The Compound Is Monocyclic Patents (Class 564/214)
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Patent number: 10435385Abstract: A compound represented by Formula (1): The compound can be used as insecticides.Type: GrantFiled: January 15, 2018Date of Patent: October 8, 2019Assignee: MITSUI CHEMICALS, INC.Inventors: Kei Yoshida, Takeo Wakita, Hiroyuki Katsuta, Akiyoshi Kai, Yutaka Chiba, Kiyoshi Takahashi, Hiroko Kato, Nobuyuki Kawahara, Michikazu Nomura, Hidenori Daido, Junji Maki, Shinichi Banba
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Patent number: 8884046Abstract: Compounds that are useful in the synthesis of 2-amino-4,6-dimethoxybenzamide derivatives and other benzamide compounds.Type: GrantFiled: October 9, 2013Date of Patent: November 11, 2014Assignee: Resverlogix Corp.Inventors: Mario Emilov Lozanov, Anthony Frank Skufca, Andrew George Zeiler
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Publication number: 20140243522Abstract: The present invention relates to benzoxazinones of the general formula (I) wherein the variables are defined according to the description, processes and intermediates for preparing the benzoxazinones of the formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one benzoxazinones of the formula (I) to act on plants, their seed and/or their habitat.Type: ApplicationFiled: May 2, 2014Publication date: August 28, 2014Applicant: BASF SEInventors: Matthias WITSCHEL, Trevor William NEWTON, Thomas SEITZ, Helmut WALTER, Bernd SIEVERNICH, Anja SIMON, Ricarda NIGGEWEG, Klaus GROßMANN, Liliana PARRA RAPADO, Richard Roger EVANS
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Publication number: 20140107369Abstract: Compounds that are useful in the synthesis of 2-amino-4,6-dimethoxybenzamide derivatives and other benzamide compounds.Type: ApplicationFiled: October 9, 2013Publication date: April 17, 2014Applicant: Resverlogix Corp.Inventors: Mario Emilov Lozanov, Anthony Frank Skufca, Andrew George Zeiler
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Publication number: 20140018548Abstract: A chiral hydrogenated H8-BINOL bisphosphine compound is provided, with the structure shown as the following formula (I), wherein both R1 and R2 are halogen, H or C1-C10 aliphatic group; R3 is H or C1-C10 aliphatic group; R4 is halogen, amino, nitro, H, C1-C10 aliphatic group or C1-C10 aromatic group; and X is phenyl, substituted phenyl, cyclohexyl, substituted cyclohexyl, C6-C30 aromatic group, or C6-C30 heterocyclic aromatic group containing one or more heteroatoms selected from N, S, O. The present invention further provides a catalyst for an asymmetric catalytic hydrogenation reaction which contains the compound, wherein the catalyst can produce more than 90% of enantiomers and efficiency with the turnover number of greater than 100,000 in the asymmetric hydrogenation reaction of imines.Type: ApplicationFiled: March 2, 2011Publication date: January 16, 2014Applicants: DALIAN HETEROGENEOUS CATALYST CO., LTD., YOUTH CHEMICAL CO., LTD., JIANGSU YANGNONG CHEMICAL CO., LTD.Inventor: Jin Li
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Publication number: 20140012027Abstract: A method for producing a fluorine-containing substituted compound, the method including: introducing an organofluorine compound and an organolithium compound into a microreactor provided with a flow path capable of mixing a plurality of liquids, to thereby obtain a reaction product; and introducing, into the microreactor, the reaction product and an electrophile exhibiting electrophilic effect on the reaction product, to thereby obtain a fluorine-containing substituted compound.Type: ApplicationFiled: September 9, 2013Publication date: January 9, 2014Applicants: Taiyo Nippon Sanso Corporation, Kyoto UniversityInventors: Junichi YOSHIDA, Aiichiro NAGAKI
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Publication number: 20130157857Abstract: The present invention relates to an inhibitor for tobacco axillary bud growth, the inhibitor comprising, as an active ingredient, one or more kinds of very-long chain fatty acid synthesis inhibitors such as a chloroacetamide-based herbicide, fentrazamide, cafenstrole or indanofan; an inhibitor for tobacco axillary bud growth, the inhibitor comprising the aforesaid very-long chain fatty acid synthesis inhibitor together with clorthal-dimethyl or an aliphatic alcohol having 6 to 20 carbon atoms; and a method for inhibiting tobacco axillary bud growth which comprises applying the inhibitor for tobacco axillary bud growth. The inhibitor for tobacco axillary bud growth of the present invention shows sustained drug efficacy at a low concentration, induces neither chemical injury nor disease, and can contribute to the improvement in labor productivity.Type: ApplicationFiled: July 26, 2011Publication date: June 20, 2013Applicant: SDS BIOTECH K.K.Inventors: Motoki Tanaka, Keijitsu Tanaka, Takeshi Shibuya, Eiji Ikuta, Kotaro Yoshinaga, Yuki Yamaguchi
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Publication number: 20120301880Abstract: Alkyl amine dyes, oligonucleotide probes prepared from the alkyl amine dyes, phosphoramidites and solid supports prepared from the alkyl amine dyes, and methods of labeling biological agents using the alkyl amine dyes.Type: ApplicationFiled: May 29, 2012Publication date: November 29, 2012Applicant: BLOOD CELL STORAGE, INC.Inventors: Michael W. Reed, Robert O. Dempcy
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Publication number: 20120264603Abstract: The invention encompasses formulations for increased attachment and retention systems of biologically active organic compounds and methods for the preparation and use thereof.Type: ApplicationFiled: October 7, 2011Publication date: October 18, 2012Inventors: David S. Soane, Gangadhar Jogikalmath
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Publication number: 20120232306Abstract: The present invention refers to a new process for the synthesis of tapentadol comprising the quantitative resolution of the racemic mixture (V) to obtain the stereoisomer of (S)-3-(dimethylamino)-2-methyl-1-(3-nitrophenyl)-propan-1-one (VII) according to the Scheme 2 below using the (2R,3R)—O,O?-dibenzoyltartaric chiral acid wherein said resolution is quantitative. The present invention also refers to some intermediate compounds of the new synthesis process of tapentadol.Type: ApplicationFiled: November 30, 2010Publication date: September 13, 2012Applicant: Euticals S.P.A.Inventors: Giuseppe Motta, Domenico Vergani, Giorgio Bertolini
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Publication number: 20120100991Abstract: The present invention relates to benzoxazinones of the general formula (I) wherein the variables are defined according to the description, processes and intermediates for preparing the benzoxazinones of the formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one benzoxazinones of the formula (I) to act on plants, their seed and/or their habitat.Type: ApplicationFiled: June 11, 2010Publication date: April 26, 2012Applicant: BASF SEInventors: Matthias Witschel, Trevor William Newton, Thomas Seitz, Helmut Walter, Bernd Sievernich, Anja Simon, Ricarda Niggeweg, Klaus Grossmann, Liliana Parra Rapado, Richard Roger Evans
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Publication number: 20110034461Abstract: The invention relates to novel compounds of formula I where R1, R2, R3, R4, R5, R9, Ar, Q1, Q2 and Q3 are each as defined below. The compounds of the formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The invention further relates to a process for preparing the compound of the formula I and to the use thereof as a medicament.Type: ApplicationFiled: August 5, 2010Publication date: February 10, 2011Applicant: sanofi-aventisInventors: Uwe HEINELT, Volkmar WEHNER, Matthias HERRMANN, Karl SCHOENAFINGER, Henning STEINHAGEN
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Publication number: 20090036713Abstract: The present invention relates to a process for the hydrogenation of imines with hydrogen in the presence of iridium catalysts. In particular the present invention relates to a process for the hydrogenation of imines with hydrogen under elevated pressure in the presence of an iridium catalysts and with or without an inert solvent, wherein the reaction mixture comprises a phosphonium chloride, bromide or iodide in the presence or in the absence of an acid, which can be an organic or inorganic acid, soluble or insoluble in the reaction mixture. Suitable imines are especially those that contain at least one (Formula I) group. If the groups are substituted asymmetrically and are thus compounds having a prochiral ketimine group, it is possible in the process according to the invention for mixtures of optical isomers or pure optical isomers to be formed if enantioselective or diastereoselective iridium catalysts are used.Type: ApplicationFiled: February 9, 2007Publication date: February 5, 2009Applicant: EVONIK DEGUSSA GmbHInventors: Juan Almena, Thomas Riermeier, Axel Monsees, Renat Kadyrov
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Patent number: 6566554Abstract: The present invention relates to a compound of general formula (I) wherein R1, R2, and R3 represents one or more, same or different substituents selected from the group consisting of halogen, hydroxy, mercapto, trifluoromethyl, amino, (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)akylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, cyano, —CONH2, phenyl, or nitro; further R2 can be hydrogen, and R3 can be carboxy and carbamoyl; R4 represents hydrogen, (C1-C3)alkyl, or allyl; X represents oxygen or sulphur; Q represents —(CO)—, —(CS)—, or a bond; Y represents (C5-C15)alkyl; (C2-C15)olefinic group; (C3-C10)monocyclic hydrocarbon group; or phenyl; any of which may be optionally substituted by one or more, same or different substituents selected from the group consisting of the formula R5 defined below; (C1-C4)alkyl substituted by one or more substituents selected for the group R5; or a group of the formula —(Z—O)n—Z, wherein Z is a (C1-C3)alkyl, n is anType: GrantFiled: February 22, 2002Date of Patent: May 20, 2003Assignee: Leo Pharmaceutical Products Ltd. a/s (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventor: Erik Rytter Ottosen
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Patent number: 6555710Abstract: The present invention relates to compounds of formula (I) wherein R1 and R2 independently represent one or more, same or different substituents selected from the group consisting of halogen, hydroxy, mercapto, trifluoromethyl, amino (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)alkylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, cyano, carbamoyl, phenyl, or nitro; R2 further being represented by hydrogen; R3 represents hydrogen, halogen, hydroxy, mercapto, trifluoromethyl, amino, (C1-C3)alkyl, (C2-C3)olefinic group, (C1-C3)alkoxy, (C1-C3)alkylthio, (C1-C6)alkylamino, (C1-C3)alkoxycarbonyl, phenyl, cyano, carboxy or carbomoyl; R4 represents hydrogen, (C1-C3)alkyl, or allyl; X represents oxygen or sulpher; with the proviso that formula (I) does not comprise the compound 2,2,2-trifluoro-N-[2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]-phenyl]acetamide wherein R1 is a 2-methyl, R2 is 2-chloro, R3 and R4 is hydrogen, and X is oxygen; and a salt thereof with a pharmaceutically accepType: GrantFiled: March 15, 2002Date of Patent: April 29, 2003Assignee: Leo Pharmaceutical Products Ltd a/s Lovens Kemiske Fabrik ProduktionsaktieselskabInventor: Erik Rytter Ottosen
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Patent number: 6242609Abstract: A method for manufacturing a color coupler used in a silver halide photographic light-sensitive material using an ammonium trihalide. Said method for manufacturing the color coupler comprising the following step: a step for halogenating a coupling position of a four equivalent coupler using a halogenating agent, wherein said halogenating agent is said ammonium trihalide.Type: GrantFiled: April 7, 1999Date of Patent: June 5, 2001Assignee: Konica CorporationInventor: Fumio Ishii
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Patent number: 5852215Abstract: Aromatic azomethines are produced by continuous reaction of an aniline with a formaldehyde source, with continuous evaporation to remove residual water of reaction. The azomethine product may be further reacted, either continuously or in batch process, with a haloacetylating agent, and, additionally, with an aliphatic alcohol.Type: GrantFiled: September 19, 1996Date of Patent: December 22, 1998Assignee: Zeneca LimitedInventors: Kambiz Javdani, Louie A. Nady, Ping H. Sih, Gilbert Rodriguez
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Patent number: 5831126Abstract: The invention relates to the use of the compound N-(4-fluoro-phenyl)-N-isopropyl-chloroacetamide of the formula (I) ##STR1## which is known, as active compound in selective herbicidal compositions, for example for combating weeds in maize cultures, and to a new process for the preparation of this active compound.The compound (I) is obtained in very high yields by reacting N-isopropyl-4-fluoro-aniline with approximately equimolar amounts of chloroacetyl chloride at temperatures between 20.degree. and 150.degree. C. in the presence of an inert diluent, such as, for example, toluene, without addition of an acid binder.Type: GrantFiled: January 30, 1997Date of Patent: November 3, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Heinz Forster, Thomas Schmidt, Karl Steinbeck, Markus Dollinger, Hans-Joachim Santel
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Patent number: 5668257Abstract: The present invention relates to a novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: June 7, 1995Date of Patent: September 16, 1997Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5519144Abstract: Eserethole of formula ##STR1## is prepared from 1,3-dimethyl-5-hydroxy-oxindole compound II which is acylated in the first step to obtain 1,3-dimethyl-5-acyloxyoxindole (III). The product is reacted with chloroacetonitrile to obtain 1,3-dimethyl-3-cyanomethyl-5-acyloxy-oxindole (IV). The 5-acyloxy group is hydrolyzed and the hydroxy group is ethoxylated with ethyl halides or sulfate. Then the product is cyclized by treatment with sodium bis-(methoxy-ethoxy)aluminum hydride, to give O-ethyl-nor-eseroline (VI) and the compound is methylated to give eserethole (VII).Type: GrantFiled: December 19, 1994Date of Patent: May 21, 1996Assignee: Laboratorio Chimico Internazionale S.p.A.Inventors: Aldo Belli, Giorgio Chiodini, Stefano Maiorana
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Patent number: 5430188Abstract: A process for the preparation of 2-alkyl-6-methyl-N(1'-methoxy-2'-propyl)-aniline by catalytic reductive alkylation wherein at least one mole equivalent of methoxyacetone is reacted with one mole equivalent of 2-alkyl-6-methyl-aniline in a liquid medium without an additional solvent, in the presence of a platinized carbon catalyst and hydrogen and in the presence of an acid cocatalyst under a hydrogen pressure of between 2.times.10.sup.5 and 1.times.10.sup.6 Pa at a temperature between 20.degree. and 80.degree. C., characterized in that the reaction mixture contains water from the beginning of the reaction and after the hydrogenation, base is added, the reaction mixture is filtered to separate the catalyst and the title compound recovered from the filtrate. The process is particularly useful for the preparation of N-substituted chloracetanilide herbicides.Type: GrantFiled: December 15, 1993Date of Patent: July 4, 1995Assignee: Ciba-Geigy CorporationInventors: Rolf Bader, Peter Flatt, Paul Radimerski
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Patent number: 5424405Abstract: The fibre-reactive dyes of the formula ##STR1## where the variables are each as defined in the claims, are suitable in particular for dyeing nitrogen-containing and hydroxyl-containing fibre materials.Type: GrantFiled: November 19, 1993Date of Patent: June 13, 1995Assignee: Ciba-Geigy CorporationInventors: Jean-Marie Adam, Guido Jordine
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Patent number: 5416212Abstract: An anilide compound represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent an alkyl group having 1 to 4 carbon atoms; n represents 0, 1 or 2; A represents an alkylene group having 1 to 14 carbon atoms or a group represented by --CH.sub.2 CO--; and Ar represents a phenyl group, a phenyl group substituted with a halogen atom, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkanoyl group having 2 to 5 carbon atoms or a trifluoromethyl group, a benzyl group, a pyridyl group, a pyridyl group substituted with a halogen atom or a trifluoromethyl group, or a pyrimidyl group, or a salt thereof. The disclosed anilide compounds have potent ACAT inhibitory activity.Type: GrantFiled: June 20, 1994Date of Patent: May 16, 1995Assignee: Taisho Pharmaceutical Co., Ltd.Inventors: Masakazu Sato, Masahiro Kawase, Akira Manaka, Yutaka Kawashima, Katsuo Hatayama
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Patent number: 5399759Abstract: A formaldehyde reactant is provided to a chemical process or reaction, in the form of a formaldehyde-alcohol complex, by contacting paraformaldehyde with from about 0.25 to about 3 mole equivalents of an aliphatic alcohol in the presence of a catalytic amount of a base. In a preferred embodiment the chemical process is a process for the production of an aromatic azomethine by reaction of an aniline with formaldehyde. The azomethine may then be used to produce a haloacetanilide.Type: GrantFiled: April 22, 1992Date of Patent: March 21, 1995Assignee: Imperial Chemical Industries PLCInventor: Gilbert Rodriguez
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Patent number: 5260483Abstract: Methods of producing N-aryl amides comprise reacting an aromatic isocyanate compound with substantially anhydrous carboxylic acid and recovering the resulting N-aryl amide. Additionally, or alternatively, methods of forming N-aryl amides comprise reacting an aromatic isocyanate compound with substantially anhydrous carboxylic acid in the presence of an anhydrous hydrogen halide or hydrolytically unstable halide compound and recovering the resulting N-aryl amide. These reactions may occur in the presence of an aprotic solvent.Type: GrantFiled: September 9, 1991Date of Patent: November 9, 1993Assignee: Drexel UniversityInventors: Franklin A. Davis, William E. Starner
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Patent number: 5155272Abstract: The disclosure herein concerns a new process anilides typified by 2',6'-diethyl-N-(methoxymethyl)2-chloroacetanilide (common name alachlor), by the reaction of the appropriate haloacyl amides one of which substituents has a reactive halogen atom with the appropriate alcohol or thioalcohol.Type: GrantFiled: October 4, 1990Date of Patent: October 13, 1992Assignee: Monsanto CompanyInventors: Donald E. Baldus, Edward E. Debus
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Patent number: 5068392Abstract: 2-Chloro and 2,6-dichloroanilines, optionally substituted in the 3-, 5-, and/or 6-position are prepared from the corresponding anilides by selective bromination, chlorination, reduction and hydrolysis. The selectivity of the process for introducing chlorines ortho to the amino group is very high.Type: GrantFiled: January 24, 1991Date of Patent: November 26, 1991Assignee: DowElancoInventors: Lennon H. McKendry, Mark W. Zettler
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Patent number: 5002606Abstract: The optically active mixture of isomers of aRS,1'S(-)-N-(1'-methyl-2'-methoxyethyl)-N-chloroacetyl-2-ethyl-6-methylan iline has improved action against problem weeds over the racemic mixture of isomers known as "Metolachlor".Type: GrantFiled: December 7, 1984Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventors: Hans Moser, Christian Vogel
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Patent number: 4994562Abstract: The fibre-reactive formazan dyes of the formula ##STR1## where B is an aliphatic or sulfo-free aromatic bridge member, R is .alpha.,.beta.-dihalopropionyl, .alpha.-haloacryloyl or haloacetyl, T.sub.1 is halogen, X is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, cyano or nitro, Y is --CO-- or --SO.sub.2 --, Z is nitrogen or --C--T.sub.2, T.sub.2 is halogen, hydrogen, C.sub.1 -C.sub.4 alkylthio, cyano, formyl or C.sub.1 -C.sub.4 alkylsulfonyl, m is 1, 2 or 3, n is 0, 1 or 2, qu is 0 or 1 and r and s are each eitehr 0 or 1 but never the same as each other, produce dyeings having good fastness properties on nitrogen-containing or hydroxyl-containing fibre materials.Type: GrantFiled: June 29, 1989Date of Patent: February 19, 1991Assignee: Ciba-Geigy CorporationInventor: Urs Lehmann
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Patent number: 4992588Abstract: O-acrylaminomethylbenzyl halides (I) ##STR1## in which X is Cl or Br and R.sup.1 is alkyl or aryl, are obtained by reacting an o-aminomethylbenzyl alkyl ether (II) ##STR2## with an acylating agent, and then reacting the resulting acid amide, preferably without intermediate isolation, with an aqueous hydrohalic acid.Type: GrantFiled: July 31, 1985Date of Patent: February 12, 1991Assignee: BASF AktiengesellschaftInventors: Josef Mueller, Walter-Weilant Wiersdorff, Werner Kirschenlohr, Gerd Schwantje
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Patent number: 4919709Abstract: The optically active isomer of S(-)-N-(1'methyl-2'-methoxyethyl)-N-chloroacetyl-2,6-dimethylaniline has improved action against problem weeds over the racemic mixture of isomers.Type: GrantFiled: December 7, 1984Date of Patent: April 24, 1990Assignee: Ciba-Geigy CorporationInventors: Hans Moser, Christian Vogel
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Patent number: 4883915Abstract: A process for the catalyzed conversion fo oximes such as cyclohexanone oxime to amides such as caprolactam via a high conversion, high selectivity, long catalyst lifetime reaction over a HAMS-1B crystalline borosilicate-based catalyst composition.Type: GrantFiled: April 8, 1987Date of Patent: November 28, 1989Assignee: Amoco CorporationInventor: Patrick E. McMahon
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Patent number: 4872902Abstract: The invention relates to the novel cyclohexanediones of formula I ##STR1## in which R is hydrogen or C.sub.1 -C.sub.6 -alkyl,A is R.sub.2, OR.sub.3 or NR.sub.3 R.sub.4,R.sub.2 is C.sub.1 -C.sub.6 -alkyl that is unsubstituted or is mono-substituted by C.sub.1 -C.sub.4 -alkoxy or mono- or poly-substituted by halogen, or is C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 is C.sub.1 -C.sub.6 -alkyl or C.sub.3 -C.sub.6 -cycloalkyl, or is phenyl or benzyl each of which is unsubstituted or is mono-, di- or tri-substituted by R.sub.5,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.3 and R.sub.4 are, in addition, together with the nitrogen atom to which they are bonded, a pyrrolidine, morpholine or piperidine radical,B is one of the radicals ##STR2## m is 0, 1, 2 or 3, R.sub.5 is halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylsulphinyl or C.sub.1 -C.sub.Type: GrantFiled: February 8, 1988Date of Patent: October 10, 1989Assignee: Ciba-Geigy CorporationInventor: Hans-Georg Brunner
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Patent number: 4873357Abstract: 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: GrantFiled: October 8, 1987Date of Patent: October 10, 1989Assignee: SmithKline Beckman CorporationInventors: Carl Kaiser, Lawrence I. Kruse, Stephen T. Ross
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Patent number: 4766243Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.Type: GrantFiled: August 10, 1984Date of Patent: August 23, 1988Assignee: Occidental Chemical CorporationInventor: Michael J. Fifolt
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Patent number: 4761176Abstract: The disclosure herein relates to a group of N-hydrocarbyloxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly sugarbeets. The herbicides herein are particularly effective against annual grasses, including hard-to-kill narrowleaf weeds such as blackgrass, wild oats, and downy brome and other prevalent grasses such as yellow foxtail, barnyardgrass, crabgrass, annual rye, etc.Type: GrantFiled: March 15, 1984Date of Patent: August 2, 1988Assignee: Monsanto CompanyInventor: Gerhard H. Alt
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Patent number: 4731109Abstract: The disclosure herein relates to a group of N-hydrocarbyloxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly, corn and soybeans and other crops including cotton, peanuts, rape and bush beans. The herbicides herein are particularly effective against hard-to-kill perennial weeds such as quackgrass and nutsedges and are also effective against annual weeds.Type: GrantFiled: March 17, 1982Date of Patent: March 15, 1988Assignee: Monsanto CompanyInventor: John P. Chupp
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Patent number: 4721797Abstract: N-acyl-N-alkyl-2,6-dialkyl-3-chloroanilines of the formula ##STR1## wherein R.sub.1 is methyl or ethyl, R.sub.2 is alkoxymethyl, chloromethyl or 2-tetrahydrofuryl, R.sub.3 is alkoxymethyl, carboxy or alkoxycarbonyl and R.sub.4 is hydrogen or methyl and, if R.sub.3 is carboxy or alkoxycarbonyl, R.sub.4 is also 2-alkoxyethyl and 2-alkoxypropyl, and R.sub.3 and R.sub.4, together with the carbon atom to which both radicals are attached, may also form a 2-oxotetrahydro-3-furyl radical or a 2-oxo-5-methyltetrahydro-3-furyl radical, are prepared by reacting a 2,6-dialkylaniline of the formula ##STR2## with a halide of the formula ##STR3## wherein X is chlorine or bromine, to give an N-alkyl-2,6-dialkylaniline of the formula ##STR4## then converting said compound by further reaction with an acylating agent of the formulaX.sub.1 --CO--R.sub.2wherein X.sub.1 is chlorine, bromine or -O-CO-R.sub.Type: GrantFiled: September 2, 1986Date of Patent: January 26, 1988Assignee: Ciba-Geigy CorporationInventors: Wolfgang Eckhardt, Hans Suess
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Patent number: 4659365Abstract: An acetanilide derivative of the following formula (I) and a herbicide containing one or more of the acetanilide derivative as the active ingredient are described. ##STR1## In the formula, R.sup.1 is a lower alkyl group; R.sup.2 is a fluorine-substituted lower alkyl group; A is ##STR2## B is an optionally substituted pyrazolyl group, an optionally substituted alkoxy group or a hydrogen atom.The acetanilide derivative and the herbicide have a selective weed killing activity to gramiveous weeds.Type: GrantFiled: August 26, 1985Date of Patent: April 21, 1987Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Kazuhiko Konno, Koichi Araki, Kaoru Ikeda, Keiji Endo, Mitsuru Hikido
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Patent number: 4647582Abstract: A compound of the formula: ##STR1## useful as a fungicidal agent against phytopathogenic fungi, and particularly against strains resistant to benzimidazole, thiophanate and/or cyclic imide fungicides.Type: GrantFiled: December 23, 1983Date of Patent: March 3, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Toshiro Kato, Hiroshi Noguchi, Yukio Oguri, Shigeo Yamamoto, Katsuzo Kamoshita
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Patent number: 4636505Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents;R.sup.3 is hydrogen or halogen;R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ;R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ;R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ;A.sup.1 and A.sup.4, the same or different, each is alkylene;A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene;X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino;R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted;and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.Type: GrantFiled: July 15, 1983Date of Patent: January 13, 1987Assignee: Imperial Chemical Industries PLCInventor: Howard Tucker
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Patent number: 4618713Abstract: This invention relates to a process for preparing 2'-methyl-2-haloacetanilides by selective catalytic hydrogenation of 2'-(halomethyl)-2-haloacetanilides. The 2'-(halomethyl)-2-haloacetanilides are initially prepared by reacting an ortho-(halomethyl) aniline or its anilinium salt with a haloacetyl halide.Type: GrantFiled: September 7, 1983Date of Patent: October 21, 1986Assignee: Monsanto CompanyInventors: John P. Chupp, Michael J. Miller
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Patent number: 4606759Abstract: The disclosure herein relates to a group of N-alkoxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly sorghum. Herbicides herein are particularly effective against hard-to-control weeds particularly seedling johnsongrass and/or shattercane, white proso millet, yellow nutsedge and redroot pigweed in addition to yellow foxtail, barnyardgrass and crabgrass.Type: GrantFiled: February 23, 1981Date of Patent: August 19, 1986Assignee: Monsanto CompanyInventor: Gerhard H. Alt
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Patent number: 4605764Abstract: The invention relates to acetamides of the formula (III), ##STR1## wherein R.sup.1 stands for a halogenated alkyl group containing 1 to 2 carbon atoms, preferably for a dichloro- or dibromoalkyl group;R.sup.2 stands for a straight or branched alkyl group containing 1 to 6 carbon atoms or an alkenyl group containing 2 to 6, preferably 3, carbon atoms;R.sup.3 stands for an alkyl group containing 1 to 6, preferably 1 to 4, carbon atoms, an alkoxyalkyl group of altogether 2 to 6, suitably 4 carbon atoms, or a phenyl group;R.sup.3 and R.sup.4 together may stand for a propylene or butylene group;R.sup.4 and R.sup.5 stand independently from each other for hydrogen or a methyl group; orR.sup.4 and R.sup.5 together may stand for a propylene or butylene group.These compounds are antidotes and can be used alone or together with herbicidal agents. The invention comprises such compositions and a process for the preparation of said compounds.Type: GrantFiled: July 13, 1983Date of Patent: August 12, 1986Assignee: Eszakmagyarorszagi VegyimuvekInventors: Gyorgy Matolosy, Barna Bordas, Antal Gimesi, Magdolna Kovacs nee Kalman, Marton Tuske
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Patent number: 4599448Abstract: N-(Alkenyl)-chloroacetanilides of the formula ##STR1## in which R.sup.1 represents a hydrogen atom or an alkyl group,R.sup.2 represents a hydrogen atom or an alkyl, alkoxy, alkoxyalkyl, hydroxyalkyl or benzyl group,R.sup.3 represents a hydrogen atom or an alkyl, alkenyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkylcarbonyl-alkyl, alkoxycarbonyl or alkoxycarbonylalkyl group, orR.sup.1 and R.sup.2, together with the C.dbd.C double bond, represent an optionally substituted mono-unsaturated or polyunsaturated ring which can also contain heteroatoms, orR.sup.2 and R.sup.3, together with the adjacent carbon atom, represent an optionally substituted, saturated or unsaturated ring which can also contain heteroatoms and/or a carbonyl group, orR.sup.2 and R.sup.3 together represent a radical of the formula ##STR2## wherein R.sup.6 represents a hydrogen atom or an alkyl group andR.sup.7 represents an alkyl or phenyl group andX.sup.1, X.sup.2 and X.sup.Type: GrantFiled: February 13, 1984Date of Patent: July 8, 1986Assignee: Bayer AktiengesellschaftInventors: Rudolf Thomas, Ludwig Eue, Robert Schmidt, Klaus Lurssen
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Patent number: 4567299Abstract: The disclosure herein relates to a group of N-methyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly soybeans. The herbicides herein are particularly effective against the hard-to-kill annual weeds Texas panicum, itchgrass, wild proso millet, alexandergrass, shattercane and seedling johnsongrass.Type: GrantFiled: December 24, 1984Date of Patent: January 28, 1986Assignee: Monsanto CompanyInventors: Gerhard H. Alt, James S. Bannon
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Patent number: 4552956Abstract: Pyrazolo, pyrimido and thiazolo[1,4]benzoxazines, useful as dopamine agonists.Type: GrantFiled: August 15, 1984Date of Patent: November 12, 1985Assignee: Eli Lilly and CompanyInventors: Richard N. Booher, Edmund C. Kornfeld
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Patent number: 4511736Abstract: The invention relates to a novel process for preparing chloroacetanilides of the formula ##STR1## wherein: R.sub.1 and R.sub.2 represent independently from each other a hydrogen atom or a C.sub.1-8 alkyl or C.sub.1-8 alkoxy group; andR.sub.3 stands for a straight chained or branched C.sub.1-8 alkoxy group.Said process is characterized by chloroacetylating a 2,6-dialkylaniline of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as defined above, at a temperature of 10.degree. to 120.degree. C., optionally in a solvent medium in the presence of an acid binding agent, then reacting a thus-obtained intermediate with chloromethyl chloroformiate or, alternatively, reacting a compound of the formula (II) first with chloromethyl chloroformiate and subjecting then to chloroacetylation, thereafter reacting a thus-obtained intermediate with an alcohol of the formulaR.sub.3 --OH (III),wherein R.sub.Type: GrantFiled: January 7, 1983Date of Patent: April 16, 1985Assignee: Eszakmagyarorszagi VegyimuvekInventors: Ferenc Mogyorodi, Eniko Koppany, Tibor Bodi, Karoly Balogh, Istvan Toth, Rezso Bognar, Sandor Makleit, Gyorgy Litkei, Miklos Rakosi, Zoltan Dinya
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Patent number: 4456471Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl or alkoxy; R.sup.2 is alkenyl having 2 to 10 carbon atoms, substituted alkyl of 1 to 10 carbon atoms or substituted alkenyl of 1 to 10 carbon atoms substituted with 1 or 2 hydroxy groups or 1 or 2 alkoxy groups of 1 to 4 carbon atoms or 1 or 2 alkenyloxy groups of 2 to 4 carbon atoms; acyl, and ketal group of the formula ##STR2## wherein n=2, 3 or 4, R.sup.4 is alkyl and R.sup.5 is hydrogen or alkyl, an oxime of the formula ##STR3## wherein R.sup.6 is hydrogen or alkyl; R.sup.3 is hydrogen or alkyl; X is halo have herbicidal activity.Type: GrantFiled: July 27, 1982Date of Patent: June 26, 1984Assignee: Chevron Research CompanyInventor: John W. Kobzina
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Patent number: 4451285Abstract: The present disclosure relates to a new class of 2-haloacetanilide derivatives which are useful as herbicides. This disclosure further relates to herbicidal compositions containing such 2-haloacetanilides and to herbicidal methods of use employing such compounds and compositions.Type: GrantFiled: May 28, 1982Date of Patent: May 29, 1984Assignee: Monsanto CompanyInventor: Gerhard H. Alt