Halogen Containing Patents (Class 568/588)
  • Patent number: 4496492
    Abstract: Novel antibacterially-active compound, 1,2,8,8a-cyclopropa[c]benzo[1,2-b:-4,3-b']dipyrol-4(5H)-one, prepared by a novel chemical process. This compound, as well as antibacterially-active intermediates, can be used to eradicate or control susceptible bacteria, for example, B. subtilis, K. pneumonia, S. lutea, S. aureus, and M. avium.
    Type: Grant
    Filed: July 19, 1983
    Date of Patent: January 29, 1985
    Assignee: The Upjohn Company
    Inventor: Wendell Wierenga
  • Patent number: 4491584
    Abstract: Certain compounds in which a carbon atom of a pyrrolidine or piperidine ring is bonded directly or through a methylene group to the nitrogen of a phenyl-substituted urea, and their pharmaceutically acceptable salts, are active antiarrhythmic agents.
    Type: Grant
    Filed: November 19, 1981
    Date of Patent: January 1, 1985
    Assignee: Riker Laboratories
    Inventor: Elden H. Banitt
  • Patent number: 4484940
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.1 -C.sub.8 alkyl group except isopropyl, which is useful as a herbicide.
    Type: Grant
    Filed: March 23, 1982
    Date of Patent: November 27, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 4484941
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as a herbicide.
    Type: Grant
    Filed: March 23, 1982
    Date of Patent: November 27, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 4452981
    Abstract: A condensed phenylurazol of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, Y and Z are each an oxygen atom or a sulfur atom and R is a C.sub.1 -C.sub.3 alkyl group, an allyl group or a propargyl group and n is an integer of 4 or 5, which is useful as a herbicide.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: June 5, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
  • Patent number: 4431822
    Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.
    Type: Grant
    Filed: March 23, 1982
    Date of Patent: February 14, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiromichi Oshio, Katsuzo Kamoshita
  • Patent number: 4424398
    Abstract: A process for synthesizing energetic ethers, esters and acetals is disclosed that comprises reacting certain alcohols with certain alkenes or alkynes in the presence of mercuric or mercurous sulfate. The products obtained are particularly useful as plasticizers, monomers or prepolymers for propellant binder systems.
    Type: Grant
    Filed: September 25, 1974
    Date of Patent: January 3, 1984
    Assignee: The United States of America as represented by the Secretary of the Air Force
    Inventors: Raymond R. McGuire, Robert E. Cochoy, Scott A. Shackelford
  • 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: 4413132
    Abstract: Novel antibacterially-active compound, 1,2,8,8a-cyclopropa[c]-benzo[1,2-b:-4,3-b']dipyrol-4(5H)-one, prepared by a novel chemical process. This compound, as well as antibacterially-active intermediates, can be used to eradicate or control susceptible bacteria, for example, B. subtilis, K. pneumonia, S. lutea, S. aureus, and M. avium.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: November 1, 1983
    Assignee: The Upjohn Company
    Inventor: Wendell Wierenga
  • Patent number: 4407760
    Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: October 4, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4405529
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 20, 1983
    Assignee: American Cyanamid Company
    Inventors: Jack K. Siddens, Sivaraman Raghu
  • Patent number: 4404148
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 13, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4377711
    Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: March 22, 1983
    Assignee: Rhone-Poulenc Industries
    Inventors: Isabelle Rico, Claude Wakselman
  • Patent number: 4346244
    Abstract: Chloroalkoxybenzenes are prepared by reacting a polychlorobenzene with at least one alkali metal hydroxide and an alcohol, ROH, in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O).sub.n R.sub.5 ].sub.3.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: August 24, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4291177
    Abstract: Highly pure dihalodiphenols or predetermined, statistical mixtures of unreacted, monohalo- and dihalodiphenols are obtained reacting the diphenol, which is suspended or dissolved in a suitable solvent, with a halogen while concurrently purging the reaction with a gas that is inert to the reaction.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: September 22, 1981
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles A. Wilson, II
  • Patent number: 4287125
    Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.
    Type: Grant
    Filed: June 20, 1980
    Date of Patent: September 1, 1981
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4283565
    Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.
    Type: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4282391
    Abstract: A continuous process for obtaining highly pure, high molecular weight aromatic polycarbonates from highly pure, halogenated diphenols.
    Type: Grant
    Filed: December 10, 1979
    Date of Patent: August 4, 1981
    Assignee: General Electric Company
    Inventors: Clayton B. Quinn, Charles A. Wilson, II
  • Patent number: 4229365
    Abstract: Fluorobenzenes are manufactured by reacting substituted chlorobenzenes with potassium fluoride in the presence of catalytic amounts of cesium fluoride and in the presence of certain solvents; m-nitrofluorobenzenes and m-cyanofluorobenzenes can also be manufactured in the absence of cesium fluoride. The products are starting materials for the manufacture of dyes, pharmaceuticals and pesticides.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: October 21, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Guenter Oeser, Karl-Heinz Koenig, Dietrich Mangold
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4188346
    Abstract: A process for the dehydrohalogenation of a (polyhaloalkyl)benzene containing a benzylic halogen such as 1,3-dichloro-5-(2,4,4,4-tetrachlorobutyl)benzene by contacting the (polyhaloalkyl)benzene with a suitably active Lewis acid catalyst such as SbCl.sub.5 or TiCl.sub.4 under conditions sufficient to catalyze said dehydrohalogenation to form a (polyhaloalkenyl)benzene such as 3,5-dichloro-.alpha.-(2,2,2-trichloroethyl)styrene.
    Type: Grant
    Filed: May 18, 1978
    Date of Patent: February 12, 1980
    Assignee: The Dow Chemical Company
    Inventor: Lowell D. Markley
  • Patent number: 4187247
    Abstract: Novel 9-substituted phenyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: February 5, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4157344
    Abstract: A one-step process for the synthesis of aryl trifluoromethyl ethers by reacting phenol or certain substituted phenols with a perhalomethane and hydrogen fluoride is provided. The compounds produced by the process of this invention are useful intermediates in the production of dyestuffs and pharmaceuticals.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: June 5, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 4138404
    Abstract: Oxadiazoline derivatives of the formula: ##STR1## WHEREIN R is alkyl of 1 through 4 carbon atoms, which are useful as intermediates in the synthesis of oxadiazoline derivatives of the formula: ##STR2## WHEREIN R is as defined above the R.sub.1 is alkyl of 1 through 4 carbon atoms, possessing useful herbicidal properties, are prepared by a new process which comprises reducing the nitro group in a 5-alkyl-3-(2-nitro-4-chlorophenyl)-1,3,4-oxadiazolin-2-one of the formula: ##STR3## wherein R is as defined above to a hydroxylamino group, treating the resulting 5-alkyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one with concentrated sulphuric acid of density about 1.83 to produce the corresponding amino-phenol, and converting the amine group in the resulting 5-alkyl-3-(2-amino-4-chloro-5-hydroxyphenyl)-1,3,4-oxadiazolin-2 -one to a chlorine atom. The 5-alkyl-3-(2-hydroxylamino-4-chlorophenyl)-1,3,4-oxadiazolin-2-one intermediates are new compounds.
    Type: Grant
    Filed: July 1, 1976
    Date of Patent: February 6, 1979
    Assignee: Rhone-Poulenc S.A.
    Inventors: Jean F. Fort, Raymond Giraudon
  • Patent number: 4126623
    Abstract: There are disclosed ethers and thioethers having a benzyl or phenyl terminal group and another terminal group which is halogenated, and which ethers and thioethers exhibit juvenile hormone activity (i.e., function as inhibitors of the development of insects from their larval state to the adult state), as well as acaricide activity.Methods for preparing the ethers and thioethers are also disclosed.
    Type: Grant
    Filed: April 14, 1977
    Date of Patent: November 21, 1978
    Assignee: Montedison S.p.A.
    Inventors: Paolo Piccardi, Pietro Massardo, Angelo Longoni