JPH0558930A - 2-(1-hydroxy-isopropyl)-5-methyl-cylopentanol - Google Patents
2-(1-hydroxy-isopropyl)-5-methyl-cylopentanolInfo
- Publication number
- JPH0558930A JPH0558930A JP25053391A JP25053391A JPH0558930A JP H0558930 A JPH0558930 A JP H0558930A JP 25053391 A JP25053391 A JP 25053391A JP 25053391 A JP25053391 A JP 25053391A JP H0558930 A JPH0558930 A JP H0558930A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methyl
- isopropyl
- hydroxy
- cyclopentanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、それ自体実質的に無臭
の化合物であって、有害生物忌避剤として極めて優れた
持続効果を有する新規化合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel compound which is substantially odorless in itself and has an extremely long-lasting effect as a pest repellent.
【0002】[0002]
【従来の技術及び発明が解決しようとする課題】蚊等の
有害生物から身を守るための有害生物忌避剤として、従
来N,N−ジエチルトルアミドが広く用いられている。
しかしながら、このN,N−ジエチルトルアミドは、特
異な臭いがある等の問題を有しているため、新規な有害
生物忌避剤の開発が望まれていた。本発明は、このよう
な実情に鑑みなされたものであって、その目的は、優れ
た有害生物忌避効果を有し、特異の臭いを有さず、且つ
持続効果を有する新規化合物を提供することにある。Conventionally, N, N-diethyltoluamide has been widely used as a pest repellent for protecting oneself from pests such as mosquitoes.
However, since this N, N-diethyltoluamide has a problem that it has a peculiar odor, the development of a new pest repellent has been desired. The present invention has been made in view of such circumstances, and an object thereof is to provide a novel compound having an excellent pest repellent effect, having no peculiar odor, and having a sustained effect. It is in.
【0003】[0003]
【課題を解決するための手段】本発明者らは、上記の目
的を達成するために鋭意研究した結果、新規化合物の合
成に成功し、且つこの化合物が優れた有害生物忌避効果
とその持続性を有することを見出した。即ち、本発明の
新規化合物は、下記構造式Means for Solving the Problems As a result of intensive studies for achieving the above object, the present inventors have succeeded in synthesizing a novel compound, and this compound has an excellent pest repellent effect and its persistence. Have been found. That is, the novel compound of the present invention has the following structural formula
【化2】 で表される2−(1−ヒドロキシ−イソプロピル)−5
−メチル−シクロペンタノールである。[Chemical 2] 2- (1-hydroxy-isopropyl) -5 represented by
-Methyl-cyclopentanol.
【0004】以下、本発明の構成の詳細について説明す
る。本発明の2−(1−ヒドロキシ−イソプロピル)−
5−メチル−シクロペンタノールは、2,6−ジメチル
−5−ヘプテナールを硫酸等の酸水溶液と混合撹拌する
ことにより得ることができる。このようにして得られた
2−(1−ヒドロキシ−イソプロピル)−5−メチル−
シクロペンタノールは、臭いもほとんどない淡黄色の油
状物である。The details of the configuration of the present invention will be described below. 2- (1-hydroxy-isopropyl) -of the present invention
5-Methyl-cyclopentanol can be obtained by mixing 2,6-dimethyl-5-heptenal with an aqueous acid solution such as sulfuric acid and stirring. 2- (1-hydroxy-isopropyl) -5-methyl-obtained in this way
Cyclopentanol is a pale yellow oil with almost no odor.
【0005】そして、この油状物質にカラム処理等を施
し、シス体及びトランス体を単離することにより結晶と
して取り出すこともできる。この2−(1−ヒドロキシ
−イソプロピル)−5−メチル−シクロペンタノール
は、シス体及びトランス体のいずれでも蚊等の有害生物
に対する忌避効果に優れている。Then, the oily substance can be subjected to a column treatment or the like to isolate the cis form and the trans form, whereby the oily substance can be taken out as crystals. This 2- (1-hydroxy-isopropyl) -5-methyl-cyclopentanol has an excellent repellent effect against pests such as mosquitoes in both cis and trans forms.
【0006】本発明の2−(1−ヒドロキシ−イソプロ
ピル)−5−メチル−シクロペンタノールを有功成分と
して、通常に用いられる化粧料または医薬品の基剤(ベ
ース)に配合することによって、種々の剤型の有害生物
忌避剤を得ることが可能である。そして、その化合物の
含有量は、製剤形態、使用方法、その他の条件によって
異なるが、一般的にはその配合量は0.1%〜90%で
あり、特に3%〜20%とすることが好ましい。By incorporating 2- (1-hydroxy-isopropyl) -5-methyl-cyclopentanol of the present invention as a useful ingredient into a base of cosmetics or pharmaceuticals which is usually used, various compounds can be prepared. It is possible to obtain pest repellents in dosage form. The content of the compound varies depending on the formulation form, method of use, and other conditions, but the content is generally 0.1% to 90%, and particularly 3% to 20%. preferable.
【0007】このようにして得られた本発明の化合物
は、ヒストジマカ等の蚊、ヤスデ、ヨトウムシ、ナメク
ジ等の有害生物に使用される。The thus-obtained compound of the present invention is used for pests such as mosquitoes such as Aedes albopictus, millipedes, millet and slugs.
【0008】[0008]
【実施例】以下、実施例を挙げて本発明を更に具体的に
説明する。尚、以下における%表示は、特に指定しない
限り重量%を意味する。EXAMPLES The present invention will be described in more detail below with reference to examples. In addition, unless otherwise specified, the% display in the following means% by weight.
【0009】実施例1 2,6−ジメチル−5−ヘプテナール(melona
l、ジボダン社製)50gを20%硫酸水溶液300g
中に徐々に添加した後、20時間激しく混合撹拌し、こ
の反応溶液より150mlのジエチルエーテルを用いて
抽出した。そして、ジエチルエーテル層を10%炭酸ナ
トリウム水溶液100mlにて2度洗浄した後、更に飽
和食塩水100mlにて2度洗浄した。Example 1 2,6-Dimethyl-5-heptenal (melona)
50 g of 20% sulfuric acid aqueous solution 300 g
After slowly adding the mixture therein, the mixture was vigorously mixed and stirred for 20 hours, and the reaction solution was extracted with 150 ml of diethyl ether. Then, the diethyl ether layer was washed twice with 100 ml of a 10% sodium carbonate aqueous solution and then twice with 100 ml of saturated saline.
【0010】このジエチルエーテル層を無水炭酸ナトリ
ウムにて乾燥後、ジエチルエーテルを除去することによ
り、粗反応生成物を得た。更に、この粗反応生成物をシ
リカゲルカラムクロマトグラフィー(展開溶媒 ヘキサ
ン/酢酸エチル=4/1)にて生成することにより、淡
黄色油状物35g(収率62%)を得た。The diethyl ether layer was dried over anhydrous sodium carbonate and the diethyl ether was removed to obtain a crude reaction product. Further, the crude reaction product was produced by silica gel column chromatography (developing solvent hexane / ethyl acetate = 4/1) to obtain 35 g (yield 62%) of a pale yellow oily substance.
【0011】得られた油状物のマススペクトル測定にお
いては、〔親ピーク分子量〕−15(メチル基由来)の
ピークを認め、元素分析においては、C=68.24
%、H=11.58%の実測値(C,Hの理論値はC=
68.31%、H=11.47%)を示した。更に、赤
外吸収スペクトルの測定によって、出発原料の2、6−
ジメチル−5−ヘプタナールのアルデヒド基に由来する
1740cm-1の吸収が消失し、3400cm-1及び1
180cm-1に水酸基の吸収を確認した。また、環状構
造に由来する吸収である1480cm-1、1040cm
-1、940cm-1に吸収を確認した。その結果、2−
(1−ヒドロキシ−イソプロピル)−5−メチル−シク
ロペンタノールの生成を確認した。In the mass spectrum measurement of the obtained oily substance, a peak of [parent peak molecular weight] -15 (derived from methyl group) was observed, and in elemental analysis, C = 68.24.
%, H = 11.58% measured value (theoretical value of C and H is C =
68.31%, H = 11.47%). Furthermore, by measuring the infrared absorption spectrum, 2,6-
Absorption at 1740 cm -1 derived from the aldehyde group of dimethyl-5-heptanal disappeared, and 3400 cm -1 and 1
Absorption of hydroxyl groups was confirmed at 180 cm -1 . In addition, the absorption due to the ring structure is 1480 cm -1 , 1040 cm
Absorption was confirmed at -1 , 940 cm -1 . As a result, 2-
Formation of (1-hydroxy-isopropyl) -5-methyl-cyclopentanol was confirmed.
【0012】以下に、本発明の応用例を示す。 応用例1,2及び比較例1,2〔リペルローション〕 下記表1の組成に従って、応用例1,2及び比較例1,
2のリペルローションを調製し、下記有害生物忌避試験
を実施した。尚、N,N−ジエチルトルアミドは、従来
より有害生物忌避剤として用いられているものである。The application examples of the present invention are shown below. Application Examples 1 and 2 and Comparative Examples 1 and 2 [Liper Lotion] According to the composition of Table 1 below, Application Examples 1 and 2 and Comparative Example 1,
The repellent lotion of 2 was prepared and the following pest repellent test was conducted. Incidentally, N, N-diethyltoluamide has been conventionally used as a pest repellent.
【0013】[0013]
【表1】 [Table 1]
【0014】有害生物忌避試験 (1) 有害生物忌避効果及びその効果持続性の試験方
法 ヒストジマカの成虫に対する忌避効果を調べるために、
以下の試験を室温30℃、湿度70%の恒温室において
行った。左右の前腕に各試験試料を10ml塗布した
後、羽化後5〜7日経過したヒストジマカの成虫の雌雄
50匹づつが入った袋状の20cm×15cmの金網に
それぞれの腕を15分間差入れ、吸血の時間を与えた。
この施行を30分、1時間,2時間,4時間,6時間後
に行い、吸血の時間内の吸血の跡の数を求め、下記式か
ら忌避率を算出した。Pest repellent test (1) Test method of pest repellent effect and its effect persistence In order to examine repellent effect of Aedes albopictus on adults,
The following tests were conducted in a thermostatic chamber at room temperature of 30 ° C. and humidity of 70%. After 10 ml of each test sample was applied to the left and right forearms, each arm was inserted into a bag-shaped 20 cm × 15 cm wire net containing 50 adult male and female Aedes albopictus 5 to 7 days after emergence for 15 minutes, and blood was absorbed. I gave you time.
This treatment was performed after 30 minutes, 1 hour, 2 hours, 4 hours, and 6 hours, the number of blood-sucking traces within the blood-sucking time was determined, and the repellency rate was calculated from the following formula.
【数1】 X:試験液を塗布しない場合の吸血の跡の数 Y:試験液を塗布した場合の吸血の跡の数[Equation 1] X: Number of blood-sucking traces when test liquid was not applied Y: Number of blood-sucking traces when test liquid was applied
【0015】(2)結果 前記応用例1,2及び比較例1,2について、前記ヒス
トジマカ成虫に対する吸血忌避試験を行った。その結果
を表2に示した。表2から明らかなように、本発明の2
−(1−ヒドロキシ−イソプロピル)−5−メチル−シ
クロペンタノールは、優れた有害生物忌避効果としかも
その持続性を有していた。(2) Results For the application examples 1 and 2 and the comparative examples 1 and 2, a blood-sucking repellent test was conducted on the adult Aedes albopictus. The results are shown in Table 2. As is clear from Table 2, 2 of the present invention
-(1-Hydroxy-isopropyl) -5-methyl-cyclopentanol had an excellent pest repellent effect and its persistence.
【0016】[0016]
【表2】 [Table 2]
【0017】[0017]
【発明の効果】以上記載のように、本発明は、有害生物
忌避剤として優れた効果と持続性を有する2−(1−ヒ
ドロキシ−イソプロピル)−5−メチル−シクロペンタ
ノールが提供するものである。INDUSTRIAL APPLICABILITY As described above, the present invention provides 2- (1-hydroxy-isopropyl) -5-methyl-cyclopentanol having an excellent effect and durability as a pest repellent. is there.
Claims (1)
−メチル−シクロペンタノール。1. The following general structural formula: 2- (1-hydroxy-isopropyl) -5 represented by
-Methyl-cyclopentanol.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25053391A JP2840142B2 (en) | 1991-09-02 | 1991-09-02 | 2- (1-human-peroxy-isopropyl) -5-methyl-cyclopentanol |
US09/492,351 US6372804B1 (en) | 1991-09-02 | 2000-01-27 | Noxious-insect repellent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP25053391A JP2840142B2 (en) | 1991-09-02 | 1991-09-02 | 2- (1-human-peroxy-isopropyl) -5-methyl-cyclopentanol |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0558930A true JPH0558930A (en) | 1993-03-09 |
JP2840142B2 JP2840142B2 (en) | 1998-12-24 |
Family
ID=17209318
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP25053391A Expired - Fee Related JP2840142B2 (en) | 1991-09-02 | 1991-09-02 | 2- (1-human-peroxy-isopropyl) -5-methyl-cyclopentanol |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2840142B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6130255A (en) * | 1993-10-22 | 2000-10-10 | Ikemoto; Takeshi | Noxious-insect repellent |
-
1991
- 1991-09-02 JP JP25053391A patent/JP2840142B2/en not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6130255A (en) * | 1993-10-22 | 2000-10-10 | Ikemoto; Takeshi | Noxious-insect repellent |
US6677384B1 (en) * | 1993-10-22 | 2004-01-13 | Kanebo, Ltd. | Noxious-insect repellent |
WO2004091296A1 (en) * | 1993-10-22 | 2004-10-28 | Takeshi Ikemoto | Pest repellent |
Also Published As
Publication number | Publication date |
---|---|
JP2840142B2 (en) | 1998-12-24 |
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