Sulfur, Bonded Directly To A Ring, In Same Side Chain As Ester Function Patents (Class 560/17)
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Patent number: 4388475Abstract: Organic sulfoxides having a latent allyl group bound to the sulfur are enzyme inhibitors of the suicide or K.sub.cat type.Type: GrantFiled: May 7, 1980Date of Patent: June 14, 1983Assignee: Merck & Co., Inc.Inventor: Raymond A. Firestone
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Patent number: 4368332Abstract: Novel bicyclo [2,2,1] heptanes and hept-2Z-enes are substituted at the 5-position by a 6-carboxyhex-2-enyl group or a modification thereof, and at the 6-position by an aldoxime or ketoxime group which is O-substituted by an aliphatic hydrocarbon residue, an aromatic residue, or an aliphatic hydrocarbon residue substituted directly or through an oxygen or sulphur atom by an aromatic residue. Such compounds may be prepared by the action of an oximating agent on an intermediate which is substituted at the 6-position by an aldehydic or ketonic carbonyl group. The compounds are of value for use in pharmaceutical compositions particularly in the context of the inhibition of thromboxane activity.Type: GrantFiled: September 3, 1980Date of Patent: January 11, 1983Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 4362891Abstract: An alkanoic acid compound is disclosed of formula: ##STR1## and certain of its physiologically acceptable salts and esters. The alkanoic acid compound and its salts and esters have an unexpectedly greater anti-inflammatory activity than representative members of a broad class of compounds, phenyl alkane derivatives, known to have therapeutic properties. The alkanoic acid compound also has unexpectedly high antipyretic and analgesic activity. The compounds may be formulated in conventional manner as pharmaceutical compositions.The compound may be prepared from 2-[4-(1-hydroxy-2-dimethylethyl)phenyl] propionic acid directly by dehydration or via an ester by dehydration in the presence of an alkanol followed by hydrolysis.Type: GrantFiled: June 17, 1980Date of Patent: December 7, 1982Assignee: Glaxo Group LimitedInventors: Alfredo Guerrato, Michele Perchinunno
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Patent number: 4362887Abstract: Compounds of the formula: ##STR1## wherein R, R' and R.sup.2 are alkyl radicals having 1 to 20 carbon atoms, phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms, aralkyl radicals having 7 to 12 carbon atoms, or cycloalkyl radicals having 5 to 12 carbon atoms; and wherein R.sup.3 is hydrogen or an alkyl radical having from 1 to 4 carbon atoms. These compounds have utility as synergistic stabilizers with phenolic type antioxidants for the stabilization of organic materials such as natural and synthetic polymers, rubbers, lubricants and oils, etc.Type: GrantFiled: April 10, 1981Date of Patent: December 7, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline
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Patent number: 4360688Abstract: Novel compounds are disclosed of the classes: ##STR1## wherein the subscript n is an integer from 3-5, inclusive, R.sub.1 is hydrogen or R.sub.2 ; R.sub.2 and R.sub.3 consist essentially of C.sub.1 -C.sub.6 alkyl and R.sub.2 may be the same as or different from R.sub.3, and wherein Aryl consists essentially of phenyl and phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, and trifluoromethyl;(b) derivatives of furan having the formula ##STR2## wherein R.sub.4 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, and W is either carbonyl or carbinol; and(c) cyclopentenonyl compounds having the formulas ##STR3## wherein R.sub.5 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, P.sub.1 is hydrogen or a protective group, Y is either ##STR4## A new process is disclosed for preparing 1-(methyl)-16,16-(dimethyl)-11-alpha-15-alpha-dihydroxy-9-oxo-2,13,trans, trans-prostadienoate, and congeners thereof, including racemic mixtures.Type: GrantFiled: May 21, 1981Date of Patent: November 23, 1982Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4358409Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.Type: GrantFiled: April 16, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4356187Abstract: Novel esters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN, R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, halogen, alkenyl of 2 to 3 carbon atoms and alkyl of 1 to 3 carbon atoms, Y' is selected from the group consisting of ##STR2## R.sub.4 ' and R.sub.5 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, fluorine, bromine, chlorine and R.sub.4 ' and R.sub.Type: GrantFiled: April 17, 1980Date of Patent: October 26, 1982Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4351950Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.Type: GrantFiled: January 2, 1980Date of Patent: September 28, 1982Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Phenoxyphenylthioalkanecarboxylic acid amides and their use as herbicides and plant growth regulants
Patent number: 4349377Abstract: This invention relates to new phenoxyphenylthioalkanecarboxylic acid derivatives with herbicidal and plant growth-regulating activity of the formula ##STR1## wherein A is hydrogen or C.sub.1 -C.sub.4 alkyl, B is a salt of a carboxylic-acid, an ester, a thioester, an amide or an imidoether thereof, X is hydrogen, halogen, cyano, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, D is hydrogen, halogen, cyano or trifluoromethyl, E is halogen, cyano, nitro or trifluoromethyl and N is 0 or 1.Type: GrantFiled: September 5, 1980Date of Patent: September 14, 1982Assignee: Ciba-Geigy CorporationInventors: Dieter Durr, Otto Rohr, Georg Pissiotas, Beat Bohner -
Patent number: 4344893Abstract: Novel compounds are described which are substituted benzophenone hydrazones. They have pesticidal activity, especially against insects and acarids, and pesticidal compositions and methods are described. Methods of making the compounds, and novel intermediates, are also described.Type: GrantFiled: February 25, 1980Date of Patent: August 17, 1982Assignee: The Boots Company LimitedInventors: Leonard G. Copping, John C. Kerry, Thomas I. Watkins, Robert J. Willis, Bryan H. Palmer
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Patent number: 4342694Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified. The halomethyl bicyclic lactone is a useful intermediate for the preparation of insecticidal cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates or cis-3-(2-halo-2-trihalomethylethenyl)-2,2-dimethylcyclopropanecarboxylates .Type: GrantFiled: June 23, 1980Date of Patent: August 3, 1982Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
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Patent number: 4342705Abstract: Vulcanizable rubber compositions are described which are inhibited from premature vulcanization by activated methylene di(thioethers) in which the adjacent activating groups are either carbonyl or cyano. Novel compounds are also described.Type: GrantFiled: December 1, 1980Date of Patent: August 3, 1982Assignee: Monsanto CompanyInventors: Otto W. Maender, Eiichi Morita
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Patent number: 4332734Abstract: New homopolymerizable or copolymerizable 3,3-disubstituted furan dione compounds are described of the formula ##STR1## wherein X is a reactive moiety and Y and R are unreactive moieties.Type: GrantFiled: December 9, 1980Date of Patent: June 1, 1982Assignee: The Dow Chemical CompanyInventors: Edmund P. Woo, Michael J. Mullins
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Patent number: 4329293Abstract: An improved process is disclosed for sulfenylating carbamates in the presence of a solvent and acid acceptor, in which the reaction between a carbamate and a sulfenyl halide is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide. Several methods for preparing and utilizing the complex in the reaction are disclosed and exemplified.Type: GrantFiled: October 31, 1980Date of Patent: May 11, 1982Assignee: FMC CorporationInventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
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Patent number: 4327025Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.Type: GrantFiled: April 7, 1980Date of Patent: April 27, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
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Patent number: 4325873Abstract: A process for the preparation of a styryl-cyclopropane-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine, comprising reacting a compound of the formula ##STR2## with, respectively, one, two or three equivalents of a base at a temperature below 60.degree. C. The products are insecticidally active when R is the residue of a pyrethroid-type alcohol. Various syntheses are given for the starting materials which are new.Type: GrantFiled: April 7, 1980Date of Patent: April 20, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
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Patent number: 4323691Abstract: Described are compounds of the formula ##STR1## wherein ##STR2## wherein Z is hydrogen or loweralkyl, R.sub.5 and R.sub.6 may be the same or different and are hydrogen, loweralkyl or together are alkylene of 4 or 5 carbon atoms,R.sub.2 is hydrogen, halo, haloloweralkyl, loweralkyl, loweralkoxy, loweralkylthio or ##STR3## wherein R.sub.5 and R.sub.6 are previously defined, R.sub.3 is hydroxy, alkoxy, branched alkoxy, adamantyloxy, morpholino, amino or amino substituted by loweralkyl or alkylene of 4 or 5 carbon atoms,R.sub.4 is hydrogen or loweralkyl, andX.sub.1 and X.sub.2 are hydrogen, loweralkyl, halo or when substituted on adjacent carbon atoms of the benzene ring form a 1,3-butadienylene linkage, Y is oxygen or sulfur, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents in increasing urinary excretion.Type: GrantFiled: December 1, 1980Date of Patent: April 6, 1982Assignee: Abbott LaboratoriesInventors: Carroll W. Ours, Cheuk M. Lee
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Patent number: 4315026Abstract: A novel class of chemical compounds useful as pesticides consists of alkylpolyoxysulfinyl and alkylpolythiosulfinyl derivatives of carbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.Type: GrantFiled: April 11, 1980Date of Patent: February 9, 1982Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto, Teruomi Jojima
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Patent number: 4311637Abstract: There is disclosed polyphenolic mercaptophenol type antioxidants, a method of preparing the antioxidants and to polymer compositions containing such polyphenolic mercaptophenol type antioxidants. In particular, polyphenolic antioxidants such as 2-(2-hydroxy-3-tertiary-butyl-5-methylbenzyl)-4-methyl-6-tertiary butyl phenyl 3-(4-hydroxyphenylthio)propionate.Type: GrantFiled: February 8, 1980Date of Patent: January 19, 1982Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4310512Abstract: Compounds of the formula ##STR1## wherein A, B, C individually represent hydrogen or an alkyl group of 1 to 6 carbon atoms, provided that the total combined number of carbon atoms of A, B and C does not exceed 8;X represents oxygen, sulfur, ##STR2## wherein the alkyl group has 1 to 7 carbon atoms or ##STR3## wherein R and R' represent hydrogen or a methyl group; n represents 1 or 2; andZ represents a hydroxyalkyl group of 2 to 7 carbon atomshave been found to be useful in compositions and methods for counteracting malodors.Type: GrantFiled: December 4, 1979Date of Patent: January 12, 1982Assignee: Bush Boake Allen Inc.Inventor: Alfred A. Schleppnik
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Patent number: 4307031Abstract: A method for producing a mixture of a dithiodibenzoate, a dithiocarbonate, and a trithiocarbonate, is disclosed. The method includes diazotizing an amine having the formula ##STR1## where R is hydrogen, or an alkyl group having not more than 4 carbon atoms, and coupling the resulting diazonium with at least 1 gram-mole of carbon disulfide per gram-mole of the diazonium in the presence of a copper catalyst. Under appropriate conditions, which include a reaction temperature in the range of 10.degree.-32.degree. C., sufficient time for full coupling to occur, and dissolving of the CS.sub.2 in a suitable water-miscible solvent such as methanol, coupling to said mixture readily occurs. The coupling products are then dissolved and removed by use of a water-immiscible inert solvent.Type: GrantFiled: May 19, 1980Date of Patent: December 22, 1981Assignee: The Sherwin-Williams CompanyInventor: Lubomir Vacek
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Patent number: 4304728Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.Type: GrantFiled: March 27, 1980Date of Patent: December 8, 1981Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4302366Abstract: The present invention relates to new fluorinated products resulting from the reaction of:(a) one molecule of one or more acids of the formula:HS - A (COOH).sub.n (I)and of(b) one to five molecules of one or more compounds possessing at least one ethylenic bond, at least one of these compounds corresponding to the general formula: ##STR1## and possibly neutralized or partially neutralized with an inorganic or organic base.In the formulae (I) and (II), A represents an aliphatic or aromatic hydrocarbon radical, n is a whole number from 1 to 4, Rf represents a straight or branched perfluorinated chain containing 1 to 20 carbon atoms, B represents bivalent, possibly branched, chaining and may comprise sulfur, oxygen or nitrogen atoms, one of the symbols R represents a hydrogen atom and the other a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms.Type: GrantFiled: November 1, 1979Date of Patent: November 24, 1981Assignee: Produits Chimiques Ugine KuhlmannInventors: Jean Perronin, Andre L. Dessaint
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Patent number: 4301296Abstract: Ester such as 3,6,9-trioxaundecane-1,11-bis(3-n-dodecylthiopropionate) when combined with conventional free amine antioxidants such as N,N'-diphenylparaphenylenediamine or with polymer bound antioxidants such as N-(4-anilinophenyl) methacrylamide produce improved antioxidant systems for SBR and NBR type polymers.Type: GrantFiled: September 29, 1980Date of Patent: November 17, 1981Assignee: The Goodyear Tire & Rubber CompanyInventor: Joseph A. Kuczkowski
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Patent number: 4295976Abstract: New fluorinated telomerization products are disclosed which are products produced by the reaction of:a. one mole of an ester of one or more acids of the formulaHS-A(COOH).sub.n (I)with one or more polyols, andb. 1 to 5 moles of one or more compounds possessing at least one ethylenic bond, one at least of these compounds conforming to the general formula ##STR1## In formulae (I) and (II), A represents a hydrocarbon radical which may contain atoms of oxygen, nitrogen, phosphorus, sulphur or halogen, n is a whole number from 1 to 4, Rf is a perfluorinated chain containing 1 to 20 carbon atoms, B is a bivalent chain, one of the symbols R represents a hydrogen atom and the other a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms. These products when applied to substrates, such as textile fabrics, confer on them a permanent anti-stain and soil release finish while permitting easy elimination of soil by washing.Type: GrantFiled: September 28, 1976Date of Patent: October 20, 1981Assignee: Produits Chimiques Ugine KuhlmannInventors: Andre L. Dessaint, Jean Perronin
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Patent number: 4296128Abstract: New carboxylic acid hydrazides of the formula ##STR1## in which R represents an optionally esterified carboxy group,and salts of the compound of the formula I, in which R represents carboxy, possess antithrombotic properties and can be used as medicinal active substances in pharmaceutical preparations.Type: GrantFiled: May 7, 1980Date of Patent: October 20, 1981Assignee: Ciba-Geigy CorporationInventors: Alfred Sallmann, Richard Goschke
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Patent number: 4277624Abstract: Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above, by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:RYH (III)wherein R and Y have the same meanings as defined above, respectively. The latter diphenyl ether compounds of the general formula (II) are useful as herbicides.Type: GrantFiled: July 5, 1979Date of Patent: July 7, 1981Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Takeo Yoshimoto, Keiichi Igarashi, Kengo Oda, Masaaki Ura, Naoki Sato
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Patent number: 4271050Abstract: Vulcanizable rubber compositions are described which are inhibited from premature vulcanization by activated methylene di(thioethers) in which the adjacent activating groups are either carbonyl or cyano. Novel compounds are also described.Type: GrantFiled: November 23, 1979Date of Patent: June 2, 1981Assignee: Monsanto CompanyInventors: Otto W. Maender, Eiichi Morita
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Patent number: 4262015Abstract: A novel class of chemical compounds useful as pesticides consists of N-alkylthio- and N-arylthiosulfinylcarbamate esters. The preparation of these compounds and their formulation to control insects are exemplified.Type: GrantFiled: March 7, 1979Date of Patent: April 14, 1981Assignee: The Regents of the University of CaliforniaInventors: Mohamed A. H. Fahmy, Tetsuo R. Fukuto
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Patent number: 4261924Abstract: New 4-nitro-2-trichloromethylphenylsulfenamides having a fungicidal and bactericidal action, processes for their manufacture, fungicides containing these compounds as active ingredients, and a process for combating fungi with these compounds.Type: GrantFiled: September 25, 1979Date of Patent: April 14, 1981Assignee: BASF AktiengesellschaftInventors: Helmut Hagen, Ernst-Heinrich Pommer, Wolfgang Reuther, Hans Ziegler
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Patent number: 4256761Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycyclo-alkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, dialkylamino-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, or fused heteroaryl-cycloalkyl-alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hyroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.Type: GrantFiled: July 13, 1979Date of Patent: March 17, 1981Assignee: USV Pharmaceutical CorporationInventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
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Patent number: 4254020Abstract: Compounds of the formula: ##STR1## wherein R is selected from (1) alkyl radicals having 6 to 20 carbon atoms; (2) phenyl radicals which may be substituted by 1 or 2 alkyl groups having 1 to 8 carbon atoms; or (3) aralkyl radicals having 7 to 12 carbon atoms; and wherein R.sup.1 is selected from (1) alkylene radicals having 2 to 6 carbon atoms; (2) cycloalkylene radicals having 5 to 12 carbon atoms; (3) alkylcycloalkylene radicals of the formula --R.sub.3 --R.sub.2 (R.sub.4).sub.n, wherein R.sub.2 is a cycloalkylene radical having 5 to 12 carbon and R.sub.3 and R.sub.4 are alkylene radicals having 1 to 6 carbon atoms, and n equals 1 or 0; (4) or a group of the formula --R.sub.5 --YR.sub.6, wherein R.sub.5 and R.sub.6 are alkylene radicals having 2 to 6 carbon atoms and Y is oxygen, sulfur, or a 1,4-phenylene radical.Type: GrantFiled: November 16, 1979Date of Patent: March 3, 1981Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline
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Patent number: 4241217Abstract: Ester such as 3,6,9-trioxaundecane-1,11-bis (3-n-dodecylthiopropionate) when combined with conventional free amine antioxidants such as N,N'-diphenylparaphenylenediamine or with polymer bound antioxidants such as N-(4-anilinophenyl) methacrylamide produce improved antioxidant systems for SBR and NBR type polymers.Type: GrantFiled: May 26, 1978Date of Patent: December 23, 1980Assignee: The Goodyear Tire & Rubber CompanyInventor: Joseph A. Kuczkowski
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Patent number: 4238397Abstract: Hydroxyl-terminated liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one vinylidene monomer having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide. Use of the above disulfide-trisulfide mixture permits viscosity control during polymerization with substantially less disulfide required than if the disulfide alone were used, and the resulting polymers have less odor and discolor less upon heating than if the disulfide alone were used.Type: GrantFiled: May 18, 1979Date of Patent: December 9, 1980Assignee: The B. F. Goodrich CompanyInventor: Jack C. Gilles
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Patent number: 4235780Abstract: Processes for producing a (1.alpha., 4.alpha., 5.alpha.)-6,6-dimethyl-4-halo-substituted-methyl-3-oxabicyclo[3.1.0]hexan- 2-one and its novel intermediates from known and inexpensive starting materials are described and exemplified.Type: GrantFiled: November 1, 1979Date of Patent: November 25, 1980Assignee: FMC CorporationInventors: Kiyoshi Kondo, Toshiyuki Takashima, Minoru Suda
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Patent number: 4235926Abstract: Compounds of the general formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, butoxy, tetrafluoroethoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, or nitro group, and R.sup.2 is hydrogen or a methyl group, or R.sup.1 and R.sup.2 together form a methylenedioxy group;R.sup.3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (f):(a) 3-phenoxybenzyl(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-3-phenoxybenzyl(d) 3,4-methylenedioxybenzyl(e) .alpha.-ethynyl-3-phenoxybenzyl(f) .alpha.-cyano-3-(4'-chlorophenoxy)-benzyland Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5 and Y.sup.6 are the same or different groups and each is hydrogen or a fluoro, bromo or chloro group, with the proviso that when R.sup.1 is hydrogen, fluoro, chloro, bromo or methyl and R.sup.2 is hydrogen, then one of Y.sup.1 to Y.sup.6 is other than hydrogen.The compounds in which R.sup.3 is one of groups (a) to (f) are insecticides.Type: GrantFiled: December 15, 1978Date of Patent: November 25, 1980Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, David F. O'Keefe
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Patent number: 4233054Abstract: New phenoxy-alkanecarboxylic acid derivatives which have a herbicidal action and which are effective in regulating plant growth are described. They correspond to the formula ##STR1## in which A is the cyano group, a carboxylic acid, a salt, ester, thioester or amide thereof,Q is a mono- to trisubstituted phenyl or pyrid-2-yl radical,R.sub.3 is hydrogen, halogen, cyano, nitro, alkyl or carbamoyl,R.sub.4 is alkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzyl, andX, Y and Z are each oxygen or sulfur.They can be used as selective herbicides in cereal and rice crops, or for reducing the vegetative growth, for example in soya-bean crops, and also for defoliation and desiccation in cotton or potato crops shortly before the harvesting thereof.Type: GrantFiled: March 12, 1979Date of Patent: November 11, 1980Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Otto Rohr, Georg Pissiotas, Beat Bohner, Hermann Rempfler
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Patent number: 4230857Abstract: Carbonates and urethanes of 2,2'-alkylene or -cycloalkylene-bis-4,6-disubstituted phenols are useful for stabilizing organic materials against the degradative effects of oxygen.Type: GrantFiled: May 23, 1978Date of Patent: October 28, 1980Assignee: Sandoz Ltd.Inventors: William O. Drake, Hans Hinsken, Horst Mayerhoefer, Wolfgang H. Mueller
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Patent number: 4228029Abstract: Liquid crystalline compositions, especially for displays with a twisted nematic phase, comprising at least one compound of the formula ##STR1## wherein X=H, --CHO or --CH.sub.3, R.sup.1 =C.sub.1 --C.sub.10 alkyl, R.sup.2 is a monovalent organic group, for example, --CN; and Y is a single bond or one of the groups --COO-- or ##STR2## The compositions show a high positive dielectric anisotropy (.DELTA..epsilon.), a high .DELTA.n, and a low viscosity, and the mixture system may comprise relatively few components.Type: GrantFiled: January 24, 1979Date of Patent: October 14, 1980Assignee: BBC Brown Boveri & Company LimitedInventor: Maged A. Osman
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Patent number: 4225533Abstract: Novel esters of ether and thioether substituted cyclopropanecarboxylic acids, synthesis thereof, and intermediates therefor, such esters being useful as pesticides.Type: GrantFiled: June 1, 1979Date of Patent: September 30, 1980Assignee: Zoecon CorporationInventor: Clive A. Henrick
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Patent number: 4223155Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an optionally halo-substituted hydrocarbyl group, and X is --C(O)Cl, --C(O)Br or C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the neutral terpene, 3-carene.Type: GrantFiled: July 26, 1979Date of Patent: September 16, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4219562Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an optionally halo-substituted hydroxcarbyl group, and X is --C(O)Cl, --C(O)Br or C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 8, 1979Date of Patent: August 26, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4215139Abstract: Carbamic acid derivatives, processes for their preparation, as well as pesticidal compositions containing the carbamic acid derivatives, and methods for their use, are disclosed.Type: GrantFiled: March 6, 1979Date of Patent: July 29, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Ulf Fischer, Fernand Schneider, Rene Zurflueh
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Patent number: 4208326Abstract: This invention relates to new pleuromutilins of the formula: ##STR1## wherein either R.sub.1 is ethyl or vinyl,n is an integer from 2 to 5,X is sulphur,a group ##STR2## or a group .dbd.N--R.sub.4.sup.I, whereineither Y and Z are both sulphur, orone of Y and Z is oxygen and the other is sulphur, andR.sub.4.sup.I is hydrogen or a group of the formula: ##STR3## wherein R.sub.1 is as defined above, each of R.sub.2 and R.sub.3 is alkyl of 1 to 10 carbon atoms, orR.sub.2 and R.sub.3 together with the nitrogen atom form a heterocycle of 5 to 7 ring members, and pharmaceutically acceptable acid addition salts and quaternary salts thereof.Processes for the preparation of such compounds are described.The compounds are antibiotics with an antibacterial effect.Type: GrantFiled: June 5, 1978Date of Patent: June 17, 1980Assignee: Sandoz Ltd.Inventors: Helmut Egger, Hellmuth Reinshagen
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Patent number: 4207238Abstract: Hydroxyl-terminated liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one vinylidene monomer having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) a mixture of at least one hydroxyl-containing disulfide and at least one hydroxyl-containing trisulfide. Use of the above disulfide-trisulfide mixture permits viscosity control during polymerization with substantially less disulfide required than if the disulfide alone were used, and the resulting polymers have less odor and discolor less upon heating than if the disulfide alone were used.Type: GrantFiled: September 1, 1977Date of Patent: June 10, 1980Assignee: The B. F. Goodrich CompanyInventor: Jack C. Gilles
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Patent number: 4207329Abstract: Novel derivatives of glycolic and glyoxylic acid are disclosed which inhibit glycolic acid oxidase and thus are useful in the treatment and prevention of calcium oxalate urolithiasis (calcium oxalate kidney and bladder stone disease).Type: GrantFiled: October 11, 1978Date of Patent: June 10, 1980Assignee: Merck & Co., Inc.Inventors: Haydn W. R. Williams, Edward J. Cragoe, Jr., Clarence S. Rooney
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Patent number: 4200760Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a straight or branched chain alkynyl group containing from 3 to 9 carbon atoms, inclusive; R.sup.2 is hydrogen, (lower)alkyl, halogen or hydroxymethyl; m is 1 or 2, and n is 2 or 3, provided that the sum of m and n is 3 or 4; X and Y each are independently hydrogen, nitro, cyano, --SO.sub.2 Ar or --COR.sup.3, provided that X and Y are not both hydrogen; R.sup.3 is (lower)alkyl, Ar, (lower)alkoxy, amino or (lower)-alkylamino; and Ar is an optionally substituted phenyl group; and nontoxic pharmaceutically acceptable acid addition salts thereof, are potent anti-ulcer agents. Processes for their preparation and novel intermediates are also disclosed.Type: GrantFiled: September 26, 1978Date of Patent: April 29, 1980Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4199597Abstract: Omega-[4-(polyfluoro-2-hydroxy-2-propyl)-2,3,6-substituted-phenoxy and phenylthio]alkanoic acids and compounds related thereto having antihypertensive activity are preparable by reaction of the appropriate 2,3,6-substituted-4-(polyfluoro-2-hydroxy-2-propyl)phenol or thiophenol with an alkyl ester of a bromoalkanoic acid, followed by hydrolysis to the free acid.Type: GrantFiled: May 4, 1979Date of Patent: April 22, 1980Assignee: Schering CorporationInventors: Bernard R. Neustadt, Elijah H. Gold
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Patent number: 4198527Abstract: Novel esters of ether and thioether substituted cyclopropanecarboxylic acids, synthesis thereof, and intermediates therefor, such esters being useful as pesticides.Type: GrantFiled: September 15, 1978Date of Patent: April 15, 1980Assignee: Zoecon CorporationInventor: Clive A. Henrick
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Patent number: RE30578Abstract: New N-arylcarbamic acid esters of the formula ##STR1## in which R is lower aliphatic hydrocarbyl, optionally substituted,R.sup.1, R.sup.2 and R.sup.3, which may be identical or different, are each hydrogen, alkyl, cycloalkyl, alkoxy, haloalkyl or halogen,R.sup.4 is alkyl, alkenyl, cycloalkenyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl or alkylthioalkyl, acylalkyl (i.e., alkanoyloxyalkyl), alkoxycarbonylalkyl, carbalkoxyalkyl, carbalkoxyalkenyl, or an optionally substituted cycloalkyl, aryl, aralkyl, aryloxyalkyl or arylthioalkyl radical, or the grouping ##STR2## wherein R.sup.4' is hydrogen or is defined as R.sup.4 is defined above, andY and Y' are oxygen or sulfur,are outstandingly effective in regulating the growth of plants, i.e., to inhibit, stimulate or alter the growth of plants.Type: GrantFiled: November 22, 1977Date of Patent: April 14, 1981Assignee: Bayer AktiengesellschaftInventors: Carl Metzger, Gerhard Jager, Klaus Lurssen