Halogen Patents (Class 562/472)
  • Patent number: 4786732
    Abstract: 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: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4767784
    Abstract: 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: Grant
    Filed: November 28, 1986
    Date of Patent: August 30, 1988
    Inventors: Gerhard Zolss, Gerhard Pfarrhofer
  • Patent number: 4766220
    Abstract: 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: Grant
    Filed: July 30, 1985
    Date of Patent: August 23, 1988
    Assignee: Rhone-Poulenc Agrochimie
    Inventor: Georges Gras
  • Patent number: 4757155
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: July 12, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jimmy J. Tai
  • Patent number: 4727181
    Abstract: Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: February 23, 1988
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4699920
    Abstract: 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: Grant
    Filed: September 17, 1985
    Date of Patent: October 13, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduchel, Helmut Vorbruggen, Walter Elger, Olaf Loge
  • Patent number: 4691020
    Abstract: 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: Grant
    Filed: July 23, 1984
    Date of Patent: September 1, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Ruechardt, Joachim Jaehme, Ulrich Salz
  • Patent number: 4622415
    Abstract: 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: Grant
    Filed: July 31, 1985
    Date of Patent: November 11, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Bernd Gallenkamp, Uwe Priesnitz, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4601797
    Abstract: 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: Grant
    Filed: March 1, 1985
    Date of Patent: July 22, 1986
    Assignee: Monsanto Company
    Inventor: John H. Wagenknecht
  • Patent number: 4589907
    Abstract: 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: Grant
    Filed: September 17, 1985
    Date of Patent: May 20, 1986
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4568497
    Abstract: Preparation of monoethers of dihydroxybenzenes from an alkenylphenol and an alkylating agent and thereafter oxidizing in the presence of an acid catalyst.
    Type: Grant
    Filed: May 29, 1984
    Date of Patent: February 4, 1986
    Assignee: The Dow Chemical Company
    Inventors: Abel Mendoza, Eric W. Otterbacher
  • Patent number: 4560786
    Abstract: .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: Grant
    Filed: June 24, 1982
    Date of Patent: December 24, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4552977
    Abstract: 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: Grant
    Filed: September 24, 1982
    Date of Patent: November 12, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Peter Herbrechtsmeier
  • Patent number: 4536483
    Abstract: 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: Grant
    Filed: October 26, 1983
    Date of Patent: August 20, 1985
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Yutaka Sasaki, Yutaka Kiyomiya, Toshio Nakamura, Yoshimi Nakamura, Masanori Yamaguchi
  • Patent number: 4531969
    Abstract: 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: Grant
    Filed: December 20, 1978
    Date of Patent: July 30, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans J. Nestler, Gerhard Horlein, Reinhard Handte, Hermann Bieringer, Friedhelm Schwerdtle, Peter Langeluddeke
  • Patent number: 4515985
    Abstract: 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: Grant
    Filed: December 16, 1981
    Date of Patent: May 7, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Husslein, Gerhard Hamprecht, Karl-Heinz Koenig, Walter Boehm, Manfred Gaeng
  • Patent number: 4492799
    Abstract: Novel halo-4-alkenoic acid compounds which are useful intermediates for the synthesis of insecticides and miticides.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: January 8, 1985
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4479900
    Abstract: 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: Grant
    Filed: April 29, 1983
    Date of Patent: October 30, 1984
    Assignee: Chevron Research Company
    Inventor: Tatao Luo
  • Patent number: 4468247
    Abstract: Salts, esters, amides, hydrazides and hydroxyamides of 4-methyl-4-[3'-(4"-trifluoromethylphenoxy)-phenoxy]crotonic acid are herbicidal against broad leaf plants.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: August 28, 1984
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • Patent number: 4459306
    Abstract: 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: Grant
    Filed: April 6, 1981
    Date of Patent: July 10, 1984
    Assignee: Science Union et Cie
    Inventors: Charles Malen, Jean-Claude Poignant
  • Patent number: 4456768
    Abstract: 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: Grant
    Filed: May 1, 1981
    Date of Patent: June 26, 1984
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4454344
    Abstract: 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: Grant
    Filed: August 23, 1982
    Date of Patent: June 12, 1984
    Assignee: American Cyanamid Company
    Inventor: Venkataraman Kameswaran
  • Patent number: 4444788
    Abstract: 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: Grant
    Filed: June 10, 1982
    Date of Patent: April 24, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
  • Patent number: 4429167
    Abstract: 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: Grant
    Filed: January 22, 1982
    Date of Patent: January 31, 1984
    Assignee: Zoecon Corporation
    Inventor: Shy-Fuh Lee
  • Patent number: 4418206
    Abstract: 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: Grant
    Filed: March 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Douglas L. Wren
  • Patent number: 4416687
    Abstract: 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: Grant
    Filed: February 1, 1982
    Date of Patent: November 22, 1983
    Assignee: Monsanto Company
    Inventors: John J. D'Amico, Tann R. Schafer
  • Patent number: 4380661
    Abstract: 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: Grant
    Filed: February 23, 1981
    Date of Patent: April 19, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Milos Suchy
  • Patent number: 4365991
    Abstract: 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: Grant
    Filed: March 6, 1981
    Date of Patent: December 28, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Wijitha de Silva
  • Patent number: 4360375
    Abstract: 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: Grant
    Filed: December 23, 1980
    Date of Patent: November 23, 1982
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kazuo Jikihara, Shigekazu Itoh, Shuichi Takayama, Koichi Sato, Ichiro Kimura, Isao Chiyomaru
  • Patent number: 4354034
    Abstract: 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: Grant
    Filed: June 15, 1979
    Date of Patent: October 12, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: John E. Barton, David J. Collins, Donald W. Headford
  • Patent number: 4348534
    Abstract: 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: Grant
    Filed: June 17, 1981
    Date of Patent: September 7, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Husslein, Gerhard Hamprecht
  • Patent number: 4348399
    Abstract: This disclosure describes novel 4-(monoalkylamino)phenyl alkane, alkene and alkyne carbinols, aldehydes, carboxylic acids and derivatives useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: February 2, 1978
    Date of Patent: September 7, 1982
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4347379
    Abstract: 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: Grant
    Filed: March 10, 1980
    Date of Patent: August 31, 1982
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 4345097
    Abstract: 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: Grant
    Filed: January 21, 1980
    Date of Patent: August 17, 1982
    Assignee: Vertac Chemical Corporation
    Inventors: Kenneth J. Howard, Albert E. Sidwell
  • Patent number: 4340765
    Abstract: 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: Grant
    Filed: August 14, 1980
    Date of Patent: July 20, 1982
    Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
  • Patent number: 4339587
    Abstract: Substituted 2-(trifluoroethoxy)benzamide, benzoic acid and benzoate compounds which are intermediates in the preparation of pharmaceutically active agents.
    Type: Grant
    Filed: June 8, 1981
    Date of Patent: July 13, 1982
    Assignee: Riker Laboratories, Inc.
    Inventor: Elden H. Banitt
  • Patent number: 4336382
    Abstract: 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: Grant
    Filed: August 25, 1980
    Date of Patent: June 22, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4332960
    Abstract: 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: Grant
    Filed: July 8, 1975
    Date of Patent: June 1, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Trosken, Gerhard Horlein, Ernst-Friedrich Schulze, Peter Langeluddeke
  • Patent number: 4332961
    Abstract: .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: Grant
    Filed: April 15, 1977
    Date of Patent: June 1, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4326882
    Abstract: 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: Grant
    Filed: April 26, 1979
    Date of Patent: April 27, 1982
    Assignee: PPG Industries, Inc.
    Inventors: Sidney B. Richter, William S. Grove
  • Patent number: 4310689
    Abstract: 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: Grant
    Filed: September 19, 1979
    Date of Patent: January 12, 1982
    Assignee: Akzo N.V.
    Inventors: Willem Eveleens, Johannes Spaans, Hendrik G. Wissink
  • Patent number: 4309547
    Abstract: 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: Grant
    Filed: May 30, 1980
    Date of Patent: January 5, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Koch, Hans J. Nestler
  • Patent number: 4304936
    Abstract: 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: Grant
    Filed: October 11, 1979
    Date of Patent: December 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
  • Patent number: 4303796
    Abstract: 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: Grant
    Filed: December 19, 1973
    Date of Patent: December 1, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4301295
    Abstract: 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: Grant
    Filed: August 20, 1980
    Date of Patent: November 17, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Helmut Nahm, Ernold Granzer
  • Patent number: 4293707
    Abstract: 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: Grant
    Filed: June 4, 1979
    Date of Patent: October 6, 1981
    Assignee: PPG Industries, Inc.
    Inventors: Sidney B. Richter, William S. Grove
  • Patent number: 4278678
    Abstract: 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: Grant
    Filed: November 16, 1979
    Date of Patent: July 14, 1981
    Assignee: Kaken Chemical Co., Ltd.
    Inventors: Yasuhiko Hamazaki, Kenji Seri, Nobuo Ishiyama, Toshiyuki Yamamoto, Masao Sakasai, Reiko Sato
  • Patent number: 4277612
    Abstract: 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: Grant
    Filed: January 28, 1980
    Date of Patent: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4270948
    Abstract: .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: Grant
    Filed: October 17, 1979
    Date of Patent: June 2, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
  • Patent number: 4269983
    Abstract: 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: Grant
    Filed: June 18, 1979
    Date of Patent: May 26, 1981
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish