Patents Assigned to Ihara Chemical Industry Co., Ltd.
  • Patent number: 6075055
    Abstract: A phenylalkane amide compound having the formula (1): ##STR1## wherein R.sup.1 -R.sup.4, X, n, Y, Z and Q are as defined herein. The compound is useful as an agricultural or horticultural fungicide.
    Type: Grant
    Filed: December 1, 1997
    Date of Patent: June 13, 2000
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Katsumi Masuda, Ikumi Urushibata, Tsuyoshi Asahara, Katsumi Furuse, Yoshiyuki Kojima, Hiroshi Abe
  • Patent number: 6066744
    Abstract: Presentation of a method for producing a 5-methylindoline represented by the formula: ##STR1## (wherein R is a hydrogen atom or a lower alkyl group), which comprises catalytically hydrogenating a 1-(substituted)benzyl-5-formylindoline represented by the formula: ##STR2## (wherein R.sup.1 is a hydrogen atom or a lower alkyl group, and R.sup.2 is a hydrogen atom, a lower alkyl group or a lower alkoxy group) in the presence of an inert solvent and a palladium catalyst.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: May 23, 2000
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Hideo Ooi, Toshihisa Watanabe, Chikara Hijikata
  • Patent number: 6048823
    Abstract: A pyridone derivative represented by the general formula: ##STR1## {wherein R is an alkyl group or a haloalkyl group, R.sup.1 is a hydrogen atom, an alkyl group, a haloalkyl group, an acetyl group, an amino group, an alkoxycarbonylamino group, an alkylcarbonylamino group or the like, R.sup.2 is a hydrogen atom, an alkyl group, a carboxyl group or an alkoxycarbonyl group, R.sup.19 is a hydrogen atom, a halogen atom, a cyano group or the like, Q is a phenyl group which may be substituted or a condensed hetero ring which may be substituted}, a herbicide containing it and an intermediate for its production, are provided.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: April 11, 2000
    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: 5994572
    Abstract: The present invention provides a process for producing 1-alkoxy-1-trimethylsilyloxycyclopropane represented by the following general formula: ##STR1## by reacting microgranular metallic sodium dispersed in a hydrocarbon solvent, .beta.-halogenocarboxylic acid ester represented by the following general formula: ##STR2## and chlorotrimethylsilane. According to the present invention, by using no ether compound solvent (the ether compound solvent has various problems in safety) and using microgranular metallic sodium dispersed in a hydrocarbon solvent, 1-alkoxy-1-trimethylsilyloxycyclopropane can be industrially produced simply (no special apparatus is required) at an advantageous cost at a yield at least equal to that obtained when an ether is used as solvent.
    Type: Grant
    Filed: July 29, 1998
    Date of Patent: November 30, 1999
    Assignee: Ihara Chemical Industry Co., Ltd
    Inventor: Yasuo Yoshida
  • Patent number: 5883285
    Abstract: The present invention provides:a process for producing an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR1## which process comprises reacting a disulfide compound represented by general formula: ##STR2## with a hydroxide of an alkali metal M.sup.1 in the presence of a sulfur compound represented by general formula (2):H.sub.(2-i) S(M.sup.1).sub.i (2)a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR3## which process comprises reacting the above-mentioned alkalimetal salt of an arylmercaptan compound with a halogenofattyacid ester compound represented by general formula (4):X.sup.1 R.sup.2 COOR.sup.3 (4)at pH 7-10; and a process for producing the above-mentioned alkoxycarbonylalkylthioaryl compound, which process comprises reacting the above-mentioned disulfide compound with the above-mentioned hydroxide of an alkali metal M.sup.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: March 16, 1999
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Tatsuo Sugiyama, Tadashi Nakayama
  • Patent number: 5877120
    Abstract: A nicotinic acid derivative represented by general formula (I) or (II), a salt thereof, and a herbicide containing the same as the active ingredient, wherein A represents substituted phenyl, or 5- or 6- membered heterocycle, e.g., thienyl or pyridyl; R represents hydroxy, optionally substituted alkoxy or optionally substituted benzyloxy; R.sup.1 and R.sup.2 represent each independently alkoxy or halogen; R.sup.3 and R.sup.4 represent each independently hydrogen, hydroxy, cyano or alkoxycarbonyl, or they may be combined together to represent oxygen; X represents halogen, alkyl or alkoxy; n represents 0, 1 or 2; and Z represents methine or nitrogen. The compound and salts thereof can control annual or perennial weed growing on the land where various crops such as rice plant, wheat, cotton and corn grow for a wide period ranging from the pre-emergence to growth in a remarkably small dose.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: March 2, 1999
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Miyazaki, Sumio Yokota, Yoshihiro Ito, Nobuyuki Ohba, Nobuhide Wada, Shigehiko Tachikawa, Takeshige Miyazawa
  • Patent number: 5811424
    Abstract: The present invention provides an amino-acid amide 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), R.sup.2 represents an ethyl group, R.sup.3 represents a hydrogen atom, 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, 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), and an agricultural or horticultural fungicide including an effective amount of the same. The amino-acid amide derivatives exhibit a superior control of plant diseases, particularly downy mildew and late blight, and are not harmful to plants.
    Type: Grant
    Filed: July 1, 1996
    Date of Patent: September 22, 1998
    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: 5789428
    Abstract: The present invention provides an amino-acid amide derivative represented by the formula: ##STR1## (wherein R.sup.1 represents a C1.about.C6 alkyl group, a C3.about.C8 cycloalkyl group, or a phenyl group, R.sup.2 represents a hydrogen atom or a methyl group, X represents a halogen atom, a methyl group, a methoxy group, Y represents a C1.about.C6 alkyl group, A represents an oxygen atom, or a sulfur atom, and n represents 0 or an integer from 1 to 3), an agricultural or horticultural fungicide including an effective amount of the same, and a method for killing agriculturally or horticulturally harmful fungi which comprises a step of using a fungicidally effective amount of the amino-acid amide derivative. The present invention provides the amino-acid amide derivatives, which exhibit superior control of plant diseases such as late blight and downy mildew, and which are not harmful chemicals.
    Type: Grant
    Filed: February 3, 1997
    Date of Patent: August 4, 1998
    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: 5770544
    Abstract: A condensed heterocyclic derivative of the formula ##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: October 9, 1996
    Date of Patent: June 23, 1998
    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: 5763616
    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 7, 1997
    Date of Patent: June 9, 1998
    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: 5763463
    Abstract: A pyridine derivative of the formula (I), or its oxide or salt: ##STR1## wherein R.sup.1 is a halogen atom, an alkyl group, etc., R.sup.2 is an alkenyl group, an alkynyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group, etc., R.sup.3 is a hydrogen atom, etc., R.sup.4 is a halogen atom, a cyano group, a haloalkyl group, etc., each of R.sup.5 and R.sup.6 is a hydrogen atom, etc., Q is a methine group or a nitrogen atom, m is 0 or 1, n is 1 or 2 and r is 1 or 2. Such a compound is useful as a pesticide. The compound of the present invention is a pyridine derivative which is capable of killing or controlling various pests without adversely affecting crop plants and which is readily decomposable and presents no substantial acute toxity to mammals.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: June 9, 1998
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuo Takefuji, Masao Nakatani, Junko Suzuki, Masami Ozaki, Ryouhei Ueno, Hiroyuki Yano, Mieko Kawashima, Yutaka Kurihara, Tomonori Shimazu
  • Patent number: 5750763
    Abstract: The present invention provides:a process for producing an alkali metal salt of an arylmercaptan compound, represented by general formula (3): ##STR1## which process comprises reacting a disulfide compound represented by general formula: ##STR2## with a hydroxide of an alkali metal M.sup.1 in the presence of a sulfur compound represented by general formula (2):H.sub.(2-i) S(M.sup.1).sub.i (2)a process for producing an alkoxycarbonylalkylthioaryl compound represented by general formula (5): ##STR3## which process comprises reacting the above-mentioned alkalimetal salt of an arylmercaptan compound with a halogenofattyacid ester compound represented by general formula (4):X.sup.1 R.sup.2 COOR.sup.3 (4)at pH 7-10; anda process for producing the above-mentioned alkoxycarbonylalkylthioaryl compound, which process comprises reacting the above-mentioned disulfide compound with the above-mentioned hydroxide of an alkali metal M.sup.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: May 12, 1998
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Tatsuo Sugiyama, Tadashi Nakayama
  • Patent number: 5739329
    Abstract: The present invention provides a process for producing a hexahydropyridazine-1,2-dicarboxy derivative represented by the general formula: ##STR1## wherein R.sup.1 and R.sup.2 represent each independently an alkyl group, by reacting a hydrazinedicarboxy derivative represented by the general formula:R.sup.1 OOC--NH--NH--COOR.sup.2 (1)wherein R.sup.1 and R.sup.2 have the same meaning as mentioned above, with a dihalogenobutane represented by the general formula:X.sup.1 --CH.sub. CH.sub.2 CH.sub.2 CH.sub.2 --X.sup.2 (2)wherein X.sup.1 and X.sup.2 represent each independently a halogen atom, in the presence of an alkali metal hydroxide, characterized in that the above reaction is effected in an aprotic polar solvent, and a process for producing a hexahydropyridazine, characterized by decarboxylating the thus obtained hexahydropyridazine-1,2-dicarboxy derivative (3) without isolation in the presence of an alkali metal hydroxide and a hydrogen-denoting compound.
    Type: Grant
    Filed: October 5, 1995
    Date of Patent: April 14, 1998
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Tatsuo Sugiyama
  • Patent number: 5728699
    Abstract: The present invention presents a benzylsulfide derivative of the formula (I) or its salt: ##STR1## wherein R.sup.1 is a C.sub.1-6 alkyl group, a C.sub.1-6 haloalkyl group, a C.sub.2-4 alkenyl group, a cyano group, etc., and each of R.sup.2 and R.sup.3 is a hydrogen atom, a halogen atom, a cyano group, a C.sub.1-4 alkyl group, a C.sub.1-3 haloalkyl group, etc., R.sup.4 is a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, etc., A is a hydrazinoaralkyl group or hydrazonoaralkyl group, and n is 0, 1 or 2; a process for its production; and a pesticide containing such a benzylsulfide derivative as an active ingredient. The benzylsulfide derivative of the present invention is capable of controlling various pests without adversely affecting crop plants.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: March 17, 1998
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Keiji Toriyabe, Hideharu Sasaki, Naoshi Masuyama, Akihide Nagai, Hiroyuki Yano, Mieko Kawashima, Yutaka Kurihara, Tomonori Shimazu
  • Patent number: 5723469
    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: July 11, 1996
    Date of Patent: March 3, 1998
    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: 5710346
    Abstract: The present invention provides a 2,2-bis(3,5-disubstituted-4-hydroxyphenyl) propane derivative represented by general formula (1) ##STR1## wherein each R.sup.1 represents a hydrogen atom or a lower alkyl group; a process for producing such propane derivative; and a process for producing pyrogallol using such propane derivative. The compound of the present invention has by itself a periphyton-controlling activity required for the active ingredient used in a periphyton-controlling agent such as antifouling paint for ship's bottom, antifouling agent for fishing net, or the like. Further, by decomposing the above compound with an alkali or an acid, pyrogallol can be produced industrially without using any natural material.
    Type: Grant
    Filed: June 15, 1995
    Date of Patent: January 20, 1998
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Masakazu Takahashi, Tomonori Miyazaki, Chika Maejima, Yoshikazu Kimura
  • Patent number: 5700824
    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: November 6, 1996
    Date of Patent: December 23, 1997
    Assignees: Kumiai Chemical Industrial Co. Ltd., Ihara Chemical Industry Co. Ltd.
    Inventors: Atsuhiko Ikeda, Masami Ozaki, Reijiro Honami, Takashi Yumita, Hiroyuki Yano, Yuki Nakano, Yutaka Kurihara, Tadayoshi Hirano
  • Patent number: 5675012
    Abstract: The present invention provides a process for producing a cyanopyridine represented by general formula (3) ##STR1## (wherein R is a hydrogen atom or a halogen atom; X.sup.1 and X.sup.2 are each a hydrogen atom or a halogen atom with a proviso that at least either of X.sup.1 and X.sup.2 is a halogen atom; n is an integer of 1 or 2), which process comprises reacting an ammonium halide with a trichloromethylpyridine represented by general formula (1) ##STR2## (wherein R, X.sup.1, X.sup.2 and n have the same definitions as given above) in the presence of a metal compound represented by general formula (2)MXm (2)(wherein M is a copper atom or a zinc atom; X is a halogen atom or an oxygen atom; m is an integer of 2 or 1).
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: October 7, 1997
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Hideo Ohi
  • Patent number: 5670452
    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: April 9, 1996
    Date of Patent: September 23, 1997
    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: 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