Patents Assigned to Kumiai Chemical Industry Co., Ltd.
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Patent number: 4969949Abstract: A pyrimidine derivative of the formula: ##STR1## wherein each of R.sup.1 and R.sup.2 which may be the same or different is an alkyl group, or R.sup.1 and R.sup.2 together with the adjacent carbon atom form a ring.Type: GrantFiled: March 21, 1989Date of Patent: November 13, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Shigematsu, Shoji Kusano, Takayoshi Takehi, Takeshige Miyazawa, Yasufumi Toyokawa
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Patent number: 4968340Abstract: A herbicidal alkanoic acid derivative of the formula: ##STR1## wherein R is ##STR2## wherein R.sup.3 is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkyl group, a cycloalkyl group, an alkylthioalkyl group, a hydroxyalkyl group, a hydroxyl group, a cyano group, an acyloxyalkyl group, a thienyl group, a naphthyl group, a dihydronaphthyl group or ##STR3## wherein R.sup.8 is a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an alkoxy group or --S(O).sub.n R.sup.9 wherein R.sup.9 is an alkyl group, and n is an integer of from 0 to 2, m is an integer of from 0 to 2, each of R.sup.2 and R.sup.4 which may be the same or different is a hydrogen atom or an alkyl group, or R.sup.2 and R.sup.4 form together with the adjacent carbon atom a 3-, 4-, 5- or 6-membered ring which may contain an oxygen atom and may be substituted by one or two alkyl groups, each of R.sup.5 and R.sup.6 which may be the same or different is a hydrogen atom or an alkyl group, R.sup.Type: GrantFiled: June 20, 1989Date of Patent: November 6, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Koichiro Kaku, Nobuhide Wada, Akira Takeuchi, Yasufumi Toyokawa, Takeshige Miyazawa, Ryo Yoshida, Kazuhiko Sugiyama
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Patent number: 4957935Abstract: A phenyltriazole compound having the formula: ##STR1## wherein X is a lower alkyl group having all or a part of hydrogen atoms substituted by fluorine atoms, and each of R.sup.1 and R.sup.2 which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.1 and R.sup.2 form together with the adjacent nitrogen atom a pyrrole ring or an ethoxymethylideneamino group.Type: GrantFiled: June 13, 1989Date of Patent: September 18, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahito Inamori, Tetsuo Horii, Tomonori Shimazu, Masaji Sugaya
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Patent number: 4954157Abstract: A plant growth regulating composition comprising a member selected from the group consisting of 3,5-dioxo-4-propionylcyclohexane carboxylic acid and its esters and salts, represented by the formula: ##STR1## wherein R is a hydrogen atom, a lower alkyl group or a cation, and at least one compound selected from the group consisting of (2-chloroethyl) phosphonic acid, 1,1-dimethylpiperidinium chloride and 2-chloroethyltrimethylammonium chloride, as active ingredients, and an agricultural carrier or diluent.Type: GrantFiled: May 18, 1989Date of Patent: September 4, 1990Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Takeshige Miyazawa, Kazuhiko Kawano
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Patent number: 4946495Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein X is a halogen atom or ##STR2## wherein X.sup.1 is a halogen atom, a lower alkyl group or a lower alkoxy group and k is 0, 1 or 2; R.sup.1 is a hydrogen atom, a benzyl group, --(CH.sub.2).sub.m R.sup.3 wherein R.sup.3 is a cyano group, a formyl group, a dialkylamino group, a phenyl group, a pyridyl group, a trimethylsilyl group, a naphthyl group, an alkoxycarbonyl group, a benzoyl group, an alkylthio group, a phenylthio group, an alkylsulfonyl group or a benzyloxy group and m is 1, 2 or 3, or ##STR3## wherein R.sup.4 is a hydrogen atom or a lower alkyl group, R.sup.5 is a lower alkyl group or ##STR4## wherein X.sup.2 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a nitro group, n is 0 or 1, provided that when R.sup.5 is an alkyl group, n is 1; and R.sup.2 is a chlorine atom or a methoxy group, provided that when R.sup.1 is a hydrogen atom or a benzyl group, X is ##STR5## and R.sup.Type: GrantFiled: April 13, 1988Date of Patent: August 7, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi, Takayoshi Takehi
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Patent number: 4939166Abstract: Described are KSB-1939 compounds represented by the following general formula (I): ##STR1## wherein R means ##STR2## in which n stands for an integer of 0-2 and m denotes an integer of 0 or 1, and R' denotes a methyl or ethyl group. A production process of the KSB-1939 compounds and pesticidal agents comprising, as an effective ingredient, one of the KSB-1939 compounds are also described.Type: GrantFiled: July 7, 1988Date of Patent: July 3, 1990Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Hideki Katoh, Reisuke Kobayashi, Tomonori Shimazu, Akinori Suzuki, Akira Isogai, Osamu Tada
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Patent number: 4932999Abstract: A pyrimidine compound having the formula: ##STR1## wherein X is a halogen atom, or a salt thereof.Type: GrantFiled: October 2, 1989Date of Patent: June 12, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Yoshihiro Saito, Nobuhide Wada, Shoji Kusano, Takeshige Miyazawa, Satoru Takahashi, Yasuhumi Toyokawa, Ikuo Kajiwara
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Patent number: 4931087Abstract: A picolinic acid derivative having the formula: ##STR1## wherein R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkali metal atom, an alkaline earth metal atom, an alkylammonium group or ##STR2## [wherein R.sup.11 is a hydrogen atom or an alkyl group, R.sup.12 is an alkoxycarbonyl group, a cyano group, a halogen atom, an acetyl group, a pivaloyl group, a benzoyl group, an alkoxy group, a phenoxy group, a halogenoacetyloxy group, a methylsulfonyloxy group, a hydroxyl group, an alkylthio group, an alkylsulfonyl group, a phenylthio group, a dialkylamino group, a naphthyl group, a pyridyl group, ##STR3## (wherein W is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenoxy group, a nitro group or an alkoxycarbonyl group, and e is 1 or 2) or ##STR4## (wherein each of R.sup.3 and R.sup.4 which may be the same or different, is a hydrogen atom, an alkyl group, an alkenyl group or a phenyl group), and m is an integer of from 0 to 2], each of R.sup.1 and R.sup.Type: GrantFiled: January 12, 1989Date of Patent: June 5, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Shigematsu, Hideo Ohi, Shoji Kusano, Takeshige Miyazawa, Satoru Takahashi, Yasuhumi Toyokawa, Ikuo Kajiwara
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Patent number: 4927448Abstract: A thiadiazabicyclononane derivative having the formula: ##STR1## wherein X is hydrogen or halogen, R.sup.1 is hydrogen or alkyl, R.sup.2 is alkenyloxy, alkynyloxy, alkylthio, halogen-substituted alkoxy, alkoxycarbonylalkoxy, .alpha.,.alpha.-dimethylbenzylamino, --OC.sub.2 H.sub.4 S(O).sub.l R.sup.3 (wherein R.sup.3 is alkyl or phenyl, and l is an integer of 0 or 2), ##STR2## (wherein Y is halogen, alkyl, alkoxy or nitro, R.sup.4 is hydrogen or alkyl, and each of m and n is an integer of 0, 1 or 2), --OC.sub.2 H.sub.4 OR.sup.5 (wherein R.sup.5 is phenyl, benzyl or methoxyalkyl), --OCH.sub.2 R.sup.6 (wherein R.sup.6 is styryl, cyanoalkyl, tetrahydrofuran-2-yl, thienyl or pyridin-2-yl), ##STR3## (wherein R.sup.Type: GrantFiled: October 14, 1988Date of Patent: May 22, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Mikio Yamaguchi, Chiharu Suzuki, Kenji Matsunari, Takeshige Miyazawa, Yasuo Nakamura
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Patent number: 4925864Abstract: A phenyltriazole derivative of the formula: ##STR1## wherein X is a halogen atom, an alkyl group, a halogen-substituted alkyl group, an alkoxy group, a nitro group, a phenoxy group, an amino group, a cyano group, a 1-pyrrolyl group or a halogen-substituted alkoxy group, Y is a C.sub.2 -C.sub.6 alkyl group which may be substituted by halogen, alkoxy, alkylthio, alkylsulfonyl, alkoxycarbonyl or carbamoyl, a methyl-substituted cycloalkyl group, an alkenyl group, a C.sub.1 -C.sub.4 alkylsulfinyl group or a 2-methyl-1,3-dithiolan-2-yl group, Z is a hydrogen atom, a halogen atom, a halogen-substituted alkyl group, an alkoxyalkyl group, an alkenyloxyalkyl group, a methyl group, an alkylsulfinyl group, an alkylsulfonyl group, a phenyl group, a ##STR2## group, wherein each of R.sup.1 and R.sup.Type: GrantFiled: March 22, 1988Date of Patent: May 15, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahito Inamori, Tetsuo Horii, Tomonori Shimazu, Masaji Sugaya
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Patent number: 4923501Abstract: A pyrimidine derivative having the formula: ##STR1## wherein X is a halogen atom, a lower alkyl group or a phenoxy group (wherein said phenoxy group may be substituted by halogen, lower alkyl or lower alkoxy), and R is a hydrogen atom, a lower alkyl group, an alkoxyalkyl group, a benzyloxyalkyl group, an alkoxycarbonyl alkyl group, a cyanoalkyl group or a ##STR2## group (wherein R.sup.1 is a hydrogen atom or a lower alkyl group, and R.sup.2 is a lower alkyl group or a phenyl group which may be substituted by nitro), or a salt thereof.Type: GrantFiled: October 28, 1988Date of Patent: May 8, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Company, Ltd.Inventors: Yoshihiro Saito, Nobuhide Wada, Shoji Kusano, Takeshige Miyazawa, Satoru Takahashi, Yasuhumi Toyokawa, Ikuo Kajiwaca
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Patent number: 4906285Abstract: A pyrimidine derivative having the formula: ##STR1## wherein R is hydrogen atom, --CH.sub.2 CH.sub.2 S(O).sub.n R.sub.1 (wherein R.sub.1 is a lower alkyl group, and n is an integer of from 0 to 2) or ##STR2## (wherein each R.sub.1 is a lower alkyl group), A is a chlorine atom or a methoxy group, and each of D and E which may be the same or different, is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a halogen-substituted lower alkoxy group, or a salt thereof.Type: GrantFiled: December 21, 1988Date of Patent: March 6, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Shoji Kusano, Yasuhumi Toyokawa
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Patent number: 4900352Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein R.sup.1 is a formyl group, a dimethoxymethyl group or --COOR.sup.4 (wherein R.sup.4 is a hydrogen atom, a lower alkyl group, a benzyl group, an alkali metal atom, an alkaline earth metal atom or an organic ammonium group), R.sup.2 is a chlorine atom, a methyl group, a methoxy group or a difluoromethoxy group, R.sup.3 is a methyl group or a methoxy group, X is a halogen atom, a lower alkyl group, a lower alkoxy group, an amino group, a hydroxyl group, a nitro group or a cyano group, and n is 1 or 2.Type: GrantFiled: December 29, 1988Date of Patent: February 13, 1990Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasuhumi Toyokawa, Takeshige Miyazawa, Ikuo Kajiwara, Satoru Takahashi
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Patent number: 4889552Abstract: A 2-phenoxypyrimidine derivative having the formula: ##STR1## wherein R is a formyl group or --COOR.sup.1 wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a 2-methylsulfonylethyl group, a diethoxypropyl group, a lower alkenyl group, a lower alkynyl group, a haloalkyl group, a haloalkenyl group, an alkoxyalkyl group, a hydroxyalkyl group, a cycloalkyl group, a phenyl group or ##STR2## wherein Y is a halogen atom, a methyl group or a methoxy group and n is 0, 1 or 2; and X is a halogen atom, an alkynyloxy group, an alkenyloxy group, an alkylthio group, an alkoxyalkyloxy group, a haloalkoxy group, an acetyloxy group, a benzoyloxy group, a formyl group, a trifluoromethyl group, a carboxyl group, an alkoxycarbonyl group, a dialkylamino group, a dimethoxymethyl group, ##STR3## wherein R.sup.2 is a hydrogen atom or a methyl group, Z is a chlorine atom or an alkyl group and m is 0, 1 or 2, or ##STR4## wherein R.sup.Type: GrantFiled: April 13, 1988Date of Patent: December 26, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi
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Patent number: 4885023Abstract: As a herbicide, a 9-phenylimino-8-thia-1,6-diazabicyclo [4.3.0]nonane-7-one derivative having the formula: ##STR1## wherein each of X and Y is hydrogen or halogen, and Z is ##STR2## wherein R.sup.1 is alkyl or cycloalkyl, or --COOR.sup.2 wherein R.sup.2 is alkyl.Type: GrantFiled: December 22, 1987Date of Patent: December 5, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Mikio Yamaguchi, Yukihiro Watase, Takeshi Kambe, Susumu Katou
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Patent number: 4866201Abstract: A new compound is provided by a cyclohexane derivative of the formula ##STR1## wherein R represents a hydrogen atom or an alkyl group, an alkylthioalkyl group or an unsubstituted or substituted phenyl group; and R.sup.1 represents an alkyl group, an unsubstituted or substituted benzyl group, a phenethyl group, a phenoxymethyl group, a 2-thienylmethyl group, an alkoxymethyl group or an alkylthiomethyl group, or a salt of said cyclohexane compound.This cyclohexane compound exhibits useful plant-growth regulating effects on crop-plants and also non-crop plants such as lawn and may be prepared by cyclization of an acetonylsuccinic acid dialkyl ester, followed by reaction with an organic acid chloride and by intermolecular rearrangement.Type: GrantFiled: July 7, 1987Date of Patent: September 12, 1989Assignee: Kumiai Chemical Industry Co., Ltd.Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
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Patent number: 4866064Abstract: A class of novel 5H-1,3,4-thiadizaolo[3,2-a]pyrimidin-5-one derivatives are disclosed. These compounds exhibit remarkable fungicidal activities for pathogenic fungi of cucumber gray mold, cucumber downy mildew, Alternaria sooty spot of Chinese mustard, apple Alternaria leaf spot, pear black spot, rice blast, tomato late blight, etc.Type: GrantFiled: September 14, 1987Date of Patent: September 12, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Yukio Tokunaga, Yoshiyuki Kojima, Shinichiro Maeno, Nobumitsu Sawai, Yasuo Saso
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Patent number: 4832729Abstract: A picolinic acid derivative having the formula: ##STR1## wherein R is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkali metal atom, an alkaline earth metal atom, an alkylammonium group or ##STR2## [wherein R.sup.11 is a hydrogen atom or an alkyl group, R.sup.12 is an alkoxycarbonyl group, a cyano group, a halogen atom, an acetyl group, a pivaloyl group, a benzoyl group, an alkoxy group, a phenoxy group, a halogenoacetyloxy group, a methylsulfonyloxy group, a hydroxyl group, an alkylthio group, an alkylsulfonyl group, a phenylthio group, a dialkylamino group, a naphthyl group, a pyridyl group, ##STR3## (wherein W is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a phenoxy group, a nitro group or an alkoxycarbonyl group, and e is 1 or 2) or ##STR4## (wherein each of R.sup.3 and R.sup.4 which may be the same or different, is a hydrogen atom, an alkyl group, an alkenyl group or a phenyl group), and m is an integer of from 0 to 2], each of R.sup.1 and R.sup.Type: GrantFiled: April 13, 1987Date of Patent: May 23, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Masahiro Shigematsu, Hideo Ohi, Shoji Kusano, Takeshige Miyazawa, Satoru Takahashi, Yasuhumi Toyokawa, Ikuo Kajiwara
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Patent number: 4824477Abstract: A trifluoromethanesulfonanilide compound having the formula: ##STR1## wherein Y is a (1-cyano-2-propyl)cyclopropyl group or a (1-cyano)cyclopentyl group.Type: GrantFiled: February 26, 1987Date of Patent: April 25, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Tetsuo Takematsu, Makoto Konnai, Kuniaki Shimizu, Ikumi Urushibata, Ikuo Kajiwara
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Patent number: 4816063Abstract: As a herbicide 9-phenylimino-8-thia-1,6-diazabicyclo[4.3.0]nonane-7-(one or thione) compound having the formula: ##STR1## wherein Y represents halogen, hydroxyl, alkyl, alkoxy which may be substituted by halogen, alkenyloxy, alkynyloxy, phenoxy, cycloalkyloxy, alkoxycarbonylalkyloxy alkoxycarbonylalkenyloxy, alkythiocarbonylalkyloxy, alkynyloxycarbonylalkyloxy, benzyloxycarbonylalkyloxy, trifluoromethyl, benzyloxy, alkenyl, cyanoalkyl, alkylcarbamoyloxy, benzyl, alkoxyalkyl, alkynyloxyalkyl, cycloalkylmethyloxy, alkoxyalkyloxy, phenethyloxy, cycloalkyloxycarbonylalkyloxy, pyrrolidinocarbonyl, phenylcarbonyl, ##STR2## n is an integer of from 0 to 3; and X is oxygen or sulfur.Type: GrantFiled: September 24, 1986Date of Patent: March 28, 1989Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Mikio Yamaguchi, Yukihiro Watase, Takeshi Kambe, Susumu Katou