Halogen Containing Patents (Class 568/812)
  • Patent number: 5118881
    Abstract: The present invention provides for an improved practical process for producing DDTr-free p,p'-dicofol and its formulations substantially free of the practically inactive o-p'-dicofol comprising either directly recrystallizing technical dicofol from a suitable solvent such as acetic acid or alkanes, or alternatively preparing the p,p'-dicofol by the steps of (a) dehydrohalogenating technical DDT to give DDE; (b) chlorinating DDE to give Cl-DDT; and (c) hydrolyzing Cl-DDT to dicofol, wherein the technical DDT is initially recrystallized from a suitable solvent such as lower alkyl alcohols and then recrystallizing the ressulting p,p'-dicofol from a suitable solvent such as acetic acid or alkanes.
    Type: Grant
    Filed: November 8, 1990
    Date of Patent: June 2, 1992
    Assignee: Agan Chemical Manufacturers, Ltd.
    Inventors: Bernard Vaisbuch, Benjamin Shifman, Michael Pikarski
  • Patent number: 5116981
    Abstract: This invention encompasses novel analogs of Leukotriene B.sub.4 which are selected from a compound of formula I, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--Y--C(M.sub.1)--A, or formula II, B--C.apprxeq.C--CH.sub.2 C(M.sub.2)--C.apprxeq.C--P--R.sub.5 --A: wherein Y is: ##STR1## wherein P is: ##STR2## Patentable intermediates, process for making the novel analogs and intermediates and preparation of useful pharmacological agents comprising the analogs and intermediates are part of this invention.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: May 26, 1992
    Assignee: The Upjohn Company
    Inventor: Joel Morris
  • Patent number: 5081319
    Abstract: 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol is separated from a mixture comprising by way of the formation of an addition compound between 1,1-bis(4-chlorophenyl)-2,2,2-trichloroethanol and a moderately electron donating compound, preferably selected from a group formed by dimethyl sulphoxide, cyclohexanone, isophoron, pyridine, 1,4-dioxane, acetic acid, acetonitrile and water.
    Type: Grant
    Filed: July 18, 1990
    Date of Patent: January 14, 1992
    Assignee: Sociedad Espanola de Desarrollos Quimicos S.A.
    Inventors: Jaime Palencia Adrubau, Jaume Castella Sola
  • Patent number: 5081317
    Abstract: 1-Bromo-3-chloro-1,2-diaryl-2-propanols of the general formula I ##STR1## where n and m are each 1, 2 or 3, and R.sup.1 and R.sup.2 are each hydrogen, haloalkyl, alkoxy, haloalkoxy, t-butyl or an aromatic radical which may be substituted, are prepared and converted into azolylmethyloxiranes.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reiner Kober, Heinz Isak, Rainer Seele
  • Patent number: 5075512
    Abstract: A process for purifying technical grade 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol for reducing its content of DDT related impurities, based on dissolving technical grade dicofol in a mixture of water and a first compound selected from the group formed by ethylene glycol monomethyl ether, acetonitrile, hydroxyacetone or dimethyl sulfoxide, to obtain a solution which is extracted with n-decane, separating the resulting phases. The dicofol extracted with the n-decane is recovered by reextraction of the n-decane phase with mixtures of said first compound and water and the purified dicofol is recovered from the polar phase.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: December 24, 1991
    Assignee: Sociedad Espanola de Desarrollos Quimicos S.A.
    Inventors: Jaime Palencia Adrubau, Jaume Castella Sola
  • Patent number: 5072037
    Abstract: A process for the preparation of 2-(4-chlorophenyl)-3-methylbutyric acid from 4-chlorobenzaldehyde by conversion of the benzaldehyde to 3-(4-chlorophenyl)-2-methylpropenal, 3-(4-chlorophenyl)-2-methylpropanol, 1-(4-chlorophenyl)-2-methylpropene-1, and 2-(4-chlorophenyl)-2-methylbutyraldehyde, and finally to the desired corresponding butyric acid.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: December 10, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Peter Lappe, Helmut Springer
  • Patent number: 5066815
    Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: November 19, 1991
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
  • Patent number: 5057626
    Abstract: A process for the synthesis of alpha,alpha-difluoroketones from alpha,alpha-difluoroacylsilanes and intermediates therefor.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: October 15, 1991
    Assignee: Pfizer Inc.
    Inventor: Peter A. McCarthy
  • Patent number: 5017730
    Abstract: The invention provides a process for easily, efficiently and economically preparing bis(trifluoromethylphenyl)methanol from either toluoyl chloride or a trihalomethylbenzoyl chloride. First the starting compound is reacted with toluene in the presence of a strong acid catalyst such as a perfluoroalkylsulfonic acid to form a benzophenone derivative, CX.sub.3 C.sub.6 H.sub.4 --CO--C.sub.6 H.sub.4 CH.sub.3, wherein X is H, F, Cl or Br. Next, by chlorination the benzophenone derivative is converted into CY.sub.3 C.sub.6 H.sub.4 --CO--C.sub.6 H.sub.4 CCL.sub.3, wherein Y is F or Cl, and then the chlorinated intermediate is fluorinated into bis(trifluoromethyl)benzophenone. By reduction of carbonyl group of this benzophenone derivative the aimed compound is obtained.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: May 21, 1991
    Assignee: Central Glass Company, Limited
    Inventors: Yoshihiko Gotoh, Toshikazu Kawai, Junji Negishi
  • Patent number: 4990693
    Abstract: Novel physiologically active substances KS-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: February 5, 1991
    Assignee: Kyowa Hakko Kogyo Co. Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
  • Patent number: 4990677
    Abstract: Fungicidal and plant growth-regulating azolylmethylcyclopropyl derivatives of the formula ##STR1## in which R represents halogen, alkyl or optionally substituted phenyhl, or represents the groupings --Y--R.sup.2,whereinY represents oxygen, sulphur, SO or SO.sub.2 andR.sup.2 represents optionally substituted phenyl,R.sup.1 represents hydrogen, alkyl or acyl,X represents nitrogen or a CH group,Z represents halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 halogen atoms or phenyl which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen, or represents phenoxy which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen andm represents the number 0, 1, 2 or 3, and addition products thereof with acids and metal salts.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
  • Patent number: 4990689
    Abstract: By reacting fluorobenzene with hexafluoroacetone in the pressure of a Lewis acid catalyst, e.g. aluminum chloride, a novel compound 2,4-bis(2-hydroxyhexafluoro-2-propyl)fluorobenzene is formed at high yield with little formation of isomers. The novel compound is useful as a cross-linking agent for some polymers and also as a material of some polymers.
    Type: Grant
    Filed: June 20, 1989
    Date of Patent: February 5, 1991
    Assignee: Central Glass Company, Limited
    Inventors: Masamichi Maruta, Takayuki Nishimiya
  • Patent number: 4987236
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom, R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: January 22, 1991
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4973767
    Abstract: The invention provides a process for the preparation of a compound of the general formula (I): ##STR1## wherein X, Y and R.sup.1 to R.sup.7 are as defined. In the process, the olefinic analog of the compound of general formula (I) is treated with a halogen-bearing compound in the presence of metallic zinc.
    Type: Grant
    Filed: December 12, 1988
    Date of Patent: November 27, 1990
    Assignee: Sandoz Ltd.
    Inventors: Patrick J. Crowley, Christopher J. Urch, Paul A. Worthington
  • Patent number: 4968847
    Abstract: There is disclosed a process for preparing polyhalogenated carbinols having formula: ##STR1## by reacting a compound having formula: ##STR2## with a system consisting of a compound having formula: ##STR3## and of a divalent metal or of a metal salt, in protic dipolar solvents, in which formulaeR=H, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkadienyl, phenyl, naphthyl, anthracyl group, a heterocyclic radical, optionally substituted;R'=H, a haloalkyl, --CN, --COOR" group with R" equal to H or to an alkyl group;X.sup.1 =Cl, Br; .dbd.X.sup.2 =F, Cl, Br;X.sup.3 =Cl, Br, CF.sub.3, CCl.sub.3 ; Y=Br or Cl when X.sup.1, X.sup.2 and X.sup.3 are different from Br.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: November 6, 1990
    Assignee: Istituto Guido Donegani S.p.A.
    Inventors: Pietro Massardo, Franco Bettarini, Paolo Piccardi, Franco Rama
  • Patent number: 4968848
    Abstract: A process for the preparation of perfluoroalkyl compounds which comprises reacting a perfluoroalkyl-trimethylsilane of the general formula (CH.sub.3).sub.3 Si-C.sub.n F.sub.2n+1 (I), wherein the group C.sub.n F.sub.2n+1 represents a perfluoroalkyl group having from 1 to 6 carbon atoms, with a carbonyl compound of the general formula F.sup.1 --CO--R.sup.2 (II), wherein R.sup.1 represents a hydrocarbon group or hydrogen and R.sup.2 represents a hydrocarbon group, a perfluoroalkyl group or a perfluoroaryl group, but wherein R.sup.1 and R.sup.2 together may also be part of an alicyclic ring system, in the presence of a salt-like fluoride--which is at least partially soluble in the reaction medium--as a catalyst to yield a silylether of the formula ##STR1## and isolating this compound or hydrolyzing it to yield an alcohol of the formula IV ##STR2## The invention also relates to pentafluoroethyl trimethylsilane (CH.sub.3).sub.3 Si--CF.sub.2 CF.sub.3 and a process for the preparation of this compound.
    Type: Grant
    Filed: February 21, 1989
    Date of Patent: November 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfred Kruse, Gunter Siegemund, Axel Schumann
  • Patent number: 4957986
    Abstract: Partially fluorinated polyesters are disclosed having increased biodegradability and water repellency. The incorporation of an ester group into the backbone of the partially fluorinated compound permits modification of the compound's physical properties.
    Type: Grant
    Filed: December 15, 1989
    Date of Patent: September 18, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harry N. Cripps
  • Patent number: 4950796
    Abstract: Novel benzonitriles, benzaldehydes and benzyl alcohols of the formula I ##STR1## where R.sup.1 is methyl or ethyl, R.sup.2 is alkyl, alkenyl, cycloalkyl, cycloalkenyl, bicycloalkyl, bicycloalkenyl, or C.sub.1 -C.sub.5 -alkyl-substituted cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, X is hydrogen, chlorine or fluorine and Z is --CN, CHO or ##STR2## where R.sup.3 is hydrogen, cyano, C.sub.2 -C.sub.4 -alkynyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkyl, with the proviso that R.sup.2 is not --CH.sub.2 --CH.dbd.CH--B when B is hydrogen, alkyl or alkenyl and at the same time R.sup.1 is methyl and Z is ##STR3## and with the proviso that R.sup.2 is not methyl or ethyl when R.sup.1 is methyl and at the same time Z is ##STR4## and furthermore with the proviso that R.sup.2 is not methyl when R.sup.1 is methyl or ethyl and at the same time Z is --CN or --CHO.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: August 21, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Wolf, Hans Theobald, Norbert Goetz
  • Patent number: 4950791
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: August 21, 1990
    Inventor: Herbert C. Brown
  • Patent number: 4943652
    Abstract: There is disclosed a process for asymmetrically reducing a carbonyl compound, which comprises reducing the carbonyl compound by the use of a reducing agent comprising (i) an optically active tartaric acid or ester thereof and (ii) a metal borohydride, thereby producing an optically active hydroxyl compound. The process can be used for the production of optically active hydroxyesters and alcohols from ketoesters and ketones. These products are useful for the production of medicaments and liquid crystals.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: July 24, 1990
    Assignee: Ajinomoto Co., Inc.
    Inventors: Masanobu Yatagai, Takashi Ohnuki
  • Patent number: 4940822
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, halo, halo-substituted alkyl, alkyl, cycloalkyl, aralkyl, aryl, heterocyclic, alkoxy, alkaryl, aryloxy, thioalkoxy, nitro, or N,N-dialkylamino are prepared by reacting 1-bromo-4-(trifluoromethyl)benzene with n-butyl lithium; reacting the product with a benzaldehyde of the formula: ##STR2## to produce a novel intermediate such as lithium 4-(trifluoromethyl)-.alpha.-]4-(trifluoromethyl)phenyl]benzenemethanol, and then reacting the lithium product with an acid or acid salt.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: July 10, 1990
    Assignee: Warner-Lambert Company
    Inventors: James G. Davidson, III, Brian S. Swierenga
  • Patent number: 4935560
    Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: June 19, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
  • Patent number: 4933511
    Abstract: An enantioselective process for the preparation of homoallyl alcohol enantiomer of formula II ##STR1## wherein: X.sup.1, X.sup.2 and X.sup.3 independently chosen from the group consisting of hydrogen, chlorine, bromine, fluorine, iodine, C.sub.1 to C.sub.6 alkyl, C.sub.1 and C.sub.6 haloalkyl, and haloaryl; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the group consisting of hydrogen, halogen, alkyl, alkenyl, alkynyl, benzyl, substituted benzyl, phenyl, substituted phenyl; or R.sup.3 and R.sup.4 is as hereinbefore defined and R.sup.1 and R.sup.2 form a carbocyclic or heterocyclic ring; which process comprises; reacting an aldehyde of formula III with an alkene or formula IV in the presence of an optically-active organometallic catalyst. ##STR2## Furthermore, the compound of formula II can be isomerized to the allylic alcohol of formula I with retention of optical purity.
    Type: Grant
    Filed: April 7, 1987
    Date of Patent: June 12, 1990
    Assignee: ICI Australia Limited
    Inventors: Matthew Gredley, Colin Wilshire
  • Patent number: 4929772
    Abstract: There is disclosed a process for preparing polyhalogenated carbinols having formula: ##STR1## by reacting a compound having formula: ##STR2## with a system consisting of a compound having formula: ##STR3## and of a divalent metal or of a metal salt, in protic dipolar solvents, in which formulaeR=H, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkadienyl, phenyl, naphthyl, anthracyl group, a heterocyclic radical, optionally substituted;R'=H, a haloalkyl, --CN, --COOR" group with R" equal to H or to an alkyl group;X.sup.1 =Cl, Br; =X.sub.2 =F, Cl, Br;X.sup.3 =Cl, Br, CF.sub.3, CCl.sub.3 ; Y=Br or Cl when X.sup.1, X.sup.2 and X.sup.3 are different from Br.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: May 29, 1990
    Assignee: Istituto Guido Donegani
    Inventors: Pietro Massardo, Franco Bettarini, Paolo Piccardi, Franco Rama
  • Patent number: 4918246
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resolution processes and novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: June 12, 1989
    Date of Patent: April 17, 1990
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4906792
    Abstract: Mono O-hydroxyalkylated derivatives of 1,1-dihydroperfluorinated alcohols are prepared by reaction the alcohols with alkylene carbonates. The O-hydroxyalkylated derivatives are useful non-ionic surfactants and emulsifiable compounds for fire extinguishing systems.
    Type: Grant
    Filed: November 4, 1988
    Date of Patent: March 6, 1990
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen
  • Patent number: 4902812
    Abstract: Provided herein is an optically active alcohol having a silyl group, stannyl group, or halogen atom at the .gamma.-position, selected from compounds represented by the general formula [I], ##STR1## the general formula [II], ##STR2## the general formula [III], ##STR3## and the general formula [IV], ##STR4## (where, R denotes a C.sub.1 -C.sub.10 substituted or unsubstituted alkyl group or substituted or unsubstituted phenyl group; A denotes a silyl group represented by ##STR5## a stannyl group represented by ##STR6## or a halogen atom. R.sup.1, R.sup.2, and R.sup.3 are substituted or unsubstituted C.sub.1 -C.sub.10 alkyl groups or substituted or unsubstituted phenyl group, which may be the same or different, provided that this does not apply in the case where A represents a stannyl group or halogen atom in the general formulas [III] and [IV].); a process for producing the same, and a process for resolving the optically active alcohol into isomers of high optical purity.
    Type: Grant
    Filed: July 30, 1987
    Date of Patent: February 20, 1990
    Assignee: Nissan Chemical Industries, Ltd.
    Inventor: Fumie Sato
  • Patent number: 4873375
    Abstract: A process for preparing a fluorine-substituted alicyclic diol comprising hydrogenating in the presence of a catalyst a fluorine-substituted aromatic diol represented by formula (I): ##STR1## wherein Ph represents a divalent organic group containing at least one aromatic group, to obtain the fluorine-substituted alicyclic diol represented by formula (II): ##STR2## wherein Ph(H) represents a divalent organic group containing at least one perhydroaromatic group.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: October 10, 1989
    Assignee: Daikin Industries, Ltd.
    Inventors: Motonobu Kubo, Yoshiki Shimizu
  • Patent number: 4871868
    Abstract: A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula ofA--X (I)wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula ofM--C.tbd.C--B (II)wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of--C.tbd.C--M (III)wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of ##STR1## wherein R.sup.1 and R.sup.2 independently represent a lower alkyl, and R.sup.3 represents a hydrogen or a lower alkyl.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: October 3, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yuzuru Saito, Kokichi Yoshida
  • Patent number: 4868202
    Abstract: Novel 3-phenylpyrrole derivatives of the formula I ##STR1## wherein R.sup.1 is cyano, trifluoromethyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, R.sup.2 is vinyl or a group --CH.sub.2 --CH.sub.2 --X, in which X is chlorine or bromine, or is cyano, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenylsulfonyl, 4-bromophenylsulfonyl or 4-methylphenylsulfonyl, R is halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl, and n is zero, one or two, have valuable microbicidal properties for controlling phytopathogenic plant pests, particularly phytopathogenic fungi.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: September 19, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Pierre Martin, Robert W. Lang
  • Patent number: 4868344
    Abstract: A process for producing the optically pure (+)- or (-) isomer of a phenyl- or substituted- phenylalkanolamine compounds having pharmacologic activity without the need for resoltuion processes ad novel intermediates useful in the process including optically pure haloalcohols are provided.
    Type: Grant
    Filed: March 30, 1988
    Date of Patent: September 19, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4855460
    Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Marc Tordeux, Claude Wakselman, Catherine Francese
  • Patent number: 4855292
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4855510
    Abstract: A compound having the formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is --CH.dbd.CH--X or --C.tbd.C--X where X is hydrogen or straight chain alkyl; R.sup.2 is halophenyl, Z is OR.sup.3 where R.sup.3 is H, alkyl, alkenyl or alkynyl; and acid addition salts and metal complexes thereof. These compounds have fungicidal and plant growth regulating properties. Intermediates for these compounds are also disclosed.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: August 8, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
  • Patent number: 4853414
    Abstract: Compounds of formula (I), useful as insecticides and knockdown agents: ##STR1## where Y is C.sub.1-6 alkoxy, Z is halo or C.sub.1-6 alkoxy; R is --(CH.sub.2).sub.p --(O).sub.m --R.sup.3 where m and p may be 0 or 1; R.sup.3 is C.sub.1-6 alkyl, phenyl or benzyl, or when m is 0, R.sup.3 is C.sub.1-6 alkenyl, haloalkenyl, alkynyl or haloalkynyl, and either (a) A and B are both C.sub.1-4 alkyl or (b) A is hydrogen and B is (R.sup.1)(R.sup.2)C.dbd.CH-- where R.sup.1 and R.sup.2 are selected from methyl, chloro, bromo, fluoro and trifluoromethyl.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 1, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, John Williams
  • Patent number: 4847438
    Abstract: A compound of formula I ##STR1## in which formula: D represents hydrogen or a cyano group;X represents halogen;A represents an alkyl group (typically a C.sub.1 -C.sub.6 alkyl group);n is 0 to 4;RCOO. represents a residue of an acid RCO.sub.2 H, which acid, or an ester-forming derivative of which acid, on reaction with .alpha.-cyano-3-phenoxybenzyl alcohol or an ester-forming derivative thereof, give rise to an .alpha.-cyano-3-phenoxybenzyl ester having pesticidal properties.
    Type: Grant
    Filed: April 13, 1987
    Date of Patent: July 11, 1989
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Richard L. Elliott
  • Patent number: 4840971
    Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4827052
    Abstract: The present invention provided optically active alcohols represented by the general formula: ##STR1## wherein R.sup.1 indicates an alkyl or alkyloxy group having a carbon number of 1-18, and A indicates a phenyl or a biphenyl group; or a phenyl or biphenyl group having a halogen atom or a cyano group. The alcohols are intermediates of optically active materials useful for components of liquid crystal materials for liquid crystal display elements having quick response.
    Type: Grant
    Filed: October 28, 1987
    Date of Patent: May 2, 1989
    Assignee: Chisso Corporation
    Inventors: Kouji Ohno, Shinichi Saito, Kazutoshi Miyazawa, Makoto Ushioda, Hiromichi Inoue, Naoyuki Yoshida
  • Patent number: 4827051
    Abstract: Pesticidal compounds have the formula: ##STR1## wherein D represents hydrogen or a cyano groupX represents chlorine or bromineA represents an alkyl groupn is 0 or an integer of 1-4 andRCOO 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: April 13, 1987
    Date of Patent: May 2, 1989
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman Janes, Richard L. Elliott
  • Patent number: 4822924
    Abstract: A process for producing 2,6-dichlorobenzyl alcohol, which comprises reacting 2,6-dichlorobenzyl chloride with an acetate-forming agent to form its acetate, followed by hydrolysis to obtain 2,6-dichlorobenzyl alcohol, wherein anhydrous sodium acetate is used as the acetate-forming agent, and a quaternary ammonium salt is added as a phase transfer catalyst during the acetate-forming reaction.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: April 18, 1989
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Ichiro Otsu, Sueo Kanno, Sinichi Sato, Tetsuya Kondo
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • Patent number: 4788177
    Abstract: It was found that ekylic ethers of 2,2,2-trichloro-1-phenylethanol with the general formula A ##STR1## are excellently usable as odoriferous substances, especially as components of perfume oils for cosmetic and technical consumer goods.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: November 29, 1988
    Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey
  • Patent number: 4783559
    Abstract: Disclosed is a process of reduction of aldehydes or ketones by means of reaction with alcohols, in the presence of a catalyst, to produce alcohols which correspond to said respective aldehyde or ketone. A solid of partially dehydrated one or more metal hydroxides whose metal is selected from the group consists of titanium, tin, ion, aluminium, cerium, and niobium is used as the catalyst. This process can be conducted either in a gas phase or in a liquid phase.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: November 8, 1988
    Assignee: Japan Tobacco Inc.
    Inventors: Hajime Matsushita, Kyoko Takahashi, Makoto Shibagaki
  • Patent number: 4767882
    Abstract: Tetrahydronaphthalene derivatives of the formula: ##STR1## wherein either one of R.sup.1 and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and the other is acetyl and R.sup.3 is hydrogen or methyl in a racemic or optically active form, which are useful as perfumes or intermediates for production of perfumes, are prepared from an R.sup.4 -benzene and pyrocine through the intermediary compounds of the formula: ##STR2## wherein R.sup.4 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy present at either one of 6- and 7-positions and A is hydrogen, carboxyl, C.sub.2 -C.sub.5 alkoxycarbonyl, halogen, methyl, hydroxymethyl or halomethyl.
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: August 30, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Gohfu Suzukamo, Yoji Sakito
  • Patent number: 4734516
    Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.
    Type: Grant
    Filed: March 19, 1986
    Date of Patent: March 29, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Robert W. Lang
  • Patent number: 4714790
    Abstract: The invention concerns a process for preparing 2-substituted-3,4,5,6-tetrafluorobenzyl alcohols by reaction of pentafluorobenzyl alcohol with a Grignard reagent under specified conditions. The products some of which are novel are useful as intermediates for insecticidal esters e.g. those with pyrethroid acids. A typical ester is 2-methyl-3,4,5,6-tetrafluorobenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate.
    Type: Grant
    Filed: August 18, 1986
    Date of Patent: December 22, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael J. Bushell
  • Patent number: 4705902
    Abstract: Process for preparing DDTr-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol (dicofol).
    Type: Grant
    Filed: May 15, 1986
    Date of Patent: November 10, 1987
    Assignee: Rohm and Haas Company
    Inventors: Richard W. Nichols, William J. Zabrodski, Abhijit Mitra
  • Patent number: 4701569
    Abstract: A process for the preparation of perfluoroalkylated alcohols and esters by bringing a carbonyl-containing derivative and a perfluoroalkyl iodide or bromide into contact with zinc, preferably in the presence of a polar aprotic solvent and/or a pyridine.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: October 20, 1987
    Assignee: Rhone-Poulenc Specialties Chimiques
    Inventors: Catherine Francese, Marc Tordeux, Claude Wakselman
  • Patent number: 4670443
    Abstract: Benzo(f)isoquinoline compounds, particularly, penta- and tetrahydrobenzo(f)isoquinoline dicarboxylic acid compounds, their preparation and their use as calcium entry blockers are disclosed.
    Type: Grant
    Filed: July 2, 1985
    Date of Patent: June 2, 1987
    Assignee: Merck & Co., Inc.
    Inventors: George D. Hartman, Brian T. Phillips
  • Patent number: 4645852
    Abstract: In an improved process of converting a 1,2-epoxy-2-phenylbutane or a 1,2-epoxy-2-phenylpentane to a 2-hydroxy-2-phenylbutylsulfonate, sulfamate, or halide, or the corresponding 2-hydroxy-2-phenylpentyl compound, respectively, by the reaction at about 40.degree. to 120.degree. C. in the presence of an organic solvent of the requisite epoxybutane or epoxypentane with a proton source and a nucleophile. The proton source can be a free strong acid such as a sulfonic, sulfamic acid, or hydrohalide acid, or the proton source can be derived from an equilibrium system comprising a free strong acid and weak base in equilibrium with the respective deprotonated strong acid and protonated weak base. The process is carried out in one step with reduction or avoidance of aldehyde formation by rearrangement of the epoxyalkane.
    Type: Grant
    Filed: September 16, 1985
    Date of Patent: February 24, 1987
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Richard C. Krauss