Nitrogen Containing Patents (Class 568/30)
  • Patent number: 4946992
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formuls R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanated to prepare polyureas/polyurethanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
  • Patent number: 4931474
    Abstract: An ether derivative compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, chloro, methyl or (C.sub.1 -C.sub.3)-alkoxy, R.sup.2 is (C.sub.1 -C.sub.6)-alkyl, R.sup.3 is hydrogen, chloro, bromo, fluoro, --CF.sub.3, nitro, (C.sub.1 -C.sub.4)-alkyl, methoxy, phenoxy or (C.sub.1 -C.sub.3)-alkylthio, R.sup.4 is hydrogen, chloro or methyl, Y is oxygen, sulfur, sulfinyl, sulfonyl, or imino, x is 0, 1 or 2, y is 0 or 1, a is 0 or 1, b is an integer of 0 to 6, c is 0 or 1, d is 0, 1 or 2, e is 0 or 1, except that all of a, b and c are zero.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: June 5, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Shoichi Kato, Tatsumi Hayaoka
  • Patent number: 4909835
    Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by ahlogen, 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 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: March 20, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 4898944
    Abstract: Precursors for the preparation of fiber-reactive triphendioxazine dyestuffs correspond to the general formulas: ##STR1## in which Y' is a vinyl, a beta-hydroxyethyl or an ethyl group which contains in the beta-position a substituent which can be eliminated by an alkali;T is an optionally substituted alkyl (e.g.
    Type: Grant
    Filed: October 27, 1988
    Date of Patent: February 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunther Schwaiger, Hartmut Springer, Walter Helmling
  • Patent number: 4898981
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formula HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H prepared from halogenated neopentyl glycols and thiols of the formula R.sub.f --E--SH, or amines of the formula R.sub.f --E--NH--R wherein R.sub.f is a hydrophonic, olephobic fluoroaliphatic group of up to 20 carbon atoms, E is alkylene of up to 10 carbon atoms, optionally interrupted by up to three groups including --NR, --O, --S--, --SO.sub.2 --, --O.sub.2 C, CONR, and --SO.sub.2 NR, and X is S,SO.sub.2 or NR.sub.2, where R is independently hydrogen, alkyl, or hydroxyalkyl of 1 to 6 carbon atoms are described.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates, to prepare polyureas/polyurethanes; with acids or derivatives, to prepare polyesters or polycarbonates are disclosed.
    Type: Grant
    Filed: June 20, 1988
    Date of Patent: February 6, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas
  • Patent number: 4869748
    Abstract: Herbicidal compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)- wherein R.sup.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: September 26, 1989
    Assignee: ICI Americas Inc.
    Inventor: Christopher G. Knudsen
  • Patent number: 4853028
    Abstract: Compounds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano, nitro, (S(O).sub.n R wherein R is C.sub.1 -C.sub.4 alkyl and n is the integer 0, 1 or 2; and R.sup.2 through R.sup.8 are hydrogen or certain substituents, their salts, herbicidal compositions containing the compound or salts and the herbicidal use thereof.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: August 1, 1989
    Assignee: Stauffer Chemical Company
    Inventors: Charles G. Carter, David L. Lee, William J. Michaely
  • Patent number: 4849138
    Abstract: A method of producing alkali metal benzenesulfinates having the general formula of ##STR1## wherein M represents Na or K, which comprises: reacting nitrophenylphenyl sulfones having the general formula of ##STR2## wherein n is an integer of 1 or 2, with alkali metal thiophenolates having the general formula of ##STR3## in solvents. The reaction produces also nitrophenylphenyl sulfides as by-products in equimolar amounts to the alkali metal benzenesulfinates, and the oxidation of the sulfides provides the starting nitrophenylphenyl sulfones.A method of producing the nitrophenylphenyl sulfones is also provided wherein the sulfides are oxidized with hydrogen peroxide in the presence both of water-soluble tungstates or molybdates and of phase transfer catalysts in a two-phase heterogeneous solvent.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: July 18, 1989
    Assignee: Seitetsu Kagaku Co., Ltd.
    Inventors: Akira Onoe, Masao Kawamura, Kunioki Kato, Masato Yoshikawa, Hirokazu Kagano
  • Patent number: 4845119
    Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent of each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substitutent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkyl;wherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --; andwherein R.sup.9 is alkyl or up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.
    Type: Grant
    Filed: February 18, 1986
    Date of Patent: July 4, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Leslie R. Hughes, Howard Tucker
  • Patent number: 4845129
    Abstract: The invention discloses certain diaryl substituted cyclopentane and cyclopentene derivatives useful as PAF inhibitors, pharmaceutical compositions containing said compounds as an active ingredient thereof and a method of using such compositions for inhibiting PAF-induced blood platelet aggregation, PAF-mediated broncho-constriction and extravasation, PAF-induced hypotension, PAF-induced ischemic bowel disease and PAF-mediated, endotoxin induced lug injury.
    Type: Grant
    Filed: March 14, 1988
    Date of Patent: July 4, 1989
    Assignee: Sandoz Pharm. Corp.
    Inventors: Robert C. Anderson, William J. Houlihan, Howard C. Smith, Edwin B. Villhauer
  • Patent number: 4837352
    Abstract: An intermediate compound having the structural formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub. 1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: June 6, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4814507
    Abstract: A novel sulfone compound represented by the general formula (I) ##STR1## wherein R.sup.1 is cyclohexyl, phenyl; or a phenyl substituted with a group selected from nitro, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are respectively hydrogen, halogen, cyano or carbonyl, wherein R.sup.1 and R.sup.2 may form an o-phenylene or an o-phenylene substituted with at least one group selected from nitro C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen; X is oxygen or methylkene; Y is -(CH.sub.2).sub.n --, wherein n is an integer of 0, 5 or 6, or ##STR2## wherein m is an integer 1-3; R.sup.6 is hydrogen, C.sub.1 -C.sub.3 alkyl, .omega.-alkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms, or .omega.-dialkylaminoalkyl, wherein each alkyl has 1-3 carbon atoms; R.sup.7 is hydrogen or C.sub.1 -C.sub.3 alkyl; and R.sup.6 and R.sup.7 may form a ring together with N, or ##STR3## wherein R.sup.8 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: September 14, 1987
    Date of Patent: March 21, 1989
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Akihiro Tobe, Shinichiro Fujimori, Tomoshi Yamazaki, Mamoru Sugano, Ryoji Kikumoto, Issei Nitta
  • Patent number: 4783213
    Abstract: Compounds of the formula ##STR1## wherein X is oxy, thio, sulfinyl or sulfonyl;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, or phenyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.
    Type: Grant
    Filed: August 20, 1987
    Date of Patent: November 8, 1988
    Assignee: Stauffer Chemical Company
    Inventor: David L. Lee
  • Patent number: 4781751
    Abstract: Compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, halogen, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is halogen, cyano, nitro, trifluoromethyl, --C(O)--OR.sup.f wherein R.sup.f is C.sub.1 -C.sub.4 alkyl, or --C(O)NR.sub.2.sup.b wherein R.sup.b is hydrogen or C.sub.1 -C.sub.2 alkyl;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 2, 1987
    Date of Patent: November 1, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Hsiao-Ling M. Chin
  • Patent number: 4778932
    Abstract: In preparing a diarylsulfone by condensing sulfuric acid or an aromatic sulfonic acid with an aromatic compound having at least one replaceable hydrogen atom on the aromatic ring, the process of the present invention is characterized in that the condensation reaction is carried out in the presence of at least one catalyst selected from the group consisting of a tungstic acid, molybdic acid and heteropoly acid thereof.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: October 18, 1988
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Hiroshi Manami, Shigeo Miki, Mikio Nakazawa
  • Patent number: 4762551
    Abstract: A compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 can be oxo; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms; and R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: August 9, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4744812
    Abstract: Substituted diphenyl ethers of the formula ##STR1## where Z.sub.1, Z.sub.2 and Z.sub.3 are hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, Z.sub.4 is hydrogen, cyano, alkyl, alkoxy, acetoxy or alkylmercapto, Y is hydrogen, halogen, cyano or nitro, X is oxygen, sulfur, sulfinyl or sulfonyl, and A is hydrogen, unsubstituted or substituted alkyl ##STR2## and can also be sulfonyl ##STR3## when X is oxygen, and, when Z.sub.4 is alkoxy or alkylmercapto, can also be a methylene chain --(CH.sub.2).sub.m -- by which the radicals Z.sub.4 --CH--X-- are bonded to form a ring, R.sub.1 is hydrogen, methyl, ethyl or n-propyl, R.sub.2 is cyano, methoxy, ethoxy or ##STR4## where B is OH, ONa, O--alkyl, unsubstituted or substituted phenoxy, --NH.sub.2, --NH--alkyl or --N(alkyl).sub.2, n is 1, 2 or 3, R.sub.3 and R.sub.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
  • Patent number: 4724263
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen; halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; or R.sup.a SO.sub.m --wherein m is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are methyl or ethyl;R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)--wherein R.sup.e is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.sup.c)C(O)R.sup.d wherein R.sup.c and R.sup.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: February 9, 1988
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Carter
  • Patent number: 4724268
    Abstract: A crude 3,3'-dinitrodiphenyl compound selected from 3,3'-dinitrodiphenylsulfone or 3,3'-dinitrobenzophenone is purified by reacting the crude 3,3'-dinitrodiphenyl compound with a lower alcohol in the presence of a base so as to convert practically the isomer or isomers, which contain one or more nitro groups at the ortho- or/and para-positions, only into the corresponding alkoxy compound or compounds thereof and then separating the alkoxy compound or compounds.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: February 9, 1988
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Teruyuki Nagata, Akihiro Yamaguchi
  • Patent number: 4724267
    Abstract: Bis(haloacylaromatic) compounds have been made by a new process in which monohaloacylated aromatic compounds have been reacted by a coupling reaction. These bis(haloacylaromatic) compounds can be employed as monomers in the preparation of polyesters and polyamides which have easy processability. The monohaloacylated compound is coupled by reacting two moles of the monomer with a carbon or sulfur compound containing at least two halogen atoms in the presence of a Friedel-Crafts catalyst.
    Type: Grant
    Filed: May 23, 1986
    Date of Patent: February 9, 1988
    Assignee: The Dow Chemical Company
    Inventors: George M. St. George, Marlin E. Walters
  • Patent number: 4719029
    Abstract: The ammonium salt of a sulfated ethoxylated alcohol is used as an emulsifying agent to provide resistance to biological degradation of continuous water phase hydraulic fluids. The emulsification agent allows the necessary emulsification properties and in addition provides bioresistance such that there is no need to add a secondary biocide nor to correct emulsification characteristics in order to hold such materials stable in emulsion.
    Type: Grant
    Filed: January 15, 1987
    Date of Patent: January 12, 1988
    Assignee: Conoco Inc.
    Inventor: Bryant J. Hardy
  • Patent number: 4719236
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid additon salts thereof; wherein Ar is a perylene or substituted perylene ring system; R.sup.1 contains not more than eight carbon carbon atoms and is a group ##STR1## wherein m is 0 or 1;R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl; R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: January 12, 1988
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4681621
    Abstract: Compounds of the formula ##STR1## wherein R is halogen, preferably chlorine or bromine; C.sub.1 -C.sub.4 alkoxy, preferably methoxy; nitro; cyano; --S(O).sub.n R' wherein n is the integer 0, 1 or 2, preferably 2 and R' is C.sub.1 -C.sub.4 alkyl, preferably methyl; or R is C.sub.1 -C.sub.4 alkyl or methyl and most preferably R is chlorine, bromine, methoxy, nitro, methyl or CF.sub.3 ; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or ##STR2## wherein R.sup.a is C.sub.1 -C.sub.4 alkyl; R.sup.1 and R.sup.2 together are alkylene having 3 to 6 carbon atoms; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; and R.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) OCF.sub.3 ; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1, or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: July 21, 1987
    Assignee: Stauffer Chemical Company
    Inventors: David L. Lee, William J. Michaely
  • Patent number: 4621098
    Abstract: The present invention provides thioethers of the general formula: ##STR1## wherein Ar is a phenyl radical which is optionally substituted one, two or three times by alkyl, alkenyl, alkoxy, alkylthio, alkanoyl, hydroxyl, hydroxyalkyl, carboxyl, alkoxycarbonyl, carbamoyl, nitro, amino or halogen, Q is an oxygen or sulphur atom or an NH group, A is a straight-chained or branched C.sub.2 -C.sub.8 alkylene radical which is optionally substituted by a hydroxyl group or can be interrupted by an ethenylene or ethynylene group, n is 0, 1 or 2, and R is a hydrogen atom or a straight-chained or branched alkyl radical which is optionally substituted one or more times by the same or different radicals selected from alkoxycarbonyl, alkoxy, hydroxyl, carboxyl or optionally substituted carbamoyl or amino; as well as the pharmacologically acceptable salts thereof, with the proviso that A cannot be ethylene when Ar is a phenyl radical, Q is an oxygen atom and R is the group --CH.sub.2 COOH.
    Type: Grant
    Filed: July 2, 1984
    Date of Patent: November 4, 1986
    Assignee: Boehringer Mannheim GmbH
    Inventors: Robert Umminger, Walter-Gunar Friebe, Wolfgang Kampe, Androniki Roesch, Otto-Henning Wilhelms
  • Patent number: 4612394
    Abstract: A process for producing aminophenyl-.beta.-hydroxyethylsulfone of the formula (I), ##STR1## which comprises the following steps: (1) condensing nitrohalobenzene with mercaptoethanol in the presence of an alkali hydroxide and at least one reaction medium selected from N-alkyl-substituted amides and sulfoxides to produce mononitrophenyl-.beta.-hydroxyethylsulfide of the formula (II): ##STR2## (2) oxidizing the mononitrophenyl-.beta.-hydroxyethylsulfide (II) to produce mononitrophenyl-.beta.-hydroxyethylsulfone of the formula (III): ##STR3## and (3) reducing the mononitrophenyl-.beta.-hydroxyethylsulfone to produce the aminophenyl-.beta.-hydroxyethylsulfone of the formula (I). This compound is useful as an intermediate for aminophenyl-.beta.-sulfatoethylsulfone represented by the following formula: ##STR4## which is an important intermediate for vinyl sulfone type reactive dyes largely used for dyeing cellulose fiber materials.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: September 16, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Norio Kotera, Kazuhiro Tada, Shinzaburo Masaki, Kunihisa Goto, Tatsuo Kaneoya
  • Patent number: 4588433
    Abstract: Phenoxymethane derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, halogen, alkoxycarbonyl, cycloalkoxycarbonyl or nitro,R.sup.2 represents hydrogen, alkyl or halogen,R.sup.3 represents hydrogen, alkyl, alkenyl, alkinyl, phenyl which is optionally substituted by alkyl and/or halogen, phenylalkyl which is optionally substituted by alkyl and/or halogen, alkoxy, phenoxy, halogenoalkyl, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphonyl, phenylthio, phenylsulphonyl, nitro or halogen,R.sup.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: May 13, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Georg Schmitt, Klaus Lurssen, Karlfried Wedemeyer
  • Patent number: 4567004
    Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.
    Type: Grant
    Filed: July 18, 1984
    Date of Patent: January 28, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters
  • Patent number: 4554381
    Abstract: A process for sulfonylation of halobenzenes, in which a halobenzene is reacted with a sulfonic acid, a precursor or a derivative thereof in the presence of boron trifluoride in an amount such that the absolute pressure of boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: November 19, 1985
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4552984
    Abstract: A process for the preparation of .alpha.,.alpha.-difluoroalkoxy or .alpha.,.alpha.-difluoroalkylthiophenyl sulfones, in which a polyhaloalkoxybenzene or a polyhaloalkylthiobenzene is reacted with a sulfonic acid, a derivative or a precursor of this acid, in the presence of boron trifluoride in an amount such that the absolute pressure of the boron trifluoride within the reaction vessel exceeds 1 bar, and in the presence of hydrofluoric acid as a solvent. The resultant products are useful as intermediates in the synthesis of compounds having a phytosanitary (e.g., herbicidal) or pharmaceutical activity.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: November 12, 1985
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4548640
    Abstract: Novel allylthiodiphenyl ether compounds exhibit excellent herbicidal activity against broadleaf weeds while leaving crops such as corn, wheat, rice and soybeans unaffected. Preparation and herbicidal activity of the compounds is disclosed and exemplified.
    Type: Grant
    Filed: October 21, 1983
    Date of Patent: October 22, 1985
    Assignee: FMC Corporation
    Inventor: Elsayed A. Aly
  • Patent number: 4503276
    Abstract: This invention pertains to a process for separating nitration isomers of 1,3-disubstituted and 1,2,4-trisubstituted benzene compounds. The separated isomers have a variety of uses including precursors for 2-haloacetanilide herbicides.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: March 5, 1985
    Assignee: Monsanto Company
    Inventor: Thomas E. Nickson
  • Patent number: 4459152
    Abstract: The invention describes gametocidal and microbicidal compositions which contain, as active ingredient, a nitroarylalkylsulfone derivative of the formula I ##STR1## wherein R.sub.1 is alkyl, R.sub.2 and R.sub.3 are each hydrogen, alkyl, alkoxy, haloalkyl, halogen, cyano, nitro or amino or together they complete a naphthalene ring; R.sub.4 is hydrogen or --COR.sub.5, wherein R.sub.5 is alkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, cycloalkyl, phenyl, benzyl, furyl or tetrahydrofuryl. The invention relates also to the use of these compositions and compounds for stimulating generative plant growth and for obtaining hybrid seeds, as well as to a method of preparing the hydrazinium and ammonium salts within the scope of the formula I, and to a process for preparing agrochemical compositions which contain compounds of the formula I as active ingredient.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: July 10, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Ernst Fankhauser, Elmar Sturm
  • Patent number: 4440964
    Abstract: The disclosure herein relates to substituted 2-alkylsulfonylalkyl nitrobenzenes and a process for the preparation thereof. The compounds herein are useful as intermediates in the preparation of certain substituted anilines used as reactants in the preparation of 2-haloacetanilide herbicides.
    Type: Grant
    Filed: March 17, 1982
    Date of Patent: April 3, 1984
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Gerhard H. Alt, Terry M. Balthazor
  • Patent number: 4393079
    Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.
    Type: Grant
    Filed: December 15, 1976
    Date of Patent: July 12, 1983
    Assignee: Beecham Group Limited
    Inventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
  • Patent number: 4358308
    Abstract: The 4-perfluoroacetyl-, 4-perfluoromethylthio-, 4-perfluoromethylsulfinyl-, and 4-perfluoromethylsulfonyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: November 9, 1982
    Assignee: Rohm and Haas Company
    Inventor: Colin Swithenbank
  • Patent number: 4335055
    Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.
    Type: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4283348
    Abstract: 2-Aryl-1,3-cyclopentanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal and acaricidal activity.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: August 11, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4271072
    Abstract: Water-soluble dyestuffs are disclosed which, in the form of the free acid, have the formula ##STR1## wherein R.sub.1 is selected from the group consisting of H, alkyl having 1-4carbon atoms, cyanoalkyl having 2-4 carbon atoms, hydroxy alkyl having 2-4 carbon atoms or a sulfuric acid ester of a hydroxy alkyl having 2-4 carbon atoms; R.sub.2 is selected from the group consisting of H, methyl, ethyl, methoxy or ethoxy; R.sub.3 is selected from the group consisting of H, halogen, methyl, ethyl, methoxy, ethoxy, or carbonamido having 1-4 carbon atoms;R.sub.4 is selected from the group consisting of H, methyl, ethyl, methoxy or ethoxy; andR.sub.5 is selected from the group consisting of H, methyl, ethyl, methoxy or ethoxy. These dyestuffs are suitable for dyeing and printing cellulose fiber materials and polyamide fibers according to known methods of applying and fixing fiber-reactive dyestuffs and are distinguished by outstanding fastness properties such as fastness to light, wet processing and acid.
    Type: Grant
    Filed: August 13, 1979
    Date of Patent: June 2, 1981
    Assignee: American Hoechst Corporation
    Inventors: Johann Wenghoefer, Dennis Messier, James Thompson
  • Patent number: 4256657
    Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: March 17, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4256659
    Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: March 17, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4256658
    Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.
    Type: Grant
    Filed: January 22, 1980
    Date of Patent: March 17, 1981
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4209532
    Abstract: 2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: June 24, 1980
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler