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).
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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: 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: 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: 4531008Abstract: 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: GrantFiled: May 23, 1983Date of Patent: July 23, 1985Assignee: Sumitomo Chemical Co., Ltd.Inventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4503071Abstract: 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: GrantFiled: August 17, 1977Date of Patent: March 5, 1985Assignee: Sumitomo Chemical Company, LimitedInventors: Masachika Hirano, Isao Ohno, Nobuo Ohno, Akihiko Mine
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Patent number: 4443438Abstract: 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: GrantFiled: August 6, 1982Date of Patent: April 17, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Kasamatsu, Masachika Hirano, Takeshi Okuno
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Patent number: 4394379Abstract: 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: GrantFiled: January 17, 1980Date of Patent: July 19, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Osamu Kirino, Masachika Hirano, Hisami Takeda, Toshiro Kato
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Patent number: 4376785Abstract: 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: GrantFiled: June 9, 1981Date of Patent: March 15, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Masachika Hirano
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Patent number: 4357348Abstract: 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: GrantFiled: December 3, 1979Date of Patent: November 2, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Kasamatsu, Masachika Hirano, Takeshi Okuno
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Patent number: 4336194Abstract: 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: GrantFiled: July 13, 1979Date of Patent: June 22, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Tadashi Ohsumi, Nobushige Itaya, Masachika Hirano
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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
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Patent number: 4326058Abstract: 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: GrantFiled: January 28, 1980Date of Patent: April 20, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Okabe, Masachika Hirano, Kunio Mukai
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Patent number: 4321212Abstract: 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: GrantFiled: March 24, 1981Date of Patent: March 23, 1982Assignee: Sumitomo Chemical Company LimitedInventors: Yukio Suzuki, Masachika Hirano, Koichi Aketa
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Patent number: 4320126Abstract: 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: GrantFiled: August 27, 1979Date of Patent: March 16, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Okabe, Kunio Mukai, Masachika Hirano
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Patent number: 4308258Abstract: 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: GrantFiled: January 24, 1980Date of Patent: December 29, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Okabe, Kunio Mukai, Masachika Hirano
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Patent number: 4307036Abstract: 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: GrantFiled: April 11, 1980Date of Patent: December 22, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Suzuki, Kohichi Aketa, Masachika Hirano
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Patent number: 4303672Abstract: 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: GrantFiled: February 21, 1980Date of Patent: December 1, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Masachika Hirano, Tadashi Ohsumi, Kiyoshi Kasamatsu, Takashi Kato
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Patent number: 4266074Abstract: 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: GrantFiled: July 16, 1975Date of Patent: May 5, 1981Assignee: Sumitomo Chemical Company LimitedInventors: Keimei Fujimoto, Nobuo Ohno, Yoshitoshi Okuno, Toshio Mizutani, Isao Ohno, Masachika Hirano, Nobushige Itaya, Takashi Matsuo
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Patent number: 4263463Abstract: 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: GrantFiled: October 26, 1976Date of Patent: April 21, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeyoshi Kitamura, Norbushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
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Patent number: 4238406Abstract: 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: GrantFiled: January 29, 1979Date of Patent: December 9, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Yukio Suzuki, Kohichi Aketa, Masachika Hirano