Halogen Containing Patents (Class 568/812)
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Patent number: 4634466Abstract: 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: GrantFiled: May 31, 1983Date of Patent: January 6, 1987Assignee: Imperial Chemical Industries PLCInventors: Robert A. Noon, Patrick J. Crowley, Diana M. Worthington
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Patent number: 4616027Abstract: 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: GrantFiled: July 25, 1983Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4603227Abstract: 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: GrantFiled: September 25, 1985Date of Patent: July 29, 1986Assignee: Merck & Co., Inc.Inventors: George G. Hazen, Jean M. Wyvratt
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Patent number: 4598085Abstract: 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: GrantFiled: January 21, 1982Date of Patent: July 1, 1986Assignee: Janssen Pharmaceutica N.V.Inventors: Jan Heeres, Leo J. J. Backx, Joseph A. Mostmans
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Patent number: 4593129Abstract: 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: GrantFiled: April 18, 1984Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
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Patent number: 4590308Abstract: 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: GrantFiled: January 23, 1985Date of Patent: May 20, 1986Assignee: Imperial Chemical Industries PLCInventors: Alan T. Costello, David J. Milner
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Patent number: 4578396Abstract: 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: GrantFiled: May 27, 1983Date of Patent: March 25, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Klaus Bockmann, Karl H. Buchel, Wilhelm Brandes, Paul-Ernst Frohberger, Hans Scheinpflug
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Patent number: 4564476Abstract: 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: GrantFiled: October 29, 1984Date of Patent: January 14, 1986Assignee: McNeilab, Inc.Inventor: Chih Y. Ho
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Patent number: 4560786Abstract: .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: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4557871Abstract: 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: GrantFiled: May 14, 1984Date of Patent: December 10, 1985Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
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Patent number: 4558148Abstract: 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: GrantFiled: July 30, 1984Date of Patent: December 10, 1985Assignee: Daikin Industries Ltd.Inventors: Nobuo Ishikawa, Tomoya Kitazume
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Patent number: 4536347Abstract: 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: GrantFiled: March 19, 1984Date of Patent: August 20, 1985Assignee: BASF AktiengesellschaftInventors: Michael Horner, Matthias Irgang
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Patent number: 4532020Abstract: 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: GrantFiled: March 7, 1984Date of Patent: July 30, 1985Assignee: Daikin Kogyo Co., Ltd.Inventors: Nobuo Ishikawa, Tomoya Kitazume
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Patent number: 4518415Abstract: 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: GrantFiled: January 21, 1983Date of Patent: May 21, 1985Assignee: Imperial Chemical Industries PLCInventors: Anthony F. Marchington, Timothy Lewis, John M. Clough, Paul A. Worthington, John Dalziel
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Patent number: 4510338Abstract: 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: GrantFiled: December 27, 1983Date of Patent: April 9, 1985Assignee: 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
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4-Hydroxy-benzhydrols, process for their preparation and pharmaceutical compositions containing them
Patent number: 4508926Abstract: 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: GrantFiled: December 27, 1983Date of Patent: April 2, 1985Assignee: 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: 4503062Abstract: 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: GrantFiled: March 28, 1983Date of Patent: March 5, 1985Assignee: Imperial Chemical Industries PLCInventor: Michael B. Gravestock
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Patent number: 4496777Abstract: 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: GrantFiled: November 9, 1983Date of Patent: January 29, 1985Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4486355Abstract: 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: GrantFiled: April 25, 1983Date of Patent: December 4, 1984Assignee: Imperial Chemical Industries PLCInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4486612Abstract: 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: GrantFiled: March 23, 1983Date of Patent: December 4, 1984Assignee: The Dow Chemical CompanyInventor: R. Garth Pews
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Patent number: 4479020Abstract: 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: GrantFiled: November 12, 1982Date of Patent: October 23, 1984Assignee: The Lummus CompanyInventors: George D. Suciu, Joon T. Kwon, Atef M. Shaban
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Patent number: 4474993Abstract: 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: GrantFiled: April 28, 1982Date of Patent: October 2, 1984Inventors: Goran L. F. Hag, Risto K. Rantala
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Patent number: 4469902Abstract: 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: GrantFiled: May 14, 1982Date of Patent: September 4, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Jager, Wilhelm Brandes, Paul-Ernst Frohberger
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Patent number: 4468527Abstract: 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: GrantFiled: March 15, 1982Date of Patent: August 28, 1984Assignee: Minnesota Mining and Manufacturing CompanyInventor: Kalyanji U. Patel
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Patent number: 4467102Abstract: 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: GrantFiled: November 21, 1983Date of Patent: August 21, 1984Assignee: Ube Industries, Ltd.Inventors: Fumio Toda, Koichi Tanaka
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Patent number: 4443625Abstract: 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: GrantFiled: May 14, 1981Date of Patent: April 17, 1984Assignee: The Dow Chemical Co.Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
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Patent number: 4435605Abstract: 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: GrantFiled: August 27, 1982Date of Patent: March 6, 1984Assignee: The Dow Chemical CompanyInventors: Susan B. Butts, George E. Hartwell
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Patent number: 4429153Abstract: 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: GrantFiled: January 15, 1982Date of Patent: January 31, 1984Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4416682Abstract: 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: GrantFiled: June 2, 1981Date of Patent: November 22, 1983Assignee: Imperial Chemical Industries PLCInventor: Paul A. Worthington
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Patent number: 4414210Abstract: 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: GrantFiled: May 19, 1981Date of Patent: November 8, 1983Assignee: Rohm and Haas CompanyInventors: George A. Miller, Hak-Foon Chan
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Patent number: 4405640Abstract: 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: GrantFiled: December 1, 1980Date of Patent: September 20, 1983Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4404216Abstract: 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: GrantFiled: June 1, 1982Date of Patent: September 13, 1983Assignee: Pfizer Inc.Inventor: Kenneth Richardson
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Patent number: 4387253Abstract: 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: GrantFiled: August 12, 1981Date of Patent: June 7, 1983Assignee: The Boots Company LimitedInventor: Christopher J. Gower
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Patent number: 4386035Abstract: 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: GrantFiled: September 14, 1981Date of Patent: May 31, 1983Assignee: Bayer AktiengesellschaftInventors: Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Rainer Fuchs, Erich Klauke
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Patent number: 4385070Abstract: 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: GrantFiled: January 28, 1980Date of Patent: May 24, 1983Assignee: Imperial Chemical Industries LimitedInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4375548Abstract: Silylated trichloromethyl carbinol compounds are prepared by contacting aldehydes and ketones with silylated trichloroacetates at elevated temperatures in the presence of an initiator.Type: GrantFiled: December 17, 1981Date of Patent: March 1, 1983Assignee: The Dow Chemical CompanyInventors: Pen-Chung Wang, James M. Renga
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Patent number: 4335136Abstract: 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: GrantFiled: March 4, 1981Date of Patent: June 15, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Saul C. Cherkofsky
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Patent number: 4326087Type: GrantFiled: July 30, 1980Date of Patent: April 20, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel, Erich Klauke
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Patent number: 4317918Abstract: 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: GrantFiled: November 3, 1980Date of Patent: March 2, 1982Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
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Patent number: 4302612Abstract: This invention is concerned with the synthesis of perfluorodialdehydes from the corresponding perfluorodiesters and with intermediates useful in the preparation of the perfluorodialdehydes.Type: GrantFiled: January 26, 1978Date of Patent: November 24, 1981Assignee: Polaroid CorporationInventors: David H. Evans, Richard B. Greenwald
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Patent number: 4301088Abstract: 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: GrantFiled: June 6, 1979Date of Patent: November 17, 1981Assignee: Dynamit Nobel AGInventor: Gunther Bernhardt
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Patent number: 4299995Abstract: 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: GrantFiled: May 13, 1980Date of Patent: November 10, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4283565Abstract: 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: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4275250Abstract: 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: GrantFiled: June 6, 1979Date of Patent: June 23, 1981Assignee: Bayer AktiengesellschaftInventors: Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Erich Klauke, Albrecht Marhold
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Patent number: 4273947Abstract: 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: GrantFiled: January 31, 1979Date of Patent: June 16, 1981Assignee: Allied Chemical CorporationInventor: Miroslav Novotny
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Patent number: 4271319Abstract: 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: GrantFiled: May 14, 1979Date of Patent: June 2, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4224244Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: May 9, 1979Date of Patent: September 23, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
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Patent number: 4223172Abstract: 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: GrantFiled: December 7, 1978Date of Patent: September 16, 1980Assignee: Gulf Research & Development CompanyInventors: Edward T. Sabourin, Charles M. Selwitz
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Patent number: 4219683Abstract: 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: GrantFiled: September 25, 1978Date of Patent: August 26, 1980Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4210610Abstract: 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: GrantFiled: December 7, 1978Date of Patent: July 1, 1980Assignee: Gulf Research and Development CompanyInventors: Edward T. Sabourin, Charles M. Selwitz