Patents Assigned to Kumiai Chemical Industry Co., Ltd.
  • 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
  • Patent number: 6090815
    Abstract: The present invention provides a pyrimidinyloxyalkanamide derivative represented by Formula (I): ##STR1## (wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, or the like, R.sup.2 represents a C.sub.1 -C.sub.6 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, or the like, R.sup.3 represents a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a halogen atom, or the like, R.sup.4 represents a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, or the like, Q represents a cyano group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, or the like, and A represents an oxygen atom or a sulfur atom) and a novel agricultural or horticultural fungicide including the same as an active ingredient.The agricultural or horticultural fungicides according to the present invention have excellent controlling effects with regard to rice blast, which are apparently excellent controlling effects as compared with the known compounds.
    Type: Grant
    Filed: April 30, 1999
    Date of Patent: July 18, 2000
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Katsumi Masuda, Ikumi Urushibata, Tsuyoshi Asahara, Katsumi Furuse, Yoshiyuki Kojima, Norimichi Muramatsu
  • 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: 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: 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: 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: 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: 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: 5576269
    Abstract: A composition comprising a condensed heterocyclic derivative and an N-alkyl-2-pyrrolidone and another organic solvent for enhanced stability. Particularly high effects can be obtained with a composition wherein the ratio of the condensed heterocyclic derivative to the N-alkyl-2-pyrrolidone is within a range of from 2:1 to 1:1000.
    Type: Grant
    Filed: August 11, 1995
    Date of Patent: November 19, 1996
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Yoshinori Hirabayashi, Shigeki Fujita, Kanji Nakamura, Susumu Kato
  • 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: 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