JP2008120762A - Incense stick for flytrap - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a useful incense stick for flytrap containing a selected active ingredient which has a higher insecticidal effect against mosquitoes as well as flies than that of the conventional Pynamin Forte incense stick in the form of an incense stick. <P>SOLUTION: The flytrap incense stick comprises 0.05-0.5 mass% 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropane carboxylate as an active ingredient and N-(2-ethylhexyl)-bicyclo[2,2,1]-hept-5-ene-2,3-dicarboxyimide based on the chemical formula as an effect enhancer in an amount of 0.1 or more times the amount of the active ingredient. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

The present invention relates to an improvement of a fly catching incense stick.

Mosquito coils are familiar for more than 100 years as insecticides for combating mosquitoes, and their active ingredients are (±) -2-allyl- because of their heat transpiration and thermal stability. 3-methyl-cyclopent-2-en-1-one-4-yl (+)-cis, trans-chrysantemate (hereinafter referred to as pinamine forte) and its stereoisomers, such as esbiothrin and esviol The chrysanthemum ester compounds such as are widely used. On the other hand, the occurrence of flies is decreasing in urban areas, but there are more opportunities to suffer than before in fishing villages, seafood processing plants, garbage disposal sites, livestock barns, poultry houses, and the like. Insecticides such as emulsions, oils, and powders are used as countermeasures against flies. Spatial aerosols are widely used for adult insect control in general households, but have the disadvantage of being transient and lacking in sustainability. is there. Therefore, there is a demand for the development of an incense stick type that is a fly-removing incense stick, that is, a spatial treatment agent, has an effect that lasts for several hours, is more diffusive, and is effective even in an open scene.
Mosquito coils are a very reasonable form of insecticidal killing because they keep the spatial treatment in time with a single match and have constant potency until burned out. The active ingredient of the mosquito coil is volatilized from a site near 200 to 250 ° C. several mm away from the burning part, and this temperature is somewhat higher than the heating element temperature (120 to 170 ° C.) of the electric mosquito trap. Conventional pinamine forte-containing incense is known to have an active ingredient volatility of 60 to 80%, but its effectiveness against flies is weak. Application of was difficult.

The present inventors have selected empentrin with the highest vapor pressure among commercially available pyrethroids as an active ingredient, and have already developed a fly-removing incense stick (Patent No. 3001169: Patent Document 1), which is costly. In addition, the volatility was too high and loss in the drying process during production was inevitable. Accordingly, the selection of an effective ingredient optimal for a fly-cranking incense is an important issue. For example, JP-A-10-203905 (Patent Document 2) discloses 2-allyl-3-methyl-cyclopent-2-ene- Although a fly-removing incense stick having 1-on-4-yl 2,2,3,3-tetramethylcyclopropanecarboxylate as an active ingredient has been disclosed, it was not always satisfactory. JP 2001-11022 A (Patent Document 3) describes 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3- (2-methyl-1-propenyl). Although it is described that the mosquito coil incense containing cyclopropanecarboxylate was effective against Culex pipiens, there is no description about the efficacy evaluation against the fly of the incense stick form.
Further, the fly-removing incense disclosed in JP-A-2004-143151 (Patent Document 4) discloses 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropanecarboxy. Although the rate is listed as one of its active ingredients, it is just one example of many compounds, and there are special considerations for combining other drugs to enhance efficacy. is not.
Japanese Patent No. 3001169 JP-A-10-203905 JP 2001-11022 A JP 2004-143151 A

An object of the present invention is to select an active ingredient having an insecticidal effect higher than that of a conventional pinamin forte incense as well as a mosquito as well as a fly, and to provide a useful fly-removing incense containing the same. To do.

In order to solve the above-mentioned problems, the inventors have insecticidal efficacy against 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate flies, Focusing on the fact that the vapor pressure is located between the empentrin and pinamin forte, this compound was selected and an attempt was made to improve the fly picking incense. Thus, the present invention was completed by finding that a combination of the above-mentioned compound and a specific potency enhancer can provide a fly-cranking incense exhibiting a high killing effect and advantageous in cost.

に基づく４−メトキシメチル−２，３，５，６−テトラフルオロベンジル ２，２，３，３−テトラメチルシクロプロパンカルボキシレートを０．０５〜０．５質量％含有し、かつ効力増強剤として、Ｎ−（２−エチルヘキシル）−ビシクロ［２，２，１］−ヘプタ−５−エン−２，３−ジカルボキシイミドを、有効成分量に対して０．１倍量以上配合してなるハエ取り線香。
（２）効力増強剤として、Ｎ−（２−エチルヘキシル）−ビシクロ［２，２，１］−ヘプタ−５−エン−２，３−ジカルボキシイミドを、有効成分量に対して２．０倍量以上配合してなる（１）記載のハエ取り線香。 That is, the present invention adopts the following configuration.
(1) As an active ingredient, the following chemical formula

Containing 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate based on 1 to 0.5% by mass and as a potentiator , N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide is blended at least 0.1 times the amount of the active ingredient. Taking incense sticks.
(2) As an efficacy enhancer, N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide is 2.0 times the active ingredient amount. The fly-removing incense according to (1), which is blended in an amount or more.

The fly picking incense of the present invention is based on the synergistic effect of the active ingredient and the potency enhancer, exhibits excellent effects on flies such as house flies and butterflies, can be manufactured at low cost, and is excellent in safety for human livestock. Therefore, its practicality is extremely high.

The active ingredient serving as a base in the fly-scenting incense of the present invention is 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate (hereinafter referred to as compound A). Called).
This compound is already known, and based on a usual synthesis method, the cyclopropanecarboxylic acid or a reactive derivative thereof and 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl alcohol or the reactivity thereof It can be prepared by reacting with a derivative.
Examples of the reactive derivative of carboxylic acid include acid halides, acid anhydrides, carboxylic acid lower alkyl esters, alkali metal salts, and salts with organic tertiary bases. On the other hand, examples of the reactive derivative of alcohol include chloride, bromide, and p-toluenesulfonic acid ester. The reaction is carried out in a suitable solvent, if necessary, in the presence of an organic or inorganic base or acid as a deoxidizing agent or catalyst as necessary.

Compound A is liquid at room temperature and is generally easily dissolved in an organic solvent. However, Compound A dissolved in the organic solvent and an incense base material such as wood flour are mixed to constitute the fly-removing incense stick of the present invention.
The active ingredient content in the fly picking incense is set to 0.05 to 0.5% by mass, preferably 0.15 to 0.3% by mass in consideration of insecticidal efficacy against various flies and economy.

The fly picking incense of the present invention is N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide (hereinafter, efficacy enhancer A) as an efficacy enhancer. Is blended in an amount of 0.1 times or more, preferably 2.0 times or more of the amount of the active ingredient.

Conventionally, in various preparations, piperonyl butoxide, N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide, N- (2-ethylhexyl) Often, pyrethroid synergists such as -1-isopropyl-4-methylbicyclo [2,2,2] -oct-5-ene-2,3-dicarboximide and octachlorodipropyl ether are mixed. I have been.
That is, when the above-mentioned synergist for pyrethroid is used for, for example, a liquid or a powder, it does not exhibit biological activity by itself, but is known to enhance the efficacy of pyrethroid when mixed with pyrethroid. There are many reports on the mechanism of synergists. For example, the body itself undergoes metabolic degradation to inhibit the oxidative detoxification metabolism of pyrethroids, or promote the penetration of pyrethroids into the skin, acting on the nervous system. It is known to increase the insecticidal efficacy of pyrethroids by making it easy to reach the point. However, the mechanism of action of such a synergist depends naturally on the type of insect, and the synergistic effect of the synergist is generally only about 10 to 20%.

On the other hand, the present inventors diligently studied the action of a certain compounding agent in the form of an incense stick, and surprisingly the insecticidal efficacy of a fly picking incense by adding compound A to potency enhancer A. It was found to be 3 times stronger. This fact cannot be explained only by the mechanism of the synergist conventionally used in pyrethroid preparations, that is, the insect physiological mechanism described above. As another cause, a certain substance contributes to an increase in the volatilization rate of the active ingredient and the active ingredient. It is thought that the physical action also contributes, such as raising the concentration in the air and promoting the diffusion of the volatilized active ingredient. Furthermore, it was confirmed by experiments that the volatilization rate of Compound A is increased by 5 to 10% by adding the potency enhancer A to Compound A.
That is, in the incense form, when the compound A is used in combination with the potency enhancer A in an appropriate amount, it is most efficiently volatilized by a kind of steam distillation together with water and potency enhancer A contained in the incense stick, The basic technical idea is that diffusion is facilitated and a remarkable synergistic effect can be achieved in combination with the effect of enhancing the physiological effects of insects. This is a completely new finding that has never been seen before.

By the way, N- (2-ethylhexyl) -1-isopropyl-4-methylbicyclo [2,2,2] -oct-5-ene-2,3-dicarboximide (hereinafter referred to as synergist S) is Although the chemical structure is similar to that of potency enhancer A, the potency enhancing effect was extremely low when used in combination with compound A incense. This is thought to be due to the fact that the transpiration of the synergist S under heated soot is considerably lower than that of the potency enhancer A. In the incense incense form, the transpiration properties of the active ingredient and the compounding agent are insecticidal. It can be evaluated as a test result that confirms that it is closely related to efficacy.

In the present invention, the quantitative ratio between compound A and potency enhancer A is also important. That is, in the range amount of from 0.1 to 2.0 times relative to the amount of active ingredient enhancer A, although higher potency enhancing effect knockdown effect represented by an index of KT ₅₀ values are obtained, KT ₉₀ There was a relatively small tendency for the potency-enhancing effect on value and mortality. Next, when the compounding amount of the efficacy enhancer A is increased to 2.0 times or more, the improvement in the KT ₅₀ value is not so large as to correspond to the compounding amount, but the efficacy enhancing effect on the KT ₉₀ value and lethality is It was found that the potency enhancer A can remarkably increase the knockdown effect and lethal action synergistically and synergistically. Thus, although the compounding quantity with respect to the active ingredient amount of the efficacy enhancer A is preferably 2.0 times or more, it is of course meaningless even if an extraordinary quantity is blended.

As an embodiment of the present invention, in addition to the efficacy enhancer A, a lower alkylamine salt of alkylbenzene sulfonic acid may be further blended as an adjuvant for the efficacy enhancing agent. Wherein the alkyl group of the alkyl benzene sulfonic acid is about C ₈ -C _14, whereas, lower alkyl group of the alkyl amine salt may be about C ₂ -C _4, for example, dodecylbenzenesulfonic acid isopropylamine salt and dodecyl benzene sulfonic acid A typical example is an ethylamine salt.
The ratio of the alkylbenzenesulfonic acid lower alkylamine salt to the efficacy enhancer A is suitably in the range of 0.2 to 1.0 times.

As a fly removing incense base material, there are a flame retardant and a binder, and the former includes plant powder such as wood powder, pesticide extracted chrysanthemum powder, tea leaf extracted powder, citrus skin powder, coconut shell powder, Carbon powders such as charcoal powder and elementary ash are listed. Examples of the latter binder include tab powder, starch, methyl cellulose, carboxymethyl cellulose and the like.

The fly picking incense of the present invention may contain a pigment, an antiseptic, a stabilizer, and the like, if necessary. Examples of the pigment include organic dyes such as malachite green, and typical examples of the preservative include acids such as sorbic acid, dehydroacetic acid, p-hydroxybenzoic acid, and salts thereof. Examples of the stabilizer include 2,6-di-tert-butyl-4-methylphenol (BHT) and 2,2′-methylenebis (4-ethyl-6-tertiary butylphenol), but are not limited thereto. Not.

Furthermore, as long as the gist of the present invention is not hindered, other insecticides and insect repellent components, such as conventional pyrethroid insecticides such as pyrethrin, allethrin, praretrin, flamethrin, transfluthrin, metfluthrin, empentrin, fungicides, antibacterial agents, A multipurpose composition having excellent efficacy can also be obtained by mixing repellents, fragrances, deodorants and the like.

In preparing the fly picking incense of the present invention, no special technique is required and a known production method can be employed. For example, water is added to a mixture of premix powder (a mixture of active ingredients, efficacy enhancers, etc. as part of the flame retardant) and the remaining incense base, and then kneaded. What is necessary is just to make a fly-removing incense stick after drying with a punching machine. Moreover, after molding using only the incense stick substrate, a liquid agent containing an active ingredient or the like may be sprayed or applied thereto.

The fly-cranking incense of the present invention is effective for flies such as house flies, fly flies, fly flies, fly flies, and flies, but of course sanitary pests such as mosquitoes, cockroaches, indoor dust mites, chironomids, abu It is also effective against various pests, and its practicality is extremely high.

Next, the fly removing incense stick of the present invention will be described in more detail based on specific examples.

Compound A (0.2 parts) and potency enhancer A (0.4 parts) are uniformly mixed with 99.4 parts of an incense base material such as pesticide extracted chrysanthemum powder, wood powder, starch, etc. The water containing was added, and the fly-removing incense stick of the present invention was obtained by a known method.

Compound A (0.15 parts), potency enhancer A (0.3 parts), and 2,6 di-tertiary butyl-4-methylphenol 0.1 parts, coconut shell powder, wood flour, tab flour After mixing uniformly with 99.45 parts of an incense base material such as starch, water containing an antiseptic was added, and the fly-incense incense of the present invention was obtained by a known method.

[Practical test in 25m ³ room]
In order to evaluate the performance of the fly picking incense according to the actual use conditions, a field efficacy test was conducted in a room of 25 m ³ .
That is, after releasing 100 adult house flies in a closed 25 m ³ room, a test fly-collecting incense (prepared according to Example 1 or Example 2) was placed in the center of the room. Table 1 shows the KT ₅₀ value, KT ₉₀ value, and mortality obtained by counting the adult housefly that had been exposed for 3 hours and fallen over time. For KT ₅₀ values exceeding 180 minutes, KT ₉₀ values and mortality were not calculated.

・効力増強剤Ａ：Ｎ−（２−エチルヘキシル）−ビシクロ［２，２，１］−ヘプタ−５−エン−２，３−ジカルボキシイミド
・共力剤Ｓ ：Ｎ−（２−エチルヘキシル）−１−イソプロピル−４−メチルビシクロ［２，２，２］−オクト−５−エン−２，３−ジカルボキシイミド
・化合物Ｂ：４−メトキシメチル−２，３，５，６−テトラフルオロベンジル ２，２−ジメチル−３−（２−メチル−１−プロペニル）シクロプロパンカルボキシレート（特開２００１−１１０２２号公報開示の化合物）

Efficacy enhancer A: N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide Synergist S: N- (2-ethylhexyl)- 1-isopropyl-4-methylbicyclo [2,2,2] -oct-5-ene-2,3-dicarboximide-Compound B: 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2 , 2-Dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate (compound disclosed in JP-A-2001-11022)

As a result of the test, compound A was contained in an amount of 0.05% by mass or more, and efficacy enhancer A {N- (2-ethylhexyl) -bicyclo [2,2,1] -hepta-5- The fly-scavenging incense of the present invention (present inventions 2 and 3) containing 0.1-2 or 1.0-fold amount of ene-2,3-dicarboximide} relative to compound A is an index of KT ₅₀ value. The shown enhanced knockdown effect was observed. In addition, when the compounding amount of the efficacy enhancer A with respect to Compound A is 2.0 to 5.0 times (Inventions 1 and 4 to 7), the knockdown effect indicated by the KT ₉₀ value index and the lethality In this respect, it was confirmed that the potency increase was remarkable, and a more reliable and stable insecticidal effect could be achieved. The above point is that when the present invention 6 in which the amount of the active ingredient is 0.15% by mass is compared with the comparative example 2, the present invention 6 is obtained by blending the potency enhancer A twice that of the active ingredient. , The KT ₅₀ value and the KT ₉₀ value were about ½, showing about twice the enhancement effect as the knockdown effect, and when the present invention 1 and the comparative example 2 were compared, the amount of the active ingredient ( Although the former is 1/3 of the latter in mass%), it is clear that the KT ₅₀ and KT ₉₀ values approximately the same as those of Comparative Example 2 were obtained in the present invention 1. Therefore, considering that the cost of potency enhancer A is very low compared to Compound A, it is clear that the fly-scavenging incense of the present invention is extremely useful and practical.
On the other hand, the mosquito coils of Comparative Compound A (Comparative Examples 1 to 3) not using the potency enhancer A were inferior in both the knockdown effect and the lethal effect. Also, as shown in Comparative Example 4, the synergist S {N- (2-ethylhexyl) -1-isopropyl-4-methylbicyclo [2,2,2] -oct-5-ene-2,3-di Carboximide} has a chemical structure similar to that of potency enhancer A and has a sufficient potency enhancing effect in the incense stick form of the present invention in combination with compound A, although it has been widely used as a synergist for pyrethroids. Not shown.
Furthermore, pinamin forte-containing incense sticks (Comparative Examples 5 to 6) were almost ineffective against flies even at high concentrations. In addition, the mosquito coil incense disclosed in Japanese Patent Application Laid-Open No. 2001-11022 and containing compound B as an active ingredient is effective against squid, but the chemical structure is similar to compound A, but comparative examples 7-8 As shown in Fig. 2, it was almost ineffective against the house fly, and the effect of enhancing potency by adding potency enhancer A was poor. Accordingly, it was found that the excellent insecticidal efficacy and significant potency enhancing effect on flies was selectively based on the combination of Compound A and Potency Augmenting Agent A.

Compound (A) 0.2 part, potency enhancer (A) 0.4 part, dodecylbenzenesulfonic acid isopropylamine 0.2 part and stabilizer (2,6-ditertiarybutyl-4-methylphenol) 0.3 part of the mixture was uniformly mixed with 98.9 parts of a base material for incense sticks such as pesticide extracted chrysanthemum powder, wood powder, starch, etc., and the fly-removing incense stick of the present invention was obtained by a known method. When this volume (13 g) was used in a 6 tatami room, it was possible to completely control flies and mosquitoes over a period of about 7 and a half hours.

The fly-harvesting incense stick of the present invention obtained in Example 4 was put into a hanging incense stick dish, and it was lowered to the waist and engaged in work in a barn where many flies were generated, but it was bothered by fly for about 7 hours There was no.
Similarly, when this incense stick was used in a house where there was a pig farm nearby and there was a lot of flies invading, it was not possible to see flies invading.

INDUSTRIAL APPLICABILITY The present invention can be used in the field of manufacturing and selling fly incense sticks.

Claims (2)

As an active ingredient, the following chemical formula

Containing 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate based on 1 to 0.5% by mass and as a potentiator N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide is blended in an amount of 0.1 times or more with respect to the amount of the active ingredient. A fly-removing incense stick characterized by. As an efficacy enhancer, N- (2-ethylhexyl) -bicyclo [2,2,1] -hept-5-ene-2,3-dicarboximide is added in an amount of 2.0 times or more with respect to the amount of active ingredient. The fly-removing incense stick according to claim 1, wherein