CN111867379A - Pest repellent and pest repellent product - Google Patents

Pest repellent and pest repellent product Download PDF

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Publication number
CN111867379A
CN111867379A CN201980019218.2A CN201980019218A CN111867379A CN 111867379 A CN111867379 A CN 111867379A CN 201980019218 A CN201980019218 A CN 201980019218A CN 111867379 A CN111867379 A CN 111867379A
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repellent
pest
pest repellent
component
ants
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CN111867379B (en
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杉冈弘基
田村悠记子
引土知幸
川尻由美
中山幸治
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Great Japan Pyrethrum Corp
Dainihon Jochugiku Co Ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02Acyclic compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08Oxygen or sulfur directly attached to an aromatic ring system
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N49/00Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08Magnoliopsida [dicotyledons]
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention provides a pest repellent which has an effective repellent effect on specific exotic ants. An insect pest repellent containing a piperidine derivative represented by the following formula (I) as a repellent ingredient for solenopsis invicta and/or solenopsis tropica,

Description

Pest repellent and pest repellent product
Technical Field
The present invention relates to a pest repellent and a pest repellent product for repelling solenopsis invicta (Japanese: ヒアリ (Lebens)) and/or solenopsis tropica (Japanese: カミアリ (Lebens)).
Background
In recent years, pests designated as specific foreign organisms have been found in japan and become a significant social problem. As such specific foreign organisms, red imported fire ants and tropical imported fire ants are known, for example (hereinafter, collectively referred to as "specific foreign ants", however, in the present invention, argentina ants are not included in the specific foreign ants). The specific exotic ants are different from local ants, and have strong toxicity or high fertility. Therefore, when specific foreign ants are found, it is natural to completely repel them, but it is important that repelling measures be taken to prevent specific foreign ants from invading human living areas, which becomes an urgent need.
Conventionally, as an agent for repelling ants, for example, a repellent containing a natural essential oil as an active ingredient has been known (for example, see patent document 1). Patent document 1 describes, as active ingredients of ants repellents, oak moss, neroli oil (japanese: オレンジフラワー oil), sandalwood oil, spearmint oil, thyme white oil, patchouli oil, palmarosa oil, lemongrass oil, bay oil, garlic oil, rhinoceros oil, coconut oil, cinnamon leaf oil, dill seed oil (dill oil), thyme red oil, tolu oil, birch oil, and peru balsam.
Further, a method of controlling ants using a chemical such as mosquito repellent amine has been conventionally performed (for example, see patent document 2). While mosquito repellent amines are generally used as repellent ingredients for dipteran pests such as mosquitoes, according to patent document 2, hymenopteran pests such as ants are also cited as one of the target pests to be controlled.
Prior art documents
Patent document
Patent document 1: japanese patent laid-open publication No. 10-130114
Patent document 2: japanese patent application laid-open No. 2010-195766
Disclosure of Invention
Problems to be solved by the invention
However, specific foreign ants are ecologically very different from general local ants. Local ants, in addition to being underground, form colonies (nests) within the deadwood and carry out life activities in a relatively small number of familial units. On the other hand, specific exotic ants form colonies deep underground, and two kinds of ecology are known: in a community, there are a single queen que. Especially, the specific external ants with multiple queen-made ecology have higher fecundity when the number of the ants in the community is larger, and 4000 thousands of ants in one community can perform life activities.
As described above, since specific foreign ants are greatly different from local ants in terms of the scale of activity and the behavioral pattern, even when a repellent (active ingredient: natural essential oil) of ants described in patent document 1 or a control agent (active ingredient: mosquito repellent amine) described in patent document 2, which has been conventionally used, is applied to the colony of the specific foreign ants, the specific foreign ants cannot be completely repelled or repelled, and not only is there a possibility that some of the ants are quickly detected after emergence of the repellent or control agent, but also they are separated from the colony in order to evade the repellent effect or control effect thereof.
The present invention has been made in view of the above problems, and an object of the present invention is to provide a pest repellent and a pest repellent product which can effectively provide a repellent effect on a specific foreign ant.
Means for solving the problems
The pest repellent of the present invention for solving the above problems is characterized in that,
the repellent composition for solenopsis invicta and/or solenopsis tropica comprises a piperidine derivative represented by the following formula (I).
[ solution 1]
Figure BDA0002680895140000021
R: C2-C6 alkyl or alkoxy
According to the pest repellent of the present configuration, although the piperidine derivative represented by the above formula (I) has been known to exhibit a repellent effect against pests such as mosquitoes, gnats, butterfly flies, house flies, stable flies, cockroaches and the like, it is judged that the piperidine derivative can be an active ingredient (repellent ingredient) for repelling solenopsis invicta and/or tropical imported ants based on a new finding that the piperidine derivative exhibits an excellent repellent effect against specific foreign ants such as solenopsis invicta and tropical imported ants. Accordingly, the pest repellent containing the piperidine derivative of the present configuration is useful as a pest repellent for solenopsis invicta and/or solenopsis tropica, and when the pest repellent of the present configuration is used, damage caused by solenopsis invicta and/or solenopsis tropica can be reduced.
In the pest repellent of the present invention,
in the formula (I), R is preferably an alkoxy group having 2 to 6 carbon atoms.
According to the pest repellent of the present configuration, the alkoxy group having 2 to 6 carbon atoms is selected as the substituent R in the piperidine derivative represented by the formula (I), and thereby the pest repellent having a more excellent repellent effect against solenopsis invicta and/or solenopsis tropica can be provided.
In the pest repellent of the present invention,
the above R is preferably 1-methylpropyloxy.
According to the pest repellent of the present configuration, by selecting 1-methylpropyloxy as the substituent R in the piperidine derivative represented by the above formula (I), the piperidine derivative can be used as an epothilone having a high pest repellent effect and excellent safety to the human body, and can be a pest repellent having a more excellent repellent effect against red imported fire ants and/or tropical fire ants.
In the pest repellent of the present invention,
preferably further comprises at least one of the following (a) and (b) as a repellent fragrance component,
(a) c8-16 hydrocarbon aldehydes and/or ketones
(b) Monoterpene alcohols and/or aromatic alcohols having 8 to 12 carbon atoms in total.
According to the pest repellent of the present configuration, by further containing a repellent fragrance component of at least one of the above (a) and (b) in addition to the piperidine derivative represented by the above formula (I), it is possible to strongly repel solenopsis invicta and/or solenopsis tropica by utilizing the synergistic effect of the piperidine derivative and the repellent fragrance component. In addition, since the piperidine derivative is non-fragrant, when a repellent fragrance component is combined, the original fragrance of the repellent fragrance component is hardly affected at all. Accordingly, the piperidine derivative is a repellent component having good compatibility with a repellent fragrance component.
In the pest repellent of the present invention, it is preferable that,
the repellent fragrance component of the above (a) is at least one selected from the group consisting of decanal, undecanal, dodecanal, 2-methylundecanal, tridecanal, 10-undecenal, citronellal, citral, neral, phenylacetaldehyde, cinnamaldehyde, α -pentylcinnamaldehyde, α -hexylcinnamaldehyde, convallal, perillaldehyde, 3, 5-dimethyl-3-cyclohexene-1-formaldehyde (Japanese: トリベルタール), cuminaldehyde, piperonal, tridecanone, l-carvone, menthone, pulegone, cis-jasmone, dihydrojasmone, α -damascenone, β -damascenone, α -irisone, β -ionone, 2-pentylcyclopentanone, 2-hexylcyclopentanone, 2-heptylcyclopentanone, methylbenzylketone, and methylphenylketone,
the repellent fragrance component of the above (b) is at least one selected from the group consisting of linalool, dehydrolinalool, dihydromyrcenol, geraniol, nerol, citronellol, menthol, terpineol, terpinen-4-ol, isopulegol, borneol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, cinnamyl alcohol, thymol and eugenol.
According to the pest repellent of the present configuration, by selecting the repellent perfume component of the above (a) and the repellent perfume component of the above (b) from the above options, it is possible to provide a pest repellent capable of more strongly repelling solenopsis invicta and/or solenopsis tropicalis.
In the pest repellent of the present invention,
preferably, the repellent fragrance component (a) and the repellent fragrance component (b) are contained in a blending ratio (weight ratio) of 0.1/1 to 9/1.
According to the pest repellent of the present configuration, by containing the repellent fragrance component of the above (a) and the repellent fragrance component of the above (b) in the above blending ratio (weight ratio), a repellent effect (synergistic effect) enhanced by the different kinds of repellent fragrance components is obtained, and a pest repellent that is pleasant even with fragrance can be obtained.
In the pest repellent of the present invention,
it is preferable that the repellent further contains a glycol and/or a glycol ether as a repellent effect sustaining component.
In the pest repellent of the present invention, the glycols and/or glycol ethers have a higher vapor pressure than the piperidine derivative, and therefore the glycols and/or glycol ethers suppress excessive volatilization of the piperidine derivative. As a result, the repellent effect against solenopsis invicta and/or solenopsis tropica based on the piperidine derivative is sustained for a long period of time.
In the pest repellent of the present invention,
preferably, the composition contains substantially no insecticidal component.
According to the pest repellent of the present configuration, even if the pest repellent does not substantially contain an insecticidal component, a repellent effect against solenopsis invicta and/or solenopsis tropica can be obtained by the piperidine derivative represented by the above formula (I). Therefore, it is possible to make a pest repellent less resistant to daily use even for consumers allergic to the pesticidal component. Further, when the pests have become resistant to conventional repellent ingredients such as mosquito repellent amine, a repellent effect is also expected.
The pest repellent product of the present invention for solving the above problems is characterized in that,
the insect repellent is in the form of a liquid preparation, a gel preparation or a solid preparation containing any of the above insect repellents.
The pest-repellent product of the present invention contains the pest repellent of the present invention, and therefore is a practical and useful pest-repellent product for repelling solenopsis invicta and/or solenopsis tropica. Further, in the form of a product, a liquid preparation, a gel preparation, or a solid preparation is used, whereby an insect repellent product which is easy to use can be obtained.
Detailed Description
In the present invention, the present inventors have made extensive studies with respect to piperidine derivatives which have been known to exhibit a repellent effect against pests such as mosquitoes, gnats, butterfly flies, house flies, stable flies and cockroaches, and as a result, have found that these piperidine derivatives are unexpectedly superior in a repellent effect against specific exotic ants such as red fire ants and tropical fire ants which are now a problem in the society, and as a result, have finally completed pest repellents and pest repellent products against red fire ants and/or tropical fire ants. Hereinafter, the pest repellent and the pest repellent product of the present invention will be described. However, the present invention is not intended to be limited to the configurations of the following embodiments or the contents of the examples.
[ Pest repellents ]
The pest repellent of the present invention contains a piperidine derivative represented by the following formula (I) as a repellent ingredient for solenopsis invicta and/or solenopsis tropica.
[ solution 2]
Figure BDA0002680895140000051
R: C2-C6 alkyl or alkoxy
In the formula (I), R of the substituent is an alkyl group or an alkoxy group having 2 to 6 carbon atoms, but is preferably an alkoxy group having 2 to 6 carbon atoms.
When R is an alkyl group having 2 to 6 carbon atoms, the following are listed: ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl and the like. When R is an alkoxy group having 2 to 6 carbon atoms, the following are mentioned: ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, 1-methylpropoxy, 2-methylpropoxy and the like. Among these substituents R, the most preferable is 1-methylpropyloxy group in which R is alkoxy group having 4 carbon atoms, which is 1-methylpropyl 2- (2-hydroxyethyl) -1-piperidinecarboxylic acid ester represented by the following formula (II) [ alternative name: alcaprevin ].
[ solution 3]
Figure BDA0002680895140000061
The piperidine derivative represented by the above formula (I) has a slightly lower vapor pressure as an insect repellent component than that of conventionally, i.e., commonly used mosquito repellent amines. For example, the vapor pressure of the Escarlatine represented by the above formula (II) as a representative piperidine derivative is 0.059Pa (25 ℃ C.), and the vapor pressure of the mosquito repellent amine is 0.23Pa (25 ℃ C.). Nevertheless, as shown by the results of the examples described later, the pest repellent of the present invention containing a piperidine derivative exhibits an excellent repellent effect against specific exotic ants such as solenopsis invicta or solenopsis tropica. On the other hand, the conventional pest repellent containing the culicifumide has a remarkably deteriorated repellent effect on specific foreign ants, as compared with the pest repellent of the present invention containing the piperidine derivative. This is presumably because: the piperidine derivative has a greater repellent effect than a spatial repellent effect caused by volatilization of an active ingredient (repellent ingredient) against contact with an insect pest by the active ingredient.
In addition, the pest repellent of the present invention may exhibit practically problem-free repellent effects on specific foreign ants by containing only piperidine derivatives as an effective ingredient, but in the case of compensating for contact repellent effects by spatial repellent effects, it is possible to more strongly repel specific foreign ants by synergistic effects. Therefore, in the pest repellent of the present invention, in addition to the piperidine derivative represented by the above formula (I), it is effective to use a repellent fragrance component in combination. Since the piperidine derivative is non-fragrant (has no odor peculiar to an insect repellent), when it is combined with a repellent perfume component, it hardly affects the original fragrance of the repellent perfume component. Accordingly, the piperidine derivative is a repellent component having good compatibility with a repellent fragrance component.
The repellent perfume component capable of being combined with piperidine derivative comprises (a) hydrocarbon aldehydes and/or hydrocarbon ketones having 8-16 total carbon atoms and (b) monoterpene alcohols and/or aromatic alcohols having 8-12 total carbon atoms. The repellent fragrance component (a) and the repellent fragrance component (b) may be used alone or in combination.
Examples of the repellent fragrance component (a) include: decanal, undecanal, dodecanal, 2-methylundecanal, tridecanal, 10-undecenal, citronellal, citral, neral, phenylacetaldehyde, cinnamaldehyde, α -amyl cinnamaldehyde, α -hexyl cinnamaldehyde, convallaldehyde, perillaldehyde, 3, 5-dimethyl-3-cyclohexene-1-formaldehyde, cuminaldehyde, piperonal, tridecanone, l-carvone, menthone, pulegone, cis-jasmone, dihydro-jasmone, α -damascone, β -damascone, α -ionone, β -ionone, 2-amyl cyclopentanone, 2-hexyl cyclopentanone, 2-heptyl cyclopentanone, methyl benzyl ketone, and methyl styryl ketone. These repellent fragrance components of (a) may be used alone or in combination of a plurality of them.
Examples of the repellent perfume component (b) include: linalool, dehydrolinalool, dihydromyrcenol, geraniol, nerol, citronellol, menthol, terpineol, terpinen-4-ol, isopulegol, borneol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, cinnamyl alcohol, thymol and eugenol. These repellent fragrance components (b) may be used alone or in combination of two or more.
When the repellent perfume component (a) and the repellent perfume component (b) are used in combination, the blending ratio (a)/(b) is preferably set to 0.1/1 to 9/1, more preferably 0.5/1 to 1.4/1, in terms of weight ratio. When the blending ratio (a)/(b) is in the above range, a repellent effect (synergistic effect) enhanced by the different types of repellent fragrance components (a) and (b) is obtained, and it is pleasant even if fragrant. When the blending ratio (a)/(b) is smaller than 0.1/1 or when the blending ratio (a)/(b) is larger than 9/1, it becomes difficult to enjoy the synergistic effect by using the repellent perfume components (a) and (b) of different kinds in combination.
The pest repellent of the present invention may further contain (c) a hydrocarbon ester having 8 to 16 carbon atoms in total as a repellent fragrance component different from the above (a) and (b). The repellent perfume component of the above (c) is a component which can contribute to enhancing the repellent effect on a specific exotic ant in cooperation with the repellent perfume component of the above (a) and the repellent perfume component of the above (b).
Examples of the repellent perfume component (c) include: decyl acetate, linalyl acetate, geranyl acetate, citronellyl acetate, menthyl acetate, terpinyl acetate, neryl acetate, p-tert-butylcyclohexyl acetate, tricyclodecenyl propionate, tricyclodecenyl isobutyrate, benzyl acetate, phenylethyl acetate, styryl acetate, cinnamyl propionate, allyl hexanoate, allyl heptanoate, methyl benzoate, ethyl benzoate, 3-hexenyl benzoate, benzyl benzoate, methyl cinnamate, ethyl cinnamate, methyl salicylate, ethyl salicylate, pentyl salicylate, methyl jasmonate, and methyl dihydrojasmonate. These repellent fragrance components of (c) may be used alone or in combination of a plurality.
The pest repellent of the present invention may contain components other than the repellent fragrance component as necessary. Examples of such components include: hydrocarbons such as d-limonene, α -pinene and β -pinene, isoamylphenyl ethyl ether, linalool oxide, 1, 8-cineole, rose oxide (Japanese: ローズオキサイド), diphenyl ether, mackerel (Japanese: マグノラン), rhubarb furan (Japanese: ルバフラン), hydrocarbon ethers such as indanyl-2, 4-dioxane, nitrogen-containing compounds such as 2, 6-dimethyl-3-ethylpyrazine, citronellonitrile, stemonone (Japanese: ステモン) and o-aminoacetophenone, sandalwood oil and spearmint oil, essential oils such as thyme white oil, patchouli oil, garlic oil, cinnamon leaf oil, thyme red oil, jasmine oil, orange flower oil (Japanese: ネロリ oil), bergamot oil, orange oil, geranium oil, orange leaf oil, lemon oil, lemongrass oil, cinnamon oil, eucalyptus oil, and eucalyptus citriodora oil.
Further, it is effective that the pest repellent of the present invention contains glycols and/or glycol ethers. The glycols and/or glycol ethers function not only as a solvent for the repellent component or repellent fragrance component, but also as a repellent effect-sustaining component for sustaining the repellent effect of the repellent component or repellent fragrance component. The reason for this is that the glycols and/or glycol ethers have a higher vapor pressure than the piperidine derivative. When a glycol and/or a glycol ether is added to a piperidine derivative, excessive volatilization of the piperidine derivative is suppressed, and as a result, a repellent effect against a specific foreign ant based on the piperidine derivative can be sustained for a long period of time.
Examples of the glycols and/or glycol ethers that can be used as the repellent effect-sustaining component include: propylene glycol (10.7Pa), dipropylene glycol (1.3Pa), tripropylene glycol (0.67Pa), diethylene glycol (3Pa), triethylene glycol (1Pa), 1, 3-butanediol, hexanediol (6.7Pa), benzyl glycol (2.7Pa), diethylene glycol monobutyl ether (3Pa), dipropylene glycol monobutyl ether, and tripropylene glycol monomethyl ether. The parenthesized values described after the names of the respective substances are vapor pressures at 20 ℃. Among these glycols and/or glycol ethers, dipropylene glycol is a preferred repellent effect sustaining component. The content of the repellent effect-sustaining component is preferably 0.2 to 10 times the content of the repellent component and the repellent fragrance component.
In the pest repellent of the present invention, functional components such as deodorizing components, sterilizing components, antibacterial components and the like may be added if the substance or component does not interfere with the repellent effect of a specific foreign ant. The deodorant component is typically extract of plants of Gramineae, Theaceae, Ginkgoaceae, Oleaceae, Moraceae, Rutaceae, Saxifragaceae, and Ebenaceae. In addition, a relaxing effect can be provided by blending a so-called "green fragrance" such as geraniol or geranial.
The pest repellent of the present invention is preferably one that does not substantially contain an insecticidal component. The phrase "substantially not containing" does not mean that the content of the pesticidal component is strictly 0% in any case. For example, a case where an extremely small amount of an insecticidal component is unintentionally contained or a case where the effect as the insecticidal component is not exhibited even if the extremely small amount of the insecticidal component is intentionally contained may be regarded as an insect repellent containing substantially no insecticidal component. Examples of the case where an extremely small amount of an insecticidal component is unintentionally contained include: in the production equipment of the pest repellent, in the case of producing other products containing an insecticidal component in the past, an extremely small amount of the insecticidal component adhering to a container or a pipe is mixed as a contaminant into the pest repellent; examples of the insect repellent include those in which an insecticidal component floating or volatilizing in the air in the production room is absorbed into the insect repellent being produced and mixed. In such a case, even a case where the insect repellent contains an extremely small amount of an insecticidal component is regarded as an insect repellent containing substantially no insecticidal component.
Although the pest repellent of the present invention does not substantially contain an insecticidal component, the piperidine derivative as an essential component in the pest repellent of the present invention has a high repellent effect against specific foreign ants, and therefore exhibits a repellent effect equal to or greater than that of a repellent containing a conventional insecticidal component. Further, the pest repellent of the present invention containing substantially no insecticide can be a pest repellent having less resistance to daily use even for consumers allergic to the insecticide component. In addition, the pest repellent of the present invention can be expected to have a repellent effect even when the pest has become resistant to conventional repellent components such as mosquito repellent amine.
[ Pest-repellent preparations ]
The pest repellent of the present invention can be used for repelling a specific foreign ant without any special processing, but is prepared in an easy-to-use formulation and is practically used as a pest repellent product containing 0.01 to 99 w/w% of the pest repellent. The formulation of the pest repellent product is typically a liquid preparation, a gel preparation, or a solid preparation.
Examples of the liquid preparation and the gel preparation include a liquid preparation, an emulsion, an aqueous solvent, a microemulsion, an aerosol, and a cream. In the liquid preparation and the gel preparation, the contents of various components such as a repellent component, a repellent perfume component, and a repellent effect-sustaining component in the preparation can be easily adjusted. Therefore, there is an advantage that the commercial properties of the pest repellent product can be easily changed, for example, by increasing the repellent component to enhance the repellent effect, or by increasing the repellent perfume component to produce a product having high fragrance.
Examples of the solid agent include powders, granules, and baits. The solid agent has an advantage of easy handling since there is no risk of liquid leakage or fingertip wetting. The pest repellent product formed as a solid agent can be prepared, for example, by supporting (impregnating) a suitable carrier with the pest repellent. When the pest repellent is carried on the carrier, a solvent, a surfactant or the like may be added if necessary. Examples of the carrier include: examples of the thermoplastic resin include various vegetable powders such as wood flour and wheat flour, base fabrics such as paper, woven fabric and nonwoven fabric, porous organic molded products such as viscoseal (japanese: ビスコパール), inorganic carriers such as kaolin, talc, calcium carbonate, silica sand and ceramics, films or molded products made of polyethylene, polypropylene, ethylene/vinyl acetate copolymer (EVA), ethylene/methyl methacrylate copolymer (EMMA), styrene-based diblock polymer, styrene-based triblock polymer, thermoplastic resin elastomers (TPE and TPO), and silicone rubber. For example, when the carrier is a nonwoven fabric, the following are listed: a method for keeping the pest repellent by a liquid medicine distribution mode and a coating mode; or embedding with paraffin. In the case where the support is a film or a molded body, there may be mentioned: a method of retaining the pest repellent by a liquid medicine dispensing manner or a coating manner; or a method in which the insect repellent is sprayed or dropped together with a solvent to be impregnated into the film or the molded body. In the case where the carrier is silicone rubber, there may be mentioned: a method in which silicone rubber containing an insect repellent at a high concentration and untreated silicone rubber are put into a closed container, left for a certain period of time, and the concentration of the insect repellent is averaged over the entire silicone rubber.
The amount of the pest repellent to be incorporated in the pest repellent product is appropriately adjusted depending on the use, the period of use, the method, and the like of the pest repellent product, but is preferably 0.01 to 20 w/v% in the case of a liquid or gel preparation, and is preferably 0.01 to 10 w/w% in the case of a solid preparation. For example, in the case of a solid agent using a carrier, it is preferable that 10 to 50mg of the pest repellent is contained in each of the pest repellent products assuming a use period of 8 to 12 hours. In the pest repellent products assuming a use period of 15 to 30 days, it is preferable that each product contains 100 to 2000mg of the pest repellent.
When preparing the pest repellent product, a solvent, a surfactant, a cosolvent, a gelling agent, a dispersant, a stabilizer, a pH adjuster, a colorant, and the like may be added as required. Examples of the solvent include water, lower alcohols such as ethanol and isopropanol, ketone solvents, ester solvents, and hydrocarbon solvents such as normal paraffins and isoparaffins. Examples of the surfactant include: nonionic surfactants such as polyoxyethylene hydrogenated castor oil, polyoxyethylene higher alkyl ethers (polyoxyethylene lauryl ether, polyoxyethylene oleyl ether, etc.), polyoxyethylene alkylphenyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene polyoxypropylene alkyl ethers, etc., and higher alkylamine oxide surfactants such as laurylamine oxide, stearylamine oxide, laurylamidopropyldimethylamine oxide, etc. Examples of the gelling agent include polyvinyl alcohol, alginic acid, and carrageenan.
The pest repellent product of the present invention is used in a wide variety of fields depending on the formulation. Pest repellent products formed as liquid preparations are used, for example, as spray products to be spread on objects or the environment. Pest repellent products formed as gel preparations are used, for example, as coating products to be applied to the skin of a human body. Pest repellent products formed as solid agents are used by being spread or placed in a predetermined amount around doorways, kitchens, toilets, living rooms, bedrooms, warehouses, vehicles, balconies, porches, courtyards, houses, and the like. In particular, in the case where the pest-repellent article is a solid agent, since a three-dimensional barrier is formed so that specific foreign ants do not come close with the pest-repellent article as a center, the repellent effect can be exerted in a wide range. The insect repellent product formed by supporting the insect repellent on the molded body or the silicone rubber can be used by wrapping the insect repellent around an ankle, a shoe, or the like as a band, or by attaching the insect repellent to a shoe in the form of a fixing tool such as a clip. In the case of a pest repellent product formed by supporting a pest repellent on a sticker or a film, an adhesive layer may be provided on the lower surface of a carrier and the product may be used by attaching the product to the lower part of trousers or shoes.
The application amount of the pest-repellent product may be appropriately adjusted according to the formulation. In the liquid or gel preparation, the application amount is preferably 10 to 50mL/m2. The application amount is less than 10mL/m2In the case of the application, a sufficient repellent effect cannot be expected, and the application amount exceeds 50mL/m2In time, discomfort is increased due to stickiness. In the solid agent, the application amount is preferably 10-50 g/m2. The application amount is less than 10g/m2In the case of using the composition, a sufficient repellent effect cannot be expected, and the amount of the composition to be applied is more than 50g/m2It is not economical because the repelling effect is also hardly changed.
Examples
Next, examples of using the pest repellent and the pest repellent product of the present invention will be described. Various pest repellents of the present invention were prepared, and efficacy confirmation tests using local ants and specific foreign ants as subjects were carried out using them (examples 1 to 19). For comparison, the same efficacy confirmation test was also conducted on the conventional pest repellents (comparative examples 1 to 5). In the following examples, the weight unit of each component is expressed in mg, but the examples can be scaled up at any magnification. Accordingly, the unit of weight "mg" may be read as "parts by weight".
[ preparation of Pest repellent ]
Insect pest repellents of examples 1 to 19 and comparative examples 1 to 5 were prepared according to the compositions shown in table 1 below.
[ Table 1]
Figure BDA0002680895140000131
Here, regarding the piperidines a to f in table 1 as the pest repellent component, in the piperidine derivative represented by the above formula (I), the substituent R is a functional group shown in the following table 2.
[ Table 2]
Figure BDA0002680895140000141
As the piperidine a (escaroptin), piperidine b and piperidine d, commercially available pharmaceutical grade compounds were used. The piperidine c, the piperidine e and the piperidine f were synthesized by the present inventors through the following procedures.
[ piperidine c ]
2- (2-hydroxyethyl) -piperidine (715mg, 5.53mmol) and triethylamine (1.0ml, 7.21mmol) were dissolved in 6ml of toluene, and hexyl chloroformate (910mg, 5.53mmol) was added at 0 ℃. Subsequently, after stirring at 20 ℃ for 24 hours, the reaction solution was poured with water, and the organic component was extracted with ethyl acetate. Next, the organic layer containing the organic component was dried over magnesium sulfate, and then concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography to obtain piperidine c. The mass spectrum of piperidine c is shown below.
Colorless liquid: MS (EI) M/z [ M]+:257
[ piperidine e ]
Piperidine e was obtained by the same procedure except that decyl chloroformate was used instead of hexyl chloroformate in the synthesis of piperidine c. The mass spectrum of piperidine e is shown below.
Colorless liquid: MS (EI) M/z [ M]+:313
[ piperidine f ]
Piperidine f was obtained by the same procedure except that n-nonanoyl chloride was used instead of hexyl chloroformate in the synthesis of piperidine c. The mass spectrum of piperidine f is shown below.
Colorless liquid: MS (EI) M/z [ M]+:269
[ Effect confirmation test 1]
The pest repellents of examples 1 to 19 and comparative examples 1 to 5 were dissolved in 5mL of acetone, respectively, to prepare chemical solutions of the pest repellents. 0.3mL of each test solution was dropped on one half of a filter paper having a diameter of 15cm by using a sprayer and air-dried. In this case, in the filter paper after drying, for example, in example 1, the pest repellent contained 3.0mg on each half side of the filter paper. Then, the filter paper was placed in a glass petri dish with a diameter of 15cm in such a manner that the half face of the filter paper containing the pest repellent (treatment area) was not overlapped with the half face of the filter paper not containing the pest repellent (non-treatment area). Then, talc was applied to the inner wall of the glass petri dish, 30 japanese termites (one of local ants) or tropical fire ants (one of specific exotic ants) were placed as test insects, respectively, and the number of ants (number of insects) present in the treated area and the untreated area after 5 minutes and 2 hours was counted. Then, the pest repellency was determined according to the following formula.
The repellency rate (%) - (number of insects in non-treated area-number of insects in treated area)/number of test insects × 100
The efficacy confirmation test 1 was performed 3 times, and the average of the number of insects counted in each test was used for the calculation of the repellency rate. The test results are shown in table 3 below.
[ Table 3]
Figure BDA0002680895140000161
According to the results of the above efficacy confirmation test 1, when the pest repellent containing the piperidine derivative represented by the above formula (I) was used, a repellent effect that a imported fire ant tropica, which is one of specific foreign ants, did not come close was obtained from immediately after the test (after 5 minutes). The high repellent effect was substantially maintained even after 2 hours had elapsed (examples 1 to 19). It was confirmed that, even with respect to a termite, which is a kind of local ants, the same effect as that of a imported fire ant was obtained (examples 1 to 19). In particular, among the piperidine derivatives represented by the formula (I), compounds in which the substituent R is an alkoxy group having 2 to 6 carbon atoms are excellent in repellent effect, and compounds in which the substituent R is a 1-methylpropoxy group (Ecatin) are further excellent in repellent effect.
In more detail, as shown by the results of examples 5 to 8 and examples 9 to 19, it was confirmed that: the pest repellent contains, as a repellent perfume component, at least one of (a) hydrocarbon aldehydes and/or hydrocarbon ketones having 8 to 16 total carbon atoms and (b) monoterpene alcohols and/or aromatic alcohols having 8 to 12 total carbon atoms, in addition to the pest repellent component, and has an improved repellent effect (synergistic effect) as compared with a pest repellent containing only the pest repellent component. Moreover, according to the present embodiment, it was confirmed that: the blending ratio [ (a)/(b) ] of the repellent perfume component (a) and the repellent perfume component (b) is in the range of 0.1/1-9/1, thereby exhibiting a high repellent effect. In addition, from the comparison of example 12 with example 16 and the comparison of example 15 with example 17, it was confirmed that: when dipropylene glycol is added, the effect of sustaining the repellent effect of the pest repellent component can be obtained.
On the other hand, as shown in the results of comparative examples 1 to 5, it was confirmed that: conventional pest repellents comprising a compound other than the piperidine derivative represented by the above formula (I) and a mosquito repellent amine widely used as a repellent for human bodies are not only unable to exhibit a sufficient repellent effect against ants, but also tend to exhibit a considerably deteriorated repellent effect against tropical fire ants as compared with that against japanese termites.
[ Effect confirmation test 2]
Efficacy effect test 2 was carried out using a chemical solution of the pest repellent prepared by dissolving the pest repellent of each of examples 1, 5 to 14, 18 and comparative examples 1 to 5 in 5mL of acetone, by the same procedure as the efficacy confirmation test 1 described above, with the target red imported fire ant (a specific type of exotic ant). However, the number of ants (number of insects) present in the treated area and the untreated area was counted only after 5 minutes. The method of calculating the pest repellency rate was the same as that in efficacy confirmation test 1. The test results are shown in table 4 below.
[ Table 4]
Figure BDA0002680895140000181
According to the results of the efficacy confirmation test 2, when the pest repellent containing the piperidine derivative represented by the above formula (I), particularly the compound (ecarotene) in which the substituent R is 1-methylpropoxy group, is used, an excellent repellent effect is obtained also on the solenopsis invicta, which is one of specific exotic ants, from immediately after the test (after 5 minutes).
Further, as shown in the results of examples 5 to 8, it was confirmed that: the pest repellent contains, as a repellent perfume component, at least one of (a) hydrocarbon aldehydes and/or hydrocarbon ketones having 8 to 16 total carbon atoms and (b) monoterpene alcohols and/or aromatic alcohols having 8 to 12 total carbon atoms, in addition to the pest repellent component, and has an improved repellent effect (synergistic effect) as compared with a pest repellent containing only the pest repellent component. In addition, a comparison of example 5 with example 6 and a comparison of example 7 with example 8 confirmed that: the pest repellent containing alpha-hexyl cinnamic aldehyde as the repellent perfume component has a significantly improved repellent effect compared to a pest repellent not containing alpha-hexyl cinnamic aldehyde.
On the other hand, as shown in the results of comparative examples 1 to 5, the conventional pest repellent containing the above-mentioned compound other than the piperidine derivative represented by the formula (I) and the mosquito repellent amine which is widely used as a repellent for human body was also a result of deterioration of the repellent effect against red imported fire ants.
As described above, the pest repellent containing the piperidine derivative represented by formula (I) of the present invention exhibits a repellent effect equivalent to or more than that of local ants against specific foreign ants, which is a particularly remarkable property that could not be achieved by conventional ant repellents, and thus the usefulness and the practicability of the pest repellent of the present invention are proved to be high.
[ examples of the composition of insect-repellent articles ]
Next, a description will be given of a configuration example of a pest repellent product using the pest repellent of the present invention.
[ spray product (liquid preparation) ]
As the pest repellent component, a pest repellent containing 8.0g (4.0 w/v%) of Escarlatine represented by the above formula (II), 1.0g (0.5 w/v%) of cuminaldehyde and 2-pentylcyclopentanone as the repellent fragrance components of (a), 2.0g (1.0 w/v%) of l-menthol and 2-phenylethyl alcohol as the repellent fragrance components of (b), 0.2g (0.1 w/v%) of isopropylmethylphenol, and 1.0g (0.5 w/v%) of a deodorizing component derived from a persimmon extract was prepared. To this pest repellent, 110g (55 w/v%) of 99% ethanol and purified water were added to make the total amount 200mL, and a pump spray container was filled to prepare a spray-type pest repellent product (product a).
For the above product A, the subject was carefully sprayed over the jacket and pants (to the extent that the surface felt a little moisture, about 20mL/1 m) before going to the seaside (region where red imported fire ant inhabited)2) Especially on the cuffs and the lower part of the trousers. In the state of wearing clothes, the ant is walked at seaside for about 5 hours, but not only is not disturbed by specific external ants such as red imported fire ant, but also is not disturbed by local ants and other pests, and tick is not attached.
[ coated article (gel preparation) ]
As the pest repellent component, a pest repellent containing 3.0g (5.0 w/w%) of escitalopram represented by the above formula (II), 3.0g (5.0 w/w%) of 1, 3-butanediol as a repellent effect sustaining component, and 0.12g (0.2 w/w%) of ethylhexyl p-methoxycinnamate as an ultraviolet deterioration inhibiting component was prepared. To this insect repellent, 0.09g (0.15 w/w%) of carboxyvinyl polymer as a gel base, 0.09g (0.15 w/w%) of triethanolamine as a gelling agent, 21g (35 w/w%) of ethanol, and purified water were added, and the total amount was set to 60g, and the gel-type insect repellent product (product B) without perfume was filled in a gel discharge container.
Further, to the insect repellent used in the above-mentioned product B, 0.6g (1.0 w/w%) of dihydrojasmone as a repellent fragrance component of (a) and 0.6g (1.0 w/w%) of l-phenylethyl alcohol and dihydromyrcenol as repellent fragrance components of (B) were added, and a gel-type insect repellent (product C) aromatized with a repellent fragrance was prepared by formulating the other components in the same manner as the insect repellent used in the product B.
2 rods having a diameter of about 4cm and a length of 1m were prepared, and 20g/m of the total length of the rods was placed above the rods from the vicinity of the center (50cm) of each rod 2The coating amount of (3) coats article B. In addition, the other bar was coated with the same coating amount of the product C. When the actions of the red fire ants are observed by inserting two sticks into the nest into which the red fire ants frequently enter and exit, the turning-back actions are observed until the red fire ants climb to the vicinity of the center of the stick for either stick. Moreover, product C is faster than product B with respect to the action (folding back to nest) of the red fire ant. As described above, it was revealed that the ekatin exhibits a high repellent effect against specific exotic ants such as red imported fire ants, and in addition, it was confirmed that the repellent effect (synergistic effect) against specific exotic ants is enhanced by using the repellent perfume component of (a) in combination with the repellent perfume component of (b) and the ekatin.
Industrial applicability
The pest repellent and the pest repellent product of the present invention are particularly useful for the purpose of repelling and controlling specific foreign ants, and can be used not only as a household repellent or repellent product, but also as a business repellent or repellent product.

Claims (9)

1. An insect pest repellent containing a piperidine derivative represented by the following formula (I) as a repellent ingredient for solenopsis invicta and/or solenopsis tropica,
Figure FDA0002680895130000011
r: an alkyl group or an alkoxy group having 2 to 6 carbon atoms.
2. The pest repellent according to claim 1, wherein in the formula (I), R is an alkoxy group having 2 to 6 carbon atoms.
3. The pest repellent according to claim 2, wherein R is 1-methylpropoxy.
4. The pest repellent according to any one of claims 1 to 3, further comprising at least one of the following (a) and (b) as a repellent fragrance component,
(a) c8-16 hydrocarbon aldehydes and/or ketones
(b) Monoterpene alcohols and/or aromatic alcohols having 8 to 12 carbon atoms in total.
5. The pest repellent of claim 4, wherein the repellent fragrance ingredient of (a) is at least one selected from the group consisting of decanal, undecanal, dodecanal, 2-methylundecanal, tridecanal, 10-undecenal, citronellal, citral, neral, phenylacetaldehyde, cinnamaldehyde, α -amylcinnamaldehyde, α -hexylcinnamaldehyde, lilial, perillaldehyde, 3, 5-dimethyl-3-cyclohexene-1-formaldehyde, cuminaldehyde, piperonal, tridecanone, l-carvone, menthone, pulegone, cis-jasmone, dihydrojasmone, α -damascenone, β -damascenone, α -ionone, β -ionone, 2-pentylcyclopentanone, 2-hexylcyclopentanone, 2-heptylcyclopentanone, methylbenzylketone, and methylphenylketone,
The repellent fragrance component of (b) is at least one selected from the group consisting of linalool, dehydrolinalool, dihydromyrcenol, geraniol, nerol, citronellol, menthol, terpineol, terpinen-4-ol, isopulegol, borneol, 1-phenylethyl alcohol, 2-phenylethyl alcohol, cinnamyl alcohol, thymol and eugenol.
6. The pest repellent according to claim 4 or 5, which comprises the repellent fragrance component of (a) and the repellent fragrance component of (b) in a weight ratio (a)/(b) of 0.1/1 to 9/1.
7. The pest repellent according to any one of claims 1 to 6, further comprising a glycol and/or a glycol ether as a repellent effect sustaining component.
8. The pest repellent according to any one of claims 1 to 7, which is substantially free of an insecticidal component.
9. An insect repellent product comprising the insect repellent according to any one of claims 1 to 8 in the form of a liquid preparation, a gel preparation, or a solid preparation.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116076501A (en) * 2022-12-01 2023-05-09 华南农业大学 Plant-source repellent and application thereof in repelling tropical bed bugs and solenopsis invicta
CN116569921A (en) * 2023-07-05 2023-08-11 广东省林业科学研究院 Application of menthyl acetate in repelling solenopsis invicta

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102511332B1 (en) 2020-11-24 2023-03-16 동의과학대학교산학협력단 Composition of noxious insect repellent and disinfectant, manufacturing method thereof and composition of noxious insect repellent and disinfectant manufactured by the method
CN113558073B (en) * 2021-08-31 2022-04-01 王浦 Botanical pesticide for preventing and controlling pests and preparation method and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63174982A (en) * 1987-01-16 1988-07-19 Nitto Electric Ind Co Ltd Novel optically active epoxy ester
CN1441637A (en) * 2000-07-14 2003-09-10 拜尔公司 Compositions for repelling crawling insects
CN1845671A (en) * 2003-09-05 2006-10-11 波塞顿海洋科技公司 Menthol propylenglycol-carbonate and analogs thereof as insect pest repellents
US20130183390A1 (en) * 2008-04-02 2013-07-18 Bayer Cropscience Lp Synergistic pesticide compositions
CN104185620A (en) * 2012-03-13 2014-12-03 Redx药品有限公司 Agricultural chemicals
JP2019034906A (en) * 2017-08-18 2019-03-07 大日本除蟲菊株式会社 Ant repellent composition, and ant repellent product using the same
JP2019064982A (en) * 2017-10-04 2019-04-25 大日本除蟲菊株式会社 Ant control agent

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3848412B2 (en) 1996-10-31 2006-11-22 フマキラー株式会社 Ant repellent
JP2010195766A (en) 2009-01-29 2010-09-09 Sds Biotech Corp Method for controlling pyrethroid-resistant insect pest
JP6009934B2 (en) * 2012-12-26 2016-10-19 アース製薬株式会社 Gastropod pest repellent method and gastropod pest repellent composition
TWI662895B (en) * 2015-11-30 2019-06-21 日商大日本除蟲菊股份有限公司 Insect pest repellent composition in powder form, and method for producing same
JP2017114770A (en) * 2015-12-21 2017-06-29 国立大学法人 東京大学 Pest repellent
JP6814382B2 (en) 2016-02-22 2021-01-20 日油株式会社 Pest repellent composition
KR102083252B1 (en) * 2016-03-31 2020-03-02 다이니혼 죠츄기쿠 가부시키가이샤 Emergency pest avoidance products and emergency pest avoidance methods
WO2018012595A1 (en) * 2016-07-15 2018-01-18 ライオン株式会社 Pest repellent composition, and method for repelling pests

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63174982A (en) * 1987-01-16 1988-07-19 Nitto Electric Ind Co Ltd Novel optically active epoxy ester
CN1441637A (en) * 2000-07-14 2003-09-10 拜尔公司 Compositions for repelling crawling insects
CN1845671A (en) * 2003-09-05 2006-10-11 波塞顿海洋科技公司 Menthol propylenglycol-carbonate and analogs thereof as insect pest repellents
US20130183390A1 (en) * 2008-04-02 2013-07-18 Bayer Cropscience Lp Synergistic pesticide compositions
CN104185620A (en) * 2012-03-13 2014-12-03 Redx药品有限公司 Agricultural chemicals
JP2019034906A (en) * 2017-08-18 2019-03-07 大日本除蟲菊株式会社 Ant repellent composition, and ant repellent product using the same
JP2019064982A (en) * 2017-10-04 2019-04-25 大日本除蟲菊株式会社 Ant control agent

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116076501A (en) * 2022-12-01 2023-05-09 华南农业大学 Plant-source repellent and application thereof in repelling tropical bed bugs and solenopsis invicta
CN116569921A (en) * 2023-07-05 2023-08-11 广东省林业科学研究院 Application of menthyl acetate in repelling solenopsis invicta
CN116569921B (en) * 2023-07-05 2023-09-15 广东省林业科学研究院 Application of menthyl acetate in repelling solenopsis invicta

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