Halogen Containing Patents (Class 568/812)
  • Patent number: 4634466
    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 aklynyl; and acid addition salts and metal complexes thereof. The compounds are characterized by their fungicidal and plant growth activity.
    Type: Grant
    Filed: May 31, 1983
    Date of Patent: January 6, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
  • Patent number: 4616027
    Abstract: Compounds of the general formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from one to three substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and n is zero or an integer from 1 to 5; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing them.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: October 7, 1986
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4603227
    Abstract: This invention relates to a novel and improved process for preparing .alpha.-(trichloromethyl) benzyl alcohols, particularly, trichloromethyl-3-nitrobenzyl alcohol a key intermediate useful in the preparation of clorsulon (4-amino-6-(trichloroethenyl)-1,3-benzene-disulfonamide) via a base-catalyzed condensation reaction of benzaldehydes and chloroform.
    Type: Grant
    Filed: September 25, 1985
    Date of Patent: July 29, 1986
    Assignee: Merck & Co., Inc.
    Inventors: George G. Hazen, Jean M. Wyvratt
  • Patent number: 4598085
    Abstract: Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.
    Type: Grant
    Filed: January 21, 1982
    Date of Patent: July 1, 1986
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Heeres, Leo J. J. Backx, Joseph A. Mostmans
  • Patent number: 4593129
    Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4590308
    Abstract: Process for the monohalogenation of a benzene compound which has 2 or 3 CH.sub.2 OH substituents to obtain a product wherein one of the CH.sub.2 OH substituents is monohalogenated which comprises reacting an aqueous solution of the compound with hydrochloric or hydrobromic acid in the presence of a water immiscible organic solvent which is inert to the reactants, the partition coefficient of the compound in the aqueous/organic phases being greater, with respect to the aqueous phase, than the partition coefficient of the product. The novel compounds4-chloromethyl-2,3,5,6-tetrafluorobenzene methanol and4-bromomethyl-2,3,5,6-tetrafluorobenzene methanol are also disclosed.
    Type: Grant
    Filed: January 23, 1985
    Date of Patent: May 20, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventors: Alan T. Costello, David J. Milner
  • Patent number: 4578396
    Abstract: Hydroxyalkinyl-azolyl derivatives of the formula ##STR1## in which A is a nitrogen atom or the CH group,R is optionally substituted alkyl, cycloalkyl or phenyl,R.sup.1 is hydrogen, alkyl, alkenyl, alkinyl, or optionally substituted benzyl,R.sup.2 is hydrogen or methyl, andX is hydrogen, bromine or iodine,or addition products thereof with acids or metal salts exhibit fungicidal activity. Some intermediates therefor are also new.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: March 25, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Klaus Bockmann, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger, Hans Scheinpflug
  • Patent number: 4564476
    Abstract: Aryl fatty acid compounds of the formula (I) ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, and Y are as defined herein are novel and useful in the treatment of allergic and inflammatory disorders.
    Type: Grant
    Filed: October 29, 1984
    Date of Patent: January 14, 1986
    Assignee: McNeilab, Inc.
    Inventor: Chih Y. Ho
  • Patent number: 4560786
    Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.
    Type: Grant
    Filed: June 24, 1982
    Date of Patent: December 24, 1985
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
  • Patent number: 4557871
    Abstract: Novel styrene derivatives of the general formula ##STR1## wherein X is hydrogen or halogen, X.sup.1 is halogen, R is hydrogen or methyl, Y is hydroxymethyl, carboxyl, --COOR.sup.1 or --COR.sup.2 wherein R.sup.1 is prenyl, geranyl, farnesyl, cyclohexyl, phthalidyl, straight or branched chain alkyl having 1 to 6 carbon atoms, or said alkyl substituted with hydroxy, methoxy, pyridyl or alkanoyloxy having 2 to 16 carbon atoms, and R.sup.2 is amino, hydroxyamino mono-(or di-)alkylamino in which the alkyl moiety contains 1 or 2 carbon atoms, ethoxycarbonylmethylamino, carboxymethylamino, thiazolylamino, cyclohexylamino, pyridylamino, morpholino, N-methylpiperazino, phenylamino, phenylamino substituted with one or two of halogen, hydroxy, methyl, methoxy, trifluoromethyl or carboxyl at the phenyl ring, and the pharmaceutically acceptable salts thereof when Y is carboxyl are disclosed. These compounds exhibit high and long-lasting anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: December 10, 1985
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
  • Patent number: 4558148
    Abstract: There are described fluorinated allylic compounds as expressed by the following general formula ##STR1## wherein R.sub.f is a fluorinated aliphatic group and R is a group expressed by a general formula ##STR2## wherein R.sup.1 is an aliphatic or aromatic hydrocarbon group and R.sup.2 and R.sup.3 are the same group or different groups as selected among hydrogen atom, aliphatic and aromatic hydrocarbon groups, and heterocyclic groups. Further, a process of preparing fluorinated allylic compounds is described which includes a process step wherein a silane metal halide as expressed by a general formula(R.sup.1).sub.3 SiCH.sub.2 MX,wherein R.sup.1 is either an aliphatic or aromatic hydrocarbon group, M is an element that belongs to the group IIa, IIIb, or VIIb of the periodic table, and X is a halogen atom, is reacted with a fluorinated carboxylic acid ester as expressed by a general formulaR.sub.f COOR',wherein R.sub.
    Type: Grant
    Filed: July 30, 1984
    Date of Patent: December 10, 1985
    Assignee: Daikin Industries Ltd.
    Inventors: Nobuo Ishikawa, Tomoya Kitazume
  • Patent number: 4536347
    Abstract: Ruthenium-on-charcoal and ruthenium-on-carbon black catalysts, containing from 0.1 to 5% by weight of iron, for the preparation of olefinically unsaturated alcohols by selective hydrogenation of the corresponding .alpha., .beta.-unsaturated carbonyl compounds in the liquid phase are prepared by modifying the catalyst with iron only after it has been impregnated with the ruthenium compound, and reducing the catalyst with hydrogen at from 400.degree. to 600.degree. C., with thorough mixing.The catalysts according to the invention are particularly useful for improving the industrially difficult hydrogenation of citral to give the soughtafter fragrances geraniol and nerol.
    Type: Grant
    Filed: March 19, 1984
    Date of Patent: August 20, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Horner, Matthias Irgang
  • Patent number: 4532020
    Abstract: A process for preparing a .beta.-(fluoroalkyl or fluoroalkenyl)-.beta.-hydroxyalkyne represented by the formula ##STR1## wherein R.sub.f represents a fluoroalkyl or fluoroalkenyl group and R represents an aliphatic or aromatic group, comprising reacting an alkyne represented by the formulaR--C.tbd.CH (II)wherein R is the same as defined above with a fluorine containing aldehyde represented by the formulaR.sub.f CHO (III)wherein R.sub.f is the same as defined above in the presence of catalyst under ultrasonic irradiation.A process for preparing an .alpha.-(fluoroalkyl or fluoroalkenyl)allyl alcohol represented by the formula ##STR2## wherein R.sub.f represents a fluoroalkyl or fluoroalkenyl group, R represents an aliphatic or aromatic group and R' represents a hydrogen atom or an aliphatic group, comprising (1) reacting a .beta.-(fluoroalkyl or fluoroalkenyl)-.beta.-hydroxyalkyne represented by the formula ##STR3## wherein R.sub.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: July 30, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Nobuo Ishikawa, Tomoya Kitazume
  • Patent number: 4518415
    Abstract: Compounds useful as plant growth regulators and fungicides and having the formula ##STR1## and stereoisomers thereof, wherein W is --CH.dbd. or .dbd.N--; Q is optionally substituted aryl, especially optionally substituted phenyl, or optionally substituted aralkyl or alkyl; R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are H, optionally substituted alkyl, cycloalkyl, aralkyl or phenyl; R.sup.7 and R.sup.8 are H, alkyl or optionally substituted phenyl; and acid addition salts and metal complexes thereof, and processes and intermediates for their preparation.
    Type: Grant
    Filed: January 21, 1983
    Date of Patent: May 21, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony F. Marchington, Timothy Lewis, John M. Clough, Paul A. Worthington, John Dalziel
  • Patent number: 4510338
    Abstract: The invention relates to new resorcin derivatives of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 3 carbon atoms or alkoxy having from one to 3 carbon atoms.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredient are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 9, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4508926
    Abstract: The invention relates to new 4-hydroxy-benzhydrols of the formula (I) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen, halogen, trihalomethyl, alkyl having from one to 4 carbon atoms or alkoxy having from one to 4 carbon atoms, with the proviso that if R.sub.1 is hydrogen, R.sub.2 is other than hydrogen or a 3-trifluoromethyl group, or if R.sub.1 is a 2-methyl group, R.sub.2 is other than a 5-methyl group.According to another aspect of the invention there are provided processes for the preparation of these compounds.The compounds of the formula (I) are pharmacologically active. In particular, they are suitable for the treatment of acute ethanolic intoxication. Pharmaceutical compositions containing them as active ingredients are also within the scope of the invention.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: April 2, 1985
    Assignee: Richter Gedeon Vegyeszeti Gyar Rt.
    Inventors: Edit Toth, Jozsef Torley, Gyorgy Fekete, Laszlo Szporny, Laszlo Vereczkey, Eva Palosi, Imre Klebovich, Pal Vittay, Sandor Gorog, Istvan Hajdu
  • Patent number: 4503062
    Abstract: This invention relates to novel alicyclic alcohol compounds of the formula ##STR1## wherein Az is imidazole or 1,2,4-triazole, R.sup.6 is optionally substituted phenyl and A is an alicyclic ring optionally benzo-fused, which compounds possess pharmaceutical, veterinary, agricultural and horticultural antifungal properties; together with a process for their manufacture, compositions containing them, and a method of combatting plant fungal diseases.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: March 5, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael B. Gravestock
  • Patent number: 4496777
    Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a water soluble salt of an amphoteric metal; in particular, a salt of tin, aluminum, zinc, zirconium, magnesium, or titanium, which provides a pH of from 2 to 5 under reaction conditions.
    Type: Grant
    Filed: November 9, 1983
    Date of Patent: January 29, 1985
    Assignee: The Lummus Company
    Inventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
  • Patent number: 4486355
    Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: December 4, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Philip D. Bentley, Nazim Punja
  • Patent number: 4486612
    Abstract: Tertiary carbinols are prepared by reacting an appropriate tertiary halide with water in the presence of a catalytic amount of an emulsifying agent. .alpha.-Methyl-.alpha.-(2,2,2-trichloroethyl)benzyl alcohol is prepared with a high rate of conversion and a low incidence of the formation of an olefin by-product. .alpha.-Methyl-.alpha.-(2,2,2-trichloroethyl)benzyl alcohol is useful as a nitrification inhibitor and as an intermediate in the preparation of structurally related nitrification inhibitors.
    Type: Grant
    Filed: March 23, 1983
    Date of Patent: December 4, 1984
    Assignee: The Dow Chemical Company
    Inventor: R. Garth Pews
  • Patent number: 4479020
    Abstract: Production of halohydrins; in particular, chlorohydrins by reaction of tertiary alkyl hypohalite and olefinically unsaturated compound in the presence of water and a metal selected from Group II-A, II-B, III-A, III-B, IV-A, IV-B, or V-A of the Periodic Table. The use of such metals improves the production of halohydrin.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: October 23, 1984
    Assignee: The Lummus Company
    Inventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
  • Patent number: 4474993
    Abstract: The disclosure relates to a continuous method and an apparatus for the hydrolysis of .alpha.-chlorinated toluene compounds, preferably benzyl chloride. The hydrolysis, which takes place in a hydrolysis zone, is characterized by being conducted in countercurrent between the aqueous phase containing the hydrolyzing agent and the organic phase containing the .alpha.-chlorinated toluene compound and an inert organic solvent, such as toluene. After the hydrolysis, the organic phase is washed with water in a washing zone, while the aqueous phase is extracted with inert solvent in an extraction zone. The resulting product of hydrolysis, preferably benzyl alcohol, is thereafter separated from the organic phase by distillation, suitably in two stages, by means of two distillation columns connected in series.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: October 2, 1984
    Inventors: Goran L. F. Hag, Risto K. Rantala
  • Patent number: 4469902
    Abstract: Novel 1-iodoprop-1-yn-3-ols of the formula ##STR1## in which R.sup.1 represents optionally substituted aryl andR.sup.2 represents alkyl or cycloalkyl, which may be used as plant protection agents, especially as fungicides, are obtained when 1-iodoprop-1-yn-3-ols are reacted with iodine in the presence of a basic compound.
    Type: Grant
    Filed: May 14, 1982
    Date of Patent: September 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4468527
    Abstract: A fluoroaliphatic radical- and aliphatic chlorine-containing alcohol containing more than 25 weight percent carbon-bonded fluorine in the form of fluoroaliphatic radicals and at least one aliphatic chlorine, an ester of said alcohol and a carboxycylic acid being useful in the treatment of carpet.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: August 28, 1984
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Kalyanji U. Patel
  • Patent number: 4467102
    Abstract: An optically active propargyl alcohol derivative of the formula (I) ##STR1## wherein X=phenyl or thienyl and R=lower alkyl, halogenated methyl, phenyl or substituted phenyl having at least one lower alkyl radical and or halogen atom, is prepared by contacting a racemic modification of l- and d-isomers of the formula (I) with l-brucine in an organic solvent, by separating the resultant deposited diastereomer from a solution containing the resultant other diastereomer in the organic solvent, by decomposing each diastereomer with an aqueous mineral acid solution in the presence of an organic solvent capable of dissolving the corresponding optically active isomer dissociated from the diastereomer and incompatible with water so as to allow the optically active isomer to be dissolved in the water-incompatible organic solvent, and by recovering the optically active isomer from the solution thereof.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 21, 1984
    Assignee: Ube Industries, Ltd.
    Inventors: Fumio Toda, Koichi Tanaka
  • Patent number: 4443625
    Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein X is H or ##STR2## R is H or C.sub.1 -C.sub.8 alkyl; R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.
    Type: Grant
    Filed: May 14, 1981
    Date of Patent: April 17, 1984
    Assignee: The Dow Chemical Co.
    Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
  • Patent number: 4435605
    Abstract: The invention is a process for the preparation of a 2-phenylethyl alcohol which comprises contacting an aromatic aldehyde with carbon monoxide and hydrogen in a solvent comprising an oxygenated polar hydrocarbon and water, in the presence of a catalytic amount of a catalyst comprising a cobalt compound, a ruthenium salt and an iodine salt, at elevated temperatures and a pressure of between 600 and 45,000 psi.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: March 6, 1984
    Assignee: The Dow Chemical Company
    Inventors: Susan B. Butts, George E. Hartwell
  • Patent number: 4429153
    Abstract: This invention relates to novel cyclopropane derivatives useful as insecticides, to processes for their preparation, to compositions comprising them and to methods of combatting insect and similar invertebrate pests using them.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: January 31, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • Patent number: 4416682
    Abstract: Fungicidal compounds of the formula: ##STR1## wherein R.sup.1 is an optionally substituted-alkyl, -cycloalkyl, -aryl or -aralkyl group, Y.sup.1 and Y.sup.2 are .dbd.CH-- or .dbd.N--; and salts, metal complexes, ethers and esters thereof.
    Type: Grant
    Filed: June 2, 1981
    Date of Patent: November 22, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Paul A. Worthington
  • Patent number: 4414210
    Abstract: This invention relates to 2-hydroxyarylethyl-1,2,4-triazoles, their acid addition salts and metal salt complexes. This invention also relates to the method of preparation and use of these compounds. These compounds and salts thereof are highly active broad-spectrum systemic fungicides effective in controlling phytopathogenic fungi such as barley net blotch (Helminthosporium teres), grey mold (Botrytis fabae), bean powdery mildew (Erysiphe polygoni), grape downy mildew (Plasmopora viticola), rice blast (Piricularia oryzae), tomato late blight (Phytophthora infestans) and wheat stem rust (Puccinia graminis f. sp. tritici race 158-2).
    Type: Grant
    Filed: May 19, 1981
    Date of Patent: November 8, 1983
    Assignee: Rohm and Haas Company
    Inventors: George A. Miller, Hak-Foon Chan
  • Patent number: 4405640
    Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: September 20, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • Patent number: 4404216
    Abstract: 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol and its pharmaceutically acceptable acid addition salts are disclosed. This particular bis-triazole derivative and its aforesaid salts are useful for treating fungal infections in animals, including humans. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: September 13, 1983
    Assignee: Pfizer Inc.
    Inventor: Kenneth Richardson
  • Patent number: 4387253
    Abstract: 2,4-Dichlorobenzyl alcohol is obtained in high purity and in high yield by reacting 2,4-dichlorobenzyl chloride in a two stage reaction with a water soluble salt of an organic acid in the presence of a phase transfer catalyst to give the 2,4-dichlorobenzyl ester of the organic acid which is subsequently hydrolysed with a strong base.
    Type: Grant
    Filed: August 12, 1981
    Date of Patent: June 7, 1983
    Assignee: The Boots Company Limited
    Inventor: Christopher J. Gower
  • Patent number: 4386035
    Abstract: A process for the preparation of 3-bromo-4-fluoro-benzyl alcohol of the formula ##STR1## comprising reacting 3-bromo-4-fluoro-benzoic acid or a derivative thereof of the formula ##STR2## in which R is a hydrogen atom, an alkyl radical or an alkoxycarbonyl radical,with a complex hydride of the formulaM(M'H.sub.4)in whichM is lithium, sodium or potassium, andM' is boron or aluminum,at a temperature between about -20.degree. and +150.degree. C. When R is alkoxycarbonyl the starting material can be produced by reacting the corresponding free acid with a chloroformic acid ester. Compounds wherein R is alkyl or alkoxycarbonyl are new. The end product is a known intermediate for insecticides.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: May 31, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Rainer Fuchs, Erich Klauke
  • Patent number: 4385070
    Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: May 24, 1983
    Assignee: Imperial Chemical Industries Limited
    Inventors: Philip D. Bentley, Nazim Punja
  • Patent number: 4375548
    Abstract: Silylated trichloromethyl carbinol compounds are prepared by contacting aldehydes and ketones with silylated trichloroacetates at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: March 1, 1983
    Assignee: The Dow Chemical Company
    Inventors: Pen-Chung Wang, James M. Renga
  • Patent number: 4335136
    Abstract: 4,5-Diaryl-.alpha.-(polyfluoroalkyl)-1H-pyrrole-2-methanamines such as 4,5-bis(4-fluorophenyl)-.alpha..alpha.-bis-(trifluoromethyl)-1H-pyrrole-2- methanamine, useful in treatment of inflammation.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: June 15, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Saul C. Cherkofsky
  • Patent number: 4326087
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: April 20, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
  • Patent number: 4317918
    Abstract: An alcohol is produced in a high selectivity with a good yield from the corresponding carboxylic acid by reducing the latter with hydrogen in the presence of a rhenium catalyst in the coexistence of an organic base. An arylacetic acid, which is included in the starting carboxylic acid, can be produced in an excellent yield from the corresponding aryl aldehyde by reacting the latter with carbon monoxide and water in the presence of rhodium or its compound and hydrogen iodide.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: March 2, 1982
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
  • Patent number: 4302612
    Abstract: This invention is concerned with the synthesis of perfluorodialdehydes from the corresponding perfluorodiesters and with intermediates useful in the preparation of the perfluorodialdehydes.
    Type: Grant
    Filed: January 26, 1978
    Date of Patent: November 24, 1981
    Assignee: Polaroid Corporation
    Inventors: David H. Evans, Richard B. Greenwald
  • Patent number: 4301088
    Abstract: A method for preparing benzyl alcohols or substituted benzyl alcohols is disclosed by decarbonylation of formic acid esters of benzyl alcohols or ring substituted benzyl alcohols, the decarbonylation being carried out in the presence of a catalyst.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: November 17, 1981
    Assignee: Dynamit Nobel AG
    Inventor: Gunther Bernhardt
  • Patent number: 4299995
    Abstract: 9-substituted, 4- or 6-fluorine substituted retinoic acid derivatives useful as antitumor agents and in the treatment of acne as well as a method for their manufacture are disclosed. Substituents at the 9-position include substituted phenyl, thienyl and furyl groups.
    Type: Grant
    Filed: May 13, 1980
    Date of Patent: November 10, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ka-Kong Chan, Beverly A. Pawson
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4275250
    Abstract: 2,2-Dimethyl-3-vinyl-cyclopropane carboxylic acid esters of halogenated benzyl alcohols of the formula ##STR1## in which each R independently represents F, Cl, Br or CH.sub.3 andm and n each represent 0, 1, 2, 3, 4 or 5 subject to the sum of m+n being not more than 5,with the provisos that(i) when each R represents F or Br then m and n cannot both be 0,(ii) when each R represents Cl, then m represents 0, 1, 2, 3 or 5 and n represents 1, 2, 3, 4 or 5, and(iii) when each R represents CH.sub.3, then m represents 0 and n represents 5,which possess arthropodicidal properties.
    Type: Grant
    Filed: June 6, 1979
    Date of Patent: June 23, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Erich Klauke, Albrecht Marhold
  • Patent number: 4273947
    Abstract: A process is described for the heterogeneous hydrogenation of fluorine-containing alkyl, cycloalkyl, and benzene carboxylic acids to the corresponding primary alcohols. The hydrogenation can be carried out in the liquid or vapor phase in the presence of a solid rhodium or iridium catalyst, employed as the metal, metallic oxide, or mixture thereof. In the liquid phase, the hydrogenation can be carried out batchwise under mild conditions of temperature and pressure, preferably at about 50.degree.-150.degree. C. and about 5-15 atmospheres, in an atmosphere containing hydrogen gas. A preferred embodiment is the hydrogenation of trifluoroacetic acid in the liquid phase to 2,2,2-trifluoroethanol, said alcohol being useful as an intermediate in the synthesis of the anesthetic, isoflurane, CF.sub.3 CHClOCHF.sub.2.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: June 16, 1981
    Assignee: Allied Chemical Corporation
    Inventor: Miroslav Novotny
  • Patent number: 4271319
    Abstract: The present invention relates to a novel organic compound, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone. This compound may be produced by:(a) condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b) epoxidation of the substituted chalcone to produce the corresponding epoxide, and(c) converting the epoxide to a chlorohydrin, phenyl beta-chloro-alpha-hydroxy-beta-(3-trifluoromethylphenyl)ethyl ketone.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: June 2, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4223172
    Abstract: Bromoarylacetylenes such as m-bromophenylacetylene and certain precursors to such bromoarylacetylene are prepared by reacting an aryldibromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence. The bromoarylacetylenes can be reacted with a substituted terminal acetylene compound as defined using the same catalyst system as defined to produce the corresponding aryldihydroxy substituted acetylenes. Certain bromophenylhydroxy substituted acetylenes are claimed as new compositions.
    Type: Grant
    Filed: December 7, 1978
    Date of Patent: September 16, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Edward T. Sabourin, Charles M. Selwitz
  • Patent number: 4219683
    Abstract: Olefinically unsaturated compounds, such as nitriles, alcohols, esters, ethers and the like are isomerized to other unsaturated compounds in the presence of a palladium-thorium oxide catalyst and hydrogen.
    Type: Grant
    Filed: September 25, 1978
    Date of Patent: August 26, 1980
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • Patent number: 4210610
    Abstract: Chloroarylacetylenes such as m-chlorophenylacetylene and certain precursors to such chloroarylacetylene are prepared by reacting a chloroarylbromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence.
    Type: Grant
    Filed: December 7, 1978
    Date of Patent: July 1, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Edward T. Sabourin, Charles M. Selwitz