JP5404188B2 - Pest repellent - Google Patents

Description

  The present invention relates to a pest repellent. More specifically, the present invention relates to a repellent that is safe for the human body and effective against pests, particularly cockroaches, comprising an alcohol or ether compound having a specific structure as an active ingredient.

  Conventionally, glycol ethers having an ethylene glycol structure and a propylene glycol structure (Patent Documents 1 to 3) are known as repellents for cockroaches and animals.

JP 61-289002 JP 61-194001 JP 61-267501 A

  The present invention has been completed by finding that glycol ether compounds having different structures not in the ethylene glycol structure and propylene glycol structure have extremely excellent repellent activity against insects such as cockroaches. An object of the present invention is to provide a repellent that is safe against the human body and effective against pests, particularly cockroaches.

  Under the circumstances as described above, as a result of intensive studies, the present inventors may indicate an alcohol or ether compound (hereinafter simply referred to as compound (1)) represented by the following general formula (1). However, it was found that there is little odor, it is safe for the human body, and it has a high repellent effect against pests.

Accordingly, the present invention provides the following sections:
Item 1. 3-methoxy-3-methyl-1-butanol, 3-methoxy-1-butanol, 1-methoxy-2-butanol, isostearyl glyceryl ether, POE oleyl ether (n = 2 or n = 5); POE lauryl ether ( n = 2 or n = 4); POE (1) POP (4) cetyl ether; insect pests against cockroaches containing at least one selected from the group consisting of 1-butanol and 4-phenyl-1-butanol as an active ingredient Repellent.

Item 2 . A cockroach repellent method for repelling cockroaches using the insect repellent according to Item 1 .

  The compound (1) used in the present invention exhibits an extremely excellent repellent activity against pests such as cockroaches. In addition, the compound (1) is safe with little odor and little influence on the human body.

  Specifically, each group shown in the general formula is as follows.

  When Y is an optionally substituted alkylene group having 4 to 8 carbon atoms, examples of the alkylene group having 4 to 8 carbon atoms include linear alkylene groups having 4 to 8 carbon atoms. . Specific examples include tetramethylene, pentamethylene, hexamethylenetetramethylene, pentamethylene, hexamethylene, heptamethylene and octamethylene groups.

  Examples of the substituent when Y is an optionally substituted alkylene group having 4 to 8 carbon atoms include a hydroxyl group, an alkyl group, an alkoxy group, and a phenyl group.

  When the substituent is an alkyl group, examples of the alkyl group include linear or branched alkyl groups having 1 to 4 carbon atoms (preferably 1). Specific examples include methyl, ethyl, n-propyl, n-butyl, isopropyl, and isobutyl groups.

  When the substituent is an alkoxy group, examples of the alkoxy group include linear or branched alkoxy groups having 1 to 4 carbon atoms (preferably 1). Specific examples include methoxy, ethoxy, n-propoxy, n-butoxy, isopropoxy, isobutoxy group and the like.

  When the alkylene group having 4 to 8 carbon atoms has a substituent, examples of the number of substituents include 1 to 3, preferably 1 to 2. When the alkylene group having 4 to 8 carbon atoms has two or more substituents, these substituents may be the same or different.

In the case where Y is an optionally substituted alkylene group having 4 to 8 carbon atoms and at least one of R ¹ and R ² is an alkoxy group, the alkoxy group may have 1 to 4 carbon atoms (preferably Can be exemplified by the linear or branched alkoxy group of 1). Specific examples include methoxy, ethoxy, n-propoxy, n-butoxy, isopropoxy, isobutoxy group and the like.

When Y is an optionally substituted alkylene group having 4 to 8 carbon atoms and at least one of R ¹ and R ² is an alkenyloxy group, the alkenyloxy group has 1 double bond. Examples thereof include a linear or branched alkenyloxy group having 2 to 3 carbon atoms having 2 to 3 carbon atoms (preferably 2 to 3 carbon atoms). Specific examples include vinyloxy, 2-propenyloxy, 3-butenyloxy groups and the like.

Y is _{- (CH 2 CH 2 CH 2} O) m1 - (CH 2 CH 2 O) m2 -CH 2 CH 2 - if it is, m1 is an integer of 0 or more, preferably 0-3, more preferably 0 or 1 is shown.
m2 represents an integer of 0 or more, preferably 0 to 5, and more preferably 1 to 4.
However, m1 + m2 represents 1 or more.

In the present invention, Y is — (CH ₂ CH ₂ CH ₂ O) _m1 — (CH ₂ CH ₂ O) _m2 —CH ₂ CH ₂ —, m1 is 0, and at least one of R ¹ and R ² When is an alkoxy group, the alkoxy group represents an n-lauryloxy group.

When m1 is 0 and at least one of R ¹ and R ² is an alkenyloxy group, the alkenyloxy group represents an n-oleyloxy group.

When m is 1 or more and at least one of R ¹ and R ² is an alkoxy group, the alkoxy group is a straight chain having 12 to 20 carbon atoms, preferably 14 to 18 carbon atoms, more preferably 16 carbon atoms. Or a branched alkoxy group can be illustrated. More specifically, examples include lauryloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, cetyloxy, heptadecyloxy, stearyloxy, nonadecyloxy, eicosyloxy, and isostearyloxy groups.

When m is 1 or more and at least one of R ¹ and R ² is an alkenyloxy group, the alkenyloxy group is a group having 12 to 20 carbon atoms, preferably 14 to 14 carbon atoms having 1 to 3 double bonds. A linear or branched alkenyloxy group having 18 carbon atoms, more preferably 16 carbon atoms, can be exemplified. More specifically, for example, 11-dodecenyloxy, 12-tridecenyloxy, 13-tetradecenyloxy, 14-pentadecenyloxy, 15-hexadecenyloxy, 16-heptadecenyloxy, Examples include oleyloxy, 18-nonadecenyloxy, 19-eicocenyloxy group and the like.

When Y is —CH ₂ CH (OR ³ ) CH ₂ — and R ³ is an alkyl group, the alkyl group has 16 to 20 carbon atoms, preferably 17 to 19 carbon atoms, more preferably carbon. The linear or branched alkyl group of Formula 18 can be exemplified. More specifically, for example, cetyl, heptadecyl, stearyl, nonadecyl, eicosyl, isostearyl group and the like can be mentioned.

When Y is —CH ₂ CH (OR ³ ) CH ₂ — and at least one of R ¹ and R ² is an alkoxy group, the alkoxy group has 16 to 20 carbon atoms, preferably 17 to 19 carbon atoms. More preferably, a linear or branched alkoxy group having 18 carbon atoms can be exemplified. More specifically, for example, cetyloxy, heptadecyloxy, stearyloxy, nonadecyloxy, eicosyloxy, isostearyloxy groups and the like can be mentioned.

When Y is —CH ₂ CH (OR ³ ) CH ₂ — and at least one of R ¹ and R ² is an alkenyloxy group, the alkenyloxy group has 1 to 3 carbon atoms having double bonds. Examples thereof include a linear or branched alkyl group having 16 to 20, preferably 17 to 19 carbon atoms, more preferably 18 carbon atoms. More specifically, for example, 15-hexadecenyloxy, 16-heptadecenyloxy, oleyloxy, 18-nonadecenyloxy, 19-eicocenyloxy group and the like can be mentioned.

In a preferred embodiment of the invention Y is of the formula —CHR ⁴ —CR ⁵ R ⁶ —CH ₂ —CH ₂ —.
[Wherein, R ⁴ represents hydrogen, an alkyl group having 1 to 4 carbon atoms, or a phenyl group.
R ⁵ represents hydrogen, a halogen atom, or an alkyl group having 1 to 4 carbon atoms.
R ⁶ represents hydrogen, an alkoxy group having 1 to 4 carbon atoms, or a hydroxyl group.
When R ⁴ is an alkyl group having 1 to ⁴ carbon atoms or a phenyl group, R ⁵ and R ⁶ both represent a hydrogen atom. ]
An alkylene group having 4 to 8 carbon atoms which may have a substituent represented by:
When R ⁶ is hydrogen or an alkoxy group having 1 to 4 carbon atoms, R ¹ represents a hydrogen atom and R ² represents a hydroxyl group;
When R ⁶ is a hydroxyl group, R ¹ represents an alkoxy group and R ² represents a hydrogen atom.

In another preferred embodiment of the invention, Y is of the formula — (CH ₂ CH ₂ CH ₂ O) _m1 — (CH ₂ CH ₂ O) _{m 2} —CH ₂ CH ₂ —.
[Wherein m1 represents 0 or 1;
When m1 is 0, m2 represents an integer of 1 to 4, and when m1 is 1, m2 represents 3. ]
A group represented by
when m1 is 0, R ¹ represents an oleyloxy group or a lauryloxy group and R ² represents a hydroxyl group;
When m1 is 1, one of R ¹ and R ² represents a cetyloxy group and the other represents a hydroxyl group.

In yet another preferred embodiment of the invention, Y is of the formula —CH ₂ CH (OR ³ ) CH ₂ —.
[Wherein R ³ represents a hydrogen atom or an isostearyl group. ]
A group represented by
When R ³ is a hydrogen atom, R ¹ represents an isostearyloxy group and R ² represents a hydroxyl group;
When R ³ is an isostearyl group, R ¹ and R ² both represent a hydroxyl group.

  Specific examples of the compound (1) include 2-methoxy-1-butanol, 3-methoxy-1-butanol, 4-methoxy-1-butanol, 1-methoxy-2-butanol, and 3-methoxy-2-butanol. Alkoxybutanol such as 4-methoxy-2-butanol; 2-methoxy-2-methyl-1-butanol, 3-methoxy-2-methyl-1-butanol, 4-methoxy-2-methyl-1-butanol, 2 -Alkoxyalkylbutanol such as methoxy-3-methyl-1-butanol, 3-methoxy-3-methyl-1-butanol, 4-methoxy-3-methyl-1-butanol; isostearyl glyceryl ether; POE oleyl ether (n = 2 or n = 5); POE lauryl ether (n = 2 or n = 4); POE (1) POP 4) cetyl ether; 1-butanol, alcohols such as 1-octanol; include a phenyl butanol of 4-phenyl-1-butanol and the like.

  In the present invention, compound (1) naturally includes isomers such as optical isomers, geometric isomers and stereoisomers.

  The present invention also includes a pest repellent containing the compound (1) in a derivatized state by a method usually used in the technical field of the present invention, or a derivative and a compound thereof, as long as the effects of the present invention are not lost. What contains the mixture with (1) etc. may be included.

  The pest repellent of the present invention is a house entrance, a kitchen, a canteen, a barn, a specific area such as an agricultural and horticultural house, a chest, a food storage, a clothes case, a storage case such as a doll case, and a human body, By applying to animals and plants, pests can be prevented from flying, approaching, touching and entering these places, and pests, food damage, etc. Bite, blood sucking, and even contamination can be avoided brilliantly.

  In the present invention, the pests are sanitary pests such as cockroaches, flies, ticks, fleas, bedbugs, nukaka, mosquitoes, chironomids, etc. Refers to unpleasant pests such as ants, termites, bees, gejigeji, centipedes and the like.

  In the present invention, the pest repellent effect (action) means that it has one or more of the above-mentioned pest fixing inhibitory action, invasion preventive action and landing preventive action.

  The compound (1) which is an active ingredient of the present invention has a very strong pest repellent activity. The compound (1) does not necessarily need to be a single compound as an active ingredient when used, and can be used as a mixture with other pest repellent ingredients as described above.

  The pest repellent of the present invention can be applied as it is to the area where pest repellent is required as it is, but it is usually preferable to use an appropriate carrier or other compounding agent in an appropriate area, an appropriate method, etc. It is prepared and used in various suitable forms such as liquids and solids. Carriers used in preparing the liquid form include, for example, water, alcohols such as methyl alcohol and ethyl alcohol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, hexane, kerosene, paraffin, petroleum Examples thereof include aliphatic hydrocarbons such as benzine, aromatic hydrocarbons such as benzene and toluene, esters such as ethyl acetate, and halogenated hydrocarbons such as dichloroethane. These liquid pest repellents of the present invention can further contain additives such as ordinary film-forming agents, emulsifiers, dispersants, spreading agents, wetting agents, stabilizers, propellants, etc. It can be used in the form of forms, adhesive forms, emulsions, dispersants, turbidity agents, lotions, creams, sprays, aerosols and the like. Examples of these additives include cellulose derivatives such as nitrocellulose, acetylcellulose, acetylbutyrylcellulose, and methylcellulose, vinyl resins such as vinyl acetate resins, alkyd resins, urea resins, epoxy resins, and polyester resins. , Urethane resins, silicone resins, acrylic resins, chlorinated rubber, coating agents such as polyvinyl alcohol, soaps, polyoxyethylene aliphatic alcohol ethers such as polyoxyethylene oleyl ether, polyoxyethylene nonylphenyl ether, etc. Such as polyoxyethylene alkyl aryl ethers, polyoxyethylene fatty acid esters, fatty acid glycerides, sorbitan fatty acid esters, sulfates of higher alcohols, and dodecylbenzene sulfonic acid soda Surface active agents such Rusuruhon acid salts, liquefied petroleum gas, dimethyl ether, a propellant such as a fluorocarbon, casein, gelatin, alginic acid, and carboxymethyl cellulose (CMC) can be exemplified.

  Examples of the carrier used for preparing the solid form include mineral powders such as silicic acid, kaolin, activated carbon, bentonite, diatomaceous earth, talc, clay, calcium carbonate, ceramic powder, wood powder, and soybean powder. And vegetable powders such as wheat flour and starch, and inclusion compounds such as cyclodextrin. Further, in preparing in the form of the solid agent, for example, a sublimable carrier such as tricyclodecane, cyclododecane, 2,4,6-triisopropyl-1,3,5-trioxane, trimethylene norbornene, paradichlorobenzene, A sublimable insect repellent such as naphthalene or camphor can be used, and the above active ingredient compound can be melt mixed or crushed and then molded into a sublimable solid agent.

  The pest repellent of the present invention is, for example, a microencapsulated form according to a spray drying method using polyvinyl alcohol or CMC, a liquid curing method using gelatin, polyvinyl alcohol, alginic acid or the like, a coacervation method, etc. Or a gel form using a gelling agent such as benzylidene-D-sorbitol or carrageenan.

Furthermore, the pest repellents of the present invention include known pest repellents, efficacy enhancers, antioxidants, insecticides, rodent control agents, and repellents, fungicides, fungicides, herbicides, fertilizers , Flavoring agents, coloring agents and the like can be blended. Other pest repellents that can be incorporated include N, N-diethyl-meta-toluamide, 2,3,4,5-bis (A ₂ -butylene) -tetrahydrofurfural, di-n-propylisocincomellonate, Di-n-butyl succinate, 2-hydroxyethyl octyl sulfide, etc., and N- (2-ethylhexyl) -bicyclo- [2,2,1] -5-heptene-2,3-dicarboxy as an efficacy enhancer Imido, 6- (propylpiperonyl) -butylcarbinyl ether, etc., as antioxidants, butylhydroxyanisole, dibutylhydroxytoluene, tocopherol, γ-oryzanol, etc., as insecticides, general names arelin and its geometry And / or pyrethroids such as optical isomers as rodent control and repellents such as α-naphthylthiourea, cycloheximi , Salicylic acid, p-chloro-m-xylenol, 2- (4′-thiazoyl) benzimidazole and the like as insecticides, and α-bromocinnamic aldehyde, N-dimethyl-N − as antifungal agents. Examples thereof include phenyl-N ′-(fluorodichloromethyl) thiosulfamide.

  The pest repellent of the present invention having various forms thus prepared is a pest intrusion area that is required to have a repellent effect in its use, such as crop cultivation fields, orchards, general households, grain warehouses, cafeteria kitchens, furniture It can be applied by placing, spreading, spraying, applying, pasting, etc. on closets, entrances, toilets, etc., and by spreading, spraying, applying, etc. on animals and plants themselves.

The amount of the compound (1) in the pest repellent of the present invention and the amount of the repellent used may be appropriately determined according to the dosage form, application method, application place, etc. When used in the form of a liquid agent such as a powder or wettable powder, the compound (1) may be contained in an amount of 1 to 80% by weight, preferably 5 to 40% by weight. -50% by weight, preferably 2-20% by weight, and, for example, in the case of application, the amount of compound (1) is about 0.0005 mg or more per 1 cm ^{2 of} area to be applied. When used in a solid or other form, it is appropriate that about 0.5 mg or more of compound (1) is present per 1 m ^{3 of} application space.

  The present invention also provides a pest repellent obtained by holding the above pest repellent on a substrate. The pest repellent is also used as a sheet-like base material or furniture member having pest repellent properties by utilizing the characteristics of the base material. Here, as the base material, for example, synthetic resin sheets such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, and polyester, animal and vegetable or inorganic fiber sheets (paper, cloth, nonwoven fabric, leather, etc.), and synthesis of these Examples include synthetic sheets or mixed fabrics of resin and inorganic fibers or powders, mixed fabrics or non-woven fabrics of the above synthetic resins and animal and vegetable fibers, metal foils or films such as aluminum, stainless steel, and zinc, and laminated sheets of the above various sheets. . In addition, as the base material, natural wood using this as a furniture member such as drill, pencil fern, cox, etc., and plastics such as vinyl chloride resin, chlorinated polyethylene, polyethylene, polypropylene, etc. are also effectively used. it can.

  The means for holding the pest repellent of the present invention on these base materials is not particularly limited, and for example, it is held by application, impregnation, dripping, kneading, etc., and mounted on the target location in the form held on the base material. It can be used by placing or pasting. The amount to be retained is not particularly limited and can be determined as appropriate.

The pest repellent activity of the compound (1) will be described in detail based on examples and test examples.

Test Example 1 Fixation inhibition efficacy test against German cockroaches Various compounds were used to evaluate the repellent efficacy against German cockroaches.

[Sample]
The compounds used are as follows:

[Test method]
Transparent resin shelter (12 x 12 x 1 cm) diagonally on four corners of a 50 cm x 50 cm square bat (bat height, 25 cm) containing 30 German cockroaches (♂ / ♂ = 15/15) ) Was installed. One of the two shelters on the diagonal line dropped 50 μL of the sample on a ¢ 10 mm paper disk, and an untreated paper disk was placed in the other shelter. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.

Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
[Test results]

  In the above test, when Solfit (Kuraray Co., Ltd.) was used, a high fixing inhibition effect similar to mint oil was confirmed. In contrast, the fixing inhibition rate of phenoxyethanol was -100%. Here, the fixing inhibition rate of −100% indicates that German cockroaches have invaded the treated area and did not enter the untreated area at all, as can be seen from Table 2 above. That is, the fixing inhibition rate of -100% indicates that the sample does not have the fixing inhibition effect, but may have attracted German cockroaches.

Test Example 2 Fixation inhibition efficacy test 2 against German cockroaches
[Sample]
The samples used are as follows:

[Test method]
Transparent resin shelter (top φ12cm, height approx. 10cm) at the four diagonal corners of a 50cm x 50cm square bat (bat height, 25cm) containing 50 German cockroaches (♂ / ♀ = 25/25) Four cups) were installed. One sheet of 100 mg treated specimen on φ11 cm filter paper was placed in two shelters on the diagonal, and untreated filter paper was placed on the other shelters. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.

Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
[Test results]

  Also in this test, when Solfit (Kuraray Co., Ltd.) was used, the fixing inhibition rate was confirmed to be significantly higher than methyl cellosolve and ethyl cellosolve and similar to mint oil.

Test Example 3 Fixation inhibition efficacy test 3 on German cockroaches
The repellent effect was evaluated using 3-methoxy-3-methyl-1-butanol as a monoether of Solfit (Kuraray Co., Ltd.) and other dihydric alcohols.
[Test method]
Release 50 cockroach cockroaches (♀ /／ = 25/25) on a 50cm x 50cm bat (bat height, 25cm), and install 4 pieces of 4cm x 1.5cm in / out cups in a transparent resin cup with a diameter of 9cm and a capacity of 200mL did. Two cups on the diagonal line were filled with 10 μL of a φ1 cm paper disk treated with the drug described below, and the remaining two were untreated. Near the center of the bat, one transparent resin cup containing water and food was installed in the center. The number of fixings was counted by standing overnight in a dark condition of 24 ° C. and 50% RH to determine the fixing inhibition rate.
Fixation inhibition rate (%) = 100 x (number of untreated districts-number of treated zones) / (number of untreated districts + number of treated zones)
[Samples and test results]

  When 3-methoxy-3-methyl-1-butanol was used, a high repellent effect was recognized as in the case of Solfit (Kuraray Co., Ltd.) and linalool.

Test Example 4 Fixation inhibition efficacy test 4 on German cockroaches
The fixing inhibition effect was also tested for butanol compounds other than Solfit (trade name of Kuraray Co., Ltd.) used in the above test examples.

[Sample]
The samples used are as follows:

[Test method]
Transparent resin shelter (top φ12cm, height) on the four corners of a 50cm x 50cm square bat (bat height, 10cm) containing 50 German cockroaches (♂ / ♀ = 25/25) About 10cm cup) was installed. One of the two shelters on the diagonal line dropped 50 μL of the sample on a φ10 mm paper disk, and an untreated paper disk was placed in the other shelter. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.

Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
[Test results]

[Discussion]
This time, all the compounds tested were found to have an anti-fixing effect. Therefore, it can be seen that monohydric alcohols or monoethers of dihydric alcohols having an alkylene group having 4 to 8 carbon atoms have a pest repellent effect.

Test Example 5 Fixation inhibition efficacy test 5 on German cockroaches
Pest repellent effect was evaluated using various ether compounds.

[Sample]
The samples used are as follows:

[Test method]
KP cup with 50 headed cockroaches (♂ / ♀ = 25/25), 50cm x 50cm square bat (bat height, 10cm) diagonally, 4 corners with 2x4cm edges as shelter Four lids (φ11 cm) were installed upside down. The two shelters on the diagonal line were laid with a filter paper of φ110 cm treated with 100 mg / sheet of specimen, and the other two shelters were untreated. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.
Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
The above test was performed twice. The number of fixing after one night and the fixing inhibition rate shown in Table 9 below are both average values of two tests.
[Test results]

  As apparent from Table 9 above, (1) isostearyl glyceryl ether, (2) POE oleyl ether (nonion E-202S n = 2 HLB4.9), (3) POE oleyl ether (nonion E-205S n) = 5 HLB9.0), (4) POE lauryl ether, (5) POE (1) POP (4) cetyl ether (PBC-31) and (6) POE lauryl ether n = 4 HLB 9.6) High repellent effect. In contrast, (7) triethylene glycol monomethyl ether, (8) POE stearyl ether (Neonion S-202 n = 2 HLB4.9), (9) POE stearyl ether (Neonion S-207 n = 7) HLB10.7) and (10) POE cetyl ether (nonion P-208 n = 8 HLB11.9) were remarkably inferior. In particular, (2) POE oleyl ether (nonionic E-202S n = 2 HLB4.9) is different from (8) POE stearyl ether (nonion S-202 n = 2 HLB4.9) in the presence or absence of a double bond. Except for having the same chemical structure, the repellent effect obtained was greatly different.

Test Example 6 Fixation inhibitory efficacy test 1 for black cockroaches
[Sample]
The samples used are as follows:

[Test method]
On a diagonal line of a 50cm x 50cm square bat (bat height, 10cm) containing 20 black wagtails (♂ / ♂ = 10/10), shelves made of transparent resin (top φ12cm, height) Four (about 10 cm cups) were installed. One sheet of 100 mg treated specimen on φ11 cm filter paper was placed in two shelters on the diagonal, and untreated filter paper was placed on the other shelters. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.

Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
[Test results]

Test Example 7 Fixation inhibitory potency test for black cockroaches 2
A repellency test was performed on black cockroaches of glycol ethers. In this test example, a paper disk having a diameter of 10 mm on which the specimen was dropped was used under a condition without contact evasion by using a paper disk having a small diameter.
[Sample]
The samples used are as follows:

[Test method]
On a diagonal line of a 33cm x 44cm bat (bat height, 10cm) containing 10 black wagtails (♂ / ♀ = 5/5), transparent resin shelters (upper φ8cm, height approx. Four 4cm cups) were installed. One of the two shelters on the diagonal line dropped 50 μL of the sample on a φ10 mm paper disk, and an untreated paper disk was placed in the other shelter. The mixture was left in a dark room, and the number of cockroaches in each shelter was counted to determine the fixing inhibition rate.

Fixation inhibition rate (%) = 100 x (number of untreated zones-number of treated zones) / (number of untreated zones + number of treated zones)
[Test results]

Test Example 8 Fixation inhibitory efficacy test against Drosophila melanogaster [Sample]
The samples used are as follows:

[Test method]
Leave a commercially available banana for several days, crush it, and mix it so that the sample becomes 3% and 10% (W / W). 1.5 g of the mixture is placed in a transparent resin container having a diameter of φ6 cm and a depth of 5 mm and placed in a cage of 25 cm × 25 cm × 25 cm (4 to 5 samples). Among them, 50 Drosophila melanogaster were released, left for 2 hours, and the number of flies on and near the banana treated with the drug was counted. The test was repeated twice and the total was shown. The repellent rate of each specimen is shown in Table 15 below.

Repellent rate = 100 x (total number of untreated areas-total number of treated areas) / total number of untreated areas)
[Test results]

[Discussion]
As for Solfit (Kuraray Co., Ltd.), a high repellent effect comparable to or higher than Diet was confirmed. On the other hand, with respect to methyl cellosolve, only a very low repellent effect was observed.

Test Example 9 Fixation inhibitory potency test for red ants [specimen]
The samples used are as follows:

[Test method]:
A φ1 cm filter paper was cut in half, and 0.5 ml of an acetone solution prepared to a predetermined concentration so that the sample was 25 mg and 50 mg was uniformly applied. After air-drying for 20 minutes, this treated filter paper was placed on the plastic container (KP cup lid) side by side with the remaining half of the untreated filter paper, and a cylinder (diameter 6 cm, height 1. 5 cm) was placed in the center of the filter paper. Ten caterpillars were released in the cylinder, and the number of ants on the drug-treated paper after 20 minutes was counted. The test was repeated twice and the total was shown. The repelling rate of each specimen is shown in the table below.

Repellent rate = 100 x (total number of invading untreated areas-total number of invading treated areas) / total number of test insects)
[Test results]
Table 17 below shows the contact repellent effect of each specimen:

[Discussion]
When Solfit (Kuraray Co., Ltd.) was used, the same high repellent effect as Diet was observed at both 25 mg and 50 mg concentrations. On the other hand, when methyl cellosolve was used, the repellent effect was remarkably inferior. From these facts, it can be seen that the pest repellent of the present invention has a very high repellent effect against ants.

Test Example 10 Aedes albopictus [specimen]
The samples used were as follows:

[Test method] (mosquito repellent test):
The specimen was uniformly applied to the palm so that the specimen was 100 mg and 300 mg. This palm was applied to one side of a cage (25 cm × 25 cm × 25 cm high-density mesh) containing 30 adult females of Aedes albopictus and the number of landings per minute was counted. The test was repeated twice and the total was shown. The repelling rate of each specimen is shown in the table below.

Repellent rate = 100 x (total number of landings in untreated area-total number of landings in treated area) / total landing in untreated area [Test results]
Table 19 below shows the repellent effect of each specimen.

[Discussion]
Also in this test, when Solfit (Kuraray brand name) was used, a higher repellent effect than Diet was confirmed at all concentrations. On the other hand, with respect to methyl cellosolve and ethyl cellosolve, the repelling rate was remarkably low. From these facts, it can be seen that the pest repellent of the present invention is also excellent in repellency against mosquitoes.

Example 1 3 parts by weight of the compound (1), 1 part by weight of silicon oxide and 96 parts by weight of cyclododecane were sufficiently crushed and mixed, and then compressed to 10 g / tablet under a pressure of 300 kg / cm ³ to form a tablet. The pest repellent composition of the present invention was obtained.

Example 2 Compound (1) is added to 10 g of a small amount of fragrance, 20 ml of ethyl cellosolve and 150 ml of odorless kerosene, and 150 ml of a mixture of liquefied petroleum gas and dimethyl ether (50:50 volume ratio). The pest repellent composition of the present invention in the form of an aerosol was obtained by filling a can (content 400 ml), sealing it on an injection device and sealing it.

Example 3 5 g of compound (1), 25 g of nitrocellulose, 25 g of thinner and 2 g of dibutyl phthalate were mixed and dissolved to obtain a pest repellent composition of the present invention in the form of a paint.

Example 4 5 g of compound (1), 20 g of ethyl cellosolve, and 75 g of odorless kerosene were mixed to obtain a pest repellent composition of the present invention having the form of an oil.

Example 5 5 g of the compound (1), 10 g of polyoxyethylene oleyl ether (15 mol of ethylene oxide added) and 85 g of water were mixed to obtain a pest repellent repellent composition of the present invention having the form of a preparation.

Example 6 Compound (1) (10 g), propylene glycol (5 g), isopropyl myristate (2 g), purified water (15 g), a small amount of a fragrance, and ethanol (68 g) were mixed to obtain a pest repellent composition of the present invention having a preparation form.

Example 7 5 g of compound (1) and 5 g of N- (2-ethylhexyl) -bicyclo- [2,2,1] -5-heptene-2,3-dicarboximide as an efficacy enhancer in 1 liter of n-hexane Dilute, impregnate a non-woven fabric (polyethylene-cotton (3: 1 weight ratio), thickness 300 μ, area 1 m ² ) so that the test compound (1) is 30 g, and dry to obtain a sheet-like form. The present pest repellent was obtained.

Example 8 6 parts by weight of the compound (1) was mixed with 94 parts by weight of 2,4,6-triisopropyl-1,3,5-trioxane and then heated and dissolved at about 90 ° C. Pests of the present invention in the form of a pest repellent holding material by impregnating with a solution of about 25% of the weight of the wood by dipping in a thickness of × 150 cm × 2 cm) and pressurizing at 15 kg / cm ² A repellent was obtained.

Claims (2)

3-methoxy-3-methyl-1-butanol, 3-methoxy-1-butanol, 1-methoxy-2-butanol, isostearyl glyceryl ether, POE oleyl ether (n = 2 or n = 5); POE lauryl ether ( n = 2 or n = 4); POE (1) POP (4) cetyl ether; insect pests against cockroaches containing at least one selected from the group consisting of 1-butanol and 4-phenyl-1-butanol as an active ingredient Repellent. A cockroach repellent method for repelling cockroaches using the pest repellent according to claim 1 .