Carboxyl, Not Bonded Directly To A Ring, In Acid Moiety Patents (Class 560/105)
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Patent number: 4390721Abstract: A novel 3-endo-protected hydroxyl-tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is described which can be alkylated stereospecifically to give a 5-endo-protected hydroxyl-bicyclo[2,2,1]heptan-2-one which may then be converted via a sequence of reactions into prostaglandins of the F-series having a protecting group at the 9-position. The synthesis of the tricyclo[3,2,0,0.sup.2,7 ]heptan-6-one is also described.Type: GrantFiled: November 1, 1978Date of Patent: June 28, 1983Assignee: Allen & Hanburys LimitedInventor: Stanley M. Roberts
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Patent number: 4388322Abstract: Substituted 3-(1,2-dibromo-alkyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is halogen or optionally substituted phenyl or optionally substituted alkyl,R.sup.2 is hydrogen, halogen or optionally substituted alkyl, andY is the radical of an alcohol customary in pyrethroids, with the proviso that Y is a benzyloxy radical which is substituted by halogen and optionally substituted by at least one additional radical if R.sup.1 is halogen or methyl,which possess pesticidal properties. The acid moieties of such esters wherein R.sup.1 is optionally substituted phenyl are new compounds.Type: GrantFiled: January 19, 1981Date of Patent: June 14, 1983Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Wilhelm Stendel
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Patent number: 4381313Abstract: Novel phenylalkanoic compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 independently from each other represent hydrogen or alkyl with 1 to 8 carbon atoms, salts of such compounds and salts thereof, therapeutic uses of the phenylalkanoic compounds, or of the pharmacologically safe salts thereof for treating inflammatory diseases, tussive states, pain symptoms and pyretic diseases and pharmaceutical composition containing the phenylalkanoic compounds or the pharmacologically safe salts together with a carrier and an optional adjuvant or additive.Type: GrantFiled: May 29, 1981Date of Patent: April 26, 1983Assignee: Hommel AGInventors: Jean Heusser, Max Glasbrenner
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Patent number: 4377593Abstract: The invention relates to .alpha.-isopropyl- and .alpha.-cyclopropylphenylacetates of the formula ##STR1## wherein R.sub.1 is hydrogen, cyano, --CSNH.sub.2, allenyl, C.sub.2 -C.sub.3 alkenyl or C.sub.2 -C.sub.3 alkynyl, R.sub.2 is unsubstituted or substituted alkenyl or alkynyl, R.sub.3 is isopropyl or cyclopropyl, and each of R.sub.4 and R.sub.5 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, or both together are the methylenedioxy radical.A process for the production of these compounds and their use in pest control are disclosed.Type: GrantFiled: February 19, 1982Date of Patent: March 22, 1983Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Laurenz Gsell, Rudolf Wehrli
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Patent number: 4374263Abstract: The invention relates to an esterification process employing as a heterogeneous catalyst an inorganic oxide, e.g. silica, to which there is bonded by reaction with surface hydroxyl groups a sulphonic acid-functionalized silane.Type: GrantFiled: October 24, 1980Date of Patent: February 15, 1983Assignee: The British Petroleum Company LimitedInventors: Ronald D. Hancock, Robert Mackison
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Patent number: 4372893Abstract: Selective reduction of compounds containing reducible nitro-, nitroso-, nitrilo-, oximes or double bonds is effected by the use of a metal macrocyclic compound in prereduced form, such as a metal phthalocyanine or a metal porphyrin.Type: GrantFiled: October 6, 1980Date of Patent: February 8, 1983Inventor: Heiner Eckert
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Patent number: 4370345Abstract: Compounds of the formula ##STR1## wherein R.sup.1 denotes H, halogen, alkyl or CF.sub.3, R.sup.2 denotes H, halogen, alkyl or CF.sub.3, R.sup.3 denotes H, halogen, CN or alkyl, R.sup.4 denotes H, halogen, alkyl, phenyl or halogenophenyl, R.sup.5 denotes H, alkyl, alkynyl or CN and R.sup.6 denotes substituted dimethylcyclopropyl or 2-phenylisobutyl radicals, are effective insecticides and acaricides of the pyrethroid type.Type: GrantFiled: October 26, 1981Date of Patent: January 25, 1983Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Welter, Hilmar Mildenberger, Werner Knauf, Anna Waltersdorfer, Werner Bonin
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Patent number: 4365032Abstract: A monoester compound of a 2,2'-alkylidene bis(4,6-di-substituted phenol) useful as an antioxidant in synthetic polymers having good resistant to oxides of nitrogen fumes, represented by the formula (I), ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a C.sub.1-4 alkyl group, a C.sub.5-6 cycloalkyl group or a methyl-substituted C.sub.5-6 cycloalkyl group; and one of R.sub.3 and R.sub.4 represents a hydrogen atom and the other represents a hydrogen atom or a C.sub.1-10 alkyl group or both of them represent a methyl group; R.sub.5 represents a C.sub.4-9 alkyl group, a C.sub.3-7 cycloalkyl group, a C.sub.2-4 alkenyl group, a phenyl group, a C.sub.1-4 alkyl-substituted phenyl group, a C.sub.1-4 alkoxy-substituted phenyl group, a mono- or di- C.sub.1-4 alkyl-substituted hydroxyphenyl group, a styryl group, a benzyl group or a pyridyl group, and a method of preparing such a monoester compound.Type: GrantFiled: November 4, 1981Date of Patent: December 21, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Akihiko Yosizato, Yoshinori Morifuji, Kunio Kondo, Masatsugu Yoshino
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Patent number: 4362744Abstract: Disclosed are novel compounds of the formula ##STR1## in which R.sup.1 is hydrogen or methyl; R.sup.2 is phenyl or phenyl-methyl either of which is optionally ring substituted with lower alkyl or halogen; R is hydrogen, a tetramethylcyclopropanecarbonyl group, a 1-(substitutedphenyl)-2-methylpropylcarbonyl group, a 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropanecarbonyl group, or a substitutedvinylcyclopropanecarbonyl group; and, with respect to the indanyl substituents, the 1,3-trans isomer is present in an isomeric excess over the corresponding 1,3-cis isomer. The compounds wherein R is other than hydrogen are insecticides, and the compounds wherein R is hydrogen are insecticide intermediates.Type: GrantFiled: March 19, 1981Date of Patent: December 7, 1982Assignee: FMC CorporationInventor: Ernest L. Plummer
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Patent number: 4360689Abstract: New .alpha.-halobenzyl esters, intermediates for .alpha.-cyanobenzyl pyrethroid esters, are prepared by treating a benzaldehyde derivative with a pyrethroid acid halide. The resulting .alpha.-halobenzyl ester is treated with a water-soluble compound capable of generating cyanide ions (CN.sup.-) to give the corresponding .alpha.-cyanobenzyl esters.Type: GrantFiled: May 12, 1980Date of Patent: November 23, 1982Assignee: Shell Oil CompanyInventor: Charles H. Tieman
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Patent number: 4354036Abstract: A carboxylic acid ester, such as methyl propionate, is prepared by carbonylation of an olefin, such as ethylene in the presence of an alcohol by the use of a molybdenum-nickel or tungsten-nickel co-catalyst in the presence of a promoter comprising an organo-phosphorus compound or an organo-nitrogen compound wherein the phosphorus and nitrogen are trivalent and in the presence of a halide.Type: GrantFiled: May 28, 1981Date of Patent: October 12, 1982Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4352760Abstract: The present invention provides novel substituted heptadeca-5,9- and 5,10-dienoic acid and similar fatty acid compounds which are derivatives of certain prostaglandins and are potent thromboxane A.sub.2 inhibitors. By virtue of this pharmacological property, they represent useful pharmacological agents for a wide variety of purposes.Type: GrantFiled: December 29, 1980Date of Patent: October 5, 1982Assignee: The Upjohn CompanyInventor: Kirk M. Maxey
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Patent number: 4347378Abstract: Esters and mixed ester-amides derived from glycolic acid by substitution at the hydroxyl and carboxyl functions were prepared by conventional procedures and tested for antimicrobial activity. All of the compounds tested showed some inhibition against four microorganisms under the test conditions, and some of them had potent activity. These new compounds have properties which make it possible for them to be used as biostatic agents in commercial products.Type: GrantFiled: October 5, 1981Date of Patent: August 31, 1982Assignee: The United States of America as represented by the Secretary of AgricultureInventors: August V. Bailey, Gordon J. Boudreaux, Gene Sumrell
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Patent number: 4344961Abstract: Novel carboxylic acid esters of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are identical or different and each is hydrogen, halogen or alkyl or alkenyl of up to 5 carbon atoms,Y is 3-(2,2-dihalogenovinyl)-2,2-dimethyl-cyclopropyl or a radical of the formula ##STR2## where R.sup.4 is unbranched or branched alkyl, alkenyl or alkynyl of up to 4 carbon atoms or is an alicyclic radical of 3 to 7 carbon atoms,R.sup.5 is halogen, alkyl or alkoxy of up to 5 carbon atoms, trihalomethyl, cyano or nitro anda is from 0 to 3 andZ is a radical of the formula ##STR3## where X is oxygen, sulfur or --CH.sub.2 --,R.sup.6, R.sup.7 and R.sup.8 are halogen or alkyl, alkoxy or haloalkyl of up to 5 carbon atoms andb, c and d are from 0 to 3, their preparation and their use in insect and arachnid control.Type: GrantFiled: February 9, 1981Date of Patent: August 17, 1982Assignee: BASF AktiengesellschaftInventors: Gerd-Ulrich Schwarz, Karl Kiehs, Heinrich Adolphi
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Patent number: 4343796Abstract: The invention relates to compounds of the formula: ##STR1## in which R.sub.1 and R.sub.2 are the same or different groups selected from hydrogen or acyl orR.sub.1 and R.sub.2 together may represent an acetal group, andX and Y are the same or different groups selected from hydroxy, an etherified hydroxy and an esterified hydroxy group,having valuable lipid lowering, anti-inflammatory and immuno-modulating properties.Type: GrantFiled: June 11, 1981Date of Patent: August 10, 1982Assignee: AKZO NVInventor: Marinus B. Groen
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Patent number: 4339594Abstract: Phenylacetic acid and the simple derivatives thereof are prepared by catalytic hydrogenation of mandelic acid and its appropriate derivatives in the presence of a noble metal catalyst in aqueous solution which is free from mineral acid, especially free from hydrochloric acid.Type: GrantFiled: October 31, 1980Date of Patent: July 13, 1982Assignee: Hoechst AktiengesellschaftInventors: Werner Spielmann, Georg Schaeffer
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Patent number: 4336399Abstract: A process for producing a carboxylic acid and/or its ester, which comprises reacting an alcohol or ether with carbon monoxide in the presence of elemental nickel or a nickel compound, iodine or an iodine compound and an organic compound of a trivalent nitrogen-group element; wherein the iodine or iodine compound is selected from the following formulae (I) to (IV),RX.sub.n (I)wherein R represents a hydrogen atom or an alkyl or alkylene group, X represents an iodine or bromine atom, and n is an integer of 1 to 3, at least one of n.multidot.X's being an iodine atom,I.sub.2 or I.sub.3 - (II)RCOI (III)wherein R represents an alkyl group,MI.sub.2 (IV)wherein M represents an alkaline earth metal, and the amount of the iodine or iodine compound is such that the amount of the free iodine or iodine compound not chemically bonded to the nickel or nickel compound or the organic compound of a nitrogen-group element is at least 0.Type: GrantFiled: November 10, 1980Date of Patent: June 22, 1982Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Yuh Miyauchi
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Patent number: 4335251Abstract: The present invention relates to the phenyl-propionic acid ester derivative of the following formula: ##STR1## The compound obtained by the present invention possesses a high degree of analgetic, antipyretic and anti-inflammatory activity and causes little side effects on the gastro-intestinal tracts, when administered orally and topically, and it may be useful as an oral and topical analgesic, antipyretic and anti-inflammatory agent.Type: GrantFiled: August 5, 1980Date of Patent: June 15, 1982Assignee: Hisamitsu Pharmaceutical Co. Inc.Inventors: Kanji Noda, Akira Nakagawa, Yuji Ishikura, Hiroyuki Ide
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Patent number: 4335118Abstract: Phenylacetates of the formula ##STR1## wherein R.sub.1 is isopropyl or cyclopropyl, R.sub.2 is hydrogen, cyano, ethynyl, prop-1-ynyl or --CSNH.sub.2, and X.sub.1 is hydrogen, methyl, fluorine or chlorine, a process for their production and method of use thereof in pest control.Type: GrantFiled: October 9, 1980Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hanspeter Fischer, Rudolph C. Thummel, Rudolf Wehrli
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Patent number: 4334042Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.Type: GrantFiled: July 23, 1979Date of Patent: June 8, 1982Assignee: Kuraray Co. Ltd.Inventors: Mitsuo Matsumoto, Masuhiko Tamura
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Patent number: 4333950Abstract: Novel compounds of the formula ##STR1## are disclosed in which R.sup.1 is a phenyl, phenoxy, phenylthio, benzyl or heterocyclic radical which may be substituted, R.sup.2 is hydrogen, a substituted-vinylcyclopropanecarbonyl group, a tetramethylcyclopropanecarbonyl group, or a 1-(substituted-phenyl)-2-methylpropylcarbonyl group, and the isomer of S configuration at C-2 of the indanyl ring is present in an enantiomeric excess over the isomer of R configuration. Also disclosed is a method for preparing the optically active alcohols. The compounds wherein R.sup.2 is other than hydrogen are insecticides.Type: GrantFiled: December 31, 1980Date of Patent: June 8, 1982Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4334079Abstract: A process for preparing certain substituted benzyl esters of phenylacetic acids by esterification in a solvent in which the salt of the acid is insoluble, and in the presence of a phase transfer catalyst.Type: GrantFiled: November 3, 1980Date of Patent: June 8, 1982Assignee: Eli Lilly and CompanyInventors: James M. Greene, Charles A. Bunnell
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Patent number: 4328356Abstract: Esters of arylacetic acids, more particularly lower alcohol esters of arylacetic acids, including those substituted on the methylene group, are prepared by rearrangement of the corresponding alpha-halo-alkylarylketones with Ag compounds in lower alcohols and in an acid medium. From the alkyl esters so prepared, their respective free acids can be obtained, if desired, by various means such as hydrolysis or the shift with mineral acids of the alkaline salts prepared by reaction with alkali, etc.Type: GrantFiled: February 15, 1980Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Claudio Giordano, Francesco Casagrande
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Patent number: 4325877Abstract: 5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF.sub.3, CHF.sub.2 or CH.sub.2 F; R.sub.1 is H or akyl of 1-4 carbon atoms; and R.sub.2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R.sub.1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R.sub.2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R.sub.1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R.sub.2 -5-R.sub.1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br.sup.+ to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e.g., via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.Type: GrantFiled: June 16, 1980Date of Patent: April 20, 1982Assignee: Richardson-Merrell Inc.Inventors: Brian W. Metcalf, Jerry L. Adams
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Patent number: 4323513Abstract: This invention is concerned with improving ethylene glycol ester production from the reaction of carbon monoxide and hydrogen in a homogeneous liquid phase mixture containing a ruthenium carbonyl complex catalyst and acyl compound by maintaining the combined concentration of methyl ester, ethylene glycol ester and water in the reaction medium at less than about 30 volume percent. In a preferred embodiment, a continuous process is operated in such a manner that the methyl ester, ethylene glycol ester and water products are removed from the reactor so as to maintain their total volume concentration in the reaction medium at less than about 30 percent.Type: GrantFiled: November 4, 1980Date of Patent: April 6, 1982Assignee: Union Carbide CorporationInventor: Bernard D. Dombek
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Patent number: 4316986Abstract: Carboxylic ester and acyl fluoride groups are interchanged in the presence of a metal fluoride catalyst or a metal fluoride/strong sulfonic acid catalyst combination to produce fluorinated mono- and diacyl fluorides.Type: GrantFiled: September 23, 1980Date of Patent: February 23, 1982Assignee: E. I. DuPont de Nemours & CompanyInventors: David C. England, Robert L. Kraft, Carl G. Krespan
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Patent number: 4316045Abstract: A process for the catalytic preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted in liquid medium with an organic peracid in the presence of a catalytic amount of an aryl iodide, to form the desired aryl carboxylate.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4316044Abstract: Isovaleric acid derivatives having the formula ##STR1## wherein typical representations of X is halophenyl, R.sub.1 is hydrogen or cyano, R.sub.2 is hydrogen or lower alkyl, and Y is halophenyl. These derivatives possess insecticidal and acaricidal properties. The process for their preparation is described.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: Nippon Soda Company LimitedInventors: Keiichi Ishimitsu, Isamu Kasahara, Tomio Yamada, Michihiko Matsuda, Hidemitsu Takahashi, Shuichi Soma
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Patent number: 4316046Abstract: A process for the preparation of aryl carboxylates is provided in which an arylmetallo carboxylate is contacted with an aryliodoso carboxylate in liquid medium to form the desired aryl carboxylate. Promoters can be employed to increase the rate of reaction and improve selectivity to the aryl carboxylate.Type: GrantFiled: August 29, 1980Date of Patent: February 16, 1982Assignee: The Halcon SD Group, Inc.Inventor: Lawrence C. Costa
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Patent number: 4313956Abstract: Novel, transient prodrug forms of the phenolic dihydroxy sympathomimetic amines have (i) the structural formula (I): ##STR1## wherein X is O, S or NR.sup.5 ; n is 1 or 2; R.sup.1 is the monodehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 1, and the didehydroxylated residue of a phenolic, nuclear dihydroxy natural sympathetic or sympathomimetic amine when n is 2; R.sup.Type: GrantFiled: December 28, 1979Date of Patent: February 2, 1982Assignee: INTERx Research Corp.Inventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4311706Abstract: Novel, transient prodrug forms of dopa and dopamine have (i) the structural formula (I): ##STR1## wherein each R is independently selected from the group consisting of hydrogen, R.sup.3 -CO- and ##STR2## wherein X is O, S or NR.sup.6 ; R.sup.1 is hydrogen or --COOR.sup.8 ; R.sup.2 is hydrogen or OR; R.sup.Type: GrantFiled: January 22, 1980Date of Patent: January 19, 1982Assignee: INTERx Research CorporationInventors: Nicholas S. Bodor, Kenneth B. Sloan, Stefano A. Pogany
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Patent number: 4310709Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.Type: GrantFiled: April 23, 1980Date of Patent: January 12, 1982Assignee: BASF AktiengesellschaftInventor: Walter Rebafka
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Patent number: 4310540Abstract: Benzyl esters of the formula ##STR1## in which n is 1,2,3,4, or 5,R.sup.2 is hydrogen, C.sub.1-4 -alkyl, cyano or ethynyl,R.sup.3 is the radical of a carboxylic acid customary in pyrethroids or pyrethroid-like compounds, andat least one R.sup.1 is fluoroalkoxy or fluoroalkylmercapto, or two together are fluoromethylene- or fluoroethylene-dioxy, and the others, if present, are hydrogen or various radicals,which possess arthropodicidal properties. Various alcohols, amines, aldehydes, halides, and the like, corresponding to the alcohol moieties of the esters are also synthesized.Type: GrantFiled: April 16, 1979Date of Patent: January 12, 1982Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Albrecht Marhold, Wolfgang Behrenz, Ingeborg Hammann
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Patent number: 4310688Abstract: The level of hydrolyzable chloride-containing impurities in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by reacting the impurities with a vicinal epoxide-containing compound and then fractionally distilling the mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) in a methylene chloride solution containing 0.084 weight percent of hydrolyzable chloride is contacted with a diglycidyl ether of bisphenol A at 23.degree. C. This reaction mixture is then fractionally distilled to separate the IEM from the methylene chloride first cut and the epoxy resin residue. The hydrolyzable chloride level of the distilled IEM product is only 0.03 weight percent.Type: GrantFiled: October 22, 1979Date of Patent: January 12, 1982Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4301044Abstract: Zwitterionic surfactant compounds are made readily biodegradable in the environment by the inclusion of a biochemically and/or hydrolytically labile chemical linkage located between the cationic and anionic charge centers of the compounds and anywhere from the second to the tenth atom distant from the cationic charge center. The biodegradable linkage is preferably an ester or amide. The alkoxylated zwitterionic surfactants herein exhibit outstanding particulate soil removal performance and are also effective in removing oily soils from fabrics, in addition to being readily biodegradable. Also described are detergent compositions containing the zwitterionic surfactants, and, optionally containing cosurfactants and detergent builders.Type: GrantFiled: January 22, 1980Date of Patent: November 17, 1981Assignee: The Procter & Gamble CompanyInventors: George E. Wentler, Joseph McGrady, Eugene P. Gosselink, William A. Cilley
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Patent number: 4301084Abstract: In a process for the preparation of a carboxylic acid ester of .beta.-formyl-crotyl alcohol by rearrangement of the corresponding carboxylic acid ester of 2-formyl-2-hydroxy-but-3-ene or of an acetal or acylate thereof in the presence of copper or a copper compound, followed, where relevant, by hydrolytic cleavage of the acetal or acylate, more especially in the preparation of 4,4-dimethoxy-3-methyl-crotyl acetate, the yield is improved by carrying out the rearrangement in the presence of copper (I) chloride as the catalyst and ensuring that low-boiling by-products formed during the rearrangement are removed.The products are of great importance as starting materials for an industrial synthesis of vitamin A and its derivatives.Type: GrantFiled: August 31, 1979Date of Patent: November 17, 1981Assignee: BASF AktiengesellschaftInventors: Harald Laas, Axel Nissen, Bernd Meissner
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Patent number: 4301062Abstract: A novel diester compound of the formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a group of the formula (II): ##STR2## wherein n is an integer of 0 to 4; and m an integer of 1 to 5, is found to be capable of imparting excellent flame-retardancy to various inflammable polymeric materials such as polystyrene, polyester, polyamide, polyphenylene oxide, etc. without deleterious effects on other physical properties of such polymeric materials.Type: GrantFiled: October 11, 1979Date of Patent: November 17, 1981Assignee: Asahi Dow LimitedInventors: Izumi Yamashita, Kazuo Yoshida, Yuji Kusumi, Kunio Fukuda, Kichiya Tazaki
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Patent number: 4299844Abstract: Anti-inflammatory naphthyl compounds, their preparation and pharmaceutical compositions containing the same. The anti-inflammatory activity has a wide spectrum coupled with low side effects such as gastrointestinal irritancy or oestrongenicity. The compounds possess a chiral center at C-2 and can exist as mixtures of optical isomers or as substantially pure optical isomers.Type: GrantFiled: July 9, 1979Date of Patent: November 10, 1981Assignee: Beecham Group LimitedInventor: Alexander C. Goudie
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Patent number: 4296244Abstract: The present invention provides a novel organic compound, (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid, and a process for the preparation thereof comprising the steps of:a. converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b. cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,c. hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid, andd. hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid.Type: GrantFiled: November 7, 1979Date of Patent: October 20, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
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Patent number: 4289896Abstract: Phosphonic acids are suitable catalysts for the transesterification of alkyl esters of carboxylic acids with aliphatic or cycloaliphatic diols containing more than 3 carbon atoms.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventor: Lothar Buxbaum
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Patent number: 4289892Abstract: Active hydrogen-containing fluorochemical is used as a foam stabilizer for polyurethane foams. For example, rigid or flexible polyurethane foams with high or low density and uniform cellular structure are prepared using fluoroaliphatic radical-substituted poly(oxyalkylene) polyols as foam stabilizers.Type: GrantFiled: April 30, 1979Date of Patent: September 15, 1981Assignee: Minnesota Mining and Manufacturing CompanyInventor: Fredrich A. Soch
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Patent number: 4288385Abstract: The present invention relates to certain novel substituted 2,6-dinitroaniline compounds. It further relates to certain preemergence herbicidal methods employing said novel dinitroanilines for the selective control of certain grasses and broadleaved weeds in the presence of graminaceous crops, especially rice. This invention also relates to the postemergence control of crabgrass and certain broadleaved weeds in the presence of established turf grasses.Type: GrantFiled: July 25, 1979Date of Patent: September 8, 1981Assignee: American Cyanamid Co.Inventors: Albert W. Lutz, Robert E. Diehl
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Patent number: 4285971Abstract: Halogenated phenol esters of the formula ##STR1## wherein X represents chlorine or fluorine and R represents hydrogen, alkyl of 1 to 22 carbon atoms, alkenyl of 2 to 22 carbon atoms, benzyl which is unsubstituted or substituted by chlorine or bromine atoms, or phenyl which is unsubstituted or substituted by alkyl or alkoxy, each of 1 to 4 carbon atoms, carboxyl, chlorine and/or bromine. The invention also relates to a method of protecting organic and inorganic material from attack by microorganisms, in particular of providing textiles with an antimicrobial and rotproof finish, of protecting wood from rot, and of preventing the formation of slime in the manufacture of paper.Type: GrantFiled: July 30, 1979Date of Patent: August 25, 1981Assignee: Ciba-Geigy CorporationInventor: Rene Muntwyler
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Patent number: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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Patent number: 4277617Abstract: Novel esters in the form of their stereoisomers and mixtures of stereoisomers of the formula ##STR1## wherein X is selected from the group consisting of fluorine, chlorine and bromine R.sub.1 is selected from the group consisting of ##STR2## Y.sub.1 and Y.sub.2 may both be methyl and when Y.sub.1 is hydrogen, Y.sub.2 is selected from the group consisting of ##STR3## and Y.sub.3 and Y.sub.4 are individually selected from the group consisting of fluorine, bromine and chlorine or the group consisting of hydrogen and methyl, Z is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms and alkoxy of 1 to 4 carbon atoms, and when Y.sub.2 is ##STR4## R.sub.2 is selected from the group consisting of ##STR5## A is selected from the group consisting of ##STR6## and when Y.sub.2 is --CHBr--CCl.sub.2 Br, R.sub.2 is m-phenoxy-phenyl and when R.sub.1 is R.sub.1 ' and Y.sub.Type: GrantFiled: October 13, 1978Date of Patent: July 7, 1981Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute, Andre Teche
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Patent number: 4277494Abstract: Acetates of the formula ##STR1## wherein X.sub.1 represents hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, X.sub.2 represents hydrogen or halogen, and Y represents hydrogen, halogen or methyl, processes for their manufacture and a method of controlling pests which comprises the use of these compounds.Type: GrantFiled: June 18, 1979Date of Patent: July 7, 1981Assignee: Ciba-Geigy CorporationInventors: Saleem Farooq, Peter Ackermann, Jozef Drabek, Laurenz Gsell, Odd Kristiansen, Rudolf Wehrli
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Patent number: 4276225Abstract: A carboxylic acid ester activated in .alpha.-position by a keto, ester or nitrile group, i.e. of the formula ##STR1## where X is COOR.sup.4, COR.sup.5 or CN, and the several R's can have various meanings but only R.sup.1 and R.sup.2 can be hydrogen, is decarbalkoxylated by heating in the presence of a salt, e.g. sodium chloride, and a phosphorus-containing solvent such as a phospholine oxide, phospholane oxide or phosphetane oxide of the formulas ##STR2## wherein a-k and R can have varied definitions. Water is present either at the outset or end of the reaction before product separation. The reaction proceeds smoothly and in good yields.Type: GrantFiled: August 8, 1977Date of Patent: June 30, 1981Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Hellmut Hoffmann
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Patent number: 4275219Abstract: The invention relates to a novel process and novel intermediates useful in the preparation of sympathomimetic amines. The pharmacologically useful final products, which are acyl derivatives of mono- and dihydroxy aromatic amines (e.g., catechol amines) can be prepared in optically active or racemic form by reacting the corresponding mono- or dihydroxy aromatic amine with a reagent capable of forming the N-tert-butoxycarbonyl derivative thereof; reacting the novel intermediate thus obtained with an acyloxymethyl chloride to afford the corresponding novel mono- or diacylated N-protected aromatic amine; and removing the N-protecting group therefrom.Type: GrantFiled: September 24, 1979Date of Patent: June 23, 1981Assignee: INTERx Research CorporationInventor: Jacob A. Zupan
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Patent number: 4274998Abstract: A novel diester compound of the formula (I): ##STR1## wherein each of R.sub.1 and R.sub.2 represents a group of the formula (II): ##STR2## wherein X is bromine atom; Y at least one group selected from the group consisting of alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, hydroxyl group and primary, secondary or tertiary amino groups; p an integer of 0 to 4; q an integer of 1 to 4; r an integer 1 to 4 and (q+r) is equal to an integer of not more than 5, is found to be capable of imparting excellent flame-retardancy to various inflammable polymeric materials such as polystyrene, polyester, polyamide, polyphenylene oxide, etc. without deleterious effects on other physical properties of such polymeric materials.Type: GrantFiled: October 11, 1979Date of Patent: June 23, 1981Assignee: Asahi-Dow LimitedInventors: Izumi Yamashita, Kunio Fukuda, Kichiya Tazaki
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Patent number: 4271186Abstract: The invention relates to certain new stilbene derivatives of the general formula ##STR1## in which R, R.sup.1 and R.sup.2 have the below mentioned meaning, to a process for their preparation and to their use as arthropodicides, especially as insecticides and acaricides.Type: GrantFiled: June 29, 1979Date of Patent: June 2, 1981Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Rainer Fuchs, Ingeborg Hammann, Wilhelm Stendel