JP4417040B2 - Mite control agent - Google Patents

Description

【化６】

【化７】

【化８】

（式中、Ｒ₁，Ｒ₂，Ｒ₃は、炭素数１〜１２の直鎖又は分岐を有するアルキル基を示す。また、Ｒ₄は、水素原子又は炭素数１〜１２の直鎖又は分岐を有するアルキル基を示す。）
【００１１】
ダニ防除剤として、所定のベンゾフェノン系化合物、又は所定のベンゾイン若しくはそのエーテル化合物を有効成分として含有する薬剤を使用するので、揮散性があまり高くないため、臭気が少なく、かつ、十分な効力持続力を有すると共に、毒性が低いという特徴を発揮することができる。
【００１２】
【発明の実施の形態】
以下において、この発明について詳細に説明する。
この発明にかかるダニ防除剤は、下記化学式（１）、（２）若しくは（３）のいずれかで表されるベンゾフェノン系化合物、又は下記化学式（４）で表されるベンゾイン若しくはそのエーテル化合物を有効成分として含有する薬剤である。
【００１３】
【化９】

【００１４】
【化１０】

【００１５】
【化１１】

【００１６】
【化１２】

【００１７】
上記の化学式において、Ｒ₁，Ｒ₂，Ｒ₃は、炭素数１〜１２の直鎖又は分岐を有するアルキル基を示す。また、Ｒ₄は、水素原子、又は炭素数１〜１２の直鎖又は分岐を有するアルキル基を示す。
【００１８】
上記化学式（１）や（２）で表されるベンゾフェノン系化合物の例としては、２−ヒドロキシ−４−メトキシベンゾフェノン、２−ヒドロキシ−４−オクトキシベンゾフェノン、２−ヒドロキシ−４−ドデシルオキシベンゾフェノン、２，２’−ジヒドロキシ−４−メトキシベンゾフェノン等があげられる。これらの中でも、２−ヒドロキシ−４−メトキシベンゾフェノン、２，２’−ジヒドロキシ−４−メトキシベンゾフェノンが特に効力が高く好ましい。
【００１９】
上記化学式（３）で表されるベンゾフェノン系化合物の例としては、ｏ−（メトキシカルボニル）ベンゾフェノン（別名：ｏ−ベンゾイル安息香酸メチル）等があげられる。
【００２０】
上記化学式（４）で表されるベンゾイン又はそのエーテル化合物の例としては、２−ヒドロキシ−２−フェニルアセトフェノン（すなわち、ベンゾイン）、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル等があげられる。この中でも、置換基のＲ₄が３以下である、ベンゾイン、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテルが特に効力が高く好ましい。
【００２１】
上記の各化合物は、固体担体、液体担体、ガス状担体等の担体に担持させたり、界面活性剤や塗膜成形剤等と混合させたりすることにより、乳剤、粉剤、油剤、エアゾール、塗布剤等に製剤化して用いることができる。また、上記の各化合物を微粒子化して、繊維加工用等製剤に製剤化して用いたり、樹脂に混練して製剤化して用いたりすることができる。
【００２２】
上記固体担体としては、ゼオライト、ベントナイト、珪藻土等があげられる。また、液体担体としては、ケロシン、灯油等の脂肪族炭化水素類、ジクロロエタン等のハロゲン化炭化水素、エタノール、イソプロパノール、エチレングリコール等のアルコール類等があげられる。さらに、ガス状担体としては、ジメチルエーテル、ＬＰＧ（液化天然ガス）等があげられる。
【００２３】
上記界面活性剤としては、アルキル硫酸エステル塩、アルキルスルホン酸塩、アリールスルホン酸塩等の陰イオン界面活性剤、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンソルビタン脂肪酸エステル、硬化ヒマシ油脂肪酸エステル等の非イオン界面活性剤があげられる。
また、上記塗膜形成剤としては、セルロース誘導体、ビニル系樹脂、ポリエステル系樹脂、ウレタン系樹脂等があげられる。
【００２４】
上記の各化合物を微粒子化する場合、得られる微粒子の粒子サイズとしては、１００μｍ以下がよく、１０μｍ以下が好ましい。微粒子化することにより、均一に処理ができ、繊維加工する際、効率的に繊維吸着される。粒子サイズが１００μｍより大きいと、均一に付着せず、効力がばらつく傾向がある。
【００２５】
上記の微粒子を繊維加工する方法は、特には制限がなく、パッドドライ法、高圧染色法等が例としてあげられる。
【００２６】
上記の微粒子を樹脂に混練する場合、使用される樹脂としては、ポリエチレン、ポリプロピレン等のポリオレフィン系樹脂、ポリスチレン、ＡＢＳ樹脂等のスチレン系樹脂、酢酸ビニル、塩化ビニル、メタクリル酸メチル等のビニル系ポリマーの単独重合体又は共重合体、ポリアミド樹脂、ポリエステル樹脂、ポリエーテル樹脂、ポリカーボネート樹脂、ポリウレタン樹脂等の熱可塑性樹脂があげられる。
【００２７】
上記樹脂は、フィルム、繊維、成型品等に成形されて使用される。上記繊維からは、各種の繊維製品や合成樹脂系綿等を製造することができる。このような成形に好適な熱可塑性樹脂としては、ポリエステル樹脂、ポリアミド樹脂やポリオレフィン樹脂があげられる。
【００２８】
上記の製剤化を行う場合、上記の各化合物の使用量は、製剤全体に対して、０．０１〜１０重量％がよく、０．１〜１重量％が好ましい。０．０１重量％より少ないと、十分な効力を発揮し得ない場合がある。一方、１０重量％より多いと、成形性に問題を生じ、繊維や成型品ができ難くなる場合がある。
【００２９】
この発明にかかるダニ防除剤には、必要に応じて、抗菌剤、防カビ剤、他の防虫剤、染料、酸化防止剤、紫外線吸収剤、着香料、消臭剤、分散剤、滑剤等を併用することができる。
【００３０】
このようにして得られた製剤は、極めて優れたダニの防除効果を発揮することができる。このダニ類としては、ヤケヒョウヒダニ、コナヒョウヒダニ等のチリダニ類、ヒゼンダニ等のヒゼンダニ類、ケナガコナダニ、ツメダニ等のコナダニ類等があげられる。
【００３１】
【実施例】
以下に実施例及び比較例をあげてこの発明をさらに具体的に説明する。まず、試験法及び各薬剤について説明する。
【００３２】
［臭気テスト］
所定の薬剤をアセトンに溶解し、綿１００％布（金巾 １００ｇ／ｍ²）に１００ｍｇ／ｍ²になるように均一にスプレー塗布し、１日乾燥して、薬剤含浸布を得、これを５人が臭いを嗅ぎ、下記の基準で評価した。結果は、３人以上が評価したものを選んだ。
○…臭いがほとんどしない。
×…刺激臭がした。
【００３３】
［ダニ忌避試験］
ダニ忌避試験は、侵入阻止法（防ダニ加工製品協議会指定法）により評価した。すなわち、シャーレの中に、上記臭気テストで作成した薬剤含浸布を敷き、中央に餌を置いた。そして、シャーレの周囲にダニ（ヤケヒョウダニ）１１００匹を配置して、シャーレ中央の餌までたどり着くダニの匹数を数えた。
【００３４】
所定の薬剤をスプレーしなかった布を用いた場合の、シャーレ中央の餌までたどり着くダニの匹数をａ、上記薬剤含浸布を用いた場合の、シャーレ中央の餌までたどり着くダニの匹数をｂとしたとき、忌避率を下記式から算出した。
忌避率（％）＝（ａ−ｂ）／ａ×１００
この忌避率が５０％以上の場合に、優れた忌避効果を有すると、侵入阻止法（防ダニ加工製品協議会指定法）では規定している。
【００３５】
［薬剤］
・２−ヒドロキシ−４−メトキシベンゾフェノン…共同薬品（株）製：Ｖｉｏｓｏｒｂ１１０
・２，２’−ジヒドロキシ−４−メトキシベンゾフェノン…ケミプロ化成（株）製：ＫＥＭＩＳＯＲＢ１１１
【００３６】
・２−ヒドロキシ−４−ｎ−オクトキシベンゾフェノン…共同薬品（株）製：Ｖｉｏｓｏｒｂ１３０
・ｏ−（メトキシカルボニル）ベンゾフェノン…東京化成（株）製：試薬
【００３７】
・ベンゾイン…東京化成（株）製：試薬
・ベンゾインエチルエーテル…東京化成（株）製：試薬
【００３８】
・ベンゾインイソプロピルエーテル…東京化成（株）製：試薬
・ベンゾインイソブチルエーテル…東京化成（株）製：試薬
【００３９】
・ベンゾフェノン…東京化成（株）製：試薬
・２−ヒドロキシベンゾフェノン…東京化成（株）製：試薬
【００４０】
・２，４−ジヒドロキシベンゾフェノン…共同薬品（株）製：Ｖｉｏｓｏｒｂ１００
・２，２’、４，４’−テトラヒドロキシベンゾフェノン…共同薬品（株）製：Ｖｉｏｓｏｒｂ１０５
【００４１】
・ドデカンニ酸ジ−ｎ−ブチル…田岡化学工業（株）製
・ｏ−ベンゾイル安息香酸…東京化成（株）製：試薬
【００４２】
（実施例１〜８、比較例１〜６）
表１に記載の薬剤を用いて、臭気テストに記載の方法にしたがって薬剤含浸布を作成した。そして、得られた薬剤含浸布を用いて、ダニ忌避試験に供与した。その結果を表１に示す。
【００４３】
【表１】

【００４４】
【発明の効果】
この発明によると、ダニ防除剤として、所定のベンゾフェノン系化合物、又は所定のベンゾイン若しくはそのエーテル化合物を有効成分として含有する薬剤を使用するので、揮散性があまり高くないため、臭気が少なく、かつ、十分な効力持続力を有すると共に、毒性が低く、無色であるという特徴を発揮することができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a tick control agent, particularly an indoor mite control agent.
[0002]
[Prior art]
In recent years, with the change of architectural style and the comfort of living environment due to the widespread use of air conditioning facilities, a lot of indoor ticks are generated, causing not only discomfort but also causing allergies, which is a big social problem.
[0003]
Conventionally, as an indoor mite control agent, organic phosphorus agents such as fenitrothion and diazinon, carbamate agents such as carbaryl, and pyrethroid agents such as permethrin and phenothrin are used, and aerosols, aqueous agents, emulsions, It is used in various forms by spraying directly in the form of an oil agent, impregnating a carpet, kneading into a resin and forming into a film or the like.
[0004]
Further, as compounds other than the above-mentioned insect repellents, many compounds having a tick repellent activity on alkyl esters of aliphatic or aromatic carboxylic acids are known, such as Patent Documents 1-5.
[0005]
Furthermore, it is known from Patent Documents 6 to 8 that benzophenone and 2-hydroxybenzophenone have a mite repellent effect.
[0006]
[Patent Document 1]
JP-A-4-108171 [Patent Document 2]
JP-A-6-25971 [Patent Document 3]
JP-A-8-92010 [Patent Document 4]
Japanese Patent Publication No. 5-8682 [Patent Document 5]
Japanese Patent Publication No. 1-13682 [Patent Document 6]
JP-A-5-178712 [Patent Document 7]
Japanese Patent No. 2854185 [Patent Document 8]
Japanese Patent No. 2993729 [0007]
[Problems to be solved by the invention]
However, the above organic phosphorus agents, carbamate agents, pyrethroid agents, and the respective mite control agents described in Patent Documents 1 to 5, etc. are toxic, odorous, control spectrum, thermal decomposition when processed into resins and fibers. It is hard to say that it is necessarily sufficient in terms of etc.
[0008]
On the other hand, each of the mite control agents described in Patent Documents 6 to 8 has a sufficient effect in terms of toxicity, control spectrum, decomposition by heat when processed into a resin or fiber, but is volatilized. Because it is easy, it has an odor, lacks long-term efficacy sustainability, and since the medicine itself is colored, fibers and the like may be colored.
[0009]
Accordingly, an object of the present invention is to provide a benzophenone-based compound or a neighboring compound having low toxicity, sufficient potency, colorlessness, and low odor as a tick control agent.
[0010]
[Means for Solving the Problems]
The present invention provides a tick containing as an active ingredient a benzophenone-based compound represented by any one of the following chemical formulas (1), (2) or (3), or a benzoin represented by the following chemical formula (4) or an ether compound thereof. The above problems have been solved by using a control agent.
[Chemical formula 5]

[Chemical 6]

[Chemical 7]

[Chemical 8]

(Wherein R ₁ , R ₂ and R ₃ represent a linear or branched alkyl group having 1 to 12 carbon atoms. R ₄ represents a hydrogen atom or a linear or branched chain having 1 to 12 carbon atoms. Represents an alkyl group having
[0011]
As a tick control agent, a chemical containing a specified benzophenone compound or a specified benzoin or its ether compound as an active ingredient is used, so the volatility is not so high, so there is little odor and sufficient potency And can exhibit the characteristics of low toxicity.
[0012]
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be described in detail below.
The mite control agent according to the present invention effectively uses a benzophenone compound represented by any one of the following chemical formulas (1), (2) or (3), or a benzoin represented by the following chemical formula (4) or an ether compound thereof. It is a drug contained as a component.
[0013]
[Chemical 9]

[0014]
[Chemical Formula 10]

[0015]
Embedded image

[0016]
Embedded image

[0017]
In the above _{formula, R 1, R 2, R} 3 represents a linear or branched alkyl group having 1 to 12 carbon atoms. R ₄ represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms.
[0018]
Examples of the benzophenone compounds represented by the chemical formulas (1) and (2) include 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone, 2,2′-dihydroxy-4-methoxybenzophenone and the like. Among these, 2-hydroxy-4-methoxybenzophenone and 2,2′-dihydroxy-4-methoxybenzophenone are particularly preferable because of their high efficacy.
[0019]
Examples of the benzophenone compound represented by the chemical formula (3) include o- (methoxycarbonyl) benzophenone (also known as methyl o-benzoylbenzoate).
[0020]
Examples of the benzoin represented by the chemical formula (4) or an ether compound thereof include 2-hydroxy-2-phenylacetophenone (that is, benzoin), benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and the like. Among these, benzoin, benzoin ethyl ether, and benzoin isopropyl ether, in which R _{4 of} the substituent is 3 or less, are particularly preferable because of their high efficacy.
[0021]
Each of the above compounds is supported on a carrier such as a solid carrier, a liquid carrier, or a gaseous carrier, or mixed with a surfactant, a film forming agent, or the like, to thereby form an emulsion, powder, oil, aerosol, or coating agent. Etc. and can be used as a formulation. Further, each of the above compounds can be made into fine particles and formulated into a preparation for fiber processing or the like, or kneaded into a resin and formulated into a formulation.
[0022]
Examples of the solid carrier include zeolite, bentonite, and diatomaceous earth. Examples of the liquid carrier include aliphatic hydrocarbons such as kerosene and kerosene, halogenated hydrocarbons such as dichloroethane, alcohols such as ethanol, isopropanol, and ethylene glycol. Furthermore, examples of the gaseous carrier include dimethyl ether and LPG (liquefied natural gas).
[0023]
Examples of the surfactant include anionic surfactants such as alkyl sulfate esters, alkyl sulfonates, and aryl sulfonates, polyoxyethylene alkyl ethers, polyoxyethylene sorbitan fatty acid esters, and hardened castor oil fatty acid esters. Examples thereof include ionic surfactants.
Examples of the coating film forming agent include cellulose derivatives, vinyl resins, polyester resins, and urethane resins.
[0024]
When each of the above compounds is formed into fine particles, the particle size of the obtained fine particles is preferably 100 μm or less, and preferably 10 μm or less. By making the particles fine, the treatment can be performed uniformly, and the fibers are efficiently adsorbed when the fibers are processed. When the particle size is larger than 100 μm, the particles do not adhere uniformly and the efficacy tends to vary.
[0025]
The method for fiber processing the fine particles is not particularly limited, and examples thereof include a pad dry method and a high pressure dyeing method.
[0026]
When the fine particles are kneaded with the resin, the resins used include polyolefin resins such as polyethylene and polypropylene, styrene resins such as polystyrene and ABS resin, vinyl polymers such as vinyl acetate, vinyl chloride, and methyl methacrylate. And a thermoplastic resin such as a polyamide polymer, a polyester resin, a polyether resin, a polycarbonate resin, and a polyurethane resin.
[0027]
The resin is used after being formed into a film, fiber, molded product or the like. From the above fibers, various fiber products and synthetic resin cotton can be produced. Examples of thermoplastic resins suitable for such molding include polyester resins, polyamide resins, and polyolefin resins.
[0028]
When the above formulation is performed, the amount of each compound used is preferably 0.01 to 10% by weight, and preferably 0.1 to 1% by weight, based on the entire formulation. If it is less than 0.01% by weight, sufficient efficacy may not be exhibited. On the other hand, if it is more than 10% by weight, there is a problem in moldability, and it may be difficult to produce fibers or molded products.
[0029]
As necessary, the mite control agent according to the present invention includes an antibacterial agent, a fungicide, another insect repellent, a dye, an antioxidant, an ultraviolet absorber, a flavoring agent, a deodorant, a dispersant, a lubricant, and the like. Can be used together.
[0030]
The preparation thus obtained can exhibit an extremely excellent mite control effect. Examples of the mites include dust mites such as the leopard mite and the leopard mite, hymenid mites such as the mites, and mites such as the mite mites and the tick mites.
[0031]
【Example】
The present invention will be described more specifically with reference to the following examples and comparative examples. First, the test method and each drug will be described.
[0032]
[Odor test]
A predetermined drug is dissolved in acetone, sprayed uniformly on 100% cotton cloth (gold width 100 g / m ² ) so as to be 100 mg / m ² , and dried for one day to obtain a drug-impregnated cloth. A person smelled the odor and evaluated it according to the following criteria. The result was selected by more than 3 people.
○… Small smell.
X: There was an irritating odor.
[0033]
[Tick repellent test]
The tick repellent test was evaluated by the invasion prevention method (designated by the Mite Prevention Products Association). That is, a chemical-impregnated cloth prepared by the above odor test was laid in a petri dish, and food was placed in the center. Then, 1100 ticks (yander leopard mites) were placed around the petri dish, and the number of ticks reaching the food in the center of the petri dish was counted.
[0034]
The number of mites that reach the food in the center of the petri dish when using a cloth that has not been sprayed with the prescribed drug is a, and the number of mites that reach the food in the center of the petri dish when the cloth impregnated with the drug is b. The repelling rate was calculated from the following formula.
Repelling rate (%) = (a−b) / a × 100
When this repelling rate is 50% or more, the invasion prevention method (designated method of anti-tick processing product council) stipulates that it has an excellent repelling effect.
[0035]
[Drug]
・ 2-hydroxy-4-methoxybenzophenone: manufactured by Kyodo Yakuhin Co., Ltd .: Biosorb110
・ 2,2′-dihydroxy-4-methoxybenzophenone: manufactured by Chemipro Kasei Co., Ltd .: KEMISORB111
[0036]
-2-hydroxy-4-n-octoxybenzophenone ... manufactured by Kyodo Pharmaceutical Co., Ltd .: Biosorb130
O- (methoxycarbonyl) benzophenone: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagent
• Benzoin: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents • Benzoin ethyl ether: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents
• Benzoin isopropyl ether: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents • Benzoin isobutyl ether: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents
Benzophenone: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents 2-hydroxybenzophenone: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents
・ 2,4-Dihydroxybenzophenone: manufactured by Kyodo Yakuhin Co., Ltd .: Biosorb100
・ 2,2 ′, 4,4′-tetrahydroxybenzophenone: manufactured by Kyodo Yakuhin Co., Ltd .: Viosorb 105
[0041]
・ Didecanoic acid di-n-butyl: manufactured by Taoka Chemical Co., Ltd. o-benzoylbenzoic acid: manufactured by Tokyo Chemical Industry Co., Ltd .: Reagents
(Examples 1-8, Comparative Examples 1-6)
Using the drugs described in Table 1, a drug-impregnated cloth was prepared according to the method described in the odor test. The obtained drug-impregnated fabric was used for a tick repellent test. The results are shown in Table 1.
[0043]
[Table 1]

[0044]
【The invention's effect】
According to this invention, as a mite control agent, since a chemical containing a predetermined benzophenone compound or a predetermined benzoin or an ether compound thereof as an active ingredient is used, the volatility is not so high, so there is little odor, and It can exhibit the characteristics that it has a sufficient potency and has low toxicity and is colorless.

Claims (2)

The tick control agent which contains the benzophenone type compound represented by either the following chemical formula (1), chemical formula (2), or chemical formula (3) as an active ingredient.

(In the formula, R ₁ , R ₂ and R ₃ represent a linear or branched alkyl group having 1 to 12 carbon atoms.) A tick control agent containing benzoin represented by the following chemical formula (4) or an ether compound thereof as an active ingredient.

(In the formula, R ₄ represents a hydrogen atom or a linear or branched alkyl group having 1 to 12 carbon atoms.)