JP2017043612A - Industrial pest control agent containing plant extract as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an industrial pest control agent in which the active ingredient is derived from natural plants, that is usable in a wide range of industrial applications, and has excellent antibacterial, antifungal, antiseptic, algicidal activity and/or excellent wood pest control activity in each of these applications.SOLUTION: Provided is an industrial pest control agent containing plant extract as an active ingredient.SELECTED DRAWING: None

Description

  The present invention relates to an industrial pest control agent comprising a plant extract as an active ingredient.

Conventionally, for example, various industrial waters in papermaking processes of paper pulp mills, cooling water circulation processes of various factories, metal processing oils (cutting oils, etc.), casein, starch paste, glue, coated paper, paper coating liquid For various industrial products such as surface sizing agent, paint, adhesive, wood, fiber, wood powder, synthetic rubber latex, ink, polyvinyl alcohol film, vinyl chloride film, resin product, cement admixture, sealing agent, joint material Is prone to the growth of harmful microorganisms such as bacteria, molds, yeasts, and algae, which causes a decline in productivity and quality, and the generation of malodors. In addition, industrial products such as wood and wood-containing building materials are known to decay due to the action of microorganisms such as basidiomycetes, and to deteriorate in quality and strength due to the feeding damage of wood pests such as termites. .
Therefore, in order to control the growth of such harmful microorganisms, various industrial disinfectants that exhibit antibacterial, antifungal, antiseptic and antialgal effects on industrial water and industrial products such as 2- (methoxy Add carbonylamino) -1H-benzimidazole (carbendazim), 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT), 2,2-dibromo-3-nitropropionamide (DBNPA), etc. In addition, in order to control wood pests, various insecticides that exhibit termite killing effects and termite repellent effects on industrial products made of wood, such as E-1- (2-chloro-1,3-thiazole- 5-ylmethyl) -3-methyl-2-nitroguanidine (clothianidin), 2-methylbiphenyl-3-ylmethyl (Z)-(1RS, 3RS) -3- ( - adding and chloro-3,3,3-trifluoro-prop-1-enyl) -2,2-dimethylcyclopropanecarboxylate (bifenthrin) is widely implemented.
On the other hand, termite control agents derived from natural products (for example, Patent Documents 1 to 3) are known, but the effect is not sufficient. In addition, Non-Patent Document 1 reports that “plumbagin” obtained from Kodachilmatsuri (Isoaceae) has antibacterial activity against rice sesame leaf blight fungi, but as an industrial fungicide It has not been reported that it can be used.
Furthermore, it is not yet known about a drug that can simultaneously obtain two different effects of treating a single drug, such as an antibacterial, fungicidal, antiseptic, and algal control effect, and a wood pest control effect.

Japanese Patent Laying-Open No. 2005-074776 JP 2008-195620 A JP 2008-195621 A

Michio Masuko and five others "Plumbagin, an Antifungal Factor in Ceratostigma willmottianum (Plumbaginaceae Plant)" Journal of the Japanese Society for Plant Pathology, Japanese Society for Plant Pathology, 1970, Vol. 36, P.I. 286-288.

  The active ingredient is derived from natural plants and can be used in a wide range of industrial applications, and in each of these applications, it has excellent antibacterial, antifungal, antiseptic, algal control and / or industrial pest control activities Development of biocontrol agents is an issue.

As a result of intensive studies to solve the above problems, the present inventor applied a plant extract as an industrial pest control agent. As a result, the present inventors have excellent antibacterial activity against bacteria, molds, yeasts, and algae and / or wood pests. It has been found that it has a controlling activity against this, and has completed the present invention.
Furthermore, the plant extract which has two different control activity of antibacterial activity and wood pest control activity was discovered. In the conventional industrial disinfectant, there has been no report on a medicine having a wood pest control activity without mixing a plurality of active ingredients, and the present invention is the first two different antibacterial activity and wood pest control activity. The present inventors have found a drug having a control activity and have solved the above problems.

The gist of the present invention is specifically as follows.
1. An industrial pest control agent having at least one of antibacterial activity and wood pest control activity, comprising a plant extract as an active ingredient.
2. 1. The plant extract is an extract obtained from at least one plant selected from the group consisting of the following (1) to (10): Industrial pest control agent as described in 1.
(1) The genus Pongamia (2) The genus Carotropis (3) The genus Plumbago (4) The genus Maytenus (5) The genus Baccharis (6) The genus Rubia (7 ) Genus Calophyllum (8) genus Artica (9) genus Kobresia (10) genus Caesalpinia Both industrial antibacterial activity and wood pest control activity, characterized by containing as an active ingredient one or more plant extracts of the genus Pongamia, Calotropis, and Plumbago 1. having activity Or 2. Industrial pest control agent as described in 1.
4). 1. Having both industrial antibacterial activity and wood pest control activity, characterized by containing plumbagin, a plant extract extract component of the genus Pongamia. ~ 3. The industrial pest control agent according to any one of the above.
5). 1. It has wood pest control activity, characterized by comprising a plant extract of the genus Maytenus as an active ingredient. Or 2. Industrial pest control agent as described in 1.
6.1. ~ 5. A method for protecting industrial materials or industrial products, wherein the industrial pesticide according to any one of the above items is applied to industrial materials or industrial products.
7). A compound represented by the following structural formula or an optically active isomer thereof.

The industrial pest control agent comprising the plant extract of the present invention as an active ingredient expresses excellent antibacterial, antifungal, antiseptic, and algal control activities, and has performance as a control agent for bacteria, fungi, yeasts, and algae. Any one or more of the performances having excellent control activity against wood pests. Therefore, among them, when the industrial material is treated with the industrial pest control agent of the present invention having both performances, two different effects of antibacterial effect and wood pest control effect can be obtained. By using the control agent, the processing effort can be halved and the processing cost can be reduced, which is very useful.
In addition, since the industrial pest control agent of the present invention having antibacterial activity has a very excellent antibacterial activity against bacteria, molds, yeasts, and algae, the industrial pest control agent of the present invention has various Can be applied to industrial products and industrial materials, for example, indoor and outdoor paint, rubber, fiber, resin, plastic, adhesive, jointing agent, sealing agent, building material, caulking agent, soil treatment agent, wood treatment agent, It can be added to white water, pigments, printing plate treatment liquid, cooling water, ink, cutting oil, nonwoven fabric, spinning oil, leather, etc. in the papermaking process as an additive that exhibits antibiotic activity.
Furthermore, since the industrial pest control agent of the present invention having wood pest control activity has excellent control activity against wood pests, it can be used as a wood pest control agent in soils and places where wood pests live. By applying, an excellent wood pest control effect can be obtained.
Moreover, since the plant extract used as an active ingredient in the present invention is derived from a natural product, it generally has little adverse effect on the environment.

Hereinafter, the industrial pest control agent of the present invention and the method for protecting industrial materials will be described in detail.
In addition, the pest in the present invention means fungi such as bacteria, fungi and yeast, algae and wood pests, which are problematic in industrial applications such as industrial products and industrial materials. The fungus that is a pest in the present invention may contain wood-decaying fungi, but a fungus that does not contain wood-decaying fungi is preferably the pest of the present invention.

The industrial pest control agent of the present invention comprises a plant extract as an active ingredient.
In the present invention, plants for obtaining components collected from plants include the genus Pongamia, the genus Calotropis, the genus Plumbago, the genus Maytenus, the genus Baccharis, the rubia ( Examples include at least one plant selected from the group consisting of plants belonging to the genus Rubia, the genus Calophyllum, the genus Artica, the genus Kobresia, and the genus Caesalpinia.
Examples of plants belonging to the genus Pongamia include Pongamia glabra.
Examples of plants belonging to the genus Calotropis include, for example, Calotropis gigantea. This carotropis gigantea (acon) is a shrub planted with dicotyledonous plants belonging to the genus Gagaidae, and the height reaches about 3 m.
Examples of plants belonging to the genus Plumbago include Plumbago zeylanica (Japanese name Ceylon pine).
Examples of plants belonging to the genus Maytenus include Maytenus ilicifolia. This Meynus ilicifolia is a plant belonging to the family Nymphalidae and is distributed in the southern part of South America.
Examples of plants belonging to the genus Baccharis include Baccharis genistelloides. Plants belonging to the genus Baccharis are shrubs with aromatic roots, yellow-white flowers at the head of inflorescences and a high resin content, and are distributed mainly in South America such as Brazil and Peru.
Examples of plants belonging to the genus Rubia include Rubia cordifolia.
Examples of plants belonging to the genus Calophyllum include Calophyllum inophyllum (Japanese name Terihaboku). This Carofilm / Innofilm is a plant belonging to the genus Terihaboku, which is distributed in Ogasawara, Ryukyu Islands, Taiwan, other tropical Asia, and Polynesia.
Examples of plants belonging to the genus Artica (Urtica) include Artica urens. This artica oolen is distributed in the temperate zone, and about 30 species are currently reported.
Examples of plants belonging to the genus Kobresia include Kobresia nepalensis.
Examples of plants belonging to the genus Caesalpinia include Caesalpinia ferrea Mart.

The plant extract of this invention means the composition which extracted the component which a plant body has by the conventional method. The site of use of the plant body to be used varies depending on the type of plant, but it may be the whole plant, for example, a root part (root, root bark, tuberous root, etc.), stem part (rhizome, tuber, Bulbs, strons, stems, branches, bark, stems, etc., leaves (leaves, petiole, etc.), flowers (flowers, foliage, sepals, florals, etc.), seeds (fruits, seeds, temporary seed coats, pericarps) Furthermore, it may be a non-volatile substance such as a resin secreted by a tree.
Moreover, as an extraction method, for example, after applying at least one treatment selected from drying, shredding, pulverization, etc. to plants, using a suitable extraction solvent under normal pressure or pressure, Extraction is performed at room temperature or under heating, and if necessary, filtered and then concentrated, etc., in order to increase extraction efficiency, use what has been subjected to treatment such as drying, freeze-drying, shredding, pulverization, etc. Is preferred. The obtained extract can be used alone or in combination of two or more. Moreover, you may use what is marketed as an extract as an active ingredient of this invention. In addition, as long as it is a known substance as a plant component, the substance can be obtained and used by a synthetic chemistry technique, or a commercially available substance can be used.

  As the extraction solvent, water, a hydrophilic solvent, a lipophilic solvent, and a mixture thereof can be used. As an extraction solvent, for example, water; methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, t-butanol, n-octanol, cyclohexanol, glycerin, ethylene glycol, propylene Alcohols such as glycols; chain ethers (eg, ethyl ether, propyl ether, isopropyl ether, dimethoxyethane, etc.), cyclic ethers (eg, dioxane, tetrahydrofuran, etc.), mono- or dialkylene glycol monoalkyl ethers (eg, ethylene glycol) Ethers such as cellosolves such as monomethyl ether and ethylene glycol monoethyl ether, and carbitols such as diethylene glycol monoethyl ether); Ketones such as seton, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; esters such as ethyl acetate, butyl acetate, diisononyl adipate (DINA), di-n-alkyl adipate (D610A), acetyl triethyl citrate and acetyl tributyl citrate Halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane and 1,2-dichloroethane; aliphatic hydrocarbons such as hexane and octane; alicyclic hydrocarbons such as cyclohexane and cycloheptane; benzene, toluene, Aromatic hydrocarbons such as xylene; Nitriles such as acetonitrile and benzonitrile; Carboxylic acids such as formic acid and acetic acid; N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, pyridine Etc. Any aprotic polar solvent. These solvents can be used alone or in combination.

Among these solvents, preferred hydrophilic solvents include linear or branched alcohols having about 1 to 4 carbon atoms; ketones such as acetone; nitriles such as acetonitrile; carboxylic acids; aprotic polar solvents and the like. included. Preferred lipophilic solvents include ketones such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; ethyl acetate, butyl acetate, diisononyl adipate (DINA), di-n-alkyl adipate (D610A), acetyl triethyl citrate, acetyl citrate Esters such as tributyl; Halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, and 1,2-dichloroethane; Aliphatic hydrocarbons such as hexane and octane; Alicyclic hydrocarbons such as cyclohexane and cycloheptane And aromatic hydrocarbons such as benzene, toluene and xylene are included.
Particularly preferred solvents are water; linear or branched alcohols having 1 to 4 carbon atoms as hydrophilic solvents, ketones such as acetone; esters such as ethyl acetate and diisononyl adipate (DINA) as lipophilic solvents. And halogenated hydrocarbons such as dichloromethane.

  The amount of the extraction solvent used may be in a range that does not impair the extraction efficiency and the extraction operation. Preferably it is about 100-2000 weight part. The extraction temperature is, for example, about 0 to 150 ° C., preferably about room temperature (for example, 25 ° C.) to about 120 ° C.

  The industrial pest control agent of the present invention may be formulated, for example, a liquid agent such as a solution, a wettable powder, a suspension, a dispersant, an emulsion, and an oil; a powder, a granule, and a microcapsule. Solid agents such as microspheres, flowable agents and foaming agents; semi-solid agents such as paste agents and creams; spray agents and aerosol agents; paints and the like, which can be appropriately selected depending on the purpose of use and application conditions. These preparations can be produced by conventional methods.

The liquid or semi-solid preparation can be produced, for example, by diluting a plant extract with an appropriate liquid diluent or carrier. In the case of a wettable powder, a solid diluent or a carrier may be further used.
As the liquid diluent or carrier, the same solvents as those exemplified as the solvent used for the extraction of plants can be used. For example, alcohols such as ethylene glycol, propylene glycol, glycerin, carbitols such as diethylene glycol monomethyl ether (methyl carbitol); petroleum solvents such as kerosene; ethyl naphthalene, phenylxylylethane, isopropyl biphenyl, diisopropyl biphenyl, etc. Aromatic hydrocarbons: Phosphate esters such as 2-ethylhexylphenyl phosphate, and the like, and plasticizers (for example, ester plasticizers such as di-2-ethylhexyl adipate) can be used in combination. These liquid diluents and carriers can be used alone or in combination. Examples of the solid diluent or carrier include diatomaceous earth, mica, clay, kaolin, talc, quartz powder, bentonite and the like. These solid diluents or carriers can also be used alone or in combination.
The solid preparation can be produced, for example, by diluting a plant extract with an appropriate solid diluent or carrier, or granulating. As the solid diluent or carrier, in addition to the solid diluent exemplified above, talc such as talc powder and wax stone powder, clays such as fine powder clay and mineral powder such as calcium carbonate; sulfur powder; urea powder; wood Examples include vegetable powders such as powder and starch; and various carriers commonly used for industrial control agents. These solid diluents and carriers are often used as bulking agents.
The aerosol can be produced, for example, by diluting a plant extract with an appropriate solvent as necessary and filling the container together with a propellant. Examples of the solvent include the solvents exemplified above. Examples of the propellant include Freon and liquefied natural gas.

  The industrial pest control agent of the present invention includes various additives as necessary, for example, stabilizers such as antioxidants and ultraviolet absorbers; binders; resins having film-forming ability; An emulsifier, a dispersant, a spreading agent, a wetting agent, a penetrating agent; a thickener; a flow aid; an anti-caking agent; an aggregating agent; an ultraviolet scattering agent; a moisture removing agent;

Examples of the antioxidant include 4,4′-thiobis-6-t-butyl-3-methylphenol, butylated hydroxyanisole (2-t-butyl-4-methoxyphenol and 3-t-butyl-4- A mixture of methoxyphenol), p-octylphenol, mono (or di or tri)-(α-methylbenzyl) phenol, 2,6-di-t-butyl-p-cresol (BHT), pentaerythrityl tetrakis [3- (3,5-di-t-butyl-4-hydroxyphenyl)] phenolic antioxidants such as propionate; amine antioxidants such as N, N′-di-2-naphthyl-p-phenylenediamine; Hydroquinoline antioxidants such as 1,5-di (t-amyl) hydroquinoline; Sulfur antioxidants such as dilauryl thiodipropionate Agents; such as phosphorus-based antioxidants such as triphenyl phosphite may be exemplified.
Examples of the ultraviolet absorber include benzotriazole compounds such as 2- (2′-hydroxy-5′-methylphenyl) benzotriazole and 2- (2′-hydroxy-4′-n-octoxyphenyl) benzotriazole. Benzophenone compounds such as 2-hydroxy-4-methoxybenzophenone and 2-hydroxy-4-n-octoxybenzophenone; salicylic acid compounds such as phenyl salicylate and pt-butylphenyl salicylate; 2-cyano-3,3; -2-ethylhexyl diphenyl acrylate, 2-ethoxy-2'-ethyl oxalic acid bisanilide, dimethyl-1- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensation Examples can be given.
Examples of the binder include carboxymethylcellulose sodium salt, methylcellulose, ethylcellulose, hydroxymethylcellulose, dextrin, pregelatinized starch, polyvinyl alcohol, polyvinylpyrrolidone, sodium lignin sulfonate, and potassium lignin sulfonate.
Examples of the resin having a film forming ability include polyolefins such as polyethylene and polypropylene, polyvinyl acetate, polyvinyl alcohol, acrylic resins, polyvinyl chloride, styrene resins, fluororesins, chlorinated polyolefins, alkyd resins, polyamides, polyesters, and the like. Thermosetting resins such as phenol resin, urea resin, melamine resin, furan resin, unsaturated polyester resin, epoxy resin, etc. can be illustrated, and these resins include all forms such as solvent type and emulsion type It is.

As the emulsifier, dispersant, spreading agent, wetting agent, and penetrating agent, conventional surfactants such as anionic surfactants and nonionic surfactants can be used. Examples of the anionic surfactant include metal soaps, sulfate ester salts such as alkyl sodium sulfate, alkylbenzene sulfonates such as sodium alkylbenzene sulfonate, sodium alkylnaphthalene sulfonate [for example, products manufactured by Takemoto Yushi Co., Ltd. Name: alkylnaphthalene sulfonate such as Newkalgen BX-C], dialkyl sodium 2-sulfosuccinate [for example, trade name; Neocor SW-C] manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd. , Polycarboxylic acid type surfactants [for example, Sanyo Chemical Industries, Ltd., trade name; Toxanone GR-30], α-olefin sulfonate, polyoxyethylene distyrenated phenyl ether sulfate ammonium salt [for example, No. 1 Made by Ichi Kogyo Seiyaku Co., Ltd., trade name; Kusuzoru 60A], sodium lignin sulfonate, potassium lignin sulfonate can be exemplified. Nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether [for example, trade name; Neugen EA-142, manufactured by Daiichi Kogyo Seiyaku Co., Ltd.], polyoxyethylene aryl ether, fatty acid Polyhydric alcohol ester, fatty acid polyhydric alcohol polyoxyethylene, sucrose fatty acid ester, block copolymer of ethylene oxide and propylene oxide [for example, Sanyo Chemical Industries, Ltd., trade name: New Pole PE-64], etc. Can be illustrated.
Examples of the thickener include polyvinyl alcohol, polyacrylic acid and salts thereof, and examples of the flow aid include PAP aid (for example, isopropyl phosphate), wax, polyethylene, fatty acid metal salt, paraffin, silicone. Examples thereof include organic lubricants such as oil and inorganic lubricants such as talc. Examples of the anti-caking agent include white carbon, diatomaceous earth, magnesium stearate, aluminum oxide, and titanium dioxide. Examples of the flocculant include liquid paraffin, ethylene glycol, diethylene glycol, triethylene glycol, and isobutylene polymer [for example, trade name: IP Solvent-2835 manufactured by Idemitsu Kosan Co., Ltd.]. Examples of the ultraviolet scattering agent include titanium dioxide. Examples of the moisture removing agent include desiccants such as anhydrous gypsum and silica gel powder. Examples of the colorant include organic or inorganic pigments and dyes.

  Furthermore, the industrial pest control agent of the present invention may contain a known antiseptic and fungicide, insect repellent, pest repellent, insect growth control agent, and efficacy enhancer.

Bacteria, fungi such as fungi and yeast, wood-rotting fungi, and algae that are controlled by the industrial pest control agent of the present invention are not particularly limited.
Examples of bacteria include gram negative bacteria and gram positive bacteria. Specific examples of gram-negative bacteria include the genus Escherichia, Pseudomonas, Burkholderia, Serratia, Klebsiella, Legionella, and Salmonella. Examples include bacteria such as (Salmonella), Enterobacter, Proteus, and Branhamella. Specific examples of Gram-positive bacteria include the genus Staphylococcus, Streptococcus, Bacillus, Clostridium, Enterococcus, Listeria, Coryne Examples include bacteria such as the genus Corynebacterium.
Examples of the mold include, for example, zygomycetes such as the genus Absidia, Mucor, and Rhizopus, such as the genus Ketomium, the genus Eurotium, and the genus Neurospora. , Gliocladium genus, Saccharomyces genus Ascomycetes, eg Acremonium genus, Alternaria genus, Aspergillus genus, Aureobasidium genus , Cladosporium genus, Fusarium genus, Penicillium genus, Phoma genus, Trichoderma genus, Rhodotorula genus, Candida genus, Trichophyton genus ) Incomplete fungi such as genera.
Examples of yeast include protozoan fungi such as Schizosaccharomyces genus, Protomyces genus, and Taphrina genus; elastocyst fungi such as Endomyces genus; Saccharomyces ( Saccharomyces genus Ascomycetes; Candida genus Ascomycete yeast incomplete form; Philobabasidiella genus basidiomycetes; Rhodotorula genus, Trichosporon genus , Sporobolomyces genus basidiomycetous yeast incomplete type; Rhodosporidium genus, Sporidiobolus genus, Xanthophyllomyces genus basidiomycetous yeast, etc. Is mentioned.
In addition, examples of the wood-rotting fungi include, for example, the genus Coniophora, the Trametes genus, the Postia genus, the Polya genus, the Gloeoophyllum genus, the Lentinus genus, the Paxilus ( Paxillus, Fomitopsis, Pleurotus, Donkioporia, Serpula, Glenospora, Perenniporia, Antrodia Etc. Wood decay fungi may or may not be included as a control target of the industrial pest control agent of the present invention.

  Algae are plants that inhabit water and land, have an assimilating pigment, and have an independent nutritional life. For example, cyanobacteria, gray algae, red algae, yellow flagellates, yellow-green algae, green algae Diatoms, brown flagellates, dinoflagellates, green flagellates, brown algae, green worms, axle algae, and the like. The industrial pest control agent of the present invention exhibits an algal control effect excellent in controlling cyanobacteria and green algae, among others. Examples of cyanobacteria include the genus Oscillatoria, the genus Phormidium, and the green algae include, for example, the genus Chlamydomonas, the genus Chlorococcum, the genus Chlorella, and the genus desmodesmus ( Examples include the genus Desmodesmus, the genus Klebsormidium, the genus Trebouxiophyceae, the genus Pleurococcus and the genus Ulothrix.

The wood pests to be controlled by the industrial pest control agent of the present invention are not particularly limited.
Examples of wood pests include insects belonging to termites, coleoptera, and bees. Specific examples of insects belonging to the termites are, for example, those belonging to the family termites, such as the termites (Coptotermes formosanus), the Yamato termites (Reticulitermes speratus), and those belonging to the Lepidoptera family such as the American white-tailed termites and the dairy termites Is mentioned. Specific examples of insects belonging to the order of the order Coleoptera include Hiratakakumuushi, Narahiratakekumuushi, zelkova larvae, Arahirahiratakekumuidae, etc. Those belonging to the beetle feed such as mushroom beetle, those belonging to the family Nagamushi beetle such as the cigarette beetle, Japanese bamboo beetle, Japanese pear beetle, large-footed beetle, those belonging to the power beetle family such as the tiger beetle, the weevil family such as the weevil Examples include those belonging to the family Beetleidae, such as sakusekikumushi, and others belonging to the family Buprestidae and Weevilidae. Specific examples of insects belonging to the order of bees include, for example, those belonging to the bee family, such as a wasp, and those belonging to the ant family, such as a muna ant.
The term “control of wood pests (control of wood pests and prevention of damage caused by wood pests)” is used to mean not only killing wood pests but also avoiding and inhibiting feeding.

  The industrial pest control agent of the present invention may be selected appropriately according to the type of microorganism to be controlled (bacteria, mold, yeast, algae, etc.), the type of wood pest, and the control period. It is used as a concentration of 10 mg to 500 g (total amount of active ingredients) / kg (product), preferably 100 mg to 100 g (total amount of active ingredients) / kg (product).

Hereinafter, the present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to these examples.
First, the preparation method of the active ingredient of the industrial pest control agent of this invention is shown. In the examples, unless otherwise specified, parts means parts by weight.

<Preparation method>
A resin (3 Kg) of Calotropis gigantea collected in India was immersed in acetone (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (53 g).
A resin (900 g) of Rubia cordifolia collected in India was immersed in acetone (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (20 g).
A resin (1 Kg) of Calophyllum inophyllum collected in Okinawa was immersed in acetone (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (100 g).
A resin (3 Kg) of Plumbago zeylanica collected in India was immersed in acetone (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (35 g).
A resin (463 g) of Artica urens collected in Peru was immersed in methanol (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (32 g).
A resin (880 g) of Maytenus ilicifolia collected in Brazil was immersed in methanol (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (80 g).
A Pongamia glabra resin (400 g) collected in India was immersed in acetone (18 L) for 1 month, and the solvent was distilled off to obtain an extract (15 g).
A Baccharis genistelloides resin (910 g) collected in Peru was immersed in methanol (18 L) for 1 month, and then the solvent was distilled off to obtain an extract (170 g).

  Next, test examples show that the plant extract of the present invention has antibacterial activity against bacteria, molds, yeasts, and algae.

<Evaluation of antibacterial and algal resistance>
Test sample Example 1: Calotropis gigantea
Example 2: Rubia cordifolia
Example 3: Calophyllum inophyllum
Example 4: Pongamia glabra
Example 5: Urtica urens
The following evaluation test was performed using the extract obtained in the above “preparation method”.
(1) Evaluation of antibacterial activity (antibacterial) Each of the above extract extracts was added to glucose broth medium (pH 6.0) using methanol as a diluent solvent so that the test concentration was 10 mg / mL (10000 ppm). . Thereafter, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), a bacterial suspension containing the bacteria described in Table 1 was inoculated, cultured at 33 ° C. for 18 hours, and observed for growth.
(2) Evaluation of antibacterial properties (antifungal and anti-yeast) In a glucose broth medium (pH 6.0) using methanol as a diluting solvent so that the test concentration of the above extract is 10 mg / mL (10000 ppm). Each was added. Thereafter, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), inoculated with a mold suspension containing yeast described in Table 1 and yeast, and cultured at 33 ° C. for 18 hours and at 28 ° C. for 2 days. The presence or absence of growth of each fungus after the culture was observed.
(3) Evaluation of anti-algae properties Each of the above extract extracts was added to an allene-modified medium (pH 8.0) using methanol as a diluent solvent so that the test concentration was 10 mg / mL (10000 ppm). Then, using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.), inoculate an algal suspension containing the algae listed in Table 1, and at an illumination intensity of 2500 Lx and an irradiation condition of 16 hours per day at 23 ° C. Cultured for 30 days. Thereafter, the presence or absence of growth of algae after culturing was observed.
In addition, in said evaluation (1)-(3), it was confirmed that the methanol used as a dilution solvent has no influence on the growth of bacteria.

The results are shown in Table 1.
“◯” in Table 1 means that antibacterial and algal control activity was recognized, and “−” means that the presence or absence of antibacterial activity could not be confirmed.

In Table 1, the details of the bacteria, molds, yeasts, and algae used in the antibacterial and algal control tests are described below.
<Bacteria>
Bacillus subtilis
Staphylococcus aureus
Escherichia coli
Pseudomonas aeruginosa
<Mold>
Penicillium citrinum
Cladosporium cladosporioides
Aureobasidium pullulans
Alternaria sp .: Alternaria sp.
Mucor spinescens: Mucor spinescens
Gliocladium virens
<Yeast>
Rhodotorula rubra
<Algae>
Chlorococcum echinozygotum: Chlorococcum echinozygotum
Chlorella vulgaris
Desmodesmus sp.
Urosthrix variabilis
Klebsormidium flaccidum
Pleurococcus sp.

From the results in Table 1, it was revealed that the industrial pest control agent of the present invention containing a plant extract as an active ingredient has a high control effect on bacteria, molds, yeasts, and algae. In particular, the extract of Rubia cordifolia (Example 2) and the extract of Pongamia glabra (Example 4) have a wide range of antibacterial and anti-algal spectrums and are practically used. I can expect.
From these results, it was confirmed that the industrial pest control agent of the present invention has excellent antibacterial and algal control activities.

<Evaluation of anti-termites>
(1) Test sample Example 6: Maytenus ilicifolia
Example 7: Pongamia glabra
Example 8: Calotropis gigantea
Example 9: Baccharis genistelloides
Example 10: Plumbago zeylanica
The extract obtained in the above “preparation method” was diluted with ethanol to prepare a concentration of 1 mg / mL (1000 ppm) to obtain various liquid control agents.
(2) Evaluation of anti-termites 40 μL of each liquid agent control agent of (1) above was dropped onto a filter paper having a diameter of about 12 mm (2 types, JIS P _3801-1995 ), and after air drying, the weight of the filter paper W _B ( g) was measured.
Next, a termite control test was started by introducing 50 termite ants and filter paper soaked with the above-mentioned liquid control agent into a glass bottle filled with 50 g of silica sand No. 5 having a water content of 8%. At that time, the opening of the glass bottle was closed with a lid (having a vent hole) so that the termites did not escape to the outside.
The behavior of the termites in the glass bottles for 22 days from the start of the termite control test (injection of the termites and the filter paper into the glass bottles) was measured, and the ratio of dead termites (death rate) was measured.
Moreover, the weight W _A (g) of the filter paper after the termination of the termite control test was measured, and the corrosion rate of the filter paper was measured by the following formula from the weight W _B (g) of the filter paper before the start of the test.
Corrosion rate (%) = (W _B −W _A ) / W _B × 100
As a control, a termite control test was conducted in the same manner as described above except that filter paper not soaked with the control agent was used instead of the filter paper soaked with the control agent.
The above termite control test was conducted, and the average value of the results is shown in Table 2 in accordance with the evaluation criteria of the dead insect rate and the damage rate shown below.

・ Death rate: Rate of dead termites I: 100%
II: 66.6% (two thirds) or more, less than 100% III: 33.3% (one third of the whole) or more, less than 66.6% IV: 2% (one head) or more, Less than 33.3% (1/3 of the total) V: Less than 2% (0 termites confirmed dead)

・ Eating damage rate: Area ratio of filter paper damaged by termites A: 0%
B: 1% or more, less than 20% C: 20% or more, less than 40% D: 40% or more, less than 60% E: 60% or more, less than 80% F: 80% or more, less than 100% G: 100%

From the results shown in Table 2, the industrial pest control agent of the present invention comprising a plant extract of the genus Meynus and Carotropis has an excellent termite control effect because it has high termicidal activity and no food damage. Became clear. In addition, the industrial pest control agent of the present invention, which contains a plant extract of the genus Pongamia, Buccaris, and Purumago, has a low termite killing activity but has no food damage over 22 days. It became clear that it was excellent.
From this result, it was confirmed that the industrial pest control agent of the present invention has an excellent termite control activity.

<Confirmation of active ingredients contained in plant extract>
(1) Test specimen Example 11: Isolation and purification of components contained in the extract of Plumbago zeylanica and confirmation of the structure thereof were performed.
Plumbago zeylanica bark (3 kg) collected in Bangalore, India was dipped in acetone (18 L) for about 1 month after powder cutting. The concentrate (35 g) was subjected to silica gel column chromatography and roughly fractionated with a chloroform: methanol system. The obtained fraction was further subjected to silica gel column chromatography, gel filtration chromatography (carrier: Sephadex LH-20) and high performance liquid chromatography (HPLC) to obtain the following 5 compounds as isolated and purified products.
Plumbagin (Plumbagin, 21mg, yellow powder)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.19 (3H, s), 6.81 (1H, d, J = 1.5Hz), 7.25 (1H, dd, J = 8.7, 1.5Hz), 7.60 (1H, t, J = 7.8Hz), 7.64 (1H, dd, J = 7.3,1.6Hz), 11.98 (1H, s)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ16.4, 115.2, 119.2, 124.1, 132.1, 135.4, 136.1, 149.6, 161.2, 184.7, 190.2
PZ2 (3-methylplumbagin, 6.2mg, yellow powder)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.17 (6H, s), 7.22 (1 H, dd, J = 8.2, 1.1 Hz), 7.57 (1 H, t, J = 7.8 Hz), 7.62 (1 H, dd, J = 7.4,1.1Hz), 12.18 (1H, s)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ 12.3, 13.0, 114.9, 118.9, 123.7, 132.1, 135.9, 143.2, 144.8, 161.1, 184.2, 190.2
PZ3 (13.3mg, yellow powder)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.13 (3H, s), 2.34 (3H, s), 3.80 (2H, s), 7.22 (1H, dd, J = 8.1, 1.4 Hz), 7.59 ( 1H, t, J = 8.0Hz), 7.64 (1H, dd, J = 7.4,1.4Hz), 11.95 (1H, s)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ13.4, 30.2, 41.1, 114.7, 119.2, 123.9, 132.1, 136.2, 140.3, 147.2, 161.3, 183.9, 189.1, 203.0
PZ20 (Diomuscinone, 3.7mg)
¹ H-NMR (400 MHz, CDCl ₃ ): δ1.24 (3H, s), 2.76 (1H, d, J = 17.4 Hz), 3.40 (1H, d, J = 17.0 Hz), 3.50 (1H, dd, J = 8.0,4.0Hz), 4.02 (1H, dd, J = 8.0,4.0Hz), 7.27 (1H, d, J = 9.2Hz), 7.56 (1H, d, J = 7.6Hz), 7.66 (1H, (t, J = 7.8Hz)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ21.4, 46.5, 50.5, 67.8, 117.5, 118.7, 124.0, 133.9, 137.0, 161.2, 200.9, 202.9
PZ22 (Citranone, 32.6mg, yellow powder)
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.07 (3H, s), 2.23 (3H, s), 6.86 (1H, s), 7.48 (1H, d, J = 8.6 Hz), 7.48 (1H, d, J = 7.7Hz), 7.64 (1H, t-like), 7.72 (1H, d, J = 7.3Hz), 7.76 (1H, d, J = 8.0Hz), 11.94 (1H, s), 12.29 ( 1H, s)
¹³ C-NMR (100 MHz, CDCl ₃ ): δ14.6, 16.5, 114.9, 115.2, 118.6, 119.3, 124.3, 128.6, 132.0, 132.4, 135.4, 136.3, 136.9, 141.3, 147.7, 149.9, 158.4, 161.5, 187.6 , 187.7, 184.1, 184.4
The chemical structures of the five compounds are shown below.

An antibacterial test was conducted on Plumbagin, one of the isolated and purified substances, to examine the minimum inhibitory concentration. For this study, the isolated and purified plumbagin was diluted with methanol to a concentration of 10 mg / mL (10000 ppm) to prepare a liquid control agent.
(1) Evaluation of antibacterial property (antibacterial) With respect to the above liquid agent control agent, sterilized water is used as a diluent solvent so that the concentration of plumbagin is in the range of 0.8 to 100 ppm. 0) respectively. Thereafter, using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.), a bacterial suspension containing the bacteria described in Table 3 was inoculated and cultured at 33 ° C. for 18 hours. Thereafter, the growth of the bacteria after culturing was observed, and the minimum inhibitory concentration (MIC: μg / mL) was calculated.
(2) Evaluation of antibacterial properties (antifungal, yeast-proof) For the above-mentioned liquid-controlling agent, a glucose bouillon medium prepared with sterilized water so that the concentration of plumbagin is in the range of 0.8 to 100 ppm. (PH 6.0), then, using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.), the mold suspension containing yeast described in Table 3 and a yeast were inoculated, and the mold was incubated at 33 ° C. for 18 hours. The culture was performed at 28 ° C. for 2 days. Thereafter, the growth of each bacterium after the culture was observed, and the minimum growth inhibitory concentration (MIC: μg / mL) was calculated.
The results are shown in Table 3.

In Table 3, the details of the bacteria, molds and yeast used in the minimum inhibitory concentration test are described below.
<Bacteria>
Bacillus subtilis
Staphylococcus aureus
Escherichia coli
<Mold>
Aspergillus niger
Penicillium citrinum
Cladosporium cladosporioides
Aureobasidium pullulans
Alternaria sp .: Alternaria sp.
Mucor spinescens: Mucor spinescens
Gliocladium virens
<Yeast>
Rhodotorula rubra
Saccharomyces cerevisiae: Saccharomyces cerevisiae

  From the results of Table 3, it was revealed that plumbagin contained in the extract of Plumbago zeylanica has excellent control activity against bacteria, fungi and yeast. In particular, since it is possible to prevent growth at a low concentration with respect to “Alternaria species” which is a problem in industrial use, it can be expected to be used practically.

Antibacterial activity was also tested for components other than plumbagin contained in the extract of Plumbago zeylanica.
(1) Test sample Example 12: PZ2
Example 13: PZ3
Example 14: PZ20
Example 15: PZ22
Each of these isolated and purified products was diluted with methanol and prepared to have a concentration of 1 mg / mL (1000 ppm) to obtain each test specimen.
(2) Evaluation of antibacterial activity (antibacterial) For each test specimen of (1) above, each isolated and purified product was prepared with methanol so that the concentration of the evaluation test conducted was 100 ppm, and glucose broth medium (pH 6.0) Respectively. Thereafter, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), a bacterial suspension containing the bacteria described in Table 4 was inoculated, cultured at 33 ° C. for 18 hours, and observed for growth.
(3) Evaluation of antibacterial properties (antifungal, anti-yeast) About each test specimen of the above (1), each isolated purified product was prepared with methanol so that the evaluation test concentration was 100 ppm, and glucose broth medium (pH 6) 0) respectively. Then, using a microplanter (manufactured by Sakuma Seisakusho Co., Ltd.), inoculating the mold suspension and yeast containing the mold described in Table 4, and culturing at 33 ° C. for 18 hours and at 28 ° C. for 2 days The presence or absence of growth of each fungus after the culture was observed.
In the above evaluations (2) and (3), it has been confirmed that methanol used as a dilution solvent does not affect the growth of bacteria.

The results are shown in Table 4.
“◯” in Table 4 means that antibacterial activity was observed, and “−” means that the presence or absence of antibacterial activity could not be confirmed.

In Table 4, the details of the bacteria, molds and yeasts used in the antibacterial test are described below.
<Bacteria>
Bacillus subtilis
Staphylococcus aureus
<Mold>
Cladosporium cladosporioides
Alternaria sp .: Alternaria sp.
Aureobasidium pullulans
<Yeast>
Rhodotorula rubra
Saccharomyces cerevisiae: Saccharomyces cerevisiae

  From the results of Table 4, it was revealed that the four component substances contained in the extract of Plumbago zeylanica have a high control effect on bacteria, molds and yeasts. In particular, since Example 12 (PZ2) and Example 15 (PZ22) can prevent growth at a low concentration with respect to “Alternaria species” which is a problem in industrial applications, utilization in practical use can be expected.

  The components contained in Kobresia nepalensis and Caesalpinia ferrea Mart. Were tested for antibacterial activity.

<Confirmation of active ingredients contained in plant extract>
Examples 16 to 17: Isolation and purification of components contained in an extract of Kobresia nepalensis and confirmation of the structure thereof were performed.
The above-ground part of Kobresia nepalensis collected at Hirayama Highland in Nepal was washed with water, air-dried (dry weight about 1.5 kg), and immersed in methanol (18 L) for 1 month. The concentrate (400 g) was fractionated into a hexane, ethyl acetate, and butanol soluble part, and the ethyl acetate soluble part (50 g) was subjected to silica gel column chromatography, and crude fractionation was performed with a chloroform: methanol system. For the obtained fraction, silica gel column, gel filtration chromatography (carrier: Sephadex LH-20) and high performance liquid chromatography (HPLC) were further repeated to obtain the following two compounds as isolated and purified products.
KN15 (ε-Viniferin, 40mg, yellow powder)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ4.48 (1H, d, J = 5.4Hz), 5.42 (1H, d, J = 5.4Hz), 6.24 (3H, s), 6.33 (1H, d, J = 2.0Hz), 6.71 (1H, d, J = 16.3Hz), 6.73 (1H, d, J = 2.0Hz), 6.74 (2H, d, J = 8.5Hz), 6.84 (2H, d, J = 8.5Hz), 6.91 (1H, d, J = 16.3Hz), 7.18 (2H, d, J = 8.6Hz), 7.21 (2H, d, J = 8.6Hz)
KN20 (α-Viniferin, 53mg, reddish brown powder)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ4.00 (1H, s), 4.62 (1H, d, J = 6.2Hz), 4.71 (1H, d, J = 6.2Hz), 4.91 (1H, d, J = 6.2Hz), 5.95 (1H, d, J = 6.2Hz), 6.00 (1H, d, J = 1.8Hz), 6.07 (1H, s), 6.22 (1H, d, J = 1.8Hz) , 6.24 (1H, d, J = 2.2Hz), 6.25 (1H, d, J = 1.8Hz), 6.61 (1H, d, J = 2.2Hz), 6.72 (1H, d, J = 1.8Hz), 6.72 (2H, d, J = 8.8Hz), 6.78 (2H, d, J = 8.8Hz), 6.79 (2H, d, J = 8.4Hz), 7.03 (2H, d, J = 8.8Hz), 7.05 (2H , d, J = 8.8Hz), 7.23 (2H, d, J = 8.4Hz)
¹³ C-NMR (100 MHz, CD ₃ COCD ₃ ): δ46.4, 52.8, 55.7, 86.4, 90.0, 95.1, 96.5 × 2, 96.9, 105.8, 106.2, 108.5, 115.7 × 2, 116.0 × 2, 116.1 × 2 , 118.8 × 2, 119.7, 128.1 × 2, 128.2 × 2, 128.7 × 2, 132.0, 132.3, 132.5, 138.7, 139.7, 141.2, 157.9, 158.2, 158.3, 159.3 × 2, 159.4, 160.9, 161.6, 161.7 (× 2: overlapping)

The chemical structures of the two compounds are shown below.

Examples 18 to 20: Isolation and purification of components contained in an extract of Caesalpinia ferrea Mart. And confirmation of the structure thereof were performed.
Bark (5 kg) of Caesalpinia ferrea Mart. Collected in the Brazilian Amazon was dipped in acetone (18 L) for 1 month after powder cutting. The concentrate (about 160 g) was fractionated into a hexane, ethyl acetate, and butanol soluble part, and the ethyl acetate soluble part (about 50 g) was subjected to silica gel column chromatography, and the fraction was roughly fractionated in a chloroform: methanol system. The obtained fraction was further subjected to silica gel column, gel filtration chromatography (carrier: Sephadex LH-20) and high performance liquid chromatography (HPLC) to obtain the following 3 compounds as isolated and purified products.
PF1 (Pauferrol B, 58.6mg, yellow powder)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ5.45 (1H, d, J = 6.4Hz), 5.96 (1H, d, J = 6.4Hz), 6.37 (1H, d, J = 2.2Hz) , 6.40 (1H, dd, J = 8.9,2.2Hz), 6.57 (1H, d, J = 8.9Hz), 6.89 (2H, d, J = 8.9Hz), 6.94 (2H, d, J = 8.9Hz) , 7.32 (2H, d, J = 8.9Hz), 7.77 (2H, d, J = 8.9Hz), 7.78 (1H, d, J = 8.9Hz), 7.82 (1H, d, J = 15.6Hz), 7.86 (1H, d, J = 15.6Hz), 8.28 (1H, d, J = 8.9Hz)
¹³ C-NMR (100 MHz, CD ₃ COCD ₃ ): δ55.0, 91.5, 102.6, 103.7, 109.1, 113.9, 114.3, 115.9, 116.5 × 2, 116.8 × 2, 118.3, 127.6, 128.8 × 2, 131.7, 132.0 × 2, 134.5, 134.5, 145.7, 159.0, 161.2, 162,6, 166.5, 167.1, 168.1, 193.3, 202.5 (× 2: overlapping)
PF2 (Pauferrol C, 20.3mg, yellow powder)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ5.37 (1H, d, J = 6.1Hz), 6.22 (1H, d, J = 6.1Hz), 6.43 (1H, d, J = 1.8Hz) , 6.44 (1H, s), 6.62 (1H, dd, J = 8.9,1.8Hz), 6.88 (2H, d, J = 8.6Hz), 6.92 (2H, d, J = 8.6Hz), 7.33 (2H, d, J = 8.6Hz), 7.49 (1H, d, J = 15.6Hz), 7.58 (2H, d, J = 8.6Hz), 7.78 (1H, d, J = 15.6Hz), 7.98 (1H, s) , 8.01 (1H, d, J = 8.9Hz)
¹³ C-NMR (100 MHz, CD ₃ COCD ₃ ): δ56.6, 89.2, 98.8, 104.0, 109.4, 113.4, 115.0, 116.5 × 2, 116.9 × 2, 118.0, 119.4 127.4, 128.2, 128.7 × 2, 131.6 × 2, 131.7, 134.8, 145.3, 158.9, 161.1, 166.7, 167.2, 167.4, 168.6, 192.6, 201.0 (× 2: overlapping)
PF4 (Pauferrol D, 7th-position epimer mixture, 18.4mg, yellow powder)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ 2.73 (1H, dd, J = 12.9,3.0Hz), 2.90 (1H, dd, J = 16.8,12.9Hz), 5.47 (1H, d, J = 6.7Hz), 5.48 (1H, dd, J = 16.8,3.0Hz), 6.02 (1H, d, J = 6.7Hz), 6.20 (1H, dd, J = 9.0,2.3Hz), 6.36 (1H, d , J = 2.3Hz), 6.66 (1H, d, J = 8.5Hz), 6.70 (2H, d, J = 8.5Hz), 6.88 (2H, d, J = 8.5Hz), 7.02 (2H, d, J = 8.5Hz), 7.31 (2H, d, J = 8.5Hz), 7.72 (1H, d, J = 9.0Hz), 7.83 (1H, d, J = 8.5Hz)
¹³ C-NMR (100 MHz, CD ₃ COCD ₃ ): δ 44.8, 55.1, 80.3, 91.2, 103.6, 105.0, 109.3, 113.9, 114.9, 115.9 × 2, 116.5 × 2, 116.6, 128.0 × 2, 128.7 × 2 , 130.6, 130.8, 131.6, 134.5, 158.1, 158.8, 159.5, 166.6, 167.0, 167.6, 190.1, 202.5 (× 2: overlapping)
¹ H-NMR (400 MHz, CD ₃ COCD ₃ ): δ2.77 (1H, dd, J = 12.9,3.0Hz), 3.01 (1H, dd, J = 16.8,12.9Hz), 5.35 (1H, dd, J = 16.8,3.0Hz), 5.45 (1H, d, J = 6.6Hz), 6.00 (1H, d, J = 6.6Hz), 6.18 (1H, dd, J = 9.0,2.4Hz), 6.32 (1H, d , J = 2.4Hz), 6.67 (1H, d, J = 8.5Hz), 6.73 (2H, d, J = 8.5Hz), 6.86 (2H, d, J = 8.5Hz), 7.10 (2H, d, J = 8.5Hz), 7.31 (2H, d, J = 8.5Hz), 7.68 (1H, d, J = 9.0Hz), 7.85 (1H, d, J = 8.5Hz)
¹³ C-NMR (100 MHz, CD ₃ COCD ₃ ): δ 43.9, 55.0, 80.5, 91.2, 103.6, 105.1, 109.2, 113.8, 114.9, 116.0 × 2, 116.5 × 2, 116.8, 128.5 × 2, 128.7 × 2 , 130.6, 130.7, 131.6, 134.4, 158.3, 158.9, 159.5, 166.5, 167.1, 167.7, 190.3, 202.5 (× 2: overlapping)

The chemical structures of the three compounds are shown below.

The obtained components were tested for antibacterial activity.
(1) Test specimen Example 16: KN15 (ε-Viniferin)
Example 17: KN20 (α-Viniferin)
Example 18: PF1 (Pauferrol B)
Example 19: PF2 (Pauferrol C)
Example 20: PF4 (Pauferrol D)
Each of these isolated and purified products was diluted with methanol and prepared to have a concentration of 1 mg / mL (1000 ppm) to obtain each test specimen.
(2) Evaluation of antibacterial activity (antibacterial) For each test specimen of (1) above, each isolated and purified product was prepared with methanol so that the concentration of the evaluation test conducted was 100 ppm, and glucose broth medium (pH 6.0) Respectively. Thereafter, using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.), a bacterial suspension containing the bacteria described in Table 5 was inoculated, cultured at 33 ° C. for 18 hours, and observed for growth.
(3) Evaluation of antibacterial properties (antifungal) For each test specimen of (1) above, each isolated and purified product was prepared with methanol so that the concentration of the evaluation test conducted was 100 ppm, and glucose broth medium (pH 6.0) Respectively. Then, using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.), a mold suspension containing the mold listed in Table 5 was inoculated, and cultured at 33 ° C. for 18 hours and at 28 ° C. for 2 days. The presence or absence of later growth of each fungus was observed.
In the above evaluations (2) and (3), it has been confirmed that methanol used as a dilution solvent does not affect the growth of bacteria.

The results are shown in Table 5.
“◯” in Table 5 means that antibacterial activity was observed, and “−” means that the presence or absence of antibacterial activity could not be confirmed.

In Table 5, the details of the bacteria and molds used in the antibacterial test are described below.
<Bacteria>
Bacillus subtilis
Staphylococcus aureus
<Mold>
Aureobasidium pullulans

  From the results in Table 5, it is clear that the component substances contained in the extract of Kobresia nepalensis and Caesalpinia ferrea Mart. Have a controlling effect on bacteria and mold. It was.

<Evaluation of algae resistance>
Test sample Example 21: Rubia cordifolia
Example 22: Pongamia glabra
Example 23: Calotropis gigantea
Example 24: Plumbago zeylanica
Example 25: Baccharis genistelloides
Example 26: Maytenus ilicifolia
The extract obtained in the above “preparation method” was diluted with methanol and prepared so that the evaluation test concentration was 1 mg / mL (1000 ppm), and each test specimen was obtained.
(1) Evaluation of anti-algae properties Each test sample is added to an allene-modified medium (pH 8.0), and then the algae described in Tables 6 to 8 are used using a micro planter (manufactured by Sakuma Seisakusho Co., Ltd.). The algae suspension contained was inoculated and cultured at 23 ° C. for 30 days under irradiation conditions of illuminance 2500 Lx and 16 hours per day. Thereafter, the presence or absence of growth of algae after culturing was observed.

The results are shown in Table 6.
“◯” in Tables 6 to 8 means that the algal control activity was recognized.

In Tables 6 to 8, the details of the algae used in the anti-algae test are described below.
<Algae>
Chlorococcum echinozygotum: Chlorococcum echinozygotum
Chlorella vulgaris
Desmodesmus sp.
Klebsormidium flaccidum
Urosthrix variabilis
Pleurococcus sp.

From the results of Tables 6 to 8, it was revealed that the industrial pest control agent of the present invention containing a plant extract as an active ingredient has a high control effect on algae. In particular, the extract of Rubia cordifolia (Example 21) has a wide alga-proof spectrum and can be expected to be used in practical use.
From this result, it was confirmed that the industrial pest control agent of the present invention has an excellent algal control activity.

  Since the industrial pest control agent of the present invention has an excellent control activity against bacteria, molds, yeasts, and algae and / or an excellent control activity against wood pests, the industrial pest control agent of the present invention By treating this, industrial materials can be protected efficiently, which is very useful. Moreover, since the industrial pest control agent of the present invention contains a plant extract derived from a natural product as an active ingredient, it is suitable for industrial use without worrying about corrosion of industrial materials.

Claims (7)

  An industrial pest control agent having at least one of antibacterial activity and wood pest control activity, comprising a plant extract as an active ingredient. 2. The industrial pest control according to claim 1, wherein the plant extract is an extract obtained from at least one plant selected from the group consisting of the following (1) to (10). Agent.
(1) The genus Pongamia (2) The genus Carotropis (3) The genus Plumbago (4) The genus Maytenus (5) The genus Baccharis (6) The genus Rubia (7 ) Genus Calophyllum (8) genus Artica (9) genus Kobresia (10) genus Caesalpinia   Both industrial antibacterial activity and wood pest control activity, characterized by containing as an active ingredient one or more plant extracts of the genus Pongamia, Calotropis, and Plumbago The industrial pest control agent according to claim 1 or 2, which has activity.   Plumamia (Pongamia) genus extract extract component of plumbagin as an active ingredient, which has both industrial antibacterial activity and wood pest control activity, according to any one of claims 1 to 3 The industrial pest control agent as described.   The industrial pest control agent according to claim 1 or 2, which has a wood pest control activity, comprising a plant extract of the genus Maytenus as an active ingredient.   A method for protecting industrial materials or industrial products, wherein the industrial pesticide according to any one of claims 1 to 5 is applied to industrial materials or industrial products. A compound represented by the following structural formula or an optically active isomer thereof.