Patents Examined by Dolph H. Torrence
  • Patent number: 4406841
    Abstract: A process for producing 2,6-difluorobenzonitrile comprises reducing a chloro fluorobenzonitrile selected from 3-chloro-2,6-difluorobenzonitrile, 3,5-dichloro-2,6-difluorobenzonitrile or a mixture thereof by hydrogen gas in the presence of a palladium or platinum catalyst at a temperature of 0.degree. to 200.degree. C.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: September 27, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Yasuhiro Tsujii, Shigeo Murai, Hisayoshi Jyonishi
  • Patent number: 4405528
    Abstract: 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenols having the formula ##STR1## wherein R is methyl, ethyl, n-propyl or isopropyl are prepared by reacting a di-substituted phenol, such as 2,6-di-tertiary-butyl phenol, with a Friedel-Crafts addition agent in the presence of a Friedel-Crafts catalyst such as aluminum chloride to form the corresponding 4-(.alpha.-alkyl-.alpha.-oxo-methyl)2,6-di-substituted phenol. The 4-(.alpha.-alkyl -.alpha.-oxo-methyl)2,6-di-substituted phenol thus formed readily can be reduced to form the corresponding 4-(.alpha.-alkyl-.alpha.-hydroxy-methyl)2,6-di-substituted phenol which thereafter can be reacted with an alkali metal or an alkaline earth metal cyanide to form the desired 4-(.alpha.-alkyl-.alpha.-cyano-methyl)2,6-di-substituted phenol. This can be converted by hydrolysis into the corresponding .alpha.-alkyl-4-hydroxyphenylacetic acid. These acids are well-known insecticidal and acaricidal intermediates.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventor: Charles Everly
  • Patent number: 4405529
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 20, 1983
    Assignee: American Cyanamid Company
    Inventors: Jack K. Siddens, Sivaraman Raghu
  • Patent number: 4405527
    Abstract: Polyisocyanates are prepared by reacting a polyamine solution with a phosgene solution. Excess phosgene and hydrogen chloride formed during the reaction are removed from the reaction mixture. The solvent is subsequently removed from the reaction mixture (e.g., by evaporation and condensation) and treated with a compound containing isocyanate reactive hydrogen atoms to convert any isocyanates present into urethanes and/or ureas. The thus-treated solvent may then be reused, preferably after any urethanes and/or ureas present in the solvent have been removed.
    Type: Grant
    Filed: July 12, 1982
    Date of Patent: September 20, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Wegener, Hartmut Knofel, Gunther Ellendt, Marcel Petinaux
  • Patent number: 4405639
    Abstract: Fluorine-containing phenylacetic acid esters of the formula ##STR1## in which R represents the radical of an alcohol customary in the case of pyrethroids,R.sup.1 represents C.sub.2-4 -alkyl, C.sub.2-4 -alkenyl or cyclopropyl,X represents H, halogen, alkyl, alkoxy, OCHF.sub.2, SCHF.sub.2, SCClF.sub.2 or SCF.sub.3 andX.sup.1 can vary widely or form a fused ring with X,the overall compound necessarily containing a fluorine atom, which compounds possess arthropodicidal properties. Intermediates therefor and an overall synthesis from an alcohol of the formula ROH and a toluene of the formula ##STR2## are also shown.
    Type: Grant
    Filed: May 3, 1982
    Date of Patent: September 20, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Erich Klauke, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel, Reinhard Lantzsch, Albrecht Marhold
  • Patent number: 4404148
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 13, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4404021
    Abstract: This application discloses the compound, .alpha.-cyanobenzyl-3,6-dichloro-2-methoxybenzoate, useful as a herbicide.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: September 13, 1983
    Assignee: Velsicol Chemical Corporation
    Inventor: Jerome A. Gourse
  • Patent number: 4401673
    Abstract: Novel 3-(buta-1',3'-dienyl)-cyclopropane-1-carboxylic acid compounds of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually a halogen and A is selected from the group consisting of (A) benzyl optionally substituted (B) ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen and --CH.sub.3 and R.sub.2 is selected from the group consisting of aryl and --CH.sub.2 --C.tbd.CH, (C) ##STR3## wherein R.sub.3 is an aliphatic of 2 to 6 carbon atoms containing at least one carbon-carbon unsaturation, (D) ##STR4## wherein R'.sub.1 and R'.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and cyano and R.sub.3 has the above definition, (E) ##STR5## wherein R.sub.4 is selected from the group consisting of hydrogen, --CN, --CH.sub.3, --CONH.sub.2, --CSNH.sub.2 and --C.tbd.CH, R.sub.5 is selected from the group consisting of chlorine and --CH.sub.
    Type: Grant
    Filed: January 26, 1981
    Date of Patent: August 30, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Pierre Girault
  • Patent number: 4401602
    Abstract: Compounds, such as 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitroacetophenone oxime-O-(acetic acid, methyl ester) and 5-(2-chloro-4-trifluoromethylphenoxy)-2-chloroacetophenone oxime-O-(acetic acid, methyl ester), are useful for postemergence and preemergence control of weeds, and are represented by Formula I of the application.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: August 30, 1983
    Assignee: PPG Industries, Inc.
    Inventor: Dennis K. Krass
  • Patent number: 4401603
    Abstract: An improved process for preparation of arylisocyanide dichloride by chlorinating N-arylformamide in the presence of thionyl chloride wherein the improvement comprises preparing the N-arylformamide by formylation of an arylamine having 6 to 12 aryl carbon atoms with a formylating agent in an inert solvent.removing excess formylating agent and by-products of the formylation thereby leaving the N-arylformamide in the form of a solution or suspension in the inert solvent and chlorinating the N-arylformamide in solution or suspension with a chlorinating agent in the presence of thionyl chloride.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: August 30, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventors: Dieter Ferchland, Ulrich Kussmaul, Manfred Langer, Rolf Muller
  • Patent number: 4400205
    Abstract: The m-Cyanoalkoxy-phenylureas of the formula I ##STR1## wherein X is hydrogen or halogen, Y--O is a preferably branched-chain cyanoalkoxy group, and --NR.sub.1 R.sub.2 is a primary, secondary or heterocyclic amino group, exhibit surprisingly good herbicidal activity against mono- and dicotyledonous plants, with a selective action in crops of maize, cereals, cotton and soya bean, and in the case of some of these compounds also in rape crops.
    Type: Grant
    Filed: January 18, 1982
    Date of Patent: August 23, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg Pissiotas, Otto Rohr
  • Patent number: 4399074
    Abstract: A process for the production of tertiary alkyl isocyanates, such as tetramethylxylylene diisocyanates, is disclosed in which the corresponding tertiary alkyl halide is reacted with an alkali metal cyanate utilizing a zinc-pyridine complex as a catalyst which has been prereacted with the cyanate before reaction with the halide.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: August 16, 1983
    Assignee: American Cyanamid Company
    Inventor: Frederic C. Schaefer
  • Patent number: 4399073
    Abstract: A process for the production of tertiary alkyl isocyanates, such as tetramethylxylylene diisocyanate, is disclosed in which the corresponding tertiary alkyl halide is reacted with an alkali metal cyanate in the presence of water in an amount between 0.02 and 0.2 percent based on the weight of the reaction mixture.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: August 16, 1983
    Assignee: American Cyanamid Company
    Inventor: Frederic C. Schaefer
  • Patent number: 4399076
    Abstract: 2-Vinyl- and 2-ethylcyclopropanes having an aryl group and a nitrogen-containing radical substituted at the 1-position on the ring are provided. The novel 1,1-disubstituted 2-vinylcyclopropane and 2-ethylcyclopropane compounds of this invention have utility in herbicidal applications and are useful reactants. The 2-vinylcyclopropane derivatives are useful monomers for anionic and radical polymerizations.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: August 16, 1983
    Assignee: National Distillers and Chemical Corporation
    Inventors: Richard G. Fayter, Jr., Allen L. Hall
  • Patent number: 4395369
    Abstract: A process for production of tertiary aralkyl isocyanates by reaction at low temperatures of the corresponding halides with an excess of isocyanic acid. Manufacture of TMXDI is specifically contemplated.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 26, 1983
    Assignee: American Cyanamid Company
    Inventors: William A. Henderson, Jr., Balwant Singh
  • Patent number: 4395372
    Abstract: A process is disclosed for alkylation of benzenes with lower olefins which comprises contacting the benzene and lower olefin with a rare earth exchanged X or Y zeolite catalyst in the presence of sulfur dioxide.
    Type: Grant
    Filed: August 9, 1982
    Date of Patent: July 26, 1983
    Assignee: Shell Oil Company
    Inventors: Robert Q. Kluttz, Lynn H. Slaugh
  • Patent number: 4394327
    Abstract: 3-Phenoxy-.alpha.-phenoxy-alkanecarboxylic acid derivatives of the formula ##STR1## Wherein Hal is a halogen atom, n is an integer from 1 to 3, R is an acid function and Z is hydrogen or C.sub.1 -C.sub.4 alkyl, are disclosed as possessing a surprising selective herbicidal activity. 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: May 14, 1981
    Date of Patent: July 19, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
  • Patent number: 4394152
    Abstract: Sulfur-containing oxime compounds of the formula I given herein are suitable for protecting cultivated plants against the phytotoxic action of aggressive agricultural chemicals, particularly herbicides. There are described methods for producing sulfur-containing oxime compounds of this type, and examples are given illustrating the application of these compounds.
    Type: Grant
    Filed: May 4, 1981
    Date of Patent: July 19, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Elmar Sturm, Heinrich Schempp, Henry Martin
  • Patent number: 4393008
    Abstract: 2-(3-phenoxy-phenyl)-propionic acid or its pharmaceutical treatments, are prepared by hydrolyzing and partially decarboxylating ##STR1## wherein R=C.sub.1 -C.sub.6 alkyl or amino, the latter compounds being themselves new and, where R=C.sub.1 -C.sub.6 alkyl, have antiinflammatory pharmaceutical properties.
    Type: Grant
    Filed: August 12, 1981
    Date of Patent: July 12, 1983
    Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt
    Inventors: Endre Palosi, Gergely Heja, Dezso Korbonits, Pal Kiss, Csaba Gunczi, Judit Cser, Ida Szvoboda, Gabor Szabo, Tamas Kallay, Laszlo Ledniczky, Maria Szomor
  • Patent number: 4391731
    Abstract: Compounds of the formula ##STR1## wherein ring A is saturated or aromatic and a saturated ring A which may be present is trans-linked with the second ring; R.sup.1 is a straight-chain alkyl or alkoxy group containing 1 to 11 carbon atoms; R.sup.2 is cyano, a straight-chain alkyl group containing 1 to 11 carbon atoms, an ester group of the formula ##STR2## or, when ring A is saturated, additionally a straight-chain alkoxy group containing 1 to 11 carbon atoms; in the ester group of formula II ring B is either aromatic and X is oxygen or sulfur and R.sup.3 is cyano or a straight-chain alkyl or alkoxy group containing 1 to 10 carbon atoms, or ring B is a trans-1,4-disubstituted cyclohexane ring and X is oxygen and R.sup.3 is cyano or a straight-chain alkyl group containing 1 to 10 carbon atoms; and the total number of carbon atoms in the alkyl and/or alkoxy groups amounts to at most 12, are described. The compounds of formula I are useful in liquid crystal mixtures.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: July 5, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Arthur Boller, Martin Schadt, Alois Villiger