Halogen Attached Directly Or Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/303)
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Patent number: 4859687Abstract: 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: GrantFiled: February 20, 1986Date of Patent: August 22, 1989Assignee: Ciba-Giegy CorporationInventor: Peter Riebli
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Patent number: 4849011Abstract: 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: GrantFiled: August 17, 1987Date of Patent: July 18, 1989Assignee: Sumitomo Chemical Company, Ltd.Inventors: Shinichi Kawamura, Yuzuru Sanemitsu, Tatsuhiro Hamada, Ryo Yoshida
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Patent number: 4847259Abstract: 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: GrantFiled: September 23, 1987Date of Patent: July 11, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
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Patent number: 4839371Abstract: 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: GrantFiled: September 17, 1987Date of Patent: June 13, 1989Assignee: SmithKline Beckman CorporationInventors: Lawrence I. Kruse, Stephen T. Ross
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Patent number: 4834904Abstract: Optically active nitrogen-containing heterocycles of the formula I according to claim 1 are suitable as components for ferroelectric liquid crystalline materials.Type: GrantFiled: December 24, 1986Date of Patent: May 30, 1989Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Joachim Krause, Rudolf Eidenschink, Klaus Bofinger, Bernhard Scheuble, Thomas Geelhaar
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Patent number: 4808762Abstract: 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: GrantFiled: September 9, 1987Date of Patent: February 28, 1989Assignee: FMC CorporationInventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
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Patent number: 4806553Abstract: 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: GrantFiled: June 18, 1987Date of Patent: February 21, 1989Assignee: Nihon Tokushu Noyaku Seizo K.K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Shoko Sasaki, Koichi Moriya, Yumi Hattori
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Patent number: 4797490Abstract: 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: GrantFiled: September 15, 1986Date of Patent: January 10, 1989Assignee: Pfizer Inc.Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
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Patent number: 4791139Abstract: 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: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4791123Abstract: 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: GrantFiled: January 22, 1987Date of Patent: December 13, 1988Assignee: Schering Akt.Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
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Patent number: 4788206Abstract: 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: GrantFiled: July 10, 1987Date of Patent: November 29, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4786646Abstract: 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: GrantFiled: July 10, 1987Date of Patent: November 22, 1988Assignee: Hoffmann-La Roche Inc.Inventors: Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
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Patent number: 4786733Abstract: 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: GrantFiled: July 9, 1987Date of Patent: November 22, 1988Assignee: Allied-Signal Inc.Inventors: Michael Van Der Puy, Richard E. Eibeck
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Patent number: 4772633Abstract: 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: GrantFiled: February 20, 1986Date of Patent: September 20, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
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Patent number: 4771059Abstract: 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: GrantFiled: August 29, 1985Date of Patent: September 13, 1988Assignee: University of FloridaInventor: Nicholas S. Bodor
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Patent number: 4756739Abstract: 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: GrantFiled: December 19, 1986Date of Patent: July 12, 1988Assignee: Hoechst AktiengesellschaftInventors: Andreas Fuss, Volker Koch
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Patent number: 4757081Abstract: 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: GrantFiled: March 26, 1987Date of Patent: July 12, 1988Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Norihisa Yonekura, Takashi Yumita, Yukio Nezu, Yoshiyuki Kojima, Shin-ichiro Maeno, Shigeharu Yaguchi
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Patent number: 4751225Abstract: 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: GrantFiled: April 21, 1987Date of Patent: June 14, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Sumio Nishida, Noritada Matsuo, Makoto Hatakoshi, Hirosi Kisida
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Patent number: 4739057Abstract: 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: GrantFiled: June 30, 1986Date of Patent: April 19, 1988Assignee: Stauffer Chemical Co.Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
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Patent number: 4731450Abstract: 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: GrantFiled: May 21, 1986Date of Patent: March 15, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Claude Wakselman, Marc Tordeux
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Patent number: 4725607Abstract: Insecticidal 1-(2,6-dihalo-4-trifluoromethylphenyl)-2-pyridones and procedures for making the same.Type: GrantFiled: September 9, 1986Date of Patent: February 16, 1988Assignee: Imperial Chemical Industries PLCInventors: Trevor R. Perrior, Michael D. Turnbull
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Patent number: 4714706Abstract: 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: GrantFiled: May 30, 1986Date of Patent: December 22, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Hirosi Kisida, Sumio Nishida, Makoto Hatakoshi
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Patent number: 4684477Abstract: 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: GrantFiled: February 27, 1986Date of Patent: August 4, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Kazunori Nigorikawa, Tetsuya Ogawa
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Patent number: 4681941Abstract: 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: GrantFiled: April 11, 1985Date of Patent: July 21, 1987Assignee: The Dow Chemical CompanyInventor: Timothy J. Adaway
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Patent number: 4681942Abstract: 3,5-Dichloro-2-pyridone is produced by chlorination starting from 6-hydroxynicotinic acid.Type: GrantFiled: June 19, 1986Date of Patent: July 21, 1987Assignee: Lonza Ltd.Inventor: Daniel Quarroz
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Patent number: 4678504Abstract: 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: GrantFiled: June 25, 1986Date of Patent: July 7, 1987Assignee: BASF AktiengesellschaftInventors: Guenter Schulz, Eberhard Ammermann, Ernst-Heinrich Pommer
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Patent number: 4672118Abstract: 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: GrantFiled: January 9, 1984Date of Patent: June 9, 1987Assignee: The Dow Chemical CompanyInventors: Thomas E. Fisk, Christopher J. Tucker
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Patent number: 4642199Abstract: 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: GrantFiled: June 13, 1985Date of Patent: February 10, 1987Assignee: Chisso CorporationInventors: Shigeru Sugimori, Kazunori Nigorikawa
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Patent number: 4595763Abstract: Aromatic hydroxyl- or thiol-containing compounds are methylated by contacting with methyl trichloroacetate at elevated temperatures in the presence of an initiator.Type: GrantFiled: June 27, 1983Date of Patent: June 17, 1986Assignee: The Dow Chemical CompanyInventors: James M. Renga, Pen-Chung Wang
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Patent number: 4594422Abstract: 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: GrantFiled: March 11, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4549901Abstract: 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: GrantFiled: February 16, 1984Date of Patent: October 29, 1985Assignee: Stauffer Chemical CompanyInventor: Donald R. James
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Patent number: 4546190Abstract: 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: GrantFiled: February 27, 1984Date of Patent: October 8, 1985Assignee: Rutgerswerke AktiengesellschaftInventors: Winfried Orth, Werner Fickert
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Patent number: 4546191Abstract: 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: GrantFiled: March 19, 1980Date of Patent: October 8, 1985Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Takahiro Haga, Kuniaki Nagatani, Kouji Hayashi
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Patent number: 4517368Abstract: 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: GrantFiled: September 6, 1983Date of Patent: May 14, 1985Assignee: The Dow Chemical CompanyInventor: Richard L. Burson
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Patent number: 4503061Abstract: Certain 2(1H)-pyridinones are cardiotonic agents. Methods for their preparation and use are disclosed.Type: GrantFiled: July 22, 1983Date of Patent: March 5, 1985Assignee: Warner-Lambert CompanyInventors: James A. Bristol, Ila Sircar
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Patent number: 4452629Abstract: 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: GrantFiled: August 19, 1982Date of Patent: June 5, 1984Inventor: El-Ahmadi I. Heiba
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Patent number: 4427672Abstract: 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: GrantFiled: July 9, 1981Date of Patent: January 24, 1984Assignee: Bayer AktiengesellschaftInventors: Udo Kraatz, Jorg Stetter, Karl H. Buchel, Paul-Ernst Frohberger, Wilhelm Brandes
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Patent number: 4419514Abstract: 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: GrantFiled: May 18, 1981Date of Patent: December 6, 1983Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
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Patent number: 4412856Abstract: 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: GrantFiled: May 22, 1981Date of Patent: November 1, 1983Assignee: Ciba-Geigy CorporationInventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
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Patent number: 4393213Abstract: 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: GrantFiled: October 26, 1981Date of Patent: July 12, 1983Assignee: Nissan Chemical Industries, Ltd.Inventors: Kiyomi Ozawa, Shigeru Ishii
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Patent number: 4370477Abstract: 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: GrantFiled: July 27, 1981Date of Patent: January 25, 1983Assignee: John Wyeth and Brother LimitedInventor: Roger Crossley
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Patent number: 4369322Abstract: 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: GrantFiled: March 9, 1981Date of Patent: January 18, 1983Assignee: Degussa AGInventors: Peter Schalke, Axel Kleemann
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Patent number: 4342770Abstract: 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: GrantFiled: June 20, 1980Date of Patent: August 3, 1982Assignee: Dow Chemical Company LimitedInventors: David P. Clifford, Robert A. Sewell
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Patent number: 4327216Abstract: 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: GrantFiled: November 24, 1980Date of Patent: April 27, 1982Assignee: Ciba-Geigy CorporationInventor: Pierre Martin
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Patent number: 4304781Abstract: 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: GrantFiled: July 21, 1980Date of Patent: December 8, 1981Assignee: John Wyeth & Brother LimitedInventor: Roger Crossley
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Patent number: 4271304Abstract: 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: GrantFiled: May 9, 1979Date of Patent: June 2, 1981Assignee: John Wyeth & Brother, Ltd.Inventors: Edwin T. Edington, Alan C. White
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Patent number: 4262001Abstract: 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: GrantFiled: April 21, 1980Date of Patent: April 14, 1981Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, John C. Van Heertum
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Patent number: 4260766Abstract: (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: GrantFiled: December 4, 1979Date of Patent: April 7, 1981Assignee: The Dow Chemical CompanyInventor: Leo R. Morris
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Patent number: 4256893Abstract: 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: GrantFiled: March 5, 1979Date of Patent: March 17, 1981Assignee: The Dow Chemical CompanyInventors: Sudarshan K. Malhotra, Michael J. Ricks
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Patent number: 4254262Abstract: 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: GrantFiled: October 12, 1979Date of Patent: March 3, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Wataro Koike, Tadashi Sasuga, Chihiro Yazawa