Patents Assigned to Kumiai Chemical Industry Co., Ltd.
  • Patent number: 5235092
    Abstract: A phenoxycetic acid derivative of the formula: ##STR1## wherein R is a hydroxyl group, an alkoxy group, a group of the formula OM wherein M is an alkali metal ion, an alkaline earth metal ion, a transition metal ion, an ammonium ion or an organic ammonium ion, or a group of the formula NHR.sub.1 wherein R.sub.1 is a hydrogen atom, a hydroxyl group, an amino group, an allyloxy group or an ethoxycarboxylmethoxy group.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: August 10, 1993
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Takumi Yoshimura, Tetsuo Takematsu, Makoto Konnai
  • Patent number: 5180416
    Abstract: The present invention discloses a complex suspended herbicide formulation including: a herbicidally active ingredient of thiolcarbamate type which is liquid at common temperature; a solid herbicidally active ingredient which is slightly soluble in the herbicidally active ingredient of thiolcarbamate type at common temperature; a surfactant; and a dry process white carbon; wherein the solid herbicidally active ingredient is dispersed and suspended in the herbicidally active ingredient of thiolcarbamate type in the presence of the surfactant and the dry process white carbon; and wherein the herbicidally active ingredient of thiolcarbamate type is represented by the formula: ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 3 carbon atoms, a phenyl group, or a halogen-substituted phenyl group; R.sup.2 and R.sup.3 are alkyl groups having from 1 to 5 carbon atoms, with the proviso that R.sup.2 and R.sup.3 may form a ring.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: January 19, 1993
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Susumu Katou, Kanji Nakamura
  • Patent number: 5154750
    Abstract: A pyrimidine derivative having the formula, ##STR1## {wherein R.sup.1 is a hydrogen atom or an alkyl group, R.sup.2 is a group having the formula R.sup.3 O (wherein R.sup.3 is an alkoxyalkyl group, an aralkyl group, an alkylcarbonyl group, a phenylcarbonyl group, a substituted phenylcarbonyl group or an alkoxycarbonyl group), a group having the formula ##STR2## wherein R.sup.4 and R.sup.5 may be the same or different and are a hydrogen atom or an alkyl group), a group having the formula ##STR3## (wherein n is 0 or 1), a phthalimide group or a dioxolanylmethyl group, and A and B may be the same or different and are an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an amino group, a monoalkylamino group, a dialkylamino group, a cyano group or a halogen atom}, and a herbicidal composition containing said pyrimidine derivative as an active ingredient.
    Type: Grant
    Filed: August 16, 1991
    Date of Patent: October 13, 1992
    Assignees: Kumiai Chemical Industry Co. Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Ryo Yoshida
  • Patent number: 5114463
    Abstract: A herbicidal pyrimidine derivative having the formula, ##STR1## wherein R is a lower alkyl group, and R.sup.1 is a lower alkoxy group, a halogen atom or a halogen-substituted lower alkoxy group.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: May 19, 1992
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Ryo Yoshida
  • Patent number: 5112385
    Abstract: A substituted aryloxyurea of the formula: ##STR1## wherein Ar represents ##STR2## in which X.sup.7 represents a hydrogen atom, a halogen atom, a cyano group, a lower alkoxy group or a trifluoromethyl group, andR.sup.1 and R.sup.2 together form together with carbon and the nitrogen atom to which they are bonded a 4-8 membered heterocyclic ring.The substituted aryloxyureas exhibit an excellent herbicidal efficacy against weeds when applied, for example, to the weeds in a wide range of period from a preemergence stage to a growth stage.The substituted aryloxyureas of the invention have the excellent advantage of maintaining high safety on crops or crop plants in spite of their herbicidal efficacy.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: May 12, 1992
    Assignees: Kumiai Chemical Industry Co., Ltd., Mitsui Petrochemical Industries, Ltd.
    Inventors: Isao Hashimoto, Tatsuyodihi Ishida, Kazutaka Tsuru, Yuji Yamada, Takeshige Miyazawa, Yasuo Nakamura, Susumu Katou, Katsuya Takahashi
  • Patent number: 5110346
    Abstract: A herbicidal composition comprising (a) 9-(4-chloro-5 -methoxycarbonylmethylthio-2-fluorophenyl)-8-thia-1,6-diazabicyclo[4.3.0]n onan-7-on and (b) 2-[4,5-dihydro-4-methyl-4-(1 -methylethyl)-5-oxo-1H-imidazol-2-yl]-3-quinolinecarboxylic acid, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl-5-oxo-1H-imidazol-2-yl]-5-ethyl-3 -pyridinecarboxylic acid, its ester or its salt, as active ingredients.
    Type: Grant
    Filed: April 17, 1991
    Date of Patent: May 5, 1992
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Takeshige Miyazawa, Kazuhiko Kawano
  • Patent number: 5091311
    Abstract: A method of producing novel macrolides of the formula ##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 using Streptomyces hygroscopicus is described.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: February 25, 1992
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Hideki Katoh, Reisuke Kobayashi, Tomonori Shimazu, Akinori Suzuki, Akira Isogai, Osamu Tada
  • Patent number: 5087289
    Abstract: A herbicidal alkanoic acid derivative of the formula: ##STR1## 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 ##STR2## 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.7 is an alkyl group or a phenyl group, or R.sup.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: February 11, 1992
    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: 5081244
    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 22, 1989
    Date of Patent: January 14, 1992
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuhide Wada, Shoji Kusano, Yasuhumi Toyokawa
  • Patent number: 5076834
    Abstract: A cyclic amide compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, a haloalkoxy group, a lower alkylthio group or a nitro group; Y is a hydrogen atom, a halogen atom, an alkykl roup, a cycloalkyl group, an alkenyl group, an alkylnyl group, a haloalkyl group, a phenyl group, an alkoxy group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkenyloxy group, an alkynloxy group, a benzyloxy group, a phenoxy group, a haloalkoxy group, a lower alkoxy-lower alkoxy group, a cyanoalkoxy group, an alkylthio group, an alkenylthio group, an alkynylthio group, a benzylthio group, a phenylthio group, ##STR2## (wherein W is an oxygen atom or a sulfuratom, R.sup.3 is a hydrogen atom or an alkyl group and R.sup.4 is an alkyl group), ##STR3## (wherein each of R.sup.5 and R.sup.6 is a hydrogen atom or a lower alkyl group), an alkylsulfonyl group, ##STR4## (wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: October 5, 1990
    Date of Patent: December 31, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Atsuhiko Ikeda, Kenji Matsunari, Yuji Yamada, Michiya Hirata, Yasuo Nakamura, Akira Takeuchi, Hiroyuki Karino
  • Patent number: 5045109
    Abstract: A high concentration herbicide formulation comprising (1) a herbicidally active thiolcarbamate of the following formula I which is liquid at room temperature, (2) at least one nonionic surfactant of the following formula II and (3) an anionic surfactant of the following formula III: ##STR1## wherein R.sup.1 is an alkyl group having from 1 to 3 carbon atoms, a phenyl group or a halogen-substituted phenyl group, R.sup.2 is an alkyl group having from 1 to 5 carbon atoms, and R.sup.3 is an alkyl group having from 1 to 5 carbon atoms, provided that R.sup.2 and R.sup.3 may form a ring; ##STR2## wherein R.sup.4 is ##STR3## wherein R.sup.5 is a hydrogen atom or a methyl group, m is an integer of from 1 to 3, x is an integer of at least 10, y is an integer of from 0 to 10, provided that x+y is within a range of from 10 to 30, A is an oxyethylene group, and B is an oxypropylene group, provided that the addition form of A and B may be a block-form or a random-form; and ##STR4## wherein R.sup.
    Type: Grant
    Filed: February 23, 1990
    Date of Patent: September 3, 1991
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Kanji Nakamura, Susumu Katou
  • Patent number: 5019151
    Abstract: A 2-phenoxypridimine 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 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 ##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.2 is a methoxy group, when R.sup.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: May 28, 1991
    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: 5015283
    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: April 10, 1990
    Date of Patent: May 14, 1991
    Assignee: Kumiai Chemical Industry Co., Ltd.
    Inventors: Takeshige Miyazawa, Kazuhiko Kawano
  • Patent number: 5006157
    Abstract: A cyclic amide compound of the formula: ##STR1## wherein X is a hydrogen atom, a halogen atom, a lower alkyl group, a haloalkyl group, a lower alkoxy group, a haloalkoxy group, a lower alkylthio group or a nitro group; Y is a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a phenyl group, an alkoxy group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkenyloxy group, an alkynyloxy group, a benzyloxy group, a phenoxy group, a haloalkoxy group, a lower alkoxy-lower alkoxy group, a cyanoalkoxy group, an alkylthio group, an alkenylthio group, an alkynylthio group, a benzylthio group, a phenylthio group, ##STR2## (wherein W is an oxygen atom or a sulfur atom, R.sup.3 is a hydrogen atom or an alkyl group and R.sup.4 is an alkyl group), ##STR3## (wherein each of R.sup.5 and R.sup.6 is a hydrogen atom or a lower alkyl group, an alkylsulfonyl group, ##STR4## (wherein R.sup.5 and R.sup.
    Type: Grant
    Filed: November 28, 1989
    Date of Patent: April 9, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Nobuyuki Ohba, Atsuhiko Ikeda, Kenji Matsunari, Yuji Yamada, Michiya Hirata, Yasuo Nakamura, Akira Takeuchi, Hiroyuki Karino
  • Patent number: 4992438
    Abstract: Disclosed are pyrimidine derivatives represented by general formula (I) ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a cyano group; Y.sup.1 represents an alkyl group, a cyanoalkyl group, an alkoxy group, an alkenyl group substituted with a hydroxy group and a halogen atom, an alkynyl group which may be substituted with a hydroxy group, a methylamino group, an alkoxyalkyloxy group, an alkylthioalkyl group or a group of the formula --CH.sub.2 OR.sup.1 where R.sup.1 represents a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl group; Y.sup.2 represents a halogen atom, an alkyl group or a haloalkyl group; R represents a hydrogen atom, an alkyl group, a nitroso group, an alkoxyalkyl group, an alkoxyalkyloxyalkyl group, an alkenyl group, an alkynyl group, a formyl group or an alkylthioalkyl group, with the proviso that (a) when Y.sup.1 represents an alkynyl grop or when Y.sup.1 represents an alkoxy group and Y.sup.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: February 12, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kasano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shinichiro Maeno
  • Patent number: 4988704
    Abstract: Disclosed are pyrimidine derivatives represented by general formula ##STR1## wherein Z.sup.1 represents an alkynyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, or an alkynyloxy group which may be substituted with a halogen atom, and Z.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a group of the formula ##STR2## where Z.sup.3 represents a hydrogen atom or a methyl group; or its salt, and processes for preparing same. Also, agricultural or horticultural compositions containing the pyrimidine derivatives as active ingredient are disclosed, which show high controlling activities for cucumber gray mold (Botrytis cinerea), cucumber downey mildew (Pseudoperonospora cubensis), Alternaria sooty spot of Chinese mustard (Alternaria brassicicola), rice blast (Pyricularia oryzae), etc.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: January 29, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kusano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shin-ichiro Maeno
  • Patent number: 4985066
    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: November 24, 1989
    Date of Patent: January 15, 1991
    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: 4985432
    Abstract: A new class of 5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one derivatives were synthesized. They are useful as agricultural-horticultural fungicides.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: January 15, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Yukio Tokunaga, Koichiro Kaku, Yoshiyuki Kojima, Shinichiro Maeno, Nobumitsu Sawai, Yasuo Saso
  • Patent number: 4971971
    Abstract: A class of novel 5H-1,3,4-thiadiazolo[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: August 28, 1989
    Date of Patent: November 20, 1990
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Yukio Tokunaga, Yoshiyuki Kojima, Shinichiro Maeno, Nobumitsu Sawai, Yasuo Saso
  • Patent number: RE33745
    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, alkylcarbomoyloxy, 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: August 15, 1989
    Date of Patent: November 19, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Mikio Yamaguchi, Yukihiro Watase, Takeshi Kambe, Susumu Katou