Halogen Containing Patents (Class 568/637)
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Patent number: 5098613Abstract: This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.Type: GrantFiled: July 11, 1990Date of Patent: March 24, 1992Assignee: Eli Lilly and CompanyInventors: Nancy G. Bollinger, Theodore Goodson, Jr., David K. Herron
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Patent number: 5093373Abstract: An ether compound represented by the following formula (I), it production and insecticidal compositions containing it as an active ingredient: ##STR1## wherein R.sub.1, represents a halogen atom or a methyl group; R.sub.2 represents a hydrogen atom or a fluorine atom; R.sub.3 represents a hydrogen atom, a halogen atom or a methyl group; R.sub.4 represents a (C.sub.1 -C.sub.3)alkyl group; Y represents an oxygen atom, a sulfur atom, a methylene group or --NH--; and Z represents a nitrogen atom or --CH.dbd..Type: GrantFiled: January 22, 1991Date of Patent: March 3, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
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Patent number: 5091416Abstract: Insecticidal and acaricidal compounds of formula: ##STR1## and stereoisomers thereof, where R.sup.1 represents C.sub.1-4 alkyl, R.sup.2 represents H, CN, CH.sub.3, or CF.sub.3 ; Q represents CH or N; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy and halophenoxy.Type: GrantFiled: September 28, 1989Date of Patent: February 25, 1992Assignee: Imperial Chemical Industries PLCInventor: Michael J. Bushell
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Patent number: 5082978Abstract: Mono-, di- and triphenols are selectively monomethylated by reaction with para-dimethoxybenzene in the presence of a catalytically effective amount of an acid catalyst.Type: GrantFiled: May 9, 1991Date of Patent: January 21, 1992Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Christian Allandrieu
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Patent number: 5081315Abstract: Compounds of the formula ##STR1## in which A represents the radicals ##STR2## in which R.sup.1 and R.sup.2 are different from one another and denote hydrogen, --NO.sub.2 or --NH.sub.2, R.sup.3 is hydrogen or halogen, X represents --NO.sub.2 or --NH.sub.2, with the proviso that R.sup.1 is hydrogen, if R.sup.2 is --NO.sub.2 or --NH.sub.2 and R.sup.2 is hydrogen, if R.sup.1 is --NO.sub.2 or --NH.sub.2.The compounds are prepared from 4,4'-bis[2-(4-hydroxyphenyl)hexafluoroisopropyl]diphenyl ether by nitration or reaction with nitrobenzenes followed by reduction of the nitro groups. They are used for the preparation of high-temperature-resistant polycondensates.Type: GrantFiled: August 20, 1990Date of Patent: January 14, 1992Assignee: Hoechst AktiengesellschaftInventors: Jurgen Lau, Gunter Siegemund
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Patent number: 5041687Abstract: This invention relates to the process for preparing partially brominated non-condensed ring polyaromatic product. The process comprises forming a reaction mass by adding a substantially stoichiometric amount of Br.sub.2 to a mixture comprising a non-condensed ring polyaromatic, a solvent selected from a group consisting of methylene dibromide, methylene dichloride and mixtures thereof, and a catalyst selected from the group consisting of zirconium halide, iron, ferric chloride and mixtures thereof, the reaction mass being maintained at a temperature within the range of from about 10.degree. to about 50.degree. C. during at least substantially all of the addition; refluxing the reaction mass after the addition is completed or at least nearly completed; and recovering from the reaction mass the partially brominated non-condensed ring polyaromatic product.Type: GrantFiled: May 26, 1988Date of Patent: August 20, 1991Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, David R. Brackenridge
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Patent number: 5026727Abstract: Insecticidal and acaricidal compounds of formula: ##STR1## and stereoisomers thereof, where R.sup.1 represents C.sub.1-4 alkyl, R.sup.2 represents H, CN, CH.sub.3, C.tbd.CH or CF.sub.3 ; Q represents CH or N; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy and halophenoxy.Type: GrantFiled: September 28, 1989Date of Patent: June 25, 1991Assignee: Imperial Chemical Industries PLCInventor: Michael J. Bushnell
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Patent number: 5012004Abstract: An insecticidal and/or acaricidal composition which comprises as an active ingredient an insecticidally and/or acaricidally effective amount of at least one ether compound of the formula: ##STR1## wherein X.sub.1 is a hydrogen atom, a halogen atom, a lower alkyl group, a halo(lower)alkyl group, a phenoxyphenoxy(lower)alkyl group, a lower alkoxy group, a halo(lower)alkoxy group, a phenyl group, a halo(lower)alkoxyphenyl group, a methylenedioxy group or a group of the formula: ##STR2## (in which ##STR3## is a 6-membered unsaturated ring, X.sub.2 is a hydrogen atom, a halogen atom or a halo(lower)alkoxy group, Y.sub.2 is a hydrogen atom or combined with Y.sub.1 to form a direct single bond, n is an integer of 1 or 2 and X is an oxygen atom, a sulfur atom, a carbonyl group or a group of the formula: --C(R.sub.3)(R.sub.4)-- (in which R.sub.3 and R.sub.4 are each a hydrogen atom or a lower alkyl group));Y.sub.1 is a hydrogen atom or combined with Y.sub.2 to form a direct single bond;R.sub.1 and R.sub.Type: GrantFiled: November 2, 1988Date of Patent: April 30, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Junya Takahashi, Sumio Nishida, Izumi Fujimoto, Yoshinori Shono, Hiroaki Fujimoto
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Patent number: 4997989Abstract: Novel tert-butylalkynols of the formula (I) ##STR1## where Y is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, aryl, aryloxy or benzyl and m is an integer from 1 to 3, and the individual groups Y may be identical or different when m>1, and a process for their preparation are described.Type: GrantFiled: January 4, 1989Date of Patent: March 5, 1991Assignee: BASF AktiengesellschaftInventors: Hubert Smuda, Wolfgang Rohr
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Patent number: 4992593Abstract: A compound of the formula ##STR1## in which independently of one another R is equal to OH or lower alkyl having 1 to 4 carbon atoms, R' is equal to hydrogen or lower alkyl having 1 to 4 carbon atoms, processes for their preparation and their use as starting material in the preparation of partially fluorinated polycondensates.Type: GrantFiled: November 23, 1988Date of Patent: February 12, 1991Assignee: Hoechst AktiengesellschaftInventor: Gunter Siegemund
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Patent number: 4990677Abstract: Fungicidal and plant growth-regulating azolylmethylcyclopropyl derivatives of the formula ##STR1## in which R represents halogen, alkyl or optionally substituted phenyhl, or represents the groupings --Y--R.sup.2,whereinY represents oxygen, sulphur, SO or SO.sub.2 andR.sup.2 represents optionally substituted phenyl,R.sup.1 represents hydrogen, alkyl or acyl,X represents nitrogen or a CH group,Z represents halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxy with 1 or 2 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio with 1 or 2 carbon atoms and 1 to 5 halogen atoms or phenyl which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen, or represents phenoxy which is optionally substituted by alkyl with 1 or 2 carbon atoms and/or halogen andm represents the number 0, 1, 2 or 3, and addition products thereof with acids and metal salts.Type: GrantFiled: February 12, 1990Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Klaus Stroech, Wilhelm Brandes, Stefan Dutzmann
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Patent number: 4973736Abstract: Diethers of m- or p-hydroxyphenol, as well as the monoethers, are prepared by reacting m- or p-tert.-butoxyphenol of the formula II ##STR1## with a halogen compound in the presence of a hydroxide, carbonate and/or bicarbonate of an alkali metal or alkaline earth metal and an organic solvent which is inert under the reaction conditions, at from 20.degree. C. to 150.degree. C., and, if desired, reacting the resulting diether with a dilute aqueous inorganic acid at from 30.degree. to 100.degree. C. to give the monoether.The end products which can be prepared by the process according to the invention are useful starting materials for the preparation of dyes, drugs and crop protection agents.Type: GrantFiled: August 15, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Werner Hoffmann, Heinz-Guenter Oeser, Wolfgang Rohr, Juergen Varwig
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Patent number: 4954659Abstract: A grignard synthesis of pharmacologically active 1,4-bis(dihydroxyphenyl)butane and analogs, as well as novel intermediates, is provided, comprising preparing a grignard reagent preferably, a 3,4-dialkoxyphenyl propyl magnesium bromide, which may be reacted with carbonyl compounds to form intermediates of desired end products, said carbonyl compounds preferably being 3,4-dialkoxybenzaldehydes. The resulting alcohol is converted to a corresponding ether or siloxy compound, at the carbonyl site. The oxy-substituent is cleaved off; and the benzene ring or rings dealkylated to leave hydroxy substituents on the rings.Type: GrantFiled: August 19, 1988Date of Patent: September 4, 1990Assignee: Chemex Pharmaceuticals, Inc.Inventors: Robert M. Parkhurst, Ronald S. Pardini
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Patent number: 4939305Abstract: Cured resins of high fracture toughness are prepared from N,N'-bisimides of formula I ##STR1## and alkenyl compounds of formula IID(G).sub.m IIin which D is an m-valent group and G represents a phenyl ring having at least one alkenyl (e.g. allyl or 1-propenyl) substituent.Type: GrantFiled: November 30, 1988Date of Patent: July 3, 1990Assignee: Technochemie GmbHInventors: Horst Stenzenberger, Peter Koenig
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Patent number: 4929765Abstract: Phenylacetaldehydes of the general formula I ##STR1## where R.sup.1 to R.sup.5 are each independently of the others hydrogen, alkyl, alkoxy, halogen, haloalkyl, haloalkoxy or haloalkylthio, by catalytic rearrangement in the presence of a zeolite, are prepared by reacting an epoxy of the formula II or a phenylglycol of the formula III ##STR2## where Y and Z can be identical to or different from each other and are each hydroxyl, alkoxy, aryloxy or acyloxy, in the gas phase over a borosilicate zeolite catalyst at from 70.degree. to 200.degree. C. under reduced pressure.Type: GrantFiled: November 22, 1988Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Hubert Smuda, Wolfgang Hoelderich, Norbert Goetz, Hans-Gert Recker
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Patent number: 4914244Abstract: Difluorochloromethoxybenzenes are prepared by reacting phenols with trichloromethyl chloroformate (=di-phosgene) in the presence of hydrogen fluoride.Type: GrantFiled: January 14, 1987Date of Patent: April 3, 1990Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 4900758Abstract: Novel insecticides have the formula ##STR1## in which R.sub.1 is hydrogen, fluoro or trifluoromethyl;R.sub.2 is(a) halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 haloalkoxy if R.sub.1 is hydrogen or fluoro; or(b) hydrogen if R.sub.1 is trifluoromethyl;R.sub.3 is hydrogen or halogen; andR.sub.4 is hydrogen or mono- or poly-halogen.Type: GrantFiled: May 11, 1989Date of Patent: February 13, 1990Assignee: ICI Americas Inc.Inventor: Karl J. Fisher
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Patent number: 4879292Abstract: A nitrogen-containing heterocyclic compound of the formula: ##STR1## wherein R.sub.1 is either one of the following groups: ##STR2## (in which R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.14, R.sub.15, R.sub.16 and R.sub.17 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylthio group, a trifluoromethyl group or a nitro group, R.sub.18, R.sub.19, R.sub.20 and R.sub.21 are, the same or different, each a hydrogen atom or a methyl group, k is an integer of 0 to 1 and l is an integer of 0 to 3);R.sub.2 and R.sub.3 are, the same or differnt, each a hydrogen atom, a halogen atom or a methyl group;R.sub.4 is a halogen atom or a methyl group;R.sub.5 and R.sub.6 are, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 haloalkyl group or a C.sub.1 -C.sub.Type: GrantFiled: March 22, 1988Date of Patent: November 7, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Sumio Nishida, Noritada Matsuo, Makoto Hatakoshi, Hirosi Kisida
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Patent number: 4873371Abstract: A method is provided for making certain hydroxy-terminated arylene ethers useful as spacers in liquid crystalline polyesters. There is initially formed a dicarbonyl adduct from a dihydroxyaromatic compound, such as hydroquinone and a haloarylcarbonyl compound. The adduct formed is oxidized to the corresponding diester. Hydrolysis of the diester provides the hydroxy-terminated arylene ether.Type: GrantFiled: August 1, 1988Date of Patent: October 10, 1989Assignee: General Electric CompanyInventors: Gary W. Yeager, David N. Schissel
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Patent number: 4873373Abstract: Disclosed is a process for preparing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl ethers represented by the following formula (I): ##STR1## wherein R stands for a lower alkyl group, and X.sub.1 and X.sub.2 stand for a hydrogen atom or fluorine atom,which comprises subjecting a 3-phenoxybenzyl 2-(4-alkoxy-3-halogenophenyl)-2-methylpropyl ether or 3-phenoxybenzyl-2-(4-alkoxy-3,5-dihalogenophenyl)-2-methylpropyl ether represented by the following formula (II): ##STR2## wherein R stands for a lower alkyl group, X.sub.1 and X.sub.2 stand for a hydrogen atom or fluorine atom, and Y.sub.1 and Y.sub.2 stand for a hydrogen atom, chlorine atom, bromine atom or iodine atom, with the proviso that at least one of Y.sub.1 and Y.sub.Type: GrantFiled: July 16, 1986Date of Patent: October 10, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Mitsumasa Umemoto, Tamotsu Asano, Hironobu Horie, Akinobu Takagi, Nobuyasu Tamura, Takeshi Nishida
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Patent number: 4840971Abstract: An ether compound represented by the following general formula (I), its produciton method and an insecticidal and/or acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be identical or different, represent a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl, lower haloalkoxyl, lower alkenyl or lower alkenyloxyl group, or represent, taken together, methylenedioxy, lower alkylene, ethyleneoxy or lower alkylethyleneoxy group; R.sub.3 represents a hydrogen or fluorine atom; R.sub.4 represents a hydrogen or halogen atom or a lower alkyl, lower haloalkyl, lower alkoxyl or lower haloalkoxyl group; m represents an integer of 1 or 2; Y represents an oxygen or sulfur atom or a group represented by the formula --CH.sub.2 -- or --NH--; and Z represents a nitrogen atom or a group represented by the formula --CH.dbd., and its starting materials.Type: GrantFiled: April 2, 1987Date of Patent: June 20, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
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Patent number: 4816596Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.Type: GrantFiled: March 28, 1986Date of Patent: March 28, 1989Assignee: Rhone-Polenc Specialites ChimouesInventor: Bernard Langlois
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Patent number: 4814340Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.Type: GrantFiled: November 6, 1986Date of Patent: March 21, 1989Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Nakatani Kiyoshi, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
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Patent number: 4812483Abstract: A compound of formula:CXY.dbd.CH--CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 Rwherein X and Y are each selected from hydrogen and halogen, R.sup.1 and R.sup.2 are each lower alkyl of up to four carbon atoms, or together with the adjacent carbon atom form a cycloalkyl group of up to six carbon atoms, and R represents a phenoxy- or benzyl-substituted phenyl group which may optionally be substituted with fluorine. The compounds are useful for combating insect pests.Type: GrantFiled: December 9, 1986Date of Patent: March 14, 1989Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4808762Abstract: Compounds of the formula ##STR1## in which Ar is substituted or unsubstituted phenyl, naphthyl, or thienyl; Z is oxygen, sulfur, or methylene; and Ar' is 2-methyl[1,1'-biphenyl]-3-yl, 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, or 6-phenoxy-2-pyridyl exhibit pyrethroid-like insecticidal and acaricidal activity and are relatively harmless to aquatic fauna.Type: GrantFiled: September 9, 1987Date of Patent: February 28, 1989Assignee: FMC CorporationInventors: Gary A. Meier, Scott M. Sieburth, Thomas G. Cullen, John F. Engel
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Patent number: 4798912Abstract: Novel substituted phenoxybenzyldihalodimethyl-cyclopropylmethyl ethers of the formula ##STR1## in which X.sub.1 and X.sub.2 each independently of the other represents fluorine, chlorine or bromine;R.sub.1 represents hydrogen or flourine; andR.sub.2 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy, and, if X.sub.1 and X.sub.2 have different meanings, the optical isomers of the compound of the formula I; processes for the manufacture of those compounds, and compositions containing them for use in pest control, especially for the control of insects, especially the larval stages thereof, that attack plants and animals, and of phytopathogenic fungi. The novel compounds exhibit good activity especially against insects that damage plants in rice crops.Type: GrantFiled: November 9, 1987Date of Patent: January 17, 1989Assignee: Ciba-Geigy CorporationInventors: Laurenz Gsell, Peter Ackermann
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Patent number: 4792563Abstract: Insecticidally active compounds of the formula (I): ##STR1## wherein R.sup.4 represents a group selected from those groups represented by R.sup.5 in insecticidally active compounds of formula: ##STR2## R.sup.3 is selected from fluoromethyl and difluoromethyl, and either (a) R.sup.1 and R.sup.2 represent alkyl of one, two, three or four carbon atoms, or (b) R.sup.1 and R.sup.2 taken together with the adjacent carbon atom form a cycloalkyl ring of four, five or six carbon atoms.Type: GrantFiled: October 6, 1987Date of Patent: December 20, 1988Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4791139Abstract: A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.Type: GrantFiled: February 25, 1987Date of Patent: December 13, 1988Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4788348Abstract: Compounds of formula R.sup.3 --CH.dbd.CH--CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 R.sup.4 wherein R.sup.1 and R.sup.2 are H, alkyl or together form a cycloalkyl group with the adjacent carbon, R.sup.3 is a substituted phenyl group, R.sup.4 is an optionally substituted phenoxy phenyl group, and compositions containing them useful as insecticides, and compounds of formula HOCH.sub.2 --CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 R.sup.4 and OCH--CR.sup.1 R.sup.2 CH.sub.2 OCH.sub.2 R.sup.4, useful as intermediates therefor.Type: GrantFiled: August 12, 1987Date of Patent: November 29, 1988Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4786654Abstract: There are disclosed novel unsubstituted or substituted phenoxyfluorobenzyltetramethylcyclopropylmethyl ethers of formula ##STR1## wherein Y is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkoxy which is substituted by 1 to 9 halogen atoms, C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylthio which is substituted by 1 to 9 halogen atoms, or is C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl and their benzyl ether intermediates of formula IV ##STR2## wherein X is halogen or p-tosyl. Also disclosed is a process for the preparation of these compounds and compositions containing them for use in pest control, especially for controlling insects that attack plants and animals, in particular their larval stages. The novel compounds are particularly effective against plant-destructive insects in rice crops.Type: GrantFiled: May 26, 1987Date of Patent: November 22, 1988Assignee: Ciba-Geigy CorporationInventors: Laurenz Gsell, Peter Ackermann
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Patent number: 4782094Abstract: A difluorobromomethyoxyphenyl derivative of the general formula ##STR1## wherein A represents an oxygen atom or a methylene group, and Y represents a hydrogen or fluorine atom. A miticide comprising the above derivative as an active ingredient is also provided.Type: GrantFiled: March 11, 1987Date of Patent: November 1, 1988Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Satoshi Numata, Kouji Kitajima, Kenji Kodaka, Yukiharu Fukushi, Shiroh Shiraishi, Masahiko Nakamura, Masayuki Ooka
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Patent number: 4777185Abstract: Pesticidal compounds of formula IR.sub.A CR.sub.3 .dbd.CR.sub.4 CHDR.sub.B Iin which formula:R.sub.A represents a group ArCR.sub.1 R.sub.2 --in which Ar represents a phenyl or naphthyl group optionally substituted by one or more halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl or haloalkyl groups;R.sub.1 and R.sub.2 together with the carbon to which they are attached represent a C.sub.3 -C.sub.6 cycloalkyl group optionally substituted by one or more halogen atoms or C.sub.1 -C.sub.6 alkyl groups.R.sub.3 and R.sub.4 which may be identical or differ, represent hydrogen halogen or C.sub.1 -C.sub.6 alkyl groups andR.sub.B represents the residue of an alcohol R.sub.B CHDOH in which D is hydrogen or cyano and of which the [1R, cis]2,2-dimethyl-3-(2,2-dibromovinyl) cyclopropane carboxylic ester is significantly insecticidal,the configuration of R.sub.A and CHDR.sub.Type: GrantFiled: April 5, 1985Date of Patent: October 11, 1988Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. Singh Khambay, Ahmet Baydar
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Patent number: 4751329Abstract: Novel intermediates useful in the preparation of fluorophenoxyphenoxypropionates and derivatives thereof which possess herbicidal activity selectively in the presence of broadleaf crops.Type: GrantFiled: May 9, 1986Date of Patent: June 14, 1988Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4744812Abstract: Substituted diphenyl ethers of the formula ##STR1## where Z.sub.1, Z.sub.2 and Z.sub.3 are hydrogen, halogen, nitro, cyano, carboxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylmercapto, haloalkylmercapto, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl or haloalkylsulfonyl, Z.sub.4 is hydrogen, cyano, alkyl, alkoxy, acetoxy or alkylmercapto, Y is hydrogen, halogen, cyano or nitro, X is oxygen, sulfur, sulfinyl or sulfonyl, and A is hydrogen, unsubstituted or substituted alkyl ##STR2## and can also be sulfonyl ##STR3## when X is oxygen, and, when Z.sub.4 is alkoxy or alkylmercapto, can also be a methylene chain --(CH.sub.2).sub.m -- by which the radicals Z.sub.4 --CH--X-- are bonded to form a ring, R.sub.1 is hydrogen, methyl, ethyl or n-propyl, R.sub.2 is cyano, methoxy, ethoxy or ##STR4## where B is OH, ONa, O--alkyl, unsubstituted or substituted phenoxy, --NH.sub.2, --NH--alkyl or --N(alkyl).sub.2, n is 1, 2 or 3, R.sub.3 and R.sub.Type: GrantFiled: March 4, 1985Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Bruno Wuerzer, Gerhard Hamprecht
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Patent number: 4743622Abstract: The invention relates to new aromatic alkane derivatives of the general formula ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 alkyl, halo-C.sub.1-4 alkyl, phenyl-C.sub.1-4 alkyl, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, halo-C.sub.2-4 alkynyl, phenyl-C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, halo-C.sub.1-4 alkoxy, phenyl-C.sub.1-4 alkoxy, C.sub.2-4 alkenyloxy, halo-C.sub.2-4 alkenyloxy, phenyl-C.sub.2-4 alkenyloxy, C.sub.2-4 alkynyloxy, halo-C.sub.2-4 alkynyloxy, phenyl-C.sub.2-4 alkynyloxy, alkylsulphonyloxy, haloalkylsulphonyloxy, arylsulphonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or these groups substituted by one or more of C.sub.1-6 alkyl, halo-C.sub.1-6 alkyl, phenyl-C.sub.1-6 alkyl, C.sub.1-6 alkyl interrupted by an O-, N- or S- atom, C.sub.2-4 alkenyl, halo-C.sub.2-4 alkenyl, phenyl-C.Type: GrantFiled: February 11, 1986Date of Patent: May 10, 1988Assignee: Schering AktiengesellschaftInventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
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Patent number: 4743703Abstract: The 4-fluoroalkyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: September 19, 1983Date of Patent: May 10, 1988Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4740629Abstract: A process for partially brominating non-condensing ring aromatics (e.g. diphenyl ether) in the absence of a solvent by adding the polyaromatic to a stoichiometric excess of liquid bromine containing a zirconium halide catalyst. Product containing three bromine atoms per benzene ring (e.g., hexabromodiphenyl ether) is formed in high selectivity by keeping the reaction mixture below a threshold temperature at which higher bromine substitution occurs.Type: GrantFiled: July 6, 1987Date of Patent: April 26, 1988Assignee: Ethyl CorporationInventors: David R. Brackenridge, Bonnie G. McKinnie
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Patent number: 4717776Abstract: A process for partially brominating polyphenylene ether (e.g. diphenly ether) in the absence of a solvent by adding the polyphenylene ether to a stoichiometric excess of liquid bromine containing a zirconium halide catalyst.Type: GrantFiled: April 21, 1986Date of Patent: January 5, 1988Assignee: Ethyl CorporationInventors: David R. Brackenridge, Bonnie G. McKinnie
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Patent number: 4715882Abstract: The invention relates to certain substituted phenoxypropionaldehyde derivatives, formulations of said derivatives and the use thereof for preemergence or postemergence control of noxious plants, i.e., weeds.Type: GrantFiled: October 15, 1986Date of Patent: December 29, 1987Assignee: PPG Industries, Inc.Inventor: Muppala S. Raju
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Patent number: 4716251Abstract: Diaryloxyalkanes such as diphenoxyethane are brominated to give a product containing an average of about 5-7 bromine atoms per molecule by commingling a solution of the diaryloxyalkane in a haloalkane solvent with an excess of liquid bromine in the absence of a bromination catalyst.Type: GrantFiled: February 7, 1986Date of Patent: December 29, 1987Assignee: Ethyl CorporationInventors: Gerald L. Scymanski, Amgad S. Mossaad, Saadat Hussain
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Patent number: 4705900Abstract: Compounds of formula R.sup.3 --CH.dbd.CH--CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 R.sup.4 wherein R.sup.1 and R.sup.2 are H, alkyl or together form a cycloalkyl group with the adjacent carbon, R.sup.3 is a substituted phenyl group, R.sup.4 is an optionally subsituted phenoxy phenyl group, and compositions containing them useful as insecticides, and compounds of formula HOCH.sub.2 --CR.sup.1 R.sup.2 --CH.sub.2 OCH.sub.2 R.sup.4 and OCH--CR.sup.1 R.sup.2 CH.sub.2 OCH.sub.2 R.sup.4, useful as intermediates therefor.Type: GrantFiled: September 3, 1986Date of Patent: November 10, 1987Assignee: Imperial Chemical Industries PLCInventor: Alan J. Whittle
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Patent number: 4701563Abstract: Difluorocyclopropane derivatives of the general formula I ##STR1## in which R.sub.1 is halogen, C.sub.1-4 -alkoxy, fluoro-substituted alkoxy, C.sub.1-4 -alkyl or trifluoromethyl,R.sub.2 is hydrogen or fluorine andn is 0, 1 or 2,are described, which have valuable insecticidal and acaricidal properties.Type: GrantFiled: March 20, 1986Date of Patent: October 20, 1987Assignee: Schering AktiengesellschaftInventors: Heinrich Franke, Hartmut Joppien, Helga Franke
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Patent number: 4701542Abstract: A process for the resolution of hemiacetal compounds of the formula ##STR1## wherein A is a hydrocarbon chain containing 1 to 16 groups, the said chain optionally containing at least one heteroatom, at least one unsaturation, the assembly of the group constituting the chain may be a mono- or polycyclic system including a spiro or endosystem and the assembly of chain A and the carbon atoms attached thereto can contain at least one chiral atom or the hemiacetal moiety thereto which can present a chirality due to the dissymetric spatial configuration of the molecule and Y is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms optionally substituted, --CY.sub.3 ' and the .beta.,.gamma.Type: GrantFiled: March 31, 1986Date of Patent: October 20, 1987Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute
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Patent number: 4695655Abstract: Ethynylphenyl derivatives of diphenylhexafluoropropane having the formula: ##STR1## where X is oxygen or sulfur and each of R, R.sub.1, or R.sub.2 is hydrogen or ethynyl. The compounds are useful in forming polymer structures, either homopolymers or copolymers.Type: GrantFiled: September 4, 1984Date of Patent: September 22, 1987Assignee: Hughes Aircraft CompanyInventors: Kreisler S. Y. Lau, William J. Kelleghan
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Patent number: 4686235Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophlic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: August 12, 1985Date of Patent: August 11, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Norman P. Jensen, Milton L. Hammond, Robert A. Zambias, John McDonald, Kathleen M. Rupprecht
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Ether compound, and an insecticidal and acaricidal composition containing it as an active ingredient
Patent number: 4664698Abstract: An ether compound represented by the following general formula (I), its production method and an insecticidal and acaricidal composition containing as an active ingredient: ##STR1## wherein X represents an oxygen atom or a group represented by the formula --NH--; when X represents an oxygen atom, Z represents a nitrogen atom or a group represented by the formula --CH.dbd.; when X represents --NH--, Z represents --CH.dbd.; when X represents an oxygen atom and Z represents a nitrogen atom, or when X represents --NH--, R.sub.1 represents a hydrogen or fluorine atom; when X represents an oxygen atom and Z represents --CH.dbd., R.sub.1 represents a fluorine atom; Y.sub.1 and Y.sub.2, which may be identical or different, represent a hydrogen or halogen atom or an alkyl, haloalkyl, alkoxyl or haloalkoxyl group; m and n represent an integer of 1 to 4 and the sum of them is not more than 5; R.sub.2 represents a methyl group or a chlorine atom; and R.sub.3 represents a methyl group, a halogen atom or a methoxy group.Type: GrantFiled: September 9, 1985Date of Patent: May 12, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano -
Patent number: 4661501Abstract: The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphthyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group and R.sup.3, stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to the uses of these compounds.These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.Type: GrantFiled: February 26, 1986Date of Patent: April 28, 1987Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Kiyoshi Nakatani, Satoshi Numata, Kenji Kodaka, Kengo Oda, Shiro Shiraishi, Takatoshi Udagawa
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Patent number: 4611004Abstract: 3-Phenoxybenzyl-(2-phenyl-2,2-alkylene-ethyl) ethers and -thioethers of the formula ##STR1## wherein A is oxygen or sulfur,R.sub.1 is hydrogen, methyl, cyano or ethinyl,R.sub.2 and R.sub.3 are hydrogen, halogen or C.sub.1 -C.sub.5 -alkyl,n is 2 to 4,X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.1 -C.sub.5 -alkoxy or C.sub.1 -C.sub.5 -haloalkoxy,X.sub.2 is hydrogen, halogen or C.sub.1 -C.sub.5 -alkyl, or together with X.sub.1 in the adjacent position is methylenedioxy, andX.sub.3 and X.sub.4 are each hydrogen or halogen.A process for producing these compounds and their use for controlling pests are described.Type: GrantFiled: March 27, 1985Date of Patent: September 9, 1986Assignee: Ciba-Geigy CorporationInventors: Peter Ackermann, Laurenz Gsell
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Patent number: 4599362Abstract: The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R.sup.1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R.sup.2 stands for a hydrogen atom, or a methyl or ethyl group, R.sup.3 stands for a halogen atom, or a methyl or methoxyl group, R.sup.4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R.sup.4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or 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: November 18, 1983Date of Patent: July 8, 1986Assignee: Mitsuitoatsu Chemicals, Inc.Inventors: Kiyoshi Nakatani, Satoshi Numata, Tsuneo Inoue, Akira Hosono, Kengo Oda, Yutaka Kubota, Hajime Tachibana, Takatoshi Udagawa, Masatoshi Gohbara
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Patent number: RE32606Abstract: There is disclosed a process for the preparation of completely brominated derivatives of aromatic compounds comprising one or more phenyl groups which may contain substituents, side chains or be partially-brominated. The complete bromination is effected by utilizing liquid bromine as a reaction solvent whereby the starting aromatic material is reacted with an excess of bromine which contains a bromination catalyst and the mixture is refluxed for a sufficient time. Use of these brominated derivatives as fire retarding agents is nylon and polyester is also disclosed.Type: GrantFiled: April 29, 1986Date of Patent: February 16, 1988Assignee: Great Lakes Chemical CorporationInventor: Heinrich Stepniczka