Ketone Containing Patents (Class 568/42)
  • Patent number: 5189165
    Abstract: A process for preparing a compound I ##STR1## with A=t-butyl, aryl andR=alkyl, alkenyl, alkynyl, alkenynyl, cycloalkyl(alkyl), aryl, arylalkyl, alkyl-S-(-O)-arylby reacting a compound III ##STR2## with a compound IV ##STR3## under the conditions of a phase-transfer reaction, is described. The process gives excellent yields and is not associated with the unpleasant odor of mercaptans.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Burdinski, Reinhard Kirsch, Hariolf Kottmann
  • Patent number: 5169988
    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- to 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 halogen, 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: April 8, 1992
    Date of Patent: December 8, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5152826
    Abstract: An herbicide 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; orR.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; orR.sup.3 and R.sup.4 together are 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; orR.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.4 alkyl; (b) C.sub.1 -C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: October 6, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: Christopher G. Knudsen
  • Patent number: 5132462
    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- to 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 halogen, 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: March 7, 1991
    Date of Patent: July 21, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Tobler
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5132423
    Abstract: Reactions between a solid polar and a non-polar compound, especially nucleophilic aromatic substitution reactions between an alkali metal salt of a hydroxyaromatic compound or thio analog thereof and an activated halo- or nitro-substituted aromatic compound, are conducted in a non-polar organic solvent such as toluene or xylene, in the presence of a hexaalkylguanidinium or .alpha.,.omega.-bis(pentaalkylguanidinium)alkane salt, or a corresponding heterocyclic salt, as a phase transfer catalyst. The method is particularly useful for the preparation of bisimides from bisphenol A or 4,4'-biphenol salts and 4-nitro- or 4-halophthalimides.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: July 21, 1992
    Assignee: General Electric Company
    Inventors: Daniel J. Brunelle, Deborah A. Haitko, James P. Barren, Sunita Singh
  • Patent number: 5128479
    Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: January 29, 1990
    Date of Patent: July 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5116869
    Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: May 26, 1992
    Assignee: Teijin Limited
    Inventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
  • Patent number: 5113019
    Abstract: The invention relates to the preparation of alkylthiophenols by reaction of a dialkyl disulphide with a phenol.In the process according to the invention, the reaction is carried out in the presence of aluminum chloride or of ferric chloride in a solvent of the alkylbenzene type or, soley in the case of methylthiolation, in an excess of dimethyl disulphide.This process makes it possible, in particular to obtain, with a selectivity and in a yield which are excellent, 2-alkylthiophenols which may then be converted into 4-acyl-2-alkylthiophenols by means of a reaction at a temperature ranging from 40.degree. to 100.degree. C. with a complex BF.sub.3 :2RCOOH where R denotes an alkyl or propenyl radical, in a proportion of 10 to 15 moles of complex per mole of 2-alkylthiophenol.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: May 12, 1992
    Assignee: Societe Nationale Elf Aquitaine (Production)
    Inventors: Catherine Vottero, Yves Labat, Jean-Marie Poirier
  • Patent number: 5110343
    Abstract: The invention relates to a herbicidal composition having an inert carrier and an effective amount of a compound having the formula ##STR1## wherein X is the same or different substituent selected from the group consisting of halogen, nitro, C.sub.1-6 alkyl, halo C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.1-6 alkylsulfonyl;n is 1, 2, 3 or 4;R.sup.1 is C.sub.1-6 alkyl which is substituted by cyano, halogen, hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl or tetrahydropyranyloxy; C.sub.1-6 alkylthio, phenylthio, pyridyl or tetrahydropyranyl;R.sup.2 is C.sub.1-6 alkyl;l is 0, 1 or 2.
    Type: Grant
    Filed: May 24, 1990
    Date of Patent: May 5, 1992
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Akiyoshi Ueda, Haruhito Ohishi, Toshio Aihara, Hisao Ishikawa, Kazuyuki Tomida, Hideo Hosaka
  • Patent number: 5108489
    Abstract: Herbicidal disubstituted naphthalenes of the formula ##STR1## in which A represents optionally branched alkanediyl,R represents hydrogen or in each case optionally substituted alkyl or phenyl,R.sup.1 represents hydrogen, halogen, cyano or trifluoromethyl,R.sup.2 represents hydrogen or halogen,R.sup.3 represents halogen, trifluoromethyl, trifluoromethoxy, trifluoromethylthio or trifluoromethylsulphonyl,R.sup.4 represents hydrogen or halogen,X represents nitrogen or the group C--R.sup.5, whereR.sup.5 represents hydrogen or halogen,Y represents oxygen or sulphur, andZ represents oxygen, the group N--(O).sub.n --R.sup.
    Type: Grant
    Filed: July 24, 1991
    Date of Patent: April 28, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Roland Andree, Michael Haug, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
  • Patent number: 5107029
    Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and an organic anhydride compound such as methanesulfonic anhydride or trifluoroacetic anhydride. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: April 21, 1992
    Assignee: Eastman Kodak Company
    Inventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
  • Patent number: 5101053
    Abstract: Radiation sensitive sulfonium salts which contain (1) a sulfonium initiator portion, (2) a spacer portion, and (3) a reactive group portion. The spacer portion has the formula "-o-w- x-z-" wherein "w" is a single bond or one of --C(O)--, --C(O)O--, --C(O)S--, --C(O)NH-- --C(O)N(alkyl)--, --C(S)--, --C(S)S--,--S(O)--, --S(O)(O)--, or --S(O)(O)O--; "X" is an unsubstituted or substituted alkylene radical; and "Z" is --O--, --NH--, --N(C,--C.sub.6 -alkyl)--, or --N(phenyl)--. The reactive group portion is --CH.dbd.CH.sub.2 or --C(O)--C(Y).dbd.CH.sub.2 wherein "Y" is H, C.sub.1 -.sub.6 -alkyl, or phenyl. The sulfonium salts find use in curing monomers which can be subjected to cationic polymerization.
    Type: Grant
    Filed: January 9, 1990
    Date of Patent: March 31, 1992
    Assignee: BASF Aktiengesellschaft
    Inventor: Andreas Boettcher
  • Patent number: 5100460
    Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5101076
    Abstract: Compounds of the present invention are represented by the formula, ##STR1## wherein X represents a lower alkyl, lower alkoxy, lower haloalkyl or lower haloalkoxy group or a halogen atom, and R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group. They are useful intermediates for preparing herbicidal compounds.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: March 31, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Masao Shiroshita, Susumu Ohtsuka, Kenji Arai, Naonori Hirata
  • Patent number: 5099071
    Abstract: A charge generating compound for use in electrophotographic devices of the formula: ##STR1## wherein: A and A.sup.1 are each independently selected from phenyl, substituted phenyl, quinolino, naphthyl and substituted naphthyl wherein the substituents are independently selected from halo, alkyl, alkoxy, alkylthio, phenyl, phenoxy, phenylthio, CF.sub.3, CH.sub.2 OH, CO.sub.2 R.sup.1, NHCOR.sup.1, COR.sup.1, NO.sub.2 and NR.sup.1 R.sup.2 ;R.sup.1 and R.sup.2 are each independently H or C.sub.1-6 -alkyl.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: March 24, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Pralad Mistry, Prakash Patel
  • Patent number: 5075339
    Abstract: The invention relates to benzylketone phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylketone phospholipase A.sub.2 inhibitor. These compounds are also intermediates in the synthesis of other PLA.sub.2 inhibitors.
    Type: Grant
    Filed: June 1, 1990
    Date of Patent: December 24, 1991
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventor: Wendell W. Wilkerson
  • Patent number: 5047420
    Abstract: Novel 1,3-diaryl cyclopentanes of the following general formula were prepared. ##STR1## These compounds were found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities and as such useful in the treatment or amelioration of various diseases or disorders mediate by the PAF, for example, hypotension, inflammation, nephritis, stroke and other cardiovascular disorders, asthma, allergic and skin diseases, peptic or stomach ulcer, shock, lung edema, psoriasis, adult respiratory distress syndrome, pain including dental pain, and aggregation of platelets.
    Type: Grant
    Filed: August 21, 1989
    Date of Patent: September 10, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Donald W. Graham, Tesfaye Biftu, John C. Chabala, Michael N. Chang, Yuan-Ching P. Chiang, Kathryn L. Thompson, Shu S. Yang
  • Patent number: 5047593
    Abstract: This invention encompasses a compound of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are the same or different members of the group consisting of 1,1-dimethylethyl, halo, phenyl and substituted phenyl; Alk is straight or branched chain lower alkylene; R.sub.4 is hydrogen or lower alkyl; R.sub.3 is hydrogen or lower alkyl; or a cycloalkyl group of from 3 to 8 carbon atoms. The formulation of this invention are useful as anti-inflammatory and anti-allergy agents.
    Type: Grant
    Filed: June 2, 1989
    Date of Patent: September 10, 1991
    Assignee: G. D. Searle & Co.
    Inventor: Richard A. Mueller
  • Patent number: 5041681
    Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.2 X' in the presence of a base, wherein X' is a leaving group.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: August 20, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventor: Glynn Mitchell
  • Patent number: 5041679
    Abstract: Compounds of the present invention are represented by the formula, ##STR1## wherein X represents a lower alkyl, lower alkoxy, lower haloalkyl or lower haloalkoxy group or a halogen atom, and R.sup.1 and R.sup.2, which may be the same or different, represent a hydrogen atom or a methyl group. They are useful intermediates for preparing herbicidal compounds.
    Type: Grant
    Filed: December 30, 1988
    Date of Patent: August 20, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Mitsunori Hiratsuka, Masao Shiroshita, Susumu Ohtsuka, Kenji Arai, Naonori Hirata
  • Patent number: 5041613
    Abstract: Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: August 20, 1991
    Assignee: Eastman Kodak Company
    Inventor: Charles A. McCombs
  • Patent number: 5023382
    Abstract: 2,3-disubstituted-2-cyclopenenones (such as cisjasmone) are prepared by (a) reacting an alkl 2-chloro-2,3-disubstituted-3-butenoate with a lithiomercaptan compound, (b) subjecting that product to reductive dehydrosulfurization. Methods of preparing the reactants are also disclosed.
    Type: Grant
    Filed: January 24, 1990
    Date of Patent: June 11, 1991
    Assignee: Petrolite Corporation
    Inventor: Jacob Mathew
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 5015777
    Abstract: A process for the preparation of aromatic beta-diketones by the reaction of an acetophenone and a molar excess of an alphatic ester or an ester of benzoic acid in the presence of sodium alkoxide condensation agent in an aromatic hydrocarbon solvent. Also disclosed is a method of recycling the solvent and excess ester reactant after separation of the aromatic beta-diketone product.
    Type: Grant
    Filed: November 2, 1989
    Date of Patent: May 14, 1991
    Assignee: Witco Corporation
    Inventors: Daniel R. Chisolm, Richard A. Weiss, Leonid Rozov
  • Patent number: 5012007
    Abstract: A method is provided for the production of 2,2-diorgano-1-indanones, e.g., 2,2-dimethyl-1-indanone, by reacting an alcohol which is the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)carbinol, e.g., 2-methyl-1-phenyl-1-propanol, with carbon monoxide in the presence of a Lewis acid catalyst, e.g., hydrogen fluoride, with any substituents on the phenyl group of the alcohol being hydroxy or organo. The foregoing reaction is preferably integrated with the preparation of the feed alcohol by reducing the corresponding (diorganosubstitutedmethyl)phenyl(or substitutedphenyl)ketone, e.g., isobutyrophenone, with a reducing agent containing available hydrogen, e.g., sodium borohydride, or with hydrogen gas in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: April 30, 1991
    Inventor: Varadaraj Elango
  • Patent number: 4994623
    Abstract: Thiophenones are produced by acylating the aromatic ring of thiophenolic ethers in the presence of anhydrous hydrofluoric acid. It has been found that if the thio group is in the form of a thioether and not a thiol, the aromatic ring can be acylated to form the thiophenone in the presence of anhydrous hydrofluoric acid.
    Type: Grant
    Filed: March 27, 1990
    Date of Patent: February 19, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Kenneth G. Davenport, Wilson B. Ray, Mohammad Aslam
  • Patent number: 4992504
    Abstract: Composition containing a chlorine-containing polymer and at least one compound of the formula IA ##STR1## in which R.sup.1 and R.sup.3 independently of one another are C.sub.1 -C.sub.12 alkyl, phenyl, phenyl which is substituted by one to three C.sub.1 -C.sub.12 alkyl groups, C.sub.7 -C.sub.10 phenylalkyl or C.sub.7 -C.sub.10 phenylalkyl which is substituted on the phenyl ring by one to three C.sub.1 -C.sub.12 alkyl groups and R.sup.1 is additionally --R.sup.2 --X--R.sup.3, R.sup.2' is C.sub.1 -C.sub.10 alkylene, R.sup.4 is hydrogen, C.sub.2 -C.sub.5 alkoxycarbonyl or C.sub.2 -C.sub.5 alkanoyl and X is oxygen or sulfur.Compounds of the formula IA in which R.sup.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: February 12, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann O. Wirth, Hans-Helmut Friedrich
  • Patent number: 4982005
    Abstract: Benzophenones are prepared by condensing benzoic acids and aromatics of the benzene series by means of boron trifluoride in nitrobenzene as reaction medium.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: January 1, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4982006
    Abstract: The present invention involves process for the preparation of compounds having the chemical structure: ##STR1## wherein Ar--H is an aromatic compound which is activated to an electrophilic attack, and wherein --Y is an aliphatic group having a labile moiety, especially where the labile moiety is a terminally unsaturated moiety: --C.tbd.CH, ##STR2## or aldehydes in the form of their acetals. The process comprises the step of reacting Ar--H and ##STR3## wherein --X is --Cl or --Br, and where the reaction step is carried out in a solvent medium at a temperature of from about -40.degree. C. to about -100.degree. C. using stannic chloride as a catalyst.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 1, 1991
    Assignee: Norwich Eaton Pharmaceuticals, Inc.
    Inventor: Thomas T. Hudec
  • Patent number: 4980485
    Abstract: Optically active periplanone-B is manufactured through oxidizing (1RS, 4S, 5E)-isopropyl-7-methylene-5-cyclodecene-1-ol. The oxidized product is regioselectively enolized and then sulfenylated. The sulfenylated product is oxidized and then subjected to decomposition of the sulfoxide. The decomposed product is epoxidated, and the epoxidated product is converted into an enolate which is then oxidized. The oxidized product is oxidized and then regio- and stereoselectively epoxidated to obtain optically active periplanone-B.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: December 25, 1990
    Assignee: Japan Tobacco Inc.
    Inventors: Kenji Mori, Takeshi Kitahara, Koshi Koseki
  • Patent number: 4966732
    Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at temperature temperture between -60.degree. C. and -10.degree. C.
    Type: Grant
    Filed: July 15, 1987
    Date of Patent: October 30, 1990
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4954165
    Abstract: An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2 is discosed.In addition, the herbicidally effective benzoyl derivative having the formula: ##STR2## wherein: X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2;L is C.sub.1 -C.sub.4 alkylene is disclosed.
    Type: Grant
    Filed: October 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
  • Patent number: 4929741
    Abstract: Propiolophenone derivatives of the formula ##STR1## wherein R.sup.6 is hydrogen, lower alkyl or a group of the formula ##STR2## as well as corresponding hydroxy compounds of the formula ##STR3## wherein R.sup.6' is hydrogen, lower alkyl, a group of formula (a), (b), (c), (d) or (e) or a group of the formula--C(R.sup.14)(R.sup.15)OR.sup.16' (f'):exhibit mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers and/or duodenal ulcers.
    Type: Grant
    Filed: March 17, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoffman-La Roche Inc.
    Inventors: Albert Fischli, Eva-Maria Gutknecht, Daniel Obrecht
  • 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: 4894482
    Abstract: A process is provided for removing water from a mixture of hydrogen fluoride (HF), a carboxylic acid, e.g., acetic acid, and water by extractive distillation in the presence of a Lewis base as solvent, which does not azeotrope with water, forms bonds with the HF and carboxylic acid which can be broken by heat and has a boiling point at atmospheric pressure at least about 20.degree. C. above that of the carboxylic acid, e.g., N-methyl-2-pyrrolidone, and taking off an overhead vapor comprising a major proportion of the water in said mixture. The extractive distillation may be advantageously integrated in an overall process with the production of an aromatic ketone, e.g., 4-hydroxyacetophone, by the Friedel-Crafts acylation of an aromatic compound, e.g., phenol, with the carboxylic acid, using HF as catalyst, to produce a product mixture comprising the aromatic ketone, HF, carboxylic acid and water, and the removal of aromatic ketone from the product mixture by means of a solvent assisted distillation.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: January 16, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Daniel D. Lindley, Carl D. Murphy
  • 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: 4827004
    Abstract: Novel Isoprene Derivatives which have mucosa-protective and gastric acid secretion-inhibiting properties and are useful for combatting ulcers both by treating and as a prophylaxis against gastric and/or duodenal ulcers.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: May 2, 1989
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Albert Fischli, Max Schmid, Rudolf Schmid
  • Patent number: 4822905
    Abstract: Compounds having the structural formula ##STR1## wherein R.sub.1, R.sub.2 R.sub.3, R.sub.4 and R.sup.5 are the same or different and are selected from the group consisting of hydrogen, chlorine, bromine, iodine, nitro, alkyl having from 1 to 4 carbon atoms, alkoxy having from 1 to 4 carbon atoms, trifluoromethyl, trifluoromethoxy, cyano, alkylsulfonyl, and alkylthio having from 1 to 4 carbon atoms, and wherein R.sub.2 and R.sub.3 or R.sub.3 and R.sub.4 together can be methylene or ethylenedioxy.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: April 18, 1989
    Assignee: Stauffer Chemical Company
    Inventors: David L. Lee, Donald R. James, William J. Michaely
  • Patent number: 4814340
    Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: March 21, 1989
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
  • Patent number: 4792634
    Abstract: A method for preparing aryl sulfides by heating an iodoaromatic compound with elemental sulfur at a temperature above about 150.degree. C.
    Type: Grant
    Filed: August 20, 1987
    Date of Patent: December 20, 1988
    Assignee: Eastman Kodak Company
    Inventor: Mark Rule
  • Patent number: 4788341
    Abstract: 2-Acetonaphthones are prepared by heating a compound selected from the group consisting of ketals and enol ethers of acetyl-substituted benzalacetone at a temperature effective to cyclize the compound and form said 2-acetonaphthones.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: November 29, 1988
    Assignee: Eastman Kodak Company
    Inventor: Joseph R. Zoeller
  • 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: 4780569
    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.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;R.sup.2, R.sup.3, R.sup.4, 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.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 25, 1988
    Assignee: Stauffer Chemical Company
    Inventor: David L. Lee
  • 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: 4751240
    Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R.sup.1 is hydrogen, or alkyl, alkenyl, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 --or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --(PO)R.sup.2 13 , --S--, --SO--or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: June 14, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
  • Patent number: 4731484
    Abstract: New compounds which are 4,4'-bis(trihaloacetyl) derivatives of aromatic compounds have been prepared by reacting an aromatic compound with a haloacetyl halide in the presence of a Friedel-Crafts catalyst, e.g. AlCl.sub.3, in a suitable solvent. The compounds are useful in preparing polycarbonates, polyesters, polyamides, polyketones and polyurethanes.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: March 15, 1988
    Assignee: The Dow Chemical Company
    Inventor: Marlin E. Walters
  • 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