Patents Assigned to IHARA CHEMICAL INDUSTRY CO.
  • Patent number: 6720463
    Abstract: The present invention provides a process for producing an alkanediol derivative represented by the general formula (II) from an ester compound represented by the general formula (I), safely without giving rise to racemization. The present invention lies in a process for producing an alcohol derivative represented by the following general formula (II): (wherein R2 and R3 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; X is a hydrogen atom or a protecting group for hydroxyl group; and n is 0 or 1), which process comprises reducing an ester compound represented by the following general formula (I): (wherein R1 is an alkyl group having 1 to 4 carbon atoms; and R2, R3, X and n have the same definitions as given above) with sodium borohydride in a mixed solvent of at least one kind of solvent selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons and alicyclic hydrocarbons and a primary alcohol.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: April 13, 2004
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshikazu Kimura, Yukio Uchida, Shuichi Fujimoto
  • Patent number: 6620961
    Abstract: Biarylalkylenecarbamic acid derivative represented by general formula (I): [wherein Q is a phenyl group which may be substituted or the like, X is a halogen atom, a (C1-C6) alkyl group or the like, n is 0 or an integer of from 1 to 4, R1 is a (C1-C6) alkyl group or the like, R2 is a hydrogen atom, a (C1-C6) alkyl group or the like, A is a (C1-C7) alkylene group which may be branched, and G is an oxygen atom, a sulfur atom or a group —NR— (wherein R3 is a hydrogen atom or a (C1-C4) alkyl group)] and agricultural and horticultural fungicides. The agricultural and horticultural fungicides of the present invention are useful as agricultural and horticultural fungicides because they have high preventive effects on cucumber downy mildew, apple scab, wheat powdery mildew, rice blast, cucumber gray mold and rice sheath blight without damaging crops, and are excellent in residual effectiveness and rain-resistance.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: September 16, 2003
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co. Ltd.
    Inventors: Kazuhiro Ikegaya, Masami Ozaki, Takahiro Kawashima, Ichiro Miura, Norimichi Muramatsu
  • Patent number: 6608207
    Abstract: The present invention lies in a process for producing a substituted alkylamine derivative represented by formula (3): (wherein X is halogen, alkyl, alkoxy, cyano or nitro; n is an integer of 1 to 4; and R1 and R2 are each independently hydrogen or phenyl substituted or unsubstituted alkyl and may together form a 5- or 6-membered ring) or an acid addition salt thereof, which process comprises adding a salt of a 2-aminothiophenol derivative represented by formula (1): into an acid to allow the system to have a pH of 6 or less and convert the salt into a free 2-aminothiophenol of formula (1) and then reacting the 2-aminothiophenol derivative with an amino acid-N-carboxyanhydride represented by formula (2):
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: August 19, 2003
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Chikara Hijikata
  • Patent number: 6576631
    Abstract: A pyrimidinylbenzimidazole or triazinylbenzimidazole derivative represented by the general formula (I): wherein A is N or CR3, and R1, R2, R3, X, Y and n are as defined in the disclosure.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: June 10, 2003
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masaru Shibata, Kiyoshi Kawai, Takechi Makihara, Norihisa Yonekura, Takehiro Kawashima, Junetsu Sakai, Norimichi Muramatsu
  • Patent number: 6576765
    Abstract: The present invention provides a process for producing an amic acid ester represented by the following general formula (7) (wherein A is substituted or unsubstituted lower alkylene or the like; R1 is substituted or unsubstituted lower alkyl or the like; and R3 is hydrogen or lower alkyl), which process comprises reacting, in the presence of water, an amino acid represented by formula (1) with a halogenated carbonic acid ester represented by formula (2) (wherein X is halogen) to form an amide compound represented by formula (3), then reacting the amide compound with a halogenated carbonic acid ester represented by formula (4) (wherein R2 is substituted or unsubstituted lower alkyl or the like; and X is halogen) to form, in the system, a mixed acid anhydride represented by formula (5), and reacting the mixed acid anhydride with an amine compound represented by formula (6) (wherein Het is substituted or unsubstituted heterocyclic).
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: June 10, 2003
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Keisuke Isozumi
  • Patent number: 6509354
    Abstract: 3-Arylphenyl sulfide derivatives represented by general formula (I): (wherein R is a C2-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group or the like, B0 to B2 and B3 are hydrogen atoms, halogen atoms, cyano groups, C1-C4 haloalkyl groups or the like, n is 0, 1 or 2, and Ar is a phenyl ring, a pyridine ring, a thiophene ring, a pyrazole ring or the like), and insecticides and miticides containing the 3-arylphenyl sulfide derivatives as an active ingredient.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: January 21, 2003
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Keiji Toriyabe, Nobuo Takefuji, Minoru Itou, Tetsuya Hirade, Kiyotoshi Nishiyama, Mitsuharu Asahida, Yasunobu Maeda, Nobuhide Wada, Toyokazu Fujisawa, Hiroyuki Yano, Masaaki Komatsu, Osamu Tada
  • Patent number: 6504046
    Abstract: A process for producing an amide compound of the following formula by reacting a nitrile compound of the formula with an acid to obtain an oxazolinone compound of the formula and reacting the oxazolinone compound with a carboxy compound of the formula in the presence of a base.
    Type: Grant
    Filed: December 27, 2000
    Date of Patent: January 7, 2003
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Hidetaka Hiyoshi, Shuji Taniguchi, Junko Suzuki
  • Patent number: 6472348
    Abstract: The present invention relates to pyridone derivatives and herbicidal compositions containing the pyridone derivatives as active ingredients.
    Type: Grant
    Filed: May 10, 2001
    Date of Patent: October 29, 2002
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yoshihiro Ito, Atsushi Shibayama, Yoshihiro Yamaji, Ryo Hanai, Sota Uotsu, Hideo Sadohara
  • Patent number: 6469210
    Abstract: A process for producing a phenylalkanoic acid amide of the formula [3] by reacting a carboxylic acid of the formula [1] with a dehydrating agent to produce an oxazolinone compound of the formula [2] and then reacting the oxazolinone compound with methyllithium or a methylmagnesium halide and an intermediate for producing the phenylalkanoic acid compound.
    Type: Grant
    Filed: December 27, 2000
    Date of Patent: October 22, 2002
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Shuji Taniguchi, Hidetaka Hiyoshi, Katsunori Matsumoto
  • Patent number: 6458748
    Abstract: The present invention provides a novel compound which is effective for the removal of a wide variety of weeds including difficult-to-control weeds emerging in paddy field and which is safe to mammals; a process for production thereof; a herbicide containing the compound as an active ingredient; and novel raw material compounds used in said process. The present invention relates to a di- or trifluoromethanesulfonyl anilide derivative represented by the following general formula: (wherein R1 is a hydrogen atom, an alkyl group or an alkoxyalkyl group; and R2 is a hydrogen atom when R1 is a hydrogen atom or an alkyl group, and is a hydrogen atom or a fluorine atom when R1 is an alkoxyalkyl group), or a salt thereof, both of said derivative and said salt having a herbicidal activity.
    Type: Grant
    Filed: January 22, 2001
    Date of Patent: October 1, 2002
    Assignees: Ihara Chemical Industry Co., Ltd., Kumiai Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Masao Nakatani, Masatoshi Tamaru, Takeshi Danjo, Yukimasa Ono, Katsutada Yanagisawa
  • Patent number: 6414186
    Abstract: A method for preparing chloromethylphenylacetic acids represented by formula (II): wherein a methylphenylacetic acid represented by formula (I): is reacted with a chlorine gas, in an inert solvent, under the irradiation with light or in the presence of a radical initiator, is disclosed. According to the preparation method, high purity chloromethylphenylacetic acids can be prepared at a high yield, without using toxic sulfuryl chloride as a chlorinating agent, by chlorinating the methyl group of the methylphenylacetic acids at a high selectivity while suppressing by-production of a dichloro form or &agr;-chloro form.
    Type: Grant
    Filed: December 18, 2000
    Date of Patent: July 2, 2002
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Kimitoshi Kusagaya, Yoshihiro Takao, Motoaki Nakagawa, Masafumi Matsuzawa
  • Patent number: 6326497
    Abstract: A heterocyclic halide represented by a general formula (I): T—CH2—Y  (I) (wherein T denotes a heterocyclic group, and Y denotes a chlorine atom, bromine atom or iodine atom), is reacted with ammonia in the presence of an aromatic aldehyde represented by a general formula (II): A—CHO  (II) (wherein A denotes an aromatic group), to thereby produce an aminomethyl-heterocyclic derivative represented by a general formula (III): T—CH2—N═CH—A  (III) (wherein T denotes a heterocyclic group, and A denotes an aromatic group).
    Type: Grant
    Filed: June 9, 2000
    Date of Patent: December 4, 2001
    Assignee: Ihara Chemical Industries Co. Ltd.
    Inventor: Yusuke Hamada
  • Patent number: 6316658
    Abstract: N-Cyclopropyl-2-difluoromethoxy-3-halogenoanilines which serve as important intermediates in the preparation of quinolonecarboxylic acids useful as synthetic antimicrobial agents from industrially inexpensive and easily available raw materials; and intermediates for the preparation thereof. Specifically, compounds represented by the general formula (1), (2) and (3), wherein X is halogeno; and Y is nitro or amino, (2) wherein X is halogeno; and R1 is lower alkyl, (3) wherein X is halogeno; and R is hydrogen or —CH═C(CO2R2)2, R2 being lower alkyl.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: November 13, 2001
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Hiroaki Takeuchi
  • Patent number: 6313071
    Abstract: A phenylacetylene derivative represented by the formula [I]: {wherein X is a halogen atom, a C1-C6 alkyl group, a C2-C6 alkoxy group, a C2-C6 haloalkyl group, etc., n is 0 or an integer of from 1 to 4, R1 is a C1-C6 alkyl group, R2 is a hydrogen atom, a C1-C6 alkyl group, a C2-C6 alkynyl group, a C2-C6 alkynyl group, a C1-C6 alkoxy group, etc., A is a C1-C6 alkylene group which may be branched, G is an oxygen atom, a sulfur atom or a —NR3— group; R3 is a hydrogen atom or a C1-C6 alkyl group, and Y is a hydrogen atom, a C1-C10 alkyl group, said group may be substituted by a halogen atom, a hydroxyl group or a C1-C6 alkoxy group], a C2-C6 alkenyl group, etc.; and an agricultural/horticultural fungicide containing the same as the active ingredient.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: November 6, 2001
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Kazuhiro Ikegaya, Shunichiro Fukumoto, Masami Ozaki, Takahiro Kawashima, Haruchika Sekido, Norimichi Muramatsu
  • Patent number: 6265349
    Abstract: The present invention relates to pyridone derivatives and herbicidal compositions containing the pyridone derivatives as active ingredients.
    Type: Grant
    Filed: October 27, 1999
    Date of Patent: July 24, 2001
    Assignees: Kumiai Chemical Industry Co., Ltd, Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yoshihiro Ito, Atsushi Shibayama, Yoshihiro Yamaji, Ryo Hanai, Sota Uotsu, Hideo Sadohara
  • Patent number: 6225505
    Abstract: The present invention lies in a process for producing a trifluoromethylthiomethylbenzene derivative represented by the following general formula (2): (wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cyano group, a nitro group, or a benzoyl group which may be substituted with halogen atom, alkyl group, alkoxy group, aliphatic or aromatic acyl group, nitro group, cyano group or alkoxycarbonyl group; n is an integer of 1 to 5; when n is an integer of 2 or more, a plurality of R's may be the same of each independently different), which process comprises reacting, in acetonitrile, a benzyl halide derivative represented by the following general formula (1): (wherein R and n have the same definitions as given above; and X is a halogen atom, an alkylsulfonyloxy group or an arylsulfonyloxy group which may be substituted with alkyl group or halogen atom) with thiophosgene and potassium fluoride.
    Type: Grant
    Filed: February 1, 2000
    Date of Patent: May 1, 2001
    Assignees: Ihara Chemical Industry Co., LTD, Kumiai Chemical Industry Co., LTD
    Inventors: Yoshikazu Kimura, Hidetaka Hiyoshi, Keiji Toriyabe, Nobuhide Wada
  • Patent number: 6197969
    Abstract: The present invention provides a process for producing a substituted alkylamine represented by formula (3): or a salt thereof, which process comprises reacting a 2-aminothiophenol derivative metal salt represented by formula (1): with an amino acid-N-carboxy anhydride represented by formula (2): and then subjecting the reaction product to cyclization under an acidic condition. A substituted alkylamine typified by 1-(2-benzothioazolyl)akylamine, or a salt thereof can be produced from a 2-aminothiophenol derivative industrially at a high handleability and a high yield, and even when the intended substituted alkylamine is an optically active compound, the intended product can be produced without reducing the optical purity of the optically active raw material.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: March 6, 2001
    Assignee: Ihara Chemical Industry Co., LTD.
    Inventors: Kazuto Umezu, Shuji Taniguchi, Mahito Ogawa, Hidetaka Hiyoshi
  • Patent number: 6166246
    Abstract: The present invention provides a 4-fluorosalicylic acid derivative represented by the following general formula (1): ##STR1## (wherein X.sup.1, X.sup.2 and X.sup.3 are each independently a hydrogen atom or a halogen atom with a proviso that there is no case in which all of X.sup.1, X.sup.2 and X.sup.3 are hydrogen atoms or fluorine atoms simultaneously); and a process for producing the above 4-fluoro-salicylic acid derivative.The 4-fluorosalicylic acid derivative of the present invention is a novel compound not described in any literature and is very suitable as a raw material for production of a 3-fluorophenol derivative (the 3-fluorophenol derivative is very useful as an intermediate for liquid crystal, recording material, medicine and agricultural chemical) because the 4-fluorosalicylic acid derivative can be easily converted to the 3-fluorophenol derivative.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: December 26, 2000
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Kazuto Umezu
  • Patent number: 6162944
    Abstract: Process for production of, from inexpensive raw materials of high commercial availability, N-cyclopropylanilines which are an important intermediate in producing a quinolonecarboxylic acid having a cyclopropyl group at the 1-position, a fluorine atom at the 6-position, and an alkyl group, an alkoxy group or a fluorine-substituted methoxy group at the 8-position (this quinolonecarboxylic acid is a useful synthetic antibacterial agent); and intermediates therefor. For example, a process for producing an N-cyclopropyl-3,4-difluoroaniline represented by the formula (4): ##STR1## includes reacting, in the presence of an acid in an alcohol type solvent, a 3,4-difluoro-2-substituted-aniline with a 1-alkoxy-1-trialkylsilyloxycyclopropane to produce an N-alkoxycyclopropylaniline represented by the general formula (3): ##STR2## and then reducing the N-alkoxycyclopropylaniline.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: December 19, 2000
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Kazuto Umezu, Yusuke Hamada, Fumiya Tabuchi
  • Patent number: 6130187
    Abstract: A benzofuran-7-yl uracil derivative represented by the general formula (1): ##STR1## (wherein each of X and Y is a hydrogen atom, a halogen atom or the like, R.sup.1 is a hydrogen atom, an alkyl group or the like, R.sup.2 is a haloalkyl group or the like, R.sup.3 is a hydrogen atom, a halogen atom or the like, each of R.sup.4 and R.sup.5 which are independent of each other, is a hydrogen atom, an alkyl group, a haloalkyl group, a halogen atom, a cyano group, a phenyl group, a benzyl group, a nitro group or the like), and a herbicide containing it as an active ingredient.The compound of the present invention represented by the general formula (1) exhibits excellent herbicidal effects against various weeds which cause trouble in upland fields, such as, broad leaved weeds, gramineous weeds and perennial or annual cyperaceous weeds, over a wide range from the pre-emergence to the growing stage. It can further control annual weeds and perennial weeds growing in paddy fields.
    Type: Grant
    Filed: August 5, 1998
    Date of Patent: October 10, 2000
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Miyazaki, Takeshi Deguchi, Takayoshi Takehi, Masatoshi Tamaru, Yoshihiro Yamaji, Ryo Hanai, Sota Uotsu, Hideo Sadohara