Patents Assigned to Kumiai Chemical Industry Co., Ltd.
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Patent number: 5510321Abstract: A plant growth regulator composition comprising a cyclohexane derivative of the formula: ##STR1## wherein R is a hydrogen atom, a lower alkyl group, an alkylthioalkyl group, a phenyl group or a substituted phenyl group, and R.sup.1 is a lower alkyl group, a cycloalkyl group, a benzyl group, a substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt thereof, and a nitrogen-containing water-soluble inorganic substance or urea.Type: GrantFiled: February 9, 1995Date of Patent: April 23, 1996Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Yoshinori Hirabayashi, Toshihiro Ikeuchi, Susumu Kato, Takeshige Miyazawa, Kanji Nakamuras
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Patent number: 5482951Abstract: 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: GrantFiled: December 23, 1993Date of Patent: January 9, 1996Assignees: 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
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Patent number: 5478799Abstract: 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: GrantFiled: May 18, 1995Date of Patent: December 26, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihisa Yonekura, Junetsu Sakai, Shigeru Hayashi
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Patent number: 5466705Abstract: 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: GrantFiled: January 21, 1994Date of Patent: November 14, 1995Assignees: 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
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Patent number: 5444060Abstract: 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: GrantFiled: November 2, 1993Date of Patent: August 22, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Ikumi Urushibata, Takumi Yoshimura, Takeshi Deguchi, Norihasa Yonekura, Junetsu Sakai, Shigeru Hayashi
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Patent number: 5436225Abstract: A plant growth regulator composition comprising a cyclohexane derivative of the formula: ##STR1## wherein R is a hydrogen atom, a lower alkyl group, an alkylthioalkyl group, a phenyl group or a substituted phenyl group, and R.sup.1 is a lower alkyl group, a cycloalkyl group, a benzyl group, a substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt thereof, and a nitrogen-containing water-soluble inorganic substance or urea.Type: GrantFiled: November 16, 1993Date of Patent: July 25, 1995Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Yoshinori Hirabayashi, Toshihiro Ikeuchi, Susumu Kato, Takeshige Miyazawa, Kanji Nakamura
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Patent number: 5418212Abstract: 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: GrantFiled: April 27, 1993Date of Patent: May 23, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
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Patent number: 5411934Abstract: 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: GrantFiled: July 30, 1992Date of Patent: May 2, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Takumi Yoshimura, Keiji Toriyabe, Katsumi Masuda, Ryo Hanai
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Patent number: 5403816Abstract: 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: GrantFiled: April 20, 1993Date of Patent: April 4, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Fumiaki Takabe, Yoshihiro Saito, Masatoshi Tamaru, Shigehiko Tachikawa, Ryo Hanai
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Patent number: 5401711Abstract: 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: GrantFiled: February 1, 1993Date of Patent: March 28, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Sato, Koichiro Kaku, Shigehiko Tachikawa
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Patent number: 5395819Abstract: Stable herbicide solutions of propanil having no or little tendency to precipitate or crystallize propanil from the solution even upon storage in a cold place are prepared by dissolving the propanil in (a) a solvent of the glycol ether-type having a solubility of not more than 5% by weight in water at 20.degree. C. and (b) dimethylsulfoxide or (c) N-methyl-2-pyrrolidone, and wherein propanil is present in an amount of 20 to 45% by weight, the glycol ether-type solvent is present in an amount of 35 to 85% by weight, and the dimethylsulfoxide or N-methyl-2-pyrrolidone is present in an amount of 1 to 20% by weight, on the basis of the total weight of the composition.Type: GrantFiled: August 17, 1993Date of Patent: March 7, 1995Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Shigeki Fujita, Kanji Nakamura
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Patent number: 5391537Abstract: The present invention is to provide a novel picolinic acid derivative having the formula, ##STR1## (wherein R is a hydrogen atom, an alkyl group or others, R.sup.1 and R.sup.2 are the same or different, and are an alkyl group, an alkoxy group or others, X is a cyano group, a phenoxy group or others, Y is an oxygen atom or others, and n is 0 or 1) or a salt thereof; a method for preparing the same; and a herbicidal composition containing the same as an active ingredient.The picolinic acid derivative or the salt thereof of the present invention achieves an excellent herbicidal effect at a low dosage, and is effective for controlling the growth of various weeds in a wide range.The picolinic acid derivative or the salt thereof of the present invention can be applied to a paddy field, a cultivated field, a non-agricultural land and the like as a herbicidal composition.Type: GrantFiled: October 14, 1992Date of Patent: February 21, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Fumiaki Takabe, Yoshihiro Saito, Masatoshi Tamaru, Shigehiko Tachikawa, Ryo Hanai
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Patent number: 5385880Abstract: Herbicidal composition containing a compound having the following formula or its salt: ##STR1## wherein W is an oxygen atom, a sulfur atom, a NH group or a group of the formula, >NC(O)B;Z is a methine group or a nitrogen group;X is a phenyl group which may be substituted or a group having the formula: ##STR2## and n is an integer of from 1 to 3.Type: GrantFiled: September 17, 1992Date of Patent: January 31, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Miyazaki, Masafumi Matsuzawa, Keiji Toriyabe, Michiya Hirata
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Patent number: 5380944Abstract: A novel benzhydrazone derivative has a general formula [I]: ##STR1## (wherein R.sup.1 is a lower alkyl group, R.sup.2 and R.sup.3 are same or different halogen atoms and Z is a chlorine atom or an amino group) and is useful as an intermediate for the production of a triazole derivative having the following general formula [II]: ##STR2## (wherein R.sup.1, R.sup.2 and R.sup.3 are the same as mentioned above and X is a chlorine atom located at 2- or 6-position).Type: GrantFiled: October 27, 1993Date of Patent: January 10, 1995Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masami Ozaki, Reijiro Honami, Takashi Yumita, Atsuhiko Ikeda, Naokazu Minoguchi, Norihiko Izawa, Tadayoshi Hirano
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Patent number: 5380700Abstract: The present invention provides a novel pyridine derivative having the following general formula and its salt: ##STR1## wherein R is a hydrogen atom, a hydroxyl group, an alkoxy group, an alkoxyalkoxy group, and derivatives;R.sup.1 and R.sup.2 may be the same or different, and are a hydrogen atom, an alkoxy group, a halogen atom, an alkylamino group, a dialkylamino group;Z is a methine group or a nitrogen atom;X.sup.1 is an acylamino group, a cycloalkyl group, a halogen-substituted alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxycarbonyl group, an alkylamino group, a dialkylamino group, a phenyl group.The pyridine derivative and its salt of the present invention achieve an excellent herbicidal effect on annual and perennial weeds growing in paddy fields and upland fields at a very small dosage.The pyridine derivative and its salt of the present invention have safety to rice, wheat, cotton and corn, and can be suitably applied as a herbicide to a field where these plants are cultivated.Type: GrantFiled: December 23, 1992Date of Patent: January 10, 1995Assignees: Kumiai Chemical Industries Co., Ltd., Ihara Chemical Industries Co., Ltd.Inventors: Masahiro Miyazaki, Masafumi Matsuzawa, Keiji Toriyabe, Michiya Hirata
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Patent number: 5366988Abstract: The present invention provides benzohydroximoylazole derivatives represented by the following novel formula: ##STR1## wherein R is a branched alkyl group having not fewer than 5 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: GrantFiled: July 28, 1992Date of Patent: November 22, 1994Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Keiji Toriyabe, Takayoshi Takehi, Yukio Nezu, Yuki Nakano, Tomonori Shimazu
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Patent number: 5318959Abstract: 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, an alkyl group or the like, n is an integer of 1-5, Y is an alkenyl group, an alkynyl group, an alkoxyalkyl group or the like) and controls various injurious insects and mites, particularly mites and aphids without damaging crops.Type: GrantFiled: October 6, 1992Date of Patent: June 7, 1994Assignees: 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
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Patent number: 5312929Abstract: A herbicidal 2-oxo-3-pyrroline derivative having the formula: ##STR1## wherein X is a hydrogen atom or a halogen atom, Z is an oxygen atom or a group of the formula .dbd.N--OR.sup.1 (wherein R.sup.1 is a hydrogen atom, an alkyl group, a benzyl group or a phenyl group which is substituted by halogen atoms); and R is a hydrogen atom, an alkyl group, a benzyl group, a chloro-substituted benzyl group, a benzylidene methyl group, a group of the formula ##STR2## wherein Y is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group or an alkoxy group, and n is an integer of from 1 to 3, or a group of the formula ER.sup.2 wherein E is an oxygen atom, a sulfur atom or a group of the formula >N--R.sup.3, wherein R.sup.3 is a hydrogen atom, an alkyl group or an alkenyl group, and R.sup.Type: GrantFiled: December 23, 1992Date of Patent: May 17, 1994Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuyuki Ohba, Toshihiro Nagata, Akira Takeuchi, Shigehiko Tachikawa, Yasunori Ogawa
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Patent number: 5284860Abstract: A novel triazole derivative for use in an insecticide has a general formula [I]: ##STR1## (wherein R.sup.1 is a lower alkyl group, R.sup.2 and R.sup.3 are same or different halogen atoms and X is a chlorine atom located at 2- or 6-position) and controls various injurious insects, particularly aphids without damaging crops.Type: GrantFiled: October 6, 1992Date of Patent: February 8, 1994Assignees: Kumiai Chemical Industry Co. Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masami Ozaki, Reijiro Honami, Takashi Yumita, Atsuhiko Ikeda, Naokazu Minoguchi, Norihiko Izawa, Tadayoshi Hirano
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Patent number: 5273955Abstract: A herbicide composition containing propanil as active ingredient is now provided in the form of emulsifiable concentrated organic solution of propanil and surface-active agent(s) in non-toxic mixed organic solvents, which is readily dilutable with water to prepare a stable aqueous emulsion comprising the organic solution of propanil as the disperse phase dispersed in water as the continuous phase of the resulting aqueous emulsion without involving precipitation of propanil solids in said emulsion. Said mixed organic solvents may comprise a mixture of a glycol ether-type solvent with either one or two of dimethyl-sulfoxide and N-methyl-2-pyrrolidone, optionally along with an aromatic solvent. Also, a herbicide composition is provided in the form of a stable solution of propanil in non-toxic mixed organic solvents similar to those mentioned above, which is stable on storage and may be formulated into an emulsifiable concentrated organic solution of propanil by adding surface-active agent(s) thereinto.Type: GrantFiled: February 18, 1992Date of Patent: December 28, 1993Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Shigeki Fujita, Kanji Nakamura