Patents by Inventor Rikuo Nasu
Rikuo Nasu 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: 5491239Abstract: A method for halogenating an aromatic compound, which comprises reacting the aromatic compound of the formula (I): ##STR1## wherein X is a hydroxyl group, an amino group or an acylamino group, each of Z.sub.1 and Z.sub.2 is a hydrogen atom or a halogen atom, one of R and Y is a hydrogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and Q is a nitrogen atom or --C(T).dbd. (wherein T is a hydrogen atom, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group), with a halogenating agent to obtain a 3-halogenoaromatic compound of the formula (II): ##STR2## wherein one of R' and Y' is a halogen atom and the other is a nitro group, a cyano group or a trifluoromethyl group, and X, Z.sub.1, Z.sub.2 and Q are as defined above.Type: GrantFiled: November 2, 1993Date of Patent: February 13, 1996Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Motohiko Hamaguchi, Hayato Ariyoshi
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Patent number: 5399767Abstract: A process for producing 3,5-difluoroaniline, which comprises reacting a benzonitrile compound of the formula (I): ##STR1## wherein each of X.sub.1, X.sub.2 and X.sub.3 is hydrogen, chlorine, bromine or a cyano group, provided that at least one of X.sub.1 to X.sub.3 is a cyano group, with a mineral acid for hydrolysis and decarboxylation to obtain an aniline compound of the formula (II): ##STR2## wherein each of X.sub.4, X.sub.5 and X.sub.6 is hydrogen, chlorine or bromine, provided that at least one of X.sub.4 to X.sub.6 is hydrogen, and in the case of a compound of the formula (II) wherein X.sub.4, X.sub.5 and X.sub.6 are not simultaneously hydrogen, reacting such a compound with hydrogen in a presence of a catalyst for reduction to obtain 3,5 -difluoroaniline.Type: GrantFiled: February 8, 1994Date of Patent: March 21, 1995Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Motohiko Hamaguchi
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Patent number: 5290944Abstract: A method for producing a dichloromethylpyridine of the formula (II): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which are independent of one another, is a hydrogen atom, a halogen atom, an alkoxy group or a phenoxy group which may be substituted, provided that R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are not simultaneously hydrogen atoms, which comprises reacting a trichloromethylpyridine of the formula (I): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with a reducing agent, wherein:(1) a dialkyl phosphite or a trialkyl phosphite is used as the reducing agent, and the reaction is conducted in the presence of a basic substance and an alcohol solvent, or(2) a trialkyl phosphine or triphenyl phosphine is used as the reducing agent, and the reaction is conducted in the presence of an alcohol solvent.Type: GrantFiled: December 14, 1992Date of Patent: March 1, 1994Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Taku Shimura, Isamu Katsuyama
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Patent number: 4995898Abstract: Novel imidazole compounds are disclosed, which are represented by the following general formula: ##STR1## wherein: R.sub.1 represents a cyano group or a --CSNHR.sub.5 group, wherein R.sub.5 represents a hydrogen atom, a C.sub.1-4 alkyl group, or a --COR.sub.6 group, wherein R.sub.6 represents a C.sub.1-4 alkyl group, a halogenated C.sub.1-4 alkyl group, or a phenyl group;R.sub.2 and R.sub.3 each represents a hydrogen atom; a halogen atom; a nitro group; a cyano group; a trimethylsilyl group; a C.sub.3-6 cycloalkyl group; a naphthyl group; a C.sub.1-12 alkyl group which is optionally substituted with one or more halogen atoms, hydroxyl groups, acetoxy groups, C.sub.1-4 alkoxy groups, halogenated C.sub.1-4 alkoxy groups, phenyl groups, halogenated phenyl groups, or C.sub.1-4 alkylated phenyl groups; a C.sub.2-10 alkenyl group which is optionally substituted with one or more halogen atoms; a C.sub.Type: GrantFiled: March 14, 1988Date of Patent: February 26, 1991Assignee: Ishihara Sangyo Kaisha, Ltd.Inventors: Rikuo Nasu, Terumasa Komyoji, Toshio Nakajima, Kazumi Suzuki, Keiichiro Ito, Takeshi Oshima, Hideshi Yoshimura
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Patent number: 4420618Abstract: 5,6-Dichloro-.beta.-trifluoromethylpyridine or 2,5,6-trichloro-.beta.-trifluoromethylpyridine is produced by reacting 6-chloro-.beta.-trifluoromethylpyridine or 2,6-dichloro-.beta.-trifluoromethylpyridine with chlorine gas to chlorinate the 5-position of pyridine nucleus thereof:(1) at a temperature of 100.degree. C. to 250.degree. C. and at least sufficient amount of chlorine for the reaction;(2) in the presence of the catalyst of amount of at least 40% by weight (based on the 6-chloro or/and 2,6-dichloro-.beta.-trifluoromethylpyridine), the catalyst being chlorides a metallic element selected from the group consisting of iron, tungsten, molybdenum, titanium, and antimony.Type: GrantFiled: July 26, 1982Date of Patent: December 13, 1983Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Isao Yokomichi, Takahiro Haga, Rikuo Nasu, Kuniaki Nagatani, Toshio Nakajima
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Patent number: 4267336Abstract: 4-(Pyridyl-2-oxy)phenoxyalkanecarboxylic acid derivative is produced by reacting 2-phenoxypyridine derivative with 4-hydroxyphenoxyalkanecarboxylic acid derivative. The products which are effective as an active ingredient of a herbicide can be obtained at high yield by an interphenoxylation.Type: GrantFiled: April 7, 1980Date of Patent: May 12, 1981Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Rikuo Nasu, Itaru Shigehara
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Patent number: 4241213Abstract: 2-Chloro-5-trichloromethyl pyridine is produced by reacting .beta.-picoline with chlorine in a gaseous phase at 300.degree. to 500.degree. C. in the presence of an inert diluent of nitrogen, a halogenated methane, a halogenated ethane a halogenated ethylene or a mixture thereof. 2-Chloro-5-trichloromethyl pyridine is useful as an intermediate for medicines, agricultural chemicals, dyes especially herbicides.Type: GrantFiled: September 13, 1979Date of Patent: December 23, 1980Assignee: Ishihara Sangyo Kaisha LimitedInventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Rikuo Nasu, Takao Awazu, Junichi Kawashima
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Patent number: 4231787Abstract: Phenoxypropane compounds represented by the general formula (I): ##STR1## wherein X is a 4-halophenoxy group, a 2,4-dihalophenoxy group, a 4-trifluoromethylphenoxy group, a 2-halo-4-trifluoromethylphenoxy group, a 5-halopyridyl-2-oxy group or a 3,5-dihalopyridyl-2-oxy group; and Y is a halogen atom, a hydroxy group, a (C.sub.1 -C.sub.4)-alkoxy group in which the alkyl moiety thereof may be substituted with a hydroxy group(s), a (C.sub.1 -C.sub.4)alkylcarbonyloxy group or a phenylcarbonyloxy group in which the phenyl moiety thereof may be substituted with a halogen atoms(s), useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.Type: GrantFiled: June 21, 1978Date of Patent: November 4, 1980Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Ryohei Takahashi, Kanichi Fujikawa, Rikuo Nasu, Nobuyuki Sakashita
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Patent number: 4218237Abstract: A sulfonanilide compounds having the formula (I): ##STR1## wherein X.sub.1 is hydrogen atom, a halogen atom, methyl group or trifluoromethyl group, X.sub.2 is hydrogen atom or a halogen atom, R.sub.1 is a (C.sub.1 -C.sub.4) alkyl group or a halo(C.sub.1 -C.sub.4) alkyl group, R.sub.2 is hydrogen atom, a (C.sub.1 -C.sub.4) alkyl group, trifluoromethyl group or nitro group, R.sub.3 is hydrogen atom, --SO.sub.2 R.sub.1 group (R.sub.1 is the same as defined above), a (C.sub.2 -C.sub.4) acyl group, a (C.sub.2 -C.sub.4) acylmethyl group, a (C.sub.1 -C.sub.4) alkyl group, a (C.sub.1 -C.sub.4) alkoxy (C.sub.1 -C.sub.4) alkyl group or a (C.sub.3 -C.sub.4) alkenyl group, R.sub.4 is hydrogen atom or a halogen atom, and n is an integer of 0 to 2; and a salt thereof, which is useful as a herbicidal component.Type: GrantFiled: November 17, 1978Date of Patent: August 19, 1980Assignee: Ishihara Sangyo Kaisha LimitedInventors: Ryuzo Nishiyama, Kanichi Fujikawa, Fumio Kimura, Rikuo Nasu, Nobuyuki Sakashita, Shigeyuki Nishimura
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Patent number: 4173638Abstract: N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X.sub.1 represents a halogen atom; X.sub.2 represents hydrogen or halogen atom; X.sub.3 and X.sub.4 respectively represent hydrogen or chlorine atom; X.sub.5 represents hydrogen or halogen atom; and X.sub.6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds.The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.Type: GrantFiled: October 21, 1977Date of Patent: November 6, 1979Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Rikuo Nasu, Tadaaki Toki, Toshihiko Yamamoto
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Patent number: 4173637Abstract: N-benzoyl N'-pyridyloxy phenyl urea having the formula ##STR1## wherein X.sub.1 represents a halogen atom or methyl group; X.sub.2 represents hydrogen or halogen atom; X.sub.3 and X.sub.4 respectively represent hydrogen or halogen atom; X.sub.5 represents hydrogen or halogen atom; and X.sub.6 represents a halogen atom or nitro or trifluoromethyl group are novel compounds. The compositions containing the compound as the active ingredient are effective as the insecticide for extinction of injurious insects with high safety in agricultural, forestry and hygienic applications.Type: GrantFiled: April 24, 1978Date of Patent: November 6, 1979Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Rikuo Nasu, Tadaaki Toki, Toshihiko Yamamoto, deceased, by Hikotaro Yamamoto, legal representative
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Patent number: 4140520Abstract: Phenoxy malonic acids and derivatives thereof represented by the general formula (I): ##STR1## wherein X is a 4-trifluoromethylphenoxy group or a 3,5-dichloropyridyl-2-oxy group; and R is a hydroxy group, an --O-- cation group or a (C.sub.1 - C.sub.4)alkoxy group, useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.Type: GrantFiled: April 8, 1977Date of Patent: February 20, 1979Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Rikuo Nasu, Nobuyuki Sakashita
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Patent number: 4134751Abstract: Phenoxy valeric acids and derivatives thereof represented by the general formula (I): ##STR1## wherein X is a hydrogen atom or a chlorine atom; and R is a hydroxy group, an --O-cation group, a (C.sub.1 - C.sub.4)alkoxy group, a (C.sub.1 - C.sub.4)alkylthio group, a benzyloxy group, or an amino group which may be substituted with a (C.sub.1 - C.sub.4)alkyl group(s), a phenyl group or a pyridine-2-yl group, useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.Type: GrantFiled: April 14, 1977Date of Patent: January 16, 1979Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Rikuo Nasu, Itaru Shigehara, Nobuyuki Sakashita
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Patent number: 4105435Abstract: Phenoxypropane compounds represented by the general formula (I): ##STR1## wherein X is a 4-halophenoxy group, a 2,4-dihalophenoxy group, a 4-trifluoromethylphenoxy group, a 2-halo-4-trifluoromethylphenoxy group, a 5-halopyridyl-2-oxy group or a 3,5-dihalopyridyl-2-oxy group; and Y is a halogen atom, a hydroxy group, a (C.sub.1 -C.sub.4)alkoxy group in which the alkyl moiety thereof may be substituted with a hydroxy group(s), a (C.sub.1 -C.sub.4)alkylcarbonyloxy group or a phenylcarbonyloxy group in which the phenyl moiety thereof may be substituted with a halogen atom(s), useful as a herbicide; a herbicidal composition containing the compound; and methods of controlling weeds using such materials.Type: GrantFiled: October 22, 1976Date of Patent: August 8, 1978Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Ryohei Takahashi, Kanichi Fujikawa, Rikuo Nasu, Nobuyuki Sakashita
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Patent number: H811Abstract: A biocidal composition containing, as active ingredients, at least one imidazole compound represented by formula (I): ##STR1## wherein R.sup.1 represents a phenyl group, a halogen-substituted phenyl group, an alkyl group, or a halogen-substituted alkyl group; and R.sup.2 represents a halogen atom, and at least one other specific compound. The combination of the compound represented by formula (I) and other specific compound can produce an unexpected effect in amount required and biocidal spectrum.Type: GrantFiled: March 13, 1989Date of Patent: August 7, 1990Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Rikuo Nasu, Terumasa Komyoji, Toshio Nakajima, Kazumi Suzuki, Keiichiro Ito, Tekeshi Ohshima, Hideshi Yoshimura