Patents Assigned to IHARA CHEMICAL INDUSTRY CO.
  • Patent number: 5658375
    Abstract: A method is provided for inhibiting growth of fouling organisms on structures in contact with water, which entails contacting said structure in contact with water with an effective amount of a compound having the formula: ##STR1## wherein R.sup.1 is a lower alkyl group, or a phenyl group which is unsubstituted or substituted with halogen or lower alkyl or both; each X.sup.1 being a halogen atom; n being an integer of 1-5; when n is two or more; each X.sup.1 is the same or different; and Y.sup.1 is a hydrogen atom or a group-Z--Y.sup.2, wherein Z is carbonyl or sulfonyl; and Y.sup.2 is unsubstituted aryl or aryl substituted by a lower alkyl group, or salts thereof.
    Type: Grant
    Filed: August 15, 1996
    Date of Patent: August 19, 1997
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Hideo Okada, Atsuya Mochizuki, Hideo Ohi
  • Patent number: 5616537
    Abstract: A condensed heterocyclic derivative of the formula (I): ##STR1## (wherein R is a hydroxyl group, R.sup.3 or R.sup.4 is an alkoxy group, W is an oxygen atom, Yn is a hydrogen atom, Z is a methine group, and A is a 5- or 6-membered heterocyclic ring which may be substituted, and a herbicide, are presented. When used for paddy field treatment, upland soil treatment and foliage treatment, the condensed heterocyclic derivative of the present invention exhibits excellent herbicidal activities against gramineous and non-gramineous weeds without adversely affecting crop plants.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: April 1, 1997
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Sumio Yokota, Masafumi Matsuzawa, Nobuyuki Ohba, Toshihiro Nagata, Shigehiko Tachikawa, Takeshige Miyazawa, Katsutada Yanagisawa
  • Patent number: 5616594
    Abstract: The invention provides a triazole derivative represented by a general formula ##STR1## (wherein R.sup.1 is an alkyl group, X is a hydrogen atom, a halogen atom or an alkyl group, n is an integer of 1-5, Y is a halogen atom, a nitro group or an alkyl group, and m is an integer of 2-5) as well as insecticide and acaricide containing the same as an active ingredient.The triazole derivatives according to the invention exhibit an excellent effectiveness against harmful pests, particularly aphids and mites.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: April 1, 1997
    Assignees: Ihara Chemical Industry Co. Ltd., Kumiai Chemical Industrial Co., Ltd.
    Inventors: Atsuhiko Ikeda, Masami Ozaki, Reijiro Honami, Takashi Yumita, Hiroyuki Yano, Yuki Nakano, Yutaka Kurihara, Tadayoshi Hirano
  • Patent number: 5608080
    Abstract: The present invention provides a process for producing a 2-substituted benzo[b]thiophene, which is characterized by reacting a substituted or unsubstituted 2-halogenobenzaldehyde with sulfur and a compound represented by general formula (1)H.sub.i S.sub.j M.sub.k (1)(wherein M represents an alkali metal; i represents an integer of 0 or 1; j represents an integer of 1 or more; and k represents an integer of 1-2 with a proviso that i+k=2), or with a compound of general formula (1) wherein j is 2 or more, in the presence of an aprotic polar solvent, and then reacting the reaction mixture with a compound represented by general formula (2)XCH.sub.2 R (2)(wherein X represents a halogen atom; and R represents an acyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted arylcarbonyl group or a cyano group) to give rise to intramolecular ring closure.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: March 4, 1997
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Naoto Yazawa, Yoshinori Saito, Hidetaka Hiyoshi
  • Patent number: 5603755
    Abstract: The present invention provides a preventive agent for fouling organisms, which comprises, as an effective ingredient, at least one compound selected from compounds represented by general formula (1) ##STR1## [wherein R.sup.1 is a lower alkyl group, or a phenyl group which may be substituted with a halogen atom(s) and/or a lower alkyl group(s); each X.sup.1 is a halogen atom; n is an integer of 1-5; when n is 2 or more, X.sup.1 s may be the same or different; and Y.sup.1 is a hydrogen atom or a group --Z--Y.sup.2 (Z is a carbonyl group or a sulfonyl group, and Y.sup.2 is a substituted or unsubstituted aryl group or a lower alkyl group], or salts thereof. The present preventive agent for fouling organisms, which contains a compound(s) other than organotin compounds as an effective ingredient, has high safety, prevents the settlement of fouling organisms to ships, in-water structures, fishing nets, etc. at a low effective ingredient content, and exhibits an antifouling effect stably over a long period of time.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: February 18, 1997
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Hideo Okada, Atsuya Mochizuki, Hideo Ohi
  • Patent number: 5574064
    Abstract: The present invention provides an agricultural or horticultural fungicide including an effective amount of an amino-acid derivative represented by the formula: ##STR1## wherein R.sup.1 represents a lower alkyl group (optionally having at least one same or different substituent of a halogen atom, an alkoxy group, and a cyano group), R.sup.2 represents an ethyl group, or an n-propyl group, R.sup.3 represents a hydrogen atom or a lower alkyl group, R.sup.4 represents a hydrogen atom, R.sup.5, R.sup.6, and R.sup.7 independently represent a hydrogen atom or a lower alkyl group, R.sup.8 represents a hydrogen atom, or a lower alkyl group, Z.sup.1 and Z.sup.2 independently represent an oxygen atom or a sulfur atom, Z.sup.3 represents an oxygen atom, or a sulfur atom, Q represents a phenyl group, m represents an integer from 0 to 2, and n represents 0 or 1.
    Type: Grant
    Filed: December 28, 1994
    Date of Patent: November 12, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masaru Shibata, Kazuhiko Sugiyama, Norihisa Yonekura, Junetsu Sakai, Yoshiyuki Kojima, Shigeru Hayashi
  • Patent number: 5567825
    Abstract: The improvement proposed in the invention consists in the use of, as a reaction solvent in the reaction of a 1,3,5-trialkyl-2-halogenobenzene and an alkali metal salt of 3-mercapto-1H-1,2,4-triazole in the presence of a copper catalyst for the preparation of a 3-(2,4,6-trialkylphenylthio)-1H-1,2,4-triazole useful as an intermediate in the preparation of herbicide compounds, a compound represented by the general formula ##STR1## in which R is a lower alkyl group, Y is a methylene group or an N-(lower alkyl)imino group and Z is a divalent hydrocarbon group to form a 5-membered ring or 6-membered ring together with the group --N--CO--Y--, such as N-methyl-2-pyrrolidone, N,N'-dimethyl-2-imidazolidinone and N,N'-dimethyl propylene urea, so as to obtain the product in a high yield without the danger of explosion.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: October 22, 1996
    Assignees: Chugai Seiyaku Kabushiki Kaisha, Ihara Chemical Industry Co., Ltd.
    Inventors: Hideo Ohi, Noriyuki Ozawa
  • Patent number: 5536837
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like, R.sup.3 and R.sup.4 represent independently an alkyl group, alkoxy group, or the like, and X and Y represent independently a methyne group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: July 16, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihisa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5534481
    Abstract: The present invention provides an indazolesulfonylurea derivative represented by the general formula: ##STR1## [wherein R.sup.1 is a hydrogen atom or an alkyl group, etc., R.sup.2 and R.sup.3 are the same or different and represent a hydrogen atom, a halogen atom, an alkyl group, the formula --COR.sup.4 (wherein R.sup.4 represents an alkoxy group, etc.), an alkoxy group, a haloalkoxy group or a cyano group, etc., X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or an alkyl group, etc., A and B are the same or different and represent a halogen atom, an alkoxy group or an alkyl group, etc., and Z represents a nitrogen atom or a methine group], as well as a herbicide containing it as an active ingredient and an intermediate for its production.The compound of the present invention exhibits excellent herbicidal effects over a wide range from the preemergence stage to the growing stage of various weeds which are problematic in agricultural fields.
    Type: Grant
    Filed: January 30, 1995
    Date of Patent: July 9, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Chiharu Suzuki, Katsumi Masuda, Masatoshi Tamaru, Masahito Inamori, Nobuo Takefuji, Katsutada Yanagisawa, Yasunori Ogawa
  • Patent number: 5527763
    Abstract: A herbicide containing a pyrimidine or triazine derivative of the formula (I): ##STR1## [wherein A is a furan ring, a pyrimidine ring, a 1,2,4-triazine ring or the like which may suitably be substituted, R is a hydroxyl group or a lower alkoxy group, each of R.sup.1 and R.sup.2 which may be the same or different, is a halogen atom, a lower alkyl group or a lower alkoxy group, W is an oxygen atom or a sulfur atom, and Z is nitrogen or a methine group] and its salt, as an active ingredient, is presented. The pyrimidine or triazine derivative of the present invention has excellent herbicidal effects against noxious weeds in paddy fields, upland fields and non-agricultural fields.
    Type: Grant
    Filed: December 8, 1993
    Date of Patent: June 18, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Miyazaki, Masafumi Matsuzawa, Takumi Yoshimura, Kuniaki Shimizu, Shigehiko Tachikawa
  • Patent number: 5512551
    Abstract: The present invention provides benzohydroximoylazole derivatives represented by the following novel formula: ##STR1## wherein R is a branched alkyl group having not fewer than 3 carbon atoms, a fluorine-substituted alkyl group having not fewer than 2 carbon atoms, a branched alkoxy group having not fewer than 3 carbon atoms, a halogen-substituted alkoxy group having not fewer than 3 carbon atoms, a cycloalkyl group, a cycloalkylmethyl group which may be substituted with one or two alkyl groups, a substituted silylalkyl group, a substituted silylalkyloxy group, a cycloalkyloxy group which may be substituted with one or two alkyl groups, an alkylthio group, a halogen-substituted alkyloxyalkyl group, an alkynyl group, or a halogen-substituted alkenyloxy group;X is a hydrogen atom, a chlorine atom, or a fluorine atom;Y is an alkyl group; and Z is a nitrogen atom or a methyne group,and methods for producing the same, insecticides including the benzohydroximoylazole derivatives as an active ingredient.
    Type: Grant
    Filed: July 27, 1994
    Date of Patent: April 30, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Keiji Toriyabe, Takayoshi Takehi, Yukio Nezu, Yuki Nakano, Tomonori Shimazu
  • Patent number: 5482951
    Abstract: A novel triazole derivative for use in an insecticide or an acaricide has a general formula [I]: ##STR1## (wherein R.sup.1 is an alkyl group, X is a hydrogen atom, a halogen atom or the like, n is an integer of 1-5, A is an oxygen atom, a sulfur atom or the like, k is 0 or 1, R.sup.2 is a hydrogen atom, a halogen atom or the like, m is an integer of 1-5) and controls various injurious insects and mites, particularly mites and aphids without damaging crops.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: January 9, 1996
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masami Ozaki, Atsuhiko Ikeda, Reijiro Honami, Takashi Yumita, Naokazu Minoguchi, Hiroyuki Yano, Norihiko Izawa, Tadayoshi Hirano
  • Patent number: 5478799
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like. R.sup.3 and R.sup.4 represent independently an alkyl group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: December 26, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihisa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5466705
    Abstract: There are provided triazole derivatives represented by a general formula ##STR1## (wherein R.sup.1 is an alkyl group having a carbon number of 1-4, R.sup.2 is a phenyl group substitutable with a halogen atom, an alkyl group having a carbon number of 1-4 or the like, R.sup.3 is an alkenyl group having a carbon number of 3 or more substitutable with 1-4 halogen atoms, a phenyl group substituted with 1 or more halogen atoms or the like), a method producing the same, and a pest controlling agent containing the same as an active ingredient.The triazole derivatives according to the invention have an excellent insecticidal action against harmful pests such as hemipteran insects, lepidopteran insects, dipteran insects, mites and the like and also have an excellent ovicidal action against eggs of these pests. Furthermore, they have a preventively controlling effect on serious diseases such as sheath blight, blast and the like without badly affecting crops.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: November 14, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masami Ozaki, Atsuhiko Ikeda, Takashi Yumita, Reijiro Honami, Naokazu Minoguchi, Hiroyuki Yano, Norihiko Izawa, Tadayoshi Hirano
  • Patent number: 5444060
    Abstract: The present invention provides an N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring represented by formula [I]: ##STR1## wherein R.sup.1 represents an alkyl group, an alkenyl group, or the like, R.sup.2 represents a hydrogen atom, an alkyl group, or the like, R.sup.3 and R.sup.4 represent independently an alkyl group, alkoxy group, or the like, and X and Y represent independently a methyne group or a nitrogen atom; or the salt of the same, a method for producing the same, and a biocide containing the same as an active ingredient. The N-sulfonyl carboxylic amide derivative including an N-containing 6-membered aromatic ring according to the present invention exhibits superior effects against blight caused by plant pathogenic fungi belonging to Oomycetes such as downy mildew, late blight, or the like in a low concentration as well as controls weeds occurring in paddy fields and plowed fields.
    Type: Grant
    Filed: November 2, 1993
    Date of Patent: August 22, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihasa Yonekura, Junetsu Sakai, Shigeru Hayashi
  • Patent number: 5418212
    Abstract: The present invention provides a novel alkanoic acid amide derivative of the formula, ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group or an alkoxyalkoxy group, R.sup.2 is a group of --SO.sub.2 R or a hydroxyl group, R.sup.5 is an alkyl group, R.sup.3 is an alkyl group, a cycloalkyl group, a cycloalkenyl group or a phenyl group, R.sup.4 is a hydrogen atom or an alkyl group, X and Y may be the same or different and are an alkoxy group, an alkylamino group or a dialkylamino group, and Z is a methine group or a nitrogen atom) and its salt, a process for preparing the same and a herbicidal composition containing the same as an effective ingredient.This compound kills annual and perennial weeds grown in paddy fields and upland fields at a small dose, and is safe to a useful crop plant.
    Type: Grant
    Filed: April 27, 1993
    Date of Patent: May 23, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
  • Patent number: 5411934
    Abstract: The present invention provides a novel alkanoic acid amide derivative of the formula, ##STR1## (wherein R.sup.1 is a hydrogen atom, an alkyl group or an alkoxyalkoxy group, R.sup.2 is a group of -SO.sub.2 R or a hydroxyl group, R.sup.5 is an alkyl group, R.sup.3 is an alkyl group, a cycloalkyl group, a cycloalkenyl group or a phenyl group, R.sup.4 is a hydrogen atom or an alkyl group, X and Y may be the same or different and are an alkoxy group, an alkylamino group or a dialkylamino group, and Z is a methine group or a nitrogen atom) and its salt, a process for preparing the same and a herbicidal composition containing the same as an effective ingredient.This compound kills annual and perennial weeds grown in paddy fields and upland fields at a small dose, and is safe to a useful crop plant.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: May 2, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
  • Patent number: 5410009
    Abstract: A polyurethaneurea elastomer obtained by reacting a polyisocyanate component obtained by reacting 1,5-naphthalene diisocyanate with a polyol, with an amine component consisting essentially of an amine compound of the formula (1): ##STR1## wherein R is a bivalent polyalkylene polyether or polyalkylene polyester having an average molecular weight of at least 200, which may contain unsaturated bonds in the polyalkylene.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: April 25, 1995
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Kaneyoshi Kato, Yoshijiro Oyaizu
  • Patent number: 5403816
    Abstract: 3-Pyrimidinyloxy-substituted picolinic acid derivatives of the formula ##STR1## and their salts are useful as herbicides against annual and perennial gramineous and broadleaf weeds while exhibiting low phytotoxicity to desired crop plants.
    Type: Grant
    Filed: April 20, 1993
    Date of Patent: April 4, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Fumiaki Takabe, Yoshihiro Saito, Masatoshi Tamaru, Shigehiko Tachikawa, Ryo Hanai
  • Patent number: 5401711
    Abstract: The present invention provides a herbicidal composition containing a novel pyrimidine derivative having the formula (1), ##STR1## wherein R.sup.1 is a trifluoromethanesulfonyioxy group, an ethenyl group which may be substituted, or an ethynyl group which may be substituted; R.sup.2 is a hydrogen atom, an alkyl group, 2-trimethylsilyl ethyl group; R.sup.3 and R.sup.4 are the same or different, and are a methoxy group or a halogen atom; X is an oxygen atom or a sulfur atom; and Z is a methine group; or its salt, as an active ingredient.The pyrimidine derivative of the present invention exhibits an excellent herbicidal effect against noxious weeds which grow in paddy fields, upland fields and non-agricultural fields.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: March 28, 1995
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Sato, Koichiro Kaku, Shigehiko Tachikawa