JPH0267258A - Amide compound - Google Patents

Amide compound

Info

Publication number
JPH0267258A
JPH0267258A JP21718788A JP21718788A JPH0267258A JP H0267258 A JPH0267258 A JP H0267258A JP 21718788 A JP21718788 A JP 21718788A JP 21718788 A JP21718788 A JP 21718788A JP H0267258 A JPH0267258 A JP H0267258A
Authority
JP
Japan
Prior art keywords
group
formula
compound shown
carbon atoms
base
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.)
Pending
Application number
JP21718788A
Other languages
Japanese (ja)
Inventor
Hiroko Kishino
岸野 浩子
Masahiro Takahashi
高橋 政弘
Yoshinori Shono
庄野 美徳
Noritada Matsuo
憲忠 松尾
Masakazu Miyakado
宮門 正和
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to JP21718788A priority Critical patent/JPH0267258A/en
Publication of JPH0267258A publication Critical patent/JPH0267258A/en
Pending legal-status Critical Current

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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:A compound shown by formula I (R is 1-10C saturated hydrocarbon group, 1-10C haloalkyl, 2-10C alkoxyalkyl, 2-10C alkenyl or 2-10C alkynyl) EXAMPLE:trans-N-Normal-propyl-8-hexenamide. USE:A repellent against insect pests having repelling effects especially on mosquitoes, cockroaches, acarids, etc., and higher repelling effects on a wide range of various insect pests than those of N,N-diethyl-8-toluamide. PREPARATION:A compound shown by formula II is reacted with an amine shown by formula III in a solventless state or in a solvent to give a compound shown by formula I. In the reaction, 1-2mol amine shown by formula III and optionally 1-4mol base are used based on 1mol compound shown by formula I. Pyridine, triethylamine, etc., may be cited as the base.

Description

【発明の詳細な説明】 〈産業上の利用分舒〉 本発明は、害虫忌避剤として有用な新規なアミド化合物
に関する。
DETAILED DESCRIPTION OF THE INVENTION <Industrial Application> The present invention relates to a novel amide compound useful as an insect repellent.

〈従来の技術〉 従来、蚊、ブユ等の吸血害虫やその他の衛生害虫に対す
る忌避剤として、N、N−ジエチル−8−トルア鳳ド(
Deet)が広く利用されている。
<Prior art> Conventionally, N,N-diethyl-8-tolua (
Deet) is widely used.

〈発明が解決しようとする課題〉 しかしながら、Deetは対象害虫穏が限られ、かつ残
効性が短い等必ずしも満足すべきものではない。
<Problems to be Solved by the Invention> However, Deet is not necessarily satisfactory, as its effectiveness against target pests is limited and its residual effect is short.

〈課題を解決するための手段〉 本発明者らは、このような状況に鑑み、鋭意検討した結
果、下記−数式(1)で示されるアミド化合物が、De
et以上の高い活性と幅広い種々の害虫に対する忌避効
力とを有することを見出し、本発明に至った。
<Means for Solving the Problems> In view of the above circumstances, the present inventors have made extensive studies and found that the amide compound represented by the following formula (1) is De
It was discovered that it has a higher activity than E. et al. and a repellent effect against a wide variety of pests, leading to the present invention.

すなわち、本発明は害虫忌避剤として有用な一般式(I
) (式中、Rは炭素数1〜lOの飽和炭化水素基、炭素数
1〜10のハロアルキル基、全炭素数が2〜10のアル
コキシアルキル基、炭素数2〜10のアルケニル基また
は炭素数2〜10のアルキニル基を表わす。) で示されるアミド化合物(以下、本発明化合物と称する
。)を提供するものである。
That is, the present invention provides compounds of the general formula (I) useful as pest repellents.
) (wherein R is a saturated hydrocarbon group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group having 2 to 10 carbon atoms in total, an alkenyl group having 2 to 10 carbon atoms, or a carbon number represents an alkynyl group of 2 to 10) (hereinafter referred to as the compound of the present invention).

本発明化合物が特書ζ有効な害虫としては、たとえば蚊
、ゴキブリ、ダニ等をあげることができる。
Examples of pests against which the compounds of the present invention are particularly effective include mosquitoes, cockroaches, and mites.

一般式(1)で示される本発明化合物のRの定義におい
て、炭素数1〜10の飽和炭化水素基とは、たとえば炭
素数1〜10の直鎖状もしくは分岐状アルキル基、炭素
数8〜10のシクロアルキル基、全炭素数が4〜10の
フルキルシクロアルキル基、全炭素数が4〜lOの(シ
クロアルキル)アルキル基、全炭素数が5〜10の(ア
ルキルシクロアルキル)アルキル基等ヲ意味し、具体例
としては、メチル基、エチル基、n−プロピル基、イソ
プロピル基、n−ブチル基、2−メチルプロピル基、t
ert−ブチル基、n−ペンチル基、1,2−ジメチル
プロピル基、1−メチルブチル基、2−メチルブチル基
、8−メチルブチル基、n−ヘキシル基、1−メチルペ
ンチル基、2−メチルペンチル基、8−メチルペンチル
基、n−へブチル基、シクロプロピル基、シクロブチル
基、シクロペンチル基、シクロヘキシル基、シクロヘプ
チル基、シクロヘキシルメチル基、(4−メチルシクロ
ヘキシル)メチル基、シクロヘキシルエチル基、シクロ
ペンチルメチル基、シクロプロピルエチル基等があげら
れる。また、炭素数1〜10のハロアルキル基または全
炭素数が2〜10のアルコキシアルキル基としては、た
とえば2−ブロモエチル基、2,6−ジクロロペンチル
基、2−メトキシエチル基、8−エトキシブチル基等が
あげられる。さらに、炭素数2〜10のアルケニル基ま
たは炭素数2〜10のアルキニル基としては、たとえば
2−プロペニル基、2−プロピニル基等があげられるが
、もちろん本発明はこれらに限定されるものではない。
In the definition of R in the compound of the present invention represented by general formula (1), a saturated hydrocarbon group having 1 to 10 carbon atoms is, for example, a linear or branched alkyl group having 1 to 10 carbon atoms, or a saturated hydrocarbon group having 1 to 10 carbon atoms; 10 cycloalkyl group, a furkylcycloalkyl group having a total carbon number of 4 to 10, a (cycloalkyl)alkyl group having a total carbon number of 4 to 1O, an (alkylcycloalkyl)alkyl group having a total carbon number of 5 to 10. Specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, 2-methylpropyl group, t
ert-butyl group, n-pentyl group, 1,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 8-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 8-methylpentyl group, n-hebutyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclohexylmethyl group, (4-methylcyclohexyl)methyl group, cyclohexylethyl group, cyclopentylmethyl group, Examples include cyclopropylethyl group. In addition, examples of the haloalkyl group having 1 to 10 carbon atoms or the alkoxyalkyl group having 2 to 10 total carbon atoms include 2-bromoethyl group, 2,6-dichloropentyl group, 2-methoxyethyl group, and 8-ethoxybutyl group. etc. can be mentioned. Further, examples of the alkenyl group having 2 to 10 carbon atoms or the alkynyl group having 2 to 10 carbon atoms include 2-propenyl group, 2-propynyl group, etc., but of course the present invention is not limited to these. .

本発明化合物は、文献未記載の新規化合物であり一これ
らは下記反応式によって合成することができる。
The compounds of the present invention are novel compounds that have not been described in any literature, and can be synthesized by the following reaction formula.

(カ (I) (上記式中、Rは前記と同じ意味を表わす。)すなわち
、式(6)で示される化合物と一般式(2)で示される
アミンとを、無溶媒または溶媒中で反応させることによ
り、一般式(I)で示される本発明化合物を得ることが
できる。反応を行なうに際し、必要に応じて塩基を加え
ることにより、迅速に反応させることもできる。
(I) (In the above formula, R represents the same meaning as above.) That is, the compound represented by formula (6) and the amine represented by general formula (2) are reacted without a solvent or in a solvent. By doing so, the compound of the present invention represented by the general formula (I) can be obtained. When carrying out the reaction, the reaction can be carried out quickly by adding a base as necessary.

反応に供する試剤の量は、通常式(6)で示される化合
物1モルに対して、一般式(ロ)で示されるアミンは1
〜2モル、塩基は1〜4モルである。
The amount of the reagent used in the reaction is usually 1 mole of the compound represented by formula (6), and 1 mole of the amine represented by general formula (b).
~2 mol, base 1-4 mol.

反応温度は通常0〜120℃、好ましくは0〜40℃で
ある。反応時間は通常0.1〜24時間であるが、好ま
しくは0.5〜12時間である。
The reaction temperature is usually 0 to 120°C, preferably 0 to 40°C. The reaction time is usually 0.1 to 24 hours, preferably 0.5 to 12 hours.

使用される溶媒としては、たとえばベンゼン、トルエン
、キシレン等の芳香族炭化水素類、ジクロルメタン、ジ
クロルエタン等のハロゲン化炭化水素類、ジオキサン、
テトラヒドロフラン等のエーテル類または水あるいは水
を含んだ混合溶媒等があげられる。また、塩基としては
、たとえばピリジン、トリエチルアミン、エチルジイソ
プロピルアミン、水酸化ナトリウム、水酸化カリウム、
炭酸ナトリウム、炭酸カリウム等があげられる。
Examples of solvents used include aromatic hydrocarbons such as benzene, toluene, and xylene, halogenated hydrocarbons such as dichloromethane and dichloroethane, dioxane,
Examples include ethers such as tetrahydrofuran, water, and mixed solvents containing water. In addition, examples of the base include pyridine, triethylamine, ethyldiisopropylamine, sodium hydroxide, potassium hydroxide,
Examples include sodium carbonate and potassium carbonate.

〈実施例〉 以下、実施例および参考例をあげ、本発明をさらに詳し
く説明するが、本発明はこれらに限定されるものではな
い。
<Examples> Hereinafter, the present invention will be explained in more detail with reference to Examples and Reference Examples, but the present invention is not limited thereto.

実施例1 ノルマル−プロピルアミン2.95Fにトルエン15m
jを仕込み、水冷下にトランス−8−ヘキセン酸クロリ
ド8.8Fを徐々に滴下した。氷冷下で1時間攪拌し、
反応液を水にあけて、酢酸エチルで抽出した。酢酸エチ
ル層を水、食塩水で順次洗浄し、硫酸マグネシウムで乾
燥した。
Example 1 Toluene 15m in normal-propylamine 2.95F
8.8F of trans-8-hexenoyl chloride was gradually added dropwise to the mixture while cooling with water. Stir for 1 hour under ice cooling,
The reaction solution was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over magnesium sulfate.

溶媒を留去した後、シリカゲルカラムクロマトグラフィ
ーに付しく展開溶媒n−ヘキサン/酢酸エチル=1/1
)、8.45fC収率89%)のトランス−N−ノルマ
ル−プロピル−8−ヘキセナミドを無色油状物として得
た。
After distilling off the solvent, it was subjected to silica gel column chromatography using a developing solvent of n-hexane/ethyl acetate = 1/1.
), 8.45 fC (yield: 89%) of trans-N-n-propyl-8-hexenamide was obtained as a colorless oil.

nも1・’  1.4785 NMR(δ値CDCJ、) 0.75−1.25(m、6H)  1.8〜2.4(
m、4H)2.90/−4,40(m、4H)  5.
45〜5.75(m、2H)5.81)〜6.85 (
br、 s IH)このようにして得られた本発明化合
物のいくつかを表1に示す。
n is also 1・' 1.4785 NMR (δ value CDCJ,) 0.75-1.25 (m, 6H) 1.8-2.4 (
m, 4H) 2.90/-4,40 (m, 4H) 5.
45-5.75 (m, 2H) 5.81)-6.85 (
br, s IH) Some of the compounds of the present invention thus obtained are shown in Table 1.

表 一般式 表2に記載の各供試化合物を7096エタノールで希釈
した所定濃度の溶液20μjを、脱毛したマウス背部の
皮膚(1,5X2m)に処理した(有効成分として2.
0fld相当)。マウスは処理部分のみが露出される様
に固定した。このマウスおよび薬剤無処理のマウスを、
ハマダラカのINである(Anophclea alb
imanus)の羽化後4〜6日令の雌成虫100頭が
入ったケージ(22x22x80cIR)中に入れ、5
分後に吸血のため集まった雌成虫数を観察した。実験は
処理J後、1時間後の計2回行なった。忌避率は下記式
により求めた。
20 µj of a solution of each test compound listed in Table 2 diluted with 7096 ethanol at a predetermined concentration was applied to the depilated skin of the back of a mouse (1.5 x 2 m) (2.
(equivalent to 0fld). The mouse was fixed so that only the treated area was exposed. This mouse and drug-free mice were
It is IN of Anopheles mosquito (Anophclea alb).
imanus) was placed in a cage (22 x 22 x 80 cIR) containing 100 female adults aged 4 to 6 days after emergence, and
After a few minutes, the number of female adults gathered for blood feeding was observed. The experiment was conducted twice, one after treatment J and one after 1 hour. The repellency rate was calculated using the following formula.

結果を表2に示す。The results are shown in Table 2.

〈発明の効果〉 本発明化合物は、特に蚊、ゴキブリ、ダニ等の害虫に対
する忌避効力を有する。
<Effects of the Invention> The compound of the present invention has a repellent effect particularly on pests such as mosquitoes, cockroaches, and mites.

Claims (1)

【特許請求の範囲】 一般式 ▲数式、化学式、表等があります▼ (式中、Rは炭素数1〜10の飽和炭化水素基、炭素数
1〜10のハロアルキル基、全炭素数が2〜10のアル
コキシアルキル基、炭素数2〜10のアルケニル基また
は炭素数2〜10のアルキニル基を表わす。) で示されるアミド化合物。
[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. 10 alkoxyalkyl group, an alkenyl group having 2 to 10 carbon atoms, or an alkynyl group having 2 to 10 carbon atoms.
JP21718788A 1988-08-30 1988-08-30 Amide compound Pending JPH0267258A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP21718788A JPH0267258A (en) 1988-08-30 1988-08-30 Amide compound

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP21718788A JPH0267258A (en) 1988-08-30 1988-08-30 Amide compound

Publications (1)

Publication Number Publication Date
JPH0267258A true JPH0267258A (en) 1990-03-07

Family

ID=16700228

Family Applications (1)

Application Number Title Priority Date Filing Date
JP21718788A Pending JPH0267258A (en) 1988-08-30 1988-08-30 Amide compound

Country Status (1)

Country Link
JP (1) JPH0267258A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5033728A (en) * 1989-02-13 1991-07-23 Konica Corporation Document feeder

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5033728A (en) * 1989-02-13 1991-07-23 Konica Corporation Document feeder

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