Patents Represented by Attorney Karl F. Jorda
  • Patent number: 4595755
    Abstract: There is described a novel process for producing 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one (4-lilolidone), usable as fungicide and corresponding to the formula ##STR1## as well as novel 5-halo-1,2,3-(1,2-dihydropyrrolo)-4-quinolones of the formula ##STR2## in which "Hal" is chlorine or bromine, which are formed as intermediates during the process.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: June 17, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4590292
    Abstract: A modified novel process for preparing cyclopropylamine from .gamma.-butyrolactone is described. The .gamma.-butyrolactone ring is cleaved with a hydrohalide in the presence of a novel catalyst comprising an aqueous sulfuric acid solution. The 4-chlorobutyric acid, thus formed is converted into a hindered chlorobutyrate ester. The hindered ester based on secondary and tertiary alkanols of eight or less carbon atoms, is cyclized to form the hindered cyclopropanecarboxylate ester by a novel reaction medium consisting of solid caustic in a water-immiscible solvent and a phase transfer catalyst. The hindered cyclopropanecarboxylate ester is ammoniated to form cyclopropanecarboxamide by a novel catalyst comprising an alkali metal salt of a polyol having hydroxy groups on adjacent carbons. The carboxamide formed in substantially quantitative yields is converted to cyclopropylamine by a modified Hofmann reaction utilizing continuous degradation of the intermediate with simultaneous distillation.
    Type: Grant
    Filed: June 10, 1985
    Date of Patent: May 20, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph T. Blackwell, Harold L. Daughety, Henry C. Grace, Ward H. Oliver
  • Patent number: 4587353
    Abstract: There is described a process for producing N-chlorosulfenyl compounds of the formula ##STR1## in which R.sub.1 is alkyl, alkoxycarbonyl, alkoxycarbonylalkyl or 2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl, and R.sub.2 is alkyl or alkoxycarbonylalkyl, which process is based on the reaction of an amino compound of the formula ##STR2## with sulfur dichloride. The essential feature of the process is that the reaction of the amino compound of the above formula with the sulfur dichloride is performed in excess sulfur dichloride as solvent and in the absence of a base. The formed N-chlorosulfenyl compounds of the above formula are intermediates for insecticidal and acaricidal active substances.
    Type: Grant
    Filed: August 23, 1983
    Date of Patent: May 6, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Hansjakob Fah
  • Patent number: 4560771
    Abstract: 1,2-Benzoxathiine derivatives of the formula I ##STR1## wherein Hal is chlorine, bromine or iodine,R is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, cyano or a --X--R.sup.1, --CO--X--R.sup.2, --CO--NR.sup.3 R.sup.4, --SO--R.sup.5 or --SO.sub.2 --R.sup.6 group, whereR.sup.1 is C.sub.3 -C.sub.5 alkynyl, or is C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 alkoxy, or is C.sub.3 -C.sub.5 alkenyl, unsubstituted or substituted by halogen or C.sub.1 -C.sub.4 alkoxy,R.sup.2 and R.sup.5 are each independently of the other C.sub.1 -C.sub.4 alkyl,-C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, phenyl or benzyl,R.sup.3 and R.sup.4 are each independently of the other hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl, phenyl or benzyl, R.sup.6 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: December 24, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Werner Fory
  • Patent number: 4558145
    Abstract: A new process for the preparation of HO-EDTA.FE (5% Fe) is disclosed. It is based on the oxidation of Fe.degree. by nitric acid in the presence of HO-EDTA Na.sub.3 to generate the chelate in the Fe.sup.+2 state. The Fe.sup.+2 chelate is then converted to the desired Fe.sup.+3 chelate by air oxidation.
    Type: Grant
    Filed: October 21, 1983
    Date of Patent: December 10, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Nelson Smith, Joseph W. Stutts
  • Patent number: 4556717
    Abstract: 1-[2-(2,4-Dichlorophenyl)-pentyl]-1H-1,2,4-triazole can be produced, in a novel, simple, economical and isomer-free form, by reacting 2-(2,4-dichlorophenyl)-valeronitrile, in the presence of hydrogen, an acid and a hydrogenation catalyst, with a compound H.sub.2 N--NH--R to a compound of the formula ##STR1## hydrogenating the compound (III) catalytically to a compound ##STR2## hydrolysing compounds (IV) wherein R is not hydrogen, and converting the compounds (IV) wherein R=H, or salts thereof, with formamide and/or [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride, into 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole, or converting compounds (IV) wherein R=--COR', with aqueous formic acid, into the corresponding N,N'-bisformyl derivatives, and reacting these with formamide, optionally in the presence of NH.sub.3, to 1-[2-(2,4-dichlorophenyl)-pentyl]-1H-1,2,4-triazole. R in the formulae is hydrogen, --CHO, --COR', --COOR' or --CONH.sub.2, and R' is C.sub.1 -C.sub.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: December 3, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Hansjurg Wetter, Peter Baumeister, Paul Radimerski, Pierre Martin
  • Patent number: 4550165
    Abstract: There is described a novel process for producing 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]-quinolin-4-one (4-lilolidone), usable as fungicide and corresponding to the formula ##STR1##
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: October 29, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4542216
    Abstract: A novel process for producing fluoroalkoxyaminopyrimidines of the formula I ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or benzyl, X is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, and T is hydrogen, chlorofluoromethyl, bromofluoromethyl, difluoromethyl or 1,2,2,2-tetrafluoroethyl, characterized in that a thiopyrimidine of the formula II ##STR2## wherein Y has the meaning given for X under the formula I or is hydroxyl, A is hydrogen, sodium, potassium or an equivalent of calcium or magnesium, and Q is C.sub.1 -C.sub.
    Type: Grant
    Filed: March 27, 1984
    Date of Patent: September 17, 1985
    Assignee: Ciba Geigy Corporation
    Inventor: Rudolf W. Pfluger
  • Patent number: 4534904
    Abstract: The novel process for producing N-phosphonomethylglycine comprises reacting aminomethanephosphonic acid with glyoxal, in an aqueous medium, in the presence of sulfur dioxide. The active substance obtained is a herbicide having a very wide spectrum of activity.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: August 13, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Moser
  • Patent number: 4518776
    Abstract: There is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There is also described novel sulfonylcarbamates of the above formula as intermediates.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: May 21, 1985
    Assignee: Ciba Geigy Corporation
    Inventors: Willy Meyer, Werner Fory, Werner Topfl
  • Patent number: 4502864
    Abstract: Liquid concentrate of Direct Yellow 11 based on the crown ether complexes of tetrasodium direct yellow 11, are described as well as these novel soluble chelates of insoluble tetrasodium complexes of Direct Yellow 11.
    Type: Grant
    Filed: April 25, 1984
    Date of Patent: March 5, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Jo Ann Cleverdon
  • Patent number: 4496728
    Abstract: A process is described for the production of 2-isopropyl-4-methyl-6-hydroxypyrimidine (oxypyrimidine) by reacting isopropylamidine in an alkaline lower alkanol solvent system with an alkyl acetoacetate to close the ring and form the oxypyrimidine in a continuous flow multi-stage reactor (MSR) under controlled multi-stage conditions whereby the reactants contact each other in each of said stages under conditions which reduce the possibility of the formation of unwanted reaction products from said reactants in said solvent system.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: January 29, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph T. Blackwell, III, Larry Gasper, III
  • Patent number: 4486610
    Abstract: A process is described for purifying the bacteriostat 2,4,4'-trichloro-2'-hydroxydiphenylether prepared by the diazotization of 2,4,4'-trichloro-2'-aminodiphenylether from the 2,4,8-trichlorodibenzofuran and associated nonphenolics which form. A selective solvent extraction for these non-phenolics consisting of tetrachlorethylene is used after neutralization of the hydrolyzed diazo product.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: December 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Richard B. Lund
  • Patent number: 4486358
    Abstract: The novel process for producing N-phosphonomethylglycine comprises reacting aminomethanephosphonic acid with glyoxal, in an aqueous medium, in the presence of sulfur dioxide. The active substance obtained is a herbicide having a very wide spectrum of activity.
    Type: Grant
    Filed: November 19, 1982
    Date of Patent: December 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans Moser
  • Patent number: 4479021
    Abstract: There is described a continuous process for producing 1,2-alkanediols of the formula ##STR1## in which R is an alkyl group having 3-6 carbon atoms, by reaction of a 1-alkene of the formulaR--CH.dbd.CH.sub.2in which R is as defined above, with formic acid and hydrogen peroxide, and subsequent saponification of the formed alkanediol monoformate, which process is performed in several consecutive reaction stages.The 1,2-alkanediols of the above formula obtainable by the process are intermediates for the production of pesticides.
    Type: Grant
    Filed: August 30, 1983
    Date of Patent: October 23, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Heinz Issler, Rudolf Maul
  • Patent number: 4469896
    Abstract: Chloropyridines of the formula ##STR1## wherein either R is chlorine and R' is methyl or trifluoromethyl, or R is methyl, trichloromethyl or trifluoromethyl and R' is chlorine, or R and R' are methyl, can be obtained by a novel, simple process by the addition of trichloroacetaldehyde to methacrylonitrile or .alpha.-trifluoromethacrylonitrile, 2,2-dichloropropionaldehyde, pentachloropropionaldehyde or 2,2-dichloro-3,3,3-trifluoropropionaldehyde to acrylonitrile, or 2,2-dichloropropionaldehyde to methacrylonitrile, in the presence of a catalyst, in particular copper powder or copper(I) chloride, and cyclizing the open-chain intermediate obtained.The chloropyridines of the formula (I) are known per se and are suitable for the production of different compounds, in particular of insecticides and herbicides.
    Type: Grant
    Filed: July 8, 1983
    Date of Patent: September 4, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Eginhard Steiner, Pierre Martin
  • Patent number: 4468341
    Abstract: A process for the preparation of a stable aqueous solution of the tetrasodium salt of 4,4'-bis(4-p-sulfo-anilino-6-diisopropanolamino-s-triazin-2-ylamino)-2,2'- stilbenedisulfonic acid is disclosed. The resultant solution is substantially free from destabilizing organic impurities and destabilizing inorganic salts. In the absence of these destabilizing materials the solution does not require the co-solvents of the prior art.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: August 28, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Bryan Beyer
  • Patent number: 4467117
    Abstract: An improved synthesis of the bacteriostat 2,4,4'-trichloro-2'-hydroxydiphenylether is disclosed wherein the hydrolysis after diazotization is carried out at 175.degree.-180.degree. C. to increase the yield and reaction rate. The hydrolyzed product is distilled after neutralization to remove the major portion of undesirable colored products and phenolics. The distillate is then extracted with tetrachlorethylene to separate the product from non-phenolic by-products including the 25-28% 2,4,8-trichlorodibenzofuran which are present. The final product of the process then meets F.D.A. and commercial standards for use in soaps and cosmetics.
    Type: Grant
    Filed: February 7, 1983
    Date of Patent: August 21, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Richard B. Lund, Glenn W. Brown
  • Patent number: 4448959
    Abstract: Chlorosulfonyl urea compounds of the formula: ##STR1## wherein X is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl, methoxyethyl, CF.sub.3 or chlorine, andY is C.sub.1 -C.sub.2 -alkyl, C.sub.1 -C.sub.3 -alkoxy, C.sub.1 -C.sub.2 -alkylthio, methoxymethyl or methoxyethyl.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: May 15, 1984
    Assignee: Ciba-Geigy Corporation
    Inventor: Beat Bohner
  • Patent number: 4423220
    Abstract: A new process for the production of O,O-dialkylphosphorodithioates of the formula ##STR1## wherein R represents methyl or ethyl, and R.sub.1 and R.sub.2 are identical or different, and each represent an alkyl, alkenyl or alkoxyalkyl group having in each case at most 5 carbon atoms is disclosed. The process comprises reacting an essentially equimolar mixture of a piperidine of the formula ##STR2## and a free O,O-dialkyldithiophosphoric acid of the formula ##STR3## or a sodium, potassium or ammonium salt thereof, in the presence of an acid binding agent, with chloroacetylchloride.
    Type: Grant
    Filed: November 26, 1979
    Date of Patent: December 27, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Pierre Ledouble, Markus Tschopp