Oxy Containing Reactant Patents (Class 568/315)
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Patent number: 4376868Abstract: Cresylic acid ethoxylation is catalyzed by basic compounds and salts of alkaline earth metals. Ethoxylates from such reactions have narrow ethylene oxide distributions, lower pour points and lower by-products as compared to alkali base catalyzed ethoxylation. Suitable catalysts include strontium-containing and barium-containing materials. The catalyst also includes co-catalyst combinations using these materials with one or more promoters including polyols, amines, amides, carboxylic acids and phenols. The co-catalyst combinations can be preformed prior to introduction into the reaction mixture.Type: GrantFiled: February 14, 1980Date of Patent: March 15, 1983Assignee: Conoco Inc.Inventors: Gerald L. Nield, Kang Yang, Paul H. Washecheck
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Patent number: 4371711Abstract: A method of producing a 4-hydroxycyclopentenone represented by the formula, ##STR1## wherein R.sub.1 is an alkyl, alkenyl, alkynyl, cycloalkyl, thienyl, phenyl, p-methylbenzyl or benzyl group and R.sub.2 is an alkyl, alkenyl or alkynyl group having 6 or less carbon atoms, which comprises reacting a furylcarbinol compound of the formula, ##STR2## wherein R.sub.1 is as defined above, in the presence of an acid in a mixed solvent of water and an organic solvent, to obtain a cyclopentenone compound of the formula, ##STR3## wherein R.sub.1 is as defined above; reacting the cyclopentenone compound in the presence of an oxidizing agent to obtain a cyclopentendione compound of the formula, ##STR4## wherein R.sub.1 is a defined above; reacting the cyclopentendione compound with a Grignard reagent of the formula,R.sub.2 MgXwherein R.sub.2 is as defined above and X is chlorine, bromine or iodine atom, to obtain an oxocyclopentene compound of the formula, ##STR5## wherein R.sub.1 and R.sub.Type: GrantFiled: May 20, 1980Date of Patent: February 1, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Kenji Saito, Hiroshi Yamachika
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Patent number: 4357278Abstract: What are disclosed are a multi-step synthesis for the preparation of 9(11)-dehydroestrone 3-methyl ether from 2-methyl,4-methoxy benzaldehyde; 1-(4-methoxy-2-methyl-(phenyl)-3-(1-methyl-2-oxo-5-t-vinyl-cyclopent-r-yl) -propane-1-one, an intermediate in said synthesis; and a method for the preparation of 3-vinylcyclopentanone from 2-vinylcyclopropane-1,1-dicarboxylic acid.Type: GrantFiled: April 10, 1981Date of Patent: November 2, 1982Assignee: Hoechst AktiengesellschaftInventors: Gerhard Quinkert, Wolf-Dietrich Weber, Ulrich Schwartz
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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: 4331597Abstract: Penicillin compounds and methods for the production thereof are described, said penicillin compounds being represented by the formula (I) ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 each represents hydrogen, a lower alkyl group, a halogen atom, a lower alkoxy group, a hydroxyl group, or a substituted or unsubstituted phenylalkoxy group except that R.sub.1, R.sub.2, and R.sub.3 cannot all represent hydrogen simultaneously; R.sub.4 represents hydrogen or a lower alkyl group; and R.sub.5 represents hydrogen or a hydroxyl group.Type: GrantFiled: October 2, 1980Date of Patent: May 25, 1982Assignee: Meiji Seika Kaisha, Ltd.Inventors: Osamu Makabe, Yasushi Murai, Tuneo Okonogi, Masahiro Onodera, Takashi Yoshida, Shunzo Fukatsu
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Patent number: 4330482Abstract: In the process for the production of a halogenoalkene of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl or aryl radical or an optionally substituted heterocyclic radical,R.sup.2 represents a halogen atom, a cyano group, an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkenyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl or aminocarbonyl radical or an optionally substituted heterocyclic radical, andX is a halogen atom,in which an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R.sup.3 each independently is an alkyl or phenyl radical, or the two radicals R.sup.3 together are an alkanediyl (alkylene) radical,is reacted with a phosphorus-containing olefinating agent of the formula ##STR3## in which Z.sup.1 is the phosphorus-containing radical ##STR4## R.sup.4 and R.sup.5 each independently is an alkyl, phenyl, alkoxy or phenoxy radical or together are an alkanedioxy radical, andR.Type: GrantFiled: December 18, 1980Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventor: Hellmut Hoffmann
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Patent number: 4323710Abstract: The partial alkylation of a polyhydroxybenzophenone having ortho- and para-hydroxy substituents to form an ortho-hydroxy, para-alkoxy benzophenone is carried out in the presence of a non-aqueous solvent, viz. a polyethylene glycol or its mono or dialkylated derivatives, whereby high yields of alkylated product are obtained in shorter reaction times.Type: GrantFiled: November 3, 1980Date of Patent: April 6, 1982Assignee: GAF CorporationInventors: Allan Wexler, Paritosh M. Chakrabarti, Michael J. Brown
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Patent number: 4315032Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.Type: GrantFiled: May 14, 1980Date of Patent: February 9, 1982Assignee: Teitin LimitedInventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
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Patent number: 4314086Abstract: Aliphatic/aromatic ethers are prepared by reacting an aliphatic halide with either an alkali or alkaline earth metal, or ammonium phenolate or naphtholate, in an inert organic solvent, and in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: February 2, 1982Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Daniel Michelet
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Patent number: 4310465Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
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Patent number: 4310699Abstract: Bis (phenylglyoxyloyl) benzenes are manufactured by a method comprising the reaction of terephthalic or isophthalic aldehyde first with a low proportion of an alkali metal cyanide in a solvent, and then with benzaldehyde; the resultant product is oxidized to the desired bis (phenylglyoxyloyl) benzene.Type: GrantFiled: May 23, 1980Date of Patent: January 12, 1982Assignee: Institut Francais du PetroleInventors: Guy Rabilloud, Bernard Sillion
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Patent number: 4310702Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.Type: GrantFiled: July 28, 1980Date of Patent: January 12, 1982Assignee: Allied CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4291061Abstract: 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: October 31, 1979Date of Patent: September 22, 1981Assignee: Ciba-Geigy CorporationInventors: Elmar Sturm, Robert Nyfeler
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Patent number: 4289909Abstract: Processes for preparing 1-dichloroacyl-4-(substituted phenoxy)benzenes and intermediates therefor. The processes are characterized by the use of certain catalysts, solvents and reaction conditions which afford improved yields and reaction products which can be purified by simple procedures (e.g. extraction, crystallization, etc.). The processes are especially applicable to manufacturing large quantities of the aforementioned compounds. The products are useful as mite ovacides.Type: GrantFiled: March 3, 1980Date of Patent: September 15, 1981Assignee: Chevron ResearchInventors: Francis J. Freenor, III, Barbara M. Koerber
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Patent number: 4288386Abstract: The Ullman reaction for the preparation of diaryl ethers by coupling aryl halides with metal phenolates is conducted in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: May 12, 1980Date of Patent: September 8, 1981Assignee: Rhone-Poulenc IndustriesInventors: Gerard Soula, Louis Linguenheld
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Patent number: 4287367Abstract: Monoacetals of aromatic 1,2-diketones are manufactured by reacting the corresponding 1,2-diketones, in an organic solvent, with an acid ester (R.sup.1).sub.n X as alkylating agent and an alcoholate (R.sup.2 O).sub.m Me, where R.sup.1 and R.sup.2 are identical or different hydrocarbon radicals of 1 to 12 carbon atoms, which may or may not be substituted, n and m are integers from 1 to 3, X is a monobasic, dibasic or tribasic acid radical and Me is a metal of main groups 1 to 3 of the periodic table of the elements. The resulting diketone monoacetals are particularly suitable for use as photoinitiators in photopolymerizable compositions.Type: GrantFiled: July 30, 1980Date of Patent: September 1, 1981Assignee: BASF AktiengesellschaftInventors: Werner Kuesters, Lucien Thil
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Patent number: 4287213Abstract: Compounds having the formula ##STR1## wherein one of X or Y is chloro and the other is trifluoromethyl or wherein X is hydrogen and Y is chloro and methods of preparing said compounds.The compounds can be prepared by the reaction of the corresponding 1-acetyl substrate with chlorine or sulfuryl chloride and are useful as mite ovacides.Type: GrantFiled: March 3, 1980Date of Patent: September 1, 1981Assignee: Chevron Research CompanyInventor: John W. Kobzina
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Patent number: 4284823Abstract: There is disclosed a process comprising reacting a compound having the general structural Formula II: ##STR1## with a compound having the general Formula III: ##STR2## in the presence of a basic catalyst while dissolved in an organic solvent to yield an aldehyde having the structural Formula I: ##STR3## wherein R.sub.1 and R.sub.2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R.sub.3 and R.sub.4 are the same or different radicals selected from the group consisting of alkyl radicals containing from 1 to 12 carbon atoms, cycloalkyl radicals containing from 5 to 12 carbon atoms, phenyl and substituted phenyl radicals or R.sub.3 and R.sub.4 with the carbon atom to which they are joined may form a cycloalkyl ring of from 5 to 12 carbon atoms, R.sub.5 is selected from the group consisting of hydrogen, alkyl radicals containing from 1 to 12 carbon atoms, or a cycloalkyl radical containing 5 or 6 carbon atoms.Type: GrantFiled: October 15, 1979Date of Patent: August 18, 1981Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline
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Patent number: 4282158Abstract: Derivatives of .alpha.,.beta.-unsaturated ketones having anticonvulsant activity and methods of their preparation from heterocyclic phosphonium salts and acyclic phosphoranes are disclosed.Type: GrantFiled: February 27, 1980Date of Patent: August 4, 1981Assignee: G. D. Searle & Co.Inventor: Richard A. Mueller
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Patent number: 4263212Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.Type: GrantFiled: February 14, 1980Date of Patent: April 21, 1981Assignee: Rikagaku KenkyushoInventors: Pangbu Hong, Hiroshi Yamazaki
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Patent number: 4261922Abstract: Hydroxyalkylphenyl ether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols in the presence of potassium iodide catalyst.Type: GrantFiled: July 26, 1979Date of Patent: April 14, 1981Assignee: The Dow Chemical CompanyInventor: Kenneth M. Kem
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Patent number: 4258175Abstract: There is provided a process for preparing a compound of the formula ##STR1## wherein X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from the group consisting of fluorine, chlorine, bromine and iodine; n is an integer of from 1 to about 100; a, b, c, and d are each integers of from about 0 to about 4; Z.sup.1 and Z.sup.2 are independently selected from the group consisting of halogen and alkyl of from about 1 to about 15 carbon atoms; R.sup.1 and R.sup.2 are independently selected from the group consisting of alkylene containing from about 1 to about 12 carbon atoms, alkylenyl containing from about 2 to about 12 carbon atoms, cycloalkylene of the formula ##STR2## wherein R.sup.3, R.sup.4 and R.sup.5 are independently selected from the group consisting of alkylene of from about 1 to about 5 carbon atoms, and cycloalkylenyl of the formula ##STR3## and A is selected from the group consisting of R.sup.3 CR.sup.Type: GrantFiled: July 6, 1979Date of Patent: March 24, 1981Assignee: Velsicol Chemical CorporationInventor: Sun-Mao Chen
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Patent number: 4255434Abstract: Fungicidal 1-(azol-1-yl)-4-halo-1-phenoxy-butan-2-ones and -ols of the formula ##STR1## in which R represents alkyl with 1 to 4 carbon atoms;X represents hydrogen, alkyl with 1 to 4 carbon atoms or halogen;Y represents halogen;Z represents halogen, straignt-chain or branched alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy with one or 2 carbon atoms, alkylthio with 1 or 2 carbon atoms, alkoxycarbonyl with 1 to 5 carbon atoms in the alkoxy part, amino, cyano, nitro, phenyl or phenoxy substituted with at least one of halogen, amino, cyano, nitro and alkyl with 1 to 2 carbon atoms, phenylalkyl with 1 or 2 carbon atoms on the alkyl part optionally substituted in the alkyl part by alkylcarbonyl with a total of up to 3 carbon atoms and in the phenyl part by halogen, nitro or cyano;n represents 0,1,2 or 3,A is --CO-- or CH(OH)--, andB is --N.dbd. or --CH.dbd., or a salt thereof.Type: GrantFiled: November 27, 1978Date of Patent: March 10, 1981Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Karl Buchel, Paul-Ernst Frohberger, Wilhelm Brandes, Hans Scheinpflug
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Patent number: 4252818Abstract: 7-[3-(4-Acetyl-3-hydroxy-6-iodo-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8- propyl-4H-1-benzopyran-2-carboxylic acid and its pharmaceutically acceptable salts are employed as antagonists of SRS-A (the slow reacting substance of anaphylaxis) in the treatment of asthma and allergic diseases.Type: GrantFiled: August 2, 1979Date of Patent: February 24, 1981Assignee: Merck & Co., Inc.Inventors: Joshua Rokach, Pierre A. Hamel, Ralph F. Hirschmann
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Patent number: 4228105Abstract: A process for the production of compounds of formula I, ##STR1## wherein R.sub.1 is alkyl of 1 to 3 carbon atoms,R.sub.2 is hydrogen, fluorine, chlorine or bromine, andR.sub.3 is bromine, iodine, isobutyl, tert. butyl, cyclohexyl, cyclohexenyl; or phenyl, optionally substituted by fluorine, chlorine, bromine or alkoxy of 1 to 4 carbon atoms; or a radical of formula II, ##STR2## in which either R.sub.4 and R.sub.5 are the same or different and each signifies alkyl of 1 to 3 carbon atoms,orR.sub.4 and R.sub.5 together signify the radical --(CH.sub.2).sub.n --, in which n is 4 or 5, the radical --CH.sub.2 --CH.sub.2 --0--CH.sub.2 --CH.sub.2 --, the radical --CH.sub.2 --CH.dbd.CH--CH.sub.2 --, or the radical --CH.sub.2 --CH.sub.2 --N(R.sub.6)--CH.sub.2 --CH.sub.2 --, in which R.sub.6 is hydrogen or alkyl of 1 to 3 carbon atoms. Hydroxyketone and hydroxy imine intermediates are also disclosed.The compounds of formula I are known to exhibit anti-inflammatory activity.Type: GrantFiled: November 27, 1978Date of Patent: October 14, 1980Assignee: Sandoz Ltd.Inventor: Rudiger Jeck
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Patent number: 4227015Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.Type: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: 4221741Abstract: This invention provides a process for the preparation of 4-(6'-methoxy-2'naphthyl)-butan-2-one, which process comprises the hydrogenation of 4-(6' methoxy-2'-naphthyl)-4-hydroxy-but-3-en-2-one.Type: GrantFiled: January 19, 1979Date of Patent: September 9, 1980Assignee: Beecham Group LimitedInventor: Laramie M. Gaster
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Patent number: 4218468Abstract: There are provided insecticidal ketones having the general structure: ##STR1## insecticidal compositions containing the ketones and a carrier, and the method of controlling insects with the ketones.Type: GrantFiled: November 13, 1978Date of Patent: August 19, 1980Assignee: Mobil Oil CorporationInventor: Jill H. Paul
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Patent number: 4212762Abstract: Novel mesomorphic substances, constituting, in certain temperature ranges, nematic or smectic liquid crystals which are compounds of the formula: ##STR1## wherein R.sub.1 is an alkyl or alkoxy group containing 1 to 10 atoms of carbon;R.sub.2 is Br, CN or an alkyl (or an alkoxy) group containing 1 to 10 atoms of carbon.Type: GrantFiled: November 21, 1978Date of Patent: July 15, 1980Assignee: Thomson-CSFInventors: Jean-Claude Dubois, Huu Tinh Nguyen, Annie Zann
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Patent number: 4208425Abstract: Beta-diketones substituted by an aryl-aliphatic group in which the aliphatic chain is interrupted by a cyclic group, and useful as anti-viral agents, are prepared by interacting the appropriate aryl-aliphatic halide with an alkali metal salt of a beta-diketone.Type: GrantFiled: October 10, 1978Date of Patent: June 17, 1980Assignee: Sterling Drug Inc.Inventor: Guy D. Diana