Patents Assigned to Kumiai Chemical Industry Co., Ltd.
  • Patent number: 4969949
    Abstract: 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: Grant
    Filed: March 21, 1989
    Date of Patent: November 13, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahiro Shigematsu, Shoji Kusano, Takayoshi Takehi, Takeshige Miyazawa, Yasufumi Toyokawa
  • Patent number: 4968340
    Abstract: 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: Grant
    Filed: June 20, 1989
    Date of Patent: November 6, 1990
    Assignees: 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
  • Patent number: 4957935
    Abstract: 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: Grant
    Filed: June 13, 1989
    Date of Patent: September 18, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahito Inamori, Tetsuo Horii, Tomonori Shimazu, Masaji Sugaya
  • Patent number: 4954157
    Abstract: 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: Grant
    Filed: May 18, 1989
    Date of Patent: September 4, 1990
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Takeshige Miyazawa, Kazuhiko Kawano
  • Patent number: 4946495
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: August 7, 1990
    Assignees: 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
  • Patent number: 4939166
    Abstract: 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: Grant
    Filed: July 7, 1988
    Date of Patent: July 3, 1990
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Hideki Katoh, Reisuke Kobayashi, Tomonori Shimazu, Akinori Suzuki, Akira Isogai, Osamu Tada
  • Patent number: 4932999
    Abstract: A pyrimidine compound having the formula: ##STR1## wherein X is a halogen atom, or a salt thereof.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: June 12, 1990
    Assignees: 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
  • Patent number: 4931087
    Abstract: 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: Grant
    Filed: January 12, 1989
    Date of Patent: June 5, 1990
    Assignees: 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
  • Patent number: 4927448
    Abstract: 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: Grant
    Filed: October 14, 1988
    Date of Patent: May 22, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Chiharu Suzuki, Kenji Matsunari, Takeshige Miyazawa, Yasuo Nakamura
  • Patent number: 4925864
    Abstract: 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: Grant
    Filed: March 22, 1988
    Date of Patent: May 15, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Masahito Inamori, Tetsuo Horii, Tomonori Shimazu, Masaji Sugaya
  • Patent number: 4923501
    Abstract: 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: Grant
    Filed: October 28, 1988
    Date of Patent: May 8, 1990
    Assignees: 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
  • Patent number: 4906285
    Abstract: 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: Grant
    Filed: December 21, 1988
    Date of Patent: March 6, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Shoji Kusano, Yasuhumi Toyokawa
  • Patent number: 4900352
    Abstract: 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: Grant
    Filed: December 29, 1988
    Date of Patent: February 13, 1990
    Assignees: 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
  • Patent number: 4889552
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: December 26, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Yoshihiro Saito, Shoji Kusano, Yasufumi Toyokawa, Takeshige Miyazawa, Satoru Takahashi
  • Patent number: 4885023
    Abstract: 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: Grant
    Filed: December 22, 1987
    Date of Patent: December 5, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yukihiro Watase, Takeshi Kambe, Susumu Katou
  • Patent number: 4866201
    Abstract: 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: Grant
    Filed: July 7, 1987
    Date of Patent: September 12, 1989
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kenji Motojima, Takeshige Miyazawa, Yasufumi Toyokawa, Masafumi Matsuzawa, Hiroshi Hokari, Shoji Kusano
  • Patent number: 4866064
    Abstract: 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: Grant
    Filed: September 14, 1987
    Date of Patent: September 12, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Yukio Tokunaga, Yoshiyuki Kojima, Shinichiro Maeno, Nobumitsu Sawai, Yasuo Saso
  • Patent number: 4832729
    Abstract: 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: Grant
    Filed: April 13, 1987
    Date of Patent: May 23, 1989
    Assignees: 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
  • Patent number: 4824477
    Abstract: A trifluoromethanesulfonanilide compound having the formula: ##STR1## wherein Y is a (1-cyano-2-propyl)cyclopropyl group or a (1-cyano)cyclopentyl group.
    Type: Grant
    Filed: February 26, 1987
    Date of Patent: April 25, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Tetsuo Takematsu, Makoto Konnai, Kuniaki Shimizu, Ikumi Urushibata, Ikuo Kajiwara
  • Patent number: 4816063
    Abstract: 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: Grant
    Filed: September 24, 1986
    Date of Patent: March 28, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yukihiro Watase, Takeshi Kambe, Susumu Katou