Aromatic Acid Moiety Patents (Class 560/8)
  • Patent number: 4540811
    Abstract: A carboxylic acid esters, such as methyl propionate, is prepared by carbonylation of an olefin, such as ethylene, in the presence of an alcohol by the use of a molybdenum-nickel-alkali metal, a tungsten-nickel-alkali metal or a chromium nickel-alkali metal co-catalyst and in the presence of a halide.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: September 10, 1985
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4539161
    Abstract: Novel amine oxide compounds of the formula ##STR1## in which m is the integer 1 or 2, A is a through-conjugated radical of a fluorescent brightener system, which radical contains unsubstituted or non-chromophorically substituted aromatic carbocyclic and/or heterocyclic rings, X is a direct bond between A and Y, an oxygen atom or sulfur atom or a group of the formula --SO.sub.2 --, --SO.sub.2 --O--, --COO--, --CON(R)-- or --SO.sub.2 N(R)--, in which R is hydrogen or unsubstituted or non-chromophorically substituted alkyl, Y is an unsubstituted or non-chromophorically substituted straight-chain or branched alkylene or alkyleneoxyalkylene group, and R.sub.1 and R.sub.2 independently of one another are cycloalkyl, unsubstituted or non-chromophorically substituted alkyl or phenyl, or R.sub.1 and R.sub.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: September 3, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Leonardo Guglielmetti
  • Patent number: 4536591
    Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: August 20, 1985
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4532343
    Abstract: Aromatic retinoic acid analogues of the formula ##STR1## where X is hydrogen or fluorine, Y is hydrogen, halogen of atomic number 9 or 17, hydroxy, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms and R is hydroxy, alkoxy, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl, or aryl and R.sup.2 is alkyl or aryl, with the proviso that when Y is hydrogen, X is fluorine. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
    Type: Grant
    Filed: November 19, 1982
    Date of Patent: July 30, 1985
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Peter D. Hobbs
  • Patent number: 4526704
    Abstract: Compounds of the formula ##STR1## wherein n is 0 or 1; one of X.sup.1 and X.sup.2 is --COO-- or --OOC-- and the other is a single covalent bond or --CH.sub.2 CH.sub.2 --; X.sup.3 and X.sup.4 individually are a single covalent bond or --CH.sub.2 CH.sub.2 --, with the proviso that at most one of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 is --CH.sub.2 CH.sub.2 --; rings A.sup.1 and A.sup.5 individually are a group of the formula ##STR2## or trans-1,4-cyclohexylene; rings A.sup.2, A.sup.3 and A.sup.4 individually are a group of formula II or, when ring A.sup.2, A.sup.3 or A.sup.4 is not linked with at least one of the other two of these rings by a single covalent bond then such ring also can be trans-1,4-cyclohexylene, with the proviso that at least one of rings A.sup.1 through A.sup.5 is a group of formula II; Y is hydrogen, or when Y is attached to a ring of formula II which is not linked with another ring via a single covalent bond, Y also can be fluorine, chlorine or methyl; and R.sup.1 and R.sup.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: July 2, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
  • Patent number: 4515808
    Abstract: Pesticidal compounds have the formula: ##STR1## wherein D represents hydrogen or a cyano group or an ethynyl group R.sub.a represents alkylA represents an alkyl group or a halogeno or trifluoromethyl groupn is 0 or an integer of 1-4, b is 0 or 1andRCOO is the residue of an acid RCOOH whose .alpha.-cyano-3-phenoxybenzyl ester has pesticidal properties. They are prepared by esterification methods.
    Type: Grant
    Filed: July 26, 1983
    Date of Patent: May 7, 1985
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay
  • Patent number: 4513146
    Abstract: Ester is produced by reacting highly hindered carboxylic acid or salt thereof represented by the formula ##STR1## wherein a. R.sub.3, R.sub.4, and R.sub.5 are each independently a monovalent organo group, andb. M is hydrogen, monovalent metal, or the monovalent fractional part of a polyvalent metal,with organic carbonate represented by the formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently monovalent organic groups which may be the same or different, and wherein the alpha carbon of at least one of R.sub.1 and R.sub.2 is substantially sterically unhindered.
    Type: Grant
    Filed: September 23, 1982
    Date of Patent: April 23, 1985
    Assignee: PPG Industries, Inc.
    Inventor: Ralph B. Thompson
  • Patent number: 4492800
    Abstract: A process for the preparation of a 1,1-dichloro-alkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or together are alkanediyl,in the presence of at least an equimolar amount of magnesium. Advantageously,R.sup.1 is hydrogen,R.sup.2 is a C.sub.2 to C.sub.5 alkenyl radical or a radical of the formula ##STR4## Z is a cyano, acetal, carboxyl or C.sub.1 to C.sub.4 alkoxycarbonyl radical, or a radical of the formula COOM, andM is sodium or potassium,R.sup.3 each individually is a C.sub.1 to C.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: January 8, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4485252
    Abstract: 2-Phenyl-alk-1-enyl-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R each independently is hydrogen, halogen, cyano, nitro and, in each case optionally halogen-substituted, alkyl, alkoxy, alkylenedioxy or alkylthio,R.sup.1 is optionally halogen-substituted alkyk, andR.sup.2 is a radical customary in the alcohol part of pyrethroidswhich exhibit insecticidal and acaricidal activity. They are made from the corresponding alkyl esters which are new and made by novel processes.
    Type: Grant
    Filed: May 5, 1982
    Date of Patent: November 27, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4482731
    Abstract: The invention relates to a process for preparing trans-3-(Z-2-chloro-2-(4-aryl)-vinyl)-2,2-dimethyl-cyclopropane-1-carboxyl ic acid derivatives of Formula (I) from corresponding dehalogenated compounds of Formula (II) by dehalogenation. The invention also includes to the novel compounds of Formula (III) and a halogenation process for their production. The compounds of the invention are useful as intermediates and/or insecticides or acaricides.
    Type: Grant
    Filed: August 28, 1981
    Date of Patent: November 13, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Wilhelm Stendel
  • Patent number: 4480118
    Abstract: This invention relates to a novel carboxylic acid ester represented by the following general formula (I) and an insecticidal and/or acaricidal composition containing the same as an active ingredient: ##STR1## wherein X is represented by the formula, ##STR2## and further also relates to a carboxylic acid or a reactive derivative thereof represented by the general formula, ##STR3## wherein R.sub.16 is hydroxy group, chlorine or bromine atom, or a C.sub.1-2 alkoxy group, W is oxygen atom or --CH.sub.2 -- group, k is an integer of 0 or 1, E is hydrogen, chlorine, fluorine or bromine atom, and n is an integer of 1 to 4.
    Type: Grant
    Filed: December 30, 1981
    Date of Patent: October 30, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Makoto Hatakoshi, Toshihiko Yano, Nobushige Itaya
  • Patent number: 4470843
    Abstract: Herbicide antidote compounds having the formula ##STR1## in which X and X' are halogens, independently selected from the group consisting of chlorine, bromine and iodine; andR is selected from the group consisting of alkyl having 1-12 carbon atoms, inclusive; halophenyl wherein halo is selected from the group consisting of chlorine, bromine and iodine; and substituted alkoxy carbonyl wherein the alkoxy group has 1-8 carbon atoms, inclusive and the substituents are halogen selected from the group consisting of chlorine, fluorine, and iodine; or dioxane.
    Type: Grant
    Filed: October 14, 1980
    Date of Patent: September 11, 1984
    Assignee: Stauffer Chemical Company
    Inventor: Kent E. Matsumoto
  • Patent number: 4461910
    Abstract: A process for the co-production of an alkylidene dicarboxylate and a carboxylic acid, which comprises hydrogenating a carboxylic acid anhydride in the presence of carbon monoxide and a homogeneous iridium- and/or rhodium-containing catalyst, together with an organo phosphorus (III), arsenic (III), or antimony (III) compound and either molecular oxygen or a phosphorus (V), arsenic (V) or antimony (V) compound containing a X=O moiety, where X is a phosphorus, arsenic or antimony atom.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: July 24, 1984
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4461899
    Abstract: A series of ester and salt derivatives of fluorene-9-carboxylic acid and fluorene-1-carboxylic acid exhibit significant plant growth regulating properties, useful in controlling the size, shape, dormancy time, flowering time and/or fruit setting of plants, depending upon the concentrations used. They may also be used to control the growth rate, texture and color of turf grass. Presently preferred compounds include the cis-2,5-dimethylpyrrolidine salt of 1-fluorenecarboxylic acid, 9-cis-2,5-dimethyl-1-pyrrolidinyl-2-chlorofluorene-9-carboxylic acid, methyl ester, the 2,6-dimethylpiperidine salt of 1-fluorenecarboxylic acid, and the cis-2,5-dimethylpyrrolidine salt of 9-hydroxyfluorene-9-carboxylic acid.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: July 24, 1984
    Assignee: Diamond Shamrock Chemicals Company
    Inventors: William J. Pyne, Han S. Ku, Robert E. Holm
  • Patent number: 4440694
    Abstract: The invention relates to vinylstilbene compounds of the formula ##STR1## wherein Q is the grouping --COX or ##STR2## These compounds are obtained by reacting 1 molar equivalent of a compound of the formula II ##STR3## wherein X is chlorine, bromine or iodine, in the presence of a base and with the addition of palladium metal or of palladium compounds, as catalyst, which, under the reaction conditions, form labile palladium(O) compounds which do not contain phosphorus, with 1 molar equivalent of a compound of the formula III or with 1 molar equivalent of each of the compounds of the formulae III and IV ##STR4##
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: April 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Daniel Bellus, Hans-Ulrich Blaser, Guglielmo Kabas, Dieter Reinehr, Alwyn Spencer, Kurt Weber
  • Patent number: 4440663
    Abstract: Alkaline aqueous liquid detergent compositions comprising zeolite A, a nonionic surfactant, a polycarboxylate detergency builder and an unsaturated soap which are substantially free of synthetic anionic surfactants that can contain normally unstable ester perfumes without a stability problem.
    Type: Grant
    Filed: October 8, 1982
    Date of Patent: April 3, 1984
    Assignee: The Procter & Gamble Company
    Inventors: Stanton L. Boyer, Charles A. Schulz
  • Patent number: 4439614
    Abstract: 5,6-Methano-5,6-dihydroretinoids such as ethyl (E)-5,6-methano-5,6-dihydroretinoate and (E)-1-(4-carbethoxyphenyl)-2-methyl-4-(2,2,6-trimethylbicyclo[4.1.0]hept-1 -yl)-1,3-butadiene are disclosed. These componds are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: March 27, 1984
    Assignee: SRI International
    Inventors: Marcia I. Dawson, Rebecca Chan, Peter D. Hobbs
  • Patent number: 4439015
    Abstract: Disubstituted ethanes of the formula ##STR1## wherein R.sup.2 is --R.sup.3, --OR.sup.3, --CO--R.sup.3, --CO--OR.sup.3 or O--CO--R.sup.3, R.sup.1 and R.sup.3 each are straight-chain alkyl of 1 to 12 carbon atoms and n is 1 or 2,are described. Liquid crystalline mixtures comprising Compound I as well as their use in electro-optical devices also are disclosed.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: March 27, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Roland Rich, Alois Villiger, Erich Widmer
  • Patent number: 4433165
    Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer component selected from N,N,N',N'-tetramethyl-o-phenylenediamine and 2,3'-dipyridyl.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventor: Thomas C. Singleton
  • Patent number: 4433166
    Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: February 21, 1984
    Assignee: Monsanto Company
    Inventors: Thomas C. Singleton, Frank E. Paulik
  • Patent number: 4425282
    Abstract: A process for the preparation of a 3-(arylvinyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid ester of the formula ##STR1## in which Ar is an aromatic radical,R is alkyl or an alcohol radical customary in pyrethroids, andR.sup.1 is hydrogen, fluorine or chlorine,comprising reacting a compound of the formula ##STR2## with respectively, one, two or three equivalents of a base at a temperature between about -20.degree. and +60.degree. C. The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.
    Type: Grant
    Filed: April 7, 1980
    Date of Patent: January 10, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
  • Patent number: 4424166
    Abstract: In the preparation of a 1,1-dihalogenoalkene of the formula ##STR1## in which R.sup.1 is a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain, andX.sup.1 and X.sup.2 each independently is a halogen atom,wherein a carbonyl compound of the formula ##STR2## is reacted with a trihalogenoacetate of the formula ##STR3## in which X.sup.3 is a halogen atom, andM.sup..sym. is an alkali metal ion or one equivalent of an alkaline earth metal ion,in the presence of an approximately equimolar amount of a phosphorus-containing compound, the improvement which comprises employing as said phosphorus-containing compound a phosphorous acid trialkyl ester or a phosphorous acid triamide and effecting the reaction at a temperature between about 0.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: January 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4423066
    Abstract: A pentafluorobenzyl 2,2-dimethyl-3-vinylcyclopropane carboxylate of the formula ##STR1## in which R is hydrogen or halogen, andR.sup.1 is optionally substituted phenyl, orR and R.sup.1 together constitute an alkylene chain with at least two carbon atoms,which possess arthropodicidal properties.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: December 27, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4407823
    Abstract: Phenylacetic acid derivatives of the formula ##STR1## wherein n is an integer of 2 to 5; ##STR2## R.sub.1 is hydrogen, halogen, trifluoromethyl, nitro or amino; R.sub.2 and R.sub.3 each independently is hydrogen or lower alkyl; or together form an ethylene group;X.sub.1 represents two hydrogen atoms or an oxo group; andY.sub.1 is cyano, hydroxyamidocarbonyl, carbamoyl, 5-tetrazolyl or carboxyl;and for derivatives wherein Y is carboxyl, salts thereof with physiologically compatible bases, esters thereof from physiologically acceptable alcohols and amides thereof from physiologically acceptable amines have valuable pharmacological activity, e.g., as antiinflammatory agents.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: October 4, 1983
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerald Kirsch, Joachim-Friedrich Kapp, Clemens Rufer
  • Patent number: 4402973
    Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: September 6, 1983
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • 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
  • Patent number: 4390721
    Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.
    Type: Grant
    Filed: November 1, 1978
    Date of Patent: June 28, 1983
    Assignee: Allen & Hanburys Limited
    Inventor: Stanley M. Roberts
  • Patent number: 4388312
    Abstract: New quinone derivatives of the formula: ##STR1## wherein R.sup.1 is methyl or methoxy, or two of R.sup.1 combine to represent --CH.dbd.CH--CH.dbd.CH--, R is amino which may be substituted or --OR.sup.4 wherein R.sup.4 is hydrogen, C.sub.1-4 alkyl or --CH.sub.2 --CH.dbd.C(CH.sub.3 --CH.sub.2 --.sub.m H (wherein m is an integer of 1 to 10), and n is an integer of 1 to 10 when R is amino which may be substituted, or n is an integer of 2 to 10 when R is --OR.sup.4, and their hydroquinone forms, have useful physiological activities such as blood-pressure decreasing and antiallergic activities.
    Type: Grant
    Filed: August 26, 1980
    Date of Patent: June 14, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Shinji Terao, Mitsuru Shiraishi, Kaneyoshi Kato
  • Patent number: 4370345
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 denotes H, halogen, alkyl or CF.sub.3, R.sup.2 denotes H, halogen, alkyl or CF.sub.3, R.sup.3 denotes H, halogen, CN or alkyl, R.sup.4 denotes H, halogen, alkyl, phenyl or halogenophenyl, R.sup.5 denotes H, alkyl, alkynyl or CN and R.sup.6 denotes substituted dimethylcyclopropyl or 2-phenylisobutyl radicals, are effective insecticides and acaricides of the pyrethroid type.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: January 25, 1983
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Welter, Hilmar Mildenberger, Werner Knauf, Anna Waltersdorfer, Werner Bonin
  • Patent number: 4362744
    Abstract: Disclosed are novel compounds of the formula ##STR1## in which R.sup.1 is hydrogen or methyl; R.sup.2 is phenyl or phenyl-methyl either of which is optionally ring substituted with lower alkyl or halogen; R is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substitutedphenyl)-2-methylpropylcarbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substitutedvinylcyclopropanecarbonyl group; and, with respect to the indanyl substituents, the 1,3-trans isomer is present in an isomeric excess over the corresponding 1,3-cis isomer. The compounds wherein R is other than hydrogen are insecticides, and the compounds wherein R is hydrogen are insecticide intermediates.
    Type: Grant
    Filed: March 19, 1981
    Date of Patent: December 7, 1982
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4360689
    Abstract: New .alpha.-halobenzyl esters, intermediates for .alpha.-cyanobenzyl pyrethroid esters, are prepared by treating a benzaldehyde derivative with a pyrethroid acid halide. The resulting .alpha.-halobenzyl ester is treated with a water-soluble compound capable of generating cyanide ions (CN.sup.-) to give the corresponding .alpha.-cyanobenzyl esters.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: November 23, 1982
    Assignee: Shell Oil Company
    Inventor: Charles H. Tieman
  • Patent number: 4359580
    Abstract: The invention is an improved process for the preparation of lower alkyl esters of tetrahydrothiophenium carboxymethylide intermediates of insecticidal pyrethroids, and to insecticidal prethroids derived from said ylides.
    Type: Grant
    Filed: February 12, 1981
    Date of Patent: November 16, 1982
    Assignee: American Cyanamid Company
    Inventor: Charles P. Grasso
  • Patent number: 4358409
    Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: November 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4358607
    Abstract: The invention is a novel chloro-substituted cyclopropane carboxylic acid useful for the preparation of novel insecticidal-acaricidal pyrethroids.
    Type: Grant
    Filed: July 21, 1978
    Date of Patent: November 9, 1982
    Assignee: American Cyanamid Co.
    Inventor: Dale G. Brown
  • Patent number: 4344963
    Abstract: 2-Phenyl-alk-1-enyl-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R each independently ishydrogen, halogen, cyano, nitro and, in each case optionally halogen-substituted, alkyl, alkoxy, alkylenedioxy or alkylthio,R.sup.1 is optionally halogen-substituted alkyk, andR.sup.2 is a radical customary in the alcohol part of pyrethroidswhich exhibit insecticidal and acaricidal activity. They are made from the corresponding alkyl esters which are new and made by novel processes.
    Type: Grant
    Filed: April 25, 1980
    Date of Patent: August 17, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
  • Patent number: 4340498
    Abstract: New halogenated ester derivatives and liquid crystal compositions containing the same are provided. The derivatives are expressed by the general formula ##STR1## wherein X is ##STR2## R is 1-15C alkyl group or alkoxy group; and Y is carboxyl group. The derivatives are useful as component(s) of liquid crystal compositions which have higher mesomorphic temperature ranges, nevertheless have lower viscosities; and also have lower absolute values of dielectric anisotropy, nevertheless can be driven at lower voltages.
    Type: Grant
    Filed: January 23, 1981
    Date of Patent: July 20, 1982
    Assignee: Chisso Corporation
    Inventor: Shigeru Sugimori
  • Patent number: 4335249
    Abstract: Diphenyl ethers of the formula ##STR1## wherein R.sup.1 is hydrogen or halogen,R.sup.2 is hydrogen, halogen, or cyano,R is ##STR2## wherein R.sup.3 is hydrogen, halogen, nitro, alkyl, or alkoxy,R.sup.4 is a divalent alkylene radical, andR.sup.5 is cyano or --COR.sup.6, wherein R.sup.6 is alkoxy, hydroxy or salt thereof, allyloxy, alkoxyalkoxy, amino, alkyl or dialkyl amino, aminoalkoxy, or alkyl or dialkylaminoalkoxy,and diphenyl sulfides, sulfoxides, and sulfones of the formula ##STR3## wherein R.sup.8 is hydrogen, halogen, cyano, nitro, alkyl, alkoxy, or trifluoromethyl,R.sup.2 is hydrogen, halogen or cyano,X is sulfur, sulfinyl, or sulfonyl, andR is as defined above,and compositions containing these compounds exhibit herbicidal activity.
    Type: Grant
    Filed: July 30, 1976
    Date of Patent: June 15, 1982
    Assignee: Rohm and Haas Company
    Inventors: Wayne O. Johnson, Roy Y. Yih
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4333950
    Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: June 8, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4332815
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 1, 1980
    Date of Patent: June 1, 1982
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4330482
    Abstract: In the process for the production of a halogenoalkene of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl or aryl radical or an optionally substituted heterocyclic radical,R.sup.2 represents a halogen atom, a cyano group, an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkenyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl or aminocarbonyl radical or an optionally substituted heterocyclic radical, andX is a halogen atom,in which an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R.sup.3 each independently is an alkyl or phenyl radical, or the two radicals R.sup.3 together are an alkanediyl (alkylene) radical,is reacted with a phosphorus-containing olefinating agent of the formula ##STR3## in which Z.sup.1 is the phosphorus-containing radical ##STR4## R.sup.4 and R.sup.5 each independently is an alkyl, phenyl, alkoxy or phenoxy radical or together are an alkanedioxy radical, andR.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: May 18, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hellmut Hoffmann
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4323513
    Abstract: This invention is concerned with improving ethylene glycol ester production from the reaction of carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and acyl compound by maintaining the combined concentration of methyl ester, ethylene glycol ester and water in the reaction medium at less than about 30 volume percent. In a preferred embodiment, a continuous process is operated in such a manner that the methyl ester, ethylene glycol ester and water products are removed from the reactor so as to maintain their total volume concentration in the reaction medium at less than about 30 percent.
    Type: Grant
    Filed: November 4, 1980
    Date of Patent: April 6, 1982
    Assignee: Union Carbide Corporation
    Inventor: Bernard D. Dombek
  • Patent number: 4323495
    Abstract: Novel branched-chain monoalcohols and derivatives thereof are disclosed. Such derivatives are selected from the group consisting of(a) esters of aromatic, aliphatic or cycloaliphatic acids having at least 2 carbon atoms and 1, 2 or 3 carboxyl groups;(b) urethanes of aromatic, aliphatic or cycloaliphatic isocyanates;(c) monoethers of polyalkylene oxide glycols having 2 to 50 alkylene oxide units each containing 2 or 3 carbon atoms and the alkylpolyoxyalkylene sulfates derived therefrom;(d) sulfates.The branched-chain monoalcohols are obtained by reduction of branched-chain monocarboxylic acids or esters thereof. Said acids are telomeric acids obtained by the free radical addition of 1 mole of acetic anhydride to at least three moles of hexene and/or higher olefins containing up to 30 or more carbon atoms (C.sub.30+) in the presence of a trivalent manganese compound. The products of this invention are suitable for use in engine lubricating oils, lubricant compositions for polymers and wax compositions.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: April 6, 1982
    Assignee: Akzona Incorporated
    Inventors: Jacobus J. Zeilstra, Willem J. de Klein, Joannes D. Bik
  • Patent number: 4317834
    Abstract: Fluorine-substituted spirocarboxylic acid benzyl esters of the formula ##STR1## in which R.sup.1 represents hydrogen, cyano or alkyl, alkenyl or alkynyl, with in each case up to 4 carbon atoms,R.sup.2 represents a phenyl radical which is substituted by halogen and/or by optionally halogen-substituted phenoxy, with the proviso that the radical R.sup.2 contains in total at least one fluorine substituent, andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 each represent hydrogen, halogen or alkyl, orR.sup.3 and R.sup.4, taken together, and/or R.sup.5 and R.sup.6, taken together, represent alkanediyl (alkylene) or a fused-on benzo radical,and the C atoms of the 5-member spirocyclic ring are linked to one another either by double bonds or by single bonds, which possess arthropodicidal properties.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: March 2, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
  • Patent number: 4317782
    Abstract: Distyryl compounds of the formula ##STR1## wherein A denotes 1,4-phenylene, 4,4'-biphenylylene, 4,4"-terphenylylene, 1,4-, 1,5- or 2,6-naphthylene, 9,10-dihydro-2,7-phenanthrenylene or 2,7-dibenzofuranylene,R.sup.1 denotes an optionally functionally modified phosphonic acid, phosphonyl or phosphinyl group,R.sup.2 denotes hydrogen, an optionally functionally modified phosphonic acid, phosphonyl or phosphinyl group, sulpho, carboxyl, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, aminocarbonyl, cyano, halogen, alkyl, aralkyl, alkenyl, hydroxyl, alkoxy, aralkoxy, cycloalkoxy, aryloxy or alkylmercapto andR.sup.3 and R.sup.
    Type: Grant
    Filed: February 22, 1979
    Date of Patent: March 2, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Eckstein, Edgar Siegel
  • Patent number: 4316046
    Abstract: A process for the preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted with an aryliodoso carboxylate in liquid medium to form the desired aryl carboxylate. Promoters can be employed to increase the rate of reaction and improve selectivity to the aryl carboxylate.
    Type: Grant
    Filed: August 29, 1980
    Date of Patent: February 16, 1982
    Assignee: The Halcon SD Group, Inc.
    Inventor: Lawrence C. Costa
  • Patent number: 4305885
    Abstract: A perfluoroalkane-sulphinic acid of the formula R.sub.F --SO.sub.2 H is reacted with a diene at -20.degree. to +20.degree. C. to form the new intermediate ##STR1## in which R.sup.3 -R.sup.8 are hydrogen or various organic radicals or double bonds, and that is reacted with a .beta.,.beta.-dimethyl-acrylic acid derivative of the formula ##STR2## in the presence of a base at a temperature between about -20.degree. and +30.degree. C. to produce a cyclopropane carboxylic acid derivative of the formula ##STR3## in which Z is alkoxycarbonyl or cyano and R.sup.1 and R.sup.2 are hydrogen or various organic radicals. The products are known intermediates for insecticides.
    Type: Grant
    Filed: June 27, 1980
    Date of Patent: December 15, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Hanack, Theodor Stoll
  • Patent number: 4302527
    Abstract: There are disclosed light-sensitive compounds and a composition comprising (a) such compounds and (b) a compound having at least one reactive site capable of stepwise photo-reaction with the light-sensitive compounds. The light-sensitive compounds have the structural formula, ##STR1## wherein Z.sup.1 and Z.sup.2 are each independently the number of non-metallic atoms necessary to complete 1, 2, 3, or 4 unsaturated carbocyclic or heterocyclic rings of from 6 to 18 nuclear atoms;Z.sup.3 is either a carbon-to-carbon bond or vinylene;and X is a linking group.The composition can be applied to a variety of supports and photoreacted by exposure to activating radiation.
    Type: Grant
    Filed: August 21, 1980
    Date of Patent: November 24, 1981
    Assignee: Eastman Kodak Company
    Inventors: Robert C. Daly, Danny R. Thompson, Samir Y. Farid