Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/303)
  • Patent number: 4859687
    Abstract: The described novel pyridine derivatives are those of the general formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl, benzyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3, or benzyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2 and/or CF.sub.3,R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen or C.sub.1 -C.sub.4 -alkoxy,R.sub.3, R.sub.4 and R.sub.5 independently of one another are each hydrogen, halogen, CF.sub.3, NO.sub.2, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, or phenyl substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, NO.sub.2 and/or CF.sub.3,U and V independently of one another are each C.sub.1 -C.sub.6 -alkyl, or alkyl substituted by halogen or C.sub.1 -C.sub.4 -alkoxy, or together form one of the following alkylene bridges: ##STR2## R.sub.a is hydrogen, C.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: August 22, 1989
    Assignee: Ciba-Giegy Corporation
    Inventor: Peter Riebli
  • Patent number: 4849011
    Abstract: Provided herein is a comound of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.2 alkyl group; R.sup.2 is a hydrogen atom, halogen atom, methyl group, or trifluoromethyl group at the o- or m-position; R.sup.3 is a halogen atom, methyl group, or trifluoromethyl group; and X is an oxygen or sulfur atom. It has an outstanding herbicidal effect and selectivity for crop plants and weeds. It is useful as a herbicide.
    Type: Grant
    Filed: August 17, 1987
    Date of Patent: July 18, 1989
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Shinichi Kawamura, Yuzuru Sanemitsu, Tatsuhiro Hamada, Ryo Yoshida
  • Patent number: 4847259
    Abstract: Nitrogen-containing heterocyclic compounds are represented by the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## in which R.sub.4 is a hydrogen atom, a halogen atom or a methyl group and l is an integer of 1 or 2;R.sub.2 is a hydrogen atom or a methyl group;R.sub.3 is an alkyl group, an alkoxy group, an alkenyl group or an alkenyloxy group, all of which may optionally have one or more substituents;A is either one of the following groups: ##STR3## in which R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are, the same or different, each a hydrogen atom or a methyl group, R.sub.10 is a hydrogen atom, a halogen atom or a lower alkyl group and m is an integer of 1 to 4; andX is an oxygen atom or a sulfur atom.These componds are useful as insecticidal agents.
    Type: Grant
    Filed: September 23, 1987
    Date of Patent: July 11, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
  • Patent number: 4839371
    Abstract: Disclosed are novel substituted 3-aralkyl-2-mercaptopyridines of the structure: ##STR1## processes for their preparation, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy in particular as dopamine-.beta.-hydroxylase inhibitors.
    Type: Grant
    Filed: September 17, 1987
    Date of Patent: June 13, 1989
    Assignee: SmithKline Beckman Corporation
    Inventors: Lawrence I. Kruse, Stephen T. Ross
  • Patent number: 4834904
    Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.
    Type: Grant
    Filed: December 24, 1986
    Date of Patent: May 30, 1989
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
  • Patent number: 4808762
    Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.
    Type: Grant
    Filed: September 9, 1987
    Date of Patent: February 28, 1989
    Assignee: FMC Corporation
    Inventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
  • Patent number: 4806553
    Abstract: There are provided insecticidally active alkylenediamines of the formula ##STR1## wherein W.sup.1 stands for a 5- or 6-membered heterocyclic group which may be substituted, containing at least one hetero atom selected from, O, S and N, R.sup.1, R.sup.2 and R.sup.3 are hydrogen or alkyl and R.sup.4, X, Y and Z have the meanings as given in the specification.The new alkylenediamines can be prepared according to different preparation methods and exhibit a strong insecticidal activity.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: February 21, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
  • Patent number: 4797490
    Abstract: 6-Fluoro-7-pyridylquinolone carboxylic esters and acids having antibacterial activity are prepared by coupling of a 2-fluorophenyl-metallic compound with a pyridyl bromide or iodide in the presence of a transition metal catalyst, nitrating and hydrogenating the pyridyl-2-fluorophenyl compound formed, introducing a substituent on the nitrogen of the amine formed, and cyclizing after reacting with a dialkyl or dibenzyl ethoxymethylene malonate to form a 6-fluoro-7-pyridyl-1,4-dihydroquinol-4-one 3-carboxylate, and hydrolyzing to the corresponding acid.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: January 10, 1989
    Assignee: Pfizer Inc.
    Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
  • Patent number: 4791139
    Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.
    Type: Grant
    Filed: February 25, 1987
    Date of Patent: December 13, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Bushell, Robin A. E. Carr
  • 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: 4788206
    Abstract: Compounds of the formula ##STR1## Y is O ir S, *A is paraphenylene or *----(CH.sub.2)n----(X).sub.m --(CH.sub.2).sub.r ----, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het, aryl, R.sub.3, R.sub.4 and R.sub.8, independently, are hydrogen, lower alkyl, aryl, R.sub.5 and R.sub.6, independently, are hydrogen or lower alkyl, R.sub.7 is hydrogen, lower alkyl, cycloalkyl, Het-lower alkyl or aryl, Het is a monocyclic 5- or 6-membered hetero aromatic or a bicyclic heteroaromatic radical containing one or two hetero atoms selected from nitrogen, oxygen and sulfur, which radical may be substituted by lower alkyl, halogen or aryl, and the asterisk denotes the point of attachment,and when R.sub.6 and R.sub.7 are different, their enantiomers and racemic mixtures thereof, when R.sub.1 and R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 29, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4786646
    Abstract: The invention relates to compounds of the formula ##STR1## Y is O or S, *A is paraphenylene or *--(CH.sub.2).sub.n --(X).sub.m --(CH.sub.2).sub.r --, X is O, S or --CH.dbd.CH--, n or r, independently, are integers from 0 to 3, s is an integer from 0 to 1, m is an integer from 0 to 1, provided that when m is 1, n+s must be at least 2, R.sub.1 and R.sub.2, independently, are hydrogen, lower alkyl, cycloalkyl, lower alkenyl, Het or aryl, *E is ##STR2## or --(CH.sub.2).sub.k -- wherein k is an integer from 0 to 4, R.sub.3, R.sub.4 and R.sub.8 are independently hydrogen or lower alkyl, R.sub.5 and R.sub.6, independently are hydrogen or lower alkyl, R.sub.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: November 22, 1988
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
  • Patent number: 4786733
    Abstract: Substituted pyridine compounds particularly alkyl-substituted pyridines, are directly fluorinated to the corresponding 2-fluoro alkyl-substituted pyridines. Fluorine gas, preferably diluted with an inert gas, is passed into the substituted pyridine, preferably in a solvent, at a temperature of +25.degree. C. to -40.degree. C., preferably about -25.degree. C.
    Type: Grant
    Filed: July 9, 1987
    Date of Patent: November 22, 1988
    Assignee: Allied-Signal Inc.
    Inventors: Michael Van Der Puy, Richard E. Eibeck
  • Patent number: 4772633
    Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.
    Type: Grant
    Filed: February 20, 1986
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
  • Patent number: 4771059
    Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## X.sup.-, wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: August 29, 1985
    Date of Patent: September 13, 1988
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 4756739
    Abstract: The compounds of the formula I ##STR1## in which A denotes N or N.fwdarw.O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R.sup.1 denotes hydrogen, halogen, amino, --NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N--, Y.sup.1 Y.sup.2 C.dbd.N--, Y.sup.3 NH-- or ##STR2## K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH.sub.2, (R.sup.1).sub.n denotes at least one radical of the formula ##STR3## or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Fuss, Volker Koch
  • Patent number: 4757081
    Abstract: New substituted derivatives of 1,2,6-triphenyl-4(1H)-pyridinone are now provided, which are useful as fungicidal agent having practically valuable and improved fungicidal activities against a variety of phyto-pathogenic microorganisms, especially fungi and which show low toxicity to animals, including humans. These new compounds may be produced by different processes.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: July 12, 1988
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Norihisa Yonekura, Takashi Yumita, Yukio Nezu, Yoshiyuki Kojima, Shin-ichiro Maeno, Shigeharu Yaguchi
  • Patent number: 4751225
    Abstract: A nitrogen-containing heterocyclic compound of the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and R.sub.17 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, a trifluoromethyl group or a nitro group, R.sub.18, R.sub.19, R.sub.20 and R.sub.21 are, the same or different, each a hydrogen atom or a methyl group, k is an integer of 0 to 1 and l is an integer of 0 to 3);R.sub.2 and R.sub.3 are, the same or different, each a hydrogen atom, a halogen atom or a methyl group;R.sub.4 is a halogen atom or a methyl group;R.sub.5 and R.sub.6 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.1 -C.sub.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: June 14, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sumio Nishida, Noritada Matsuo, Makoto Hatakoshi, Hirosi Kisida
  • 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: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4725607
    Abstract: Insecticidal 1-(2,6-dihalo-4-trifluoromethylphenyl)-2-pyridones and procedures for making the same.
    Type: Grant
    Filed: September 9, 1986
    Date of Patent: February 16, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Trevor R. Perrior, Michael D. Turnbull
  • Patent number: 4714706
    Abstract: Nitrogen-containing heterocyclic compounds are represented by the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.4 is a hydrogen atom, a halogen atom or a methyl group and l is an integer of 1 or 2);R.sub.2 is a hydrogen atom or a methyl group;R.sub.3 is an alkyl group, an alkoxy group, an alkenyl group or an alkenyloxy group, all of which may have optionally one or more substituents;A is either one of the following groups: ##STR3## (in which R.sub.5, R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are, the same or different, each a hydrogen atom or a methyl group,R.sub.10 is a hydrogen atom, a halogen atom or a lower alkyl group and m is an integer of 1 to 4); andX is an oxygen atom or a sulfur atom,which is useful as an insecticidal agent.
    Type: Grant
    Filed: May 30, 1986
    Date of Patent: December 22, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
  • Patent number: 4684477
    Abstract: A novel pyridine derivative which, when added to liquid crystal substances, can improve various specific features required for the resulting liquid crystal compositions, and a liquid crystal composition containing the same are provided, which pyridine derivative is expressed by the formula ##STR1## wherein W represents H or F; X, F, Cl or alkyl or alkoxy of 1.about.10 C; ##STR2## n, 0 or 1; Y, CN or alkyl or alkoxy of 1.about.10 C; Z, F, Cl or H; and when Z is F or Cl, Y is limited to CN, excluding certain identified compounds.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: August 4, 1987
    Assignee: Chisso Corporation
    Inventors: Shigeru Sugimori, Kazunori Nigorikawa, Tetsuya Ogawa
  • Patent number: 4681941
    Abstract: An improved method of preparing aryloxyphenoxy propanoic acid esters is disclosed. Low-water levels and low temperatures increase the yield and decrease by-product formation. A hindered non-nucleophilic phenol, which is converted in situ to the phenate form, is added to the reaction mixture to drive the reaction to 99+% conversion.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: July 21, 1987
    Assignee: The Dow Chemical Company
    Inventor: Timothy J. Adaway
  • Patent number: 4681942
    Abstract: 3,5-Dichloro-2-pyridone is produced by chlorination starting from 6-hydroxynicotinic acid.
    Type: Grant
    Filed: June 19, 1986
    Date of Patent: July 21, 1987
    Assignee: Lonza Ltd.
    Inventor: Daniel Quarroz
  • Patent number: 4678504
    Abstract: O-substituted 3-oxypyridinium salts of the formula ##STR1## where R.sup.1 is unsubstituted alkyl, alkenyl or alkynyl, or is aralkyl, R.sup.3 is hydrogen, alkyl, alkenyl or alkoxy, R.sup.2 is substituted or unsubstituted alkyl, alkenyl or alkynyl, or is aralkyl, and X.sup..crclbar. is an anion, and fungicides for crop protection containing these compounds.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: July 7, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Schulz, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4672118
    Abstract: Corrosion of metal surfaces in contact with an aqueous medium is inhibited by incorporating a N-(hydrophobe aromatic)pyridinium compound such as N-(p-dodecylphenyl)-2,4,6-trimethylpyridinium sulfoacetate into the aqueous medium.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: June 9, 1987
    Assignee: The Dow Chemical Company
    Inventors: Thomas E. Fisk, Christopher J. Tucker
  • Patent number: 4642199
    Abstract: A novel pyridine derivative capable of increasing the dielectric anisotropy value (.DELTA..epsilon.) or optical anisotropy value (.DELTA.n) of liquid crystal compositions including the derivative and lowering the driving voltages of liquid crystal display elements using the composition, and also a liquid crystal composition containing the pyridine derivative are provided, which pyridine derivative is expressed by the formulaR--X--COO--Y--CH.sub.2 CH.sub.2 --Z--Awherein R represents an alkyl group or an alkoxy group each of 1-10 carbon atoms; X represents ##STR1## Y represents ##STR2## when Y is ##STR3## Z represents ##STR4## and A represents F, Cl or cyano group; and when Y is ##STR5## Z represents ##STR6## and A represents an alkyl group or an alkoxy group each of 1-10 carbon atoms.
    Type: Grant
    Filed: June 13, 1985
    Date of Patent: February 10, 1987
    Assignee: Chisso Corporation
    Inventors: Shigeru Sugimori, Kazunori Nigorikawa
  • Patent number: 4595763
    Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: June 17, 1986
    Assignee: The Dow Chemical Company
    Inventors: James M. Renga, Pen-Chung Wang
  • Patent number: 4594422
    Abstract: The invention relates to a method for selective halogenation of 6-hydroxy picoline derivatives such as 6-hydroxy picolinic acid and 6-hydroxy picoline. When 6-hydroxy picolinic acid is halogenated by allowing it to stand in an aqueous mineral acid solution for a sufficient period to replace the halo substituent with a hydroxy substituent, and then halogenated, an improved yield of the 3-halo, 6-hydroxy picolinic acid to the 5-halo 6-hydroxy picolinic acid is obtained.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4549901
    Abstract: As new compounds, 2-[4-(substituted aryloxy)phenoxy]-N-substituted phenylsulfonyl]propionamides having the formula ##STR1## wherein A is CH, or nitrogen, X is hydrogen or chlorine and Ar is phenyl or substituted phenyl.
    Type: Grant
    Filed: February 16, 1984
    Date of Patent: October 29, 1985
    Assignee: Stauffer Chemical Company
    Inventor: Donald R. James
  • Patent number: 4546190
    Abstract: The compound 3,5,6-trichloro-1H-pyridine-2-on can be produced in technical quantities by passing chlorine gas into the gas space above a solution of 6-chloro-1H-pyridine-2-on in an aqueous carboxylic acid solution and maintaining the reaction temperature between 15.degree. and 30.degree. C. This method permits the production of 3,5,6-trichloro-1H-pyridine-2-on in a one-step process from 2-chloro-6-methoxypyridine.
    Type: Grant
    Filed: February 27, 1984
    Date of Patent: October 8, 1985
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Winfried Orth, Werner Fickert
  • Patent number: 4546191
    Abstract: A trifluoromethyl-2-(thio)pyridone compound having the formula: ##STR1## wherein X represents a hydrogen atom or a halogen atom, Y.sub.1 and Y.sub.2 each represents a hydrogen atom, a halogen atom or a trifluoromethyl group, and Z represents an oxygen atom or a sulfur atom, in which either Y.sub.1 or Y.sub.2 represents a trifluoromethyl group, and when X and Y.sub.2, or X and Y.sub.1 represent a hydrogen atom at the same time, then Z represents a sulfur atom,and a process for preparing the same.
    Type: Grant
    Filed: March 19, 1980
    Date of Patent: October 8, 1985
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Takahiro Haga, Kuniaki Nagatani, Kouji Hayashi
  • Patent number: 4517368
    Abstract: The novel compound 2,3-dichloro-5-iodopyridine is prepared by chlorinating 3-chloro-5-iodo-2-pyridinol or by lithiating 2-bromo-2,3-dichloropyridine at a reduced temperature and thereafter iodinating the thus produced lithiopyridine. The compound 2,3-dichloro-5-iodopyridine is useful as a chemical intermediate in the preparation of pyridyloxyphenoxypropionic acids, and esters and amides thereof, which are valuable herbicides. The 2,3-dichloro-5-lithiopyridine and 3-chloro-5-iodo-2-pyridinol intermediates are also novel.
    Type: Grant
    Filed: September 6, 1983
    Date of Patent: May 14, 1985
    Assignee: The Dow Chemical Company
    Inventor: Richard L. Burson
  • Patent number: 4503061
    Abstract: Certain 2(1H)-pyridinones are cardiotonic agents. Methods for their preparation and use are disclosed.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: March 5, 1985
    Assignee: Warner-Lambert Company
    Inventors: James A. Bristol, Ila Sircar
  • Patent number: 4452629
    Abstract: N,N'(thio)-5(substituted-phenoxy or pyridyloxy)-2-substituted benzoic acid sulphonamide and sulfamidoyl fluoride their preparation and use as herbicides are disclosed.
    Type: Grant
    Filed: August 19, 1982
    Date of Patent: June 5, 1984
    Inventor: El-Ahmadi I. Heiba
  • Patent number: 4427672
    Abstract: Substituted triazolylalkyl pyridyl ethers of the formula ##STR1## in which R.sup.1 is a halogen atom,R.sup.2 is a hydrogen or halogen atom,X is a keto group or a CH(OH) group,Y each independently is a halogen atom or an alkyl, alkoxy or cyano group, andn is 0, 1, 2, 3 or 4,or an addition product thereof with a physiologically acceptable acid or metal salt which possesses fungicidal activity. Intermediates therefor wherein X is a keto group and with a halogen atom in place of either the pyridinyloxy group or the azole group are also new.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: January 24, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Udo Kraatz, Jorg Stetter, Karl H. Buchel, Paul-Ernst Frohberger, Wilhelm Brandes
  • Patent number: 4419514
    Abstract: Method for converting carboxylic acid groups to trichloromethyl groups which comprises contacting a compound containing a carboxylic acid group with a phenylphosphonic dichloride and phosphorus pentachloride and recovering the thus produced product.
    Type: Grant
    Filed: May 18, 1981
    Date of Patent: December 6, 1983
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
  • 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: 4393213
    Abstract: A process for producing 6-phenoxypicolinic aldehydes, which comprises reacting a 2-halogeno-6-phenoxypyridine represented by the general formula I: ##STR1## where X is a halogen atom, Y is independently an alkyl group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms, an alkoxy group of 1 to 4 carbon atoms substituted by a halogen atom, an alkylthio group of 1 to 4 carbon atoms, a trifluoromethyl group, a fluorine atom or a chlorine atom, Z is a hydrogen atom or a fluorine atom, and n is an integer of 0 to 2, with magnesium metal, and then with a formylating reagent. These compounds are used as intermediates for the synthesis of insecticides.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: July 12, 1983
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kiyomi Ozawa, Shigeru Ishii
  • Patent number: 4370477
    Abstract: The invention concerns the treatment of ulcers and hypersecretion in a mammal using compounds of the formula IAr--A--S--Y Iwhere Ar is phenyl, which may be substituted or cycloalkyl of 5 to 7 carbon atoms, A is saturated or unsaturated lower alkylene which may be substituted by lower alkyl, oxo or hydroxy, 5 is sulphur and Y is an optionally substituted pyridine, pyridinium, tetrahydropyridine or tetrahydropyridinium radical. Certain novel compounds and pharmaceutical compositions are also claimed.
    Type: Grant
    Filed: July 27, 1981
    Date of Patent: January 25, 1983
    Assignee: John Wyeth and Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4369322
    Abstract: The known synthesis for the production of aromatic substituted acetonitriles by reaction of aromatic substances with cyanogen chloride in the gas phase is improved by feeding the starting materials in gaseous form and separated from each other into the reactor. The process can be used to synthesize in general aromatic and especially hetero-aromatic substituted acetonitrile.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: January 18, 1983
    Assignee: Degussa AG
    Inventors: Peter Schalke, Axel Kleemann
  • Patent number: 4342770
    Abstract: Optionally active isomers of substituted pyridine methyl esters of cyclopropane carboxylic acids thereof are prepared and have been found to exhibit a higher degree of insecticidal activity than their unresolved parents and compositions containing said compounds are so employed as insecticides.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: August 3, 1982
    Assignee: Dow Chemical Company Limited
    Inventors: David P. Clifford, Robert A. Sewell
  • Patent number: 4327216
    Abstract: 2,3,5,6-Tetrachloropyridine and/or 3,5,6-trichloropyridin-2-ol can be obtained, using a simple novel process, by reacting trichloroacetyl chloride, in the presence of a catalyst, for example copper (I) chloride or -bromide, with acrylonitrile. 2,3,5,6-Tetrachloropyridine and 3,5,6-trichloropyridin-2-ol are suitable for producing various active substances, particularly for producing insecticides, herbicides and fungicides.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: April 27, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4304781
    Abstract: The invention concerns the treatment of ulcers and hypersecretion in a mammal using compounds of the formula IAr--A--S--Y Iwhere Ar is phenyl, which may be substituted or cycloalkyl of 5 to 7 carbon atoms, A is saturated or unsaturated lower alkylene which may be substituted by lower alkyl, oxo or hydroxy, S is sulphur and Y is an optionally substituted pyridine, pyridinium, tetrahydropyridine or tetrahydropyridinium radical. Certain novel compounds and pharmaceutical compositions are also disclosed.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: December 8, 1981
    Assignee: John Wyeth & Brother Limited
    Inventor: Roger Crossley
  • Patent number: 4271304
    Abstract: Pyridine derivatives having the formula ##STR1## and their N-oxides and pharmaceutically acceptable acid addition salts, wherein R.sup.1 and R.sup.2 are independently aryl, R.sup.3 is hydrogen or lower alkyl and n is 0, 1 or 2, have CNS activity and may be used as antidepressants.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: June 2, 1981
    Assignee: John Wyeth & Brother, Ltd.
    Inventors: Edwin T. Edington, Alan C. White
  • Patent number: 4262001
    Abstract: Substituted pyridine methyl esters of 2-isopropyl-2-(4-chlorophenyl)acetic acid are prepared which correspond to the formula: ##STR1## wherein n represents an integer of 0 to 2; X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, nitro, cyano, chloro, fluoro, bromo, or 3,4-methylenedioxy (when n is 2 and both X's are taken together); and R represents hydrogen, cyano or ethynyl. These compounds have been found to exhibit a high degree of insecticidal activity and compositions containing said compounds are so employed.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: April 14, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, John C. Van Heertum
  • Patent number: 4260766
    Abstract: (Dichloromethyl) substituted pyridines are prepared from (trichloromethyl) substituted pyridines by the reaction thereof under reductive dechlorination conditions with metallic iron or a ferrous iron compound and an acid.
    Type: Grant
    Filed: December 4, 1979
    Date of Patent: April 7, 1981
    Assignee: The Dow Chemical Company
    Inventor: Leo R. Morris
  • Patent number: 4256893
    Abstract: Substituted phenoxy and phenylthio pyridine methanols and substituted methanols are prepared which correspond to the formula: ##STR1## wherein X independently represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo; n represents an integer of 0 to 2; Y represents oxygen or sulfur and R represents hydrogen, cyano or ethynyl. These compounds are employed as intermediates in the preparation of compounds which have a high degree of insecticidal activity.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: March 17, 1981
    Assignee: The Dow Chemical Company
    Inventors: Sudarshan K. Malhotra, Michael J. Ricks
  • Patent number: 4254262
    Abstract: A phenoxycarboxylic acid derivative having the formula ##STR1## wherein R represents ##STR2## and X.sub.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, trifluoromethyl group, nitro group or cyano group and X.sub.2 represents a hydrogen atom, a halogen atom, a lower alkyl group, nitro group or cyano group, R' represents ##STR3## and R.sub.1 and R.sub.2 are the same and different and respectively represent hydrogen atom or a lower alkyl group, is produced by reacting a phenol compound having the formula ##STR4## with a halogen compound havingX--R'wherein X represents a halogen atom in the presence of a base. The reaction is carried out in the presence of a quarternary ammonium salt or a quaternary phosphonium salt in a nonpolar solvent.
    Type: Grant
    Filed: October 12, 1979
    Date of Patent: March 3, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa