Abstract: 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:
Grant
Filed:
October 14, 1992
Date of Patent:
February 21, 1995
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: 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:
Grant
Filed:
September 17, 1992
Date of Patent:
January 31, 1995
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: 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:
Grant
Filed:
December 23, 1992
Date of Patent:
January 10, 1995
Assignees:
Kumiai Chemical Industries Co., Ltd., Ihara Chemical Industries Co., Ltd.
Abstract: 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:
Grant
Filed:
October 27, 1993
Date of Patent:
January 10, 1995
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: A method for producing an asymmetric biaryl derivative which comprises dehalogenocoupling halogenated benzene derivatives, wherein a bromobenzene derivative of the formula: ##STR1## wherein R is a lower alkyl group or a lower alkoxy group, which is attached at the 3- or 4-position, and a 2-chlorobenzene derivative of the formula: ##STR2## wherein R' is a cyano group or an alkoxycarbonyl group, are reacted in pyridine in the presence of triphenylphosphine, an anhydrous nickel compound and a reducing metal to obtain an asymmetric biaryl derivative of the formula: ##STR3## wherein R and R' are as defined above, and R is attached at the 3- or 4-position.
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 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:
Grant
Filed:
July 28, 1992
Date of Patent:
November 22, 1994
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: A process for the production of a black coloring material characterised by treating a compound selected from finely powdered sugar, protein and a polyamide polymer, having amino groups with a naphthoquinone derivative represented by the general formula (1): ##STR1## wherein R.sub.1 represents a hydrogen atom, a hydroxyl group, a halogen atom, or a group represented by the following formula: ##STR2## wherein R.sub.2 represents a hydrogen atom or a hydroxyl group, R.sub.3 represents an alkyl group, an alkenyl group or a hydroxylalkyl group, and n represents 1 or 2; cosmetics comprising a black coloring material produced by the above process; and a process for staining a substrate using the obtained black coloring material.
Abstract: The present invention provides a condensed heterocyclic derivative represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, an alkenyl group, or the like, R.sup.2, R.sup.3, R.sup.4, R.sup.5, and R.sup.6 independently represent a hydrogen atom, a lower alkyl, or the like, W is represented by --OC(O)--, --SC(O)--, or the like, and Z represents a 2-indolyl group or the like. The present invention also provides an agricultural or horticultural fungicide which comprises an amount of the condensed derivative known to be effective as a fungicide. The agricultural or horticultural fungicide according to the present invention exhibits a superior control effect for downy mildew and late blight, without harm to nonfungal, photosynthesizing plants.
Type:
Grant
Filed:
September 7, 1993
Date of Patent:
September 20, 1994
Assignees:
Kumai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: A polyurea resin having excellent mechanical properties along with high heat resistance can be prepared by the reaction of an aromatic polyamine component and an aliphatic polyisocyanate component, in which the aromatic polyamine component is a combination of a first aromatic polyamine compound which is typically a polyoxyalkylene bis(aminobenzoate) compound and a second aromatic polyamine compound selected from various classes of aromatic polyamine compounds different from the first aromatic polyamine compound in a specified weight proportion. The polyurea resin can be imparted with further improved heat resistance when the aliphatic polyisocyanate component is a combination of an aliphatic diisocyanate compound and a cyclic trimer of an aliphatic polyisocyanate compound in a specified weight proportion.
Type:
Grant
Filed:
October 20, 1992
Date of Patent:
June 7, 1994
Assignee:
Ihara Chemical Industry Co., Ltd.
Inventors:
Masaaki Hattori, Chikara Hijikata, Yuichiro Sato
Abstract: The present invention provides a process for producing a halomethyl ester of an aliphatic carboxylic acid in which a metal salt of an aliphatic carboxylic acid is reacted with a dihalomethane in the presence of a phase transfer catalyst, whereby the efficient production of a halomethyl ester of an aliphatic carboxylic acid has been made possible without the formation of a halomethyl ether as a by-product. The bis compound bis[aliphatic carbonyloxy)methane], which is obtained as a by-product, is hydrolyzed to enable the quantitative recovery of an aliphatic carboxylic acid and its reuse. Thus, the present process is preferable as a process for industrial production of a halomethyl ester of an aliphatic carboxylic acid.
Abstract: 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:
Grant
Filed:
October 6, 1992
Date of Patent:
June 7, 1994
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: 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:
Grant
Filed:
December 23, 1992
Date of Patent:
May 17, 1994
Assignees:
Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: An industrial process which is a process for producing a hexahydropyridazine-1,2-dicarboxy derivative in good yield, is provided. By reacting a hydrazine dicarboxy derivative of the general formula (1):ROC--NH--HN--COR (1)(wherein R is an alkoxy group or an aryl group) with a dihalogenobutane of the general formula (2):X--CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --X (2)(wherein X is a chlorine or bromine atom) in the presence of a base selected from an alkali metal carbonate or hydroxide, a hexahydropyridazine-1,2-dicarboxy derivative represented by the general formula: ##STR1## (wherein R has the same meaning as R in the above general formula (1)) is obtained efficiently.
Abstract: 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:
Grant
Filed:
October 6, 1992
Date of Patent:
February 8, 1994
Assignees:
Kumiai Chemical Industry Co. Ltd., Ihara Chemical Industry Co., Ltd.
Abstract: The present invention provides a dithiocarbamic acid salt which can be converted, at a very high yield, to an isothiocyanate suitable for use as an intermediate for production of thiazabicyclononane derivative or monothiourazole derivative; a process for producing said dithiocarbamic acid salt at a high yield without using thiophosgene having a toxicity problem; and a process for producing an isothiocyanate using said dithiocarbamic acid salt.The dithiocarbamic acid salt of the present invention is represented by general formula (2), and the process for producing said dithiocarbamic acid salt (2) comprises reacting an aniline represented by general formula (5) with carbon disulfide in the presence of 1,4-diazabicyclo[2.2.2]octane (3) or 4-pyrrolidinopyridine (4).The process for producing an isothiocyanate (1) according to the present invention comprises reacting the above dithiocarbamic acid salt (2) with a halogen compound.
Abstract: A process for production of 2-acetylbenzo[b]thiophene represented by the formula (I): ##STR1## comprising the steps of: (1) reacting 2-halogenobenzaldehyde represented by the formula (II): ##STR2## wherein X represents a halogen atom, with a compound represented by the formula (III):H.sub.i S.sub.j M.sub.kwherein M represents an alkali metal, i represents zero or 1, j represents an integer of at least 1, and k represents an integer of 1 or 2, and preferably also with sulfur; and(2) reacting the reaction product with a monohalogenoacetone represented by the formula (IV) ##STR3## wherein X.sup.1 represents a halogen atom.
Abstract: A novel black coloring material is obtained by treating a chitosan with a dyestuff of the lithospermum root. If a water-insoluble chitosan is used as the chitosan, a finely divided black coloring material is obtained, and if a gelatinous chitosan salt is used as the chitosan, a gelatinous black coloring material is obtained. If a water-soluble chitosan, chitosan oligosaccharide or D-glucosamine, or a salt thereof is used as the chitosan, a liquid black coloring material is obtained. If a powdery polymeric substance is treated with such a black coloring material, a polymer-based black coloring material is obtained, and if a fiber is dyed with such a black coloring material, the fiber is dyed to a black color having a low lightness.
Abstract: A pyrimidine or triazine derivative and its salt, said pyrimidine or triazine derivative having the formula: ##STR1## wherein R represents a group of the formula OR.sup.3 {wherein R.sup.3 represents a hydrogen atom, an alkyl group, etc.}, a group of the formula SR.sup.6 {wherein R.sup.6 represents a hydrogen atom, an alkyl group, etc.}, a group of the formula ##STR2## {wherein R.sup.7 and R.sup.8 represent a hydrogen atom, an alkyl group, etc.}, or an imidazolyl group:R.sup.1 represents a hydrogen atom, an alkyl group, etc.;R.sup.2 represents a hydroxyl group, an alkyl group, etc.;A and B represent an alkyl group, etc.;Y represents an oxygen atom, etc.; andZ represents a methine group or a nitrogen atom.
Type:
Grant
Filed:
March 4, 1992
Date of Patent:
September 7, 1993
Assignees:
Kumiai Chemical Co., Ihara Chemical Industry Co., Ltd.