Patents by Inventor Masachika Hirano

Masachika Hirano 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: 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: 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: 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: 4531008
    Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: July 23, 1985
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
  • Patent number: 4503071
    Abstract: An insecticidal composition comprising, as an active ingredient, an optically active .alpha.-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate and an inert carrier having a strong insecticidal activity without any appreciable toxicity to plants as well as to mammals.
    Type: Grant
    Filed: August 17, 1977
    Date of Patent: March 5, 1985
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masachika Hirano, Isao Ohno, Nobuo Ohno, Akihiko Mine
  • Patent number: 4443438
    Abstract: The present invention relates to insecticidal compositions of low toxicity to fishes and mammals characterized by containing m-(p-bromophenoxy)-.alpha.-cyanolbenzyl trans- or trans-rich-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate of the formula (I), ##STR1## and at least one of the organo-phosphoric esters of the formula (II), ##STR2## wherein R.sub.1 and R.sub.2 are each a C.sub.1 -C.sub.3 alkyl group, X.sub.1, X.sub.2 and X.sub.3 are each an oxygen or sulfur atom, Y.sub.1 and Y.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 lower alkyl, methylmercapto, cyano or nitro group or a halogen atom, Z is a carbon or nitrogen atom and n is 0 or 1, in a ratio of 1 to 1-100 (part by weight) of the former to the latter, and insecticides obtained by mixing said compositions with a carrier or a diluent and if necessary an additive. The term "trans-rich" shows the ratio of trans/cis is not less than 75/25.
    Type: Grant
    Filed: August 6, 1982
    Date of Patent: April 17, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Kasamatsu, Masachika Hirano, Takeshi Okuno
  • Patent number: 4394379
    Abstract: Amide phosphorothiolate derivatives of the formula, ##STR1## wherein X is an oxygen or sulfur atom, Y is an oxygen or sulfur atom or imino group, R.sub.1 and R.sub.2, which may be the same or different, are each a C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a C.sub.1 -C.sub.4 alkyl group, R.sub.4 is a hydrogen atom or methyl group, R.sub.5 is a C.sub.1 -C.sub.3 alkyl, methoxy or ethoxy group, Z is a hydrogen atom, a methyl group or chlorine atom and n is 1 or 2, a process for producing said derivatives characterized by reacting the salt of thiophosphoric ester represented by the formula, ##STR2## wherein X, Y, R.sub.1 and R.sub.2 are as defined above and M is a sodium or potassium atom or ammonium group, with a haloacetamide derivative of the formula, ##STR3## wherein R.sub.3, R.sub.4, R.sub.5, Z and n are as defined above and W is a halogen atom, and a combined insecticide, acaricide, nematocide and/or fungicide containing said derivatives as an active ingredient.
    Type: Grant
    Filed: January 17, 1980
    Date of Patent: July 19, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Osamu Kirino, Masachika Hirano, Hisami Takeda, Toshiro Kato
  • Patent number: 4376785
    Abstract: The present invention relates to cyclopropanecarboxylates of the formula (I), ##STR1## wherein R and X may be same or different, each is a chlorine or bromine atom, and their production and use as an insecticide and/or acaricide.
    Type: Grant
    Filed: June 9, 1981
    Date of Patent: March 15, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritada Matsuo, Masachika Hirano
  • Patent number: 4357348
    Abstract: The present invention relates to insecticidal compositions of low toxicity to fishes and mammals characterized by containing m-(p-bromophenoxy)-.alpha.-cyanobenzyl trans- or trans-rich-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate of the formula (I), ##STR1## and a carbamic ester of the formula (III), ##STR2## wherein R is a group of the formula, ##STR3## in which X is a C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxyl group and n is 1 or 2, in a ratio of 1 to 1-100 (part by weight) of the former to the latter, and insecticides obtained by mixing said compositions with a carrier or a diluent and if necessary an additive. The term "trans-rich" shows the ratio of trans/cis is not less than 75/25.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: November 2, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kiyoshi Kasamatsu, Masachika Hirano, Takeshi Okuno
  • Patent number: 4336194
    Abstract: Carboxylic acid esters of the formula (I), ##STR1## wherein X is a hydrogen atom, or a C.sub.1 -C.sub.3 alkyl or a C.sub.1 -C.sub.3 alkoxyl group or a halogen atom linked to the meta or para position and R.sub.1 is a group of the formula (II) or (III), ##STR2## wherein R.sub.2 is a hydrogen atom or a methyl group, and when R.sub.2 is a methyl group R.sub.3 is also a methyl group, and when R.sub.2 is a hydrogen atom R.sub.3 is a group of the formula, ##STR3## (wherein R.sub.5 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, vinyl or a C.sub.1 -C.sub.3 alkoxymethyl group, R.sub.6 is a hydrogen or halogen atom or a methyl group, or, taken together, R.sub.5 and R.sub.6 may form a tetramethylene group by connecting together at ends thereof), R.sub.4 is a halogen atom or a C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or 3,4-methylenedioxy group, n is 1 or 2 and Y is a isopropyl or cyclopropyl group.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: June 22, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tadashi Ohsumi, Nobushige Itaya, Masachika Hirano
  • 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
  • Patent number: 4326058
    Abstract: Phosphoro-thioates or dithioates of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.3 alkyl group, R.sub.1 is a C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.4 alkylamino or allylamino group, R.sub.2 is a halogen atom, a C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.3 alkyl group, R.sub.3 is a hydrogen or halogen atom or a C.sub.1 -C.sub.3 alkyl group, R.sub.4 is a C.sub.1 -C.sub.3 alkyl group, and X is an oxygen or sulfur atom, provided that when R.sub.1 is a C.sub.1 -C.sub.4 alkylamino or allylamino group, X is an oxygen atom, a process for producing phosphoro-thioates or dithioates of the formula (I) characterized by condensing a pyrimidine of the formula (II), ##STR2## wherein Y is a halogen atom, and R.sub.2, R.sub.3 and R.sub.4 are as defined above, with a thio- or dithio-phosphate of the formula, ##STR3## wherein M is an alkali metal atom or an ammonium group, and R, R.sub.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: April 20, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Okabe, Masachika Hirano, Kunio Mukai
  • Patent number: 4321212
    Abstract: A method for preparing an optically active .alpha.-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)-isovalerate, which consists substantially of or is rich in (S)-.alpha.-cyano-3-phenoxybenzyl (S)-2-(4-substituted-phenyl)isovalerate.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: March 23, 1982
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Yukio Suzuki, Masachika Hirano, Koichi Aketa
  • Patent number: 4320126
    Abstract: Organophosphorus esters of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.2 alkyl group, R.sub.1 is a C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.4 alkylamino, phenyl or phenoxy group, R.sub.2 and R.sub.3, which may be the same or different, are each a C.sub.1 -C.sub.5 alkyl or methoxy C.sub.2 -C.sub.3 alkyl group and X is an oxygen or sulfur atom, a method for producing organophosphorus esters of the formula (I) characterized by condensation reaction of s-triazines of the formula, ##STR2## wherein M is a potassium or sodium atom and R.sub.2 and R.sub.3 are as defined above, with a halogenated compound of the formula, ##STR3## wherein Y is a halogen atom and R, R.sub.1 and X are as defined above, and an insecticide, acaricide and/or nematocide characterized by containing organophosphorus esters of the formula (I) as an active ingredient.
    Type: Grant
    Filed: August 27, 1979
    Date of Patent: March 16, 1982
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Okabe, Kunio Mukai, Masachika Hirano
  • Patent number: 4308258
    Abstract: Pyrimidin-4-yl-phosphorothionates of the formula (I), ##STR1## wherein R is a C.sub.1 -C.sub.2 alkyl group, R.sub.1 is a C.sub.1 -C.sub.2 alkoxyl or C.sub.1 -C.sub.4 alkylamino group, R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.1 -C.sub.3 alkoxyl or methylmercapto group, and X is an oxygen or sulfur atom; a process for producing pyrimidin-4-yl-phosphorothionates of the formula (I) characterized by condensing a 4-hydroxypyrimidine of the formula (II), ##STR2## wherein R.sub.2 and R.sub.3, which may be the same or different, are each a halogen atom, a C.sub.1 -C.sub.3 alkoxyl or methylmercapto group, with a halogen compound of the formula, ##STR3## wherein R is a C.sub.1 -C.sub.2 alkyl, R.sub.1 is a C.sub.1 -C.sub.2 alkoxyl or C.sub.1 -C.sub.
    Type: Grant
    Filed: January 24, 1980
    Date of Patent: December 29, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Okabe, Kunio Mukai, Masachika Hirano
  • Patent number: 4307036
    Abstract: A method for preparing .alpha.-cyano-3-phenoxybenzyl 2-(4-substituted-phenyl)isovalerates which consist substantially of or are rich in the enantiomer pair (S)-.alpha.-cyano-3-phenoxybenzyl (S)-2-(4-substituted-phenyl)isovalerate and (R)-.alpha.-cyano-3-phenoxybenzyl (R)-2-(4-substituted-phenyl)isovalerate.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: December 22, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Suzuki, Kohichi Aketa, Masachika Hirano
  • Patent number: 4303672
    Abstract: The present invention relates to carboxylic esters of the formula (I), ##STR1## wherein X is a chlorine or bromine atom, and their production and use as an insecticide and/or acaricide.
    Type: Grant
    Filed: February 21, 1980
    Date of Patent: December 1, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masachika Hirano, Tadashi Ohsumi, Kiyoshi Kasamatsu, Takashi Kato
  • Patent number: 4266074
    Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal composition containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: May 5, 1981
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
  • Patent number: 4263463
    Abstract: Novel alkynylcyclopropanecarboxylic acid esters represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, C.sub.1 -C.sub.4 alkoxy C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio C.sub.1 -C.sub.4 alkyl, aryl, aryl C.sub.1 -C.sub.4 alkyl, furyl, substituted furyl, thienyl, substituted thienyl, furfuryl, substituted furfuryl, thenyl, substituted thenyl, cyclo C.sub.3 -C.sub.6 alkyl, substituted cyclo C.sub.3 -C.sub.6 alkyl, cyclo C.sub.3 -C.sub.6 alkenyl or substituted cyclo C.sub.3 -C.sub.6 alkenyl; R.sub.2 and R.sub.3 individually represent hydrogen, halogen, lower alkyl having up to 5 carbon atoms, lower alkenyl having up to 5 carbon atoms, lower alkynyl having up to 5 carbon atoms, aryl, aryl C.sub.1 -C.sub.4 alkyl or may form a carbon-carbon bond; or R.sub.1 and R.sub.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: April 21, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shigeyoshi Kitamura, Norbushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
  • Patent number: 4238406
    Abstract: An .alpha.-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate which consists substantially of or is rich in (S)-.alpha.-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate and (R)-.alpha.-cyano-3-phenoxybenzyl (R)-2-(4-chlorophenyl)isovalerate. A method for preparing the same and an insecticidal and acaricidal composition.
    Type: Grant
    Filed: January 29, 1979
    Date of Patent: December 9, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Suzuki, Kohichi Aketa, Masachika Hirano