Sulfur In Acid Moiety Patents (Class 560/9)
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Patent number: 4389416Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo; R.sub.1 is carboxy, carboxyloweralkyl, aminocarbonyl, hydroxymethyl, anilinomethyl, or aminomethyl; A is oxygen, CH.sub.2, Sulfur or a single bond; X is oxygen, CH.sub.2, sulfur or sulfoxide; and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof.The compounds are effective as diuretic agents.Type: GrantFiled: October 9, 1981Date of Patent: June 21, 1983Assignee: Abbott LaboratoriesInventor: Jacob J. Plattner
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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: 4386031Abstract: The present invention refers to N-Benzoyl-.omega.Type: GrantFiled: November 6, 1981Date of Patent: May 31, 1983Assignee: A. Nattermann & Cie GmbHInventors: Gerd Hilboll, Hans-Heiner Lautenschlager, Brigitte Stoll, Manfred Probst
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Patent number: 4382954Abstract: Compounds represented by the formula ##STR1## wherein R and R.sup.1 are independently hydrogen or lower alkyl; R.sup.2 is lower alkenyl, lower alkynyl or --CH.sub.2 X wherein X is halogen, hydroxyl, lower alkoxy, lower alkylthio or a furanyl ring; and Z is hydroxyl, lower alkoxy or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl possess fungicidal activity. Moreover, some of the compounds of this invention also possess herbicidal activity.Type: GrantFiled: January 27, 1982Date of Patent: May 10, 1983Assignee: Chevron Research CompanyInventor: David C. K. Chan
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Patent number: 4381403Abstract: A process for the preparation of N-monosubstituted carbamic acid esters by reacting an unsubstituted carbamic acid ester and an aromatic primary amine at a suitable pressure and reaction temperature in the presence of a monohydric aliphatic alcohol and preferably in the presence of a strongly basic tertiary amine as catalyst. Optionally an inert co-solvent in addition to the alcohol may be employed.Type: GrantFiled: March 31, 1980Date of Patent: April 26, 1983Assignee: Atlantic Richfield CompanyInventors: Samuel J. Falcone, John J. McCoy
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Patent number: 4378318Abstract: Herbicidal compositions comprising or consisting of a compound of the formula ##STR1## in which R is an aliphatic, straight chain, branched or cyclic, saturated or unsaturated hydrocarbon residue of 1 to 6 carbons, R.sub.1 is hydrogen or methyl, R.sub.2 is cyanoalkyl or alkoxyalkyl, R.sub.3 is the same or different if more than one and is hydrogen, alkyl, alkoxy, alkylthio or halogen and n is 1 or 2. The compounds have a broad soil and leaf herbicidal effect and are suited particularly for selective weed suppression in cultures like soybeans, peas, alfalfa, potatoes, maize, sorghum, rice, wheat and barley.Type: GrantFiled: July 15, 1981Date of Patent: March 29, 1983Assignee: Schering AktiengesellschaftInventors: Ludwig Nusslein, Friedrich Arndt
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Patent number: 4376784Abstract: 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: March 24, 1981Date of Patent: March 15, 1983Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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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: 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: 4364875Abstract: The method of preparing a compound of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl of 1 to 8 carbon atoms, trifluoromethyl or acetyl;n is 1 when R.sub.1 has all the defined meanings, or 2 or 3 when R.sub.1 is halogen or alkyl;R.sub.2 is hydrogen; alkyl of 1 to 16 carbon atoms; alkenyl of 2 to 16 carbon atoms; alkinyl of 2 to 16 carbon atoms; monosubstituted alkyl of 2 to 6 carbon atoms, where the substituent is hydroxyl, alkoxy of 1 to 4 carbon atoms, phenoxy, halo-phenoxy, (alkyl of 1 to 4 carbon atoms) phenoxy, (alkoxy of 1 to 4 carbon atoms)phenoxy, nitro-phenoxy, cyano-phenoxy, amino or (alkyl of 1 to 4 carbon atoms)thio; benzyl; halo-benzyl; --NR.sub.3 R.sub.4 ; --CHR.sub.3 --COOR.sub.4 ; or --CHR.sub.3 --CONR.sub.4 R.sub.5, whereR.sub.3, R.sub.4 and R.sub.5 are each hydrogen or alkyl of 1 to 8 carbon atoms; andX.sub.1 and X.sub.2 are each hydrogen or halogen,which comprises reacting a compound of the formula ##STR2## wherein n, R.sub.1, X.sub.1 and X.sub.Type: GrantFiled: July 7, 1981Date of Patent: December 21, 1982Assignee: Celamerck GmbH & Co. KGInventors: Richard Sehring, Wolfgang Buck
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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: 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: 4358606Abstract: Novel esters of phenylalkyloxy- or phenylalkylthioacylamino acids and pyridylalkyloxy- or pyridylalkylthioacylamino acids, synthesis thereof, intermediates therefor, and the use of said esters for the control of weeds.Type: GrantFiled: June 19, 1981Date of Patent: November 9, 1982Assignee: Zoecon CorporationInventors: Shy-Fuh Lee, Clive A. Henrick
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Patent number: 4358308Abstract: The 4-perfluoroacetyl-, 4-perfluoromethylthio-, 4-perfluoromethylsulfinyl-, and 4-perfluoromethylsulfonyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: October 19, 1981Date of Patent: November 9, 1982Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4353834Abstract: Biodegradable non-ionic surface-active agents containing carbonate groups can be prepared by reacting hydrophilic polyoxyalkylene glycols derived from the same or different alkylene oxides with hydrophobic amides or sulfonamides. The compositions of the invention contain both hydrophilic and hydrophobic groups in the molecule making them suitable for use as surface-active agents.Type: GrantFiled: March 13, 1981Date of Patent: October 12, 1982Assignee: BASF Wyandotte CorporationInventor: William K. Langdon
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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: 4348406Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.Type: GrantFiled: October 20, 1980Date of Patent: September 7, 1982Assignee: Schering CorporationInventor: M. Mehdi Nafissi-Varchei
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Patent number: 4344962Abstract: A sulphenylated acylurethane of the formula ##STR1## wherein R.sup.1 denotes hydrogen, halogen, nitro, alkyl, alkoxy or halogenomethyl,R.sup.2 denotes alkyl, alkenyl, alkinyl, cycloalkyl or aralkyl andX.sup.1, X.sup.2 and X.sup.3 are identical or different and denote halogen; a process for its preparation by contacting an isocyanate of the formula ##STR2## wherein R.sup.1, X.sup.1, X.sup.2 and X.sup.3 have the abovemeaning with a hydroxy compound of the formulaR.sup.2 -OH (IV)whereinR.sup.2 has the abovemeaning in the presence of a diluent.The novel sulphenylated acylurethanes are useful as microbicidal agents to protect industrial materials against degradation.Type: GrantFiled: September 8, 1980Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Engelbert Kuhle, Wilfried Paulus, Hermann Genth, Wilhelm Brandes
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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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: 4337353Abstract: Novel carboxylic acids of the formula ##STR1## wherein Z is an aliphatic hydrocarbon chain selected from the group consisting of --(CH.sub.2).sub.n -- and --CH.dbd.CH--(CH.sub.2).sub.n-2 -- where the double bond may be at any point in the chain, n is an integer from 5 to 10 and X, X.sub.1, X.sub.2 and X.sub.3 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 5 carbon atoms, alkylthio of 1 to 5 carbon atoms, CF.sub.3 --, CF.sub.3 O-- and CF.sub.3 S-- and their non-toxic, pharmaceutically acceptable organic and inorganic salts and esters having analgesic and anti-inflammatory activity and their preparation.Type: GrantFiled: February 6, 1978Date of Patent: June 29, 1982Assignee: Roussel UCLAFInventors: Andre Allais, Francois Clemence, Jean Meier, Roger Deraedt
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Patent number: 4336062Abstract: Novel compounds having the formula ##STR1## in which X is (H).sub.2 or (CH.sub.3).sub.2 ; Y is oxygen or sulfur; R.sub.1 is alkyl, lower alkenyl, cyclopropyl, lower alkoxy, thio-lower alkyl or ##STR2## R.sub.2 and R.sub.3 are independently hydrogen, lower alkyl, lower alkenyl, or lower alkoxy and n is 0 or 1. The compounds have been found to possess herbicidal activity.Type: GrantFiled: May 16, 1978Date of Patent: June 22, 1982Assignee: Stauffer Chemical CompanyInventor: Raymond A. Felix
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Patent number: 4331674Abstract: 4-Phenoxy-4-(azolyl-1-yl)-butanoic acid derivatives of the formula ##STR1## in which A is --CO-- or CH(OH)--,Y is --CH.dbd. or --N.dbd.,Z is halogen, alkyl, alkenyl, halogenoalkyl, cycloalkyl, alkoxy, alkylthio, alkoxycarbonyl, phenyl, phenoxy, phenylalkyl, substituted phenyl, phenoxy or phenylalkyl, amino, cyano or nitro,R is cyano, --CO--OR.sup.3 or --CO--NR.sup.4 R.sup.5,R.sup.1 and R.sup.2 each independently is alkyl, phenyl or substituted phenyl, or conjointly form a carbocyclic ring,R.sup.3 is alkyl,R.sup.4 is hydrogen, alkyl, phenyl or substituted phenyl andR.sup.5 is hydrogen or alkyl, orR.sup.4 and R.sup.5 conjointly form a methylene bridge --(CH.sub.2).sub.m -- which can contain a further hetero-atom,m is 2, 3, 4, 5, 6 or 7,n is 0, 1, 2, 3, 4 or 5,and salts thereof, which possess fungicidal properties.Type: GrantFiled: July 27, 1977Date of Patent: May 25, 1982Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Jorg Stetter, Karl H. Buchel, Paul-Ernst Frohberger, Wilhelm Brandes
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Patent number: 4324799Abstract: The present invention relates to new thioglycolic acid anilides of the formula I ##STR1## R.sup.1 denotes (C.sub.1 -C.sub.4)alkyl, halogen, (C.sub.1 -C.sub.3)alkylthio, (C.sub.1 -C.sub.4)alkoxy or (C.sub.3 -C.sub.4)alkenyl,R.sup.2 denotes hydrogen, (C.sub.1 -C.sub.4) alkyl or halogen,R.sup.3, R.sup.4 and R.sup.6 denote hydrogen or methyl,R.sup.5 denotes hydroxy, (C.sub.1 -C.sub.4)alkoxy, (C.sub.1 -C.sub.3)alkylthio, (C.sub.1 -C.sub.2)alkoxy -(C.sub.1 -C.sub.2)alkoxy, amino, (C.sub.1 -C.sub.2)alkylamino or di(C.sub.1 -C.sub.2)alkylamino,Y represents oxygen or sulfur,R.sup.7 represents optionally substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.3 -C.sub.4)alkenyl or (C.sub.3 -C.sub.4)alkinyl,R.sup.8 represents hydrogen or (C.sub.1 -C.sub.4)alkyl,R.sup.9 denotes optionally substituted (C.sub.1 -C.sub.4)alkyl, (C.sub.3 -C.sub.4)alkenyl, furfuryl, tetrahydrofurfuryl, with the proviso that if Y=S, the radicals R.sup.8 and R.sup.9 do not both denote (C.sub.1 -C.sub.4)alkyl,R.sup.Type: GrantFiled: July 23, 1980Date of Patent: April 13, 1982Assignee: Hoechst AktiengesellschaftInventors: Manfred Koch, Hilmar Mildenberger, Burkhard Sachse
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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: 4321275Abstract: The disclosure relates to novel 17,18,19,20-tetranor-prostanoic acid derivatives having prostaglandin-type properties, to a method for their manufacture, and also to pharmaceutical or veterinary compositions containing said novel derivatives and a method of inducing luteolysis in an animal host by use of said novel derivatives.Type: GrantFiled: May 30, 1974Date of Patent: March 23, 1982Assignee: Imperial Chemical Industries LimitedInventors: Jean Bowler, Neville S. Crossley
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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: 4313957Abstract: The invention relates to sulphur-containing products with an amide group, which are derived from aniline.These compounds have the formula: ##STR1## They are used as anti-fungal agents.Type: GrantFiled: January 23, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc AgrochimieInventors: Jean Abblard, Guy Lacroix
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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: 4311514Abstract: The sulfur-containing alkanecarboxylic acids of the formula ##STR1## possess herbicidal and plant growth-regulating properties. In this formula, A is the cyano group, the carboxyl group, a carboxylic acid salt or a carboxylic acid ester, thioester, or carboxamide radical, n is O, 1 or 2, Q is a substituted phenyl or pyrid-2-yl radical, R.sub.3 is a halogen atom, cyano, or nitro group, R.sub.4 is C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, phenyl or benzyl, C.sub.2 -C.sub.6 alkoxyalkyl or C.sub.3 -C.sub.12 cycloalkyl.Type: GrantFiled: September 2, 1980Date of Patent: January 19, 1982Assignee: Ciba-Geigy CorporationInventors: Henry Szczepanski, Otto Rohr, Hermann Rempfler
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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: 4309441Abstract: 13-Thiaprostanoic acid derivatives of the general formula I ##STR1## wherein A is --CO-- or --CHOH--; B is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--; Q is 1,4-phenylene or 1,4-naphthylene; R.sup.1 is H or OH; R.sup.2 is H or CH.sub.3 ; R.sup.3 is alkyl with 1-8 carbon atoms or alkyl with 1-8 carbon atoms substituted by (a) phenyl, (b) phenyl substituted by at least one of CH.sub.3, F, Cl, Br, OH, OCH.sub.3 or CF.sub.3 ; (c) phenoxy or (d) phenoxy substituted by at least one of CH.sub.3, F, Cl, Br, OH, OCH.sub.3 or CF.sub.3 ; and R.sup.4 is NH.sub.2, CH.sub.3, phenyl, p-acetylaminophenyl, p-benzoylaminophenyl or phenylamino. These compounds are useful for lowering blood pressure as well as for other pharmaceutical purposes. They also are useful intermediates for the preparation of other known pharmaceuticals such s the 13-thiaprostaglandins.Type: GrantFiled: November 21, 1979Date of Patent: January 5, 1982Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Hans-Eckart Radunz, Dieter Orth, Manfred Baumgarth, Hans-Jochen Schliep, Hans-Joachim Enenkel
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Patent number: 4309350Abstract: The (+), (-) and (.+-.) forms of the compounds of formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, nitro or amino group, andR.sup.2 is a hydrogen or 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 (d):(a) m-phenoxybenzyl,(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-m-phenoxybenzyl(d) 3-4-methylenedioxy-benzyl,and R.sup.4 and R.sup.5 are the same or different groups and each is a fluoro, bromo, chloro or methyl group.The compounds of formula I in which R.sup.3 is one of groups (a) to (d) are extremely active as insecticides (except when R.sup.1 is an amino group). The compounds also possess the property of contact repellency to insects.Type: GrantFiled: January 24, 1980Date of Patent: January 5, 1982Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, Reimund Walser
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Patent number: 4309439Abstract: A novel substituted-arylacetic acid ester of the formula, ##STR1## wherein R.sub.1 and R.sub.2 are each hydrogen or a halogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxy, cyano, nitro, methylthio, C.sub.1 -C.sub.4 alkanoyl, C.sub.1 -C.sub.4 alkanoyloxy, or C.sub.1 -C.sub.4 alkoxycarbonyl group, or R.sub.1 and R.sub.2, taken together, may form methylenedioxy, a C.sub.3 -C.sub.5 alkylene or butadienylene (--CH.dbd.CH--CH.dbd.CH--) ring; R.sub.3 is a C.sub.2 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, propargyl, C.sub.3 -C.sub.6 cycloalkyl or cyclopropylmethyl group; R.sub.4 is hydrogen or a halogen atom, methyl or ethyl group; R.sub.5 is allyl, propargyl, 3-butenyl, 3-butynyl, phenyl or benzyl group; and A is oxygen or sulfur atom or --CH.dbd.CH-- group, which possesses various useful insecticidal and acaricidal activities and can be prepared by reacting a substituted-arylacetic acid of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.Type: GrantFiled: February 28, 1978Date of Patent: January 5, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuo Ohno, Isao Ohno, Toshio Nishioka, Hisami Takeda, Kiyoshi Kasamatsu
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Patent number: 4299969Abstract: Lower alkyl .beta.-(S-benzylmercapto)-.beta.,.beta.-pentamethylenepropionates are prepared in improved yields by reacting lower alkyl cyclohexylideneacetates with benzylmercaptan in the presence of an alkali metal mercaptide.Type: GrantFiled: August 8, 1980Date of Patent: November 10, 1981Assignee: SmithKline CorporationInventors: William F. Huffman, Nelson C. Yim
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Patent number: 4297367Abstract: The invention relates to new 2-phenyl-4-pyrone derivatives which can be used in agriculture. They correspond to the general formula: ##STR1## in which X.sub.1 and X.sub.2, which are identical or different, each represent a hydrogen or halogen atom, with the proviso that at least one of these substituents represents a halogen atom, R.sub.1 represents an alkoxy radical (C.sub.1 -C.sub.4), an alkenyloxy radical containing from 2 to 4 carbon atoms, a propargyloxy radical, a halogenoalkoxy radical (C.sub.1 -C.sub.4), an amino radical, an alkylamino radical (C.sub.1 -C.sub.4) or a dialkylamino radical in which each of the alkyl parts, which are identical or different, contains from 1 to 4 carbon atoms, R.sub.2 represents a halogen atom, an alkyl radical containing from 1 to 5 carbon atoms, an alkoxy radical (C.sub.1 -C.sub.4), an alkenyloxy radical (C.sub.3 -C.sub.4), an alkynyloxy radical (C.sub.3 -C.sub.4), an alkylthio radical (C.sub.1 -C.sub.4), a halogenoalkyl radical (C.sub.1 -C.sub.Type: GrantFiled: March 24, 1980Date of Patent: October 27, 1981Assignee: Rhone Poulenc AgrochemieInventors: Francois Guigues, Stephane Trinh
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Patent number: 4293569Abstract: Phenylguanidine derivatives are provided having the structure ##STR1## wherein R is hydrogen, lower alkyl, cycloalkyl, lower alkoxy, phenyl, phenylalkyl, phenoxy, phenylalkoxy, lower alkoxyalkyl, phenoxyalkyl, alkylamino, dialkylaminoalkyl, alkylthio, phenylthio, phenylthioalkyl, and alkylthioalkyl; R.sup.1 is lower alkyl or benzyl; R.sup.2 is hydrogen, lower alkoxy carbonyl, and lower alkanoyl; R.sup.3 is lower alkyl, cycloalkylalkyl, lower alkenyl, lower alkynyl or benzyl; and n is 0 or 1. These compounds are useful as anthelmintic agents.Type: GrantFiled: May 12, 1978Date of Patent: October 6, 1981Assignee: E. R. Squibb & Sons, Inc.Inventors: Rudiger D. Haugwitz, Peter C. Wade, Barbara V. Maurer
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Patent number: 4293555Abstract: Disclosed are 6- and 6,6-disubstituted-2-substituted-oxapen-2-em-3-carboxylic acids of the following structure: ##STR1## wherein: R.sup.1 and R.sup.2 are independently selected from hydrogen, alkyl, alkoxyl, aralkyl, aryl, heterocyclyl and heterocyclylalkyl; R is selected from hydrogen, --OR, --SR, --NR.sub.2, alkyl, aryl, aralkyl, heterocyclyl, or heterocyclylalkyl. Such compounds and their pharmaceutically acceptable salt, and ester derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.Type: GrantFiled: October 10, 1979Date of Patent: October 6, 1981Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Frank P. DiNinno
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Patent number: 4291176Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: August 24, 1977Date of Patent: September 22, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
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Patent number: 4287210Abstract: There are described acylaniline derivatives which in the phenyl ring are substituted in the meta-position with respect to the amino group by an aliphatic oxymethyl group or aryloxymethyl group, or by an aliphatic thiomethyl group or arylthiomethyl group. Compounds of this type have a very favorable microbicidal spectrum. They are used principally for combating phytopathogenic fungi and bacteria.Type: GrantFiled: November 21, 1979Date of Patent: September 1, 1981Assignee: Ciba-Geigy CorporationInventors: Wolfgang Eckhardt, Walter Kunz, Adolf Hubele
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Patent number: 4284643Abstract: Fluorine-containing phenylacetic acid esters of the formula ##STR1## in which R represents the radical of an alcohol customary in the case of pyrethroids,R.sup.1 represents C.sub.2-4 -alkyl, C.sub.2-4 -alkenyl or cyclopropyl,X represents H, halogen, alkyl, alkoxy, OCHF.sub.2, SCHF.sub.2, SCClF.sub.2 or SCF.sub.3 andX.sup.1 can vary widely or form a fused ring with X,the overall compound necessarily containing a fluorine atom, which compounds possess arthropodicidal properties. Intermediates therefor and an overall synthesis from an alcohol of the formula ROH and a toluene of the formula ##STR2## are also shown.Type: GrantFiled: August 6, 1979Date of Patent: August 18, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Erich Klauke, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel, Reinhard Lantzsch, Albrecht Marhold
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Patent number: 4279637Abstract: This invention discloses chemical compounds of the formula ##STR1## wherein X and Z are each independently selected from the group consisting of halogen, haloalkyl, nitro, cyano, alkyl, alkoxy and alkylthio; m and n are each independently integers of from 0 to 4; Y is selected from the group consisting of oxygen, sulfur, methylene, sulfonyl and sulfinyl; and R is selected from the group consisting of hydrogen, alkyl and alkoxy. The compounds of the above description are useful as herbicides.Type: GrantFiled: May 29, 1980Date of Patent: July 21, 1981Assignee: Velsicol Chemical CorporationInventor: Frank Wu
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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: 4270948Abstract: .alpha.-[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.Type: GrantFiled: October 17, 1979Date of Patent: June 2, 1981Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
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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
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Patent number: 4266074Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: July 16, 1975Date of Patent: May 5, 1981Assignee: Sumitomo Chemical Company LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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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: 4266082Abstract: A process for the preparation of 4-fluoro-3-phenoxy-toluene of the formula ##STR1## comprising reacting 3-bromo-4-fluoro-toluene, of the formula ##STR2## with potassium phenolate, or with sodium phenolate in the presence of a potassium salt, in a diluent in the presence of copper as catalyst at a temperature between about 120.degree. and 180.degree. C.Type: GrantFiled: August 17, 1979Date of Patent: May 5, 1981Assignee: Bayer AktiengesellschaftInventors: Reimer Collin, Hans-Joachim Diehr, Uwe Friesnitz
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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