WO1998039289A1 - Derives d'uree, agents antibacteriens et antifongiques, algicides et antiperiphytiques, contenant ces derives et destines a un usage industriel - Google Patents

Derives d'uree, agents antibacteriens et antifongiques, algicides et antiperiphytiques, contenant ces derives et destines a un usage industriel Download PDF

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Publication number
WO1998039289A1
WO1998039289A1 PCT/JP1998/000855 JP9800855W WO9839289A1 WO 1998039289 A1 WO1998039289 A1 WO 1998039289A1 JP 9800855 W JP9800855 W JP 9800855W WO 9839289 A1 WO9839289 A1 WO 9839289A1
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Prior art keywords
meo
compound
alkyl group
atom
urea
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PCT/JP1998/000855
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English (en)
Japanese (ja)
Inventor
Shinichi Igarashi
Mitsugu Futagawa
Norio Tanaka
Yasuo Kawamura
Katsushi Morimoto
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Nissan Chemical Industries, Ltd.
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Priority to AU61188/98A priority Critical patent/AU6118898A/en
Publication of WO1998039289A1 publication Critical patent/WO1998039289A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
    • C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
    • C07C317/42—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2

Definitions

  • the present invention relates to antibacterial and antifungal agents and algicides for industrial products, antibacterial agents used in the manufacturing process of industrial products and aquatic organisms for preventing the adhesion of harmful aquatic organisms such as algicides and shellfish. Adhesion prevention. Background art
  • Anti-capi and bulking agents include organic nitrogen compounds, organic nitrogen compounds, and organic halogenated compounds ⁇ ! Nitrogen-containing fat polymers and heavy metal coordination compounds are used.
  • Biofouling prevention ih ⁇ fishing nets, ship bottoms, buoys, and other underwater facilities, thigh structures, thermal or nuclear power cooling water systems, chemical industry heat exchanger cooling water mm, underwater structures Or it is used to prevent harmful aquatic organisms such as heads from attaching to reservoirs.
  • No. 63900 (9 2) discloses diphenyl ether type and diphenyl sulfone type ⁇ rea induction, its ⁇ t method and herbicides.
  • g and German Patent Publication DE 3 2 3 8 0 7 9 ⁇ include benzothiazolyloxyphenyl-rea and benzoxazolyloxyphenyl-rea derivatives and their t methods. And herbicides are disclosed.
  • the above-mentioned organic nitrogen-based compounds, organic nitrogen-based compounds, organic halogen-based compounds, nitrogen-containing fats, polymers, and heavy ⁇ Ji coordination compounds are irritating drugs that pose a problem in the Labor Safety Act, However, there are many drugs that may cause problems from the viewpoint of protection, such as drugs that release formalin or halogen, and that may affect the human body and cause cm staining. Industrial antibacterial and anti-capi and fillers cannot be said to consist entirely of preferred agents.
  • organotin compounds as biofouling inhibitors are effective in preventing the aquatic organisms from fouling, but are highly toxic, and especially remarkably accumulate in fish heads. ing.
  • triptylsuzuoxide was designated as a first-class specified substance by the I ⁇ method (1990), and triphenylsuccinide and triptyltin compounds were designated as a second-class specified chemical. Use is forbidden.
  • the copper compound of ⁇ is widely used for antifouling for roads and ship bottoms, it contains copper which is heavy like ⁇ tin, so there is a concern that ⁇ It can not be said that it is underwater organism adhesion control.
  • composition is effective as a fiber or a biofouling agent. Disclosure of the invention
  • the present inventors have conducted intensive studies in order to solve the above problem, and as a result, it has been found that ⁇ rea induction is high in price, and since it is effective in preventing brown spots, it exhibits a broad spectrum with a low dose and is highly practical.
  • the present invention has been found to be an industrial antibacterial 'anti-kahi ⁇ , ⁇ agent and biofouling prevention II ⁇ , and has made the present invention.
  • the present invention provides-, (1):
  • W represents an oxygen atom or SO 2
  • R 1 represents a C 3 alkyl group
  • R 2 Represents a C w alkyl group or a C 8 alkoxy group
  • R 1 represents a hydrogen atom, a halogen atom, a cyano group or a C 8 alkyl group (the alkyl group may be optionally substituted with a fluorine atom).
  • p is 0, 1, 2 or 3
  • Ar is " ⁇ (2):
  • X 1 and Upsilon 1 are each d-6 alkyl group (the alkyl group may be optionally substituted with fluorine atom), d-6 alkoxy group (the alkoxy group is a fluorine atom Optionally substituted) or a halogen atom, and 1 and m each represent: 0 to 5 and 1 + m always represents 5 or less.
  • X 2 and Y 2 are each a ⁇ ⁇ 8 alkyl group (the alkyl group may be optionally substituted with a fluorine atom), a d-3 alkoxy group (the alkoxy group is a fluorine atom A nitro group or a halogen atom, z represents a ⁇ or ⁇ atom, and n and 0 represent w: 0 to 0 respectively.
  • the present invention relates to industrial antibacterials, anti-capitifiers, Wk agents and anti-biofouling agents which contain ⁇ rare compounds represented by the formula [1].
  • nj is normal
  • ij is iso
  • sj is secondary
  • rtj plays the character
  • r neo j plays the neo.
  • the C physician 8 alkyl group methyl, Echiru, n- propyl, i- flop ⁇ pills, cyclopropyl, and the like.
  • the ds alkyl group includes methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, S-butyl, t-butyl, ⁇ -pentyl, 2-pentyl, 3-pentyl, i -Pentyl, neo-pentyl, t-pentyl, cyclopentyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl and the like.
  • Examples of the alkoxy group include methoxy, ethoxyquin, n-propoxy, i-propoxy, cyclopropoxy and the like.
  • d- 5 alkoxy groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, S-butoxy, t-butoxy, n-pentyloxy, 2-pentyloxy, 3-pentyloxy, i -Pentyloxy, neo-pentyloxy, t-pentyloxy, cyclopropoxy, 1-methylcyclopipropoxy, 2-methylcyclopropoxy, cyclobutoxy, cyclopentyloxy and the like.
  • Halogen atoms include fluorine, chlorine, bromine and iodine.
  • Preferred compounds of the present invention include the following compounds.
  • urea derivative represented by (1) is contained as an active ingredient.
  • the urea of the present invention ⁇ I, jorlock. Patents EP 36390, JP-A-58-216175, and German Patent DE 3238079, etc. are usually used, for example, in the form of ®S (a), (b), (c) and (d). can do.
  • Ar, R 1 , R 2 , R 8 and p in the lower ESJS ⁇ ; are the same as described above, and Ha 1 represents a chlorine atom, a bromine atom or a halogen atom of iodine source ⁇ .
  • the acid acceptor to be used includes, for example, alkali hydroxides, oxides, hydrides, hydrides or hydroxides of alkaline earths, and the like. , Potassium, sodium hydride and the like.
  • the as is preferably dimethylformamide, dimethylsulfoxide, acetate Nitrile, tetrahydrofuran, Jiokisan, acetone, an aprotic polar solvent such as methyl E chill ketone proceeds by ⁇ suitable temperature, for example 2 to 2 4 hours in one 2 0 1 5 0 e C.
  • examples of the acid acceptor used for the condensation with nitrophenols include alkali hydroxides, hydrides, omm, ⁇ hydrides, hydroxides of alkaline earths, and fiberized products.
  • sodium hydroxide, oxidized realm, difficult realm, hydrogenated sodium and the like are used.
  • the book is preferably prepared in an aprotic polar medium such as dimethylformamide, dimethylsulfoxide, sulfolane, acetonitrile, tetrahydrofuran, dioxane, acetone, methylethylketone, or the like, in a suitable medium, for example, in the form of 210 180.
  • the reaction proceeds by stirring for 224 hours.
  • Reduction of the nitro group usually proceeds by hydrogenation (catalytic reduction) in the presence of a fiber such as Pd-C or Raney Ni.
  • This hydrogenation proceeds by using a suitable solvent such as tetrahydrofuran,, ethyl, dioxane or the like, for example, by stirring for 0.5 (TC for 0.524 hours).
  • a suitable solvent such as tetrahydrofuran,, ethyl, dioxane or the like, for example, by stirring for 0.5 (TC for 0.524 hours).
  • Examples of the acid acceptor used for the condensation with sorbamoyl halide include alkali gold Hydroxides, carbonates, carbonates, hydrides or hydroxides of alkaline earth metals, tertiary amines, pyridines, etc., preferably potassium carbonate, nitrogen oxides, etc. Sodium, triethylamine, pyridine and the like.
  • the book is preferably a non-protonic solvent such as dimethylformamide, acetonitrile, tetrahydrofuran, dioxane, acetone, methylethylketone, etc .; halogenated carbon such as chloroform, m-dichlorobenzene, etc .; Using a solvent such as aromatic benzene, toluene, xylene, etc. 7jc element or the like, a suitable solvent, for example, ⁇ 20 to 100. Proceed by stirring with C for 0.5-24 hours.
  • a non-protonic solvent such as dimethylformamide, acetonitrile, tetrahydrofuran, dioxane, acetone, methylethylketone, etc .
  • halogenated carbon such as chloroform, m-dichlorobenzene, etc .
  • a suitable solvent for example, ⁇ 20 to 100. Proceed by stirring with C for 0.5-24 hours.
  • the acid acceptor used for the condensation with thiophenols includes, for example, alkali metal hydroxides, carbonates, carbonized ⁇ ⁇ , hydrides or alkali hydroxides, and fluorides.
  • alkali metal hydroxides carbonates, carbonized ⁇ ⁇ , hydrides or alkali hydroxides, and fluorides.
  • the book is preferably prepared in an aprotic polar medium such as dimethylformamide, dimethylsulfoxide, sulfolane, acetonitrile, tetrahydrofuran, dioxane, acetone, methylethylketone, etc. in a suitable iS, e.g. Proceed by stirring for 2 to 24 hours.
  • an aprotic polar medium such as dimethylformamide, dimethylsulfoxide, sulfolane, acetonitrile, tetrahydrofuran, dioxane, acetone, methylethylketone, etc.
  • a suitable iS e.g. Proceed by stirring for 2 to 24 hours.
  • Oxidation of a thiol group to a sulfone group is usually carried out with m-chloroperbenzoic acid, (Peroxy acid +,), etc. ⁇
  • examples of the acid acceptor used for the condensation with nitrobenzenethiols include, for example, an alkali metal hydroxide, a compound, a mamm, a hydride or an alkaline earth hydroxide, a compound, and the like.
  • Preferable examples include a hydroxide hydroxide, a difficult lithium, and a sodium hydride.
  • the present s is preferably used in an aprotic polar medium such as dimethylformamide, dimethylsulfoxide, acetotrinole, tetrahydrofuran, dioxane, acetone, methylethylketone, etc. in a suitable aprotic medium, for example, Proceed by stirring at 0-150 for 2-24 hours.
  • an aprotic polar medium such as dimethylformamide, dimethylsulfoxide, acetotrinole, tetrahydrofuran, dioxane, acetone, methylethylketone, etc.
  • the target compound obtained in the formulas (a), (b), (c) and (d) can be obtained as a pure product by recrystallization with an appropriate solvent, purification by column chromatography, etc. Monkey
  • the urea derivative used as an active ingredient in the present invention may be used as an active ingredient.
  • the industrial antibacterial agent / anti-capi agent, the agent and the biofouling inhibitor ih ⁇ of the present invention may further contain anti-capi, a ⁇ agent or an anti-biofouling agent, and can be used as a mixture.
  • Image H quaternary ammonium compound, arylisothiocyanate, 2-amino-3,4-chloro-1,4-naphthoquinone, ethylene-bis-thiocyanate, 2-n-octyl-3-isothiazolone, glutaraldehyde, 5-alpha-low 2-n-decyl-3-isothiazolone, 5-chloro-2,4-difluoro-6-methoxyisophthalonitrile, 2-chloro-1-methylamino-6-isopropyl pyramino s-triazine, 5 —Chloro-2-methyl-3-y, thiazolone, 2,3-dichloro-1,4-naphthoquinone, jodomethyl— ⁇ -tolylsulfone, ⁇ , ⁇ —dimethyl-N '—Feneru N'-(fluoro Dichloromethylthio) sulfamide, ⁇
  • the perylene derivative used as an active ingredient in the present invention may be composed of a single compound or a mixture of several kinds of perylene derivatives.
  • urea as an active ingredient in the present invention May be added to the system, or may be formulated as a mixture of a suitable carrier or solvent if the amount is less than 7 minutes, or as a 7j emulsion or dispersion.
  • the formulation of the industrial antibacterial, antifungal, algicidal and biofouling inhibitor of the present invention is outlined in the field of application of industrial antibacterial, antifungal and bulking agents.
  • the urea shoes may be mixed and mixed with suitable carriers and auxiliary agents, such as surfactants, binders, irons, and the like, in a conventional manner; l-emulsions, emulsions, sols (flowables) and other suitable It is used after being formulated into a dosage form.
  • any solid or liquid can be used as long as it is commonly used for industrial antibacterial agents and antifungal agents, and it is not limited to a specific one.
  • solid bodies include mineral powders such as kaolin, bentonite, clay, montmorillonite, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate; K ash, white carbon, slaked lime, ammonium sulfate, urea, etc., or plants Powders, for example, soybean powder, coconut, crystalline cellulose, etc., alumina, silicate, sugar-polymerized highly dispersible, waxes and the like.
  • mineral powders such as kaolin, bentonite, clay, montmorillonite, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate; K ash, white carbon, slaked lime, ammonium sulfate, urea, etc.
  • Powders for example, soybean powder, coconut, crystalline cellulose, etc., alumina, silicate, sugar-polymerized highly dispersible, waxes and the like.
  • liquid carriers examples include water, alcohols such as methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, ethylene glycol, benzyl alcohol, etc., aromatics such as benzene, toluene, xylene, ethylbenzene, Benzene, cumene, methylnaphthalene, etc., or carbon halides 7j, such as chloroform, dichloromethane, ethylene dichloride Mouth lids, ethers, such as ethyl ether, dioxane, tetrahydrofuran, etc., ketones, such as acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, etc., esters, such as ethyl acetate,, butyl, ethyle Glycotriacetate, Okiamyl, etc., nitrinoles, such as
  • surfactants are incorporated for the purpose of emulsification, dispersion, solubilization, wetting, foaming, spreading, and the like.
  • examples of such a surfactant include the following, but are not limited thereto.
  • non-ionic surfactants include polyoxetylene alkyl ether, polyoxetylene alkyl ester, polyoxetylene sorbitan alkyl ester, and sorbitan alkyl ester.
  • anionic surfactants include alkyl benzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate and lauryl sulfate.
  • examples of the cationic surfactant include alkylamines (such as laurylamine, stearyltrimethylammonium chloride and alkyldimethylbenzylammonium chloride).
  • amphoteric surfactant examples include carboxylic acid (betaine type) sulfate, and the like.
  • carboxylic acid betaine type
  • PVA polypinyl alcohol
  • CMC carboxymethyl cellulose
  • gum arabic polyvinyl acetate
  • gelatin casein
  • sodium alginate sodium alginate
  • tragacanth gum guar gum
  • xanthan gum hydroxypropyl
  • a thickener such as cellulose and various auxiliaries can be blended.
  • ⁇ antioxidant according to, 0 qs & [pi e Rukoto monkey in a stabilizer such as an ultraviolet absorption TOJ
  • the industrial antibacterial anti-capillary agent of the present invention containing a rare agent as an active ingredient can be used for the following applications.
  • Anti-biofouling which contains urea as an active ingredient, can be used in the sea, such as fishing nets, ship bottoms, buoys, etc., marine structures, or cooling water systems from nuclear power plants. Cooling water ⁇ 7j roads, underwater structures such as auxiliary equipment for dams, and mussels such as mussels, fujibo, oysters, hydramushi, hydra, selbra, sea squirrels, mosses, and snails, etc. It can be used to prevent harmful underwater organisms such as ⁇ .
  • step S pyridine was distilled off under water, and 50 ml of water was added to the residue, followed by stirring. The obtained crystals were filtered and washed with n-hexane to obtain 2.10 g of Dani ⁇ II o
  • Formulation examples when the urea derivative of the present invention is used as an industrial antibacterial / anti-capi and ⁇ agent are shown using the compound of the present invention, but the compounding ratio of the active ingredient, and the type and amount of the carrier and the auxiliary agent, etc. It is not limited to
  • the formulated industrial antibacterial, anti-capi ⁇ j and bulking agents of the present invention can be used in various industrial raw materials or products by using various preparations as they are or in a suitable organic solvent. Or mixing or spraying on the surface of various industrial raw materials or products, or adding various industrial raw materials or products to the industrial antibacterial, anti-capi and diluent solutions of the present invention. It can be used by various methods in accordance with the industrial antibacterial and antifungal and algicidal methods that have been practiced so far, including the method of immersion, etc. It is not limited.
  • the industrial antibacterial and anti-capillary bulking agent and the preparation for preventing biofouling of the present invention are summarized in the field of application of biofouling prevention li ⁇ lj.
  • the urea derivative used as an active ingredient in the present invention is a solution, It is prepared and used in the form of an emulsion or the like.
  • the underwater biofouling inhibitor of the present invention is used in the form of an antifouling paint, for example, an active ingredient, a urea derivative, is mixed with a ⁇ -shaped idiot to prepare a thigh, and the bottom of a ship, a marine structure, The 7jc pipeline or layer is applied to underwater structures, etc. It is possible to prevent adhesion of things ⁇ !
  • oil varnish As a forming agent, oil varnish, synthetic resin, artificial rubber and the like are used.
  • pigments and the like may be used.
  • the concentration of the active ingredient, urea derivative has no upper limit as long as it can be formed, but i ⁇ 5 om &%, preferably 5 ⁇ 20 with respect to the weight of the antifouling paint. It is blended at a rate of S4%.
  • a formulation example in the case of using the underwater organism adhesion prevention of the present invention as an antifouling is shown by using the present invention, but is not limited thereto.
  • VYHH (vinyl synthetic resin, V C CV) 7
  • the underwater biofouling prevention ih ⁇ of the present invention is used in the form of a solution, for example, a solution prepared by dissolving the active ingredient urea derivative ⁇ : in a solvent together with a ⁇ !
  • a solution prepared by dissolving the active ingredient urea derivative ⁇ : in a solvent together with a ⁇ ! By applying to a net or the like, it is possible to prevent underwater organisms from adhering.
  • synthetic male synthetic male, artificial rubber, natural fineness and the like are used, and as a bandit, xylene, toluene, cumene, methyl ethyl ketone, methyl isobutyl ketone, and acetone are used.
  • an additive such as ⁇ r, etc. may be used according to.
  • concentration of urea derivative, which is an active ingredient there is no upper limit to the concentration of urea derivative, which is an active ingredient, as long as a solution can be formed, but it is mixed at a ratio of 1 to 5, preferably 5 to 30% with respect to the Sfi of the solution. Is done.
  • a surfactant is usually added to a solution of urea as an active ingredient according to a standard method for preparing an emulsion to prepare a desired emulsion. It can be prepared and the type of surfactant used is not particularly limited.
  • the emulsion thus prepared can be kneaded with raw materials such as a net used in the ocean or water, and a fixed net, for example, kneaded with a resin or the like.
  • the concentration of the active ingredient, urea derivative has no upper limit as long as the emulsion can be formed, but it is 1 to 50% by weight, preferably 3 to 30% by weight based on the weight of the emulsion. It is blended in a ratio.
  • the solution or emulsion of the present invention can also be used by adding it to service water, water storage, or the like, in order to prevent adherence of aquatic organisms in a 7j pipeline or a reservoir.
  • the proliferation rate was determined by measuring the number of cells using a hemocytometer.
  • the growth inhibition rate was calculated from the comparison with the untreated group.
  • the growth rate was determined by measuring the amount of chlorophyll from the absorbance using a photometer. The growth inhibition rate was calculated by comparison with the untreated plot.
  • each dissolving amount of a compound of the present invention, to prepare a concentration of the present compound in the medium are each 500 ppb, 5 Opp b
  • the temperature is 20 ⁇ 2 for freshwater silica and the temperature is 23 ⁇ 2 ° C for the other cells, and the culture is shaken at 100 rpm for 24 hours under continuous light.
  • the proliferation rate was determined by measuring the total cell volume using a hemocytometer.
  • the growth inhibition rate was calculated by comparison with the untreated group.
  • a zone to which only acetone was applied was provided as a blank, and a zone to which Omg and 0.5 mg of copper sulfate was applied was provided as a comparative agent.
  • a mussel (Mytilus edulis) having a shell length of about 2 to 2.5 cm was used as a spacer, and four pieces were adhered to the outer periphery of each zone.
  • the prepared was immersed in an aquarium bathing in seawater or ⁇ ⁇ , and ⁇ ⁇ was raised from the 0 aquarium which was allowed to stand at the place for 3 hours, and the adhesion position of the mussel mussels was measured.
  • tests were conducted using Compounds 2 to 5, Compound 8 and Compounds 11 to 15, and the adhesion control effect (adhesion repellent activity) was determined by comparison with copper sulfate used as a comparative drug.
  • the urea derivative represented by (1) has high tt, exhibits a wide spectrum at a low dose, and is useful as an antibacterial agent for industrial use, as an anti-capillary agent, and as a biofouling preventive.

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des dérivés d'urée de la formule générale (1), utiles en tant que principes actifs d'agents antimicrobiens et antifongiques, algicides et antipériphytiques, destinés à un usage industriel. Dans cette formule W représente O ou SO2, R1 représente alkyle C¿1?-C3, R?2¿ représente alkyle C¿1?-C3 ou alcoxy C1-C3, R?3¿ représente hydrogène, halogéno, cyano ou alkyle C¿1?-C3, p vaut 0, 1, 2 ou 3 et Ar représente un groupe correspondant à la formule générale (2) (dans laquelle X et Y représentent chacun indépendamment alkyle C1-C5, alcoxy C1-C5 ou halogéno, et l et m représentent chacun indépendamment un nombre entier de 0 à 5, la somme de l et de m étant égale ou inférieure à 5), ou un groupe correspondant à la formule générale (3) (dans laquelle X?1 et Y1¿ représentent chacun indépendamment alkyle C¿1?-C3, alcoxy C1-C3, nitro ou halogéno, Z représente O ou S, et n et o représentent chacun indépendamment un nombre entier de 0 à 4, la somme de n et de o étant égale ou inférieure à 4).
PCT/JP1998/000855 1997-03-03 1998-03-02 Derives d'uree, agents antibacteriens et antifongiques, algicides et antiperiphytiques, contenant ces derives et destines a un usage industriel WO1998039289A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU61188/98A AU6118898A (en) 1997-03-03 1998-03-02 Urea derivatives, and industrial antibacterial and antifungal agents, algaecidesand antiperiphytic agents containing the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP4783497 1997-03-03
JP9/47834 1997-03-03
JP9/50174 1997-03-05
JP5017497 1997-03-05

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WO1998039289A1 true WO1998039289A1 (fr) 1998-09-11

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PCT/JP1998/000855 WO1998039289A1 (fr) 1997-03-03 1998-03-02 Derives d'uree, agents antibacteriens et antifongiques, algicides et antiperiphytiques, contenant ces derives et destines a un usage industriel

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AU (1) AU6118898A (fr)
WO (1) WO1998039289A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010126456A (ja) * 2008-11-26 2010-06-10 Sumika Enviro-Science Co Ltd 木材保存組成物

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010126456A (ja) * 2008-11-26 2010-06-10 Sumika Enviro-Science Co Ltd 木材保存組成物

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