JP3156867B2 - 2-hydroxymethyl-cycloalkanol derivative - Google Patents
2-hydroxymethyl-cycloalkanol derivativeInfo
- Publication number
- JP3156867B2 JP3156867B2 JP04808892A JP4808892A JP3156867B2 JP 3156867 B2 JP3156867 B2 JP 3156867B2 JP 04808892 A JP04808892 A JP 04808892A JP 4808892 A JP4808892 A JP 4808892A JP 3156867 B2 JP3156867 B2 JP 3156867B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxymethyl
- cyclohexanol
- present
- butyl
- pest repellent
- 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.)
- Expired - Lifetime
Links
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
持続効果を有する化合物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound which is substantially odorless by 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に有害生物忌避剤としてＮ，
Ｎ−ジエチルトルアミドが広く用いられている。 ま
た、ｐ−メンタン−３，８−ジオールにも強い忌避効果
があることが知られている（特開昭６０−１９９８０４
号公報）。しかしながら、このＮ，Ｎ−ジエチルトルア
ミドは特異な臭いを有していることやｐ−メンタン−
３，８−ジオールには持続性に欠けるなどの問題があ
る。このために新規な有害生物忌避剤の開発が望まれて
いた。本発明の目的は、優れた有害生物忌避効果を有
し、不快臭の無い有害生物忌避剤として有用な新規化合
物を提供することにある。BACKGROUND OF THE INVENTION In order to protect yourself from pests such as mosquitoes, N,
N-diethyltoluamide is widely used. It is also known that p-menthane-3,8-diol has a strong repellent effect (JP-A-60-199804).
No.). However, this N, N-diethyltoluamide has a peculiar odor and p-menthane-
3,8-diol has problems such as lack of sustainability. For this reason, development of a novel pest repellent has been desired. An object of the present invention is to provide a novel compound which has an excellent pest repellent effect and is useful as a pest repellent having no unpleasant odor.
【０００３】[0003]
【課題を解決するための手段】本発明者らは、上記事情
に鑑み有害生物忌避剤として強い効果を有し、かつ特異
な臭いを有しない新しい有害生物忌避剤を開発すべく鋭
意研究した結果、２−ヒドロキシメチル−メントールが
優れた有害生物忌避効果を有することを提案した（特開
平５−１６３１８３号公報）。更に、本発明者らは、研
究を継続した結果、新たに２位にヒドロキシメチル基を
持つ環状アルコール誘導体が優れた有害生物忌避効果を
有し、その効果の持続性にも優れることを見出した。即
ち、本発明は下記一般構造式で表される２−ヒドロキシ
メチル−シクロアルカノール誘導体に関する。In view of the above circumstances, the present inventors have conducted intensive studies to develop a new pest repellent which has a strong effect as a pest repellent and has no peculiar odor. And 2-hydroxymethyl-menthol have an excellent pest repellent effect (JP-A-5-163183). Furthermore, the present inventors have continued their research and found that a cyclic alcohol derivative having a new hydroxymethyl group at the 2-position has an excellent pest repellent effect and is also excellent in the persistence of the effect. . That is, the present invention relates to a 2-hydroxymethyl-cycloalkanol derivative represented by the following general structural formula.
【化４】 （但し、ｎ＝３から１０であり、炭素総数が０から１０
までの直鎖または分岐鎖状飽和炭化水素が、環状炭素原
子の水素原子と置換した誘導体を含む。）Embedded image (However, n = 3 to 10 and the total number of carbons is 0 to 10
And straight chain or branched saturated hydrocarbons up to and including hydrogen atoms of cyclic carbon atoms. )
【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−ヒドロキシメチル−シクロアルカノー
ル誘導体を製造する方法としては環状炭素原子に炭素総
数が０から１０までの直鎖または側鎖状飽和炭化水素が
付加したシクロアルカノンより既知の方法により得られ
る２−エトキシカルボニルシクロアルカノンを水素化ホ
ウ素リチウムを用いて還元することにより得ることがで
きる〔オーガニック シンセシス（Ｏｒｇａｎｉｃ Ｓ
ｙｎｔｈｅｓｉｓ）第４７巻、２０頁、１９６７年〕。Hereinafter, the configuration of the present invention will be described in detail. As a method for producing the 2-hydroxymethyl-cycloalkanol derivative of the present invention, a cycloalkanone obtained by adding a linear or side chain saturated hydrocarbon having 0 to 10 carbon atoms to a cyclic carbon atom by a known method is used. 2-ethoxycarbonylcycloalkanone can be obtained by reduction with lithium borohydride [Organic Synthesis (Organic S)
47), page 20, 1967].
【０００５】本合成方法により２−ヒドロキシメチル−
シクロアルカノール誘導体は臭いもほとんどない無色透
明色の油状物で得られる。 得られた２−ヒドロキシメ
チル−シクロアルカノール誘導体が蚊などの有害生物に
対し強い忌避効果に優れるという特徴を見出し本発明を
完成した。According to the present synthesis method, 2-hydroxymethyl-
The cycloalkanol derivative is obtained as a colorless and transparent oil having almost no odor. The present inventors have found that the obtained 2-hydroxymethyl-cycloalkanol derivative has an excellent repellent effect against pests such as mosquitoes, and have completed the present invention.
【０００６】本発明の２−ヒドロキシメチル−シクロア
ルカノール誘導体とは、２−ヒドロキシメチル−３−メ
チル−シクロペンタノール、２−ヒドロキシメチル−３
−エチル−シクロペンタノール、２−ヒドロキシメチル
−４−プロピル−シクロペンタノール、２−ヒドロキシ
メチル−４−イソプロピル−シクロペンタノール、２−
ヒドロキシメチル−４−メチル−シクロヘキサノール、
２−ヒドロキシメチル−５−メチル−シクロヘキサノー
ル、２−ヒドロキシメチル−６−メチル−シクロヘキサ
ノール、２−ヒドロキシメチル−４−エチル−シクロヘ
キサノール、２−ヒドロキシメチル−４−（ｔ−ブチ
ル）−シクロヘキサノール、２−ヒドロキシメチル−６
−（ｔ−ブチル）−シクロヘキサノール、２−ヒドロキ
シメチル−６−（ｓｅｃ−ブチル）−シクロヘキサノー
ル、２−ヒドロキシメチル−４−（ｔ−アミル）−シク
ロヘキサノール、２−ヒドロキシメチル−３，４−ジメ
チル−シクロヘキサノール、２−ヒドロキシメチル−
４，５−ジメチル−シクロヘキサノール、２−ヒドロキ
シメチル−３，３，５−トリメチル−シクロヘキサノー
ル、２−ヒドロキシメチル−３，５，５−トリメチル−
シクロヘキサノール、２−ヒドロキシメチル−シクロヘ
プタノール、２−ヒドロキシメチル−シクロオクタノー
ル、２−ヒドロキシメチル−２−エチル−シクロオクタ
ノール、２−ヒドロキシメチル−シクロドデカノール等
の環状炭素数が５から１２までの２−ヒドロキシメチル
−シクロアルカノール及びその環状炭素原子の水素原子
を炭素総数１から１０までの飽和の直鎖または分岐鎖状
アルキル基と単数以上置換した化合物を示す。The 2-hydroxymethyl-cycloalkanol derivatives of the present invention are 2-hydroxymethyl-3-methyl-cyclopentanol, 2-hydroxymethyl-3
-Ethyl-cyclopentanol, 2-hydroxymethyl-4-propyl-cyclopentanol, 2-hydroxymethyl-4-isopropyl-cyclopentanol, 2-
Hydroxymethyl-4-methyl-cyclohexanol,
2-hydroxymethyl-5-methyl-cyclohexanol, 2-hydroxymethyl-6-methyl-cyclohexanol, 2-hydroxymethyl-4-ethyl-cyclohexanol, 2-hydroxymethyl-4- (t-butyl) -cyclo Hexanol, 2-hydroxymethyl-6
-(T-butyl) -cyclohexanol, 2-hydroxymethyl-6- (sec-butyl) -cyclohexanol, 2-hydroxymethyl-4- (t-amyl) -cyclohexanol, 2-hydroxymethyl-3,4 -Dimethyl-cyclohexanol, 2-hydroxymethyl-
4,5-dimethyl-cyclohexanol, 2-hydroxymethyl-3,3,5-trimethyl-cyclohexanol, 2-hydroxymethyl-3,5,5-trimethyl-
Cyclic carbon number of 5 to 12 such as cyclohexanol, 2-hydroxymethyl-cycloheptanol, 2-hydroxymethyl-cyclooctanol, 2-hydroxymethyl-2-ethyl-cyclooctanol, 2-hydroxymethyl-cyclododecanol And a compound in which a hydrogen atom of a cyclic carbon atom thereof is substituted by one or more saturated linear or branched alkyl groups having 1 to 10 carbon atoms.
【０００７】本発明の化合物を有効成分として、通常用
いられるところの化粧料、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。本発明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％から９０％であり、特に３
％から２０％が好ましい。[0007] By mixing the compound of the present invention as an active ingredient into a base (base) of a commonly used cosmetic or pharmaceutical, pest repellents of various dosage forms can be obtained. The content of the compound of the present invention varies depending on the form of the preparation, the method of use, and other conditions, but is generally from 0.1% to 90%, especially from 3%.
% To 20% is preferred.
【０００８】本発明の化合物は、ヒトスジシマカ等の
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 compounds of the present invention are used for mosquitoes such as Aedes albopictus and pests such as millipedes, armyworms and slugs.
【０００９】[0009]
【実施例】以下、実施例をあげて本発明をさらに具体的
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 below more specifically with reference to examples. In addition,% display in the following means% by weight unless otherwise specified.
【００１０】実施例１ ２０ｇの２−エトキシカルボニル−４−（ｔ−ブチル）
−シクロヘキサノンを２０ｍｌのテトラヒドロフランに
溶解した。２ｇの水素化ホウ素リチウムを８０ｍｌのテ
トラヒドロフランに分散した溶液を先の２−エトキシカ
ルボニル−４−（ｔ−ブチル）−シクロヘキサノン溶液
に氷冷攪拌下に滴下し４時間攪拌を続けた。 ５０ｍｌ
の酢酸エチルと１００ｍｌの蒸留水を加えた後、１０％
硫酸水溶液を反応溶液がｐＨ２になるまで添加した。
反応溶液を５０ｍｌのジエチルエーテルを用いて抽出を
２度行った。Example 1 20 g of 2-ethoxycarbonyl-4- (t-butyl)
-Cyclohexanone was dissolved in 20 ml of tetrahydrofuran. A solution in which 2 g of lithium borohydride was dispersed in 80 ml of tetrahydrofuran was added dropwise to the above 2-ethoxycarbonyl-4- (t-butyl) -cyclohexanone solution under ice-cooling and stirring, and stirring was continued for 4 hours. 50 ml
Of ethyl acetate and 100 ml of distilled water
An aqueous sulfuric acid solution was added until the reaction solution reached pH2.
The reaction solution was extracted twice using 50 ml of diethyl ether.
【００１１】ジエチルエーテル層を無水硫酸ナトリウム
にて乾燥後、ジエチルエーテルを除去することにより、
２−ヒドロキシメチル−４−（ｔ−ブチル）−シクロヘ
キサノールの粗反応生成物を得た。 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 ク
ロロホルム／メタノール＝９７／３）にて精製すること
により無色油状物として１５．３ｇ（収率９３％）の２
−ヒドロキシメチル−４−（ｔ−ブチル）−シクロヘキ
サノールを得た。 ＩＲ測定において３３７０ｃｍ-1に
強い水酸基の吸収とマススペクトル測定において〔親ピ
ーク（Ｍ）−１８（Ｈ2Ｏ）〕を認めた。また、ＴＭＳ
化後のマススペクトル測定において３３０（Ｍ＋２ＴＭ
Ｓ）を確認した。元素分析においてはＣ＝７０．７８
％、Ｈ＝１１．９３％の実測値（Ｃ，Ｈの理論値はＣ＝
７０．９２％、Ｈ＝１１．９０％）を得たことから確認
した。After drying the diethyl ether layer with anhydrous sodium sulfate, the diethyl ether is removed to obtain
A crude reaction product of 2-hydroxymethyl-4- (t-butyl) -cyclohexanol was obtained. The crude reaction product was purified by silica gel column chromatography (developing solvent: chloroform / methanol = 97/3) to give 15.3 g (yield 93%) of 2 as a colorless oil.
-Hydroxymethyl-4- (t-butyl) -cyclohexanol was obtained. In the IR measurement, absorption of a strong hydroxyl group at 3370 cm -1 and [parent peak (M) -18 (H 2 O)] were recognized in the mass spectrum measurement. Also, TMS
330 (M + 2TM)
S) was confirmed. C = 70.78 in elemental analysis
%, H = 11.93% actual measurement value (theoretical values of C and H are C =
70.92%, H = 11.90%).
【００１２】実施例２ 実施例１で用いた２０ｇの２−エトキシカルボニル−４
−（ｔ−ブチル）−シクロヘキサノンを２０ｇの２−エ
トキシカルボニル−シクロオクタノンに変え、同様の処
理を行い、無色油状物として１４．５ｇ（収率９１％）
の２−ヒドロキシメチル−シクロオクタノールを得た。
構造確認は、実施例１と同様にマススペクトル測定を行
なった結果、構造を支持する結果を得た。また元素分析
においてはＣ＝６７．９６％、Ｈ＝１１．５８％の実測
値（Ｃ，Ｈの理論値はＣ＝６８．３１％、Ｈ＝１１．４
７％）を得たことから確認した。Example 2 20 g of 2-ethoxycarbonyl-4 used in Example 1
-(T-Butyl) -cyclohexanone was changed to 20 g of 2-ethoxycarbonyl-cyclooctanone, and the same treatment was carried out to obtain 14.5 g of a colorless oil (yield: 91%).
Of 2-hydroxymethyl-cyclooctanol was obtained.
The structure was confirmed by measuring the mass spectrum in the same manner as in Example 1. As a result, a result supporting the structure was obtained. In elemental analysis, C = 67.96% and H = 11.58% were measured (theoretical values of C and H were C = 68.31% and H = 11.4).
7%).
【００１３】実施例３ 実施例１で用いた２０ｇの２−エトキシカルボニル−４
−（ｔ−ブチル）−シクロヘキサノンを２０ｇの２−エ
トキシカルボニル−４−エチル−シクロペンタノンに変
え、同様の処理を行い、無色油状物として１３．６ｇ
（収率８７％）の２−ヒドロキシメチル−４−エチル−
シクロペンタノールを得た。構造確認は、実施例１と同
様にマススペクトル測定を行なった結果、構造を支持す
る結果を得た。また元素分析においてはＣ＝６６．３３
％、Ｈ＝１１．４１％の実測値（Ｃ，Ｈの理論値はＣ＝
６６．６３％、Ｈ＝１１．１８％）を得たことから確認
した。Example 3 20 g of 2-ethoxycarbonyl-4 used in Example 1
-(T-Butyl) -cyclohexanone was changed to 20 g of 2-ethoxycarbonyl-4-ethyl-cyclopentanone, and the same treatment was carried out to obtain 13.6 g of a colorless oil.
(87% yield) of 2-hydroxymethyl-4-ethyl-
Cyclopentanol was obtained. The structure was confirmed by measuring the mass spectrum in the same manner as in Example 1. As a result, a result supporting the structure was obtained. In elemental analysis, C = 66.33.
%, H = 11.41% measured value (theoretical values of C and H are C =
(66.63%, H = 11.18%).
【００１４】実施例４ 実施例１で用いた２０ｇの２−エトキシカルボニル−４
−（ｔ−ブチル）−シクロヘキサノンを１５ｇの２−エ
トキシカルボニル−３，４−ジメチル−シクロヘキサノ
ンに変え、同様の処理を行い、無色油状物として９．３
ｇ（収率７８％）の２−ヒドロキシメチル−３，４−ジ
メチル−シクロヘキサノールを得た。構造確認は、実施
例１と同様にマススペクトル測定を行った結果、構造を
支持する結果を得た。また元素分析においてはＣ＝６
８．１０％、Ｈ＝１１．６４％実測値（Ｃ，Ｈの理論値
はＣ＝６８．３１％、Ｈ＝１１．４７％）を得たことか
ら確認した。Example 4 20 g of 2-ethoxycarbonyl-4 used in Example 1
-(T-Butyl) -cyclohexanone was changed to 15 g of 2-ethoxycarbonyl-3,4-dimethyl-cyclohexanone, and the same treatment was carried out to obtain 9.3 as a colorless oil.
g (yield 78%) of 2-hydroxymethyl-3,4-dimethyl-cyclohexanol was obtained. The structure was confirmed by performing mass spectrum measurement in the same manner as in Example 1. As a result, a result supporting the structure was obtained. In elemental analysis, C = 6
It was confirmed from the fact that 8.10% and H = 11.64% were actually measured (theoretical values of C and H were C = 68.31% and H = 11.47%).
【００１５】実施例５ 実施例１で用いた２０ｇの２−エトキシカルボニル−４
−（ｔ−ブチル）−シクロヘキサノンを２０ｇの２−エ
トキシカルボニル−４−イソプロピル−６−メチル−シ
クロヘキサノンに変え、同様の処理を行い、無色油状物
として１３．５ｇ（収率８２％）の２−ヒドロキシメチ
ル−４−イソプロピル−６−メチル−シクロヘキサノー
ルを得た。構造確認は、実施例１と同様にマススペクト
ル測定を行なった結果、構造を支持する結果を得た。ま
た元素分析においてはＣ＝７０．８６％、Ｈ＝１２．０
５％の実測値（Ｃ，Ｈの理論値はＣ＝７０．９２％、Ｈ
＝１１．９０％）を得たことから確認した。Example 5 20 g of 2-ethoxycarbonyl-4 used in Example 1
-(T-Butyl) -cyclohexanone was changed to 20 g of 2-ethoxycarbonyl-4-isopropyl-6-methyl-cyclohexanone, and the same treatment was carried out. Hydroxymethyl-4-isopropyl-6-methyl-cyclohexanol was obtained. The structure was confirmed by measuring the mass spectrum in the same manner as in Example 1. As a result, a result supporting the structure was obtained. In elemental analysis, C = 70.86% and H = 12.0
5% actual measurement (theoretical values of C and H are C = 70.92%, H
= 11.90%).
【００１６】以下に本発明の応用例を示す。 応用例１から４及び比較例１（リペルローション） 下記表１の処方に従って、応用例１から４及び比較例１
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。なお、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。An application example of the present invention will be described below. Application Examples 1 to 4 and Comparative Example 1 (Repel Lotion) Application Examples 1 to 4 and Comparative Example 1 according to the formulation in Table 1 below.
Was prepared and the following pest repellent test was carried out. In addition, N, N-diethyltoluamide has been conventionally used as a pest repellent.
【００１７】[0017]
【表１】 [Table 1]
【００１８】有害生物忌避効果およびその効果持続性の
試験方法は下記の通りである。 （１）ヒトスジシマカ成虫に対する吸血忌避試験方法 ヒトスジシ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日経過したヒトスジシマカの成虫の雌
雄５０匹ずつが入った袋状（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、数１
から忌避率を算出した。 ［数１］ 忌避率＝［（Ｘ−Ｙ）／Ｘ］×１００（％） 但し 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The test methods for the pest repellent effect and the effect persistence thereof are as follows. (1) Test method of blood sucking repellent against adult Aedes albopictus In order to examine the repellent effect of Aedes albopictus against adults, the following test was conducted in a constant temperature room at room temperature of 30 ° C. and humidity of 70%. After applying 10 ml of each test sample to the left and right forearms, each arm is inserted for 15 minutes into a bag-shaped (20 cm × 15 cm) wire mesh containing 50 adult males and females of Aedes albopictus 5 to 7 days after eclosion. Gave the time. This operation was performed 30 minutes, 1 hour, 2 hours, 4 hours, and 6 hours later, and the number of blood sucking traces within the time of blood sucking was calculated.
The repellent rate was calculated from. [Equation 1] Repellent rate = [(XY) / X] × 100 (%) where X: Number of traces of blood sucking when test liquid is not applied Y: Number of traces of blood sucking when test liquid is applied
【００１９】（２）結果 前記応用例１から４及び比較例１について、前記ヒトス
ジシマカ成虫に対する吸血忌避試験を行い、応用例１か
ら４と比較例１を比較した。 その結果を表２に示し
た。 表２から明かなごとく、本発明の２−ヒドロキシ
メチル−４−（ｔ−ブチル）−シクロヘキサノール、２
−ヒドロキシメチル−シクロオクタノール、２−ヒドロ
キシメチル−４−エチル−シクロペンタノール及び２−
ヒドロキシメチル−４−イソプロピル−６−メチル−シ
クロヘキサノールは優れた有害生物忌避効果としかも優
れた持続性を有していた。(2) Results With respect to the above-mentioned applied examples 1 to 4 and comparative example 1, a blood sucking repellent test against the adult Aedes albopictus was performed, and applied examples 1 to 4 and comparative example 1 were compared. The results are shown in Table 2. As is clear from Table 2, the 2-hydroxymethyl-4- (t-butyl) -cyclohexanol of the present invention, 2
-Hydroxymethyl-cyclooctanol, 2-hydroxymethyl-4-ethyl-cyclopentanol and 2-
Hydroxymethyl-4-isopropyl-6-methyl-cyclohexanol had an excellent pest repellent effect and excellent persistence.
【００２０】 [0020]
【００２１】[0021]
【発明の効果】以上記載のごとく、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新規化合物であ
る２−ヒドロキシメチル−シクロアルカノール誘導体を
提供できる。As described above, the present invention can provide a 2-hydroxymethyl-cycloalkanol derivative which is a novel compound having an excellent effect and sustainability as a pest repellent.
フロントページの続き (56)参考文献 特開 昭48−98012（ＪＰ，Ａ) 特開 平３−279337（ＪＰ，Ａ) 特開 昭63−39590（ＪＰ，Ａ) 特開 昭59−163365（ＪＰ，Ａ) 特開 平５−140016（ＪＰ，Ａ) 特開 平５−163182（ＪＰ，Ａ) 特開 平５−163183（ＪＰ，Ａ) Ｈｉｌｌ，Ｒ．Ｋ．，ｅｔ．ａ ｌ．，”Ａｂｓｏｌｕｔｅ ｃｏｎｆｉ ｇｕｒａｔｉｏｎ ｏｆ ｓａｒｋｏｍ ｙｃｉｎ．”Ｊ．Ｏｒｇ．Ｃｈｅｍ．, 32（７），（1967）ｐ．2330−ｐ．2335 Ｕｔｉｄａ，Ａｋｉｒａ．，ｅｔ．ａ ｌ．，”Ｐｒｉｎｓ ｒｅａｃｔｉｏｎ ｏｆ ｃｙｃｌｏｏｃｔｅｎｅ ａｎ ｄ ｃｙｃｌｏｄｏｄｅｃｅｎｅ．”Ｂ ｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．, 41（８），（1973）ｐ．2512−ｐ．2515 Ｄａｕｂｅｎ，Ｗ．Ｇ．，ｅｔ．ａ ｌ．，”Ｐｈｏｔｏｉｓｏｍｅｒｉｚａ ｔｉｏｎｓ ｏｆ ｃｉｓ− ａｎｄ ｔｒａｎｓ−３− ｍｅｔｈｙｌｅｎｅ ｃｙｃｌｏｄｅｃｅｎｅ．”Ｊ．Ａｍｅ ｒ．Ｃｈｅｍ．Ｓｏｃ．，92（25）, （1970）ｐ．7408−ｐ．7412 Ｃｈｅｍ．Ａｂｓｔｒ．，Ｖｏｌ．58 Ｎｏ．10−11（1963）抄録番号第 10097ｃ，Ｊ．Ｓｉｃｈｅｒ，ｅｒ．ａ ｌ．，”Ｓｔｅｒｅｏｃｈｅｍｉｃａｌ ｓｔｕｄｉｅｓ．ＸＸＩＩ．Ｂｒｏｍ ｉｎｅ ａｄｄｉｔｉｏｎ ｔｏ ｍｅ ｄｉｕｍ ｒｉｎｇ ｃｙｃｌｏｏｌｅ ｆｉｎｓ：ａ ｔｒａｎｓａｎｎｕｌａ ｒ ｒｅａｃｔｉｏｎ．”Ｃｏｌｌｅｃ ｔｉｏｎ Ｃｚｅｃｈ．Ｃｈｅｍ．Ｃｏ ｍｍｕｎ．27，（1962）ｐ．1927−ｐ. 1938 (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 35/02 - 35/205 A01N 31/06 A61K 7/40 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)Continuation of the front page (56) References JP-A-48-9802 (JP, A) JP-A-3-279337 (JP, A) JP-A-63-39590 (JP, A) JP-A-59-163365 (JP) JP-A-5-140016 (JP, A) JP-A-5-163182 (JP, A) JP-A-5-163183 (JP, A) Hill, R.A. K. , Et. a l. , "Absolute configuration of Sarcomycin." Org. Chem. , 32 (7), (1967) p. 2330-p. 2335 Utida, Akira. , Et. a l. , "Prins reaction of cyclooctene and cyclododecene." Chem. Soc. Jpn. , 41 (8), (1973) p. 2512-p. 2515 Dauben, W.C. G. FIG. , Et. a l. , "Photoisomerizatios of cis- and trans-3- methylene cyclodecene." Amer r. Chem. Soc. , 92 (25), (1970) p. 7408-p. 7412 Chem. Abstr. , Vol. 58 No. 10-11 (1963) Abstract No. 10097c, J. Am. Sicher, er. a l. , "Stereochemical studies. XXII. Bromine addition to medium ring cyclofins fins: a transannula r reaction." Collection Czech. Chem. Commun. 27, (1962) p. 1927-p. 1938 (58) Fields investigated (Int. Cl. 7 , DB name) C07C 35/02-35/205 A01N 31/06 A61K 7/40 CA (STN) REGISTRY (STN)
Claims (3)
クロペンタノール。1. 2-Hydroxymethyl-4-ethyl-cyclopentanol.
ル−６−メチル−シクロヘキサノール。2. 2-Hydroxymethyl-4-isopropyl-6-methyl-cyclohexanol.
シメチル−シクロアルカノール誘導体からなる有害生物
忌避剤。 【化１】 （上記式中、ｎ＝３から１０であり、炭素総数が０から
１０までの直鎖または分岐鎖状飽和炭化水素が、環状炭
素原子の水素原子と置換した誘導体を含む。但し、下記
化２又は化３で示される化合物および２−ヒドロキシメ
チル−メントールを除く。） 【化２】 （但し、Ｒ＝Ｃ1からＣ12の直鎖又は分岐鎖状飽和炭化
水素である。） 【化３】 （但し、Ｒ1はＣ1からＣ12の直鎖又は分岐鎖状飽和炭化
水素である。）3. A pest repellent comprising a 2-hydroxymethyl-cycloalkanol derivative represented by the following general structural formula. Embedded image (In the above formula, n = 3 to 10 and a derivative in which a linear or branched saturated hydrocarbon having a total carbon number of 0 to 10 is substituted with a hydrogen atom of a cyclic carbon atom. Or the compound of formula 3 and 2-hydroxymethyl-menthol are excluded.) (Where R = C 1 to C 12 linear or branched saturated hydrocarbon). (However, R 1 is a C 1 to C 12 linear or branched saturated hydrocarbon.)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04808892A JP3156867B2 (en) | 1992-02-03 | 1992-02-03 | 2-hydroxymethyl-cycloalkanol derivative |
| 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 |
|---|---|---|---|
| JP04808892A JP3156867B2 (en) | 1992-02-03 | 1992-02-03 | 2-hydroxymethyl-cycloalkanol derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05213802A JPH05213802A (en) | 1993-08-24 |
| JP3156867B2 true JP3156867B2 (en) | 2001-04-16 |
Family
ID=12793572
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04808892A Expired - Lifetime JP3156867B2 (en) | 1991-09-02 | 1992-02-03 | 2-hydroxymethyl-cycloalkanol derivative |
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| Country | Link |
|---|---|
| JP (1) | JP3156867B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6372804B1 (en) * | 1991-09-02 | 2002-04-16 | Kanebo, Ltd. | Noxious-insect repellent |
| US6130255A (en) * | 1993-10-22 | 2000-10-10 | Ikemoto; Takeshi | Noxious-insect repellent |
| US9314029B2 (en) * | 2012-05-02 | 2016-04-19 | Bedoukain Research, Inc. | Control and repellency of mosquitoes |
| US9924718B2 (en) * | 2013-04-30 | 2018-03-27 | Bedoukian Research, Inc. | Control and repellency of biting flies, house flies, ticks, ants, fleas, biting midges, cockroaches, spiders and stink bugs |
-
1992
- 1992-02-03 JP JP04808892A patent/JP3156867B2/en not_active Expired - Lifetime
Non-Patent Citations (4)
| Title |
|---|
| Ｃｈｅｍ．Ａｂｓｔｒ．，Ｖｏｌ．５８ Ｎｏ．１０−１１（１９６３）抄録番号第１００９７ｃ，Ｊ．Ｓｉｃｈｅｒ，ｅｒ．ａｌ．，"Ｓｔｅｒｅｏｃｈｅｍｉｃａｌ ｓｔｕｄｉｅｓ．ＸＸＩＩ．Ｂｒｏｍｉｎｅ ａｄｄｉｔｉｏｎ ｔｏ ｍｅｄｉｕｍ ｒｉｎｇ ｃｙｃｌｏｏｌｅｆｉｎｓ：ａ ｔｒａｎｓａｎｎｕｌａｒ ｒｅａｃｔｉｏｎ．"Ｃｏｌｌｅｃｔｉｏｎ Ｃｚｅｃｈ．Ｃｈｅｍ．Ｃｏｍｍｕｎ．２７，（１９６２）ｐ．１９２７−ｐ．１９３８ |
| Ｄａｕｂｅｎ，Ｗ．Ｇ．，ｅｔ．ａｌ．，"Ｐｈｏｔｏｉｓｏｍｅｒｉｚａｔｉｏｎｓ ｏｆ ｃｉｓ− ａｎｄ ｔｒａｎｓ−３− ｍｅｔｈｙｌｅｎｅｃｙｃｌｏｄｅｃｅｎｅ．"Ｊ．Ａｍｅｒ．Ｃｈｅｍ．Ｓｏｃ．，９２（２５），（１９７０）ｐ．７４０８−ｐ．７４１２ |
| Ｈｉｌｌ，Ｒ．Ｋ．，ｅｔ．ａｌ．，"Ａｂｓｏｌｕｔｅ ｃｏｎｆｉｇｕｒａｔｉｏｎ ｏｆ ｓａｒｋｏｍｙｃｉｎ．"Ｊ．Ｏｒｇ．Ｃｈｅｍ．，３２（７），（１９６７）ｐ．２３３０−ｐ．２３３５ |
| Ｕｔｉｄａ，Ａｋｉｒａ．，ｅｔ．ａｌ．，"Ｐｒｉｎｓ ｒｅａｃｔｉｏｎ ｏｆ ｃｙｃｌｏｏｃｔｅｎｅ ａｎｄ ｃｙｃｌｏｄｏｄｅｃｅｎｅ．"Ｂｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．，４１（８），（１９７３）ｐ．２５１２−ｐ．２５１５ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05213802A (en) | 1993-08-24 |
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