AU2019253406B2 - Insect pest repellent and insect pest repellent product - Google Patents

Insect pest repellent and insect pest repellent product Download PDF

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AU2019253406B2
AU2019253406B2 AU2019253406A AU2019253406A AU2019253406B2 AU 2019253406 B2 AU2019253406 B2 AU 2019253406B2 AU 2019253406 A AU2019253406 A AU 2019253406A AU 2019253406 A AU2019253406 A AU 2019253406A AU 2019253406 B2 AU2019253406 B2 AU 2019253406B2
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repellent
insect pest
pest repellent
component
ants
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AU2019253406A1 (en
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Tomoyuki Hikitsuchi
Yumi Kawajiri
Koji Nakayama
Hiroki Sugioka
Yukiko Tamura
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Dainihon Jochugiku Co Ltd
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Dainihon Jochugiku Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, 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
    • A01N35/02—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N35/00—Biocides, 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
    • A01N35/06—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N49/00—Biocides, 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • Y—GENERAL 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against 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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  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
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  • Natural Medicines & Medicinal Plants (AREA)
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  • Mycology (AREA)
  • Insects & Arthropods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Provided is a noxious insect repellent that can effectively repel invasive alien ants. A noxious insect repellent that contains a piperidine derivative that is represented by formula (I) as a component for repelling fire ants/red imported fire ants. In formula (I), R is preferably a C2–6 alkoxy group and is more preferably a 1-methyl propoxy group. The noxious insect repellant preferably also contains (a) and/or (b) as a repellent fragrance component: (a) a hydrocarbon aldehyde and/or a hydrocarbon ketone that has a total of 8–16 carbons; (b) a monoterpene alcohol and/or an aromatic alcohol that has a total of 8–12 carbons.

Description

DESCRIPTION INSECT PEST REPELLENT AND INSECT PEST REPELLENT PRODUCT TECHNICAL FIELD
[0001]
The present invention relates to an insect pest
repellent and insect pest repellent product for repelling fire
ants.
BACKGROUND ART
[0002]
Insect pests listed as specific invasive-alien species
have in recent years been found in Japan and posed a serious
social issue. As such specific alien species, for example,
known are fire ants (including red imported fire ants
(Solenopsis invicta) and tropical fire ants (Solenopsis
geminata)) (also hereinafter collectively referred to as
"specific invasive-alien ants," provided that Argentine ants
are not included in the specific invasive-alien ants herein).
The specific invasive-alien ants, which are species different
from domestic ants, are characterized by having strong toxins
and high reproductive power. Therefore, once the specific
invasive-alien ants have been found, it is natural that they
should be completely eradicated, and it is important to take
repellent measures to prevent the specific invasive-alien ants from invading human habitations, which is urgently necessary.
[00031
As a conventional chemical agent for repelling ants, for
example, repellents containing natural essential oil as an
active component are known (e.g., see Patent Document 1).
Patent Document 1 discloses, as active components for ant
repellents, oakmoss, orange flower oil, sandalwood oil,
spearmint oil, thyme white oil, patchouli oil, palmarosa oil,
lemongrass oil, laurel oil, garlic oil, Osmanthus fragrans
var. aurantiacus oil, coconut oil, cinnamon leaf oil, dill oil
(Anethum graveolens oil), thyme red oil, tolu balsam, birch
oil, and peru balsam.
[0004]
A method of controlling ants using a chemical agent such
as DEET has been conventionally conducted (see, for example,
Patent Document 2). DEET is commonly used as a repellent
component for insect pests of the order Diptera, such as
mosquitoes. Patent Document 2 indicates that insect pests of
the order Hymenoptera, such as ants, are also included in
insect pests to be controlled by DEET.
CITATION LIST PATENT LITERATURE
[00051
Patent Document 1: Japanese Unexamined Patent
Application Publication No. H10-130114
Patent Document 2: Japanese Unexamined Patent
Application Publication No. 2010-195766
SUMMARY OF INVENTION TECHNICAL PROBLEM
[00061
Incidentally, the specific invasive-alien ants have
nature significantly different from that of common domestic
ants. Domestic ants form a colony (nest) in the ground, inside
logs, and the like, and live on a family-by-family basis, each
family including a relatively small number of members.
Meanwhile, the specific invasive-alien ants form a colony deep
in the ground, and live in two known forms, i.e., a monogyne
form in which a colony contains a single queen, and a polygyne
form in which a colony contains multiple queens. In
particular, for the specific invasive-alien ants having a
polygyne form, the larger the number of queens in the colony,
the greater the reproductive power. Up to 40 million ants may
live in a single polygyne colony.
[0007]
Thus, the activity scale and behavioral pattern of the
specific invasive-alien ants are much different from those of
domestic ants. Therefore, even if the conventional ant
repellent (active component: natural essential oil) disclosed
in Patent Document 1 or the conventional control agent (active
component: DEET) disclosed in Patent Document 2 is applied to the colonies of the specific invasive-alien ants, the specific invasive-alien ants cannot always be completely repelled or controlled. In worse case, some of the queen ants are likely to quickly detect the presence of the repellent or control agent, and leave their colony in order to escape the repellent or control effect.
[00081
With the above problems in mind, the present invention
has been made. In some embodiments, the present invention
advantageously provides an insect pest repellent and insect
pest repellent product that are effective in repelling the
specific invasive-alien ants.
[00091
In some embodiments, an insect pest repellent according
to the present invention is characterized by comprising, as a
repellent component for fire ants, a piperidine derivative
represented by formula (I):
[Chemical Formula 1]
N CH2CH20H (I)
R: alkyl group or alkoxy group having 2-6 carbon atoms.
[0010]
For the insect pest repellent thus configured, it was found that the piperidine derivative represented by formula
(I), which is conventionally known as having a repellent
effect on insect pests such as mosquitoes, black flies, drain
flies, houseflies, stable flies, and cockroaches, also has an
excellent repellent effect on specific invasive-alien ants
such as fire ants, and based on such a novel finding, it was
demonstrated that the piperidine derivative represented by
formula (I) can serve as an active component (repellent
component) for repelling fire ants. Therefore, the insect pest
repellent thus configured to contain this piperidine
derivative is useful as an insect pest repellent for fire
ants, and can be used to reduce damage caused by fire ants.
[0011]
In the insect pest repellent of the present invention,
in formula (I), R is preferably an alkoxy group having 2-6
carbon atoms.
[0012]
For the insect pest repellent thus configured, an alkoxy
group having 2-6 carbon atoms is selected as the substituent R
in the piperidine derivative represented by formula (I),
whereby the insect pest repellent can have an excellent
repellent effect on fire ants.
[0013]
In the insect pest repellent of the present invention, R
is preferably a 1-methyl propoxy group.
[0014]
For the insect pest repellent thus configured, a 1
methyl propoxy group is selected as the substituent R in the
piperidine derivative represented by formula (I), whereby the
piperidine derivative is icaridin, which has a high insect
pest repellent effect and is highly safe for humans, and the
insect pest repellent can have a more excellent repellent
effect on fire ants.
[0015]
The insect pest repellent of the present invention
preferably further comprises, as a repellent fragrance
component, at least one of:
(a) a hydrocarbon aldehyde and/or hydrocarbon ketone
having a total of 8-16 carbon atoms; or
(b) a monoterpene alcohol and/or aromatic alcohol having
a total of 8-12 carbon atoms.
[0016]
The insect pest repellent thus configured contains, in
addition to the piperidine derivative represented by formula
(I), at least one of the repellent fragrance components (a) or
the repellent fragrance components (b). Therefore, the
synergistic effect of the piperidine derivative and the
repellent fragrance component can more effectively repel fire
ants. In addition, the piperidine derivative is smell-free.
Therefore, in the case where the piperidine derivative is
combined with the repellent fragrance component, the inherent
fragrance of the repellent fragrance component is not substantially affected. Therefore, it can be said that the piperidine derivative is a repellent component compatible with the repellent fragrance component.
[0017]
In the insect pest repellent of the present invention,
the repellent fragrance component (a) is preferably at least
one selected from the group consisting of decanal, undecanal,
dodecanal, 2-methyl undecanal, tridecanal, 10-undecenal,
citronellal, citral, neral, phenylacetaldehyde, cinnamic
aldehyde, a-amylcinnamic aldehyde, a-hexylcinnamic aldehyde,
lilial, perillaldehyde, trivertal, cuminaldehyde, heliotropin,
tridecanone, 1-carvone, menthone, pulegone, cis-jasmone,
dihydrojasmone, a-damascone, B-damascone, 5-damascone, a
ionone, B-ionone, 2-pentylcyclopentanone, 2
hexylcyclopentanone, 2-heptylcyclopentanone, methyl benzyl
ketone, and methyl styryl ketone, and
the repellent fragrance component (b) is preferably at
least one selected from the group consisting of linalool,
dehydrolinalool, dihydromyrcenol, geraniol, nerol,
citronellol, menthol, terpineol, terpinen-4-ol, isopulegol,
borneol, 1-phenylethylalcohol, 2-phenylethylalcohol, cinnamic
alcohol, thymol, and eugenol.
[0018]
For the insect pest repellent thus configured, the
repellent fragrance components (a) and (b) are selected from
the above options, which allows the insect pest repellent to more effectively repel fire ants.
[0019]
In the insect pest repellent of the present invention,
the blend ratio (weight ratio) (a)/(b) of the repellent
fragrance components (a) and (b) is preferably 0.1/1 to 9/1.
[0020]
The insect pest repellent thus configured contains the
repellent fragrance components (a) and (b) at the above blend
ratio (weight ratio), resulting in an enhanced repellent
effect (synergistic effect) by different types of repellent
fragrance components, and a pleasant fragrance.
[0021]
The insect pest repellent of the present invention
preferably further comprises, as a repellent effect-sustaining
component, a glycol and/or a glycol ether.
[0022]
For the insect pest repellent thus configured, the
glycol and/or glycol ether have a higher vapor pressure than
that of the piperidine derivative, and therefore, inhibit the
excessive vaporization and diffusion of the piperidine
derivative, so that the repellent effect of the piperidine
derivative on the specific invasive-alien ants can be
sustained over a long period of time.
[0023]
The insect pest repellent of the present invention is
preferably substantially free from insecticidal components.
[00241
The insect pest repellent thus configured, which is
substantially free from insecticidal components, has a
repellent effect on fire ants due to the piperidine derivative
represented by formula (I). Therefore, consumers who are
hypersensitive to an insecticidal component will not hesitate
to use the insect pest repellent in everyday life.
Furthermore, even when an insect pest becomes resistant to a
conventional repellent component such as DEET, the insect pest
repellent will be expected to have a repellent effect on such
an insect pest.
[0025]
In some embodiments, an insect pest repellent product
according to the present invention is characterized by
comprising any one of the above insect pest repellents, and in
that the insect pest repellent product is in the form of
liquid formulation, gel formulation, or solid formulation.
[0026]
The insect pest repellent product thus configured
contains the insect pest repellent of the present invention,
and therefore, serves as a practical and useful insect pest
repellent product for repelling fire ants. In addition, the
insect pest repellent product in the form of liquid
formulation, gel formulation, or solid formulation can be
highly convenient.
DESCRIPTION OF EMBODIMENTS
[00271
The present inventors have extensively studied
piperidine derivatives that are conventionally known as having
a repellent effect on insect pests such as mosquitoes, black
flies, drain flies, houseflies, stable flies, and cockroaches
to unexpectedly find that such piperidine derivatives have an
excellent specific repellent effect on the specific invasive
alien ants, i.e., fire ants and the like, which currently pose
a social issue. Based on such a novel finding, the present
inventors have arrived at an insect pest repellent and insect
pest repellent product for fire ants. An insect pest repellent
and insect pest repellent product according to the present
invention will now be described. Note that the present
invention is in no way limited to configurations of
embodiments below or details of examples below.
[0028]
[Insect Pest Repellent]
An insect pest repellent according to the present
invention contains, as a repellent component for fire ants, a
piperidine derivative represented by formula (I):
[Chemical Formula 2]
N CH2CH2OH (I)
00-R R:alkyl group or alkoxy group having 2-6 carbon atoms
In formula (I), R, which is a substituent, represents an alkyl
group or alkoxy group having 2-6 carbon atoms, preferably an
alkoxy group having 2-6 carbon atoms.
[0029]
Examples of R that is an alkyl group having 2-6 carbon
atoms include an ethyl group, n-propyl group, isopropyl group,
n-butyl group, sec-butyl group, isobutyl group, tert-butyl
group, pentyl group, and hexyl group. Examples of R that is an
alkoxy group having 2-6 carbon atoms include an ethoxy group,
n-propoxy group, isopropoxy group, n-butoxy group, tert-butoxy
group, 1-methyl propoxy group, and 2-methyl propoxy group. Of
these substituents R, a 1-methyl propoxy group, which is an
alkoxy group having four carbon atoms, is most preferable. In
this case, the piperidine derivative is 1-methylpropyl 2-(2
hydroxyethyl)-1-piperidinecarboxylate [another name:
icaridin], represented by formula (II):
[Chemical Formula 3]
N CH2CH2OH (II) CO-OCHCH2CH3
CH3
[0030]
The piperidine derivative represented by formula (I) has
a slightly lower vapor pressure than that of DEET, which is
conventionally commonly used as an insect pest repellent
component. For example, the vapor pressure of icaridin, which is a representative piperidine derivative represented by formula (II), is 0.059 Pa (250C), while the vapor pressure of
DEET is 0.23 Pa (25°C). Despite this, as can be seen from
results described below in examples, the insect pest repellent
of the present invention containing the piperidine derivative
had an excellent repellent effect on the specific invasive
alien ants including fire ants. Meanwhile, the repellent
effect of a conventional insect pest repellent containing DEET
on the specific invasive-alien ants was significantly lower
than that of the insect pest repellent of the present
invention containing the piperidine derivative. This is
considered to be because the repellent effect of the
piperidine derivative is more attributed to a contact
repellent effect caused by contact of the active component
with the insect pests, than to a spatial repellent effect
caused by vaporization and diffusion of the active component
(repellent component).
[0031]
Incidentally, even in the case where the insect pest
repellent of the present invention contains only the
piperidine derivative as an active component, the insect pest
repellent of the present invention can have a repellent effect
on the specific invasive-alien ants without a practical
problem. If the contact repellent effect is supplemented by a
spatial repellent effect, the resultant synergistic effect can
repel the specific invasive-alien ants more effectively.
Therefore, in the insect pest repellent of the present
invention, the piperidine derivative represented by formula
(I) is advantageously used in conjunction with a repellent
fragrance component. Note that the piperidine derivative is
smell-free (no odor peculiar to insect repellent agents), and
therefore, when the piperidine derivative is combined with a
repellent fragrance component, the inherent fragrance of the
repellent fragrance component is not substantially affected.
Therefore, it can be said that the piperidine derivative is a
repellent component compatible with a repellent fragrance
component.
[0032]
The repellent fragrance component that can be combined
with the piperidine derivative includes: (a) hydrocarbon
aldehydes and/or hydrocarbon ketones having a total of 8-16
carbon atoms; and (b) monoterpene alcohols and/or aromatic
alcohols having a total of 8-12 carbon atoms. Either or both
of the repellent fragrance components (a) and the repellent
fragrance components (b) can be used.
[0033]
Examples of the repellent fragrance components (a)
include decanal, undecanal, dodecanal, 2-methyl undecanal,
tridecanal, 10-undecenal, citronellal, citral, neral,
phenylacetaldehyde, cinnamic aldehyde, a-amylcinnamic
aldehyde, a-hexylcinnamic aldehyde, lilial, perillaldehyde,
trivertal, cuminaldehyde, heliotropin, tridecanone, 1-carvone, menthone, pulegone, cis-jasmone, dihydrojasmone, a-damascone,
-damascone, 5-damascone, a-ionone, -ionone, 2
pentylcyclopentanone, 2-hexylcyclopentanone, 2
heptylcyclopentanone, methyl benzyl ketone, and methyl styryl
ketone. These repellent fragrance components (a) may be used
alone or in combination.
[0034]
Examples of the repellent fragrance components (b)
incude linalool, dehydrolinalool, dihydromyrcenol, geraniol,
nerol, citronellol, menthol, terpineol, terpinen-4-ol,
isopulegol, borneol, 1-phenylethylalcohol, 2
phenylethylalcohol, cinnamic alcohol, thymol, and eugenol.
These repellent fragrance components (b) may be used alone or
in combination.
[0035]
In the case where the repellent fragrance components (a)
and (b) are used together, the blend ratio (a)/(b) by weight
of these components is preferably 0.1/1 to 9/1, more
preferably 0.5/1 to 1.4/1. If the blend ratio (a)/(b) is in
the above range, these different types of repellent fragrance
components (a) and (b) together provide an enhanced repellent
effect (synergistic effect), and a pleasant fragrance. If the
blend ratio (a)/(b) is smaller than 0.1/1, or the blend ratio
(a)/(b) is greater than 9/1, the combination of these
different types of repellent fragrance components (a) and (b)
is less likely to provide a synergistic effect.
[00361
The insect pest repellent of the present invention can
contain (c) a hydrocarbon ester having a total of 8-16 carbon
atoms, as another repellent fragrance component, in addition
to the repellent fragrance components (a) and (b). The
repellent fragrance component (c) cooperates with the
repellent fragrance components (a) and (b) to contribute to
enhancement of the repellent effect on the specific invasive
alien ants.
[0037]
Examples of the repellent fragrance component (c)
include decyl acetate, linalyl acetate, geranyl acetate,
citronellyl acetate, menthyl acetate, terpinyl acetate, neryl
acetate, p-t-butylcyclohexyl acetate, tricyclodecenyl acetate,
tricyclodecenyl propionate, tricyclodecenyl isobutyrate,
benzyl acetate, phenylethyl acetate, styralyl acetate,
cinnamyl acetate, cinnamyl propionate, allyl hexanoate, allyl
heptanoate, methyl benzoate, ethyl benzoate, 3-hexenyl
benzoate, benzyl benzoate, methyl cinnamate, ethyl cinnamate,
methyl salicynate, ethyl salicynate, amyl salicynate, methyl
jasmonate, and methyl dihydrojasmonate. These repellent
fragrance components (c) may be used alone or in combination.
[00381
The insect pest repellent of the present invention can
optionally contain other components in addition to the
repellent fragrance components. Examples of such components include hydrocarbons such as d-limonene, a-pinene, and B pinene, hydrocarbon ethers such as isoamyl phenyl ethyl ether, linalool oxide, 1,8-cineol, rose oxide, diphenyl ether, magnolan, rhubafuran, and dihydroindenyl-2,4-dioxane, nitrogen-containing compounds such as 2,6-dimethyl-3 ethylpyrazine, citronellyl nitrile, stemone, and o aminoacetophenone, and essential oils such as sandalwood oil, spearmint oil, thyme white oil, patchouli oil, garlic oil, cinnamon leaf oil, thyme red oil, jasmine oil, neroli oil, bergamot oil, orange oil, geranium oil, petitgrain oil, lemon oil, lemongrass oil, cinnamon oil, eucalyptus oil, and lemon eucalyptus oil.
[00391
Furthermore, the insect pest repellent of the present
invention advantageously contains a glycol and/or a glycol
ether. The glycol and/or glycol ether serve not only as a
solvent for the repellent component or repellent fragrance
component, but also as a repellent effect-sustaining component
that sustains the repellent effect of the repellent component
or repellent fragrance component. This is because glycols
and/or glycol ethers have a higher vapor pressure than that of
the piperidine derivative. If a glycol and/or a glycol ether
are added to the piperidine derivative, the excessive
vaporization and diffusion of the piperidine derivative is
inhibited, so that the repellent effect of the piperidine
derivative on the specific invasive-alien ants can be sustained over a long period of time.
[00401
Examples of a glycol and/or a glycol ether that can be
used as the repellent effect-sustaining component include
propylene glycol (10.7 Pa), dipropylene glycol (1.3 Pa),
tripropylene glycol (0.67 Pa), diethylene glycol (3 Pa),
triethylene glycol (1 Pa), 1,3-butylene glycol, hexylene
glycol (6.7 Pa), benzyl glycol (2.7 Pa), diethylene glycol
monobutyl ether (3 Pa), dipropylene glycol monobutyl ether,
and tripropylene glycol monomethyl ether. The parenthesized
value following each substance name indicates a vapor pressure
at 200C. Of these glycols and/or glycol ethers, dipropylene
glycol is a preferable repellent effect-sustaining component.
The content of the repellent effect-sustaining component is
preferably 0.2-10 times as great as that of the repellent
component and repellent fragrance component.
[0041]
The insect pest repellent of the present invention may
additionally contain a functional component, such as a
deodorant component, antibacterial component, or antifungal
component, provided that the substance and the amount thereof
do not impair the repellent effect of insect pest repellent on
the specific invasive-alien ants. Representative examples of
the deodorant component include extracts of plants of the
families Poaceae, Theaceae, Ginkgoaceae, Oleaceae, Moraceae,
Rutaceae, Malpighiaceae, and Ebenaceae, etc. Also, leaf alcohol, leaf aldehyde, etc., which are called "green leaf volatiles," may be added to impart a relaxing effect.
[0042]
It is preferable that the insect pest repellent of the
present invention should be substantially free from
insecticidal components, because of its purpose. As used
herein, the term "substantially free from" with respect to an
insecticidal component(s) does not necessarily mean that the
content of the insecticidal component(s) is exactly zero
percent. For example, when a very small amount of an
insecticidal component is accidentally contained, or even when
a very small amount of an insecticidal component is
intentionally contained, then if the insecticidal component
does not provide an effective action, it is considered that
the insect pest repellent is substantially free from
insecticidal components. A very small amount of an
insecticidal component may be accidentally contained in the
following cases, for example: when production equipment for an
insect pest repellent has been used before in production of
another product containing an insecticidal component, a very
small amount of the insecticidal component adhering to a
container or pipe contaminates the insect pest repellent; and
an insecticidal component floating or vaporized and diffused
in the air in a production room is absorbed and contaminates
an insect pest repellent being produced. In such cases, the
insecticidal component is considered to be substantially free from insecticidal components, although the insect pest repellent actually contains a very small amount of an insecticidal component.
[0043]
The insect pest repellent of the present invention,
which is substantially free from insecticidal components, has
a high repellent effect on the specific invasive-alien ants
due to the piperidine derivative, which is an essential
component of the insect pest repellent of the present
invention, and therefore, exhibits a repellent effect similar
to or higher than that of a conventional repellent containing
an insecticidal component. In addition, consumers who are
hypersensitive to an insecticidal component will not hesitate
to use the insect pest repellent of the present invention,
which is substantially free from insecticides, in everyday
life. Furthermore, even when an insect pest becomes resistant
to a conventional repellent component such as DEET, the insect
pest repellent of the present invention will be expected to
have a repellent effect on such an insect pest.
[0044]
[Insect Pest Repellent Product]
The insect pest repellent of the present invention can
be directly used in applications for repelling the specific
invasive-alien ants without a special process. However, the
insect pest repellent of the present invention may be prepared
in a convenient form, and used as an insect pest repellent product containing 0.01-99 w/w% of the insect pest repellent, which is practical. Representative examples of the form of the insect pest repellent product include liquid formulation, gel formulation, and solid formulation.
[0045]
Examples of liquid and gel formulations include liquid,
emulsion, aqueous solution, microemulsion, aerosol, and cream.
For liquid and gel formulations, the contents of components
such as a repellent component, repellent fragrance component,
and repellent effect-sustaining component are easily adjusted.
Therefore, advantageously, characteristics of the insect pest
repellent product as a commercial product can be easily
modified, e.g., the repellent effect can be enhanced by
increasing the amount of the repellent component, the
fragrance is improved by increasing the amount of the
repellent fragrance component, etc.
[0046]
Examples of solid formulation include powder, grains,
and bait. Solid formulation does not have the risk of leakage
of liquid or wetting of fingers, and therefore, is
advantageously easily handled. The insect pest repellent
product made in the form of solid formulation can, for
example, be prepared by causing a suitable carrier to carry
the insect pest repellent or impregnating a suitable carrier
with the insect pest repellent. To cause a carrier to carry
the insect pest repellent, a solvent, surfactant, or the like may be optionally added. Examples of the carrier include plant powders, such as wood powder and wheat flour, paper, base cloth, such as woven fabric and nonwoven fabric, porous organic molded products, such as Viscopearl, inorganic carriers, such as kaolinite, talc, calcium carboxide, silica stone, silica sand, and ceramics, films or molded products made of polyethylene, polypropylene, an ethylene-vinyl acetate copolymer (EVA), an ethylene-methyl methacrylate copolymer
(EMMA), a styrene-based diblock polymer, a styrene-based
triblock polymer, a thermoplastic resin elastomer (TPE, TPO),
and the like, and silicone rubber. In the case where the
carrier is nonwoven fabric, for example, the carrier is caused
to retain the insect pest repellent using a chemical liquid
dispensing or applying method, or alternatively, the insect
pest repellent is embedded together with paraffin wax in the
carrier. In the case where the carrier is a film or molded
product, for example, the carrier is caused to retain the
insect pest repellent using a chemical liquid dispensing or
applying method, or alternatively, the insect pest repellent
is sprayed or dropped together with a solvent to permeate the
film or molded product. In the case where the carrier is
silicone rubber, for example, silicone rubber containing a
high concentration of the insect pest repellent and untreated
silicone rubber are put in a closed container, and are allowed
to stand for a predetermined period of time so that the
concentration of the insect pest repellent is averaged throughout the silicone rubber.
[00471
The added amount of the insect pest repellent in the
insect pest repellent product is suitably adjusted, depending
on the application, use period, specification, or the like of
the insect pest repellent product. The added amount of the
insect pest repellent in the insect pest repellent product is
preferably 0.01-20 w/v% for liquid or gel formulation, and is
preferably 0.01-10 w/w% for solid formulation. For example, in
the case where the insect pest repellent product is a solid
formulation employing a carrier, and is supposed to be used
for 8-12 hours, the content of the insect pest repellent is
preferably 10-50 mg per product. In the case where the insect
pest repellent product is supposed to be used for 15-30 days,
the content of the insect pest repellent is preferably 100
2000 mg per product.
[0048]
When the insect pest repellent product is prepared, a
solvent, surfactant, solubilizing agent, gel base, gelling
agent, dispersant, stabilizer, pH adjusting agent, coloring
agent, etc., can be optionally added. Examples of the solvent
include water, lower alcohols such as ethanol and isopropanol,
ketone solvents, ester solvents, and hydrocarbon solvents such
as normal paraffin and isoparaffin. Examples of the surfactant
include non-ionic surfactants such as polyoxyethylene
hydrogenated castor oil, polyoxyethylene higher alkyl ethers
(polyoxyethylene lauryl ether, polyoxyethylene oleyl ether,
etc.), polyoxyethylene alkyl phenyl ethers, polyoxyethylene
higher fatty acid esters, polyoxyethylene sorbitan fatty acid
esters, polyoxyethylene glycerin fatty acid esters, and
polyoxyethylene polyoxypropylene alkyl ethers, and higher
alkyl amine oxide surfactants such as lauryl amine oxide,
stearyl amine oxide, and lauric acid amidopropyl dimethylamine
oxide. Examples of the gelling agent include polyvinyl
alcohol, alginic acid, and carrageenan.
[0049]
The insect pest repellent product of the present
invention is used in various situations, depending on its
form. The insect pest repellent product prepared in the form
of liquid formulation is, for example, used as a spray product
and sprayed toward an object or in an environment. The insect
pest repellent product prepared in the form of gel formulation
is, for example, used as an application product and applied to
the human skin. The insect pest repellent product prepared in
the form of solid formulation is, for example, scattered or
placed in a predetermined amount at an entrance, in a kitchen,
bathroom, living room, bedroom, warehouse, car, or garden,
around a house, or the like. In particular, in the case where
the insect pest repellent product is a solid formulation, a
three-dimensional barrier that repels the specific invasive
alien ants is formed around the insect pest repellent product,
and therefore, the repellent effect can be spread over a wide range. In the case where the insect pest repellent product is a molded product or silicone rubber that carries the insect pest repellent, the insect pest repellent product can be wrapped as a band around an ankle, shoe, or the like, or can be attached to a shoe using a fixture such as a clip, in use.
In the case where the insect pest repellent product is a seal
or film that carries the insect pest repellent, then if the
insect pest repellent product is also provided with an
adhesive layer on the lower surface of the carrier, the insect
pest repellent product can be attached to a lower portion of
pants, a shoe, or the like in use.
[00501
The amount of the insect pest repellent product that is
applied (such an amount is referred to as a "dose") is
suitably adjusted, depending on its form. For liquid or gel
formulation, the dose is preferably 10-50 mL/m 2 . If the dose
is less than 10 mL/m 2 , a sufficient repellent effect cannot be
expected. If the dose is more than 50 mL/m 2 , unpleasant
feeling increases due to stickiness. For solid formulation,
the dose is preferably 10-50 g/m 2 . If the dose is less than 10
g/m2, a sufficient repellent effect cannot be expected. If the
dose is more than 50 g/m 2 , the repellent effect is not
substantially changed, and is ineffective in terms of cost.
Examples
[0051]
Next, examples of the insect pest repellent of the present invention, and examples of the insect pest repellent product employing the insect pest repellent of the present invention, will be described. Various examples of the insect pest repellent of the present invention were prepared and used to conduct an efficacy verification test on domestic ants and the specific invasive-alien ants (Examples 1-19). For comparison, a similar efficacy verification test was conducted on conventional insect pest repellents (Comparative Examples
1-5). Although in the examples below, the weight of each
component is expressed in units of mg, the weights in the
examples can be scaled up by any reasonable factor. Therefore,
the weight unit "mg" can be replaced by "parts by weight."
[0052]
[Preparation of Insect Pest Repellent]
The insect pest repellents of Examples 1-19 and
Comparative Examples 1-5 were prepared according to
compositions shown in Table 1.
[0053]
Table 1
Insect pest repellent (a numeral figure indicates the content of a component: mg)
Insect pest repellent (a)Repellent fragrance (b)Repellent compnentcompnentfragrance (a)/(b) Other components component component component piperidine a 1 50 piperidine b 2 50 piperidine c 3 50 piperidine d 4 50 piperidine a 5 35 6 piperidine a a-hexylcinnamic 35 aldehvde 10 7 piperidine a menthol 35 10 Theaceae-derived 8 piperidine a a-hexylcinnamic menthol 1/1 deodorantcomponent 35 aldehyde 5 5 1
9 piperidine a 20 10 piperidine a cis-jasmone 20 10 piperidine a citronellol M 20 10 x u 12 piperidine a cis-jasmone citronellol 1/1 20 5 5 13 piperidine a cis-jasmone citronellol 20 9 1 14 piperidine a cis-jasmone citronellol 0.1/1 20 1 9 piperidine a cis-jasmone citronellol allyl heptanoate 15 20 5 5 5 16 piperidine a cis-jasmone citronellol dipropylene glycol 20 5 5 10 allyl heptanoate piperidine a cis-jasmone citronellol 1/1 5 1 20 5 5 dipropylene glycol 10 citronellal linalool piperidine a 2 3 peppermint oil 18 20 perillaldehyde geraniol 3 5 2 decanal terpineol benzyl acetate 19 piperidine a 2 3 0.54 20 j3-damascone thymol lemon eucalyptus oil 1 3 2 1 piperidine e 50 2 piperidine f x2 50 DEET 50 a-hexylcinnamic 4 E aldehyde 50 5 menthol 50
[00541
Here, piperidines a-f in Table 1 that are an insect pest
repellent component are a piperidine derivative that is
represented by formula (I) and in which the substituent R is a
functional group shown in Table 2 below.
[0055]
Table 2
Piperidine derivative Substituent R Remarks 1-methyl propoxy group piperidine a (caridin) alkoxy group having 4 carbon atoms
piperidine b etoxy group alkoxy group having 2 carbon atoms piperidine c hexyloxy group alkoxy group having 6 carbon atoms piperidine d butylgroup alkyl group having 4 carbon atoms
piperidine e decyloxy group alkoxy group having 10 carbon atoms piperidine f octylgroup alkyl group having 8 carbon atoms
[0 0 56]
Note that the piperidine a (icaridin), piperidine b, and
piperidine d were a commercially available reagent grade
compound. The piperidine c, piperidine e, and piperidine f
were synthesized by the present inventors using a procedure
described below.
[0057]
[Piperidine c]
2-(2-hydroxyethyl)-piperidine (715 mg, 5.53 mmol) and
triethylamine (1.0 ml, 7.21 mmol) were dissolved in 6 ml of
toluene, and hexyl chloroformate (910 mg, 5.53 mmol) was added
at 0°C. Next, after stirring at 200C for 24 hours, water was added to the reaction liquid, and an organic component was extracted using ethyl acetate. Next, an organic layer containing the organic component was dried using magnesium sulfate, and thereafter, was concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatography to obtain the piperidine c. The mass spectrum of the piperidine c is as follows: colorless liquid: MS(EI)m/z[M] +: 257
[00581
[Piperidine e]
The piperidine e was obtained using a procedure that is
similar to that for synthesis of the piperidine c, except that
decyl chloroformate was used instead of hexyl chloroformate.
The mass spectrum of the piperidine e is as follows:
colorless liquid: MS(EI)m/z[M] +: 313
[00591
[Piperidine f]
The piperidine f was obtained using a procedure that is
similar to that for synthesis of the piperidine c, except that
n-nonanoyl chloride was used instead of hexyl chloroformate.
The mass spectrum of the piperidine f is as follows:
colorless liquid: MS(EI)m/z[M] +: 269
[00601
[Efficacy Verification Test 1]
The insect pest repellents of Examples 1-19 and
Comparative Examples 1-5 were each dissolved in 5 mL of acetone to prepare a chemical liquid of the insect pest repellent. Each resultant liquid specimen (0.3 mL) was dropped onto a half side of a filter sheet having a diameter of 15 cm using an atomizer, followed by air drying. In this case, for the filter sheet after drying, for example, in Example 1, 3.0 mg of the insect pest repellent is contained in the half side of the filter sheet. Next, the half side (processed section) of the filter sheet containing the insect pest repellent, and the half side (non-processed section) of the filter sheet not containing the insect pest repellent, were placed in a glass petri dish having a diameter of 15 cm without overlapping of these half sides. Thereafter, the internal wall of the glass petri dish was coated with talc, 30 Lasius japonicus ants (a type of domestic ants) or 30 tropical fire ants (one of the specific invasive-alien ants) were released, and the numbers of ants (the number of insects) present in the processed and non-processed sections were counted 5 minutes later and 2 hours later. The repellent rate of insect pests was calculated as follows: repellent rate (%) = (the number of insects in the non processed section - the number of insects in the processed section)/the number of test insects x 100
[0061]
The above efficacy verification test 1 was conducted
three times, and the average of the numbers of insects counted
in the three tests was used in calculation of the repellent rate. The test results are shown in Table 3 below.
[0 062]1
Table 3
Repellent rate(% Lasiusja ponicus ants Tropical fire ants 5 minuteslater 2 hours later 5 minutes later 2 hourslater 1 97 95 100 100 2 81 76 78 73 3 79 73 77 71 4 72 66 69 64 5 88 86 90 87 6 94 90 97 92 7 93 89 95 90 8 98 93 100 100 u~ 9 71 68 75 70 0 E 10 79 74 82 77 x LU 1 80 76 80 76 12 85 82 87 83 13 78 75 81 76 14 77 73 80 75 15 89 84 92 86 16 86 84 89 86 17 90 89 93 92 18 81 76 83 80 19 80 75 81 77 1 64 58 36 31 S2 61 55 42 33 ~E 3 57 50 43 39 E x 0 4 49 44 45 40 5 43 38 41 35
[00 63]
According to the result of the above efficacy verification test 1, the insect pest repellents containing a piperidine derivative represented by formula (I) had a repellent effect of repelling tropical fire ants, which are one of the specific invasive-alien ants, immediately after the start of the test (5 minutes later). The high repellent effect was substantially maintained even after 2 hours had elapsed
(Examples 1-19). Note that an effect similar to that on
tropical fire ants was verified for Lasius japonicus ants,
which are a type of domestic ants (Examples 1-19). In
particular, compounds that are a piperidine derivative
represented by formula (I) in which the substituent R is an
alkoxy group having 2-6 carbon atoms had an excellent
repellent effect. The compound (icaridin) in which the
substituent R is a 1-methyl propoxy group had a more excellent
repellent effect.
[0064]
More specifically, as can be seen from the results of
Examples 5-8 and Examples 9-19, it was verified that an insect
pest repellent containing, in addition to an insect pest
repellent component, at least one of (a) a hydrocarbon
aldehyde and/or hydrocarbon ketone having a total of 8-16
carbon atoms or (b) a monoterpene alcohol and/or aromatic
alcohol having a total of 8-12 carbon atoms, as a repellent
fragrance component, had a higher repellent effect
(synergistic effect) than that of an insect pest repellent
containing only an insect pest repellent component. In addition, according to this example, it was verified that a high repellent effect is achieved in the case where the blend ratio [(a)/(b)] of the repellent fragrance components (a) and
(b) is in the range of 0.1/1 to 9/1. Furthermore, the
comparison between Examples 12 and 16, and the comparison
between Examples 15 and 17, show that in the case where
dipropylene glycol is added, the effect of sustaining the
repellent effect of an insect pest repellent component is
achieved.
[00651
Meanwhile, as can be seen from the results of
Comparative Examples 1-5, the conventional insect pest
repellents containing a compound other than the piperidine
derivatives represented by formula (I), or DEET, which is a
repellent for the human body, cannot be said to have a
sufficient repellent effect on ants, and tend to have a much
less repellent effect on tropical fire ants compared to the
repellent effect on Lasius japonicus ants.
[00661
[Efficacy Verification Test 2]
The insect pest repellents of Examples 1, 5-14, and 18
and Comparative Examples 1-5 were each dissolved in 5 mL of
acetone to prepare a chemical liquid of the insect pest
repellent. These insect pest repellents were used to conduct
an efficacy verification test 2 on red imported fire ants (one
of the specific invasive-alien ants) using a procedure similar to that of the efficacy verification test 1. Note that the numbers of ants (the numbers of insects) present in the processed and non-processed sections were counted 5 minutes later only. The insect pest repellent rate was calculated using a method similar to that of the efficacy verification test 1. The test results are shown in Table 4.
[0067]
Table 4
Repellent rate(%) Red imported fire ants 5 minutes later 1 94 5 90 6 96 7 92 8 97 9 75 E x 10 80 11 77 12 83 13 81 14 80 18 85 1 39 2 35
E 3 50 E x O 4 38
5 62
[0068]
According to the test results of the efficacy verification test 2, the insect pest repellent containing the piperidine derivative (icaridin) represented by formula (I) in which the substituent R is particularly a 1-methyl propoxy group had an excellent repellent effect on red imported fire ants, which are one of the specific invasive-alien ants, immediately after the start of the test (5 minutes later).
[00691
Furthermore, as can be seen from the results of Examples
5-8, it was verified that an insect pest repellent containing,
in addition to an insect pest repellent component, at least
one of (a) a hydrocarbon aldehyde and/or hydrocarbon ketone
having a total of 8-16 carbon atoms or (b) a monoterpene
alcohol and/or aromatic alcohol having a total of 8-12 carbon
atoms, as a repellent fragrance component, had a higher
repellent effect (synergistic effect) than that of an insect
pest repellent containing only an insect pest repellent
component. In addition, the comparison between Examples 5 and
6, and the comparison between Examples 7 and 8, show that an
insect pest repellent containing a-hexylcinnamic aldehyde as a
repellent fragrance component has a much improved repellent
effect compared to an insect pest repellent not containing a
hexylcinnamic aldehyde.
[0070]
Meanwhile, as can be seen from the results of
Comparative Examples 1-5, the conventional insect pest
repellents containing a compound other than the piperidine derivatives represented by formula (I), or DEET, which is a repellent for the human body, had a less repellent effect on red imported fire ants as well.
[0071]
Thus, the insect pest repellent of the present invention
containing a piperidine derivative represented by formula (I)
had a similar or higher repellent effect on the specific
invasive-alien ants to or than that on domestic ants, which
performance cannot be achieved by conventional ant repellents,
i.e., remarkable performance. This demonstrates that the
insect pest repellent of the present invention is highly
useful and practical.
[0072]
[Example Configurations of Insect Pest Repellent
Products]
Next, example configurations of insect pest repellent
products employing the insect pest repellent of the present
invention will be described.
[0073]
[Spray Product (Liquid Formulation)]
An insect pest repellent was prepared that contained:
8.0 g (4.0 w/v%) of icaridin, which is represented by formula
(II), as an insect pest repellent component; 1.0 g (0.5 w/v%)
of cuminaldehyde and 2-pentylcyclopentanone as the repellent
fragrance component (a); and 2.0 g (1.0 w/v%) of 1-menthol and
2-phenylethyl alcohol, 0.2 g (0.1 w/v%) of isopropylmethyl phenol, and 1.0 g (0.5 w/v%) of a persimmon extract-derived deodorant component as the repellent fragrance component (b).
To this insect pest repellent, 110 g (55 w/v%) of 99% ethanol,
and purified water, were added to obtain a total amount of 200
mL of a mixture, and the resultant mixture was put into a pump
spray container to configure a spray type insect pest
repellent product (product A).
[0074]
The product A was sprayed throughout the outerwear and
pants of a subject (to the extent that their surfaces were
moist, about 20 mL/m 2 ), particularly intensively cuffs and
lower portions of the trousers, before the subject went to the
seaside (area where red imported fire ants had been reportedly
found). The subject, wearing the clothes, walked around in the
seaside for about 5 hours. The subject was not annoyed by the
specific invasive-alien ants such as red imported fire ants or
by domestic ants and other insect pests, and no ticks attached
to the subject.
[0075]
[Application Product (Gel Formulation)]
An insect pest repellent was prepared that contained:
3.0 g (5.0 w/w%) of icaridin, represented by formula (II), as
an insect pest repellent component; 3.0 g (5.0 w/w%) of 1,3
butylene glycol as a repellent effect-sustaining component;
and 0.12 g (0.2 w/w%) of ethylhexyl-para-methoxycinnamate as a
UV degradation inhibitory component. To this insect pest repellent, 0.09 g (0.15 w/w%) of a carboxyvinyl polymer as a gel base, 0.09 g (0.15 w/w%) of triethanolamine as a gelling agent, 21 g (35 w/w%) of ethanol, and purified water were added to obtain a total amount of 60 g of a mixture, and the resultant mixture was put into a gel dispensing container to configure a fragrance-free gel type insect pest repellent product (product B).
[0076]
A gel type insect pest repellent product (product C) was
prepared that contained, in addition to the insect pest
repellent used in the product B, 0.6 g (1.0 w/w%) of
dihydrojasmone as the repellent fragrance component (a) and
0.6 g (1.0 w/w%) of 1-phenylethyl alcohol and dihydromyrcenol
as the repellent fragrance component (b), and further
contained other components similar to those contained in the
insect pest repellent used in the product B. Thus, the gel
type insect pest repellent product (product C) was scented by
repellent fragrance.
[0077]
Two sticks having a diameter of about 4 cm and a length
of 1 m were prepared. An upper half (portion above about the
middle (50 cm)) of one of the two sticks was coated with the
product B in an application amount of 20 g/m 2 . The other stick
was similarly coated with the product C in the same
application amount. Each stick was pushed into a nest which
red imported fire ants frequently went in and out, and the behavior of red imported fire ants was observed. For both of the sticks, it was observed that red imported fire ants climbed up to near the middle of the stick and then retreated and climbed down. Such a behavior (heading back to the nest) of red imported fire ants was quicker in the case of the product C than the product B. Thus, it was demonstrated that icaridin has a high repellent effect on the specific invasive alien ants such as red imported fire ants, and when used in conjunction with the repellent fragrance components (a) and
(b), the repellent effect on the specific invasive-alien ants
is enhanced (synergistic effect).
INDUSTRIAL APPLICABILITY
[0078]
The insect pest repellent and insect pest repellent
product of the present invention are particularly useful for
repelling and controlling the specific invasive-alien ants,
and can be used not only as a home-use repellent product but
also as a professional-use repellent product.
[0079]
The term "comprise" and variants of the term such as
"comprises" or "comprising" are used herein to denote the
inclusion of a stated integer or stated integers but not to
exclude any other integer or any other integers, unless in the
context or usage an exclusive interpretation of the term is
required.
[00801
Any reference to any prior art in this specification is
not, and should not be taken as an acknowledgement or any form
of suggestion that the prior art forms part of the common
general knowledge.
[0081]
In a first aspect of the invention, there is provided an
insect pest repellent when used to repel fire ants comprising,
as a repellent component for fire ants, a piperidine
derivative represented by formula (I):
[Chemical Formula 1]
N CH2CH2OH (I)
CO-R
R:alkyl group or alkoxy group having 2-6 carbon atoms.
In a second aspect of the invention, there is provided
an insect pest repellent product when used to repel fire ants,
comprising:
the insect pest repellent of the first aspect,
wherein
the insect pest repellent product is in the form of
liquid formulation, gel formulation, or solid formulation.
In a third aspect of the invention, there is provided a
method of repelling fire ants comprising the step of applying
an insect pest repellent comprising a piperidine derivative
represented by formula (I):
[Chemical Formula 1]
N CH2CH2OH (I) CO-R R:alkyl group or alkoxy group having 2-6 carbon atoms.

Claims (18)

1. An insect pest repellent when used to repel fire
ants comprising, as a repellent component for fire ants, a
piperidine derivative represented by formula (I):
[Chemical Formula 1]
N CH2CH2OH (I)
CO-R R:alkyl group or alkoxy group having 2-6 carbon atoms.
2. The insect pest repellent of claim 1, wherein
in formula (I), R is an alkoxy group having 2-6 carbon
atoms.
3. The insect pest repellent of claim 2, wherein
R is a 1-methyl propoxy group.
4. The insect pest repellent of any one of claims 1
3, further comprising, as a repellent fragrance component, at
least one of:
(a) a hydrocarbon aldehyde and/or hydrocarbon ketone
having a total of 8-16 carbon atoms; or
(b) a monoterpene alcohol and/or aromatic alcohol having
a total of 8-12 carbon atoms.
5. The insect pest repellent of claim 4, wherein
the repellent fragrance component (a) is at least one
selected from the group consisting of decanal, undecanal,
dodecanal, 2-methyl undecanal, tridecanal, 10-undecenal,
citronellal, citral, neral, phenylacetaldehyde, cinnamic
aldehyde, a-amylcinnamic aldehyde, a-hexylcinnamic aldehyde,
lilial, perillaldehyde, trivertal, cuminaldehyde, heliotropin,
tridecanone, 1-carvone, menthone, pulegone, cis-jasmone,
dihydrojasmone, a-damascone, B-damascone, 5-damascone, a
ionone, B-ionone, 2-pentylcyclopentanone, 2
hexylcyclopentanone, 2-heptylcyclopentanone, methyl benzyl
ketone, and methyl styryl ketone, and
the repellent fragrance component (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-phenylethylalcohol, 2-phenylethylalcohol, cinnamic
alcohol, thymol, and eugenol.
6. The insect pest repellent of claim 4 or 5,
wherein
the blend ratio (weight ratio) (a)/(b) of the repellent
fragrance components (a) and (b) is 0.1/1 to 9/1.
7. The insect pest repellent of any one of claims 1
6, further comprising, as a repellent effect-sustaining
component, a glycol and/or a glycol ether.
8. The insect pest repellent of any one of claims 1
7, wherein
the insect pest repellent is substantially free from
insecticidal components.
9. An insect pest repellent product when used to
repel fire ants, comprising:
the insect pest repellent of any one of claims 1-8,
wherein
the insect pest repellent product is in the form of a
liquid formulation, gel formulation, or solid formulation.
10. A method of repelling fire ants comprising the
step of applying an insect pest repellent comprising a
piperidine derivative represented by formula (I):
[Chemical Formula 1]
N CH2CH2OH (I)
CO-R
R:alkyl group or alkoxy group having 2-6 carbon atoms.
11. The method of claim 10, wherein
in formula (I), R is an alkoxy group having 2-6 carbon atoms.
12. The method of claim 11, wherein
R is a 1-methyl propoxy group.
13. The method of any one of claims 10-12, further
comprising, as a repellent fragrance component, at least one
of:
(a) a hydrocarbon aldehyde and/or hydrocarbon ketone
having a total of 8-16 carbon atoms; or
(b) a monoterpene alcohol and/or aromatic alcohol having
a total of 8-12 carbon atoms.
14. The method of claim 13, wherein
the repellent fragrance component (a) is at least one
selected from the group consisting of decanal, undecanal,
dodecanal, 2-methyl undecanal, tridecanal, 10-undecenal,
citronellal, citral, neral, phenylacetaldehyde, cinnamic
aldehyde, a-amylcinnamic aldehyde, a-hexylcinnamic aldehyde,
lilial, perillaldehyde, trivertal, cuminaldehyde, heliotropin,
tridecanone, 1-carvone, menthone, pulegone, cis-jasmone,
dihydrojasmone, a-damascone, B-damascone, 5-damascone, a
ionone, B-ionone, 2-pentylcyclopentanone, 2
hexylcyclopentanone, 2-heptylcyclopentanone, methyl benzyl
ketone, and methyl styryl ketone, and
the repellent fragrance component (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-phenylethylalcohol, 2-phenylethylalcohol, cinnamic alcohol, thymol, and eugenol.
15. The method of claim 13 or 14, wherein
the blend ratio (weight ratio) (a) / (b) of the repellent
fragrance components (a) and (b) is 0.1/1 to 9/1.
16. The method of any one of claims 10-15, further
comprising, as a repellent effect-sustaining component, a
glycol and/or a glycol ether.
17. The method of any one of claims 10-16, wherein
the insect pest repellent is substantially free from
insecticidal components.
18. The method of any one of claims 10-17, wherein
the insect pest repellent is in the form of a liquid
formulation, gel formulation, or solid formulation.
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TW201946533A (en) 2019-12-16

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