydrazides and hydroxyamides of 4-methyl-4-[3'-(4"-trifluoromethylphenoxy)-phenoxy]crotonic acid are herbicidal against broad leaf plants.Type: GrantFiled: June 22, 1982Date of Patent: August 28, 1984Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4459306Abstract: This invention relates to novel tricyclic ethers, pharmaceutically acceptable addition salts and optical isomers therefrom. The compounds described herein are useful as psychotropic agents in the treatment of depression and anxiety. Also included herein are methods of preparing said compounds, pharmaceutical compositions including them and methods of treating human or animal beings by administering these pharmaceutical compositions.Type: GrantFiled: April 6, 1981Date of Patent: July 10, 1984Assignee: Science Union et CieInventors: Charles Malen, Jean-Claude Poignant
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Patent number: 4456768Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.Type: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4454344Abstract: A method for the resolution of racemic 2-(p-difluoromethoxyphenyl)-3-methylbutyric acid into its optically active components. The method utilizes salts prepared by reacting the racemic acid with optically active amines and recovers the dextrorotatory isomer. The present invention also relates to insecticidal pyrethroids prepared from (+)-2-(p-difluoromethoxyphenyl)-3-methylbutyric acid.Type: GrantFiled: August 23, 1982Date of Patent: June 12, 1984Assignee: American Cyanamid CompanyInventor: Venkataraman Kameswaran
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Patent number: 4444788Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position,R.sub.1 is OR.sub.2, or NHR.sub.3 wherein R.sub.3 is H or the acyl group ofa C.sub.1-15 hydrocarbon carboxylic or sulfonic acid;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --,trans--CH.dbd.CH--, or --C.tbd.C--, ##STR2## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl dimethyl, tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;D and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.Type: GrantFiled: June 10, 1982Date of Patent: April 24, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 4429167Abstract: This invention relates to 3-alkoxy-4-substituted-phenoxy-2,3-unsaturated acid esters and derivatives thereof and the use of said acid esters and derivatives for the control of weeds.Type: GrantFiled: January 22, 1982Date of Patent: January 31, 1984Assignee: Zoecon CorporationInventor: Shy-Fuh Lee
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9-Deoxy-9-methylene derivatives of (dl)-16-phenoxy and 16-phenoxy substituted prostatriene compounds
Patent number: 4418206Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.Type: GrantFiled: March 22, 1982Date of Patent: November 29, 1983Assignee: Syntex (U.S.A.) Inc.Inventor: Douglas L. Wren -
Patent number: 4416687Abstract: 3,5-Bis (trifluoromethyl)phenoxy carboxylic acids and derivatives thereof have been found to reduce herbicidal injury of certain food crops, especially grain sorghum, due to the application thereto of herbicides that kill or control weeds that impede the yield of the crops.Type: GrantFiled: February 1, 1982Date of Patent: November 22, 1983Assignee: Monsanto CompanyInventors: John J. D'Amico, Tann R. Schafer
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Patent number: 4380661Abstract: 2-[p-(p-substituted phenoxy)phenoxy]propionyl oximes, processes for their preparation, herbicidal compositions containing these oximes and methods of use of the herbicidal compositions are disclosed.Type: GrantFiled: February 23, 1981Date of Patent: April 19, 1983Assignee: Hoffmann-La Roche Inc.Inventor: Milos Suchy
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Patent number: 4365991Abstract: Propionic acid oximes of the general formula ##STR1## wherein R.sub.1 is hydrogen, alkyl of from 1 to 6 carbon atoms or cycloalkyl of from 3 to 6 carbon atoms, R.sub.2 is hydrogen, alkyl of from 1 to 6 carbon atoms, alkenyl of from 2 to 6 carbon atoms or alkynyl of from 2 to 6 carbon atoms, or R.sub.1 and R.sub.2 together with the carbon atom to which they are attached form a cyclopentane or cyclohexane ring which can be mono-, di- or trisubstituted with alkyl of from 1 to 3 carbon atoms, R.sub.3 is hydrogen, halogen or nitro with the proviso that R.sub.1 and R.sub.2 are not simultaneously hydrogen, processes for their manufacture, herbicidal compositions containing these compounds as the active ingredient and methods of use of the herbicidal compositions are disclosed.Type: GrantFiled: March 6, 1981Date of Patent: December 28, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Wijitha de Silva
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Patent number: 4360375Abstract: A herbicidal composition which comprises a phenoxyphenoxy unsaturated derivative having the formula: ##STR1## wherein X represents a halogen atom or CF.sub.3 ; Y represents a hydrogen atom or a halogen atom; and Z represents --COOR, --COR", --COOH, --CH.sub.2 OH, or --CH.sub.2 OR"'.Type: GrantFiled: December 23, 1980Date of Patent: November 23, 1982Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
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Patent number: 4354034Abstract: This invention relates to dihalophenoxypropionic acids and their derivatives useful for desiccating cotton plants, to a process for preparing these compounds, to cotton desiccating compositions containing them and to a method of desiccating cotton using them.Type: GrantFiled: June 15, 1979Date of Patent: October 12, 1982Assignee: Imperial Chemical Industries LimitedInventors: John E. Barton, David J. Collins, Donald W. Headford
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Patent number: 4348534Abstract: 2-Aryloxy-2-halopropionic acid compounds are prepared by reacting 2-aryloxypropionic acid compounds with N-halocarboxylic acid imides in the presence of aliphatic halohydrocarbons as solvents, and of from 0.0001 to 0.001 mole of halogen per mole of N-halocarboxylic acid imide, from 0.005 to 0.05 per cent by weight of water, based on N-halocarboxylic acid imide, and from 0.0005 to 0.005 mole of azo-bis-isobutyronitrile and/or dibenzoyl peroxide, per mole of N-halocarboxylic acid imide.The end products obtainable by the process of the invention are valuable starting materials for the preparation of drugs, crop protection agents and dyes.Type: GrantFiled: June 17, 1981Date of Patent: September 7, 1982Assignee: BASF AktiengesellschaftInventors: Gerd Husslein, Gerhard Hamprecht
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Patent number: 4348399Abstract: This disclosure describes novel 4-(monoalkylamino)phenyl alkane, alkene and alkyne carbinols, aldehydes, carboxylic acids and derivatives useful as hypolipidemic and antiatherosclerotic agents.Type: GrantFiled: February 2, 1978Date of Patent: September 7, 1982Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd
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Patent number: 4347379Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.Type: GrantFiled: March 10, 1980Date of Patent: August 31, 1982Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4345097Abstract: The process for the chlorination of aromatic compounds of the formula: ##STR1## wherein R is a member selected from the group consisting of hydrogen, carboxymethyl, and carboxyethyl and R.sub.x is a member selected from the group consisting of hydrogen, 2-methyl, 2,5-dichloro, and 2-chloro, with the proviso that when R is hydrogen, R.sub.x is 2,5-dichloro, consisting of reacting said aromatic compound with sulfuryl chloride in the presence of elemental sulfur or certain sulfur compounds as a catalyst, optionally together with the presence of a Friedel-Crafts acid catalyst and/or an inert organic solvent at temperatures of from 30.degree. C. to 150.degree. C., and recovering a para chlorinated compound.Type: GrantFiled: January 21, 1980Date of Patent: August 17, 1982Assignee: Vertac Chemical CorporationInventors: Kenneth J. Howard, Albert E. Sidwell
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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Patent number: 4339587Abstract: Substituted 2-(trifluoroethoxy)benzamide, benzoic acid and benzoate compounds which are intermediates in the preparation of pharmaceutically active agents.Type: GrantFiled: June 8, 1981Date of Patent: July 13, 1982Assignee: Riker Laboratories, Inc.Inventor: Elden H. Banitt
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Patent number: 4336382Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: August 25, 1980Date of Patent: June 22, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4332960Abstract: Compounds of the formula ##STR1## where R.sub.1 is H or Hal and R.sub.2 is a variety of functional groups among which is hydroxy, alkoxy and (substituted) amino, are valuable grass herbicides.Type: GrantFiled: July 8, 1975Date of Patent: June 1, 1982Assignee: Hoechst AktiengesellschaftInventors: Jurgen Trosken, Gerhard Horlein, Ernst-Friedrich Schulze, Peter Langeluddeke
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Patent number: 4332961Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.Type: GrantFiled: April 15, 1977Date of Patent: June 1, 1982Assignee: Ishihara Sangyo Kaisha, Ltd.Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
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Patent number: 4326882Abstract: This invention provides as new compositions of matter 2,4,5-trichlorophenoxy acetic acid (2,4,5-T) and (2-2,4,5-trichlorophenoxy) propionic acid (Silvex) including the hydrolyzable salts, aliphatic esters and amides of these acids, which compositions are free of chlorinated dibenzo-p-dioxins.Type: GrantFiled: April 26, 1979Date of Patent: April 27, 1982Assignee: PPG Industries, Inc.Inventors: Sidney B. Richter, William S. Grove
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Patent number: 4310689Abstract: A process is provided for making D-2-phenoxy propionic acid by condensing in water an alkali metal salt of 2-chloropropionic acid which is dextro-rotatory in water with an alkali metal phenoxide of a halogen or methyl substituted phenol. The overall amount of water in the condensation mixture is not more than about 8 moles water per mole of said alkali metal salt of 2-chloropropionic acid in order to selectively produce the dextro-rotatory optical isomer.Type: GrantFiled: September 19, 1979Date of Patent: January 12, 1982Assignee: Akzo N.V.Inventors: Willem Eveleens, Johannes Spaans, Hendrik G. Wissink
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Patent number: 4309547Abstract: Process for the preparation of (phenoxy- or benzyl-)-phenoxypropionic acids by simultaneous addition of 2-chloropropionic acid (ester) and the double molar amount of an aqueous alkali hydroxide to a solution of a phenoxyphenol or benzylphenol in a solvent forming an azeotropic mixture with water, while continuously distilling off the water formed or introduced.Type: GrantFiled: May 30, 1980Date of Patent: January 5, 1982Assignee: Hoechst AktiengesellschaftInventors: Manfred Koch, Hans J. Nestler
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Patent number: 4304936Abstract: 3-Phenoxy-.alpha.-phenoxy-alkancarboxylic acid derivatives of the formula ##STR1## are disclosed as possessing a surprising selective herbicidal activity. In the formula, Hal is a halogen atom, m is an integer 1, 2 or 3, Y is a hydrogen or halogen atom or the cyano group, Z is a halogen atom or the cyano group, R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, and R is an acid function. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.Type: GrantFiled: October 11, 1979Date of Patent: December 8, 1981Assignee: Ciba-Geigy CorporationInventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
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Patent number: 4303796Abstract: Prostaglandin-type compounds with a phenoxy or substituted-phenoxy substituent at the C-16 position are disclosed, with processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.Type: GrantFiled: December 19, 1973Date of Patent: December 1, 1981Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4301295Abstract: Novel 4-phenoxy-phenoxy-alkane-carboxylic acid derivatives of the formula I ##STR1## in which R.sub.1 stands for hydrogen, methylthio, cyclopentyl, cyclohexyl, phenyl, methylcyclohexyl, ethylcyclohexyl, or R.sub.1 and R.sub.3 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge or--unless at least one of the substituents R.sub.2 to R.sub.8 stands for hydrogen, or if R.sub.9 stands for a radical having at least 2 carbon atoms--for chlorine,R.sub.2 and R.sub.3, independent of one another, each stands for hydrogen, chlorine or alkyl of 1 to 4 carbon atoms,R.sub.4 stands for hydrogen, chlorine, alkyl of 1 to 4 carbon atoms, cyclopentyl, cyclohexyl, methylcyclohexyl or R.sub.3 and R.sub.4 together stand for a --CH.dbd.CH--CH.dbd.CH-- bridge,R.sub.5, R.sub.6 and R.sub.7, independent of one another, each stands for hydrogen or alkyl of 1 to 4 carbon atoms,R.sub.8 stands for hydrogen, alkyl of 1 to 4 carbon atoms or allyl,R.sub.Type: GrantFiled: August 20, 1980Date of Patent: November 17, 1981Assignee: Hoechst AktiengesellschaftInventors: Helmut Nahm, Ernold Granzer
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Patent number: 4293707Abstract: Trichlorophenoxy alkanoic acid including hydrolyzable salts, aliphatic esters and amides thereof said compounds being free of chlorinated dibenzo-p-dioxins are prepared by liquid phase alkaline condensation of 3-chlorophenol or 3,4-dichlorophenol with an alpha halo alkanoic acid, ester or amide followed by liquid phase chlorination of the condensation product.Type: GrantFiled: June 4, 1979Date of Patent: October 6, 1981Assignee: PPG Industries, Inc.Inventors: Sidney B. Richter, William S. Grove
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Patent number: 4278678Abstract: Novel substituted oxy-cyclohexylacetic acid derivatives as antihyperlipidemic agents are given. The compounds have the formula ##STR1## wherein n is 1 or 2; m is 0, 1 or 2; R.sub.1 represents a halogen atom, trifluoromethyl, a lower alkyl, a lower alkoxy, a lower alkylcarbonyl, dimethylphenylmethyl, cyclohexyl, phenyl, halogenophenyl, phenoxy or halogenophenoxy group, and two of R.sub.1 groups can be bonded to form an orthocondensed saturated alkylene ring; Hal represents a halogen atom; and R.sub.2 represents a hydrogen atom or a lower alkyl group.Type: GrantFiled: November 16, 1979Date of Patent: July 14, 1981Assignee: Kaken Chemical Co., Ltd.Inventors: Yasuhiko Hamazaki, Kenji Seri, Nobuo Ishiyama, Toshiyuki Yamamoto, Masao Sakasai, Reiko Sato
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Patent number: 4277612Abstract: The present invention particularly relates to novel .omega.-aryl-9-deoxy-9-methylene-5,6-didehydro-PFG.sub.1 compounds and methods for their preparation in pharmacological use.Type: GrantFiled: January 28, 1980Date of Patent: July 7, 1981Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4270948Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.Type: GrantFiled: October 17, 1979Date of Patent: June 2, 1981Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
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Patent number: 4269983Abstract: The disclosed compounds, such as 3-[5-[1-(2-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl- 2-imidazolidinone, are useful for preemergence and postemergence control of weeds, such as jimsonweed.Type: GrantFiled: June 18, 1979Date of Patent: May 26, 1981Assignee: PPG Industries, Inc.Inventor: Jerome M. Lavanish