Halogen Bonded Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/295)
  • Patent number: 5008276
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 4985449
    Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultanously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N-- or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.
    Type: Grant
    Filed: June 13, 1989
    Date of Patent: January 15, 1991
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4983211
    Abstract: The present disclosure is directed to substituted cyclohexanedione compounds, the preparation of said compounds, compositions containing said compounds and the use of said compositions in the selective pre- and postemergent kill and control of grassy weeds in the presence of various crop plants.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: January 8, 1991
    Assignee: DowElanco
    Inventors: Lowell D. Markley, Christopher T. Hamilton, Beth A. Swisher, Jacob Secor
  • Patent number: 4973697
    Abstract: A 2-halopyridine-6-sulfonic acid and its salt represented by the formula: ##STR1## wherein X is a halogen atom, and M is a hydrogen atom or a metal atom. The compounds are useful as intermediates for producing fluorinating agents (reagents for introducing fluorine atoms).
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: November 27, 1990
    Assignees: Onoda Cement Co., Ltd., Sagami Chemical Research Center
    Inventors: Teruo Umemoto, Kikuko Harasawa
  • Patent number: 4966974
    Abstract: The invention relates to 2-phenylsulphinyl-nitro-pyridines of the formula ##STR1## in which R.sub.1 denotes hydrogen, alkyl or halogen andR.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 independently of one another represent hydrogen, halogen, alkyl, haloalkyl, alkyoxy, haloalkoxy, cyano, nitro, carboxyl, alkoxycarbonyl, carboxamido, N-alkyl- or N,N-dialkylcarboxamido, acyl or primary, secondary or tertiary amino.processes for their preparation, and their use as microbicides for the protection of materials and fungicides in plant protection.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: October 30, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexander Klausener, Wilfried Paulus, Hans-Georg Schmitt, Wilhelm Brandes
  • Patent number: 4963682
    Abstract: A dihydropyridine.rarw..fwdarw. pyridinium salt type of redox, or chemical, delivery system for the site-specific and/or site-enhanced delivery of a radionuclide to the brain is provided. A chelating agent capable of chelating with a radionuclide and having a primary, secondary or tertiary amino function can be converted to the corresponding analogue in which said function is replaced with a dihydropyridine.rarw. .fwdarw. pyridinium salt redox system and then complexed with a radionuclide to provide a new radiopharmaceutical that, in its lipoidal dihydropyridine form, penetrates the blood-brain barrier ("BBB") and allows increased levels of radionuclide concentration in the brain, particularly since oxidation of the dihydropyridine moiety in vivo to the ionic pyridinium salt retards elimination from the brain while elimination from the general circulation is accelerated.This radionuclide delivery system is well suited for use in scintigraphy and similar radiographic techniques.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: October 16, 1990
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4960897
    Abstract: Disclosed herein is an N-[2-(pyridyl)propyl]-N-substituted sulfonamide represented by the following general formula (I): ##STR1## wherein J represents a phenyl group which may be substituted or benzo-condensed, A represents --CH.sub.2 --, --CH.dbd.CH--, --O-- or --N(r)-- (wherein r represents an alkyl group having 1 to 4 carbon atoms), b represents 0 or 1, R represents an alkyl group, alkenyl group, alkynyl group, alkoxy group, fluoroalkyl group or formyl group, D represents a hydroxyl group, E represents a halogen atom, an alkylsulfonyloxy group or a benzenesulfonyloxy group which may be substituted, or D and E represent --O-- in combination, and V represents a pyridyl group which may be substituted, a herbicide containing said N-[2-(pyridyl)propyl]-N-substituted sulfonamide as an active ingredient and a 1-(halogenomethyl)vinylpyridine as an intermediate thereof.
    Type: Grant
    Filed: March 2, 1988
    Date of Patent: October 2, 1990
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Manabu Katsurada, Toyohiko Shike, Emiko Mikami, Osamu Ikeda
  • Patent number: 4952235
    Abstract: (Hetero) aryloxynaphthalenes having substituents bonded via sulphur having herbicidal activity and of the formula ##STR1## in which m represents the number 0, 1 or 2,n represents the numbers 0 or 1,R.sup.1 represents hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 represents hydrogen or halogen,R.sup.3 represents halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,R.sup.4 represents hydrogen or halogen,X represents nitrogen or the group C--R.sup.5, whereinR.sup.5 represents hydrogen or halogen,Y represents oxygen or one of the groupings ##STR2## wherein R.sup.6 represents hydrogen, alkyl, --CO--Z or --SO.sub.2 --Z andZ represents hydrogen, halogen or an optionally substituted alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkinyl, aryl or heteroaryl radical.
    Type: Grant
    Filed: June 22, 1989
    Date of Patent: August 28, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 4950679
    Abstract: Disclosed herein is a compound of the formula: ##STR1## wherein Ar is pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, isoquinoline ring or thiazole ring, and those rings may be substituted by 1.about.3 of substituents selected from the group consisting of halogen, C.sub. 1 .about.C.sub.4 -alkyl, C.sub.1 .about.C.sub.4 -alkoxy, CF.sub.3 and nitro,R.sup.1 is C.sub.1 .about.C.sub.8 -alkyl; C.sub.1 .about.C.sub.7 -alkyl which is substituted by 1.about.3 of F, Cl or Br, C.sub.1 .about.C.sub.4 -alkoxy or C.sub.1 .about.C.sub.4 -alkylthio; C.sub.3 .about.C.sub.7 -cycloalkyl which may be substituted by 1.about.4 of F, Cl or methyl; C.sub.3 .about.C.sub.6 -cycloalkylmethyl which may be substituted by 1.about.4 of F, Cl, Br or methyl; allyl, propargyl, phenyl or benzyl; R.sup.2 is C.sub.1 .about.C.sub.4 -alkyl which may be substituted by 1.about.3 of F or Cl,x is integer of 0, 1 or 2, excepting wherein Ar is pyridine ring which is substituted by R.sup.1 --S(O)x and --O--SO.sub.2 R.sup.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: August 21, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shoichi Kato, Tatsumi Hayaoka, Akio Masui
  • Patent number: 4923995
    Abstract: Substituted N-arylsulfonyl-N'-pyrimidinylureas and N-arylsulfonyl-N'-triazinylureas of the general formula ##STR1## wherein R.sup.1 is a ##STR2## radical, R.sup.2 is hydrogen, halogen, nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or --COOR.sup.9,R.sup.3 is hydrogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy,R.sup.4 and R.sup.5 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.3 -C.sub.6 cycloalkyl or --NR.sup.10 R.sup.11,R.sup.6 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sup.7 is hydrogen or methyl,R.sup.8 is C.sub.4 -C.sub.6 cycloalkanonyl which is unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl or halogen; C.sub.3 -C.sub.6 cycloalkyl which is unsubstituted or substituted by one or more identical or different members selected from the group consisting of C.sub.1 -C.sub.3 alkyl, C.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: May 8, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Mayer, Werner Fory
  • Patent number: 4920225
    Abstract: Optically active compounds of formula 1 ##STR1## wherein R.sub.1 is H or lower alkyl;R.sub.2 and R.sub.6 are each independently lower alkyl, aryl, or arylalkyl;R.sub.3 is CN, NO.sub.2, CO.sub.2 R.sub.5, CONHR.sub.5, SO.sub.2 R.sub.5, or P(O)(OR.sub.5).sub.2, where R.sub.5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl;R.sub.4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO.sub.2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF.sub.3, OCH.sub.2 F, or OCF.sub.3 ;are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: April 24, 1990
    Assignee: Laboratoires Syntex S.A.
    Inventor: Gilles Genain
  • Patent number: 4863938
    Abstract: Pyridine derivatives of the formula ##STR1## their tautomers and their salts, in which R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and n have the meanings given in the claims, can be used as active ingredients in medicaments and are manufactured in a manner known per se.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: September 5, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Georg von Sprecher, Peter Waldmeier
  • Patent number: 4845108
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrines of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: February 17, 1987
    Date of Patent: July 4, 1989
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach
  • Patent number: 4826531
    Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4791123
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: January 22, 1987
    Date of Patent: December 13, 1988
    Assignee: Schering Akt.
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: 4789744
    Abstract: A process for the effective analytical or preparative resolution of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(4-aryloxyphenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric terpene esters by reaction with an optically active terpene alcohol and separating the diastereomers of the terpene ester by liquid chromatography with a silica column.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: December 6, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4786732
    Abstract: A method for the effective chromatographic resolution and analysis of the enantiomers of 2-(4-aryloxyphenoxy)propionic acids which comprises dissolving a 2-(4-aryloxyphenoxy)propionic acid in a suitable solvent, injecting the solution into a liquid chromatographic system and eluting the components from the column using an eluent contain R-(-)- or S-(+)-2-pyrrolidinemethanol and an alkanoic acid in a suitable solvent.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4786731
    Abstract: A method for the chromatographic resolution and analysis of the enantiomers of 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof which comprises converting a racemic or partially resolved mixture of said 2-(phenyl or phenoxy)propionic acids or the C.sub.1 -C.sub.4 alkyl esters thereof to a pair of diastereomeric 2-amino-1-alkanol derivatives by reaction with an optically active 2-amino-1-alkanol, and analyzing the diastereomeric mixture by gas chromatography.
    Type: Grant
    Filed: August 5, 1987
    Date of Patent: November 22, 1988
    Assignee: The Dow Chemical Company
    Inventor: John W. Russell
  • Patent number: 4761480
    Abstract: Potent dopamine-.beta.-hydroxylase inhibitors having the Formula: ##STR1## which are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmaceutical compositions including these inhibitors, and methods of using these inhibitors to inhibit dopamine-.beta.-hydroxylase activity in mammals. Also disclosed are novel intermediates useful in preparing the presently invented inhibitors.
    Type: Grant
    Filed: October 7, 1986
    Date of Patent: August 2, 1988
    Assignee: SmithKline Beckman Corporation
    Inventors: Carl Kaiser, Lawrence I. Kruse, Stephen T. Ross
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4739070
    Abstract: 2- and 4-(Dichloromethyl)pyridines containing electron withdrawing substituents on the ring are prepared by the reaction of the corresponding 2- or 4-halopyridines with excess chloroform in the presence of a strong base in a medium containing a dipolar aprotic solvent or a phase transfer catalyst. 3-Chloro-5-(trifluoromethyl)-2-(dichloromethyl)pyridine, for example, is prepared by the reaction of 2,3-dichloro-5-(trifluoromethyl)pyridine with chloroform in the presence of sodium hydroxide and N-methylpyrrolidone. Substituted 2-(dichloromethyl)pyridines are useful as agricultural pesticides and as intermediates for the preparation of agricultural pesticides.
    Type: Grant
    Filed: April 23, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4670045
    Abstract: 6-Halo(or CF.sub.3)-4-((di- or tri)halomethyl)-2-pyridinyl esters of carboxylic, carbonic, carbamic, thiocarbamic, sulfonic, or sulfamic acids, exemplified by 6-chloro-4-(trichloromethyl)-2-pyridinyl pentanoate, 4-methylbenzenesulfonate or methylcarbamate, are novel and are useful in the protection of plants from attack by soil-borne fungi.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: June 2, 1987
    Assignee: The Dow Chemical Company
    Inventors: Robert J. Ehr, Helen K. Tobol, Lillian H. Troxell
  • Patent number: 4666928
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrines of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic and anti-inflammatory agents.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: May 19, 1987
    Assignee: Merck Frosst Canada, Ind.
    Inventors: Robert N. Young, Joshua Rokach
  • Patent number: 4655824
    Abstract: Compounds of the formula ##STR1## wherein W and X, which may be identical to or different from each other, are each hydrogen, fluorine, chlorine, bromine, iodine, nitro, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Y is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms or chloro-substituted alkyl of 1 to 4 carbon atoms;Z is fluorine, chlorine, bromine, alkyl of 1 to 4 carbon atoms, fluoro-substituted alkyl of 1 to 4 carbon atoms, chloro-substituted alkyl of 1 to 4 carbon atoms, --COOH or --COO-(alkyl of 1 to 4 carbon atoms); and n is 0 or 1;and, when Z is COOH, salts thereof, especially their alkali metal salts. The compounds as well as the salts are useful as selective herbicides.
    Type: Grant
    Filed: June 13, 1984
    Date of Patent: April 7, 1987
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Rudolf Mengel, Ludwig Schroder, Werner Stransky, Gerbert Linden, Sigmund Lust
  • Patent number: 4652574
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is C.sub.1 -C.sub.12 alkyl, R.sup.2 is C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted with halogen, X is halogen, m is 0, 1 or 2 and n is 0, 1 or 2,a process for producing said compound and use thereof as an insecticide acaricide and nematicide.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: March 24, 1987
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shoichi Kato, Shizuo Shimano, Tatsumi Hayaoka, Akio Masui
  • Patent number: 4647569
    Abstract: Pyridylaminoethene derivatives of the formula: ##STR1## wherein R.sup.1 is pyridyl, unsubstituted or substituted by one or more substituents R.sup.4 selected from halogen, amino, carboxy, cyano nitro, hydroxy, formyl, trifluoromethyl, aryl, aryloxy, arylthio, benzyloxycarbonylamino, sulphamoyl, tetrazol-5-yl, carbamoyl, thiocarbamoyl, arylcarbamoyl, aroyl, alkyl, alkoxy, alkylthio, alkylsulphonyl, alkylamino, alkylsulphamoyl, arylalkyl, alkanoyl, alkoxycarbonyl, alkoxycarbonylamino, alkylcarbamoyl, alkanoylamino, N-benzyloxycarbonyl-N-alkylamino, or dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl, wherein the alkyl groups may together form a ring, and R.sup.2 and R.sup.3 each represents phenyl, unsubstituted or substituted by one or more substituents R.sup.4 as hereinbefore defined, possess antiarthritic properties.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: March 3, 1987
    Assignee: May & Baker Limited
    Inventors: Raymond F. Collins, Philip Knowles, Libert C. Saunders, Francis J. Tierney, Peter J. Warne
  • Patent number: 4634711
    Abstract: Potent dopamine-.beta.-hydroxylase inhibitors having the formula: ##STR1## which are useful to inhibit dopamine-.beta.-hydroxylase activity, pharmaceutical compositions including these inhibitors, and methods of using these inhibitors to inhibit dopamine-.beta.-hydroxylase activity in mammals. Also disclosed are novel intermediates useful in preparing the presently invented inhibitors.
    Type: Grant
    Filed: August 2, 1985
    Date of Patent: January 6, 1987
    Assignee: Smithkline Beckman Corporation
    Inventors: Carl Kaiser, Lawrence I. Kruse, Stephen T. Ross
  • Patent number: 4631081
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Z is selected from oxygen and the group --YAn wherein Y is selected from C.sub.1 to C.sub.6 alkyl and benzyl and An is an anion;k is zero or the integer 1;n is an integer selected from 3 and 4;X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.
    Type: Grant
    Filed: September 27, 1983
    Date of Patent: December 23, 1986
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Richard J. Conway, Peter G. Tucker
  • Patent number: 4586953
    Abstract: Herbicidal pyridine compounds of the formula (I): ##STR1## wherein Z may be halogen, or a fluorine- or chlorine-substituted alkyl group of 1 to 4 carbon atoms, and Y may be hydrogen, halogen, or a fluorine- or chlorine-substituted alkyl group of 1 to 4 carbon atoms; X may be an OH group or an acyloxy group; a halogen atom; an amino group, a mono- or di-alkyl amino group, or an alkanoylamido group; an alkoxy group optionally substituted by hydroxy or alkoxy; or a mercapto group, an alkylthio group, or a phenylthio group. The invention also provides herbicidal compositions containing the compounds, and processes for making the compounds.
    Type: Grant
    Filed: January 31, 1984
    Date of Patent: May 6, 1986
    Assignee: Imperial Chemical Industries PLC
    Inventor: David Cartwright
  • Patent number: 4547506
    Abstract: Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: December 20, 1983
    Date of Patent: October 15, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: Robert J. Ife
  • Patent number: 4540578
    Abstract: Novel phenoxyphenyl and phenoxypyridyl benzoyl ureas and a process for their preparation are provided. The novel ureas are useful as the active toxicant in pesticidal compositions.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: September 10, 1985
    Assignee: Union Carbide Corporation
    Inventors: David T. Chou, John A. Durden, Themistocles D. J. D'Silva
  • Patent number: 4508561
    Abstract: 1-Phenylethyl sulfone derivatives substituted by a halogenated alkyloxy group is represented by the general formula ##STR1## where R is an alkyl group substituted by a halogen atom, n is 1 or 2, each of P and Q is a hydrogen atom or a lower alkyl group and each of X and Y is a hydrogen atom, a lower alkyl group or a halogen atom. The compounds are effective as a herbicide. Also disclosed is a process for their preparation.
    Type: Grant
    Filed: January 12, 1983
    Date of Patent: April 2, 1985
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Gozyo Sakata, Tatsuo Numata, Kenzi Makino, Takuya Kakuta, Kazuya Kusano, Takasi Ikai, Tosihiko Oguti
  • Patent number: 4508562
    Abstract: Benzylsulfinyl pyridine-N-oxides represented by the formula: ##STR1## wherein X is a chlorine atom or a bromine atom; and Y and Z, which may be the same or different, are each a chlorine atom or a fluorine atom, is disclosed. A process for producing the same, and a herbicide containing the same as an active ingredient are also disclosed.
    Type: Grant
    Filed: May 27, 1983
    Date of Patent: April 2, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Nakayama, Ryo Yoshida, Hiroshi Matsumoto
  • Patent number: 4443456
    Abstract: This invention relates to a novel class of amidinourea and amidinothiourea compounds wherein the urea nitrogen atom is substituted by a heterocyclic alkylene group, and their use in pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anesthetic, anti-arrhythmic, antidiarrheal and antiparasitic action.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: April 17, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: George H. Douglas, William L. Studt, Stuart A. Dodson, Harry K. Zimmerman
  • Patent number: 4435207
    Abstract: Oxime ester compounds of the formula ##STR1## wherein A is one of the groups ##STR2## wherein B is --CH.dbd. or nitrogen and R.sub.1 is one of the groups ##STR3## wherein R.sub.2 -R.sub.7, m and n are as hereinafter set forth, processes for their preparation, herbicidal compositions containing these compounds as the active ingredient and methods of use of the herbicidal compositions are disclosed.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: March 6, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Georg Frater, Milos Suchy, Jean Wenger, Paul Winternitz
  • Patent number: 4412856
    Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • Patent number: 4379937
    Abstract: An improved process for selectively N-acylating hydroxy-amino-arylsulfonic acids is disclosed wherein the hydroxy-amino-arylsulfonic acid is dissolved in water by treatment with an alkaline lithium salt, such as lithium hydroxide, and the acylation is conducted while maintaining the pH at about 3-6. The N-acyl-hydroxy-amino-arylsulfonic acids are useful as dyestuff precursors.
    Type: Grant
    Filed: September 23, 1981
    Date of Patent: April 12, 1983
    Assignee: American Hoechst Corporation
    Inventors: Anthony J. Corso, Kathleen M. Colavito, Thomas S. Phillips
  • Patent number: 4312868
    Abstract: Isothiochromans are described. The compounds possess hypotensive and antipsychotic properties; methods and compositions using them are described.
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: January 26, 1982
    Assignee: The Upjohn Company
    Inventor: John M. McCall
  • Patent number: 4273706
    Abstract: Nondiffusible compounds are described having at least one releasable 2-(2-heterocyclylazo)-1-naphthol dye moiety having the formula: ##STR1## wherein: G is hydroxy, a salt thereof, or a hydrolyzable precursor thereof; or a group which together with ##STR2## is CAR, said CAR being bonded to the naphthalene group through the oxygen of said ##STR3## group; Z represents the atoms necessary to complete a heterocyclic ring;CAR represents a ballasted carrier moiety; andt is a positive integer of 1 to 2.
    Type: Grant
    Filed: September 14, 1979
    Date of Patent: June 16, 1981
    Assignee: Eastman Kodak Company
    Inventors: Derek D. Chapman, E-ming Wu
  • Patent number: 4243810
    Abstract: Novel pyridone-acetic acid derivative, viz. 3,5-dichloro-4-pyridone-1-acetic acid (I) is used as an intermediate in the production of certain cephem derivatives having anti-bacterial activity against gram-negative and gram-positive bacteria. The acid (I) is prepared by methods generally known in the art, e.g. by reacting 3,5-dichloro-4-pyridone with chloracetic acid or bromoacetic acid.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: January 6, 1981
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rolf Gericke, Werner Rogalski, Rolf Bergmann, Walter Hameister, Helmut Wahlig
  • Patent number: 4218237
    Abstract: A sulfonanilide compounds having the formula (I): ##STR1## wherein X.sub.1 is hydrogen atom, a halogen atom, methyl group or trifluoromethyl group, X.sub.2 is hydrogen atom or a halogen atom, R.sub.1 is a (C.sub.1 -C.sub.4) alkyl group or a halo(C.sub.1 -C.sub.4) alkyl group, R.sub.2 is hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, trifluoromethyl group or nitro group, R.sub.3 is hydrogen atom, --SO.sub.2 R.sub.1 group (R.sub.1 is the same as defined above), a (C.sub.2 -C.sub.4) acyl group, a (C.sub.2 -C.sub.4) acylmethyl group, a (C.sub.1 -C.sub.4) alkyl group, a (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl group or a (C.sub.3 -C.sub.4) alkenyl group, R.sub.4 is hydrogen atom or a halogen atom, and n is an integer of 0 to 2; and a salt thereof, which is useful as a herbicidal component.
    Type: Grant
    Filed: November 17, 1978
    Date of Patent: August 19, 1980
    Assignee: Ishihara Sangyo Kaisha Limited
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Fumio Kimura, Rikuo Nasu, Nobuyuki Sakashita, Shigeyuki Nishimura
  • Patent number: 4215003
    Abstract: A process of removing soil and/or stains from fabrics by immersing the fabrics in a peroxygen bleach bath containing as a peroxygen activator an heterocyclic sulfonate ester wherein the heterocyclic moiety includes a 5 to 6 membered heterocyclic ring containing 1 to 3 hetero atoms selected from the class consisting of --N--, --O-- and --S-- and the sulfonic acid is selected from the class consisting of an alkanesulfonic acid of 1 to 18 carbon atoms and an arenesulfonic acid of the benzene and naphthalene series.Also described are dry blend compositions containing the activator and peroxygen.
    Type: Grant
    Filed: November 20, 1978
    Date of Patent: July 29, 1980
    Assignee: FMC Corporation
    Inventors: Joseph H. Finley, John H. Blumbergs
  • Patent number: 4213774
    Abstract: Pridyloxy-phenoxy-propionic acid-amino-alkyl esters having a herbicidal action, their production, compositions containing them, and the use thereof are described. The esters correspond to the formula ##STR1## in which X is halogen or trifluoromethyl,Y is hydrogen, halogen or trifluoromethyl,Z is oxygen or sulfur,"alkylene" is a straight-chain or branched-chain C.sub.2 -C.sub.6 alkyl group, andQ is an amino or ammonium group.
    Type: Grant
    Filed: January 22, 1979
    Date of Patent: July 22, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schurter, Hermann Rempfler, Beat Bohner
  • Patent number: 4201567
    Abstract: Pyridine, 1-oxides, particularly 4- or 5-substituted pyridine, 1-oxides such as 2-[(1,1,2,2-tetrafluoroethyl)sulfinyl]pyridine, 1-oxide exhibit selective pre-emergence control of weeds.
    Type: Grant
    Filed: January 19, 1979
    Date of Patent: May 6, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Kyu T. Lee
  • Patent number: 4196208
    Abstract: This disclosure describes esters of 4-(monoalkylamino)benzoic acids with hydroxyalkanoic acids and derivatives, phenols, or 3-pyridinols useful as hypolipidemic agents.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: April 1, 1980
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4185106
    Abstract: A cosmetic composition comprising a content of an 1-hydroxy-2-pyridone of the general formula ##STR1## in which R.sub.1 stands for hydrogen, alkyl of 1 to 17 carbon atoms, alkenyl of 2 to 17 carbon atoms, cycloalkyl of 5 to 8 carbon atoms, bicycloalkyl of 7 to 9 carbon atoms, cycloalkyl-alkyl of 1 to 4 alkyl carbon atoms, the cycloalkyl groups being optionally substituted by alkyl groups of 1 to 4 carbon atoms, aryl, aralkyl of 1 to 4 alkyl carbon atoms, aryl-alkenyl of 2 to 4 alkenyl carbon atoms, aryloxy-alkyl or arylthio-alkyl of 1 to 4 alkyl carbon atoms, benzhydryl, phenylsulfonyl-alkyl of 1 to 4 alkyl carbon atoms, furyl or furyl-alkenyl of 2 to 4 alkenyl carbon atoms, the aryl groups being optionally substituted by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by nitro, cyano or halogen atoms, R.sub.2 stands for hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl or alkinyl of 2 to 4 carbon atoms, halogen atoms or benzyl, R.sub.
    Type: Grant
    Filed: August 15, 1975
    Date of Patent: January 22, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Dittmar, Eberhard Futterer, Gerhard Lohaus
  • Patent number: 4132784
    Abstract: Compounds are prepared which correspond to the formula ##STR1## wherein each X independently represents chloro, fluoro or bromo; X' represents hydrogen, methyl, chloro, fluoro or bromo; G represents oxygen or sulfur; Z represents oxygen, sulfur, sulfinyl or sulfonyl, with the proviso that Z is attached to the pyridine ring in only the 2 or 4 ring position; D represents cyano, nitro, trifluoromethyl, loweralkyl, loweralkoxy, loweralkylsulfonyl, loweralkylthio, or the radical ##STR2## R represents loweralkoxy, loweralkylamino or diloweralkylamino; R' represents R or phenyl; m represents an integer of from 0 to 4; n represents 0 or 1 and the sum of m + n represents an integer of from 0 to 4.The compounds have been found to be effective insect control agents.
    Type: Grant
    Filed: November 3, 1977
    Date of Patent: January 2, 1979
    Assignee: The Dow Chemical Company
    Inventor: Sudarshan K. Malhotra