Halogen In Acid Moiety Patents (Class 560/65)
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Patent number: 4594444Abstract: If the transesterification of esters of the formula II ##STR1## with alcohols of the formula III ##STR2## is catalyzed by treatment with catalytic amounts of an oxide or an organo-metallic compound of a metal of the fourth main group or subgroup of the periodic system, and if the resulting melt is then distilled in a flash distillation apparatus under specific conditions, compounds of the formula ##STR3## are obtained in a virtually quantitative yield. In the above formulae, R is methyl or ethyl, A is a radical of an m-hydric aliphatic alcohol, E is methyl or tert-butyl, m is 1 to 4 and n is 0 to 2. The products thus obtained do not contain any interfering by-products and do not have to be additionally purified.Type: GrantFiled: December 12, 1984Date of Patent: June 10, 1986Assignee: Ciba-Geigy CorporationInventor: Ivan Orban
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Patent number: 4584318Abstract: A method is described for the control of nematodes in agricultural crops which comprises applying to the situs of infestation of a nematicidal composition containing as active ingredient a compound of the formula ##STR1## wherein Q is hydroxy, carbamoyloxy, or acyloxy, R is alkyl, alkenyl, alkynyl, X is halogen or methyl, n is 1 or 2. Preparation of active ingredient compounds is described, and nematicidal utility of compositions is exemplified.Type: GrantFiled: June 20, 1983Date of Patent: April 22, 1986Assignee: FMC CorporationInventors: Clinton J. Peake, Carmine P. DiSanzo, John F. Engel
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Patent number: 4582856Abstract: Pesticidally active 2,2-dimethyl-3-(2-halogeno-vinyl)-cyclopropanecarboxylic acid esters of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and represent alkyl or halogenoalkyl,R.sup.3 represents alkyl or the grouping --(CH.sub.2)--.sub.n R.sup.4,in whichn represent 0 or 1 andR.sup.4 represents halogenoalkyl, optionally substituted aryl or the grouping --XR.sup.5,in whichX represents oxygen or sulphur andR.sup.5 represents alkyl, halogenoalkyl, optionally substituted aryl or optionally substituted aralkyl,Hal represents fluorine, chlorine or bromine andR represents an alcohol radical which can be used in the case of pyrethroids.Intermediates carrying an acid, acid chloride or alkyl ester group in place of --COOR are also new.Type: GrantFiled: March 20, 1984Date of Patent: April 15, 1986Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Benedikt Becker, Bernhard Homeyer, Wilhelm Stendel
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Patent number: 4550981Abstract: Compounds of the formula ##STR1## wherein X.sup.2 is a single covalent bond or --COO--; X.sup.1 is a single covalent bond, --COO--, --CH.sub.2 CH.sub.2 -- or when X.sup.2 is --COO--, X.sup.1 also can be p--C.sub.6 H.sub.4 --, p--C.sub.6 H.sub.4 --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 --p--C.sub.6 H.sub.4, p--C.sub.6 H.sub.4 --COO-- or --COO--p--C.sub.6 H.sub.4 ; ring A is a benzene ring or trans-1,4-cyclohexylene; ring B is a benzene ring or when X.sup.2 is --COO-- and X.sup.1 is a single covalent bond, --COO-- or --CH.sub.2 CH.sub.2 --, ring B also can be trans-1,4-cyclohexylene; Z.sup.1, Z.sup.2 and Z.sup.3 individually are hydrogen or when positioned on a benzene ring which is not linked directly with a further ring via a single covalent bond, Z.sup.1, Z.sup.2 and Z.sup.3 also can be halogen, cyano or methyl; Y.sup.2 is cyano, nitro, 2,2-dicyanovinyl or when Y.sup.1 is hydrogen Y.sup.2 also can be 2,2-dicyano-1-methylvinyl; Y.sup.1 is halogen, cyano, C.sub.1 -C.sub.3 -alkyl or, when X.sup.Type: GrantFiled: September 9, 1983Date of Patent: November 5, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4551264Abstract: New polyhalogenoaromatic compounds of Formula I ##STR1## wherein Y and Z are each independently alkyl, alkoxy or alkanoyl each of 1 to 12 C atoms, --COOR.sup.1, --O--CO--R.sup.1, CN, NO.sub.2, NH.sub.2 or OH;Q is one or two identical or different radicals selected from Ph, Cy, 1,4-bicyclo[2,2,2]octylene or 1,3-dioxane-2,5-diyl;X.sup.1 to X.sup.4 are each independently H, F, Cl or Br;R.sup.1 is alkyl of 1 to 4 C atoms, Ph--R.sup.2 or Cy--R.sup.2 ;R.sup.2 is alkyl or alkoxy each of 1-12 C atoms or CN;Ph is 1,4-phenylene; and Cy is 1,4-cyclohexylene,can be used as components of liquid-crystal dielectrics.Type: GrantFiled: March 14, 1983Date of Patent: November 5, 1985Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Michael Romer, Georg Weber
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Patent number: 4546196Abstract: The subject matter of this application is the new compound, 3-chlorobenzyl-3,6-dichloro-2-methoxybenzoate and its use as a sugarcane ripener.Type: GrantFiled: June 11, 1984Date of Patent: October 8, 1985Assignee: Velsicol Chemical CorporationInventors: George F. Luteri, Leonard J. Stach, Louis G. Nickell
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Patent number: 4545921Abstract: The invention relates to a group of organic compounds of the substituted 2-hydroxyfluorene ester type, which has a smectic A mesomorphous phase. The invention also relates to the process for producing molecules of this group.The compound according to the invention is in accordance with the general chemical formula ##STR1## whereby n can be between 1 and 15 and X=Br or CN. The invention applies to the field of liquid crystals and to display means using such crystals.Type: GrantFiled: December 29, 1983Date of Patent: October 8, 1985Assignee: Thomson-CSFInventors: Jean-Claude Dubois, Gilles Ravaux, Pierre Le Barny
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Patent number: 4540522Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.Type: GrantFiled: October 7, 1983Date of Patent: September 10, 1985Assignee: Monsanto CompanyInventors: John P. Chupp, Terry M. Balthazor
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Patent number: 4532343Abstract: Aromatic retinoic acid analogues of the formula ##STR1## where X is hydrogen or fluorine, Y is hydrogen, halogen of atomic number 9 or 17, hydroxy, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms and R is hydroxy, alkoxy, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl, or aryl and R.sup.2 is alkyl or aryl, with the proviso that when Y is hydrogen, X is fluorine. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: November 19, 1982Date of Patent: July 30, 1985Assignee: SRI InternationalInventors: Marcia I. Dawson, Peter D. Hobbs
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Patent number: 4531009Abstract: A process for producing an .alpha.,.omega.-bis(2-chlorophenoxy)alkane-4,4'-dicarboxylic acid or its ester, that has a high Young's modulus and that is useful as a material for polyesters capable to form self-extinguishing fibers and films. Thus .alpha.,.omega.-bis(2-chlorophenoxy)alkane-4,4'-dicarboxylic acid or its ester is obtained by reacting .alpha.,.omega.-bis(phenoxy)alkane-4,4'-dicarboxylic acid or its ester with chlorine in the presence of a solvent selected from the group consisting of lower fatty acid having 2 to 6 carbon atoms, hydrocarbon chloride having 1 to 8 carbon atoms, and carbon chloride having 1 to 2 carbon atoms, in high yield.Type: GrantFiled: September 12, 1983Date of Patent: July 23, 1985Assignee: Toray Industries, Inc.Inventors: Toshihide Inoue, Hideo Komatsu
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Patent number: 4526704Abstract: Compounds of the formula ##STR1## wherein n is 0 or 1; one of X.sup.1 and X.sup.2 is --COO-- or --OOC-- and the other is a single covalent bond or --CH.sub.2 CH.sub.2 --; X.sup.3 and X.sup.4 individually are a single covalent bond or --CH.sub.2 CH.sub.2 --, with the proviso that at most one of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 is --CH.sub.2 CH.sub.2 --; rings A.sup.1 and A.sup.5 individually are a group of the formula ##STR2## or trans-1,4-cyclohexylene; rings A.sup.2, A.sup.3 and A.sup.4 individually are a group of formula II or, when ring A.sup.2, A.sup.3 or A.sup.4 is not linked with at least one of the other two of these rings by a single covalent bond then such ring also can be trans-1,4-cyclohexylene, with the proviso that at least one of rings A.sup.1 through A.sup.5 is a group of formula II; Y is hydrogen, or when Y is attached to a ring of formula II which is not linked with another ring via a single covalent bond, Y also can be fluorine, chlorine or methyl; and R.sup.1 and R.sup.Type: GrantFiled: July 11, 1983Date of Patent: July 2, 1985Assignee: Hoffmann-La Roche Inc.Inventors: Martin Petrzilka, Martin Schadt, Alois Villiger
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Patent number: 4501895Abstract: This invention relates to novel compounds for preventing or retarding the degradation of elastin or other proteins and therefore preventing or retarding the disease states caused by said degradation, of the formula: ##STR1## or its pharmacologically acceptable salts. The invention also relates to novel methods and intermediates for making the compounds. The intermediate compound being of the formula: ##STR2## wherein R.sub.2 is (a) halogen; or(b) trifluoromethyl;wherein R.sub.3 is(a) --C(O)R.sub.4 ;(b) --CH(OH)R.sub.4 ;(c) --CH.sub.2 R 4; or(d) --CH.dbd.CHR.sub.4 ;wherein R.sub.4 is alkyl or 13 to 25 carbon atoms inclusive, and the pharmacologically acceptable base addition salts thereof.Type: GrantFiled: July 2, 1984Date of Patent: February 26, 1985Assignee: G.D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4490278Abstract: The invention relates to liquid crystal nematic substances for electro-optical devices for the modulation of light, for the reproduction of numerals, signs and images as well as an orienting medium for spectroscopy and gas chromatography.It was found that compounds containing two or three rings, connected by carboxyl groups are new liquid crystal nematic substances of the general formula ##STR1## where R.sup.1 =C.sub.n H.sub.2n+1, CN; R.sup.2 =C.sub.m H.sub.2m+1, CN;R.sup.3 =H, CH.sub.3, C.sub.2 H.sub.5 Cl, Br; x=0 or 1; m,n=numbers from 1 to 10 are suitable for electro-optical arrangements for the modulation of transmitted or reflected light as well as for the reproduction of numeral signals and images, and further, as an orienting medium for spectroscopy and gas chromotography.Other liquid crystal substances or non-liquid crystalline substances, particularly dyes, may be added to the substances according to the invention.Type: GrantFiled: September 22, 1980Date of Patent: December 25, 1984Inventors: Herrmann Schubert, Hans-Joachim Deutscher, Horst Kresse, Dietrich Demus, Heinz Altmann, Marlies Korber, Ute Bottger
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Patent number: 4487954Abstract: Liquid crystal compounds useful as a component of liquid crystal compositions having superior actuation characteristics within a broader temperature range are provided, which compounds are carboxylic acid cyclohexyl ester derivatives expressed by the general formula ##STR1## wherein A represents ##STR2## R- or RO-; B represents ##STR3## R represents an alkyl group or an alkoxy group, both having 1 to 10 carbon atoms; and R' represents an alkyl group having 1 to 10 carbon atoms.Type: GrantFiled: September 17, 1981Date of Patent: December 11, 1984Assignee: Chisso CorporationInventors: Shigeru Sugimori, Tetsuhiko Kojima, Masakazu Tsuji
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Patent number: 4486355Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.Type: GrantFiled: April 25, 1983Date of Patent: December 4, 1984Assignee: Imperial Chemical Industries PLCInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4484008Abstract: This invention relates to an improvement in the process of isolating certain diphenyl ethers from an aprotic organic solvent by the addition of a diphenyl ether phase forming amount of water to a reaction mixture comprising a liquid phase of the diphenyl ether dissolved in the solvent.Type: GrantFiled: September 30, 1982Date of Patent: November 20, 1984Assignee: PPG Industries, Inc.Inventors: James A. Cook, Jr., James A. Manner
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Patent number: 4476320Abstract: Ortho-substituted fluoroaromatic compounds are prepared by reaction of corresponding anilines, which are substituted in the o-position, with alkyl nitrites in the presence of alcohols and/or ethers and in the presence of boron trifluoride or boric acid esters and hydrogen fluoride, and by isolation and decomposition of the diazonium tetrafluoborate produced.Type: GrantFiled: September 29, 1982Date of Patent: October 9, 1984Assignee: Bayer AktiengesellschaftInventors: Herbert Diehl, Heinrich Pelster, Hubert Habetz
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Patent number: 4469885Abstract: This invention relates to novel compounds for preventing or retarding the degradation of elastin or other proteins and therefore preventing or retarding the disease states caused by said degradation, of the formula: ##STR1## or its pharmacologically acceptable salts. The invention also relates to novel methods and intermediates for making the compounds.Type: GrantFiled: May 9, 1983Date of Patent: September 4, 1984Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4463014Abstract: Esters in their stereoisomeric form or mixtures thereof of the formula ##STR1## wherein R.sub.1 and R are different and individually selected from the group consisting of hydrogen, fluorine and bromine, R.sub.2 is selected from the group consisting of --CN and --C.tbd.CH and R.sub.3 is a hydrocarbyl group having pesticidal properties and their preparations.Type: GrantFiled: April 5, 1982Date of Patent: July 31, 1984Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4440943Abstract: 3,7-Substituted phenoxiodinin-5-ium compounds are effective against a variety of aerobic and anaerobic bacteria as well as fungi. The compounds of this invention may be prepared by the direct iodination of a suitably substituted diphenyl ether with iodosyl sulfate in concentrated sulfuric acid. The resulting bisulfate anion may be exchanged with a desired anion by standard metathetic processes.Type: GrantFiled: March 15, 1982Date of Patent: April 3, 1984Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
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Patent number: 4440945Abstract: Novel heat-curable acetylene-terminated monomers are provided which exhibit an optically anisotropic melt phase at a temperature which enables it to undergo melt processing in the formation of molded articles, etc. The monomers are capable of being heat-cured at temperatures in excess of the melt processing temperatures to produce a thermoset self-reinforced composite.Type: GrantFiled: July 19, 1982Date of Patent: April 3, 1984Assignee: Celanese CorporationInventors: Anthony B. Conciatori, Eui W. Choe, Gerald Farrow
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Patent number: 4431668Abstract: Cyclopropane carboxylic acid ester derivatives and optical and geometrical isomers thereof expressed by the general formula: ##STR1## wherein R.sub.1 represents hydrogen atom or methyl group, R.sub.2 represents alkyl group, alkenyl group, haloalkyl group, haloalkenyl group having 1-6 carbon atoms and a group selected from the groups of the general formulae (II), (III) and (IV): ##STR2## in which n is an integer of 2-5, R.sub.4 represents methyl group, chlorine atom or methoxy group, and R.sub.3 represents a group selected from the groups of the general formulae (V), (VI), (VII), (VIII), (IX) and (X): ##STR3## in which X represents oxygen atom or vinylene group, R.sub.5 represents allyl group, propargyl group, benzyl group, phenoxy group or 2,2-dichlorovinyloxy group, R.sub.6 represents hydrogen atom, methyl group or halogen atom, R.sub.7 represents hydrogen atom, cyano group, ethynyl group or trifluoromethyl group and m is an integer of 1-2, R.sub.Type: GrantFiled: November 14, 1978Date of Patent: February 14, 1984Assignee: Dainippon Jochugiku Kabushiki KaishaInventors: Yoshio Katsuda, Yoshihiro Minamite
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Patent number: 4417071Abstract: A process for the manufacture of phenols of the formula I ##STR1## wherein R.sub.1 is alkyl of 1 to 18 carbon atoms, cycloalkyl, phenyl, aralkyl or chlorine, R.sub.2 is hydrogen or has the same meaning as R.sub.1, R.sub.3 is hydrogen or alkyl of 1 to 12 carbon atoms, R.sub.4 is alkylene of 2 to 18 carbon atoms which is unsubstituted or substituted by aryl or hydroxyl, and n is an integer from 0 to 4, which process comprises transesterifying a compound of the formula II ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined for formula (I) and R.sub.5 is alkyl of 1 to 4 carbon atoms with a mercapto alcohol of the formulaHO--R.sub.4 --SHwherein R.sub.4 is as defined for formula (I), in the presence of a catalyst of the formula (R.sub.6 O).sub.4 M, wherein R.sub.6 represents alkyl radicals of 1 to 18 carbon atoms which can be the same or different, aryl or alkaryl, and M is an element selected from the group consisting of Ti, Ge, Zr, Sn or V.Type: GrantFiled: March 11, 1982Date of Patent: November 22, 1983Assignee: Ciba-Geigy CorporationInventor: Siegfried Rosenberger
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Patent number: 4408059Abstract: Milbemycin and avermectin macrolides are synthesized by the cyclized linking of separately synthesized northern and southern hemisphere intermediates. The northern hemisphere intermediate is a spiroketal alkenyl aldehyde, and the southern hemisphere intermediate is an aryl alkenyl phosphine oxide anion.Type: GrantFiled: December 4, 1981Date of Patent: October 4, 1983Assignee: University Patents, Inc.Inventors: Amos B. Smith, III, Steven R. Schow
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Patent number: 4406814Abstract: Disclosed is a new family of Liquid Crystalline Materials for use in optical display devices having the general formula: ##STR1## The members of the family of materials are characterized by having a broad nematic operating range in conjunction with low viscosity and exhibit fast response times to a controlled electrical field in the lower temperature regions of their nematic operating range and may be mixed with other members of the family or with other liquid crystalline materials and/or homologous non-liquid crystalline materials.Type: GrantFiled: April 10, 1981Date of Patent: September 27, 1983Assignee: Eaton CorporationInventor: Joseph P. Ferrato
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Patent number: 4402855Abstract: A family of liquid crystals having a type A smectic mesophase with a positive dielectric anisotropy, which are particularly useful in the case of the thermo-optical effect.The substances of the family are in accordance with the general formula: ##STR1## in which R represents an organic group of the alkyl or alkoxy type containing 1 to 15 carbon atoms and in which X and Y designate either the bromine or the nitrile radical.Type: GrantFiled: July 15, 1981Date of Patent: September 6, 1983Assignee: Thomson-CSFInventors: Annie Zann, Jean-Claude Dubois
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Patent number: 4397864Abstract: The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.Type: GrantFiled: April 14, 1981Date of Patent: August 9, 1983Assignee: Mitsuitoatsu Chemicals Inc.Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Kenji Kodaka, Tsutomu Ishii, Teruhiko Toyama, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
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Patent number: 4390716Abstract: Substituted 2-(trifluoroethoxy)benzamide, benzoic acid and benzoate compounds which are intermediates in the preparation of pharmaceutically active agents.Type: GrantFiled: May 5, 1982Date of Patent: June 28, 1983Assignee: Riker Laboratories, Inc.Inventor: Elden H. Banitt
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Patent number: 4388473Abstract: This invention relates to substituted benzoic acid or phenylacetic acid ester compounds exhibiting meristematic activity and to the use of such compounds in regulating plant growth.Type: GrantFiled: October 29, 1981Date of Patent: June 14, 1983Assignee: PPG Industries, Inc.Inventors: Sidney B. Richter, Barry Van Gemert
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Patent number: 4388472Abstract: A compound of the formula: ##STR1## and salts and esters thereof, useful as intermediates for the preparation of compounds of the formula ##STR2## wherein R.sup.1 is an alkyl group optionally substituted by one or more fluorine atoms or by an optionally substituted phenyl group R.sup.2 is No.sub.2 or Cl and R.sup.6 is a hydrogen atom or an alkyl group of 1 to 4 carbon atoms.Type: GrantFiled: January 13, 1981Date of Patent: June 14, 1983Assignee: Imperial Chemical Industries PLCInventors: David Cartwright, David J. Collins
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Patent number: 4385070Abstract: Compounds of formula I wherein R.sup.1 and R.sup.2 are each selected from halomethyl and halo and R is nitro, cyano, lower alkoxycarbonyl, lower alkylcarbonyl, or di- or trifluoromethyl, and n has a value of zero to four, and compositions comprising them are useful as insecticides in agriculture, horticulture and other outlets. They may optionally be combined with other pesticides and/or synergists. The compounds may be prepared by conventional esterification processes from the corresponding acids and appropriately substituted benzyl alcohols or halides, some of which are novel.Type: GrantFiled: January 28, 1980Date of Patent: May 24, 1983Assignee: Imperial Chemical Industries LimitedInventors: Philip D. Bentley, Nazim Punja
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Patent number: 4384135Abstract: A method of preparing a diphenyl ether compound of the formula (II) ##STR1## wherein X is F, Cl or Br; Z is hydrogen, halogen, NO.sub.2 of CN; and W is methyl, cyano, CH.sub.3 CO--, or a group --C--OR, wherein R is --OH; --OM wherein M is a cation; OR.sup.1 wherein R.sup.1 is an optionally substituted aliphatic radical; --NR.sup.2 R.sup.3 wherein R.sup.2 and R.sup.3 are each hydrogen or an optionally substituted aliphatic radical; or --NHSO.sub.2 R.sup.4 wherein R.sup.4 is alkyl of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol. The invention further comprises novel 3-X-4,5-difluorobenzotrifluorides for use in the process.Type: GrantFiled: January 19, 1981Date of Patent: May 17, 1983Assignee: Imperial Chemical Industries LimitedInventors: David Cartwright, Roger Salmon, Alfred G. Williams
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4368135Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.Type: GrantFiled: June 30, 1980Date of Patent: January 11, 1983Assignee: BBC, Brown, Boveri & Company, Ltd.Inventor: Maged A. Osman
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Patent number: 4365077Abstract: 11-Desoxy-16-aryloxy-.omega.-tetranorprostaglandins are disclosed. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins but they exhibit a greater tissue specificity of action.Type: GrantFiled: February 22, 1979Date of Patent: December 21, 1982Assignee: Pfizer Inc.Inventors: Jasjit S. Bindra, James F. Eggler, Michael R. Johnson, Thomas K. Schaaf
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Patent number: 4344963Abstract: 2-Phenyl-alk-1-enyl-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R each independently ishydrogen, halogen, cyano, nitro and, in each case optionally halogen-substituted, alkyl, alkoxy, alkylenedioxy or alkylthio,R.sup.1 is optionally halogen-substituted alkyk, andR.sup.2 is a radical customary in the alcohol part of pyrethroidswhich exhibit insecticidal and acaricidal activity. They are made from the corresponding alkyl esters which are new and made by novel processes.Type: GrantFiled: April 25, 1980Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
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Patent number: 4334914Abstract: Novel benzoate derivatives having a powerful herbicidal effect on various weeds grown in paddy fields, upland fields, and other places have been found out, which are represented by the formula ##STR1## wherein X is --SR, --O--CH.sub.2 CH.sub.2 O).sub.n R, --OCH.sub.2 CH.sub.2 SR, ##STR2## herein R being lower alkyl and n being an integer of 1 to 3.Type: GrantFiled: February 12, 1981Date of Patent: June 15, 1982Assignee: Nihon Nohyaku Co., Ltd.Inventors: Kunikazu Hiraga, Katsumasa Okawa, Kenichi Ikeda, Masanori Hikawa
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Patent number: 4334915Abstract: A phenoxyphthalate of the formula ##STR1## wherein X represents chlorine atom or trifluoromethyl group and R and R' represent methyl or ethyl group, is novel and has a strong herbicidal activity.Type: GrantFiled: February 22, 1980Date of Patent: June 15, 1982Assignee: Nihon Nohyaku Co. Ltd.Inventors: Kunikazu Hiraga, Masakazu Shibayama, Katsumasa Ohkawa, Tatsuo Harada
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1H-Inden-1-one derivatives, their use in microbicidal compositions, and for combating microorganisms
Patent number: 4333949Abstract: 2,3-Dichloro-7-hydroxy-1H-inden-1-one derivatives of the formula I ##STR1## wherein R.sub.1 is hydrogen or one of the groups ##STR2## R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or nitro,R.sub.4 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.4 -alkenyl, each of which is unsubstituted or substituted by halogen, or R.sub.4 is phenyl which is unsubstituted or is substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, trifluoromethyl, cyano or nitro, or it is a C.sub.3 -C.sub.6 -cycloalkyl group, andR.sub.5 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl or C.sub.2 -C.sub.4 -alkenyl.These compounds exhibit a microbicidal action against in particular phytopathogenic fungi and bacteria.Type: GrantFiled: June 5, 1981Date of Patent: June 8, 1982Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler -
Patent number: 4328202Abstract: Ionic compounds of the formula ##STR1## wherein X is --CONR.sub.1 R.sub.2, --CH.sub.2 NH.multidot.Acyl or --CH.sub.2 OH; Y is --NR.sub.3 R.sub.4, --NH.multidot.Acyl or OR.sub.5 ; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 can be identical or different, and each is hydrogen, C.sub.1-6 - alkyl or C.sub.2-8 -alkyl substituted by 1-5 OH groups and/or by one C.sub.1-3 -alkoxy group, R.sub.5 is C.sub.1-6 alkyl or C.sub.2-8 -alkyl substituted by 1-5 OH groups and/or by one C.sub.1-3 -alkoxy group, and Acyl, which can be the same or different in X and Y, is C.sub.2-6 -alkanoyl or C.sub.2-6 -alkanoyl substituted by 1-4 OH groups and/or by one C.sub.1-3 -alkoxy group, or a physiologically compatible salt thereof with an inorganic or organic base, have valuable properties as X-ray contrast agents.Type: GrantFiled: January 9, 1981Date of Patent: May 4, 1982Assignee: Schering, A.G.Inventors: Heinz Gries, Heinrich Pfeiffer, Ulrich Speck, Wolfgang Muetzel
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Patent number: 4326055Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.Type: GrantFiled: December 15, 1978Date of Patent: April 20, 1982Assignee: Hoffmann-La Roche Inc.Inventor: Peter Loeliger
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Patent number: 4323692Abstract: This process relates to the oxidation of phenoxytoluenes to phenoxybenzoic acids utilizing a hydrogen peroxide activated, bromide promoted cobalt catalyst which can be performed at atmospheric pressure and at moderate temperatures. These phenoxybenzoic acids can then be esterified and selectively nitrated to give the corresponding 2-nitro-5-(substituted)phenoxybenzoic acid esters. Alternatively the acids can be nitrated and then esterified.Type: GrantFiled: August 4, 1978Date of Patent: April 6, 1982Assignee: Rohm and Haas CompanyInventor: Charles M. Tanger
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Patent number: 4316913Abstract: Substituted styrylcyclopropanecarboxylic acid esters of the formula ##STR1## in which R represents C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 represents alkoxy or alkylthio, either of which is optionally substituted by halogen andR.sup.2 represents hydrogen or alkoxy, orR.sup.1 and R.sup.2 together represent optionally halogen-substituted alkylenedioxy, andR.sup.3 represents hydrogen or chlorine,exhibit arthropodicidal activity. A novel synthesis is shown involving reaction of ##STR2## in the presence of an alkali metal cyanide to produce an end product wherein R is an .alpha.-cyano-3-phenoxybenzyl ester. ##STR3## is reacted with ##STR4## in the presence of a base to produce certain novel intermediates.Type: GrantFiled: March 31, 1980Date of Patent: February 23, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Wilhelm Stendel
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Patent number: 4314070Abstract: An improved process for producing meta-phenoxy benzoic acids and their lower alkyl esters in improved yields and with higher selectivity by reacting an alkali metal phenate with a lower alkyl ester of meta-halobenzoic acid in the presence of a copper sulfate catalyst.Type: GrantFiled: May 14, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc Inc.Inventors: Fred G. Schreiber, Peter S. Gradeff
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Patent number: 4311515Abstract: This invention concerns certain substituted diphenyl ethers having herbicidal activity, their preparation, and the control of weeds therewith.Type: GrantFiled: July 25, 1980Date of Patent: January 19, 1982Assignee: PPG Industries, Inc.Inventor: William S. Grove
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Patent number: 4310700Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.Type: GrantFiled: April 3, 1980Date of Patent: January 12, 1982Assignee: American Cyanamid CompanyInventors: Allan Wissner, Middleton B. Floyd, Jr.
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Patent number: 4309566Abstract: Novel substituted benzoyloxy compounds exhibit plant regulator activity, retarding or stimulating the growth of a variety of broadleaved plants, while leaving grasses unaffected. The preparation and plant regulator activity of the compounds is exemplified.Type: GrantFiled: November 5, 1979Date of Patent: January 5, 1982Assignee: FMC CorporationInventors: Marvin J. Konz, Norman E. Krog
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Patent number: 4308395Abstract: An improved single-pot process for synthesis of 3,5,6-trichlorosalicylic acid and esters thereof is described. Salicylic acid is chlorinated first in concentrated sulfuric acid and then with iodine catalyst to make the trichlorosalicylic acid which is extracted and then reacted with an alcohol to make the ester.Type: GrantFiled: July 11, 1980Date of Patent: December 29, 1981Assignee: American Cyanamid CompanyInventors: Robert J. Manfre, Arthur G. Mohan, Michael M. Rauhut
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Patent number: 4297366Abstract: 2,2-Dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is fluoroalkyl,R.sup.2 is an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, andR.sup.3 is a radical customary in the alcohol component of pyrethroidswhich possess arthropodicidal properties. New intermediates therefor are also shown.Type: GrantFiled: April 23, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: RE31715Abstract: Novel liquid crystal compounds are disclosed, which are chiral esters based upon the phenol ##STR1## Typical examples are: ##STR2## and mixtures of these compounds have a helical pitch such that the mixtures reflect light of a specific wavelength when illuminated with ordinary light and the pitch is temperature sensitive so that the mixtures can be used in temperature indicating devices. Specific examples are given as are samples of mixtures that can be used in phase change electro-optic display devices.Type: GrantFiled: March 27, 1981Date of Patent: October 30, 1984Assignee: The Secretary of State for Defence in Her Britannic Majesty's Government of the United Kingdom of Great Britain and Northern IrelandInventors: David Coates, George W. Gray, Damien G. McDonnell