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).

  • Patent number: 5550258
    Abstract: 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: Grant
    Filed: August 23, 1994
    Date of Patent: August 27, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tomonori Iwasaki, Masaya Suzuki, Takashi Furukawa, Kazunori Tsushima, Takao Ishiwatari, Toru Tsuchiya
  • Patent number: 5550260
    Abstract: 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: Grant
    Filed: June 2, 1994
    Date of Patent: August 27, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Tomonori Iwasaki, Masaya Suzuki, Noritada Matsuo
  • Patent number: 5530015
    Abstract: 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: Grant
    Filed: October 19, 1994
    Date of Patent: June 25, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noriyasu Sakamoto, Masaya Suzuki, Toshio Nagatomi, Kazunori Tsushima, Kimitoshi Umeda
  • Patent number: 5093373
    Abstract: 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: Grant
    Filed: January 22, 1991
    Date of Patent: March 3, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
  • Patent number: 5019595
    Abstract: 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: Grant
    Filed: September 20, 1990
    Date of Patent: May 28, 1991
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Toshihiko Yano, Yoko Torisu, Hiroko Sekihachi, Noritada Matsuo, Tohei Takagaki, Kazunori Tsushima
  • Patent number: 5006538
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: April 9, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
  • Patent number: 5004753
    Abstract: 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: Grant
    Filed: April 20, 1990
    Date of Patent: April 2, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ken Otaka, Noritada Matsuo, Kazunori Tsushima, Toshihiko Yano
  • Patent number: 4985457
    Abstract: 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: Grant
    Filed: May 31, 1989
    Date of Patent: January 15, 1991
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroko Kishino, Noritada Matsuo, Tohei Takagaki, Kazunori Tsushima, Toshihiko Yano, Yoko Torisu
  • Patent number: 4840971
    Abstract: 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: Grant
    Filed: April 2, 1987
    Date of Patent: June 20, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Yoo Tanabe, Toshihiko Yano, Masachika Hirano
  • Patent number: 4837242
    Abstract: 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: Grant
    Filed: December 30, 1987
    Date of Patent: June 6, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tadashi Ohsumi, Kazunori Tsushima, Sumio Nishida, Kiyoto Maeda, Tadashi Ooishi, Noritada Matsuo
  • Patent number: 4774369
    Abstract: 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: Grant
    Filed: September 14, 1987
    Date of Patent: September 27, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano
  • Patent number: 4772633
    Abstract: 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: Grant
    Filed: February 20, 1986
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano, Masachika Hirano
  • Patent number: 4772753
    Abstract: 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: Grant
    Filed: August 7, 1987
    Date of Patent: September 20, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima
  • Patent number: 4742074
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: May 3, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sumio Nishida, Tadashi Ohsumi, Kazunori Tsushima, Noritada Matsuo, Kiyoto Maeda, Satoru Inoue
  • Patent number: 4714712
    Abstract: 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: Grant
    Filed: April 18, 1986
    Date of Patent: December 22, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima, Sumio Nishida, Toshihiko Yano
  • Patent number: 4664698
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: May 12, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Hirosi Kisida, Toshihiko Yano
  • Patent number: 4562213
    Abstract: 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: Grant
    Filed: May 5, 1983
    Date of Patent: December 31, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Sumio Nishida, Noritada Matsuo, Kazunori Tsushima, Makoto Hatakoshi, Masachika Hirano
  • Patent number: 4480118
    Abstract: 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: Grant
    Filed: December 30, 1981
    Date of Patent: October 30, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Makoto Hatakoshi, Toshihiko Yano, Nobushige Itaya
  • Patent number: 4385186
    Abstract: 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: Grant
    Filed: June 18, 1980
    Date of Patent: May 24, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Kazunori Tsushima
  • Patent number: 4327094
    Abstract: 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: Grant
    Filed: January 16, 1981
    Date of Patent: April 27, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masato Mizutani, Kazunori Tsushima, Yuzuru Sanemitsu, Masachika Hirano