Halogen In Acid Moiety Patents (Class 560/30)
  • Patent number: 4824670
    Abstract: The present invention relates to new carbazates of the general formula (I), ##STR1## wherein A is C.sub.3-10 alkyl, C.sub.3-10 alkenyl, C.sub.2-10 haloalkyl, trifluoromethyl, phenyl-C.sub.1-3 alkyl, phenyl-C.sub.2-3 -alkenyl, naphthyl-C.sub.1-3 alkyl; phenyl optionally substituted by one or more identical or different substituent(s) selected from C.sub.1-4 alkyl, halogen, C.sub.1-4 alkoxy and hydroxy; C.sub.3-7 cycloalkyl-C.sub.1-3 alkyl; optionally nitro-substituted furyl; diphenyl-hydroxy-methyl or indazolyl optionally substituted by one or more C.sub.1-4 alkoxy group(s) andR represents C.sub.1-4 alkyl,with the proviso that if R stands for ethyl, A is other than tertiary butyl, and acid addition salts thereof, a process for the preparation thereof and feed-additives comprising the same.The compounds of the general formula (I) may be used in animal husbandry due to their weight-gain increasing and fodder utilization improving effect.
    Type: Grant
    Filed: December 11, 1985
    Date of Patent: April 25, 1989
    Assignee: Egis Gyogyszergyar
    Inventors: Ildiko Ratz nee Simonek, Pal Benko, Edit Bernenyi nee Poldermann, Karoly Magyar
  • Patent number: 4786745
    Abstract: Novel 2,2-dihalovinyl haloformates are described of general formula: ##STR1## in which: X is a chlorine or bromine atom;X.sub.1 and X.sub.2 are the same or different and are chlorine or bromine.The compounds are prepared by reaction of a 1,2,2,2-tetrahaloethyl haloformate of formula: ##STR2## in which: X.sub.1, X.sub.2 and X are as described hereinabove;X.sub.3 is chlorine or bromine and is always bromine when X.sub.1 and/or X.sub.2 is bromine andX.sub.4 is chlorine or bromine, with a metal such as zinc or magnesium in a solvent.The novel compounds are very useful for the preparation of 2,2-dihalovinyl carbonates and carbamates which may be used as insecticides or as comonomers.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: November 22, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Mark P. Bowman, Roy A. Olofson, Thierry Malfroot, Jean-Pierre Senet
  • Patent number: 4772695
    Abstract: A process for the preparation of vinyl carbamates of formula I ##STR1## is described which comprises heating an .alpha.-halogeno-carbamate of formula II ##STR2## in which X is a halogen atom at a temperature between 70.degree. and 250.degree. C. for a period of time between several minutes up to several hours. R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different. The process is applicable to a great variety of products in which R.sub.1, R.sub.2, R.sub.3, and R.sub.4 have different meanings. The process permits to prepare in a simple and economical fashion, vinyl carbamates, which have industrial value and novel vinyl carbamates.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: September 20, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Roy A. Olofson, Gary P. Wooden, Jonathan T. Martz
  • Patent number: 4767447
    Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy or difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are C.sub.2 -C.sub.5 alkylene;R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.
    Type: Grant
    Filed: September 12, 1986
    Date of Patent: August 30, 1988
    Assignee: Stauffer Chemical Company
    Inventors: David L. Lee, William J. Michaely
  • Patent number: 4760057
    Abstract: This invention relates to novel (acyloxyalkoxy)carbonyl derivatives as bioreversible prodrug moieties for primary and secondary amine functions in drugs having a primary or secondary amine function thereon. Hydrolytic enzymes are used to trigger the regeneration of the parent amine drug of the carbamate prodrug moiety. The case also contains pharmaceutical composition, method of treatment and process claims.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: July 26, 1988
    Assignee: Merck & Co., Inc.
    Inventor: Jose Alexander
  • Patent number: 4752615
    Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, particularly their strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.
    Type: Grant
    Filed: November 13, 1986
    Date of Patent: June 21, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
  • Patent number: 4751240
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R.sup.1 is hydrogen, or alkyl, alkenyl, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 --or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --(PO)R.sup.2 13 , --S--, --SO--or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: June 14, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
  • Patent number: 4724256
    Abstract: This invention relates to urethane linked hydroxy aromatic isocyanates and to a process for producing such urethane linked hydroxy aromatic isocyanates. The compositions are formed by reacting one equivalent aromatic diisocyanate with one equivalent of an alkylene polyol under conditions such that only one of the isocyanate groups react with the hydroxyl group of the polyol. Conditions are controlled such that the urethane linked hydroxy aromatic isocyanates are formed. The resulting product is suited for producing a variety of elastomers including a one component polyurethane elastomer.
    Type: Grant
    Filed: January 13, 1987
    Date of Patent: February 9, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: William E. Starner, Barton Milligan, Roland E. Grandin
  • Patent number: 4723029
    Abstract: This invention relates to organic acid-substituted guanidine compounds. Also disclosed are methods for preparing the compounds, compositions containing them, and methods for their use as anthelmintics.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: February 2, 1988
    Assignee: Schering Corporation
    Inventors: Dhiru B. Vashi, Jeffrey N. Clark, Neil A. Lindo
  • Patent number: 4694097
    Abstract: Carbamate esters are produced by reacting at ambient or elevated temperature an amine with carbon monoxide and an alcohol in the presence of a protonic acid, a dehydrating agent, for example a molecular sieve, and a catalyst comprising (a) at least one metal selected from the group palladium, rhodium, ruthenium, iridium and cobalt, and (b) at least one of the metals copper, molybdenum and iron, the components (a) and (b) being in the form of elemental metals or compounds thereof. The presence of the dehydrating agent reduces the formation of by-product carbon dioxide.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: September 15, 1987
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, David J. H. Smith
  • Patent number: 4687872
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: August 18, 1987
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm
  • Patent number: 4681973
    Abstract: Acylated amino acids having the general formula ##STR1## are prepared by reacting a compound of formula II ##STR2## with a compound of formula IIIROCOClwherein R, R.sub.1, R.sub.2 and R.sub.3 are as defined herein.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: July 21, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventor: Martin L. Kantor
  • Patent number: 4678856
    Abstract: The present invention relates to a method of manufacturing aromatic urethane, an aromatic mononitro-compound, an aromatic primary amine, and carbon monoxide being reacted using a catalyst containing a platinum group metal-containing compound as a major constituent to prepare N,N'-di-substituted urea. The resultant N,N'-di-substituted urea is reacted with a hydroxyl group-containing organic compound to prepare an aromatic primary amine and aromatic urethane, and the aromatic primary amine is separated to obtain aromatic urethane.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: July 7, 1987
    Assignee: Nippon Kokan Kabushiki Kaisha
    Inventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Itaru Sakai, Osamu Tajima
  • Patent number: 4668703
    Abstract: This invention is for .gamma.-allenyl-.gamma.-aminobutyric acid derivatives which are .gamma.-aminobutyric acid transaminase inhibitors.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: May 26, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Alexander Krantz, Arlindo L. Castelhano, Diana H. Pliura
  • Patent number: 4665193
    Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## intervene in the conversion of angiotensinogen to angiotensin II by inhibiting renin and thus are useful as anti-hypertensive agents.
    Type: Grant
    Filed: June 27, 1986
    Date of Patent: May 12, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Denis E. Ryono, Edward W. Petrillo, Jr.
  • Patent number: 4661515
    Abstract: Novel compounds possessing both angiotensin enzyme inhibitory activity and diuretic activity are disclosed. The compounds are represented by the general formula ##STR1## in which X is ##STR2## in which 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, and cycloalkyl, and may be the same or different; n is an integer from 0 to 4 inclusive; M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cyloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl, or M and R.sub.6 taken together with the nitrogen to which M is bonded and the carbon to which R.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: April 28, 1987
    Assignee: USV Pharmaceutical Corporation
    Inventors: Edward S. Neiss, John T. Suh, John J. Piwinski
  • Patent number: 4639468
    Abstract: A glycinamide derivative of the general formula I: ##STR1## wherein: R is a linear or ramified alkyl group C.sub.5 -C.sub.18, a linear or ramified alkenyl group C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9, C.sub.10, C.sub.11, C.sub.12, C.sub.13, C.sub.14, C.sub.15, C.sub.16, C.sub.17 or C.sub.18, a linear or ramified alkynyl group C.sub.4 -C.sub.10, a linear or ramified acyl group C.sub.4 -C.sub.18, a linear or ramified alkyl group C.sub.1 -C.sub.10, substituted by a phenoxy group, by a hydroxy radical, by an acetoxy radical, by a carboxy radical, by a linear or ramified alkoxycarbonyl group C.sub.1 -C.sub.4, by a carbonyl radical, by a carboxaldehyde group, by an acetal or cetal group, by one or more phenyl groups, by one or more phenyl groups substituted by a halogen atom such as fluorine, chlorine or bromine,R.sub.1 represents hydrogen, a linear or ramified alkyl group C.sub.1, C.sub.2, C.sub.3, C.sub.4, C.sub.5, C.sub.6, C.sub.7, C.sub.8, C.sub.9 or C.sub.10, a linear or ramified acyl group C.sub.1 -C.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: January 27, 1987
    Assignee: Continental Pharma Inc.
    Inventors: Romeo Roncucci, Claude L. Gillet, Alexis H. Cordi, Mark A. Martens, Joseph L. Roba, Paul J. Niebes, Georges E. Lambelin, William R. Van Dorsser
  • Patent number: 4629804
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: December 16, 1986
    Assignee: Catalytica Associates
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4618357
    Abstract: The growth of turf grass can be retarded by applying to said turf grass an effective growth retarding amount of a compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, or haloalkyl; R.sub.4 is hydrogen; C.sub.1-4 alkyl, alkenyl, alkoxy, haloalkyl; C.sub.1-2 alkylamino, C.sub.1-2 alkylthio, C.sub.2-4 cycloalkyl, C.sub.2-6 alkoxyalkyl, C.sub.2-6 alkylthiomethyl, amino, phenoxy, phenamino, or furan; and R.sub.5 is hydrogen or C.sub.1-4 alkyl.
    Type: Grant
    Filed: February 13, 1985
    Date of Patent: October 21, 1986
    Assignee: Monsanto Company
    Inventors: Gerhard H. Alt, John P. Chupp, Lane A. Clizbe
  • Patent number: 4610985
    Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
  • Patent number: 4603216
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst comprising a bis phosphine ligand.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 29, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4600793
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a halide-free ruthenium catalyst is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a primary amine in the reaction solution.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 15, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine
  • Patent number: 4594441
    Abstract: A process for the preparation of urethanes. Urethanes having the general formula R.sub.1 (NHCOOR.sub.2).sub.n are reacted with an alcohol at a temperature of 120.degree. to 400.degree. C. in amounts such that, for every mol of the urethane, at least one mol of the alcohol is present. R.sub.1 is a radical obtained by removing the isocyanate groups from an n-functional organic isocyanate, which isocyanate has a boiling point greater than 100.degree. C. at atmospheric pressure. R.sub.2 is a radical obtained by removing the hydroxyl group from a monohydric alcohol which has a boiling point greater than 140.degree. C. at atmospheric pressure.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: June 10, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Klaus Konig, Rudolf Fauss, Peter Heitkamper
  • Patent number: 4593116
    Abstract: Urethanes are made by reacting an organic nitro compound with an organic compound containing at least one hydroxyl group in the presence of carbon monoxide, hydrogen and a catalyst system. The carbon monoxide and hydrogen are used in quantities such that the molar ratio of CO to H.sub.2 is from 0.3:1 to 3:1. The catalyst system is made up of at least one noble metal or compound of a noble metal from Group VIIIB of the Periodic System of Elements, at least one organic nitrogen base and a co-catalyst combination of iron or copper oxidic or hydroxidic compound and a chloride compound. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: June 13, 1984
    Date of Patent: June 3, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
  • Patent number: 4582923
    Abstract: Urethanes are made by reacting a primary amine with carbon monoxide and a compound containing at least one hydroxyl group in the presence of an oxidizing agent and a catalyst system. The catalyst system is made up of (i) a noble metal and/or a noble metal compound of a metal of the Eighth Secondary Group of the Periodic System of Elements and (ii) an oxidizing quinoid and/or a compound capable of being converted to an oxidizing quinoid compound under the reaction conditions. The catalyst system may optionally include (iii) metal compounds of elements of the Third to Fifth Main Groups and/or First to Eighth Secondary Groups of the Periodic System of Elements and/or (iv) a tertiary amine. This reaction is generally carried out at a temperature of from 100.degree. to 300.degree. C. and at a pressure of from 5 to 500 bars. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: May 17, 1985
    Date of Patent: April 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Robert Becker, Johann Grolig, Helmut Waldmann
  • Patent number: 4570012
    Abstract: Production of tertiary aralkyl urethanes, such as tetramethyl xylylene diurethanes, by addition of corresponding diols and carbamic acid esters at moderate temperatures and in the presence of acid catalyst.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: February 11, 1986
    Assignee: American Cyanamid Co.
    Inventors: Balwant Singh, Peter S. Forgione, Laurence W. Chang
  • Patent number: 4568763
    Abstract: N-acyl-acyloxy aromatic amines, e.g. 4-acetoxyacetanilide (AAA), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with hydroxylamine or a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement and accompanying acylation by contacting the ketoxime with a carboxylic acid anhydride and a Beckmann rearrangement catalyst to form the N-acyl-acyloxy aromatic amine.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: February 4, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4568761
    Abstract: A new and improved process for preparing tertiary aralkyl carbamates is disclosed. The process comprises reacting a mixture of a lower alkyl carbamate with a tertiary aralkyl halide at a temperature of about 50.degree. C. to about 100.degree. C. until formation of the tertiary aralkyl carbamate is substantially complete. In a preferred process, an alkenyl aromatic compound which is the olefin precursor of the aralkyl halide employed, is added to the reaction mixture to improve the yield of tertiary aralkyl carbamate products. The tertiary aralkyl carbamates prepared by the process of this invention are useful intermediates which may be thermally cracked in the presence of base catalysts to form tertiary aralkyl isoayanates.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: February 4, 1986
    Assignee: American Cyanamid Company
    Inventor: William A. Henderson, Jr.
  • Patent number: 4560795
    Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Y is F.sub.2 CH--, F.sub.3 C--, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR2## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and 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; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: February 6, 1984
    Date of Patent: December 24, 1985
    Assignee: Merrell Dow France et Cie.
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4557871
    Abstract: Novel styrene derivatives of the general formula ##STR1## wherein X is hydrogen or halogen, X.sup.1 is halogen, R is hydrogen or methyl, Y is hydroxymethyl, carboxyl, --COOR.sup.1 or --COR.sup.2 wherein R.sup.1 is prenyl, geranyl, farnesyl, cyclohexyl, phthalidyl, straight or branched chain alkyl having 1 to 6 carbon atoms, or said alkyl substituted with hydroxy, methoxy, pyridyl or alkanoyloxy having 2 to 16 carbon atoms, and R.sup.2 is amino, hydroxyamino mono-(or di-)alkylamino in which the alkyl moiety contains 1 or 2 carbon atoms, ethoxycarbonylmethylamino, carboxymethylamino, thiazolylamino, cyclohexylamino, pyridylamino, morpholino, N-methylpiperazino, phenylamino, phenylamino substituted with one or two of halogen, hydroxy, methyl, methoxy, trifluoromethyl or carboxyl at the phenyl ring, and the pharmaceutically acceptable salts thereof when Y is carboxyl are disclosed. These compounds exhibit high and long-lasting anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: May 14, 1984
    Date of Patent: December 10, 1985
    Assignee: Taisho Pharmaceutical Co., Ltd.
    Inventors: Katsuo Hatayama, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Tomomi Ota, Kazuto Sekiuchi, Kaoru Sota
  • Patent number: 4547524
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as herein defined useful as insecticides, is described.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: October 15, 1985
    Assignee: Hokko Chemical Industry Co., Ltd.
    Inventors: Kimiyoshi Kaneko, Hiromichi Ishikawa, Satoru Moriyama, Tsugio Uchiyama
  • Patent number: 4533745
    Abstract: Amino ketone enantiomers and their direct preparation are disclosed. The ketone may be reduced to yield carbinol enantiomer which has pharmaceutical activity.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: August 6, 1985
    Assignee: Merck & Co., inc.
    Inventor: David E. McClure
  • Patent number: 4519834
    Abstract: The ethynyl-phenylureas of the formula I ##STR1## wherein X is hydrogen, halogen, lower alkyl, lower alkoxy, haloalkyl or nitro, Y is oxygen or sulfur, R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, phenyl or benzyl, R.sub.2 is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl or benzyl, R.sub.1 and R.sub.2 together with the nitrogen atom to which they are bound are also a pyrrolidine, piperidine, morpholino or piperazine ring, R.sub.3 is hydrogen or lower alkyl, and R.sub.4 is hydrogen, alkyl, phenyl, pyridyl, alkenyl, cycloalkyl or cycloalkenyl, are novel substances. They are characterized by strong herbicidal activity.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: May 28, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Henry Szczepanski
  • Patent number: 4505859
    Abstract: 2-Haloethylamides are prepared by reaction of 2-oxazolidinone or C.sub.1-6 alkyl or phenyl derivatives thereof with an acid halide.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: March 19, 1985
    Assignee: The Dow Chemical Company
    Inventor: Graham S. Poindexter
  • Patent number: 4501756
    Abstract: Use of a compound of the formula: ##STR1## wherein X and Y are, same or different, each a lower alkyl group, a lower alkoxy group or a halogen atom and R is a methyl group or an ethyl group as a fungicidal agent against plantpathogenic fungi, particularly their drug-resistant strains.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: February 26, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiro Kato, Junya Takahashi, Katsuzo Kamoshita
  • Patent number: 4498922
    Abstract: Substituted N-aminomethylhaloacetanilides of the formula ##STR1## where R.sup.1 and R.sup.2 are each C.sub.1 -C.sub.2 -alkyl, R.sup.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sup.4 is cyano or --CO--NH.sub.2, R.sup.5 is C.sub.1 -C.sub.6 -alkyl and X is halogen, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: July 23, 1982
    Date of Patent: February 12, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Eicken, Wolfgang Rohr, Bruno Wuerzer
  • Patent number: 4490551
    Abstract: A process for producing urethanes by reacting aromatic amino compounds with aliphatic, cycloaliphatic or araliphatic alcohols and carbon monoxide under conditions of elevated temperature and pressure characterized in that the reaction takes place in the presence of(a) selenium, selenium compounds, sulfur and/or sulfur compounds,(b) aromatic nitro compounds,(c) tertiary organic amines and/or alkali metal salts of weak acids,(d) oxidizing agents of a specified group and, optionally(e) ammonia and/or aliphatic, araliphatic, cycloaliphatic or heterocyclic amines containing at least one hydrogen atom bound to an amine nitrogen.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: December 25, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Armin Zenner
  • Patent number: 4487952
    Abstract: Process for the preparation of esters of carbamic acids by carbonylation of aromatic nitrocompounds, with carbon monoxide, in the presence of alcohols and of catalyst consisting of metallic selenides.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: December 11, 1984
    Assignee: Anic S.p.A.
    Inventor: Villiam Giroldini
  • Patent number: 4474807
    Abstract: This invention is directed to novel antimicrobial agents. More particularly, this invention is directed to 2-(3-iodo-2-propynyloxy)-ethyl carbamates of the formula ##STR1## wherein R is hydrogen, linear or branched alkyl of from 1 to 12 carbon atoms, cycloalkyl of from 4 to 8 carbon atoms, aryl, substituted aryl, aralkyl, or arylsulfonyl;R.sup.1 and R.sup.2, which may be the same or different, each are hydrogen, linear or branched alkyl or alkenyl of from 1 to 6 carbon atoms, or cycloalkyl of from 5 to 7 carbon atoms, or R.sup.1 and R.sup.2, taken together, represent --(CH.sub.2).sub.m --, in which m is an integer of from 4 to 6; andR.sup.3, R.sup.4, R.sup.5, and R.sup.6, which may be the same or different, each represent hydrogen, alkyl of from 1 to 4 carbon atoms, or aryl, or CCl.sub.3, or R.sup.3 and R.sup.5 or R.sup.4 and R.sup.6, taken together, represent --(CH.sub.2).sub.n --, in which n is an integer of from 3 to 5,as well as a process for their preparation and their use as antimicrobial agents.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 2, 1984
    Assignees: Henkel Kommandigesellschaft auf Aktien, Montedison S.p.A.
    Inventors: Werner Gerhardt, Rudolf Lehmann
  • Patent number: 4469882
    Abstract: A process for producing aromatic carbamates in high yield is described, which comprises reacting aromatic nitro compounds, organic compounds containing a hydroxy group, and carbon monoxide in the presence of a catalyst comprising: (1) a platinum group metal or its compound, (2) metallic vanadium or its compound, (3) metallic iron or its compound, (4) a halogen atom, and (5) a tertiary amine, wherein the amount of each component used and the composition are adjusted within specific ranges.
    Type: Grant
    Filed: June 23, 1982
    Date of Patent: September 4, 1984
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Tsutomu Takeuchi, Mineo Nishi, Toshio Irie, Hirotaka Ryuto
  • Patent number: 4467101
    Abstract: Acylamido-3-cephem-4-carboxylic acid compounds of the formula ##STR1## in which the index n represents an integer of from 1 to 4,the index m represents 0 or 1,X represents oxygen, sulphur or an --NH-- group,W represents a --CO--, --CO--NHSO.sub.2 -- or --SO.sub.2 NH--CO-- group, orX-W together represent a --CO-- or --CO--NHSO.sub.2 -- group,A represents optionally substituted phenylene, thienylene or furylene,Y represents hydrogen, hydroxyl, formyloxy, amino or sulpho optionally present in salt form, andZ represents hydrogen, orY and Z together represent an oxo group or an .dbd.N--O--R.degree. group in which R.degree. represents hydrogen or optionally substituted lower alkyl,R.sub.1 represents hydrogen, lower alkyl, lower alkoxy, halogen or a group of the formula --CH.sub.2 --R.sub.2 in which R.sub.2 is a free, esterified or etherified hydroxy or mercapto group or a quaternary ammonium group, andR.sub.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: August 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Karoly Kocsis, Peter Schneider, Bruno Fechtig, Riccardo Scartazzini
  • Patent number: 4448773
    Abstract: Compounds of the formula ##STR1## in which Ar is 2-alkyl-, -alkoxy- or -halo-methyl-phenyl or .alpha.-naphthyl, each of which is further substituted,R.sub.1 is 2-furyl, 2-tetrahydrofuryl, alkenyl, cyclopropyl, .beta.-alkoxyethyl, hydroxymethyl, triazolylmethyl, imidazolylmethyl, pyrazolylmethyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyloxy, dialkylaminosulfinyloxy, phosphoric or thiophosphoric esters or amides, or alkylcarbonyloxy,R.sub.7 is hydrogen or optionally-substituted methyl or ethyl, andR.sub.8 is alkyl optionally substituted by alkoxy,are microbicidally, in particular fungicidally, active. Preferred compounds are those in which Ar is 2-methylphenyl, 2-methoxyphenyl, 2-chlorophenyl or .alpha.-naphthyl, each of which is further substituted by azido, and each of R.sub.7 and R.sub.8 is methyl.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: May 15, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Riebli, Hanspeter Fischer, Rudolph C. Thummel, Adolf Hubele
  • Patent number: 4439616
    Abstract: Production of tertiary aralkyl isocyanates, such as tetramethyl xylylene diisocyanates, by thermal cracking of corresponding urethanes formed by addition of corresponding olefins and carbamic acid esters at moderate temperatures and in the presence of acid catalyst.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: March 27, 1984
    Assignee: American Cyanamid Company
    Inventors: Balwant Singh, Laurence W. Chang, Peter S. Forgione
  • Patent number: 4438270
    Abstract: Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: wherein Y is ClCH.sub.2, F.sub.2 CH--, F.sub.3 C--, ClCH.sub.2 --, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR1## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and 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 ##STR2## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or .rho.-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: March 20, 1984
    Assignee: Merrell Toraude et Compagnie
    Inventors: Philippe Bey, Michel Jung
  • Patent number: 4430505
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: February 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann
  • Patent number: 4430262
    Abstract: Isocyanates and derivatives thereof are prepared by oxidative conversion of compounds having at least one group ##STR1## wherein X represents OY or ##STR2## wherein Y is H, a metal ion or group NR.sup.3 R.sup.4 R.sup.5 R.sup.6 wherein each of R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is H, alkyl or (substituted) (alk)aryl and Z is a (substituted) alkyl or aryl group. Phenyl isocyanate and derivatives thereof are preferably prepared electrochemically from the corresponding oxamides and oxanilides.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: February 7, 1984
    Assignee: Shell Oil Company
    Inventors: Rainer Engels, Jan H. H. Meurs
  • Patent number: 4426222
    Abstract: Novel carbaminic acid phenyl esters of the general formula ##STR1## are described, in which R.sub.1 is C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.2 -alkyl, di-C.sub.1 -C.sub.2 -alkoxy-C.sub.1 -C.sub.2 -alkyl, cyano-C.sub.1 -C.sub.2 -alkyl, halogen-C.sub.1 -C.sub.2 -alkyl, phenyl-C.sub.1 -C.sub.2 -alkyl, 1,3-dioxolan-2-yl-methyl, 2-methyl-1,3-dioxolan-4-yl-methyl, 2,2-dimethyl-1,3-dioxolan-4-yl-methyl or aminocarbonylmethyl;R.sub.2 is phenyl optionally mono- or disubstituted by one or more substituents selected from the group consisting of halogen, methyl and methoxy; andR.sub.3 is C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, cyclopropyl or trichloromethyl, or R.sub.1 is methyl or ethyl, R.sub.2 is .alpha.-cyanobenzyl or 1-cyano-2-phenylethyl and R.sub.3 is ethyl.
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: January 17, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Gerhard Boroschewski, Ludwig Nusslein, Friedrich Arndt
  • Patent number: 4425361
    Abstract: Formamido-carbamates of the formula ##STR1## wherein R.sub.1 is ##STR2## R.sub.2 is ##STR3## or R.sub.4 --CH.sub.2 --CH.sub.2 --, R.sub.3 is hydrogen, ##STR4## R.sub.4 is ##STR5## R.sub.5, R.sub.6 and R.sub.7 independently of one another are each hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl,processes for producing them and their use for combating pests are described.
    Type: Grant
    Filed: November 18, 1981
    Date of Patent: January 10, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Lohmann, Christian d'Hondt, Guenter Rist
  • Patent number: 4404019
    Abstract: A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 cycloalkyl group, X is a chlorine atom or a bromine atom and Y is a hydrogen atom or a C.sub.1 -C.sub.4 alkoxy group, which is useful as a herbicide.
    Type: Grant
    Filed: December 8, 1981
    Date of Patent: September 13, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamon Uematsu, Shunichi Hashimoto, Hiroshi Matsumoto
  • Patent number: H78
    Abstract: Energetic diols of the formula ##STR1## wherein R is --H, --NO, --NO.sub.2, --CN, or --CH.sub.2 COOH, and diesters of the formula ##STR2## wherein R is --H, --NO, --NO.sub.2, --CN, --CH.sub.2 COOCH.sub.3, --CH.sub.2 COOCH.sub.2 C(NO.sub.2).sub.2 CH.sub.3, or --CH.sub.2 COOCH.sub.2 C(NO.sub.2).sub.3 and R' is an alkyl, fluoroalkyl, chloroalkyl, aryl, fluoroaryl, chloroalkyl, aralkyl, fluoroaralkyl, chloroaralkyl, or alkene group.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: July 1, 1986
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Horst G. Adolph, Michael E. Sitzmann