Halogen Containing Patents (Class 568/655)
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Patent number: 4453018Abstract: An alkylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with an alkyl sulfite of the formula (RO).sub.2 SO in which R is a one to four carbon alkyl group, the reaction occurring in one step and without the intermediate preparation of a phenolate.Type: GrantFiled: April 1, 1982Date of Patent: June 5, 1984Assignee: International Telephone and Telegraph CorporationInventor: Randall B. Nelson
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Patent number: 4453017Abstract: A methylated phenolic ether is prepared by reacting in the absence of a protic solvent a phenolic compound containing an unreacted phenolic hydroxy group with trimethyl phosphate, the reaction occurring in one step and without the intermediate preparation of a phenolate.Type: GrantFiled: April 1, 1982Date of Patent: June 5, 1984Assignee: International Telephone and Telegraph CorporationInventor: Randall B. Nelson
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Patent number: 4424393Abstract: This invention relates to a process for preparing herbicidally active substituted diphenylethers. Also, this invention provides novel intermediates useful in the production of said diphenylethers.Type: GrantFiled: August 24, 1981Date of Patent: January 3, 1984Assignee: PPG Industries, Inc.Inventors: Frederick F. Guzik, Steven E. Pamer, Sidney B. Richter
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Patent number: 4423249Abstract: Alkyl or aryl 1,1-difluoroalkyl ethers, e.g., 1,1,2-trifluoro-2-chloro-2-iodoethyl phenyl ether, are prepared by reacting an alkoxide or phenoxide with a 1,1-difluoro-1,2-dihaloethane (with the proviso that halo is not fluoro and at least one of the halo substituents is bromo or iodo) in an organic solvent at temperatures ranging from about -30.degree. C. to about 100.degree. C. These compounds may be dehalogenated with zinc to form the corresponding vinyl ethers.The reaction of halogen derivatives of fluorocarbons with nucleophiles is dramatically facilitated by a bromo or iodo substituent in the beta position.Type: GrantFiled: August 26, 1981Date of Patent: December 27, 1983Assignee: The Dow Chemical CompanyInventors: William P. Carl, Bobby R. Ezzell
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Patent number: 4412082Abstract: A novel process for preparing 4-hydroxyphenylacetic acid which is useful as an intermediate for pharmaceutical is provided. A method for preparing 4-hydroxyphenylacetic acid comprising the steps of first reacting benzyl phenyl ether with formaldehyde and hydrogen chloride to form 4-benzyloxybenzyl chloride, second reacting the resultant 4-benzyloxybenzyl chloride with an alkali metal cyanide in at least one solvent selected from the group consisting of water and an organic solvent to form 4-benzyloxyphenylacetonitrile, and hydrolyzing the resultant 4-benzyloxyphenylacetonitrile in the presence of an acid catalyst.Type: GrantFiled: March 2, 1982Date of Patent: October 25, 1983Assignee: Nissan Chemical Industries, Ltd.Inventors: Motoo Mutsukado, Shin Yamada
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Patent number: 4407760Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.Type: GrantFiled: September 20, 1982Date of Patent: October 4, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4405640Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.Type: GrantFiled: December 1, 1980Date of Patent: September 20, 1983Assignee: Imperial Chemical Industries PLCInventor: Nazim Punja
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Patent number: 4405529Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.Type: GrantFiled: September 20, 1982Date of Patent: September 20, 1983Assignee: American Cyanamid CompanyInventors: Jack K. Siddens, Sivaraman Raghu
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Patent number: 4404148Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.Type: GrantFiled: September 20, 1982Date of Patent: September 13, 1983Assignee: American Cyanamid CompanyInventor: Jack K. Siddens
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Patent number: 4380546Abstract: Azole compounds of the formula ##STR1## where X is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl or phenyl and m is an integer from 1 to 5, and, if m is greater than 1, the X's can be identical or different, n is an integer from 2 to 5, Z is N or CH and Y is CO or CR.sup.1 OR.sup.2, where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkanoyl, and their crop-tolerated addition salts with acids, and metal complexes.The compounds act as fungicides and growth regulators.Type: GrantFiled: April 29, 1981Date of Patent: April 19, 1983Assignee: BASF AktiengesellschaftInventors: Hubert Sauter, Eberhard Ammermann, Costin Rentzea, Bernd Zeeh, Johann Jung, Ernst-Heinrich Pommer
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Patent number: 4377711Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.Type: GrantFiled: November 4, 1981Date of Patent: March 22, 1983Assignee: Rhone-Poulenc IndustriesInventors: Isabelle Rico, Claude Wakselman
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Patent number: 4375563Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: March 30, 1982Date of Patent: March 1, 1983Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
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Patent number: 4350824Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
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Patent number: 4347148Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.Type: GrantFiled: November 19, 1979Date of Patent: August 31, 1982Assignee: The Lubrizol CorporationInventor: Kirk E. Davis
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4327025Abstract: A process for the preparation of a styrylcyclopropane-1-carboxylic acid ester of the formula ##STR1## in which R is C.sub.1-4 -alkyl or an alcohol radical customary in pyrethroids,R.sup.1 is alkoxy or alkylthio, either of which may be optionally substituted by halogen,R.sup.2 is hydrogen or alkoxy, orR.sup.1 and R.sup.2 together are optionally halogen-substituted alkylenedioxy, andR.sup.3 is hydrogen or chlorine,comprising reacting an ester of the formula ##STR2## in which Hal is chlorine or bromine,with a base.The compounds are insecticidally active. Numerous syntheses of the starting materials, some involving new intermediates, are also shown.Type: GrantFiled: April 7, 1980Date of Patent: April 27, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Jautelat, Dieter Arlt, Reinhard Lantzsch, Rainer Fuchs, Hans-Jochem Riebel, Rolf Schroder, Horst Harnisch
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Patent number: 4315016Abstract: Fungicidal compounds of the formula: ##STR1## wherein R.sub.3 is hydrogen, R.sub.4 is phenyl optionally substituted with one halogen, and R.sub.5 is alkyl having up to 5 carbon atoms, alkenyl having up to 5 carbon atoms, alkynyl having up to 5 carbon atoms or monochlorophenoxymethyl or R.sub.5 is benzyl optionally ring substituted with up to three substituents selected from the class consisting of halogen, alkyl having up to 4 carbon atoms and alkoxy having up to 4 carbon atoms, or a fungicidal acid salt of such a compound.Type: GrantFiled: February 27, 1978Date of Patent: February 9, 1982Assignee: Imperial Chemical Industries LimitedInventors: Sugavanam Balassubramanyan, Margaret C. Shephard
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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: 4306097Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 8, 1980Date of Patent: December 15, 1981Assignee: Pfizer Inc.Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4284827Abstract: Substituted ethanes (I) are reacted with an alkyl metal reagent to form isomeric metalated olefins (IIIA and IIIB) having a trans (IIIB) to cis (IIIA) ratio of greater than 70:30.Type: GrantFiled: December 17, 1979Date of Patent: August 18, 1981Assignee: The Upjohn CompanyInventor: Jerry A. Walker
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Patent number: 4229470Abstract: Compounds are disclosed which have a juvenile hormone action on insects and also exhibit acaricide action. Said compounds are unsaturated aliphatic compounds having a trichloromethyl end group and the other end group of which is a phenol group which may be substituted and/or condensed, and which are capable of hindering the growth of insects from the larval to the adult stage and also exhibit an acaricide action on both adult acari and their eggs.Type: GrantFiled: January 17, 1979Date of Patent: October 21, 1980Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Angelo Longoni
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Patent number: 4219677Abstract: A process for the telomerization of dienes with a telomerizing compound containing a mobile hydrogen atom is disclosed wherein the reaction between the diene and the telomerizing agent is effected in the presence of a catalytic system comprising a water-soluble sulfonated triaryl phosphine compound, preferably a water-soluble salt of a mono-, di-, or trisulfonated triphenyl phosphine and a transition metal compound, preferably palladium or a palladium-containing compound. Water is added either before or after the reaction is completed and the reaction products can easily be separated from the aqueous catalyst solution.Type: GrantFiled: July 19, 1978Date of Patent: August 26, 1980Assignee: Rhone-Poulenc IndustriesInventor: Emile Kuntz
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Patent number: 4213920Abstract: A process for the production of benzaldehydes which are substituted in the ortho-position by an electrophilic group R, which comprises brominating an ortho-substituted compound of the formula I ##STR1## in which R represents the nitro group, the cyano group, an alkoxy group of 1 to 8 carbon atoms or a halogen atom, under irradiation with visible light in an inert solvent, to give the bromide of the formula II ##STR2## converting the resulting bromide by treatment with an alkali bromide in an inert solvent into a styrene compound of the formula III ##STR3## and ozonising this latter compound in an inert solvent to give the compound of the formula IV ##STR4##Type: GrantFiled: June 28, 1978Date of Patent: July 22, 1980Assignee: Ciba-Geigy CorporationInventor: Jacques Gosteli
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Patent number: 4207266Abstract: This invention relates to a novel process for the direct trifluoromethylation of aromatic compounds via carbon tetrachloride and hydrogen fluoride in the presence of strong Bronsted or Lewis acids which give an acidic reaction (increase in concentration of H.sub.2 F.sup.+ ions) in anhydrous hydrogen fluoride.Type: GrantFiled: March 9, 1979Date of Patent: June 10, 1980Assignee: Rohm and Haas CompanyInventor: Thomas R. Opie
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Patent number: 4199595Abstract: The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.Type: GrantFiled: March 20, 1978Date of Patent: April 22, 1980Assignee: American Cyanamid CompanyInventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4188346Abstract: A process for the dehydrohalogenation of a (polyhaloalkyl)benzene containing a benzylic halogen such as 1,3-dichloro-5-(2,4,4,4-tetrachlorobutyl)benzene by contacting the (polyhaloalkyl)benzene with a suitably active Lewis acid catalyst such as SbCl.sub.5 or TiCl.sub.4 under conditions sufficient to catalyze said dehydrohalogenation to form a (polyhaloalkenyl)benzene such as 3,5-dichloro-.alpha.-(2,2,2-trichloroethyl)styrene.Type: GrantFiled: May 18, 1978Date of Patent: February 12, 1980Assignee: The Dow Chemical CompanyInventor: Lowell D. Markley
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Patent number: 4178460Abstract: The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and .alpha.-cyano-m-phenoxybenzyl esters.Type: GrantFiled: March 20, 1978Date of Patent: December 11, 1979Assignee: American Cyanamid Co.Inventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4174349Abstract: Fluoroorganic compounds are prepared by reacting a haloorganic starting material in which at least one halo atom is replaceable with a fluorine atom by metathetical exchange, with calcium fluoride in the presence of a crown ether and an anhydrous, polar, basic organic solvent which complexes with the calcium ion and contains no --OH groups, at a temperature and for a period of time adequate to effect fluorination.Type: GrantFiled: October 30, 1978Date of Patent: November 13, 1979Assignee: Allied Chemical CorporationInventors: Francis E. Evans, Morris B. Berenbaum, Richard E. Eibeck, Martin A. Robinson
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Patent number: 4164583Abstract: The present invention provides benz[f]isoindolines, useful in the treatment of aggression, a process for their preparation and compositions containing these compounds.Type: GrantFiled: June 22, 1978Date of Patent: August 14, 1979Assignee: Sandoz Ltd.Inventors: Roland Achini, Wolfgang Oppolzer, Emil Pfenninger
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Patent number: 4163865Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.Type: GrantFiled: April 3, 1978Date of Patent: August 7, 1979Assignee: Bayer AktiengesellschaftInventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
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Patent number: 4158098Abstract: Polyalkoxy monovinyl substituted aromatic compounds, such as 3,4-dimethoxystyrene, function as both comonomer and randomizing agent in organolithium initiated copolymerization of a conjugated diene with a monovinyl aromatic compound, such as of butadiene with styrene. The resultant polymeric product exhibits lower levels of block styrene than does a corresponding copolymer made in the absence of the dimethoxystyrene.Type: GrantFiled: August 4, 1975Date of Patent: June 12, 1979Assignee: Phillips Petroleum CompanyInventor: William J. Trepka
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Patent number: 4154753Abstract: Surface-active products containing a highly fluorinated aliphatic substituent are prepared by nucleophilic attack of an oligomer of tetrafluoroethylene with an organic hydroxy compound in association with a proton acceptor.Type: GrantFiled: January 3, 1972Date of Patent: May 15, 1979Assignee: Imperial Chemical Industries LimitedInventor: Harold C. Fielding
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Patent number: 4145362Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.Type: GrantFiled: May 10, 1977Date of Patent: March 20, 1979Assignee: S.A. P R B en Neerlandais PRB N.V.Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
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Patent number: 4126623Abstract: There are disclosed ethers and thioethers having a benzyl or phenyl terminal group and another terminal group which is halogenated, and which ethers and thioethers exhibit juvenile hormone activity (i.e., function as inhibitors of the development of insects from their larval state to the adult state), as well as acaricide activity.Methods for preparing the ethers and thioethers are also disclosed.Type: GrantFiled: April 14, 1977Date of Patent: November 21, 1978Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Pietro Massardo, Angelo Longoni