Patents by Inventor Ryuzo Nishiyama

Ryuzo Nishiyama 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: 4563529
    Abstract: A trifluoromethylpyridine selected from the group consisting of .alpha.-trifluoromethylpyridine, .gamma.-trifluoromethylpyridine, a bis(trifluoromethyl)pyridine and chlorides thereof which have 1 to 3 chlorine atoms in its pyridine nucleus is produced by reacting a pyridine derivative selected from the group consisting of .alpha.-picoline, .gamma.-picoline and a lutidine with chlorine and anhydrous hydrogen fluoride at a temperature of 300.degree. to 600.degree. C. in a vapor phase in the presence of a diluent and a catalyst comprising a fluoride of a metallic element selected from the group consisting of aluminum, chromium, iron, nickel, manganese, cobalt and copper.
    Type: Grant
    Filed: June 4, 1981
    Date of Patent: January 7, 1986
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4546191
    Abstract: A trifluoromethyl-2-(thio)pyridone compound having the formula: ##STR1## wherein X represents a hydrogen atom or a halogen atom, Y.sub.1 and Y.sub.2 each represents a hydrogen atom, a halogen atom or a trifluoromethyl group, and Z represents an oxygen atom or a sulfur atom, in which either Y.sub.1 or Y.sub.2 represents a trifluoromethyl group, and when X and Y.sub.2, or X and Y.sub.1 represent a hydrogen atom at the same time, then Z represents a sulfur atom,and a process for preparing the same.
    Type: Grant
    Filed: March 19, 1980
    Date of Patent: October 8, 1985
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Takahiro Haga, Kuniaki Nagatani, Kouji Hayashi
  • Patent number: 4417055
    Abstract: A pyridine derivative having the formula ##STR1## wherein X.sup.2 and Y.sup.2 represents hydrogen atom or chlorine atom is produced by reacting a pyridine compound having the formula ##STR2## wherein X.sup.1 and Y.sup.1 represent hydrogen atom or chlorine atom, with chlorine and anhydrous hydrogen fluoride by a vapor phase reaction in the presence of a catalyst at a temperature of 250.degree. to 600.degree. C. using as the catalyst a fluoride of a metal selected from the group consisting of copper, vanadium, tin, bismuth, zirconium, magnesium, barium, zinc, calcium, potassium and sodium.
    Type: Grant
    Filed: March 9, 1982
    Date of Patent: November 22, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4406841
    Abstract: A process for producing 2,6-difluorobenzonitrile comprises reducing a chloro fluorobenzonitrile selected from 3-chloro-2,6-difluorobenzonitrile, 3,5-dichloro-2,6-difluorobenzonitrile or a mixture thereof by hydrogen gas in the presence of a palladium or platinum catalyst at a temperature of 0.degree. to 200.degree. C.
    Type: Grant
    Filed: August 17, 1982
    Date of Patent: September 27, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Yasuhiro Tsujii, Shigeo Murai, Hisayoshi Jyonishi
  • Patent number: 4380670
    Abstract: An aminobenzene is produced by reacting a chlorobenzene with ammonia in the presence of a copper type catalyst, namely by reacting ammonia with 3,5-diaminochlorobenzene to produce 1,3,5-triaminobenzene at a temperature of 150.degree. to 250.degree. C. at a molar ratio of ammonia of 2 to 10 to 3,5-diaminochlorobenzene in the presence of a copper compound catalyst.
    Type: Grant
    Filed: April 3, 1981
    Date of Patent: April 19, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Itaru Shigehara, Mikio Miyaji
  • Patent number: 4368340
    Abstract: 1,3,5,-Trichlorobenzene is produced by chlorinating 1,3,5-trihalobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom. The gaseous 1,3,5-halobenzene having 1 to 3 bromine atom and 2 to 0 chlorine atom is brought into contact with chlorine gas at a molar ratio of 0.5 to 3.0 of the stoichiometric amount of chlorine required for said conversion, in a vapor phase at a temperature of 280.degree. to 500.degree. C.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: January 11, 1983
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Itaru Shigehara, Mikio Miyaji
  • Patent number: 4367336
    Abstract: A 2-substituted-5-trifluoromethylpyridine compound represented by Formula (I): ##STR1## wherein X is a hydrogen atom or a halogen atom, and Y is a cyano group or a carboxy group, provided that Y is a cyano group, then X is a halogen atom, or a salt thereof, and a process for the production of the same. This compound is useful as an intermediate for the production of various fine chemicals.
    Type: Grant
    Filed: February 23, 1981
    Date of Patent: January 4, 1983
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Takahiro Haga, Toru Koyanagi
  • Patent number: 4347390
    Abstract: 1-Bromo-3,5-dichlorobenzene is produced in high efficiency by a special isomerization of monobromodichlorobenzene in the presence of an aluminum halide and separating the object product and recycling a residue.1-Bromo-3,5-dichlorobenzene is useful intermediates for various agricultural chemicals, dyes and medicines.
    Type: Grant
    Filed: November 13, 1980
    Date of Patent: August 31, 1982
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Itaru Shigehara, Kuniaki Nagatani, Shigeyuki Nishimura
  • Patent number: 4344951
    Abstract: N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR1## wherein X represents a halogen atom; R represents a C.sub.1 -C.sub.4 alkyl group and n is 0, 1 or 2 are useful as insecticides.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: August 17, 1982
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Takahiro Haga, Tadaaki Toki, Tohru Koyanagi, Shigeo Murai
  • Patent number: 4331670
    Abstract: A novel compound for combatting insect, mite, fungus or bacterium is a pyridylaniline represented by the following formula (I) ##STR1## wherein X is a trifluoromethyl group, a halogen atom, a lower alkyl group or a lower alkoxy group; n is an integer of 0 to 4; R is a hydrogen atom or an acetyl group; Y is a hydrogen atom, a halogen atom a lower alkoxy group, a lower alkylthio group, a hydroxy group, an azido group or a phenoxy group of which the phenyl ring may be substituted by a hydroxy group; Z.sub.1, Z.sub.2 and Z.sub.3 are a trifluoromethyl group or a nitro group, provided that at least one of X is a trifluoromethyl group or a lower alkyl group when n is an integer of 3 or 4.
    Type: Grant
    Filed: December 3, 1980
    Date of Patent: May 25, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Takahiro Haga, Tadaaki Toki, Kuniaki Nagatani, Osamu Imai
  • Patent number: 4321388
    Abstract: Compounds having the formula ##STR1## wherein X represents a halogen atom, nitro, methyl, or trifluoromethyl group; Y represents a halogen or hydrogen atom or methyl group; and Z represents a halogen atom are useful as agricultural chemicals and pharmaceuticals.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: March 23, 1982
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Hiroyuki Mori, Yasuo Ogawa, Takahiro Haga, Kuniaki Nagatani
  • Patent number: 4310530
    Abstract: N-benzoyl N'-pyridyloxy phenyl ureas having the formula ##STR1## wherein X.sub.1 represents a hydrogen or halogen atom or methyl, trifluoromethyl or nitro group; X.sub.2 represents a hydrogen or halogen atom; X.sub.3, X.sub.4, X.sub.5 and X.sub.6 respectively represent a hydrogen or halogen atom or a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylcarbonyl group, a C.sub.1 -C.sub.4 alkoxycarbonyl group or nitro group; when X.sub.3 and X.sub.6 are both hydrogen atoms, at least one of X.sub.4 and X.sub.5 is a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 alkoxy group, a C.sub.1 -C.sub.4 alkylcarbonyl group, or a C.sub.1 -C.sub.4 alkoxycarbonyl group; and X.sub.7 represents a hydrogen or halogen atom; and Y represents oxygen or sulfur atom.
    Type: Grant
    Filed: September 3, 1980
    Date of Patent: January 12, 1982
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Takahiro Haga, Tadaaki Toki, Tohru Koyanagi, Shigeo Murai
  • Patent number: 4288599
    Abstract: Pyridine derivatives having a trifluoromethyl group at .beta.-position thereof are produced by reacting .beta.-picoline with chlorine and hydrogen fluoride in a vapor phase at high temperature for a short time. The reaction condition can be mild and the yield of the object compound is increased by reacting them in the presence of a specific metal fluodie. The pyridine derivatives useful as starting materials for agricultural chemicals and medicines can be continuously obtained by a simple reaction at high yield.
    Type: Grant
    Filed: February 26, 1980
    Date of Patent: September 8, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4266963
    Abstract: A pyrazole derivative having the formula (I): ##STR1## wherein X and Y each represents a chlorine atom, a nitro group or a trifluoromethyl group, and Z represents a hydrogen atom or a halogen atom, which is useful as a herbicidal component.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: May 12, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Fumio Kimura, Takahiro Haga, Nobuyuki Sakashita, Tetsuji Nishikawa
  • Patent number: 4267336
    Abstract: 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: Grant
    Filed: April 7, 1980
    Date of Patent: May 12, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Rikuo Nasu, Itaru Shigehara
  • Patent number: 4266064
    Abstract: A chloro .beta.-trifluoromethylpyridine is produced by reacting a chloro .beta.-trichloromethylpyridine with hydrogen fluoride in the presence of a specific metal fluoride in a vapor phase at high temperature for a short time. The chloro .beta.-trifluoromethylpyridines which are useful as intermediates for agricultural chemicals and medicines can be obtained at high yield.
    Type: Grant
    Filed: March 5, 1980
    Date of Patent: May 5, 1981
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4241213
    Abstract: 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: Grant
    Filed: September 13, 1979
    Date of Patent: December 23, 1980
    Assignee: Ishihara Sangyo Kaisha Limited
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Rikuo Nasu, Takao Awazu, Junichi Kawashima
  • Patent number: 4235621
    Abstract: 2-Substituted phenoxy-3-chloro-5-trifluoromethyl pyridine having the formula (I): ##STR1## wherein X is a hydrogen atom; a (C.sub.1 -C.sub.4)alkyl group; a (C.sub.1 -C.sub.4)alkoxy group; a --COOR.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or a (C.sub.1 -C.sub.4)alkyl group; or an ##STR2## group wherein R.sub.2 is a hydrogen atom, a cation, a (C.sub.1 -C.sub.4)alkyl group or a benzyl group; and Y is a halogen atom, a nitro group or a cyano group, useful as a herbicide.
    Type: Grant
    Filed: May 30, 1979
    Date of Patent: November 25, 1980
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Takahiro Haga, Tadaaki Toki, Terumasa Komyoji, Nobuyuki Sakashita, Kazuyuki Maeda
  • Patent number: 4231787
    Abstract: 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: Grant
    Filed: June 21, 1978
    Date of Patent: November 4, 1980
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Ryohei Takahashi, Kanichi Fujikawa, Rikuo Nasu, Nobuyuki Sakashita
  • Patent number: 4230481
    Abstract: A pyrazole derivative having the formula (I): ##STR1## wherein X.sub.1 and X.sub.2 are respectively a (C.sub.1 -C.sub.4) alkyl group, Y is a halogen atom, nitro group, acetyl group, cyano group, or a phenoxy group which may be substituted with one or more halogen atoms, l is an integer of 1 to 3, and Z is a (C.sub.1 -C.sub.4) alkyl group, a (C.sub.2 -C.sub.4) alkenyl group, a (C.sub.2 -C.sub.4) alkynyl group, acetylmethyl group, an aralkyl group in which the aryl moiety thereof may be substituted with one or more nitro groups, a phenacyl group in which the phenyl moiety thereof may be substituted with one or more halogen atoms, one or more nitro groups, one or more (C.sub.1 -C.sub.4) alkyl groups, one or more (C.sub.1 -C.sub.4) alkoxy groups, one or more (C.sub.1 -C.sub.
    Type: Grant
    Filed: July 31, 1978
    Date of Patent: October 28, 1980
    Assignee: Ishihara Sangyo Kaisha Limited
    Inventors: Ryuzo Nishiyama, Fumio Kimura, Takahiro Haga, Nobuyuki Sakashita, Tetsuji Nishikawa