Halogen In Acid Moiety Patents (Class 560/30)
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Patent number: 4401675Abstract: Alkyl 3-aryl-3-acyl-2-methyl-carbazates which are highly effective fungicides in the fight against fungus infections in useful plants are disclosed, as is the use thereof in fighting phytopathogenous fungi.Type: GrantFiled: October 2, 1981Date of Patent: August 30, 1983Assignee: Montedison S.p.A.Inventors: Luigi Garlaschelli, Franco Gozzo, Luigi Mirenna
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Patent number: 4395565Abstract: A process for the preparation of aromatic urethans by reaction between aromatic amines and alkyl carbonates, said reaction being carried out in the presence of a catalyst composed of an alcoholate of an alkali metal or an alkaline earth metal. The reaction is caused to take place at a temperature which is variable from +50.degree. C. and +150.degree. C., in the liquid phase and with a molar ratio of the carbonate to the amine of from 10:1 to 1:10.Type: GrantFiled: January 15, 1982Date of Patent: July 26, 1983Assignee: Anic S.p.A.Inventors: Ugo Romano, Giancarlo Fornasari, Sandro Di Gioacchino
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Patent number: 4388238Abstract: A process for the preparation of N,O-disubstituted urethanes. Primary amines and alcohols are reacted with organic compounds having carbonyl groups at 120.degree. to 350.degree. C. Suitable carbonyl-containing compounds include N-unsubstituted urethanes. N-mono-substituted, N,N'-disubstituted ureas, or polyureas may be used in combination with the N-unsubstituted urethane. The product urethanes are particularly suitable for the preparation of isocyanates.Type: GrantFiled: October 15, 1980Date of Patent: June 14, 1983Assignee: Bayer AktiengesellschaftInventors: Peter Heitkamper, Klaus Konig, Rudolf Fauss, Kurt Findeisen
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Patent number: 4385069Abstract: N-allenyl-acetanilides of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl or halogen,R.sup.2 represents hydrogen or alkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen or alkyl andR.sup.6 represents furyl, tetrahydrofuryl, thiophenyl or tetrahydrothiophenyl; isoxazolyl which is optionally substituted by alkyl; alkyl, alkenyl or alkynyl, in each case optionally substituted by cyano or thiocyano; dihalogenoalkyl; or the grouping --CH.sub.2 --Az, --CH.sub.2 --OR.sup.7, --OR.sup.7 --SR.sup.7, --CH.sub.2 --OSO.sub.2 R.sup.7, --COOR.sup.7 or ##STR2## wherein R.sup.7 represents an optionally substituted alkyl, alkenyl, alkynyl or alkoxyalkyl radical and Az represents pyrazol-1-yl, 1,2,4-triazol-1-yl or imidazol-1-yl.which possess fungicidal properties.Type: GrantFiled: March 31, 1980Date of Patent: May 24, 1983Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Winfried Lunkenheimer, Wilhelm Brandes
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Patent number: 4378373Abstract: Derivatives of benzoylphenoxyalkanoic acids corresponding to the formula: ##STR1## wherein: X represents for example a halogen, R.sup.1 and R.sup.2 represent for example alkyl groups, R represents for example an aminoacid; and the salts thereof are new products showing antilipaemic and anticholesterolemic pharmacological activity.Type: GrantFiled: April 20, 1981Date of Patent: March 29, 1983Assignee: Alfa Farmaceutici S.p.A.Inventors: Valerio Borzatta, Manlio Cristofori, Mauro Morotti, Giuseppe Mascellani
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Patent number: 4375000Abstract: A process for the preparation of an aryl mono-, di-, and/or polyurethane comprising the steps of A. reacting a primary aromatic mono-, di-, and/or polyamine with an O-alkyl carbamate in the presence of an alcohol at temperatures greater than 160.degree. C., andB. separating the ammonia and other by-products from the aryl mono-, di-, and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.Type: GrantFiled: March 31, 1980Date of Patent: February 22, 1983Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae, Wolfgang Harder
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Patent number: 4373105Abstract: New m-anilide-urethanes, processes for their manufacture, herbicides containing these compounds, and processes for controlling unwanted plant growth with these compounds.Type: GrantFiled: March 11, 1981Date of Patent: February 8, 1983Assignee: BASF AktiengesellschaftInventors: Wolfgang Rohr, Ulrich Schirmer, Bruno Wuerzer
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Patent number: 4370497Abstract: The present invention relates to the use of telluroxides as mild and selective oxidizing agents serving to oxidize certain functions, notably >C.dbd.S groups, in the presence of other relatively easily oxidized functions which remain unaffected; telluroxides of interest as oxidizing agents include, for example, compounds of the formula: ##STR1## wherein R and R.sup.1, which may be the same or different, each represent an optionally substituted aryl or heterocyclic group; or R and R.sup.1 together with the tellurium atom therebetween represent a heterocyclic ring, which may contain one or more further heteroatoms, and which may carry substituents and/or fused aromatic rings.Type: GrantFiled: August 7, 1980Date of Patent: January 25, 1983Inventors: Derek H. R. Barton, Steven V. Ley, Clive A. Meerholz
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Patent number: 4339592Abstract: A urethane is produced by reacting an organic nitro compound with carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst and a co-catalyst. This reaction is conducted in the liquid phase at elevated temperature and pressure. The catalyst employed is an element and/or compound of an element from the group of noble metals of the 8th Secondary Group of the Periodic Table. The co-catalyst used is formed from (1) a component taken from the group consisting of iron oxychloride, a mixture of iron compounds containing iron oxychloride and oxide-chloride combinations and (2) metallic iron or an iron alloy in finely divided or high surface form. The oxides which may be used in the oxide-chloride combinations of co-catalyst component (1) are the oxides and/or oxide hydrates of tetravalent tin, trivalent chromium, hexavalent molybdenum, hexavalent tungsten, pentavalent vanadium, divalent iron and trivalent iron.Type: GrantFiled: February 26, 1981Date of Patent: July 13, 1982Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Christian Rasp, Gunter Stammann, Johann Grolig
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Patent number: 4337349Abstract: Dimethacrylates are provided having the following chemical structure: ##STR1## where n represents a number of 2 to 8;R.sub.1 and R.sub.2 are the same or different and are hydrogen or groups of the formula: ##STR2## where R.sub.3 is an aliphatic, aromatic or cycloaliphatic group having 1 to 14 carbon atoms. These compounds are useful in dental material which cures to form polymers having high mechanical strength, low water sorption, resistance to staining, good color stability when exposed to short-wave radiation (e.g., sunlight) and good chemical resistance to the oral environment. Also provided are a method for polymerizing these compounds in situ on teeth and a tooth comprising polymers of these compounds.Type: GrantFiled: June 2, 1980Date of Patent: June 29, 1982Assignee: Scientific Pharmaceuticals, Inc.Inventors: Jan A. Orlowski, David V. Butler, Patrick D. Kidd
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Patent number: 4328165Abstract: Novel phenylcarbamic acid chlorides, and their preparation by reacting N-mono-substituted phenylenediamines with excess phosgene and then reacting the products with thioalcohols, alcohols, hydroxylamines or amines.The novel phenylcarbamic acid chlorides of the formula I obtainable by the process of the invention are valuable intermediates for the preparation of crop protection agents, especially herbicides.Type: GrantFiled: February 12, 1980Date of Patent: May 4, 1982Assignee: BASF AktiengesellschaftInventor: Ulrich Schirmer
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Patent number: 4325966Abstract: This invention relates to alkenyl and alkynyl acylanilide derivatives useful as pesticides, especially as fungicides, to a process for preparing them, to pesticidal compositions containing them, and to a method of combating pests using them.Type: GrantFiled: April 27, 1979Date of Patent: April 20, 1982Assignee: Imperial Chemical Industries LimitedInventor: Nazim Punja
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Patent number: 4326071Abstract: Novel compounds of the following general formula are useful pharmacological agents: ##STR1## wherein Y is FCH.sub.2 - or F.sub.2 CH-; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, -NR.sub.10 R.sub.11 wherein each of R.sub.10 and R.sub.11 is hydrogen or a straight or branched alkyl group of from 1 to 4 carbon atoms or ##STR2## wherein R.sub.12 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR3## wherein R.sub.8 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and n is the integer 2 or 3; pharmaceutically acceptable salts and individual optical isomers thereof.Type: GrantFiled: September 28, 1977Date of Patent: April 20, 1982Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4318731Abstract: A novel .DELTA..sup.2 -1,2,4-triazolin-5-one derivative having a herbicidal activity, which is represented by the formula ##STR1## wherein, R.sup.1 is a C.sub.1 -C.sub.4 alkyl; R.sup.2 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, or a C.sub.2 -C.sub.4 alkenyl group; and X is a hydroxy group, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.6 alkyloxy group, an alkyloxyalkyloxy group of which two alkyls may be same as or different from each other and each alkyl is of C.sub.1 -C.sub.4, a C.sub.2 -C.sub.4 alkenyloxy, or an alkyloxycarbonylalkyloxy group of which two alkyls may be same as or different from each other and each alkyl is of C.sub.1 -C.sub.4.Type: GrantFiled: June 24, 1980Date of Patent: March 9, 1982Assignee: Nihon Nohyaku Co., Ltd.Inventors: Mitsuru Kajioka, Hitoshi Kurono, Katsumasa Okawa, Tatsuo Harada
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Patent number: 4316042Abstract: Compounds of the formula II: ##STR1## are produced by reacting a compound of the formula III ##STR2## with a compound of the formula IV: ##STR3## wherein R.sub.1 is hydrogen, alkyl of 1 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by cycloalkyl of 3 to 6 carbon atoms, polyhaloalkyl of 1 to 5 carbon atoms, allyl, propargyl, enzyl or aryl,R.sub.2 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, trifluoromethyl, nitro, alkylamino or dialkylamino, wherein the alkyl groups have 1 to 4 carbon atoms, or aryl,R.sub.3 is hydrogen, halogen, alkyl or alkoxy, each of 1 to 4 carbon atoms, or aryl,R.sub.4 is hydrogen, nitro, halogen, alkyl or alkoxy each of 1 to 4 carbon atoms or aryl,R.sub.5 is hydrogen, halogen, alkyl, alkylthio or alkoxy each of 1 to 4 carbon atoms, nitro, trifluoromethyl or aryl,R.sub.6 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms, benzyl or aryl, andR is alkyl of 1 to 4 carbon atoms.Type: GrantFiled: August 15, 1979Date of Patent: February 16, 1982Assignee: Sandoz Ltd.Inventor: Peter Funfschilling
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Patent number: 4313008Abstract: The S-enantiomer of 3-chloro-1,2-propanediol is prepared by reaction of a chlorodeoxy-D-saccharide having the partial structure. ##STR1## to cleave the glycol, reduce the aldehyde so formed to an alcohol, and hydrolyse the alcohol under mild acidic conditions.Type: GrantFiled: May 17, 1979Date of Patent: January 26, 1982Assignee: Tate & Lyle Ltd.Inventor: Haydn F. Jones
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Patent number: 4304922Abstract: Production of urethanes by the oxycarbonylation reaction of N,N'-disubstituted ureas and organic compounds containing at least one hydroxyl group with carbon monoxide in the presence of molecular oxygen and/or organic nitro compounds and a catalyst system comprising (a) a noble metal and/or noble metal compound of the eighth subgroup of the periodic system of elements and (b) a compound of an element and/or elements of the third to fifth main group and/or first to eighth subgroup of the periodic system of elements characterized in that said compounds are capable of undergoing Redox reactions under the reaction conditions.Type: GrantFiled: February 27, 1980Date of Patent: December 8, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gunter Stammann
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Patent number: 4303793Abstract: A stable, flowable aqueous dispersion of agriculturally acceptable carbamate compound is prepared by wet-milling an aqueous carbamate suspension, said suspension prepared by subsurface injection of molten carbamate into a stirred aqueous salt solution.Type: GrantFiled: September 22, 1980Date of Patent: December 1, 1981Assignee: PPG Industries, Inc.Inventors: Leo J. Paridon, Robert E. Downing
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Patent number: 4297501Abstract: A process for producing urethanes by reacting primary amines, carbon monoxide and organic hydroxyl compounds in the presence of molecular oxygen and/or organic nitro compounds as oxidizing agents and a catalyst system comprising a noble metal and/or a compound of a noble metal of the 8th subgroup of the Periodic System of Elements and a compound capable of undergoing Redox reactions under reaction conditions of the 3rd to 5th main group and/or 1st to 8th subgroup of the Periodic System of Elements.Type: GrantFiled: February 27, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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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: 4282368Abstract: p-Substituted, aromatic carbamic acid esters are prepared by reacting an aromatic carbamic acid ester with an olefin in the presence of an inorganic acid or sulfonic acid.The aromatic carbamic acid esters obtainable by the process of the invention are active ingredients for pesticides and drugs, as well as valuable starting materials for the preparation of such ingredients and of dyes.Type: GrantFiled: June 2, 1980Date of Patent: August 4, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler
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Patent number: 4282169Abstract: Disclosed are selected 2-acyl- or 2-thioacyl-1-trichloroacetimidoylhydrazines having the formula: ##STR1## wherein X is an atom selected from the group consisting of oxygen and sulfur; and R is a hydrogen, lower alkyl or lower alkoxy group having 1 to 4 carbon atoms, or an unsubstituted or substituted phenyl group. These compounds are disclosed to be agricultural fungicides.Type: GrantFiled: February 19, 1980Date of Patent: August 4, 1981Assignee: Olin CorporationInventors: Eugene F. Rothgery, Lawrence E. Katz
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Patent number: 4278805Abstract: A process for the preparation of an aryl-mono and/or polyurethane comprising the steps ofA. reacting a primary aromatic mono, di-, and/or polyamine with an O-alkyl carbamate in the presence of alcohol and catalysts, andB. separating the ammonia and other by-products from the aliphatic and/or cycloaliphatic di- and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.Type: GrantFiled: March 31, 1980Date of Patent: July 14, 1981Assignee: BASF AktiengesellschaftInventors: Franz Merger, Friedrich Towae
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Patent number: 4267353Abstract: This invention relates to an improved process for the preparation of urethanes by the reaction of aromatic nitro compounds with alcohols and carbon monoxides in the presence of catalyst systems containing sulphur and/or selenium and/or compounds of these elements.Type: GrantFiled: August 22, 1979Date of Patent: May 12, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Scholl, Armin Zenner
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Patent number: 4266070Abstract: A process for the production of urethanes is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide and an organic compound containing at least one hydroxyl group in the presence of a catalyst comprising a member selected from the group consisting of carbonyls of Co, Mo, Ti, Rh, Fe, Ni and mixtures thereof. Urethane yields and selectivities are further improved by conducting the reaction in the additional presence of an organic compound containing at least one C.dbd.N or C.dbd.C group. When such unsaturated organic compounds are employed, the catalyst can additionally comprise iridium carbonyl.Type: GrantFiled: May 25, 1979Date of Patent: May 5, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4262130Abstract: The present invention relates to an improved process for the production of urethanes (carbamic acid esters) by the reaction of organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of palladium and/or palladium compounds and a cocatalyst which consists of a mixture of one or more iron oxides and/or iron hydroxides and activating chloride-containing additives.Type: GrantFiled: January 17, 1980Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp
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Patent number: 4260781Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group, and a metal reactant comprising at least one member selected from the group consisting of compounds and complexes of Group VIII of the Periodic Table.Type: GrantFiled: May 25, 1979Date of Patent: April 7, 1981Assignee: Halcon Research and Development Corp.Inventor: Robert J. Harvey
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Patent number: 4258201Abstract: A process for the production of carbamates is provided in which an organic primary or secondary amine is contacted, in the substantial absence of reactive oxygen, with a source of carbon monoxide, an organic compound containing at least one hydroxyl group and a source of sulfur, selenium or tellurium, in the presence of an effective amount of a catalyst selected from the group consisting of non-halide compounds and complexes of metals of Groups IVB, VB, VIB, VIIB, VIII, IB and IIIA of the Periodic Table. Further improved results are obtained by employing in the reaction zone at least one promoter selected from the group consisting of metals of Group IA and IIA of the Periodic Table.Type: GrantFiled: January 29, 1979Date of Patent: March 24, 1981Assignee: Halcon Research and Development Corp.Inventor: David Moy
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Patent number: 4251667Abstract: A process for the preparation of aromatic urethanes by reacting an aromatic amine, an alcohol and carbon monoxide in the presence of a catalytic quantity of a copper salt, oxygen and a dehydrating agent is disclosed. The reaction is preferably carried out using a copper halide catalyst and dehydrating agents which combine with water to release the alcohol used in the preparation of the urethane product.Type: GrantFiled: June 6, 1979Date of Patent: February 17, 1981Assignee: Atlantic Richfield CompanyInventor: Haven S. Kesling, Jr.
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Patent number: 4238503Abstract: This invention relates to the utility of certain anilide ureas as biocidal agents having the formula ##STR1## R is selected from the group of alkyls having from 1 to 6 carbon atoms, haloalkyls having from 1 to 6 carbon atoms, NR.sub.1 R.sub.2, NHR.sub.1, OR.sub.1 and SR.sub.1 in which R.sub.1 and R.sub.2 are independently lower alkyl having from 1 to 6 carbon atoms, X and Y are independently selected from the group consisting of H, Cl, CF.sub.3 and NHCOR.sub.3 and R.sub.3 is selected from the group of lower alkyl having from 1 to 6 carbon atoms, haloalkyl having from 1 to 6 carbon atoms, NR.sub.4 R.sub.5, NHR.sub.4, OR.sub.4 and SR.sub.4 in which R.sub.4 and R.sub.5 are independently lower alkyl having from 1 to 6 carbon atoms.Type: GrantFiled: March 1, 1979Date of Patent: December 9, 1980Assignee: Stauffer Chemical CompanyInventors: Eugene G. Teach, Don R. Baker
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Patent number: 4230635Abstract: Disclosed are novel substituted 4'-polyhaloisopropylsulfonanilides which are anti-hypertensive agents useful in the treatment of mammalian hypertension. Additionally, the compounds exhibit herbicidal and fungicidal activity. The compounds are prepared by contacting a 4-polyhaloisopropylaniline with the appropriate substituted-sulfonyl chloride.Type: GrantFiled: August 15, 1978Date of Patent: October 28, 1980Assignee: Schering CorporationInventor: Bernard R. Neustadt
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Patent number: 4230484Abstract: A method of controlling pollen formation in a hermaphrodite plant, the method comprising applying to the plant, to seed of the plant or to the locus surrounding the plant or seed, a compound of formula: ##STR1## wherein R.sup.1 is hydrogen or alkyl, R.sup.2 is hydrogen, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxyalkyl (e.g. 2-methoxy-ethyl), substituted or unsubstituted aryl or aralkyl or an alkali metal (e.g. sodium or potassium), alkaline earth metal or quaternary ammonium cation, R.sup.3 is halogen, nitro, alkyl, alkyl substituted with up to three halogens (e.g. trichloro- or trifluoro-methyl), cycloalkyl, alkoxy, alkylthio, amino, acylamino (e.g. acetylamino), mono- or di-alkylamino, acyl (e.g. acetyl), haloacyl (e.g. bromoacetyl), cyano, amido, hydroxy, carboxy, alkoxycarbonyl (e.g.Type: GrantFiled: April 25, 1978Date of Patent: October 28, 1980Assignee: Imperial Chemical Industries LimitedInventors: Jeremy J. Batch, Keith P. Parry, Colin F. Rowe, David K. Lawrence, Michael J. Brown
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Patent number: 4224224Abstract: A method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and substituted aryl derivatives thereof is disclosed. The compounds are prepared by treating a 1-(carbocyclic aryl)-2-(2',3'-bis-carboalkoxyguanidino) ethane of the formula ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, R' is phenyl optionally substituted with the radial methylenedioxy or at least one hydroxy, halo, trifluoromethyl, C.sub.1 to C.sub.6 linear or branched alkoxy, or 1-naphthyl or 2-naphthyl and X is halo, mesyloxy or tosyloxy with a protic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide. 1-(Optionally substituted carbocyclic aryl)-2-(carboalkoxyguanidino) ethanes are also disclosed herein, such prepared by treating the above bis-carboalkoxyguanadino ethane with an aprotic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide.Type: GrantFiled: June 21, 1979Date of Patent: September 23, 1980Assignee: Syntex (U.S.A.) Inc.Inventors: Charles A. Dvorak, Colin C. Beard
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Patent number: 4219660Abstract: There are disclosed herein derivatives of bisfunctionalized compounds, wherein said compounds have been formed by the introduction of a nitro group and a hydroxyl group in the form of an ester into a conjugated diene molecule by treatment of said conjugated dienes with nitric acid in the presence of a carboxylic acid anhydride. The novel compounds produced by this process are useful as bactericides, fungicides and valuable organic synthesis intermediates.Type: GrantFiled: June 24, 1977Date of Patent: August 26, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Pius A. Wehrli
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Patent number: 4219661Abstract: This invention relates to an improved process for the production of urethanes (i.e. carbamic acid esters) by reacting organic nitro compounds with carbon monoxide and organic compounds containing at least one hydroxy group in the presence of a unique catalyst system. The catalyst system consists of palladium or a palladium compound and iron oxychloride or a mixture of iron compounds containing iron oxychloride.Type: GrantFiled: April 23, 1979Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventors: Robert Becker, Johann Grolig, Christian Rasp, Gerhard Scharfe
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Patent number: 4214001Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen or cyano;R.sub.2 is fluorine, cyano, trifluoromethyl, nitro or alkyl of 1 to 4 carbon atoms;R.sub.3 is alkoxy of 1 to 5 carbon atoms, alkenyloxy of 2 to 5 carbon atoms, aryloxy of 6 to 10 carbon atoms, aralkoxy of 7 to 11 carbon atoms, or --NR.sub.5 R.sub.6, where R.sub.5 and R.sub.6 are each hydrogen, alkyl of 1 to 5 carbon atoms, alkenyl of 2 to 5 carbon atoms, aryl of 6 to 10 carbon atoms or aralkyl of 7 to 11 carbon atoms; andR.sub.4 is cycloalkyl of 3 to 5 carbon atoms or alkyl of 3 to 5 carbon atoms;and non-toxic, pharmacologically acceptable acid addition salt thereof. The compounds as well as the salts are useful as analgesics, uterospasmolytics and antiasthmatics.Type: GrantFiled: March 6, 1978Date of Patent: July 22, 1980Assignee: Boehringer Ingelheim GmbHInventors: Gunther Engelhardt, Johannes Keck, Kruger, Klaus Noll, Helmut Pieper
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Patent number: 4186269Abstract: An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a catalyst composed of (1) palladium, ruthenium, rhodium or compounds thereof, (2) a Lewis acid, and (3) a tertiary amine. For instance, 2,4-dinitrotoluene, ethanol and carbon monoxide placed in a SUS-32 reactor are interacted in the presence of a catalyst composed of (1) 5% palladium on carbon, (2) ferric chloride, and (3) pyridine to obtain 2,4-diethyldicarbamatetoluene without corrosion of the reactor. After completion of the reaction, the catalyst and reaction product are separated from the reaction system; e.g., the insoluble catalyst is first separated and then the reaction solution is cooled down, e.g., to room temperature, to separate the reaction product as crystals, followed by separation of the crystals by filtration.Type: GrantFiled: December 31, 1975Date of Patent: January 29, 1980Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyate, Makoto Aiga
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Patent number: 4182899Abstract: The present application relates to the optical resolution into optical antipodes of compounds of the formula ##STR1## as well as to salts consisting of an optical isomer of a compound of the above formula and an optical isomer of 2-aminobutanol. The optically active compounds of the above formula are employed as starting materials for the production of semisynthetic antibiotics of the cephalosporin or penicillin type.Type: GrantFiled: August 7, 1978Date of Patent: January 8, 1980Assignee: Hoechst AktiengesellschaftInventors: Yung B. Chae, Dae W. Kim
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Patent number: 4173706Abstract: A novel process for producing fluorinated organic compounds containing a difluoromethylene group, essentially characterized by reacting organic compounds containing a carbonyl function with molybdenum hexafluoride at room temperature and under atmospheric pressure.Type: GrantFiled: April 6, 1978Date of Patent: November 6, 1979Assignee: Institute National de Recherche Chimique AppliqueeInventors: Francois Mathey, Jean Bensoam
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Patent number: 4172204Abstract: A method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and substituted aryl derivatives thereof is disclosed. The compounds are prepared by treating a 1-(carbocyclic aryl)-2-(2',3'-bis-carboalkoxyguanidino) ethane of the formula ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, R' is phenyl optionally substituted with the radical methylenedioxy or at least one hydroxy, halo, trifluoromethyl, C.sub.1 to C.sub.6 linear or branched alkoxy, or 1-naphthyl or 2-naphthyl and X is halo, mesyloxy or tosyloxy with a protic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide. 1-(Optionally substituted carbocyclic aryl)-2-(carboalkoxyguanidino) ethanes are also disclosed herein, such prepared by treating the above bis-carboalkoxyguanadino ethane with an aprotic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide.Type: GrantFiled: October 7, 1977Date of Patent: October 23, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Charles A. Dvorak, Colin C. Beard
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Patent number: 4170708Abstract: Aromatic urethanes are produced by interacting an aromatic nitro compound, an organic compound containing hydroxyl groups and carbon monoxide in the presence of a catalyst composed of elemental selenium or a selenium compound and of a promoter composed of a bicyclic amidine together with a phenolic compound or a carboxylic acid. The interaction proceeds smoothly with the aid of a small amount of the promoter, attended with secondary production of amino compounds only in small amounts. For instance, 2,4-diethyldicarbamatetoluene is obtained at a yield of 87% by interacting 2,4-dinitrotoluene, ethanol and carbon monoxide in the presence of a catalytic system composed of metallic selenium, 1,8-diazabicyclo(5,4,0)-undecene-7 and acetic acid.Type: GrantFiled: March 8, 1976Date of Patent: October 9, 1979Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yutaka Hirai, Katsuharu Miyata, Seiji Hasegawa
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Patent number: 4167489Abstract: Liquid crystalline compounds of the formula: ##STR1## wherein X is an electron-repelling radical and Z is an electron-attracting radical, and rings A, B and C are each unsubstituted or additionally substituted with 1 to 4 identical or different monovalent organic radicals.Type: GrantFiled: March 2, 1978Date of Patent: September 11, 1979Assignee: BBC Brown Boveri & Company, LimitedInventor: Maged A. Osman
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Patent number: 4164583Abstract: The present invention provides benz[f]isoindolines, useful in the treatment of aggression, a process for their preparation and compositions containing these compounds.Type: GrantFiled: June 22, 1978Date of Patent: August 14, 1979Assignee: Sandoz Ltd.Inventors: Roland Achini, Wolfgang Oppolzer, Emil Pfenninger
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Patent number: 4160077Abstract: A process for the cross-linking or chain extension of hycrocarbon polymers which contain ethylenically unsaturated groups which comprises forming an intimate mixture of the polymer with a carbamate of the formula: ##STR1## WHEREIN R.sub.1 is an optionally substituted hydrocarbyl radical, m is an integer, and A is H or an optionally substituted hydrocarbyl radical of valency m, and subjecting the mixture to heat.Novel compounds of preferred use include those in which m=1 and at least one of R and A is alkyl or 7 or more carbon atoms, or in which m=2 and A is phenylene or alkylene or alkenylene of 2 to 4 carbon atoms.Type: GrantFiled: January 6, 1978Date of Patent: July 3, 1979Assignee: Imperial Chemical Industries LimitedInventors: John L. Brooks, Richard Budziarek, David J. Harper
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Patent number: 4146557Abstract: N,N-dichloro-N-acyl compounds, such as N,N-dichlorocarbamates, sulfonamides and amidosulfonamides selectively react with conjugated dienes to yield the corresponding 1,4-adducts, i.e. N-chloro-N-chlorocrotyl compounds. The N-chloro group of these adducts can be selectively reduced by aqueous sodium sulfite. Both the original and the reduced adducts are novel compositions useful as biologically active compounds and vulcanizing agents. The N-chlorocrotyl sulfonamides and their N-chloro derivatives are particularly claimed compositions.Type: GrantFiled: May 21, 1975Date of Patent: March 27, 1979Assignee: Exxon Research & Engineering Co.Inventors: Francis A. Daniher, Alexis A. Oswald
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Patent number: 4134918Abstract: Novel halomethyl derivatives of amines of the following general structure: ##STR1## WHEREIN Y is FCH.sub.2 --, F.sub.2 CH-- or F.sub.3 C--; Z is .beta.-methylthioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, or ##STR2## WHEREIN N IS 2 OR 3 AND R.sub.1 is hydrogen or lower alkyl of from 1 to 4 carbon atoms with the proviso that when R.sub.1 is other than hydrogen, n is 2; and each of R.sub.a and R.sub.b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; with the provisos that when Z is .beta.-benzylthioethyl or S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, R.sub.b is hydrogen, when Z is .beta.-methylthioethyl, Y is other than F.sub.Type: GrantFiled: September 6, 1977Date of Patent: January 16, 1979Assignee: Merrell Toraude et CompagnieInventors: Philippe Bey, Michel Jung
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Patent number: 4130645Abstract: The present invention relates to novel methods for the protection of agricultural crops against plant pathogenic fungi comprising applying to the foliage of said crops a fungicidally effective amount of a compound selected from certain substituted phenylnitramines and certain novel salts of 2,3,5,6-tetrachlorophenylnitramine.The present invention further relates to certain novel substituted phenylnitramine and certain novel salts of 2,3,5,6-tetrachlorophenylnitramine and methods of preparation thereof.Type: GrantFiled: February 21, 1978Date of Patent: December 19, 1978Assignee: American Cyanamid CompanyInventors: Barrington Cross, David H. Dawe
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Patent number: 4097673Abstract: Certain novel carbamates and thiolcarbamates are broad spectrum herbicides, which can be applied to the locus of undesired vegetation either preemergence or postemergence. Typical representatives of this class of compounds are methyl N-(N-cyclohexylcarbamoyl-N',N'-dimethylamidino)-N-methylcarbamate and methyl N-?1-(3-cyclohexyl-1-methylureido)-1-dimethylaminomethylene!carbamate.Type: GrantFiled: October 13, 1976Date of Patent: June 27, 1978Assignee: E. I. Du Pont de Nemours and CompanyInventor: Julius Jakob Fuchs
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Patent number: 4083848Abstract: Novel carbonic acid esters are disclosed which are useful in a process for introducing esterified carboxy-type protective groups on amino and/or imino groups in amino and/or imino group - containing compounds for the temporary protection of said amino and/or imino groups. Additionally, processes for preparing said esters are also disclosed.Type: GrantFiled: January 3, 1977Date of Patent: April 11, 1978Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masumi Itoh, Takashi Kamiya, Daijiro Hagiwara
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Patent number: 4081440Abstract: A penicillin sulfoxide ester is reacted with an N-chloro halogenating agent at a temperature of from about 75.degree. C. to about 135.degree. C. to produce a novel 2-chlorosulfinylazetidin-4-one intermediate. The intermediate can be treated with stannic chloride to produce a 3-exomethylenecepham sulfoxide.Type: GrantFiled: April 2, 1976Date of Patent: March 28, 1978Assignee: Eli Lilly and CompanyInventor: Stjepan Kukolja