JP2003252708A - Wood preservative - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a wood preservative capable of preventing wood feeding by wood insect pests and preventing growth and propagation of wood destroying fungi or wood contaminating fungi and safe for humans and animals without adversely affecting the environment. <P>SOLUTION: The wood preservative comprises a compound represented by formula (I) [wherein, R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP>and R<SP>16</SP>are the same or different and each hydrogen atom, hydroxy or a 1-4C alkoxy; R<SP>1</SP>and R<SP>2</SP>may be coupled to form a group represented by -O-(CH<SB>2</SB>)n-O- (wherein, n is an integer of 1-3); R<SP>5</SP>is a 1-4C alkoxy; X is -CH=CH-, -CH<SB>2</SB>-CH<SB>2</SB>- or eopxyethylene; and the linking bond of a dotted line over a solid line denotes a single bond or a double bond] as an active ingredient. <P>COPYRIGHT: (C)2003,JPO

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a wood preservative, and more specifically, wood pests such as termites and flat beetles that erode buildings and furniture in which wood is used, and Pseudomonas edulis, a brown-rot fungus, white Preservation of wood including wood damage, decay, and anti-pollution agents that is effective in preventing wood contamination by wood-rotting fungi such as Kawaratake, which is a decaying fungus, and wood-contaminating bacteria such as Aspergillus niger and Aureobasidium pullulans. Regarding agents.

[0002]

BACKGROUND OF THE INVENTION To control wood pests such as termites and flat beetles, and to prevent decay due to wood-destroying fungi such as Pleurotus ostreatus and Hydrangea and wood-contaminating bacteria such as Aspergillus niger and Aureobasidium pullulans. , Various wood preservatives are known. As the active ingredient, various compounds having an insect repellent action, a wood preservative action, a bactericidal action, a fungicidal action and the like are known. However, these conventionally known wood preservatives have a great influence on safety for humans and livestock and on the environment, and may destroy natural ecosystems.

[0003]

The object of the present invention is to have a high insecticidal effect against harmful insects, a high antiseptic property against wood-destroying fungi, and also a fungus that contaminates the wood when it occurs. It is to provide a wood preservative having antifungal properties. Another object of the present invention is to provide a wood preservative that is highly safe for humans and animals and does not adversely affect the environment. Still another object of the present invention is to provide a wood preservative capable of reliably and efficiently controlling wood pests, wood-destroying fungi and wood-contaminating fungi.

[0004]

Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that
(I)

[Chemical 6] (R in the formula¹, R^Two, R^Three, R^FourAnd R¹⁶Are the same
Or differently, hydrogen atom, hydroxy or C_1-4A
Rukoxy, R¹And R^TwoAre linked to each other by -O-
(CH_Two) Group represented by n-O- (n is an integer of 1 to 3)
May be R ⁵Is C_1-4Alkoxy and X
Is -CH = CH-, -CH_Two-CH_Two− Or epoki
It is a polyethylene and a bond

[Chemical 7] Indicates a single bond or a double bond. It was found that the compound represented by the formula () solves the above-mentioned problems, and further studies were conducted to complete the present invention. That is, the present invention provides the compound of formula (I)

[Chemical 8] (R in the formula¹, R^Two, R^Three, R^FourAnd R¹⁶Are the same
Or differently, hydrogen atom, hydroxy or C_1-4A
Rukoxy, R¹And R^TwoAre linked to each other by -O-
(CH_Two) Group represented by n-O- (n is an integer of 1 to 3)
May be R ⁵Is C_1-4Alkoxy and X
Is -CH = CH-, -CH_Two-CH_Two-Or epoxy
Ethylene, bond

[Chemical 9] Indicates a single bond or a double bond. ) A wood preservative containing a compound represented by the formula (2), (2) a wood preservative as described in (1) which is a wood pest control agent, (3) a wood preservative as described in (1) which is a preservative, (4) The wood preservative according to (1), which is a fungicide, (5) The wood preservative according to (1), which is a termite control agent, (6) Formula (II).

[Chemical 10] (In the formula, R ⁶ is hydroxy or C _1-4 alkoxy, R ⁷ is a hydrogen atom, hydroxy, C _1-4 alkoxy, and R ⁶ and R ⁷ are linked to each other to form —O— (CH ₂ ) n. −
It may be a group represented by O— (where n is 1 or 2), R ⁸ is a hydrogen atom or C _1-4 alkoxy, R ⁹
Is C _1-4 alkoxy, R ¹⁷ is a hydrogen atom, hydroxy or C _1-4 alkoxy, and X is as defined above. ) Or a compound of formula (III)

[Chemical 11] (In the formula, R ¹⁰ is a hydrogen atom, hydroxy C _1-4 alkoxy, R ¹¹ is a hydrogen atom, hydroxy, R
¹⁰ and R ¹¹ are connected to each other to -O- (CH ₂ ) n-O.
(Wherein n is 1 or 2) may be a group represented by R ¹² , R ¹² is a hydrogen atom or hydroxy, and R ¹³ is C.
_1-4 alkoxy, R ¹⁸ is a hydrogen atom, hydroxy or C _1-4 alkoxy, and X is as defined above. )
A wood preservative containing the compound represented by the formula (7) as a active ingredient, (7) the compound represented by the formula (I) is (1) cawaine, or cabaine (2) 7,8-dihydrokawaine, or 7 , 8-dihydrokabine (3) yangonin, (4)
5,6,7,8-Tetrahydroyangonine, (5) Metistisine, (6) 7,8-Dihydromethiscine, (7)
Cis-5-Hydroxy cawaine, or cis-5-hydroxy cabaine (8) 11-methoxy-12-hydroxy-5,6-devidroca wine, or 11-methoxy-1
2-hydroxy-5,6-devidrocaine (9) 7,
8-dihydro yangonin, (10) 5,6-dihydro yangonin, (11) 11-methoxy yangonin, (12) 10-
Methoxy Yangonin, (13) 11-Hydroxy Yangonin or (14) 5,6-Dehydromethistine, the wood preservative according to (1), and (8) Formula (IV)

[Chemical 12] (In the formula, R ¹⁴ and R ¹⁵ are hydrogen atoms or are linked to each other to be methyledidioxy, and X has the same meaning as above.) A wood preservative containing a compound represented by the above as an active ingredient.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention is a wood preservative containing a compound represented by the above formula (I) as an active ingredient, more specifically a wood damage, decay and pollution control agent. Here, wood damage means wood damage caused by wood pests such as termites and flat beetles, wood decay means wood deterioration caused by decay fungi such as Pleurotus ostreatus and Hydrangea, and wood pollution means Aspergillus niger. , Wood contamination by Aureobasidium pullulans. The wood preservative of the present invention is applied to wood, soaked,
By injecting under pressure, safety for humans and animals is high,
It is possible to prevent the above-mentioned wood damage, decay and pollution without destroying the natural ecosystem.

In the present invention, it is represented by the above formula (I).
The compounds are used alone or in combination of two or more. Previous
In the formulas (I) to (III), R¹~ R¹⁸C represented by
_1-4Examples of alkoxy include methoxy and ethoxy.
Ci, n-propoxy, i-propoxy, n-butoxy,
Examples thereof include i-butoxy. R¹And R^Two, R⁶And R
⁷, R¹¹And R¹²Are linked to form -O- (C
H_Two) As a group represented by n-O- (n is an integer of 1 to 3)
Is -O-CH_Two-O- and -O- (CH_Two)_Two−
O- and the like can be mentioned. In formula (I), the group represented by X
The formula for poxyethylene is

[Chemical 13] Is a group represented by. In the formula (III),
R¹⁰, R¹¹，¹²And R¹⁸Are both hydrogen atoms,
X is -CH = CH-, R^ThirteenAre generally metkin compounds
With a compound called the Kawain or Kabane
is there. In formula (II), R⁶Is methoxy, R⁷, R⁸Oh
And R¹⁷Are hydrogen atoms H and R ⁹Is methoxy, X is -CH
The compound of = CH- is called the general name Yangonin.
It is a compound. In formula (III), R¹⁰-R¹¹
Is -O-CH_Two-O-, R¹²And R^{1 8}Is hydrogen
Child, R^ThirteenIs methoxy and X is -CH = CH-
A compound called the generic name Methysticin
is there. The compound represented by the formula (I) is a wood feeding agent for wood pests.
To prevent the generation and reproduction of wood-destroying fungi and wood-contaminating fungi
It has the effect of
Does not have a negative impact on the environment. Compounds included in formula (I)
Among the products, compounds represented by formula (II) and formula (III) are
The compound represented by the formula (IV) is particularly excellent in the effect.
Is excellent.

The compound represented by the formula (I) is a known compound, for example, F. Keller et al., LLOYDIA Vol. 26,
No.1, 1-15 (1963), Georg Boonen et al., Planta Media Vo
L. 64, 504-506 (1998), JP 2001-316260 A.
No. 8-133941 and Torsten Reffstru.
p et al., Acta Chemica Scandinavica B30 613-618 (1976), describes how to obtain the compounds. The compounds represented by the formula (I) include compounds not listed in the literature depending on the combination of the substituents, and these compounds are also commonly used in the compound synthesis according to the synthetic method described in the above literature. It can be synthesized according to the method. Further, the compound used in the present invention may be a glycoside thereof. Examples of sugars that form glycosides include glucose, galactose,
Rhamnose and the like.

The wood preservative of the present invention is not particularly limited in the form of its formulation as long as it contains the above-mentioned raw material of the active ingredient. Further, the wood preservative of the present invention may be formulated. As the formulation form, for example, a solution, a wettable powder,
Suspensions, dispersants, emulsions, oils, liquids such as lotions;
Powder, granule, microcapsule, microsphere,
Examples include solid agents such as flowable agents and foaming agents; semi-solid agent spray agents such as paste agents and creams; aerosol agents; and the like, which can be appropriately selected according to the purpose of use, application site and site. These formulations can be manufactured in conventional manner. The liquid preparation can be produced, for example, by diluting the compound with an appropriate solvent, diluent or carrier. In the case of a wettable powder, a solid diluent or carrier may be used.

Examples of the liquid diluent or carrier include water, methanol, ethanol, n-propanol,
i-propanol, n-butanol, i-butanol,
sec-butanol, t-butanol, n-octanol, 2-butyl-octanol, lauryl alcohol,
Not only monohydric alcohols such as cyclohexanol but also alcohols such as polyhydric alcohols such as ethylene glycol, propylene glycol and glycerin; ethyl ether, propyl ether, isopropyl ether,
Ethers such as dimethoxyethane, cyclic ethers (eg dioxane, terrahydrofuran etc.), mono- or dialkylene glycol monoalkyl ethers (eg ethylene glycol monomethyl ether etc.);
Ketones such as acetone, methyl ethyl ketone, methylisoobutyl ketone, cyclohexanone; ethyl acetate,
Esters such as butyl acetate and n-butyl laurate;
Carbon tetrachloride, chloroform, dichloromethane, 1,2-
Halogenated hydrocarbons such as dichloroethane; hexane,
Aliphatic hydrocarbons such as octane; Alicyclic hydrocarbons such as cyclohexane and cycloheptane; Aromatic hydrocarbons such as benzene, toluene and xylene; Nitriles such as acetonitrile; Carboxylic acids such as formic acid, acetic acid and oleic acid Acetic acid; aprotic polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, pyridine and the like can be mentioned. Plasticizers (for example, ester plasticizers such as di-2-ethylhexyl adipate); petroleum solvents such as kerosene; aromatic hydrocarbons such as ethylnaphthalene and phenylxylylethane; phosphoric acid such as 2-ethylhexylphenyl phosphate Esters and the like can also be used. These liquid diluents and carriers can be used alone or in combination of two or more. Examples of the solid diluent or carrier include diatomaceous earth, mica, clay, kaolin,
Examples thereof include talc, quartz powder, bentonite and the like. These solid diluents or carriers can also be used alone or as a mixture of two or more kinds.

The solid agent can be produced, for example, by diluting or granulating the compound with a suitable solid diluent or carrier. As the solid diluent or carrier, in addition to the solid diluents exemplified above, talc such as talc powder, wax powder, clay such as fine powder clay, mineral powder such as calcium carbonate; wood powder, activated carbon, starch, etc. Vegetable powder of;
Examples include various carriers commonly used in pesticides and horticultural preparations. These solid diluents and carriers are often used as extenders. Solid diluents and carriers may be used alone or in combination of two or more.

The aerosol can be produced, for example, by diluting the above compound with a suitable solvent as needed and filling the container with a propellant. Examples of the solvent include the solvents exemplified above. Examples of the propellant include alcohol (for example, propanol) and liquefied natural gas.

The wood preservative of the present invention may contain various additives depending on the type of formulation, such as antiseptic / antifungal agents; stabilizers such as antioxidants and UV absorbers; binders. A resin capable of forming a film; an emulsifier, a dispersant, a spreading agent, a wetting agent, a penetrant; a thickener; a flow aid; an anticaking agent;
It may contain an aggregating agent; an ultraviolet scattering agent; a moisture removing agent; a coloring agent and the like.

Examples of the antiseptic / antifungal agent include 3
-Iodo-2,3-diiodo-2-propenylethyl carbonate, 3-iodo-2-propynylbutyl carbamate, 2,3,3-triiodoallyl alcohol, parachlorophenyl-3-iodopropargylformal and other organic iodo compounds 2- (4-thiazolyl) benzimidazole, benzimidazole such as 2-thiocyanomethylthiobenzothiazole and benzothiazole compounds; 1- (2 (2 ', 4'-dichlorophenyl) -1,3-dioxolane-2- Ilmethyl) -1H
-1,2,4-triazole, 1- (2 (2 ', 4'-
Dichlorophenyl) -propyl-1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole, α- (2- (4-chlorophenyl) ethyl) -α-
(1,1-Dimethylethyl) -1H-1,2,4-triazole-1-ethanol, α- (4-chlorophenyl) -α- (1-cyclopropylethyl) -1H-1,
Triazole compounds such as 2,4-triazole-1-ethanol; organic zinc such as zinc cobis- (2-pyridine-thiol-1-oxide) phthalate and the like, 4
Examples thereof include isopropyl tropolone (hinokitiol), benzoic acid, sodium benzoate, benzoic acids such as n-butyl paraoxybenzoate, natural compounds such as borax, and didecyldimethylammonium chloride.

The antiseptic / antifungal agent may be (1) the above-mentioned one, (2) a compound represented by the following formula (V), or (3) the above-mentioned one and the following formula (V). The compound represented by may be used at the same time. In the case of (3), the excellent antiseptic / antifungal effect may be exhibited.

As the antiseptic / antifungal agent, a general formula

[Chemical 14] (In the formula, R ₂₁ and R ₂₂ are the same or different,
An alkyl or alkenyl having 2 to 18 carbon atoms having 1 to 18 carbon _{atoms, R 23} and _{R 24} are each independently hydrogen, hydroxy, amino, 1 to 6 carbon atoms alkyl or 1 to 6 carbon atoms an _{alkoxy, R 25} is alkylene of 2 to 18 carbon atoms, shown alkenylene having 3 to 18 carbon atoms, phenylene, or xylylene, which alkyl having 1 to 6 carbon atoms, 1 to 6 carbon atoms alkoxy, the number of carbon atoms It may be substituted with 2 to 6 alkoxycarbonyl or halogen, and Y ₁ is —NHCO—, —CONH.
-, -NHCS-, -COO-, -COS-, -O- or -S-, Y ₂ is -CONH-, -NHCO-,
-CSNH -, - OOC -, - SOC -, - O- or -S- are shown, Z ^- represents an anion. ),
It is preferable because it has excellent antiseptic and antifungal effects.

In the above formula (V), the alkyl having 1 to 18 carbon atoms represented by R ₂₁ and R ₂₂ is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec. -Butyl, pentyl, isopentyl,
sec. -Pentyl, hexyl, heptyl, octyl,
2-ethylhexyl, nonyl, decyl, isodecyl, dodecyl, tetradecyl, hexadecyl, octadecyl and the like can be mentioned. In the above formula, examples of the alkenyl group having 2 to 18 carbon atoms represented by R ₂₁ and R ₂₂ include vinyl, allyl, methallyl, isopropenyl, 1-
Propenyl, 2-propenyl, 2-methyl-1-propenyl, butenyl, pentenyl, hexenyl, heptynyl, octenyl, nonenyl, decenyl, undecenyl,
Dodecenyl, tetradecenyl, hexadecenyl, octadecenyl and the like can be mentioned. In the above formula, R ₂₃ and R
Examples of the alkyl having 1 to 6 carbon atoms represented by ₂₄ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec. -Butyl, pentyl, isopentyl, sec. -Pentyl, hexyl and the like.

In the above formula, the alkoxy having 1 to 6 carbon atoms represented by R ₂₃ and R ₂₄ is, for example, methoxy,
Ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec. -Butoxy, tert. -Butoxy, pentyloxy, isopentyloxy, neopentyloxy, hexyloxy. In the above formula,
As the C2-C18 alkylene represented by R ₂₅ ,
For example, methylene, ethylene, propylene, isopropylene, butylene, isobutylene, sec. -Butylene,
Pentylene, Isopentylene, sec. -Pentylene,
Hexylene, heptylene, octylene, 2-ethylhexylene, nonylene, decylene, isodecylene, dodecylene, tetradecylene, hexadecylene, octadecylene and the like can be mentioned.

In the above formula, R ₂₅ has 3 to 1 carbon atoms.
Examples of the 8 alkenylene include vinylene, propenylene, butenylene, butadienylene, octenylene, decenylene, undecenylene, dodecenylene, tetradecenylene, hexadecenylene, octadecenylene and the like. Examples of the substituent of the group represented by R ₂₅ include alkyl having 1 to 6 carbons, alkoxy having 1 to 6 carbons, alkoxycarbonyl having 2 to 6 carbons, and the like.

Examples of the alkyl having 1 to 6 carbon atoms are the same as those represented by R ₂₃ and R ₂₄ described above. Examples of the alkoxy having 1 to 6 carbon atoms include the same ones as those represented by R ₂₃ and R ₂₄ described above.

Examples of the alkoxycarbonyl having 1 to 6 carbon atoms include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl, s.
ec. -Butoxycarbonyl, tert. -Butoxycarbonyl, pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl and the like. Examples of the halogen include chlorine, fluorine, bromine and iodine. In the formula (I),
Examples of the anion represented by Z, for example, halogen ions (e.g., Cl @ -, Br @ -, I-, etc.), nitrate ion (NO ₃ -) and inorganic anions such as, for example, acetate ion _(CH 3 COO-), Propionate ion (C ₂ H
₅ COO-) and other organic acid anions. Among these, inorganic anions are preferable.

Such a bis-quaternary ammonium salt compound can be produced by a known method in accordance with the specific compounds shown below. Specific examples thereof include, for example,
N, N'-hexamethylenebis (4-carbamoyl-1
-Decylpyridinium bromide) (dimer 38, manufactured by Inui), N, N'-hexamethylenebis (4-carbamoyl-1-decylpyridinium acetate) (dimer 38A, manufactured by Inui), 4,4 '-(tetramethylene) Dicarbonyldiamino) bis (1-decylpyridinium bromide) (Dimer 136, manufactured by Inui), 4,
4 '-(tetramethylenedicarbonyldiamino) bis (1-decylpyridinium acetate) (dimer 1
36A, manufactured by Inui), 1,4-tetramethylenebis (4-carbamoyl-1-hexadecylpyridinium bromide), 1,6-hexamethylenebis (3-carbamoyl-1-dodecylpyridinium bromide), 1,
6-octamethylenebis (3-carbamoyl-1-tetradecylpyridinium bromide), 3,3 '-(1,
3-trimethylenedicarbonyldiamino) bis (1-dodecylpyridinium bromide), 4,4 '(p-xylyldithio) bis (1-octylpyridinium iodide), 3,3'-(m-xylyldithio) bis (1-
Tetradecylpyridinium bromide), N, N'-
(P-Phenylene) bis (4-carbamoyl-1-octylpyridinium bromide), N, N ′-(m-phenylene) bis (3-carbamoyl-1-dodecylpyridinium bromide), 4,4 ′-(p-phthalamide )
Bis (1-octylpyridinium bromide), 3,
3 '-(m-phthalamido) bis (1-octadecylpyridinium dodecylpyridinium bromide), 4,
4 '-(1,8-octamethylenedioxy) bis (1-
Dodecylpyridinium bromide), 3,3 '-(1,
6-hexamethylenedioxy) bis (1-hexadodecylpyridinium bromide), 4,4 '-(1,6-hexamethylenedioxydicarbonyl) bis (1-octylpyridinium bromide), 3,3'-(1 , 6-Tetramethylenedioxydicarbonyl) bis (1-dodecylpyridinium bromide), 4,4 ′-(1,4-tetramethylenedicarbonyldioxy) bis (1-octylpyridinium bromide), 3,3′- (P-phthaloyldioxy) bis (1-decylpyridinium chloride), 4,4 ′-(1,8-octamethylenedicarbonyldithioxy) bis (1-octadecylpyridinium bromide), 3,3 ′-(m- Phthaloyldithioxy)
Examples thereof include bis (1-decylpyridinium iodide). Of these, N, N'-hexamethylenebis (4-carbamoyl-1-decylpyridinium bromide) (Dimer 38, manufactured by Inui), N, N'-hexamethylenebis (4-carbamoyl-1-decylpyridinium acetate) ) (Dimmer 38A, manufactured by Inui),
4,4 '-(tetramethylenedicarbonyldiamino) bis (1-decylpyridinium bromide) (dimer 1
36, manufactured by Inui, and 4,4 ′-(tetramethylenedicarbonyldiamino) bis (1-decylpyridinium acetate) (Dimer 136A, manufactured by Inui) are particularly preferable.

The compound of the above formula (V) is disclosed in JP-A-9-11.
0692, JP10-95773A, JP10-287566, JP2000-1361.
It can be produced by the method described in Japanese Patent Publication No. 85 or a method analogous thereto. These bis-quaternary ammonium salt compounds may be used alone or in combination of two or more.

Examples of the antioxidant include 4,4'-
Thiobis-6-t-butyl-3-methylphenol, butylated hydroxyanisole (mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol), P-octylphenol, mono (or Di or tri)-(α-methylbenzyl) phenol, 2,6-di-t-butyl-p-cresol (BH
T), pentaerythrityl tetrakis [3- (3,5-
Di-t-butyl-4-hydroxyphenyl)] propionate and other phenolic antioxidants; N, N'-di-
Amine-based antioxidants such as 2-naphthyl-p-phenylenediamine; Hydroquinoline-based antioxidants such as 2,5-di (t-amyl) hydroquinoline; Sulfur-based antioxidants such as dilaurylthiodiuropionate Examples of the agent include phosphoric acid type antioxidants such as triphenyl phosphite.

Examples of the ultraviolet absorber include 2-
Benzotriazole compounds such as (2′-hydroxy-5′methylphenyl) benzotriazole and 2- (2′-hydroxy-4′-n-octoxyphenyl) benzotriazole; 2-hydroxy-4-methoxybenzophenone, 2 Benzophenone-based compounds such as hydroxy-4-n-octoxybenzophenone; Salicylic acid-based compounds such as phenyl salicylate and p-t-butylphenyl salicylate; 2-Ethylhexyl-2-cyano-
3,3-diphenyl acrylate, 2-ethoxy-2 '
-Ethyloxalic acid bisanilide, dimethyl succinate-1
-(2-hydroxyethyl) -4-hydroxy-2,
2,6,6-tetramethylpiperidine polycondensation product and the like can be mentioned.

Examples of the resin capable of forming a film include polyolefins such as polyethylene and polypropylene, polyvinyl acetate, polyvinyl alcohol, acrylic resins, polyvinyl chloride, styrene resins, fluororesins,
Chlorinated polyolefin, alkyd resin, polyamide,
Thermoplastic resins such as polyester; thermosetting resins such as phenol resin, urea resin, melamine resin, furan resin, unsaturated polyester resin, and epoxy resin can be exemplified.

As the emulsifier, the dispersant, the spreading agent, the wetting agent and the penetrating agent, a conventional surface active agent such as an anionic surface active agent and a nonionic surface active agent can be used. Examples of the anionic surfactant include metal soaps, sulfate ester salts such as sodium alkylsulfate, alkylbenzene sulfonates such as sodium alkylbenzenesulfonate, [for example, Takemoto Yushi Co., Ltd., trade name Newcalgen BX- C] such as alkylnaphthalenesulfonic acid, 2
Dialkyl sodium sulfosuccinate [for example, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., trade name Neocor SW-C] and the like, dialkyl salts of 2-sulfosuccinic acid, polycarboxylic acid type surfactants [for example, manufactured by Sanyo Kasei Co., Ltd., Trade name Toxanone GR-30], α-olefin sulfonate, polyoxyethylene distyrenated phenyl ether sulfate ammonium salt [eg, Dai-ichi Kogyo Seiyaku Co., Ltd., trade name Dixsol 60A], sodium lignin sulfonate, Examples thereof include potassium lignin sulfonate. Examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether [for example, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., trade name Inogen EIA-142 (EA-142)] polyoxyethylene. Aryl ether, resin acid polyhydric alcohol ester, fatty acid polyhydric alcohol ester, fatty acid polyhydric alcohol polyoxyethylene, sucrose fatty acid ester, block copolymer of ethylene oxide and propylene oxide [eg, Sanyo Kasei Co., Ltd., Product name New Pole P
E-64] and the like.

Examples of the thickener include polyvinyl alcohol, xanthan gum, duran gum, polyacrylic acid and its salts, and the like, and as a flow aid, a PAP aid (eg, isopropyl phosphate), wax, polyethylene, fatty acid. Examples include metal lubricants, organic lubricants such as paraffin and silicone oil, and inorganic lubricants such as talc. As anticaking agents, for example, white carbon, diatomaceous earth,
Examples include magnesium stearate, aluminum oxide, titanium dioxide and the like. Examples of the aggregating agent include liquid paraffin ethylene glycol, diethylene glycol, triethylene glycol, and isobutylene polymer [eg, Idemitsu Petrochemical Co., Ltd., trade name IP Solvent-
2835] and the like. As an ultraviolet scattering agent,
Titanium dioxide etc. can be illustrated. As a moisture remover,
Drying agents such as anhydrous gypsum and silica gel powder may be mentioned.
Colorants include, for example, organic or inorganic pigments and dyes.

The wood preservative of the present invention may contain other insect repellents, pest repellents and efficacy enhancers. Examples of the other insect repellents include, for example, organophosphorus compounds such as phoxime, chlorpyrifos, fenitrothion, pyridafenthion, and isofenphos; carbamate compounds such as bassa and propoxer; cyfluthrin, permethrin, tralomethrin, fenvalerate, etofenprox, silafluofen, Pyrethroid compounds such as bifenthrin, imidacloprid, nitenpyram, acetamiprid, clothianidin, neonicotinoid compounds such as dinotefuran, phenylpyrazole compounds such as fipronil, nereistoxin compounds such as bensultap, chlorophenapir, hiba oil, in Hiba Fatty acids such as natural oil, decanoic acid, octanoic acid (Japanese Patent No. 29
25081), octanol, lauryl alcohol,
In addition to decanol, isodecanol, methyl caprate, methyl caprate (Japanese Patent No. 2919280), boric acid, etc., plants including Neem (Japanese Patent Laid-Open No. 3-41011), Moringa genus, and Malarium -3
No. 29514). Further, chitin synthesis inhibitors such as lufenurone, hexaflumuron, diflubenzuron, and flufenoxuron known as insect growth regulators (IGRs) and juvenile hormone-like compounds such as methoprene and hydroprene may be contained. In addition, synergists such as MGK264, isobornyl thiocyanoethyl ether and the like may be included.

The content of the above-mentioned active ingredient can be appropriately selected depending on the dosage form of the wood preservative and the application method. In the case of a liquid agent, a semi-solid agent or a solid agent, the concentration of the above components is, for example, 0.01 to 8 as the compound in the wood preservative.
It is 0% by weight, preferably about 0.1 to 30% by weight. When the wood preservative is an aerosol agent, the concentration of the component in the filling material filled in the container is, for example, 0.01 to 20% by weight, preferably 0.05 to 1% as a compound.
It is about 0%.

The wood preservative of the present invention can be applied to wood pests, wood-destroying fungi and wood-contaminating fungi, especially termites that are wood pests. Examples of wood pests to which the wood preservative according to the present invention is applied include insects belonging to the orders Termite, Coleoptera, and Hymenoptera. Specific examples of the insects belonging to the above-mentioned termites include those belonging to the family Termites, such as Yamato termites and J. termites, and those belonging to the family of Rubitermites, such as Daikoku termites and American termites. Specific examples of insects belonging to the order Coleoptera, flatworm, beetle bark beetle, zelkova beetle bark beetle, those belonging to the flatworm beetle family such as algal flounder beetle,
Beetle beetle, pine beetle, beetle beetle, black beetle beetle, black beetle beetle, etc. Examples thereof include those belonging to the family Cerambycidae such as scuttle beetle, those belonging to the family Weevil beetle such as boll weevils, and those belonging to the family Beetle beetle such as Saxskiki beetle, and those belonging to the family Buprestidae and Curculionidae. Specific examples of the insects belonging to the order Hymenoptera include, for example, those belonging to the family Bee, such as bear bee, and those belonging to the family ant, such as Muneakao ant. Examples of the wood-destroying fungus which is a target of the wood preservative according to the present invention include various fungi, for example, brown-corroding fungi (for example, Pleurotus ostreatus, Itotake, Pleurotus ostreatus, Physcomitrella patens, Namitake mushroom) and white-rot fungi (for example Kawaratake). . Examples of the wood-contaminating bacteria to which the wood preservative of the present invention is applied include Aspergillus niger and Aureobadium pullulans. When the wood preservative of the present invention is used for controlling pests, particularly house pests such as termites, and wood-destroying fungi and wood-contaminating fungi, it can be controlled with high efficiency even in a small amount.

Examples of the preservation method using the wood preservative of the present invention include invasion sources and generation sources of harmful insects and wood-destroying fungi, such as kitchen, bathroom, living room, corner of floor, underfloor, ceiling, base,
The wood preservative may be applied to pillars, walls, wooden products such as furniture, soil and the like. Wood preservative application methods include wood feeding pests, wood-destroying fungi, various modes depending on the invasion source or source of wood-contaminating bacteria, for example, application, spraying, dipping, injection,
Methods such as blending, spraying, etc. are included. The treatment method of these is not particularly limited as long as the wood can be protected. For example, other than directly treating the wood, a method such as a basic heat insulating agent treatment or embedding in the soil may be performed. It may also be applied to plywood, laminated wood, wood board, etc. by mixing with an adhesive. When applied to the soil, the preservative can be applied by spraying on the soil surface, spraying on grooves formed in the soil, mixing with the soil, or the like. In addition, the wood preservative is a synthetic resin sheet, paper, or a sheet-like base material such as cloth, which is held by coating, impregnation, kneading or the like to prepare a sheet material, which is used as a place where the pests invade or occur. It can also be made to work effectively by placing or sticking it.

[0032]

EXAMPLES The present invention will be described in more detail based on test examples and examples, but the present invention is not limited to these examples. Incidentally,% is based on weight.

Example 1 (Soil treatment agent) A preparation was prepared according to the following formulation. Hinoki wood flour (2 mm) 50% 7,8-Dihydrokawine 30% Dispersant (Emulgen 2025G Kao) 10% Carnauba wax 10% 100%

Example 2 (Soil treatment agent) Hinoki wood flour (2 mm) 40% 7,8-Dihydrokawine 10% Capric acid 40% Dispersant (Emulgen 2025G Kao) 10% 100%

Example 3 (Soil treatment agent) Hinoki wood flour (2 mm) 10% Hiba wood flour (2 mm) 10% 7,8-Dihydrokawaine 10% Turmeric (80 mesh) 10% Sandscon (40 mesh) 10% Sojutsu (40 mesh) 10% Kawa (40 mesh) 30% Dispersant (Emulgen 2025G manufactured by Kao) 10% 100% The above 7,8-dihydrokawaine in Examples 1 to 3 was prepared as an acetone solution to a predetermined concentration. Until cypress wood flour was mixed and air-dried repeatedly to adjust. Also,
The formulation examples of Examples 1 to 3 can be sprayed as a wettable powder by diluting with water 5 to 10 times, or can be directly used as a powder or diluted with water to fill the damaged part of the wood.

Example 4 (Oil agent for xylem treatment) 7,8-Dihydrokawine 1% Propylene glycol 70% Solvent ( Isophor 14T manufactured by Condea ) 29% 100%

Example 5 (oil treatment oil for xylem) Kawine 0.5% 7,8-dihydrokawine 1.0% Metistisine 0.5% Propylene glycol 80.0% Solvent ( Isophor 14T Condea ) 18.0 % 100.0%

Example 6 (oil treatment oil for wood) Kawaine 0.5% 7,8-dihydrokawaine 1.0% Metistisine 0.5% Propylene glycol 80.0% Solvent (Isophor 14T Condea) 17.0 % IPBC 1.0% 100.0%

Example 7 (wood treatment oil agent) 7,8-dihydrokawaine 1.5% Propylene glycol solution containing 10% of dimer 38A 10% Propylene glycol 88.5% 100.0%

Example 8 (Wood Part Treatment Oil Agent) 7,8-Dihydrokawine 1.0% Kawine 0.5% Metistisine 0.5% Dimer 38 1.0% Propylene Glycol 97.0% 100.0% Example All of the 4 to 8 xylem-treating oils have good xylem permeability and exhibit excellent wood antiseptic and antifungal effects.

Example 9 (Wood part emulsion) 7,8-Dihydrokawine 1.0% Propylene glycol 30.0% Solvent (Isophor 12T (manufactured by Condea) 10.0% Dispersant (Emulgen 2025G manufactured by Kao) 7.0% Water 52.0% 100.0%

Example 10 (Paint Composition) Kawine 0.500% 7,8-Dihydrokawine 1.000% Ethanol 64.195% Flaxseed oil 30.000% Iron oxide 3.000% Lecithin 0.300% Talc 1 000% Cobalt octoate 0.005% 100.000%

Test Example 1 (1) Feeding Inhibition Test A 1 w / w% acetone solution of each compound shown in Table 1 (however, in the case of hispidin, a 1 w / w% methanol solution) was prepared. A 1 × 1 cm No. 2 filter paper was dipped in this solution, pulled up and air dried. This was put into an 11K bottle in which 100 termite termite workers were previously bred, and the state of feeding was observed. A reagent manufactured by Calbiochem was used as hispidin. The results are shown in Table 1.

[0044]

[Table 1]

Test Example 2 (1) Wood decay prevention test A 5 w / w% acetone solution of the compounds shown in Table 2 was prepared.
A 1 × 1 cm No. 2 filter paper was dipped in this solution, pulled up and air dried. This test piece was cultured on a medium in which a PDA medium was spread on a petri dish in advance.
is palustris) and an antibacterial test was performed. The condition after 8 weeks is summarized in Table 2.

[0046]

[Table 2]

Test Example 3 (1) Growth inhibition test for wood-contaminating bacteria A 5 w / w% acetone solution of the compound shown in Table 3 was prepared.
A 1 × 1 cm No. 2 filter paper was dipped in this solution, pulled up and air dried. About 2 ml of a suspension obtained by mixing spores of four kinds of wood-contaminating bacteria was sprayed on the obtained filter paper, and the growth of the bacteria was observed for 3 days on a petri dish covered with a 2% agar medium. The results are shown in Table 3. Contaminated bacteria Alpergis niger Penicillium funiculosum Aureobasidium pullulans Gliocladium virens

[0048]

[Table 3]

[0049]

Industrial Applicability The wood preservative of the present invention prevents wood feeding by wood pests, has an action of preventing the generation of wood-destroying fungi and wood-contaminating fungi, and has high safety against humans and livestock. It is an excellent wood preservative with no adverse effects on the natural environment.

   ─────────────────────────────────────────────────── ─── Continued front page    F term (reference) 2B230 AA01 AA04 AA05 BA01 CB02                       CB06                 4H011 AA01 AC03 BA01 BB08 BC03                       BC06 BC18 BC19 BC20 BC22                       DA02 DA13 DA16 DD05 DH13

Claims (8)

[Claims] 1. An active ingredient of formula (I) [Chemical 1] (R in the formula¹, R^Two, R^Three, R^FourAnd R¹⁶Are the same
Or differently, hydrogen atom, hydroxy or C_1-4A
Rukoxy, R¹And R^TwoAre linked to each other by -O-
(CH_Two) Group represented by n-O- (n is an integer of 1 to 3)
May be R ⁵Is C_1-4Alkoxy and X
Is -CH = CH-, -CH_Two-CH_Two-Or epoxy
Ethylene, bond [Chemical 2] Indicates a single bond or a double bond. )
A wood preservative containing a compound. 2. The wood preservative according to claim 1, which is a pest control agent for wood. 3. The wood preservative according to claim 1, which is a preservative. 4. The wood preservative according to claim 1, which is a fungicide. 5. The wood preservative according to claim 1, which is a termite control agent. 6. Formula (II): (In the formula, R ⁶ is hydroxy or C _1-4 alkoxy, R ⁷ is a hydrogen atom, hydroxy or C _1-4 alkoxy, and R ⁶ and R ⁷ are linked to each other to —O— (C
H ₂ ) n-O- (where n is 1 or 2) may be a group represented by R ⁸ is a hydrogen atom or C _1-4 alkoxy, R ⁹ is C _1-4 alkoxy, and R ¹⁷ is Hydrogen atom,
Hydroxy or C _1-4 alkoxy, X has the same meaning as above. ), Or a compound represented by the formula (III): (In the formula, R ¹⁰ is a hydrogen atom, hydroxy or C _1-4 alkoxy, R ¹¹ is a hydrogen atom or hydroxy, and R ¹⁰ and R ¹¹ are linked to each other to —O— (CH ₂ ) n—.
It may be a group represented by O— (where n is 1 or 2), R ¹² is a hydrogen atom or hydroxy, and R ¹³ is C.
_1-4 alkoxy, R ¹⁸ is a hydrogen atom, hydroxy or C _1-4 alkoxy, and X has the same meaning as above. ) A wood preservative containing the compound represented by the formula (1) as an active ingredient. 7. A compound represented by the formula (I) is (1) cawaine, or cavaine (2) 7,8-dihydrokawaine, or 7,8-dihydrocabaine (3) yangonin, (4) 5, 6,7,8-Tetrahydroyangonine, (5) Metistisine, (6) 7,8-Dihydromethiscine, (7) Cis-5-hydroxykawaine, or Cis-5.
Hydroxykabaine (8) 11-methoxy-12-hydroxy-5,6-dehydrokawaine, or 11-methoxy-12-hydroxy-5,6-dehydrokabaine (9) 7,8-dihydroyangonine, (10) 5. , 6-dihydro yangonin, (11) 11-methoxy yangonin, (12) 10-methoxy yangonin, (13) 11-hydroxy yangonin or (14) 5,6-dehydromethystisine. Item 10. The wood preservative according to Item 1. 8. A compound of formula (IV): (In the formula, R ¹⁴ and R ¹⁵ are hydrogen atoms or are linked to each other to be methyledidioxy, and X is as defined above.) A wood preservative containing a compound represented by the above as an active ingredient.