Patents by Inventor Kazunori Tsushima
Kazunori Tsushima has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5550258Abstract: The present invention provides an ester compound represented by a formula I: ##STR1## wherein R.sub.1 denotes a hydrogen atom or a methyl group; R.sub.2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group, or a C.sub.1 -C.sub.1 6 alkyl group which may be substituted with at least one halogen atom; and R.sub.3 represents an acid residue of pyrethroids.The invention also relates to an active agent for controlling noxious insect pests containing the ester compound as an active ingredient, an intermediate for production of the ester compound and a process for producing the intermediate. The ester compound represented by the formula I has good activities for controlling noxious insect pests.Type: GrantFiled: August 23, 1994Date of Patent: August 27, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
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Patent number: 5550260Abstract: A process for the production of a cyclopentenol compound represented by the formula I: ##STR1## wherein R.sub.1 represents a 2-propenyl group or a 2-propynyl group from a cyclopentenolone compound represented by the formula II: ##STR2## by protecting the hydroxyl group of the compound II, reacting the protected compound II with a reagent system obtained from TiCl.sub.4, Zn and CH.sub.2 Br.sub.2 or CH.sub.2 I.sub.2 and removing the protecting group from the resulting reaction product.Type: GrantFiled: June 2, 1994Date of Patent: August 27, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Tomonori Iwasaki, Masaya Suzuki, Noritada Matsuo
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Patent number: 5530015Abstract: There is disclosed a dihalopropene compound of the formula I: ##STR1## wherein l is an integer of 1 to 5; m is an integer of 1 to 4; R.sup.1 's and R.sup.2 's are the same or different and are independently halogen or various other groups; D is oxygen; X's are the same or different and are independently chlorine or bromine; Y is oxygen; Z, P and Q are the same or different and are independently nitrogen or CH, provided that P and Q are not simultaneously nitrogen, and when Y is sulfur, Z is CH. Also disclosed is an insecticide/acaricide comprising the dihalopropene compound as an active ingredient. The dihalopropene compound exhibits excellent insecticidal/acaricidal action. Further disclosed is an intermediate compound for use in the production of the dihalopropene compound.Type: GrantFiled: October 19, 1994Date of Patent: June 25, 1996Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyasu Sakamoto, Masaya Suzuki, Toshio Nagatomi, Kazunori Tsushima, Kimitoshi Umeda
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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: 5019595Abstract: This invention relates to a novel carboxylic acid esters represented by the formula (I) below and insecticides containing them as an active ingredient, ##STR1## wherein R represents a C.sub.1-5 alkyl group, a C.sub.3-6 cycloalkyl group, a C.sub.3-6 alkenyl group, a C.sub.3-6 alkynyl group or a C.sub.1-5 haloalkyl group.Type: GrantFiled: September 20, 1990Date of Patent: May 28, 1991Assignee: Sumitomo Chemical Company, Ltd.Inventors: Toshihiko Yano, Yoko Torisu, Hiroko Sekihachi, Noritada Matsuo, Tohei Takagaki, Kazunori Tsushima
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Patent number: 5006538Abstract: 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: October 31, 1988Date of Patent: April 9, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
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Patent number: 5004753Abstract: This invention relates to novel carboxylic acid esters represented by the formula (I) below, methods for their production and insecticides containing them as an active ingredient, and an alcohol compound useful as an intermediate for manufacturing carboxylic acid esters represented by the formula (I), ##STR1## wherein R.sup.1 represents a halogenated lower alkyl group, R.sup.2 represents a fluorine atom or a methyl group, R.sup.3 represents a hydrogen atom or a methyl group, R.sup.4 represents a hydrogen atom or a methyl group, and when R.sup.4 is a hydrogen atom, R.sup.5 represents a group of the formula, ##STR2## in which X and Y are the same or different and represent a hydrogen atom, a methyl group, a halogen atom or a halogenated lower alkyl group, and when R.sup.4 is a methyl group, R.sup.5 represents a methyl group.Type: GrantFiled: April 20, 1990Date of Patent: April 2, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Ken Otaka, Noritada Matsuo, Kazunori Tsushima, Toshihiko Yano
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Patent number: 4985457Abstract: This invention relates to novel carboxylic acid esters represented by the formula (I) below, methods for their production and insecticides and/or acaricides containing them as an active ingredient, ##STR1## wherein R.sup.1 represents a C.sub.1-5 alkyl group, a C.sub.2-4 alkenyl group or a C.sub.2-4 alkynyl group; R.sup.2 represents a fluorine atom or a methyl group; and R.sup.3 represents a hydrogen atom or a methyl group.Type: GrantFiled: May 31, 1989Date of Patent: January 15, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroko Kishino, Noritada Matsuo, Tohei Takagaki, Kazunori Tsushima, Toshihiko Yano, Yoko Torisu
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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: 4837242Abstract: Heterocyclic derivatives represented by the following formula have excellent preventive, curative and systemic controlliing effects on various plant microbes. ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group, A represents ##STR2## wherein R.sup.2 represents a methyl group, an ethyl group or a trifluoromethyl group, Y.sup.1 represents an amino group, a methyl group or a chlorine atom, R.sup.3 represents a methyl group or a trifluoromethyl group and Z represents a hydrogen atom, a halogen atom or a methyl group and when A represents the formula: ##STR3## X represents an oxygen atom or sulfur atom and when A represents the formula: ##STR4## X represents a sulfur atom.Type: GrantFiled: December 30, 1987Date of Patent: June 6, 1989Assignee: Sumitomo Chemical Company, LimitedInventors: Tadashi Ohsumi, Kazunori Tsushima, Sumio Nishida, Kiyoto Maeda, Tadashi Ooishi, Noritada Matsuo
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Patent number: 4774369Abstract: This invention relates to novel carboxylic acid esters represented by the formula (I) below, methods for production thereof and insecticides containing them as the active ingredient, and an alcohol compound useful as an intermediate for manufacturing carboxylic acid esters represented by the formula (I). ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; when R.sub.1 is a hydrogen atom, R.sub.2 represents a group of the formula ##STR2## in which X and Y are the same or different and represent a hydrogen atom, a methyl group, a halogen atom or a halogenated lower alkyl group, and when R.sub.1 is a methyl group, R.sub.2 represents a methyl group; R.sub.3 represents hydrogen atom or a methyl group; and R.sub.4 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group.Type: GrantFiled: September 14, 1987Date of Patent: September 27, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano
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Patent number: 4772633Abstract: This invention relates to a novel compound represented by the following general formula (I), its production, and an insecticidal and acaricidal composition containing it as an active ingredient: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.Type: GrantFiled: February 20, 1986Date of Patent: September 20, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
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Patent number: 4772753Abstract: A method for producing 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid and intermediate compounds thereof. The 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid is a very useful intermediate for synthesizing insecticidal and acaricidal compounds of pyrethroid type.Type: GrantFiled: August 7, 1987Date of Patent: September 20, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima
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Patent number: 4742074Abstract: A pyrazolecarboxamide derivative represented by the formula hereinbelow is useful since it has preventively, curatively or systematically controlling effects against various plant diseases and fungicides containing said compound as an active ingredient have excellent controlling activities: ##STR1## wherein R.sup.1 and R.sup.2 which are identical or different and represent each a hydrogen atom, a halogen atom, a methyl group, an ethyl group or a trifluoromethyl group, R.sup.3 represents a hydrogen atom or a methyl group and n represents 0 or 1.Type: GrantFiled: March 31, 1986Date of Patent: May 3, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Sumio Nishida, Tadashi Ohsumi, Kazunori Tsushima, Noritada Matsuo, Kiyoto Maeda, Satoru Inoue
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Patent number: 4714712Abstract: This invention relates to novel carboxylic acid esters represented by the formula (I) below, methods for production thereof and insecticides containing them as the active ingredient, and an alcohol compound useful as an intermediate for manufacturing carboxylic acid esters represented by the formula (I). ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group; when R.sub.1 is a hydrogen atom, R.sub.2 represents a group of the formula ##STR2## in which X and Y are the same or different and represent a hydrogen atom, a methyl group, a halogen atom or a halogenated lower alkyl group, and when R.sub.1 is a methyl group, R.sub.2 represents a methyl group; R.sub.3 represents hydrogen atom or a methyl group; and R.sub.4 represents a hydrogen atom, a lower alkyl group, a lower alkenyl group or a lower alkynyl group.Type: GrantFiled: April 18, 1986Date of Patent: December 22, 1987Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano
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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: 4562213Abstract: Ether compounds of the general formula, ##STR1## wherein W represents CH group or nitrogen atom, and (1) when W is the CH group,R.sub.1 represents hydrogen atom, fluorine atom, chlorine atom, bromine atom or methyl group, R.sub.2 represents hydrogen atom or fluorine atom, R.sub.3 and R.sub.4 are same or different and represent hydrogen atom, a halogen atom, a C.sub.1-4 alkyl, a C.sub.1-4 alkoxyl, difluoromethoxy or 2,2,2-trifluoroethoxy group, or represent, taken together, methylenedioxy group, A represents oxygen atom, methylene group or imino group, and when the A represents oxygen atom or methylene group, X and Y represent, taken together, ethylene group or 1,1-difluoroethylene group and when the A represents imino group, both X and Y represent methyl group or represent, taken together, ethylene group or 1,1-difluoroethylene group, and(2) when W is the nitrogen atom,both R.sub.1 and R.sub.2 represent hydrogen atom, R.sub.3 and R.sub.Type: GrantFiled: May 5, 1983Date of Patent: December 31, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Sumio Nishida, Noritada Matsuo, Kazunori Tsushima, Makoto Hatakoshi, Masachika Hirano
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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: 4385186Abstract: The present invention relates to a method for producing an optically active (+)-(s)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone which comprises reacting (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate of the formula (II), ##STR1## with an optically active (+)-.alpha.-phenyl-.beta.-p-tolylethylamine to produce diastereomer salts, separating an optically active (-)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate by making use of a solubility difference between the diastereomer salts, and then hydrolyzing said optically active acid phthalate in water or a solvent containing water in the presence or absence of a base below the small excess of the stoichiometric amount, and novel (.+-.)-4-hydroxy-3-methyl-2-2'-propynyl-2-cyclopentenone acid phthalate and its production.Type: GrantFiled: June 18, 1980Date of Patent: May 24, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Kazunori Tsushima
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Patent number: 4327094Abstract: A carboxylate of the formula, ##STR1## wherein R.sub.1 is an allyl or propargyl group, R.sub.2 is a group of ##STR2## in which R.sub.3 is a hydrogen atom or a methyl group, and when R.sub.3 is a hydrogen atom, R.sub.4 is a group of ##STR3## (in which R.sub.7 is a chlorine, bromine or fluorine atom, or a methyl, vinyl, methoxycarbonyl or methoxymethyl group, R.sub.8 is a hydrogen, chlorine, bromine or fluorine atom or a methyl group), and when R.sub.3 is a methyl group, R.sub.4 is a methyl group, R.sub.5 is an isopropyl or cyclopropyl group, R.sub.6 is an alkyl group having 1 to 3 carbon atoms or alkoxy group having 1 to 3 carbon atoms, or a chlorine, bromine or fluorine atom, n is 1 or 2, and --(R.sub.6).sub.n may include a 3,4-methylenedioxy group, and its use as an insecticide and/or acaricide.Type: GrantFiled: January 16, 1981Date of Patent: April 27, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Masato Mizutani, Kazunori Tsushima, Yuzuru Sanemitsu, Masachika Hirano