Stink bug repellent
The use of 4-hydroxybenzoic acid esters with alkyl groups of 5 to 8 carbon atoms in stink bug repellents addresses the ineffectiveness and safety concerns of existing repellents, providing a safe and effective solution for repelling stink bugs in agricultural and household settings.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- UENO PHARMA CO LTD
- Filing Date
- 2024-10-29
- Publication Date
- 2026-05-15
AI Technical Summary
Existing stink bug repellents are either unsafe or ineffective in repelling stink bugs, and they emit odor compounds when threatened, posing health risks and failing to address the issue of stink bug infestation in both agricultural and household settings.
A stink bug repellent containing 4-hydroxybenzoic acid esters with alkyl groups of 5 to 8 carbon atoms, particularly n-hexyl 4-hydroxybenzoate and 2-ethylhexyl 4-hydroxybenzoate, which are applied through scattering, spraying, or coating to effectively repel stink bugs.
The repellent offers high safety and efficacy in repelling stink bugs, including species from the family Pentatomidae, with a sustained effect when used in combination, and can be formulated into various dosage forms for agricultural and household applications.
Smart Images
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Abstract
Description
Technical Field
[0001] The present invention relates to a stinkbug repellent containing a 4-hydroxybenzoic acid ester.
Background Art
[0002] Recently, various damages caused by a large outbreak of stinkbugs have been reported. For example, stinkbugs such as the brown-winged green stinkbug and the common green stinkbug breed in the cones of Cryptomeria japonica and Chamaecyparis obtusa, and then fly into orchards, causing great damage to fruit trees such as oranges, persimmons, and pears.
[0003] In addition, stinkbugs are particularly known as unpleasant pests among insects because of their strong odor. It has been found that the main components of the odor are aldehydes such as hexanal, and some of these compounds are irritating to the eyes, respiratory tract, skin, etc., so the risk of health damage has also been pointed out.
[0004] Stinkbugs have the habit of flying towards light at night (phototaxis) and preferring warm places. Therefore, especially after autumn, they are likely to enter houses as the sun sets. Therefore, countermeasures are required not only on farms but also in households. The large outbreak of stinkbugs is cited as one of the reasons that the warm winter due to global warming has made it easier for stinkbugs to overwinter, and it is considered that the damage will continue in the future.
[0005] Various means for controlling stinkbugs have been proposed. For example, a stinkbug control agent for houses containing a silane compound and a pyrethroid insecticide (Patent Document 1) and a stinkbug trapping device (Patent Document 2) have been proposed.
[0006] However, the insecticidal components are of low safety, and stinkbugs secrete odor components when they receive external stimuli such as an attack by an enemy. Therefore, the problem of odor has not been solved yet with insecticidal components and trapping devices.
[0007] Furthermore, while insect repellents containing hexyl 4-hydroxybenzoate are known to be effective against mites and slugs (Patent Document 3), their effectiveness against stink bugs was previously unknown. [Prior art documents] [Patent Documents]
[0008] [Patent Document 1] Japanese Patent Application Publication No. 8-059413 [Patent Document 2] Japanese Patent Publication No. 2017-143826 [Patent Document 3] Japanese Patent Publication No. 2019-69934 [Overview of the project] [Problems that the invention aims to solve]
[0009] The object of the present invention is to provide a stink bug repellent that is highly safe and highly effective at repelling stink bugs. Another object of the present invention is to provide a stink bug repellent method that is highly safe and highly effective at repelling stink bugs. [Means for solving the problem]
[0010] The inventors of this invention conducted thorough research on stink bug repellents and discovered that 4-hydroxybenzoic acid esters having alkyl esters with 5 to 8 carbon atoms have a high repellent effect against stink bugs, thus completing the present invention.
[0011] In other words, the present invention encompasses the following preferred embodiments. [1] Formula (1) TIFF2026078901000001.tif2055 [In the formula, R represents an alkyl group having 5 to 8 carbon atoms] A stink bug repellent containing 4-hydroxybenzoic acid ester represented by [formula]. [2] The stink bug repellent according to [1], wherein the 4-hydroxybenzoic acid ester represented by formula (1) is n-hexyl 4-hydroxybenzoate and / or 2-ethylhexyl 4-hydroxybenzoate. A method for repelling stink bugs, characterized by applying the stink bug repellent described in either [3], [1], or [2] to the target object or its surroundings. [4] The method for repelling stink bugs described in [3], wherein the repellent is applied to the target object by scattering, spraying, or coating. [Effects of the Invention]
[0012] The stink bug repellent of the present invention offers excellent safety and a high repellent effect against stink bugs. [Brief explanation of the drawing]
[0013] [Figure 1] This is a diagram showing a stink bug repellent test. [Modes for carrying out the invention]
[0014] The 4-hydroxybenzoic acid ester represented by formula (1) can be one or more selected from the group consisting of n-pentyl 4-hydroxybenzoate, n-hexyl 4-hydroxybenzoate, n-heptyl 4-hydroxybenzoate, n-octyl 4-hydroxybenzoate, and 2-ethylhexyl 4-hydroxybenzoate. Among these, n-hexyl 4-hydroxybenzoate and / or 2-ethylhexyl 4-hydroxybenzoate are preferred for their excellent stink bug repellent effect. These 4-hydroxybenzoic acid esters may be used alone or in combination of two or more. In particular, the combination of n-hexyl 4-hydroxybenzoate and 2-ethylhexyl 4-hydroxybenzoate is preferred due to its excellent sustained repellent effect. When 4-hydroxybenzoate n-hexyl and 4-hydroxybenzoate 2-ethylhexyl are used in combination, the content ratio of the two is preferably 1 to 99 / 99 to 1, more preferably 10 to 90 / 90 to 10, and even more preferably 20 to 80 / 80 to 20.
[0015] The 4-hydroxybenzoic acid ester represented by formula (1) used in the present invention may be a commercially available product, or it may be obtained by reacting 4-hydroxybenzoic acid with an alcohol in the presence of an acid catalyst, as described in Japanese Patent Application No. 2016-240132 previously proposed by the applicant of the present invention.
[0016] The stink bug repellent of the present invention contains a 4-hydroxybenzoic acid ester represented by formula (1) as an active ingredient. The 4-hydroxybenzoic acid ester represented by formula (1) can be dissolved or dispersed in various solvents, or mixed with or adsorbed to a solid carrier to prepare a dosage form such as an aerosol, pump, liquid, coating, mat, sheet, tape, powder, granule, gel, or cream, which can then be used as a stink bug repellent.
[0017] As the solvent, one or more of water, alcohols such as methyl alcohol and ethyl alcohol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, aliphatic hydrocarbons such as hexane, kerosene and paraffin, aromatic hydrocarbons such as benzene and toluene, and esters such as ethyl acetate and hexyl laurate can be used. Among these, acetone is preferable in terms of excellent solubility.
[0018] When the 4-hydroxybenzoic acid ester represented by the formula (1) is dissolved or dispersed in a solvent to obtain the stinkbug repellent of the present invention, the content of the 4-hydroxybenzoic acid ester represented by the formula (1) in the stinkbug repellent is preferably 0.1 to 50% by mass, more preferably 1 to 20% by mass, based on the mass of the stinkbug repellent.
[0019] Examples of the solid carrier include mineral or inorganic powders such as kaolin, talc, bentonite, clay, diatomaceous earth, calcium carbonate, silica, and zeolite; vegetable powders such as wood powder, soybean powder, wheat flour, and starch powder; plastics such as phenolic resin, polyamide, acrylic, and polyester; synthetic fibers made of the plastics; rubber such as polybutadiene or its powder; sublimable powders such as camphor, naphthalene, paradichlorobenzene, trioxane, cyclododecane, and adamantane; natural fibers such as linter and pulp; animal and plant fibers such as wool, cotton, and silk; and regenerated fibers such as rayon. Further, paper, non-woven fabric, etc. obtained from inorganic fibers such as glass fiber and asbestos can also be used as the solid carrier.
[0020] When the 4-hydroxybenzoic acid ester represented by the formula (1) is mixed or adsorbed with a solid carrier to obtain the stinkbug repellent of the present invention, the content of the 4-hydroxybenzoic acid ester represented by the formula (1) in the stinkbug repellent is preferably 0.1 to 50% by mass, more preferably 1 to 30% by mass, still more preferably 2 to 20% by mass, based on the mass of the stinkbug repellent.
[0021] The stinkbug repellent of the present invention may contain optional component A such as a film-forming agent, a surfactant, a wetting agent, a stabilizer, an aerosol, a bactericide, a fungicide, a fragrance, a water / oil repellent, etc., as necessary. Examples of the film-forming agent include ethyl cellulose, hydroxypropyl cellulose, silicone, acrylic resin, chlorinated rubber, petroleum resin, methyl cellulose, vinyl acetate, polyvinyl alcohol, latex emulsion, etc. Examples of the surfactant include aliphatic monocarboxylate, linear alkylbenzene sulfonate, alkyl sulfate, sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyethylene glycol fatty acid ester, fatty acid alkanolamide, etc. Examples of the wetting agent include casein, gelatin, alginic acid, carboxymethyl cellulose, etc. Examples of the aerosol include stabilizers such as butyl hydroxyanisole, dibutyl hydroxytoluene, tocopherol, γ-oryzanol, liquefied petroleum gas, dimethyl ether, fluorocarbon, compressed gas, etc. Examples of the bactericide include parachlorometaxylate, etc. Examples of the fragrance include lemon type, rose type, green type, etc. Examples of the water / oil repellent include wax, fats and oils, metal soap, fluorine-based oil repellent, etc.
[0022] When blending such optional component A, the blending amount is preferably 0.1 to 5% by mass, more preferably 0.2 to 4% by mass, and still more preferably 0.5 to 3% by mass with respect to the mass of the stinkbug repellent. The above-mentioned optional component A can be blended when preparing the above dosage form.
[0023] The stinkbug repellent of the present invention may contain, as necessary, optional component B such as other stinkbug control agents or repellents, etc. in addition to the 4-hydroxybenzoic acid ester represented by formula (1) for the purpose of enhancing the action of stinkbug repellency.
[0024] When such optional component B is included, its amount is preferably 1 to 80% by mass, more preferably 5 to 70% by mass, and even more preferably 8 to 65% by mass, relative to the mass of the 4-hydroxybenzoic acid ester represented by formula (1). The above optional component B can be included when preparing the above dosage form.
[0025] The stink bugs repelled by the stink bug repellent of the present invention are insects belonging to the order Hemiptera, suborder Heteroptera, and insects of the family Pentatomidae are particularly preferred to be repelled. Examples of insects in the Pentatomidae family include the brown marmorated stink bug (Plautia stali), the two-spotted stink bug (Laprius gastricus), the rice stink bug (Scotinophara lurida), the small stink bug (Scotinophara scotti), the large stink bug (Scotinophara horvathi), the white-margined stink bug (Aenaria lewisi), the rice stink bug (Niphe elongatus), the quail stink bug (Aelia fieberi), the white-spotted stink bug (Eysarcoris ventralis), the purple-spotted stink bug (Eysarcoris annnamita), the spiny-spotted stink bug (Eysarcoris aeneus), and the brown marmorated stink bug (Halyomorpha Halys), Yellow-spotted stink bug (Erthesina Fullo), Purple stink bug (Carpocoris purpureipennis), Spotted stink bug (Dolycoris baccarum), Scott's stink bug (Menida disjecta), White-spotted stink bug (Menida violacea), Medium-spotted stink bug (Menida musiva), Green stink bug (Nezara antennata), Southern green stink bug (Nezara viridula), Lined stink bug (Piezodorus hybneri), Shiny green stink bug (Glaucias subpunctatus), Hokkaido green stink bug (Plalomena angulosa), Horned green stink bug (Pentatoma japonica), Red-striped stink bug (Graphosoma Rubrolineatum), Agonascelis femoralis, Eurydema dominulus, Eurydema rugosa, Carbula abbreviate, Alcinorcoris japonensis, Pentatoma rufipes, LeliaThis includes one or more species selected from the group consisting of decempunctata, Picronerus lewisi, Picronerus bibens, Pintheaus sanguinipes, Arma custos, Zicrona caerulea, Andrallus spinidens, and Gonopsis affinis.
[0026] By applying the stink bug repellent of the present invention to an object or a designated part thereof (hereinafter simply referred to as the object) or its surroundings, stink bugs can be repelled from that object or its surroundings. Alternatively, the stink bug repellent may be supported on a carrier such as a nonwoven fabric, sheet, or inorganic carrier, and these may be placed in locations where stink bugs are to be repelled.
[0027] Applicable objects include, for example, the bottom or surrounding areas of flower pots, planters, and seedling pots, the space between the bottom and the soil, the inside of drainage holes, and under fallen leaves. Furthermore, organisms that can serve as a nutrient source for stink bugs, or their surrounding areas, are also included as applicable objects in this invention. Examples include agricultural crops themselves, the fields in which they are cultivated, orchards, and flowerbeds where flowers are grown.
[0028] In addition, suitable locations for applying stink bug repellents indoors include kitchens, bathrooms, balconies, and storage rooms in general households and restaurants.
[0029] Methods for applying the stink bug repellent of the present invention to the target object include scattering, spraying, or coating. The amount of the stink bug repellent of the present invention to be applied can be appropriately determined depending on the dosage form of the repellent, the method of application, and the location of application.
[0030] In the stink bug repellent of the present invention, the content of the 4-hydroxybenzoic acid ester represented by formula (1) can be appropriately determined depending on the dosage form, application method, and application location of the stink bug repellent. For example, when used as a liquid, such as in an aerosol concentrate or pump formulation, the stink bug repellent can preferably contain 0.1 to 50% by mass, more preferably 1 to 20% by mass, of the 4-hydroxybenzoic acid ester represented by formula (1). When used supported on a solid carrier such as a nonwoven fabric, the stink bug repellent can preferably contain 0.1% to 50% by mass, more preferably 1 to 30% by mass, and even more preferably 2 to 20% by mass, of the 4-hydroxybenzoic acid ester represented by formula (1). The solid carrier to be used can be arbitrarily selected from the above-mentioned materials, depending on the application location and method. [Examples]
[0031] The present invention will be described in detail below with reference to examples, but the present invention is not limited thereto. The stink bug repellents used in the examples and comparative examples are shown below. <Stink bug repellent> NPE: n-propyl 4-hydroxybenzoate (manufactured by Ueno Pharmaceutical Co., Ltd.) NBE: n-butyl 4-hydroxybenzoate (manufactured by Ueno Pharmaceutical Co., Ltd.) NHPB: n-hexyl 4-hydroxybenzoate (manufactured by Ueno Pharmaceutical Co., Ltd.) EHPB: 2-Ethylhexyl 4-Hydroxybenzoate (manufactured by Ueno Pharmaceutical Co., Ltd.) Carbon:(R)-(-)-Carbon (manufactured by Tokyo Chemical Industry Co., Ltd.)
[0032] <Stink bug repellent test> [Example 1] A 150mm diameter qualitative filter paper (ADVANTEC) was cut in half, and 1.1g of an acetone solution of NHPB, pre-adjusted to 10% w / w, was evenly dropped onto one side of the filter paper (treatment amount 10% w / w). After that, it was air-dried in a fume hood for 1 hour (NHPB-treated filter paper). In addition, a blank filter paper was prepared by dropping only acetone onto it in the same manner and drying it (blank filter paper).
[0033] To prevent stink bugs from attaching to the container, a plastic container (150mm in diameter x 65mm in height) had baby powder sprinkled on the inside of its sides. One sheet each of the NHPB-treated filter paper and blank filter paper were placed at two corners (diagonally opposite each other), and 0.25 mL of tap water was sprayed onto each sheet of filter paper. Ten brown stink bugs were released into the cup, and a lid with ventilation holes was placed over it. After the prescribed time had elapsed (at 5-minute intervals up to 60 minutes), the number of stink bugs on each sheet of filter paper was observed, and the repellency rate was calculated as follows. Repellency rate = [1 - (Number of insects invading the repellent-treated filter paper / Number of insects invading the blank filter paper)] × 100
[0034] The same test was conducted three times, and the average value was used as the avoidance rate for each time period. The repellency rate after 30 minutes is the average of the measurement results at each 5-minute interval (6 points) up to the 30-minute mark, and the repellency rate after 60 minutes is the average of the measurement results at each 5-minute interval (12 points) up to the 60-minute mark. The stink bug repellent test is shown in Figure 1, and the results are shown in Table 1.
[0035] [Example 2] A stink bug repellent test was conducted in the same manner as in Example 1, except that NHPB was replaced with EHPB. The results are shown in Table 1.
[0036] [Example 3] A stink bug repellent test was conducted in the same manner as in Example 1, except that the NHPB treatment amount of 10% w / w was changed to a combination treatment amount of 10% w / w of a paraben composition with NHPB:EHPB = 1:1 (weight ratio). The results are shown in Table 1.
[0037] [Comparative Example 1] A stink bug repellent test was conducted in the same manner as in Example 1, except that NHPB was changed to NPE. The results are shown in Table 1.
[0038] [Comparative Example 2] A stink bug repellent test was conducted in the same manner as in Example 1, except that NHPB was changed to NBE. The results are shown in Table 1.
[0039] [Comparative Example 3] A stink bug repellent test was conducted in the same manner as in Example 1, except that NHPB was replaced with carbon. The results are shown in Table 1.
[0040] [Table 1]
[0041] As is clear from the results in Table 1, the 4-hydroxybenzoic acid esters represented by formula (1) (Examples 1 and 2) exhibit excellent stink bug repellent effects and are understood to be useful as stink bug repellents. Furthermore, as shown in Example 3, it is understood that the stink bug repellent effect is synergistically improved, particularly in terms of persistence, when used in combination with other 4-hydroxybenzoic acid esters.
Claims
1. Formula (1) 【Chemistry 1】 [In the formula, R represents an alkyl group having 5 to 8 carbon atoms.] A stink bug repellent containing a 4-hydroxybenzoic acid ester represented by [formula].
2. The stink bug repellent according to claim 1, wherein the 4-hydroxybenzoic acid ester represented by formula (1) is 4-hydroxybenzoic acid n-hexyl and / or 4-hydroxybenzoic acid 2-ethylhexyl.
3. A method for repelling stink bugs, characterized by applying the stink bug repellent described in claim 1 or 2 to the target object or its surroundings.
4. The method for repelling stink bugs according to claim 3, wherein the repellent is applied to the target object by scattering, spraying, or coating.