Patents by Inventor Toshio Mizutani
Toshio Mizutani 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: 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: 4327109Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy of phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: April 22, 1980Date of Patent: April 27, 1982Assignee: Sumitomo Chemical Company LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno
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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: 4229469Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH.dbd.CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: December 22, 1975Date of Patent: October 21, 1980Assignee: Sumitomo Chemical Company LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno
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Patent number: 4118505Abstract: Novel alkynyl esters of cyclopropanecarboxylic acid represented by the formula, ##STR1## wherein R.sub.1 represents hydrogen, lower alkyl having 1-4 carbon atoms, lower alkenyl having 2-4 carbon atoms, lower alkynyl having 2-4 carbon atoms, C.sub.1 -C.sub.2 alkoxy-C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkylthio-C.sub.1 -C.sub.4 alkyl, furyl, thienyl, furfuryl, thenyl, cyclo-C.sub.3 -C.sub.6 alkyl, oxygen atom-containing cyclo-C.sub.3 -C.sub.6 alkyl, cyclo-C.sub.5 -C.sub.6 alkenyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenyl, halo-C.sub.2 -C.sub.4 alkenyl, phenyloxymethyl, phenylthiomethyl, cyclo-C.sub.5 -C.sub.6 alkenylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkenylmethyl, cyclo-C.sub.5 -C.sub.6 alkylmethyl, oxygen atom-containing cyclo-C.sub.4 -C.sub.6 alkylmethyl or ##STR2## IN WHICH X is halogen, nitro, cyano, methylenedioxy, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy, dimethylamino, m is 0, 1, 2 or 3, n is 0, 1, 2 or 3 and each X may be different when n is 2 or 3; R.sub.Type: GrantFiled: December 2, 1975Date of Patent: October 3, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeyoshi Kitamura, Nobushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
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Patent number: 4062968Abstract: 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: December 13, 1977Assignee: 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: 4058622Abstract: Substituted acetate compounds represented by the formula ##STR1## which are useful as pesticides and pesticidal compositions containing the substituted acetate compounds as active ingredients, as well as processes for preparing the compounds and the compositions are disclosed.Type: GrantFiled: March 12, 1975Date of Patent: November 15, 1977Assignee: 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: 4039680Abstract: 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: August 2, 1977Assignee: 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: 4031235Abstract: 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: June 21, 1977Assignee: 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: 4008268Abstract: A process for isomerizing 2-(.beta.,.beta.-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylic acid represented by the formula, ##STR1## which comprises heating the acid of the formula (I) in the presence of the anhydride of the acid or a reagent producing the acid anhydride in the reaction system.The ester resulting from 2-(.beta.,.beta.-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylic acid and, for example, 3-phenoxybenzyl alcohol is a compound which has a very wide range of insecticidal spectrum and has a very high controlling effect as a low-toxicity insecticide not only for domestic use and public health but also against insects injurious to agriculture or forestry, and in the case of the 3-phenoxybenzyl ester or 5-benzyl-3-furylmethyl ester of the 2-(.beta.,.beta.-dichlorovinyl)-3,3-dimethylcyclopropanecarboxylic acid, the trans-isomer is lower than the cis-isomer in toxicity to warm-blooded animals.Type: GrantFiled: June 10, 1975Date of Patent: February 15, 1977Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Nobushige Itaya, Toshiko Nishijima, Osamu Magara
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Patent number: 4003945Abstract: 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: April 15, 1974Date of Patent: January 18, 1977Assignee: Sumitomo Chemical Company, LimitedInventors: Shigeyoshi Kitamura, Nobushige Itaya, Yoshitoshi Okuno, Nobuo Ohno, Takashi Matsuo, Masachika Hirano, Toshio Mizutani, Hisami Takeda
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Patent number: 3998868Abstract: A compound of the formula, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##STR2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH=CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: August 14, 1975Date of Patent: December 21, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno
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Patent number: 3996244Abstract: 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 11, 1973Date of Patent: December 7, 1976Assignee: 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: 3995432Abstract: A toroidal shaped collector with a radial inlet and a single discharge outlet includes a pair of substantially parallel spaced baffle plates extending from the inlet partway into the collector chamber, disposed in the plane of the collector and serves to receive and discharge the airflow from a gas generator such as a gas turbine engine particularly adapted for nonaircraft applications.Type: GrantFiled: July 28, 1975Date of Patent: December 7, 1976Assignee: United Technologies CorporationInventors: Leonard Noryk, Toshio Mizutani
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Patent number: 3981903Abstract: A new pyrethroidal pesticide containing as an active ingredient a pesticidally effective amount of novel cyclopropanecarboxylic acid esters represented by the formula, ##EQU1## wherein R is a hydrogen atom, a halogen atom, a methyl or a methoxy group, and R.sub.1 and R.sub.2 are hydrogen atom, methyl group or a halogen atom, which have a low toxicity to mammals, excellent pesticidal effect on injurious pests in cereal storage, agriculture and forestry and a wide range of uses for prevention of epidemics.Type: GrantFiled: July 25, 1974Date of Patent: September 21, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Masachika Hirano, Isao Ohno, Yoshitoshi Okuno, Osamu Magara, Nobushige Itaya, Toshio Nishioka, Toshio Mizutani, Nobuo Ohno, Takashi Matsuo, Hisami Takeda
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Patent number: 3969393Abstract: A process for preparing an organic acid ester of the formula (I), ##EQU1## wherein R.sub.1 is a hydrogen atom or a methyl group, R.sub.2 is a methyl group, a vinyl group, a 2,2-dichlorovinyl group, a 1-propenyl group, a 2-methyl-1-propenyl group, a 2-carbomethoxy-1-propenyl group, a 2-methoxymethyl-1-propenyl group, a 1,3-butadienyl group, a 2-methyl-1,3-butadienyl group or a cyclopentylidenemethyl group when R.sub.1 is a hydrogen atom, and R.sub.2 is a methyl group when R.sub.1 is a methyl group; which comprises reacting an acid of the formula (II), ##EQU2## wherein R.sub.1 and R.sub.2 are each as defined above, or its reactive derivative, or mixture of the acid and its reactive derivative with a quaternary ammonium salt of the formula (III), ##SPC1##wherein X is a halogen atom, A is an alkylamine, pyridine or an N-alkylaniline.Type: GrantFiled: August 6, 1974Date of Patent: July 13, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Yoshitaka Ume, Takashi Matsuo
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Patent number: 3968124Abstract: A process for preparing a substituted phenyl-acetic acid ester of the formula (I), ##SPC1##wherein R.sub.1 is an ethyl group or an isopropyl group, R.sub.2 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a methoxy group, a halogen atom or a methylenedioxy group, which comprises reacting a quaternary ammonium salt of the formula (III), ##SPC2##wherein X is a halogen atom, and A is an alkylamine, pyridine or an N-alkylaniline, with a carboxylic acid of the formula (II), ##SPC3##wherein R.sub.1 and R.sub.2 are each as defined above, its reactive derivative, or a mixture of the acid and its reactive derivative.Type: GrantFiled: August 6, 1974Date of Patent: July 6, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Nobuo Ohno, Yoshitaka Ume, Takashi Matsuo
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Patent number: 3966963Abstract: An insecticidal composition and method containing a compound of the formula, ##EQU1## wherein R is hydrogen or methyl group, which is harmless to warm-blooded animals.Type: GrantFiled: January 13, 1975Date of Patent: June 29, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshitoshi Okuno, Nobushige Itaya, Toshio Mizutani
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Patent number: 3954814Abstract: A compound of the formula, ##EQU1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are respectively hydrogen atom or methyl, R.sub.5 is a member of ##SPC1##--CH.sub.2 Z or ##EQU2## wherein R.sub.6 is hydrogen atom or methyl, R.sub.7 is alkenyl, alkadienyl, alkynyl or benzyl, R.sub.8 is hydrogen atom, ethynyl or cyano, R.sub.9 is hydrogen atom, a halogen atom or alkyl, R.sub.10 is a halogen atom, alkyl, alkenyl, alkynyl, benzyl, thenyl, furylmethyl, phenoxy, substituted phenoxy or phenylthio, or R.sub.9 and R.sub.10 are bonded at the ends to form polymethylene chain containing or not containing oxygen or sulfur atom, Y is oxygen atom, sulfur atom or --CH=CH--, n is 1 or 2, Z is phthalimido, thiophthalimido, di- or tetra-hydrophthalimido or dialkylmaleimido, R.sub.11 is phenyl, thienyl or furyl and X is a halogen atom, which is useful as an active ingredient of insecticides.Type: GrantFiled: June 23, 1972Date of Patent: May 4, 1976Assignee: Sumitomo Chemical Company, LimitedInventors: Toshio Mizutani, Nobushige Itaya, Nobuo Ohno, Takashi Matsuo, Shigeyoshi Kitamura, Yositosi Okuno