Plural Chalcogens Bonded Directly To Ring Carbons Of The Five-membered Hetero Ring (e.g., Imides, Etc.) Patents (Class 548/513)
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Patent number: 4596826Abstract: Described herein are novel carboxylic acid amide compounds or carboximide compounds represented by the general formula: ##STR1## wherein Z represents a group of the formula (1) or (2): ##STR2## wherein R.sup.1 and R.sup.2 are hydrogen atom or methyl group, respectively; Xs, which may be the same or different, are hydrogen atom, a lower alkyl, lower alkoxy, halo, or alkyl halide group, respectively, and n represents an integer of 0 to 2, and their pharmaceutically acceptable salts; process for the production thereof; and medicines containing the same. The novel compounds are useful as treating, preventing and improving agents for diseases attended with cerebral dysfunction as well as various symptoms caused by the said diseases. Further, the compounds are useful for the improvement of neurosis of the stomach; and treatment and prevention for various constipation.Type: GrantFiled: June 12, 1984Date of Patent: June 24, 1986Assignee: Eisai Co., Ltd.Inventors: Yasuji Harigaya, Hiroo Ogura, Mitsuo Mihara, Motosuke Yamanaka, Kiyomi Yamatsu
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Patent number: 4595409Abstract: A compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a fluorine atom or a methyl group and R.sub.2 is a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.5 alkoxy group, a chloro(C.sub.2 -C.sub.4)alkoxy group, a dichloro(C.sub.2 -C.sub.4)alkoxy group, a cyclo(C.sub.3 -C.sub.7)alkoxy group, a phenoxy group, a C.sub.1 -C.sub.5 alkylthio group or a di(C.sub.1 -C.sub.5)alkylamino group, which is useful as a herbicide.Type: GrantFiled: August 8, 1984Date of Patent: June 17, 1986Assignee: Sumitomo Chemical Company, Ltd.Inventors: Toru Haga, Eiki Nagano, Ryo Yoshida, Shunichi Hashimoto
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Patent number: 4594099Abstract: New herbicidal N-substituted-.DELTA..sup.Type: GrantFiled: October 11, 1983Date of Patent: June 10, 1986Assignee: Nippon Kayaku Kabushiki KaishaInventors: Osamu Yamada, Mikio Yanagi, Fumio Futatsuya, Kenji Kobayashi
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Patent number: 4588786Abstract: A process for producing a water-soluble dicarboxylic acid imide compound which comprises adding a primary amine compound to an aqueous solution of a water-soluble salt of a dicarboxylic acid compound containing at least one dicarboxylic acid unit capable of forming a 5-membered cyclic acid imide linkage and heating the mixture to introduce an acid imide linkage into the molecule.Type: GrantFiled: October 5, 1984Date of Patent: May 13, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Hiromitsu Kadono, Tadao Natsuume
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Patent number: 4563535Abstract: A compound of the formula: ##STR1## wherein R is an isoproyl group or an n-amyloxycarbonylmethyl group, useful as a herbicide, is effectively produced by reacting a compound of the formula: ##STR2## wherein R is as defined above, with sulfuryl chloride or chlorine in a solvent in the presence of a dehydrohalogenating agent.Type: GrantFiled: September 12, 1984Date of Patent: January 7, 1986Assignee: Sumitomo Chemical Co., Ltd.Inventor: Ichiki Takemoto
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Patent number: 4537897Abstract: Novel 3-(1,2-propadienyl)-cyclopropane-carboxylates of the formula ##STR1## wherein R is alcohol used in pyrethrinoid synthesis, X and Y are both hydrogen or individually halogen or X is hydrogen or halogen and Y is alkyl of 1 to 18 carbon atoms or halogen or X is hydrogen or halogen or alkyl of 1 to 18 carbon atoms and Y is --COOR' or --CN or ##STR2## R' is alkyl of 1 to 18 carbon atoms, R.sub.2 and R.sub.3 are individually hydrogen or alkyl of 1 to 18 carbon atoms or R.sub.2 and R.sub.3 together with the nitrogen atom form a heterocycle having pesticidal properties.Type: GrantFiled: September 15, 1983Date of Patent: August 27, 1985Assignee: Roussel UclafInventors: Jean Tessier, Jean-Pierre Demoute, Joseph Cadiergue
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Patent number: 4536209Abstract: .DELTA.'-Tetrahydrophthalimides having a substituted oxy group at 3-position and, if necessary, a halogen atom at 4-position and/or at 2-position of phenyl group as N-substituent have excellent herbicidal activity and are useful as selective herbicides.Type: GrantFiled: October 5, 1981Date of Patent: August 20, 1985Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Tetsuo Jikihara, Masatsugu Oda, Bunji Natsume, Hisao Watanabe, Seiichi Suzuki
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Patent number: 4529599Abstract: Carboxylate esters of the formula (I):R.sub.1 --COOR.sub.2wherein R.sub.1 is a tricyclodecyl or tricycloundecyl group, and R.sub.2 is a group of the formula ##STR1## wherein R.sub.3 is hydrogen or a cyano group; ##STR2## wherein R.sub.3 is a hydrogen or a cyano group; ##STR3## which are useful as insecticides.Type: GrantFiled: December 9, 1983Date of Patent: July 16, 1985Assignee: Kao CorporationInventor: Shoji Nakagawa
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Patent number: 4528396Abstract: Novel cyclic di- and tetraester compounds made from the reaction of various unsaturated cyclic compounds with carboxylic acid anhydrides in the presence of oxygen are described. The process to make these novel ester compounds is preferably conducted at a temperature in the range from about 50.degree. to 150.degree. C. and in the presence of a catalyst. A transition metal borate catalyst is preferred. Such ester compounds are potentially useful plasticizers, lubricants, solvents and fuel additives.Type: GrantFiled: September 24, 1982Date of Patent: July 9, 1985Assignee: Texaco Inc.Inventors: John R. Sanderson, Lewis W. Watts, Jr.
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Patent number: 4518797Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO,--C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: May 21, 1985Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4489093Abstract: Novel esters in all possible isomeric forms of the formula ##STR1## wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkyl-alkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, ##STR2## aryl optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, ##STR3## R' is alkyl of 1 to 8 carbon atoms, R" and R"' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.sub.3 are individually alkyl of 1 to 18 carbon atoms (b) aryl of 6 to 14 carbon atoms optionally substituted with at least one substituent selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --OCF.sub.3, --CF.sub.3 and --SCF.sub.Type: GrantFiled: May 17, 1983Date of Patent: December 18, 1984Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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Patent number: 4484940Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.1 -C.sub.8 alkyl group except isopropyl, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: November 27, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4484941Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom and R is a C.sub.3 -C.sub.4 alkenyl group or a C.sub.3 -C.sub.4 alkynyl group, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: November 27, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4480118Abstract: This invention relates to a novel carboxylic acid ester represented by the following general formula (I) and an insecticidal and/or acaricidal composition containing the same as an active ingredient: ##STR1## wherein X is represented by the formula, ##STR2## and further also relates to a carboxylic acid or a reactive derivative thereof represented by the general formula, ##STR3## wherein R.sub.16 is hydroxy group, chlorine or bromine atom, or a C.sub.1-2 alkoxy group, W is oxygen atom or --CH.sub.2 -- group, k is an integer of 0 or 1, E is hydrogen, chlorine, fluorine or bromine atom, and n is an integer of 1 to 4.Type: GrantFiled: December 30, 1981Date of Patent: October 30, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Makoto Hatakoshi, Toshihiko Yano, Nobushige Itaya
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Patent number: 4474968Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.Type: GrantFiled: November 14, 1980Date of Patent: October 2, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4468521Abstract: Novel .gamma.-lactone derivatives are provided. These lactone derivatives, when reacted with hydrogen halide in alcohol, yield .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters. This ring-opening process is useful for the purpose of increasing the yield of pyrethrin analogs which are of value as insecticides and agricultural chemicals. Thus, the .gamma.-lactone derivatives by-produced in the production process for dihalogenovinyl chrysanthemumates are caused to undergo ring-opening reaction to yield the corresponding .gamma.-halogeno-.delta.-unsaturated carboxylic acid esters which are important intermediates for said pyrethrin analogs.Type: GrantFiled: February 22, 1982Date of Patent: August 28, 1984Assignee: Kuraray Co., Ltd.Inventors: Mori Fumio, Omura Toshiaki, Nishida Takashi, Itoi Kazuo
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Patent number: 4467100Abstract: Imide-amides having the structure ##STR1## wherein ##STR2## are certain cycloaliphatic or aromatic groups and R and R individually are hydrogen, halogen, an alkyl group having from 1 to 4 carbon atoms, hydroxy, carboxyl, and amine and when taken together represent ##STR3## wherein R.sup.2 is the same as R and R.sup.1, have been found to provide cured epoxy resin systems characterized by high temperature stability and excellent mechanical and physical properties.Type: GrantFiled: July 21, 1982Date of Patent: August 21, 1984Assignee: Lord CorporationInventors: Raj N. Gounder, John T. Geary
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Patent number: 4458084Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1981Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4458089Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1980Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4458083Abstract: Racemic mixtures and optically active isomers of (.alpha.S-5S)-.alpha.-amino-3-chloro-.alpha.-isoxazoline-5-acetic acid (AT-125). Provides process for preparing AT-125 and its analogs and intermediates used in the process.This case is a continuation of Ser. No. 906,175 filed May 15, 1978, now abandoned.Type: GrantFiled: November 14, 1980Date of Patent: July 3, 1984Assignee: The Upjohn CompanyInventor: Robert C. Kelly
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Patent number: 4439230Abstract: Oxime derivatives of the following formula are described: ##STR1## wherein R.sub.1 is hydrogen or halogen, and R.sub.8 is phthalimido, 4, 5, 6, 7-tetrahydrophthalimido or 3a, 4, 7, 7a-tetrahydrophthalimido attached at the nitrogen atom to the remainder of the molecule. These compounds are used for protecting plant crops from the action of aggressive agricultural chemicals.Type: GrantFiled: July 14, 1982Date of Patent: March 27, 1984Assignee: Ciba-Geigy CorporationInventors: Werner Fory, Henry Martin, Georg Pissiotas
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Patent number: 4439229Abstract: Compounds of the formula: ##STR1## wherein A is O or S, halo is chloro, bromo or fluoro; X' is --CH.sub.2 --, O or S; X is hydrogen or halo; R.sup.1 and R.sup.2 are the same or different radicals selected from hydrogen or lower alkyl; and Z can be a variety of substituents and agronomically acceptable salts, esters and amides as well as other heterocyclic benzenes are disclosed as selective herbicides.Type: GrantFiled: May 6, 1982Date of Patent: March 27, 1984Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4437879Abstract: Oxime derivatives of the formula (I) ##STR1## wherein n is 0, 1 or 2 and m is 0 or 1, andAr is a phenyl radical ##STR2## a naphthyl radical substituted by R.sub.2 and R.sub.3, a 5- to 10-membered heterocyclic radical which contains not more than 3 identical or different heteroatoms N, O and/or S and which is substituted by R.sub.2, R.sub.3 and R.sub.4 and can be substituted by oxo or thiono, or if m is O, Ar is a radical R--CO, wherein R is a radical --OR.sub.5, in which R.sub.5 is an aliphatic group containing not more than 8 carbon atoms or is an araliphatic group containing not more than 15 carbon atoms or is a cycloaliphatic or aromatic group, each containing not more than 10 carbon atoms, while the possible substituents of the aromatic radicals or of the cycloaliphatic radical are halogen, --CN, --NO.sub.2, lower alkyl, lower alkoxy, haloalkyl; or R is a radical --NH--CO--NH--R.sub.7 or a radical --N(R.sub.6)(R.sub.7), wherein R.sub.6 is hydrogen or lower alkyl and R.sub.Type: GrantFiled: July 14, 1982Date of Patent: March 20, 1984Assignee: Ciba-Geigy CorporationInventors: Werner Fory, Henry Martin, Georg Pissiotas
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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: 4431822Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.Type: GrantFiled: March 23, 1982Date of Patent: February 14, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiromichi Oshio, Katsuzo Kamoshita
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Patent number: 4423064Abstract: This invention relates to novel ester compounds derived from alkynoic acids and to their preparation. This invention is also directed to insecticidal and miticidal compositions comprising an acceptable carrier and an insecticidally or miticidally effective amount of a novel ester compound of this invention as well as a method of controlling pests by subjecting them to an insecticidally or miticidally effective amount of a novel ester compound of this invention.Type: GrantFiled: June 29, 1981Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4420327Abstract: .DELTA.'-Tetrahydrophthalimides having a substituted oxy group at 3-position and a halogen atom at 4-position if necessary, a halogen atom at 2-position of phenyl group as N-substituent have excellent herbicidal activity and are useful as selective herbicides.Type: GrantFiled: October 5, 1981Date of Patent: December 13, 1983Assignee: Mitsubishi Chemical Industries Ltd.Inventors: Tetsuo Jikihara, Masatsugu Oda, Kazuyuki Ushinohama, Hisao Watanabe, Seiichi Suzuki
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Patent number: 4411912Abstract: Esters and thiolesters of amino acids, intermediates therefor, synthesis thereof, and the use of said esters and thiolesters and compositions for the control of pests.Type: GrantFiled: November 13, 1979Date of Patent: October 25, 1983Assignee: Zoecon CorporationInventors: Clive A. Henrick, Barbara A. Garcia
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Patent number: 4409018Abstract: Novel compounds of the formula ##STR1## wherein R is a halogen, Q is hydrogen, a substituted or unsubstituted hydrocarbon, ##STR2## (wherein R.sub.1 is a substituted or unsubstituted hydrocarbon or ##STR3## R.sub.2 is hydrogen or a substituted or unsubstituted hydrocarbon, R.sub.3 is a substituted or unsubstituted hydrocarbon, R.sub.4 is a lower alkyl group, X is oxygen or an imino group which may be substituted by a lower alkyl, and each of Y and Z is oxygen or sulfur); which are useful as herbicides.Type: GrantFiled: May 28, 1981Date of Patent: October 11, 1983Assignee: Takeda Chemical Industries, Ltd.Inventor: Yasuo Ishida
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Patent number: 4375433Abstract: Disclosed is a process for preparing the antibiotic 6-hydroxymethyl-2-(.beta.-aminoethylthio)-1-carbadethiapen-2-em-3-carboxyl ic acid (I) ##STR1## and its pharmaceutically acceptable salt and ester derivatives. An intermediate for the production of these compounds are compounds of the formula ##STR2## wherein R.sup.5 and R are readily removable protecting groups.Type: GrantFiled: September 12, 1980Date of Patent: March 1, 1983Assignee: Merck & Co., Inc.Inventors: David G. Melillo, Kenneth M. Ryan
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Patent number: 4361576Abstract: Cyclobutanecarboxylic acid imides of the formula I ##STR1## wherein one of R.sub.1 and R.sub.6 is hydrogen, methyl or ethyl, and the other is methyl or ethyl, R.sub.2 and R.sub.3 independently of one another are each hydrogen, fluorine or methyl, or R.sub.2 is acetoxy or chlorine while R.sub.3 is hydrogen, and wherein R.sub.4 is hydrogen, methyl or chlorine, and R.sub.5 is hydrogen or methyl, whereby R.sub.3 and R.sub.4 together can also form an additional bond in the four-membered ring, are suitable for combating various fungi and have a particularly excellent action against Botrytis. They can be produced in an especially advantageous manner by photochemical [2+2] cycloaddition of alkenes or alkines with for example appropriately substituted maleic acid-(3,5-dichlorophenyl)-imides.Type: GrantFiled: October 29, 1980Date of Patent: November 30, 1982Assignee: Ciba-Geigy CorporationInventors: Niklaus Buhler, Marcus Baumann, Daniel Bellus, Elmar Sturm
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Patent number: 4339383Abstract: The invention relates to alkanolamido-.beta.-carboxylic acid esters of the formula I ##STR1## A full definition of the above formula will be found in claim 1 of the specification. These compounds are useful stabilizers for chlorinated thermoplastics.Type: GrantFiled: July 2, 1980Date of Patent: July 13, 1982Assignee: Ciba-Geigy CorporationInventors: Wolfgang Wehner, Klaus-Peter Michaelis, Rainer Schneider
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Patent number: 4332815Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.Type: GrantFiled: July 1, 1980Date of Patent: June 1, 1982Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4328237Abstract: Pyrethroid type insecticides are described having the formula: ##STR1## Compounds of general formula I are endowed with a high insecticide and acaricide activity.Type: GrantFiled: February 26, 1979Date of Patent: May 4, 1982Assignee: Montedison S.p.A.Inventors: Paolo Piccardi, Francesco Corda, Franco Gozzo, Augusto Menconi, Angelo Longoni
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Patent number: 4328167Abstract: A novel process for the preparation of optically active alcohols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, saturated and unsaturated, optionally substituted aliphatic, cycloaliphatic, aromatic and heterocyclic, with the proviso that at least one of R.sub.1 and R.sub.2 is other than hydrogen, and R.sub.1 and R.sub.2 taken together with the carbon atom to which they are attached form a hydrocarbon ring comprising reacting an ester of an optically active alcohol of the formula ##STR2## wherein A is the organic radical of a chiral carboxylic acid of the formula ##STR3## with a boron halide and reacting the resulting mixture with water to obtain the optically active isomer of the alcohol of formula I with the same configuration of the alcohol moiety of the starting ester in high yields without by-products of known processes.Type: GrantFiled: June 2, 1980Date of Patent: May 4, 1982Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre DeMoute