Halogen Containing Patents (Class 568/812)
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Patent number: 5118881Abstract: 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: GrantFiled: November 8, 1990Date of Patent: June 2, 1992Assignee: Agan Chemical Manufacturers, Ltd.Inventors: Bernard Vaisbuch, Benjamin Shifman, Michael Pikarski
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Patent number: 5116981Abstract: 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: GrantFiled: June 29, 1989Date of Patent: May 26, 1992Assignee: The Upjohn CompanyInventor: Joel Morris
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Patent number: 5081319Abstract: 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: GrantFiled: July 18, 1990Date of Patent: January 14, 1992Assignee: Sociedad Espanola de Desarrollos Quimicos S.A.Inventors: Jaime Palencia Adrubau, Jaume Castella Sola
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Patent number: 5081317Abstract: 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: GrantFiled: December 7, 1990Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Reiner Kober, Heinz Isak, Rainer Seele
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Patent number: 5075512Abstract: 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: GrantFiled: November 27, 1990Date of Patent: December 24, 1991Assignee: Sociedad Espanola de Desarrollos Quimicos S.A.Inventors: Jaime Palencia Adrubau, Jaume Castella Sola
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Patent number: 5072037Abstract: 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: GrantFiled: December 21, 1990Date of Patent: December 10, 1991Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Peter Lappe, Helmut Springer
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Patent number: 5066815Abstract: 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: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
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Patent number: 5057626Abstract: A process for the synthesis of alpha,alpha-difluoroketones from alpha,alpha-difluoroacylsilanes and intermediates therefor.Type: GrantFiled: October 1, 1990Date of Patent: October 15, 1991Assignee: Pfizer Inc.Inventor: Peter A. McCarthy
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Patent number: 5017730Abstract: 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: GrantFiled: March 12, 1990Date of Patent: May 21, 1991Assignee: Central Glass Company, LimitedInventors: Yoshihiko Gotoh, Toshikazu Kawai, Junji Negishi
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Patent number: 4990693Abstract: 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: GrantFiled: January 16, 1990Date of Patent: February 5, 1991Assignee: 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
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Patent number: 4990677Abstract: 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: GrantFiled: February 12, 1990Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
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Patent number: 4990689Abstract: 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: GrantFiled: June 20, 1989Date of Patent: February 5, 1991Assignee: Central Glass Company, LimitedInventors: Masamichi Maruta, Takayuki Nishimiya
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Patent number: 4987236Abstract: 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: GrantFiled: November 17, 1989Date of Patent: January 22, 1991Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 4973767Abstract: 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: GrantFiled: December 12, 1988Date of Patent: November 27, 1990Assignee: Sandoz Ltd.Inventors: Patrick J. Crowley, Christopher J. Urch, Paul A. Worthington
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Patent number: 4968847Abstract: 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: GrantFiled: March 19, 1990Date of Patent: November 6, 1990Assignee: Istituto Guido Donegani S.p.A.Inventors: Pietro Massardo, Franco Bettarini, Paolo Piccardi, Franco Rama
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Patent number: 4968848Abstract: 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: GrantFiled: February 21, 1989Date of Patent: November 6, 1990Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Axel Schumann
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Patent number: 4957986Abstract: 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: GrantFiled: December 15, 1989Date of Patent: September 18, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventor: Harry N. Cripps
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Patent number: 4950796Abstract: 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: GrantFiled: June 14, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Bernd Wolf, Hans Theobald, Norbert Goetz
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Patent number: 4950791Abstract: 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: GrantFiled: June 12, 1989Date of Patent: August 21, 1990Inventor: Herbert C. Brown
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Patent number: 4943652Abstract: 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: GrantFiled: November 14, 1988Date of Patent: July 24, 1990Assignee: Ajinomoto Co., Inc.Inventors: Masanobu Yatagai, Takashi Ohnuki
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Patent number: 4940822Abstract: 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: GrantFiled: November 4, 1988Date of Patent: July 10, 1990Assignee: Warner-Lambert CompanyInventors: James G. Davidson, III, Brian S. Swierenga
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Patent number: 4935560Abstract: Novel styryl-tetrahydromaphthalene and indane derivatives useful for treating neoplasms and dermatoses.Type: GrantFiled: January 16, 1990Date of Patent: June 19, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Michael Klaus, Peter Loeliger, Peter Mohr, Ekkehard Weiss
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Patent number: 4933511Abstract: 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: GrantFiled: April 7, 1987Date of Patent: June 12, 1990Assignee: ICI Australia LimitedInventors: Matthew Gredley, Colin Wilshire
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Patent number: 4929772Abstract: 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: GrantFiled: March 9, 1989Date of Patent: May 29, 1990Assignee: Istituto Guido DoneganiInventors: Pietro Massardo, Franco Bettarini, Paolo Piccardi, Franco Rama
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Patent number: 4918246Abstract: 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: GrantFiled: June 12, 1989Date of Patent: April 17, 1990Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 4906792Abstract: 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: GrantFiled: November 4, 1988Date of Patent: March 6, 1990Assignee: Minnesota Mining and Manufacturing CompanyInventors: Steven M. Heilmann, Larry R. Krepski, Dean M. Moren, Jerald K. Rasmussen
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Patent number: 4902812Abstract: 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: GrantFiled: July 30, 1987Date of Patent: February 20, 1990Assignee: Nissan Chemical Industries, Ltd.Inventor: Fumie Sato
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Patent number: 4873375Abstract: 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: GrantFiled: April 11, 1988Date of Patent: October 10, 1989Assignee: Daikin Industries, Ltd.Inventors: Motonobu Kubo, Yoshiki Shimizu
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Patent number: 4871868Abstract: 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: GrantFiled: March 3, 1988Date of Patent: October 3, 1989Assignee: Takeda Chemical Industries, Ltd.Inventors: Yuzuru Saito, Kokichi Yoshida
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Patent number: 4868202Abstract: 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: GrantFiled: December 22, 1987Date of Patent: September 19, 1989Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Robert W. Lang
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Patent number: 4868344Abstract: 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: GrantFiled: March 30, 1988Date of Patent: September 19, 1989Assignee: Aldrich-Boranes, Inc.Inventor: Herbert C. Brown
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Patent number: 4855460Abstract: 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: GrantFiled: July 11, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Marc Tordeux, Claude Wakselman, Catherine Francese
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Patent number: 4855292Abstract: 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: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4855510Abstract: 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: GrantFiled: November 14, 1986Date of Patent: August 8, 1989Assignee: Imperial Chemical Industries PLCInventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
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Patent number: 4853414Abstract: 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: GrantFiled: October 30, 1987Date of Patent: August 1, 1989Assignee: Imperial Chemical Industries PLCInventors: Michael J. Robson, John Williams
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Patent number: 4847438Abstract: 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: GrantFiled: April 13, 1987Date of Patent: July 11, 1989Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Richard L. Elliott
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Patent number: 4840971Abstract: 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: GrantFiled: April 2, 1987Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
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Patent number: 4827052Abstract: 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: GrantFiled: October 28, 1987Date of Patent: May 2, 1989Assignee: Chisso CorporationInventors: Kouji Ohno, Shinichi Saito, Kazutoshi Miyazawa, Makoto Ushioda, Hiromichi Inoue, Naoyuki Yoshida
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Patent number: 4827051Abstract: 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: GrantFiled: April 13, 1987Date of Patent: May 2, 1989Assignee: National Research Development CorporationInventors: Michael Elliott, Norman Janes, Richard L. Elliott
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Patent number: 4822924Abstract: 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: GrantFiled: December 23, 1987Date of Patent: April 18, 1989Assignee: Hodogaya Chemical Co., Ltd.Inventors: Ichiro Otsu, Sueo Kanno, Sinichi Sato, Tetsuya Kondo
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Patent number: 4791139Abstract: 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: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4788177Abstract: 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: GrantFiled: July 27, 1987Date of Patent: November 29, 1988Inventors: Ernst-Joachim Brunke, Claus-Hermann Kappey
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Patent number: 4783559Abstract: 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: GrantFiled: March 25, 1987Date of Patent: November 8, 1988Assignee: Japan Tobacco Inc.Inventors: Hajime Matsushita, Kyoko Takahashi, Makoto Shibagaki
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Patent number: 4767882Abstract: 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: GrantFiled: August 26, 1986Date of Patent: August 30, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Gohfu Suzukamo, Yoji Sakito
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Patent number: 4734516Abstract: 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: GrantFiled: March 19, 1986Date of Patent: March 29, 1988Assignee: Ciba-Geigy CorporationInventor: Robert W. Lang
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Patent number: 4714790Abstract: 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: GrantFiled: August 18, 1986Date of Patent: December 22, 1987Assignee: Imperial Chemical Industries PLCInventor: Michael J. Bushell
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Patent number: 4705902Abstract: Process for preparing DDTr-free 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol (dicofol).Type: GrantFiled: May 15, 1986Date of Patent: November 10, 1987Assignee: Rohm and Haas CompanyInventors: Richard W. Nichols, William J. Zabrodski, Abhijit Mitra
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Patent number: 4701569Abstract: 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: GrantFiled: May 21, 1986Date of Patent: October 20, 1987Assignee: Rhone-Poulenc Specialties ChimiquesInventors: Catherine Francese, Marc Tordeux, Claude Wakselman
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Patent number: 4670443Abstract: 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: GrantFiled: July 2, 1985Date of Patent: June 2, 1987Assignee: Merck & Co., Inc.Inventors: George D. Hartman, Brian T. Phillips
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Patent number: 4645852Abstract: 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: GrantFiled: September 16, 1985Date of Patent: February 24, 1987Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Richard C. Krauss