JPH024202B2

JPH024202B2 -

Info

Publication number: JPH024202B2
Application number: JP56169844A
Authority: JP
Inventors: Hiroshi Kimura; Masaru Tauchi; Isamu Nitsuta; Yoji Takahashi; Katsutoshi Sato
Original assignee: Mitsubishi Kasei Corp
Current assignee: Mitsubishi Chemical Corp
Priority date: 1981-10-23
Filing date: 1981-10-23
Publication date: 1990-01-26
Also published as: JPS5872504A

Description

[Detailed description of the invention]

本発明は新しい害虫忌避剤組成物及び害虫忌避
材に関する。従来よりゴキブリ等の各種衛生害虫を駆除する
方法としては、例えばピレスロイド系殺虫剤等の
殺虫剤を散布する方法や各種の捕虫器具等を用い
る方法が知られている。之等の方法は殺虫乃至捕
虫によつて害虫の殺滅を計り、該害虫による食害
や吸血等の被害をある程度防止できるものではあ
るが、例えば台所、畜舎、水屋、タンス等の家具
内又は人体、農作物等の動植物体への害虫の飛
来、接近、接触、侵入、汚染等を回避できるもの
ではなく、充分な駆除効果は奏し得ない。しかも
上記方法においては殺虫乃至捕虫後の害虫の処理
が必要となり、殊に家具内等へ侵入後に死ぬ害虫
の処理は困難であると共にこれはむしろ汚染源と
なる幣害がある。一方上記害虫の飛来、侵入等を
防止でき、勿論死虫の処理を何ら必要としない害
虫駆除方法として、害虫忌避剤を用いる方法が知
られており、近時上記方法に利用できる害虫忌避
作用を有する各種の物質が研究開発及び提案され
つつある。しかしながら上記提案された各種の物
質は、いずれも尚充分に満足できる害虫忌避効果
を発揮できるものではなく、わずかにＮ，Ｎ−ジ
エチル−メタ−トルアミドを始めとする数種の物
質が、スプレー、ローシヨン、クリーム等の形態
で蚊、ノミ、ナンキンムシ、サシバエ等の吸血害
虫に対する忌避剤として実用されているにすぎな
い。本発明者らは上記現状に鑑み、優れた害虫忌避
効果を発揮し、害虫の侵入等をほぼ確実に防止可
能な忌避剤を提供することを目的として種々研究
を重ねた。その結果下記一般式（）で表わされ
る特定の化合物が、上記目的に合致する害虫忌避
効果を発現できることを見い出した。本発明はこの新しい知見に基づいて完成された
ものである。即ち本発明は一般式（式中、Ｘ、Ｙは同じでも異なつてもよく水素
原子又はハロゲン原子を示す。Ｒは、水素原子、
炭素数３〜８のアルキル基、アルケニル基、アル
キニル基又はシクロアルキル基を示す。但し、Ｘ及びＹが共にハロゲン原子を示す場
合、Ｒは炭素数５〜８のアルキル基ではない。で表わされる化合物を有効成分として含有するこ
とを特徴とする害虫忌避剤組成物及び該組成物を
基材に保持させたことを特徴とする害虫忌避材に
係る。本発明の害虫忌避剤組成物は、その有効成分と
して上記一般式（）で表わされる特定のマレイ
ミド誘導体を含有することに基づいて、極めて優
れた害虫忌避効果を奏し得る。その忌避効果は、
ゴキブリ、ハエ、カ、アブ、ノミ、ナンキンムシ
等の衛生害虫乃至吸血害虫は勿論のこと、イガ、
コイガ等の衣料害虫、コクヌストモドキ、コクゾ
ウムシ等の貯穀害虫、更にはアリ、シロアリ及び
ナメクジ等に対しても強力なものである。従つて本発明の害虫忌避剤組成物は、これを家
庭内の玄関、台所、食堂等や畜舎、農園等ハウス
等の特定区域、タンス、食物収納庫、衣裳ケー
ス、人形ケース等の収納家具内及び人体、動物
体、植物体等に適用することによつて、之等の場
所への害虫の飛来、接近、接触、侵入等を確実に
防止し、また上記特定区域内等での害虫の棲息、
食害等及び動植物体の刺咬、吸血等、更には汚染
をも見事に回避できるのである。本発明害虫忌避剤組成物の有効成分であるマレ
イミド誘導体としては一般式（）に於けるＸ、
Ｙが水素原子、塩素原子、臭素原子、フツ素原
子、ヨウ素原子であり、Ｒが水素原子、炭素数３
〜８の直鎖又は分岐鎖を有するアルキル基、アル
ケニル基、アルキニル基又はシクロアルキル基で
ある化合物が挙げられる。具体的にはマレイミ
ド、Ｎ−（ｎ−、又はｉ−）プロピルマレイミド、
Ｎ−（ｎ−、イソ−、sec−又はtert−）ブチルマ
レイミド、Ｎ−（ｎ−、イソ−又はネオ−）ペン
チルマレイミド、Ｎ−ヘキシルマレイミド、Ｎ−
（１−又は２−メチル）ペンチルマレイミド、Ｎ
−ヘプチルマレイミド、Ｎ−オクチルマレイミ
ド、Ｎ−（２−エチルヘキシル）−マレイミド、Ｎ
−アリルマレイミド、Ｎ−メタリルマレイミド、
Ｎ−プロパルギルマレイミド、Ｎ−ブチニルマレ
イミド、Ｎ−シクロペンチルマレイミド、Ｎ−シ
クロヘキシルマレイミド、２−クロルマレイミ
ド、Ｎ−（ｎ−又はｉ−）プロピル−２−クロル
マレイミド、Ｎ−（ｎ−、ｉ−、sec−又はtert
−）ブチル−２−クロルマレイミド、Ｎ−（ｎ−、
ｉ−、neo−）ペンチル−２−クロルマレイミ
ド、Ｎ−（１−又は２−）メチルペンチル−２−
クロルマレイミド、Ｎ−ヘキシル−２−クロルマ
レイミド、Ｎ−ヘプチル−２−クロルマレイミ
ド、Ｎ−オクチル−２−クロルマレイミド、Ｎ−
（２−エチルヘキシル）−２−クロルマレイミド、
Ｎ−ノニル−２−クロルマレイミド、Ｎ−デシル
−２−クロルマレイミド、Ｎ−ウンデシル−２−
クロルマレイミド、Ｎ−ドデシル−２−クロルマ
レイミド、Ｎ−アリル−２−クロルマレイミド、
Ｎ−メタリル−２−クロルマレイミド、Ｎ−プロ
パルギル−２−クロルマレイミド、Ｎ−ブチニル
−２−クロルマレイミド、Ｎ−シクロペンチル−
２−クロルマレイミド、Ｎ−シクロヘキシル−２
−クロルマレイミド、２−ブロムマレイミド、Ｎ
−メチル−２−ブロムマレイミド、Ｎ−エチル−
２−ブロムマレイミド、Ｎ−（ｎ−又はｉ−）プ
ロピル−２−ブロムマレイミド、Ｎ−（ｎ−、ｉ
−、sec−又はtert−）ブチル−２−ブロムマレ
イミド、Ｎ−（ｎ−、ｉ−又はネオ−）ペンチル
−２−ブロムマレイミド、Ｎ−ヘキシル−２−ブ
ロムマレイミド、Ｎ−（１−又は２−）メチルペ
ンチル−２−ブロムマレイミド、Ｎ−ヘプチル−
２−ブロムマレイミド、Ｎ−オクチル−２−ブロ
ムマレイミド、Ｎ−（２−エチルヘキシル）−２−
ブロムマレイミド、Ｎ−アリル−２−ブロムマレ
イミド、Ｎ−メタリル−２−ブロムマレイミド、
Ｎ−プロパルギル−２−ブロムマレイミド、Ｎ−
ブチニル−２−ブロムマレイミド、Ｎ−シクロペ
ンチル−２−ブロムマレイミド、Ｎ−シクロヘキ
シル−２−ブロムマレイミド、２−ヨードマレイ
ミド、Ｎ−（ｎ−又はｉ−）プロピル−２−ヨー
ドマレイミド、Ｎ−（ｎ−、ｉ−、sec−又はtert
−）ブチル−２−ヨードマレイミド、Ｎ−（ｎ−、
ｉ−又はネオ−）ペンチル−２−ヨードマレイミ
ド、Ｎ−ヘキシル−２−ヨードマレイミド、Ｎ−
（１−又は２−）メチルペンチル−２−ヨードマ
レイミド、Ｎ−ヘプチル−２−ヨードマレイミ
ド、Ｎ−オクチル−２−ヨードマレイミド、Ｎ−
（２−エチルヘキシル）−２−ヨードマレイミド、
Ｎ−アリル−２−ヨードマレイミド、Ｎ−メタリ
ル−２−ヨードマレイミド、Ｎ−プロパルギル−
２−ヨードマレイミド、Ｎ−ブチニル−２−ヨー
ドマレイミド、Ｎ−シクロペンチル−２−ヨード
マレイミド、Ｎ−シクロヘキシル−２−ヨードマ
レイミド、２−フルオロマレイミド、Ｎ−（ｎ−
又はｉ−）プロピル−２−フルオロマレイミド、
Ｎ−（ｎ−、ｉ−、sec−又はtert−）ブチル−２
−フルオロマレイミド、Ｎ−（ｎ−、ｉ−又はネ
オ−）ペンチル−２−フルオロマレイミド、Ｎ−
ヘキシル−２−フルオロマレイミド、Ｎ−（１−
又は２−）メチルペンチル−２−フルオロマレイ
ミド、Ｎ−ヘプチル−２−フルオロマレイミド、
Ｎ−オクチル−２−フルオロマレイミド、Ｎ−
（２−エチルヘキシル）−２−フルオロマレイミ
ド、Ｎ−アリル−２−フルオロマレイミド、Ｎ−
メタリル−２−フルオロマレイミド、Ｎ−プロパ
ルギル−２−フルオロマレイミド、Ｎ−ブチニル
−２−フルオロマレイミド、Ｎ−シクロペンチル
−２−フルオロマレイミド、Ｎ−シクロヘキシル
−２−フルオロマレイミド、２，３−ジクロルマ
レイミド、Ｎ−（ｎ−又はｉ−）プロピル−２，
３−ジクロルマレイミド、Ｎ−（ｎ−、ｉ−、sec
−又はtert−）ブチル−２，３−ジクロルマレイ
ミド、Ｎ−アリル−２，３−ジクロルマレイミ
ド、Ｎ−メタリル−２，３−ジクロルマレイミ
ド、Ｎ−プロパルギル−２，３−ジクロルマレイ
ミド、Ｎ−ブチニル−２，３−ジクロルマレイミ
ド、Ｎ−シクロペンチル−２，３−ジクロルマレ
イミド、Ｎ−シクロヘキシル−２，３−ジクロル
マレイミド、２，３−ジブロムマレイミド、Ｎ−
（ｎ−又はｉ−）プロピル−２，３−ジブロムマ
レイミド、Ｎ−（ｎ−、ｉ−、sec−又はtert−）
ブチル−２，３−ジブロムマレイミド、Ｎ−アリ
ル−２，３−ジブロムマレイミド、Ｎ−メタリル
−２，３−ジブロムマレイミド、Ｎ−プロパルギ
ル−２，３−ジブロムマレイミド、Ｎ−ブチニル
−２，３−ジブロムマレイミド、Ｎ−シクロペン
チル−２，３−ジブロムマレイミド、Ｎ−シクロ
ヘキシル−２，３−ジブロムマレイミド、２，３
−ジフルオロマレイミド、Ｎ−（ｎ−又はｉ−）
プロピル−２，３−ジフルオロマレイミド、Ｎ−
（ｎ−、ｉ−、sec−又はtert−）ブチル−２，３
−ジフルオロマレイミド、Ｎ−アリル−２，３−
ジフルオロマレイミド、Ｎ−メタリル−２，３−
ジフルオロマレイミド、Ｎ−プロパルギル−２，
３−ジフルオロマレイミド、Ｎ−ブチニル−２，
３−ジフルオロマレイミド、Ｎ−シクロペンチル
−２，３−ジフルオロマレイミド、Ｎ−シクロヘ
キシル−２，３−ジフルオロマレイミド、２，３
−ジヨードマレイミド、Ｎ−（ｎ−又はｉ−）プ
ロピル−２，３−ジヨードマレイミド、Ｎ−（ｎ
−、ｉ−、sec−又はtert−）ブチル−２，３−
ジヨードマレイミド、Ｎ−アリル−２，３−ジヨ
ードマレイミド、Ｎ−メタリル−２，３−ジヨー
ドマレイミド、Ｎ−プロパルギル−２，３−ジヨ
ードマレイミド、Ｎ−ブチニル−２，３−ジヨー
ドマレイミド、Ｎ−シクロペンチル−２，３−ジ
ヨードマレイミド、Ｎ−シクロヘキシル−２，３
−ジヨードマレイミド、２−クロル−３−フルオ
ロマレイミド、Ｎ−（ｎ−又はｉ−）プロピル−
２−クロル−３−フルオロマレイミド、Ｎ−（ｎ
−、ｉ−、sec−又はtert−）ブチル−２−クロ
ル−３−フルオロマレイミド、Ｎ−アリル−２−
クロル−３−フルオロマレイミド、Ｎ−メタリル
−２−クロル−３−フルオロマレイミド、Ｎ−プ
ロパルギル−２−クロル−３−フルオロマレイミ
ド、Ｎ−ブチニル−２−クロル−３−フルオロマ
レイミド、２−クロル−３−ヨードマレイミド、
Ｎ−（ｎ−又はｉ−）プロピル−２−クロル−３
−ヨードマレイミド、Ｎ−（ｎ−、ｉ−、sec−又
はtert−）ブチル−２−クロル−３−ヨードマレ
イミド、Ｎ−アリル−２−クロル−３−ヨードマ
レイミド、Ｎ−メタリル−２−クロル−３−ヨー
ドマレイミド、Ｎ−プロパルギル−２−クロル−
３−ヨードマレイミド、Ｎ−ブチニル−２−クロ
ル−３−ヨードマレイミド、２−ブロム−３−ク
ロルマレイミド、Ｎ−（ｎ−又はｉ−）プロピル
−２−ブロム−３−クロルマレイミド、Ｎ−（ｎ
−、ｉ−、sec−又はtert−）ブチル−２−ブロ
ム−３−クロルマレイミド、Ｎ−アリル−２−ブ
ロム−３−クロルマレイミド、Ｎ−メタリル−２
−ブロム−３−クロルマレイミド、Ｎ−プロパル
ギル−２−ブロム−３−クロルマレイミド、Ｎ−
ブチニル−２−ブロム−３−クロルマレイミド、
２−ヨード−３−フルオロマレイミド、Ｎ−（ｎ
−又はｉ−）プロピル−２−ヨード−３−フルオ
ロマレイミド、Ｎ−（ｎ−、ｉ−、sec−又はtert
−）ブチル−２−ヨード−３−フルオロマレイミ
ド、Ｎ−アリル−２−ヨード−３−フルオロマレ
イミド、Ｎ−メタリル−２−ヨード−３−フルオ
ロマレイミド、Ｎ−プロパルギル−２−ヨード−
３−フルオロマレイミド、Ｎ−ブチニル−２−ヨ
ード−３−フルオロマレイミド、２−ブロム−３
−ヨードマレイシド、Ｎ−（ｎ−又はｉ−）プロ
ピル−２−ブロム−３−ヨードマレイミド、Ｎ−
（ｎ−、ｉ−、sec−又はtert−）ブチル−２−ブ
ロム−３−ヨードマレイミド、Ｎ−アリル−２−
ブロム−３−ヨードマレイミド、Ｎ−メタリル−
２−ブロム−３−ヨードマレイミド、Ｎ−プロパ
ルギル−２−ブロム−３−ヨードマレイミド、Ｎ
−プチニル−２−ブロム−３−ヨードマレイミ
ド、２−フルオロ−３−ブロムマレイミド、Ｎ−
（ｎ−又はｉ−）プロピル−２−フルオロ−３−
ブロムマレイミド、Ｎ−（ｎ−、ｉ−、sec−又は
tert−）ブチル−２−フルオロ−３−ブロムマレ
イミド、Ｎ−アリル−２−フルオロ−３−ブロム
マレイミド、Ｎ−メタリル−２−フルオロ−３−
ブロムマレイミド、Ｎ−プロパルギル−２−フル
オロ−３−ブロムマレイミド、Ｎ−ブチニル−２
−フルオロ−３−ブロムマレイミド、等が挙げら
れる。就中、Ｘ、Ｙが共に塩素原子である化合物、あ
るいは共に臭素原子である化合物が好ましい。こ
れらの化合物を例えば The present invention relates to a new pest repellent composition and pest repellent material. Conventionally, methods for exterminating various sanitary pests such as cockroaches include methods of spraying insecticides such as pyrethroid insecticides and methods of using various insect traps. These methods kill pests by killing or trapping insects, and can prevent damage such as feeding damage and blood sucking caused by the pests to a certain extent, but they do not apply to the inside of furniture such as kitchens, livestock sheds, water sheds, chests of drawers, etc. It is not possible to avoid the flying, approaching, contact, invasion, contamination, etc. of pests to the human body, agricultural crops, and other animals and plants, and a sufficient exterminating effect cannot be achieved. Moreover, in the above method, it is necessary to dispose of the pests after killing or capturing them, and it is particularly difficult to dispose of the pests that die after entering the furniture, etc., and they may actually become a source of contamination. On the other hand, a method using a pest repellent is known as a pest extermination method that can prevent the above pests from flying or entering, and of course does not require any treatment of dead insects. Research and development and proposals are being made on various substances that have the same properties. However, none of the various substances proposed above can exhibit a sufficiently satisfactory pest repellent effect, and only a few substances, including N,N-diethyl-meta-toluamide, can be used as sprays, It is only used as a repellent for blood-sucking pests such as mosquitoes, fleas, bed bugs, and stable flies in the form of lotions and creams. In view of the above-mentioned current situation, the present inventors have conducted various studies with the aim of providing a repellent that exhibits an excellent pest repellent effect and can almost certainly prevent the invasion of pests. As a result, it has been found that a specific compound represented by the following general formula () can exhibit pest repellent effects that meet the above objectives. The present invention was completed based on this new knowledge. That is, the present invention is based on the general formula (In the formula, X and Y may be the same or different and represent a hydrogen atom or a halogen atom. R is a hydrogen atom,
It represents an alkyl group, alkenyl group, alkynyl group, or cycloalkyl group having 3 to 8 carbon atoms. However, when both X and Y represent a halogen atom, R is not an alkyl group having 5 to 8 carbon atoms. The present invention relates to an insect repellent composition characterized by containing a compound represented by as an active ingredient, and an insect repellent material characterized by holding the composition on a base material. The pest repellent composition of the present invention can exhibit extremely excellent pest repellent effects because it contains the specific maleimide derivative represented by the above general formula () as an active ingredient. Its repellent effect is
Not only sanitary pests and blood-sucking pests such as cockroaches, flies, mosquitoes, horseflies, fleas, and bed bugs, but also burrs,
It is also effective against clothing pests such as carp moth, grain storage pests such as brown weevils and weevils, as well as ants, termites, and slugs. Therefore, the pest repellent composition of the present invention can be used in specific areas of the home such as entryways, kitchens, dining rooms, livestock sheds, farms, etc., and in storage furniture such as chests of drawers, food storage cabinets, costume cases, doll cases, etc. By applying it to human bodies, animals, plants, etc., it is possible to reliably prevent pests from flying into, approaching, contacting, invading, etc., and to prevent pests from inhabiting the above-mentioned specified areas. ,
It is possible to successfully avoid feeding damage, bites, blood sucking, etc. of animals and plants, and even contamination. The maleimide derivatives which are the active ingredients of the pest repellent composition of the present invention include X in the general formula (),
Y is a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, and R is a hydrogen atom with a carbon number of 3
Examples include compounds that are an alkyl group, an alkenyl group, an alkynyl group, or a cycloalkyl group having a linear or branched chain of 8 to 8. Specifically maleimide, N-(n- or i-)propylmaleimide,
N-(n-, iso-, sec- or tert-)butylmaleimide, N-(n-, iso- or neo-)pentylmaleimide, N-hexylmaleimide, N-
(1- or 2-methyl)pentylmaleimide, N
-heptylmaleimide, N-octylmaleimide, N-(2-ethylhexyl)-maleimide, N
-allylmaleimide, N-methallylmaleimide,
N-propargylmaleimide, N-butynylmaleimide, N-cyclopentylmaleimide, N-cyclohexylmaleimide, 2-chlormaleimide, N-(n- or i-)propyl-2-chlormaleimide, N-(n-, i- , sec- or tert
-) butyl-2-chlormaleimide, N-(n-,
i-, neo-)pentyl-2-chloromaleimide, N-(1- or 2-)methylpentyl-2-
Chlormaleimide, N-hexyl-2-chlormaleimide, N-heptyl-2-chlormaleimide, N-octyl-2-chlormaleimide, N-
(2-ethylhexyl)-2-chlormaleimide,
N-nonyl-2-chlormaleimide, N-decyl-2-chlormaleimide, N-undecyl-2-
Chlormaleimide, N-dodecyl-2-chlormaleimide, N-allyl-2-chlormaleimide,
N-methallyl-2-chlormaleimide, N-propargyl-2-chlormaleimide, N-butynyl-2-chlormaleimide, N-cyclopentyl-
2-Chlormaleimide, N-cyclohexyl-2
-Chlormaleimide, 2-bromaleimide, N
-Methyl-2-bromaleimide, N-ethyl-
2-bromaleimide, N-(n- or i-)propyl-2-bromaleimide, N-(n-,i
-, sec- or tert-)butyl-2-bromaleimide, N-(n-, i- or neo-)pentyl-2-bromaleimide, N-hexyl-2-bromaleimide, N-(1- or 2-bromaleimide) -) Methylpentyl-2-bromaleimide, N-heptyl-
2-bromaleimide, N-octyl-2-bromaleimide, N-(2-ethylhexyl)-2-
Bromaleimide, N-allyl-2-bromaleimide, N-methallyl-2-bromaleimide,
N-propargyl-2-bromaleimide, N-
Butynyl-2-bromaleimide, N-cyclopentyl-2-bromaleimide, N-cyclohexyl-2-bromaleimide, 2-iodomaleimide, N-(n- or i-)propyl-2-iodomaleimide, N-(n- -, i-, sec- or tert
-) butyl-2-iodomaleimide, N-(n-,
i- or neo-)pentyl-2-iodomaleimide, N-hexyl-2-iodomaleimide, N-
(1- or 2-) Methylpentyl-2-iodomaleimide, N-heptyl-2-iodomaleimide, N-octyl-2-iodomaleimide, N-
(2-ethylhexyl)-2-iodomaleimide,
N-allyl-2-iodomaleimide, N-methallyl-2-iodomaleimide, N-propargyl-
2-iodomaleimide, N-butynyl-2-iodomaleimide, N-cyclopentyl-2-iodomaleimide, N-cyclohexyl-2-iodomaleimide, 2-fluoromaleimide, N-(n-
or i-) propyl-2-fluoromaleimide,
N-(n-, i-, sec- or tert-)butyl-2
-Fluoromaleimide, N-(n-, i- or neo-)pentyl-2-fluoromaleimide, N-
Hexyl-2-fluoromaleimide, N-(1-
or 2-) methylpentyl-2-fluoromaleimide, N-heptyl-2-fluoromaleimide,
N-octyl-2-fluoromaleimide, N-
(2-Ethylhexyl)-2-fluoromaleimide, N-allyl-2-fluoromaleimide, N-
Methallyl-2-fluoromaleimide, N-propargyl-2-fluoromaleimide, N-butynyl-2-fluoromaleimide, N-cyclopentyl-2-fluoromaleimide, N-cyclohexyl-2-fluoromaleimide, 2,3-dichloromaleimide , N-(n- or i-)propyl-2,
3-dichloromaleimide, N-(n-, i-, sec
- or tert-)butyl-2,3-dichloromaleimide, N-allyl-2,3-dichloromaleimide, N-methallyl-2,3-dichloromaleimide, N-propargyl-2,3-dichloromaleimide , N-butynyl-2,3-dichloromaleimide, N-cyclopentyl-2,3-dichloromaleimide, N-cyclohexyl-2,3-dichloromaleimide, 2,3-dibromaleimide, N-
(n- or i-)propyl-2,3-dibromaleimide, N-(n-, i-, sec- or tert-)
Butyl-2,3-dibromaleimide, N-allyl-2,3-dibromaleimide, N-methallyl-2,3-dibromaleimide, N-propargyl-2,3-dibromaleimide, N-butynyl- 2,3-dibromaleimide, N-cyclopentyl-2,3-dibromaleimide, N-cyclohexyl-2,3-dibromaleimide, 2,3
-difluoromaleimide, N- (n- or i-)
Propyl-2,3-difluoromaleimide, N-
(n-, i-, sec- or tert-)butyl-2,3
-difluoromaleimide, N-allyl-2,3-
Difluoromaleimide, N-methallyl-2,3-
difluoromaleimide, N-propargyl-2,
3-difluoromaleimide, N-butynyl-2,
3-difluoromaleimide, N-cyclopentyl-2,3-difluoromaleimide, N-cyclohexyl-2,3-difluoromaleimide, 2,3
- diiodomaleimide, N-(n- or i-)propyl-2,3-diiodomaleimide, N-(n
-, i-, sec- or tert-)butyl-2,3-
Diiodomaleimide, N-allyl-2,3-diiodomaleimide, N-methallyl-2,3-diiodomaleimide, N-propargyl-2,3-diiodomaleimide, N-butynyl-2,3-diiodo maleimide, N-cyclopentyl-2,3-diiodomaleimide, N-cyclohexyl-2,3
-diiodomaleimide, 2-chloro-3-fluoromaleimide, N-(n- or i-)propyl-
2-chloro-3-fluoromaleimide, N-(n
-, i-, sec- or tert-)butyl-2-chloro-3-fluoromaleimide, N-allyl-2-
Chlor-3-fluoromaleimide, N-methallyl-2-chloro-3-fluoromaleimide, N-propargyl-2-chloro-3-fluoromaleimide, N-butynyl-2-chloro-3-fluoromaleimide, 2-chloro- 3-iodomaleimide,
N-(n- or i-)propyl-2-chloro-3
-iodomaleimide, N-(n-, i-, sec- or tert-)butyl-2-chloro-3-iodomaleimide, N-allyl-2-chloro-3-iodomaleimide, N-methallyl-2-chlor -3-iodomaleimide, N-propargyl-2-chloro-
3-iodomaleimide, N-butynyl-2-chloro-3-iodomaleimide, 2-bromo-3-chlormaleimide, N-(n- or i-)propyl-2-bromo-3-chloromaleimide, N-( n
-, i-, sec- or tert-)butyl-2-bromo-3-chlormaleimide, N-allyl-2-bromo-3-chlormaleimide, N-methallyl-2
-Bromo-3-chlormaleimide, N-propargyl-2-bromo-3-chlormaleimide, N-
butynyl-2-bromo-3-chlormaleimide,
2-iodo-3-fluoromaleimide, N-(n
- or i-) propyl-2-iodo-3-fluoromaleimide, N-(n-, i-, sec- or tert
-) Butyl-2-iodo-3-fluoromaleimide, N-allyl-2-iodo-3-fluoromaleimide, N-methallyl-2-iodo-3-fluoromaleimide, N-propargyl-2-iodo-
3-fluoromaleimide, N-butynyl-2-iodo-3-fluoromaleimide, 2-bromo-3
-iodomaleicide, N-(n- or i-)propyl-2-bromo-3-iodomaleimide, N-
(n-, i-, sec- or tert-)butyl-2-bromo-3-iodomaleimide, N-allyl-2-
Bromo-3-iodomaleimide, N-methallyl-
2-bromo-3-iodomaleimide, N-propargyl-2-bromo-3-iodomaleimide, N
-Ptynyl-2-bromo-3-iodomaleimide, 2-fluoro-3-bromaleimide, N-
(n- or i-)propyl-2-fluoro-3-
Bromaleimide, N-(n-, i-, sec- or
tert-)butyl-2-fluoro-3-bromaleimide, N-allyl-2-fluoro-3-bromaleimide, N-methallyl-2-fluoro-3-
Bromaleimide, N-propargyl-2-fluoro-3-bromaleimide, N-butynyl-2
-fluoro-3-bromaleimide, and the like. Particularly preferred are compounds in which X and Y are both chlorine atoms, or compounds in which both X and Y are bromine atoms. These compounds are e.g.

【式】で示されるマレイン酸無水物とRNH₂で示されるアミン類を
反応させることにより製造される。本発明の害虫忌避剤組成物は、上記有効成分化
合物をそのまま害虫忌避を要求される区域等に適
用することもできるが、通常好ましくは適当な担
体その他の配合剤を用いて適用区域、適用方法等
に適した各種の形態例えば液剤、固剤等に調製し
て利用される。液剤の形態に調製するに当り用い
られる担体としては例えば水、メチルアルコー
ル、エチルアルコール等のアルコール類、アセト
ン、メチルエチルケトン等のケトン類、テトラヒ
ドロフラン、ジオキサン等にエーテル類、ヘキサ
ン、ケロシン、パラフイン、石油ベンジン等の脂
肪族炭化水素類、ベンゼン、トルエン等の芳香族
炭化水素類、酢酸エチル等のエステル類、ジクロ
ロエタン等のハロゲン化炭化水素類等を例示でき
る。之等液剤の形態の本発明害虫忌避剤組成物に
は更に通常の塗膜形成剤、乳化剤、分散剤、展着
剤、湿潤剤、安定剤、噴射剤等の添加剤を配合す
ることができ、塗料形態、接着剤形態、乳剤、分
散剤、懸濁剤、ローシヨン、クリーム、噴霧剤、
エアゾール剤等の形態で利用することができる。
之等の添加剤としては、例えばニトロセルロー
ス、アセチルセルロース、アセチルブチリルセル
ロース、メチルセルロース等のセルロース誘導
体、酢酸ビニル樹脂等のビニル系樹脂、アルキツ
ド系樹脂、ユリア系樹脂、エポキシ系樹脂、ポリ
エステル系樹脂、ウレタン系樹脂、シリコン系樹
脂、アクリル系樹脂、塩化ゴム、ポリビニルアル
コール等の塗膜形成剤、石けん類、ポリオキシエ
チレンオレイルエーテルなどのポリオキシエチレ
ン脂肪アルコールエーテル、ポリオキシエチレン
ノニルフエニルエーテルなどのポリオキシエチレ
ンアルキルアリルエーテル、ポリオキシエチレン
脂肪族エステル、脂肪酸グリセリド、ソルビタン
脂肪酸エステル、高級アルコールの硫酸エステ
ル、ドデシルベンゼンスルホン酸ソーダなどのア
ルキルアリルスルホン酸塩等の界面活性剤、液化
石油ガス、ジメチルエーテル、フルオロカーボン
等の噴射剤、カゼイン、ゼラチン、アルギン酸、
CMC等を例示できる。また固剤の形態に調製するに当り用いられる担
体としては、例えばケイ酸、カオリン、活性炭、
ベントナイト、珪藻土、タルク、クレー、炭酸カ
ルシウム、陶磁器粉等の鉱物質粉末や、木粉、大
豆粉、小麦粉、でん粉等の植物質粉末等やシクロ
デキストリン等の包接化合物等を例示できる。更
に該固剤の形態に調製するに当つては、例えばト
リシクロデカン、シクロドデカン、２，４，６−
トリイソプロピル−１，３，５−トリオキサン、
トリメチレンノルボルネン等の昇華性担体やパラ
ジクロロベンゼン、ナフタリン、樟脳等の昇華性
防虫剤を用い、上記有効成分化合物を溶融混合又
は擂潰混合後成型して、昇華性固剤とすることも
できる。また本発明の害虫忌避剤組成物は、例えばポリ
ビニルアルコールやCMC等を用いたスプレード
ライ法、ゼラチン、ポリビニルアルコール、アル
ギン酸糖を用いた液中硬化法、コアセルベーシヨ
ン法等に従いマイクロカプセル化した形態に調製
したり、ベンジリデン−Ｄ−ソルビトール、カラ
ギーナン等のゲル化剤を用いてゲルの形態に調製
することもできる。更に本発明の害虫忌避剤組成物には、公知の害
虫忌避剤、効力増強剤、酸化防止剤、殺虫剤、げ
つ歯類動物駆除及び忌避剤、殺菌剤、防剤、除草
剤、肥料、着香料、着色料等を配合することがで
きる。配合可能な他の害虫忌避剤としては、Ｎ，
Ｎ−ジエチル−メタ−トルアミド、２，３，４，
５−ビス（A₂−ブチレン）−テトラヒドロフルフ
ラール、ジ−ｎ−プロピルイソシンコメロネー
ト、ジ−ｎ−ブチルサクシネート、２−ヒドロキ
シエチルオクチルサルフアイド等を、効力増強剤
としてはＮ−（２−エチルヘキシル）−ビシクロ−
〔２，２，１〕−５−ヘプテン−２，３−ジカルボ
キシイミド、６−（プロピルピペロニル）−ブチル
カルビチルエーテル等を、酸化防止剤としてはブ
チルヒドロキシアニソール、ジブチルヒドロキシ
トルエン、トコフエロール、γ−オリザノール等
を、殺虫剤としては一般名アレスリン及びその幾
何及び（又は）光学異性体等のピレスロイド類
を、げつ歯動物駆除及び忌避剤としてはα−ナフ
チルチオウレア、シクロヘキシミド等を、殺菌剤
としてはサリチル酸、ｐ−クロロ−ｍ−キシレノ
ール、２−（4′−チアゾイル）ベンズイミダゾー
ル等を、防黴剤としてはα−ブロモシンナミツク
アルデヒド、Ｎ−ジメチル−Ｎ−フエニル−
N′−（フルオロジクロロメチル）チオスルフアミ
ド等を夫々例示できる。かくして調製される各種形態を有する本発明の
害虫忌避剤組成物は、その使用に当り忌避効果を
要求される害虫の侵入区域例えば農作物栽培畑、
果樹園等、一般家庭、穀物倉庫、食堂の厨房、家
具、押入れ、玄関、洗面所等に、載置、撒布、噴
霧、塗布、貼り付け等により、また動植物体自体
に撒布、噴霧、塗布等により適用できる。本発明害虫忌避剤組成物中の有効成分化合物量
及び該忌避剤の適用量は、その剤型や適用方法、
適用場所等に応じて適宜に決定すればよく、限定
的ではないが、通常分散剤や水和剤等の液剤の形
態で用いる場合、有効成分化合物を１〜80重量％
好ましくは５〜40重量％含有させればよく、粉剤
等の固剤の形態とする場合１〜50重量％好ましく
は２〜20重量％含有させればよく、その適用量と
しては、例えば塗布使用の場合、塗布すべき面積
１cm²当りに有効成分化合物を0.01mg以上好ましく
は約0.01〜0.5mgとするのがよく、固剤その他の
形態で用いる場合、適用空間１m²当り有効成分化
合物を約100mg以上存在させるのが適当である。本発明はまた、上記害虫忌避剤組成物を基材に
保持させてなる害虫忌避材をも提供するものであ
る。該害虫忌避材は、その基材の特性を利用して
害虫忌避性を有するシート状基材や家具部材等と
して用いられる。ここで基材としては、例えばポリエチレン、ポ
リプロプレン、ナイロン、ポリ塩化ビニル、ポリ
塩化ビニリデン、ポリエステル等の合成樹脂シー
ト、動植物質又は無機質繊維体シート（紙、布、
不織布、皮革、カーペツト等）、之等合成樹脂と
無機質繊維または粉体との混合シートまたは混紡
糸、上記合成樹脂と動植物繊維との混紡布または
不織布、アルミニウム、ステンレス、亜鉛等の金
属の箔乃至フイルム及び上記各種シートの積層シ
ートを例示できる。更に上記基材としては、これ
を家具部材とする天然木材例えばキリ、ペンシル
シダ、クス等やプラスチツクス例えば塩化ビニル
樹脂、塩素化ポリエチレン、ポリエチレン、ポリ
プロピレン等の成型物をも有効に利用できる。之等基材への本発明害虫忌避剤組成物の保持手
段は、踏に制限はなく、例えば塗布、含浸、滴
下、混練等により保持させて、該基材に保持され
た形態で目的とする箇所に載置したり貼り合せる
ことにより利用することができる。保持量も特に制限はなく、適宜に決定できる
が、基材等の飽和含浸量のほぼ1/2倍量を保持さ
せればよい。以下本発明を更に詳しく説明するため実施例を
挙げる。なお、実験には第１表に示す化合物を用
いた。各実施例に於ける供試化合物No.は第１表の
化合物No.に対応する。It is produced by reacting maleic anhydride represented by the formula with amines represented by RNH ₂ . In the pest repellent composition of the present invention, the above-mentioned active ingredient compound can be applied as it is to areas where pest repellency is required, but it is usually preferable to use an appropriate carrier or other compounding agents to determine the application area and application method. It is prepared and used in various forms suitable for use, such as liquids and solids. Examples of carriers used in preparing liquid preparations include water, alcohols such as methyl alcohol and ethyl alcohol, ketones such as acetone and methyl ethyl ketone, ethers such as tetrahydrofuran and dioxane, hexane, kerosene, paraffin, and petroleum benzine. Examples include aliphatic hydrocarbons such as benzene and toluene, aromatic hydrocarbons such as benzene and toluene, esters such as ethyl acetate, and halogenated hydrocarbons such as dichloroethane. The pest repellent composition of the present invention in the form of a liquid may further contain conventional additives such as film forming agents, emulsifiers, dispersants, spreading agents, wetting agents, stabilizers, and propellants. , paint form, adhesive form, emulsion, dispersant, suspension agent, lotion, cream, spray,
It can be used in the form of an aerosol or the like.
Examples of such additives include cellulose derivatives such as nitrocellulose, acetylcellulose, acetylbutyrylcellulose, and methylcellulose, vinyl resins such as vinyl acetate resin, alkyd resins, urea resins, epoxy resins, and polyester resins. , urethane resins, silicone resins, acrylic resins, chlorinated rubber, coating film forming agents such as polyvinyl alcohol, soaps, polyoxyethylene fatty alcohol ethers such as polyoxyethylene oleyl ether, polyoxyethylene nonyl phenyl ether, etc. Surfactants such as polyoxyethylene alkyl allyl ether, polyoxyethylene aliphatic ester, fatty acid glyceride, sorbitan fatty acid ester, sulfuric acid ester of higher alcohol, alkyl allyl sulfonate such as sodium dodecylbenzene sulfonate, liquefied petroleum gas, Propellants such as dimethyl ether and fluorocarbons, casein, gelatin, alginic acid,
Examples include CMC. In addition, examples of carriers used for preparation in solid form include silicic acid, kaolin, activated carbon,
Examples include mineral powders such as bentonite, diatomaceous earth, talc, clay, calcium carbonate, and ceramic powder, vegetable powders such as wood flour, soybean flour, wheat flour, and starch, and clathrate compounds such as cyclodextrin. Furthermore, when preparing the solid agent form, for example, tricyclodecane, cyclododecane, 2,4,6-
triisopropyl-1,3,5-trioxane,
It is also possible to form a sublimable solid agent by melt-mixing or grinding the above-mentioned active ingredient compounds using a sublimable carrier such as trimethylene norbornene, or a sublimable insect repellent such as paradichlorobenzene, naphthalene, or camphor. In addition, the pest repellent composition of the present invention can be microencapsulated according to a spray drying method using polyvinyl alcohol, CMC, etc., an in-liquid curing method using gelatin, polyvinyl alcohol, alginate sugar, a coacelvation method, etc. It can also be prepared in the form of a gel using a gelling agent such as benzylidene-D-sorbitol or carrageenan. Furthermore, the pest repellent composition of the present invention includes known pest repellents, efficacy enhancers, antioxidants, insecticides, rodent control and repellents, fungicides, preventive agents, herbicides, fertilizers, Flavoring agents, coloring agents, etc. can be added. Other pest repellents that can be blended include N,
N-diethyl-meta-toluamide, 2,3,4,
5-bis(A ₂ -butylene)-tetrahydrofurfural, di-n-propylisocincomeronate, di-n-butylsuccinate, 2-hydroxyethyloctylsulfide, etc., and N-(2 -ethylhexyl)-bicyclo-
[2,2,1]-5-heptene-2,3-dicarboximide, 6-(propylpiperonyl)-butyl carbityl ether, etc., and antioxidants such as butylhydroxyanisole, dibutylhydroxytoluene, tocopherol. , γ-oryzanol, etc., pyrethroids such as the common name allethrin and its geometric and/or optical isomers as insecticides, α-naphthylthiourea, cycloheximide, etc. as rodent extermination and repellents, and bactericidal agents. Examples of antifungal agents include salicylic acid, p-chloro-m-xylenol, 2-(4'-thiazoyl)benzimidazole, etc., and antifungal agents include α-bromosinnamic aldehyde, N-dimethyl-N-phenyl-
Examples include N'-(fluorodichloromethyl)thiosulfamide and the like. The pest repellent composition of the present invention having various forms thus prepared can be used in areas infested by pests where a repellent effect is required, such as agricultural fields,
Place, sprinkle, spray, apply, paste, etc. on orchards, general households, grain warehouses, cafeteria kitchens, furniture, closets, entrances, washrooms, etc., and apply, spray, apply, etc. on animals and plants themselves. It can be applied by The amount of the active ingredient compound in the pest repellent composition of the present invention and the application amount of the repellent are determined by its dosage form, application method,
It may be determined as appropriate depending on the place of application, etc., and although it is not limited, usually when used in the form of a liquid such as a dispersant or a wettable powder, the active ingredient compound is 1 to 80% by weight.
Preferably, the content may be from 5 to 40% by weight, and when it is in the form of a solid agent such as a powder, it may be from 1 to 50% by weight, preferably from 2 to 20% by weight. In this case, the amount of the active ingredient compound should be 0.01 mg or more, preferably about 0.01 to 0.5 mg per 1 cm ² of the area to be applied, and when used in a solid or other form, the amount of the active ingredient compound should be about 0.01 mg or more per 1 cm ² of the application space. It is appropriate to have it present in an amount of 100 mg or more. The present invention also provides a pest repellent material in which the pest repellent composition described above is retained on a base material. The pest repellent material is used as a sheet-like base material, furniture member, etc. that has pest repellent properties by utilizing the characteristics of the base material. Examples of the base material here include synthetic resin sheets such as polyethylene, polypropylene, nylon, polyvinyl chloride, polyvinylidene chloride, and polyester, animal and vegetable or inorganic fiber sheets (paper, cloth,
(nonwoven fabric, leather, carpet, etc.), mixed sheets or blended yarns of synthetic resins and inorganic fibers or powders, blended fabrics or nonwoven fabrics of the above synthetic resins and animal and plant fibers, metal foils such as aluminum, stainless steel, zinc, etc. Examples include laminated sheets of films and the above-mentioned various sheets. Further, as the above-mentioned base material, molded materials such as natural wood such as awn, pencil fern, oak, etc. and plastics such as vinyl chloride resin, chlorinated polyethylene, polyethylene, polypropylene, etc., which are used as furniture members, can also be effectively used. The means for retaining the pest repellent composition of the present invention on the substrate is not limited, for example, by coating, impregnating, dropping, kneading, etc., and the pest repellent composition of the present invention is retained on the substrate to achieve the desired purpose. It can be used by placing it on a spot or pasting it together. The retained amount is not particularly limited and can be determined as appropriate, but it is sufficient to retain approximately 1/2 of the saturated impregnated amount of the base material, etc. Examples will be given below to explain the present invention in more detail. Note that the compounds shown in Table 1 were used in the experiment. The test compound numbers in each example correspond to the compound numbers in Table 1.

【表】【table】

【表】実施例１第２表に示される各化合物につき、そのチヤバ
ネゴキブリに対する忌避効果を次の方法により調
べる。即ち各供試化合物の0.1mg／cm²を円形紙
（径11cm）に含浸させ、その中央及び何ら供試化
合物を含浸させない対照紙の中央に夫々角砂糖
１個を置き、これら各１対を、チヤバネゴキブリ
成虫雄雌各25頭を飼育している飼育箱内に重なら
ないように並べ、３日間放置後の各紙上角砂糖
の重量減少量（喫食量）（Ｘmgとする）を測定す
る。各供試化合物の忌避効果は、対照紙上の角
砂糖の減少量（喫食量）（Ａmgとする）を基準と
し、下式に従い算出される。忌避効果（％）＝Ａ（mg）−Ｘ（mg）／Ａ（mg）×100 得られた結果を次の基準により判定し、下記第
２表に示す。 …忌避効果90％以上 … 〃 70〜90％＋ … 〃 50〜70％ ± … 〃 30〜50％ − … 〃 30％以下[Table] Example 1 The repellent effect of each compound shown in Table 2 on German cockroaches was investigated by the following method. That is, a circular piece of paper (diameter 11 cm) was impregnated with 0.1 mg/cm ² of each test compound, one sugar cube was placed in the center of the circular paper (diameter 11 cm), and one sugar cube was placed in the center of the control paper that was not impregnated with any test compound. Arrange them so that they do not overlap in a breeding box in which 25 male and female adult German cockroaches are kept, and measure the weight loss (eating amount) of each paper sugar cube (taken as X mg) after leaving it for 3 days. The repellent effect of each test compound is calculated according to the following formula, based on the amount of sugar cube reduction (eaten amount) (Amg) on the control paper. Repellent effect (%) = A (mg) - X (mg) / A (mg) x 100 The obtained results were judged according to the following criteria and are shown in Table 2 below. …Repellent effect 90% or more … 〃 70-90% + … 〃 50-70% ± … 〃 30-50% − … 〃 30% or less

【表】上表より本発明において有効成分とする一般式
（）で表わされる化合物は、いずれも優れた忌
避効果を有することが明らかである。実施例２第３表に示す各有効成分化合物を用いて下記組
成のローシヨンの形態を有する本発明害虫忌避剤
組成物を製造する。ミリスチン酸イソプロピル２ｇ精製水 15ｇ香料微量エタノール全体を100ｇとする量また上記有効成分化合物を配合しない以外は上
記と同様にして対照ローシヨンを製造する。得られた各ローシヨンにつき、アカイエカ雌成
虫の忌避効力試験を次の通り行なう。即ち本発明
ローシヨン１mlを一方の腕に均一に塗布し、他方
の腕に対照ローシヨンを同様に塗布後、１時間及
び６時間経過後に夫々の腕をそれぞれアカイエカ
雌成虫各20頭を入れたケージに入れ、30分間静止
吸血させ、その型各ケージ内の蚊を麻酔後紙上
で押しつぶし紙上血痕の数で吸血虫の判定を行
ない、対照ローシヨンを用いた場合の血痕数を基
準として、下式に従い各供試ローシヨンの忌避効
力を判断する。忌避効果（％）＝（対照ローシヨン使用時血痕数）
−（供試ローシヨン使用時血痕数）／（対照ローシヨン
使用時血痕数）×100 得られた結果を下記基準により、第３表に表記
する。 …忌避効果90％以上 … 〃 70〜90％＋ … 〃 50〜70％ ± … 〃 30〜50％ − … 〃 30％以下[Table] It is clear from the above table that all the compounds represented by the general formula () used as active ingredients in the present invention have excellent repellent effects. Example 2 A pest repellent composition of the present invention in the form of a lotion having the following composition is produced using each of the active ingredient compounds shown in Table 3. Isopropyl myristate 2g Purified water 15g Fragrance Trace amount of ethanol Amount to make the total 100g A control lotion is also produced in the same manner as above except that the above active ingredient compound is not added. For each of the obtained lotions, a test for repellency against adult female Culex pipiens was conducted as follows. Specifically, 1 ml of the lotion of the present invention was evenly applied to one arm, and a control lotion was similarly applied to the other arm. After 1 hour and 6 hours, each arm was placed in a cage containing 20 adult Culex Culex mosquitoes. The mosquitoes in each type of cage were anesthetized and then allowed to suck blood for 30 minutes. After anesthesia, the mosquitoes in each cage were crushed on paper and blood-sucking insects were determined by the number of bloodstains on the paper. Determine the repellent efficacy of the test lotion. Repellent effect (%) = (Number of blood stains when using control lotion)
- (Number of bloodstains when using the test lotion) / (Number of bloodstains when using the control lotion) x 100 The obtained results are shown in Table 3 according to the following criteria. …Repellent effect 90% or more … 〃 70-90% + … 〃 50-70% ± … 〃 30-50% − … 〃 30% or less

【表】実施例３純毛の布（10cm×10cm）に下記供試化合物を
0.05mg／cm²の割合で含浸させ、これを無含浸布と
１対として、コイガ幼虫30頭を入れた直径30cmの
シヤーレ内に並べて入れ、７日間放置後、各布の
食害の程度を調べ、無含浸布の喫食量を基準とし
て各供試化合物の忌避効果を次式により算出す
る。忌避効果（％）＝対照布喫食量（mg）−供試布喫食
量（mg）／対照布喫食量（mg）×100 得られた結果を第１表と同様の基準に従い、下
記第４表に示す。[Table] Example 3 The following test compound was applied to a pure wool cloth (10cm x 10cm).
Impregnated at a rate of 0.05 mg/cm ² , this was paired with a non-impregnated cloth and placed side by side in a 30 cm diameter shear containing 30 carp moth larvae, and after being left for 7 days, the degree of feeding damage on each cloth was examined. The repellent effect of each test compound is calculated using the following formula based on the amount of food consumed on unimpregnated cloth. Repellent effect (%) = Control fabric consumption (mg) - Sample fabric consumption (mg) / Control fabric consumption (mg) x 100 The obtained results are summarized in Table 4 below according to the same criteria as Table 1. Shown below.

【表】実施例４円形紙（径５cm）に、下記各供試化合物を
0.5mg／cm²の割合で含浸させ、これを無含浸紙
と１対としその夫々に角砂糖各１個をのせ、アミ
メアリ200匹を入れたシヤーレ（径30cm）内に並
べ、10分間放置後、各紙上のアリ数を計数し、
無含浸紙上における数を基準として、下式に従
い各供試化合物の忌避効果を判定する。忌避効果（％）＝無含浸紙上アリ数（匹）−供試
紙上アリ数（匹）／無含浸紙上アリ数（匹）×100 得られた結果を第１表と同様の基準に従い、下
記第５表に示す。[Table] Example 4 Each of the following test compounds was placed on a circular paper (5 cm in diameter).
Impregnated at a rate of 0.5mg/cm ² , pair this with non-impregnated paper, place one sugar cube on each, arrange them in a chale (diameter 30cm) containing 200 red-eared ants, and leave for 10 minutes. Count the number of ants on each paper,
Based on the number on non-impregnated paper, the repellent effect of each test compound is determined according to the following formula. Repellent effect (%) = Number of ants on non-impregnated paper (number of ants) - Number of ants on test paper (number of ants) / Number of ants on non-impregnated paper (number of ants) x 100 Based on the same criteria as in Table 1, the obtained results were calculated according to the following table. It is shown in Table 5.

【表】実施例５イエバエの餌に下記各供試化合物の0.1％及び
殺虫剤（「スミチオン」、住友化学工業株式会社製
有機リン系殺虫剤）の0.01％又は上記殺虫剤のみ
を夫々配合し、之等をイエバエ成虫雌雄各100頭
を入れた二つの飼育箱に夫々別々に入れ、１時間
後各箱内の誘殺ハエ数を計数し、殺虫剤のみを配
合した毒餌における結果（対照）を基準として、
各供試化合物の忌避効果を次式により算出する。忌避効果（％）＝対照死虫数（頭）−検体死虫数（
頭）／対照死虫数（頭）×100 得られた結果を第１表と同様の基準に従い、下
記第６表に示す。[Table] Example 5 House fly bait was mixed with 0.1% of each of the following test compounds and 0.01% of an insecticide ("Sumithion", an organophosphorus insecticide manufactured by Sumitomo Chemical Co., Ltd.), or only the above insecticide, respectively. , etc. were placed separately in two breeding boxes containing 100 male and 100 male and female house flies, and after 1 hour, the number of attracted flies in each box was counted, and the results were compared with the poisoned bait containing only insecticide (control). As a standard,
The repellent effect of each test compound is calculated using the following formula. Repellent effect (%) = Number of dead control insects (heads) - Number of dead insects sampled (
head)/control number of dead insects (head) x 100 The results obtained are shown in Table 6 below according to the same criteria as in Table 1.

【表】実施例６円形紙（径５cm）に、下記各供試化合物0.1
mg／cm²を含浸させ、これと無含浸紙とを１対と
し、これらの夫々中央に白米をのせ、コクヌスト
モドキ成虫雄雌各10頭を入れてあるシヤーレ（直
径30cm）内に並べ、１時間放置後各紙上のコク
ヌストモドキの数を計え、無含浸紙における結
果を標準として、実施例５と同様にして各供試化
合物を用いた場合の忌避効果を算出する。得られた結果を下記第７表に示す。[Table] Example 6 0.1 of each of the following test compounds was placed on a circular paper (diameter 5 cm).
mg/cm ² , make a pair of this and unimpregnated paper, place white rice in the center of each pair, arrange them in a siere (diameter 30 cm) containing 10 male and 10 male and female Coconut flora adults, and After being left for a period of time, the number of brown fleas on each paper was counted, and the repellent effect when each test compound was used was calculated in the same manner as in Example 5, using the results on non-impregnated paper as a standard. The results obtained are shown in Table 7 below.

【表】実施例７第８表記載の各供試化合物を夫々用いて下記組
成の油剤の形態を有する本発明害虫忌避剤組成物
を製造する。有効成分化合物５ｇエチルセロソルブ 20ｇ無臭灯油全量を100ｇとする量同様にして有効成分化合物を含有しない対照油
剤を製造する。かくして得られた各油剤を、入口内寸４cm×30
cmのベニヤ板製箱（内寸20×30×４cm）の各内壁
５面に供試化合物量約0.5mg／cm²となる量（対照
油剤にあつてはこれに相当する量）を噴霧塗布
し、得られた各箱を、チヤバネゴキブリ400匹を
飼育しているケース内に一夜（12時間）放置し、
チヤバネゴキブリの上記箱内への侵入居住数を計
数する。得られた結果より下記基準に従い、各油
剤の忌避効果を判定する。０ …居住数０＋ … 〃１〜４匹 … 〃５〜９匹 … 〃 10匹以上結果を下記第８表に示す。[Table] Example 7 Using each of the test compounds listed in Table 8, a pest repellent composition of the present invention in the form of an oil having the composition shown below is produced. Active ingredient compound 5g Ethyl cellosolve 20g Odorless kerosene Amount to bring the total amount to 100g A control oil solution containing no active ingredient compound is produced in the same manner. Each of the oils obtained in this way was
The test compound was sprayed in an amount of approximately 0.5 mg/cm ² (corresponding amount for the control oil) onto each of the five inner walls of a plywood box (inner dimensions 20 x 30 x 4 cm). , each box obtained was left overnight (12 hours) in a case housing 400 German cockroaches.
The number of German cockroaches invading the box is counted. Based on the obtained results, the repellent effect of each oil agent was judged according to the following criteria. 0... Number of residents: 0 +... 1 to 4 animals... 5 to 9 animals... 10 or more animals The results are shown in Table 8 below.

【表】実施例８上記第８表記載の各供試化合物を夫々用いて下
記組成の製剤の形態を有する本発明害虫忌避剤組
成物を製造する。有効成分化合物５ｇポリオキシエチレンオレイルエーテル（15モル）
10ｇ水全量を100ｇとする量同様にして有効成分化合物を含有しない対照製
剤を製造する。これらを直径15cmの円形紙に２ml滴下含浸さ
せ風乾し、本発明試料及び対照試料を得る。縦30cm×横40cm×高さ20cmのベニヤ板製箱内に
ナメクジ50匹を放飼し、上記本発明試料又は対照
試料とのそれぞれ２枚を上記ベニヤ板製箱の底に
並べて載置し、夫々の試料上に野菜クズを入れた
プラスチツク製シヤーレ（直径５cm×高さ１cm）
を夫々設置し、設置１日目及び３日目の野菜クズ
上のナメクジの数を計測する。その結果ナメクジは本発明試料上に載置した野
菜クズの入つたシヤーレには全く近づかず、すべ
て、対照試料上に載置した野菜クズの入つたシヤ
ーレ内に存在しており、本発明試料がナメクジ忌
避効果を有することが明らかであつた。実施例９上記実施例７で用いた本発明の供試化合物の
夫々10ｇに香料微量、エチルセロソルブ20ml及び
無臭灯油の全体を150mlとする量を加え、これと
液化石油ガス及びジメチルエーテル混合物（50：
50容積比）の150mlとをエアゾール用耐圧缶（内
容400ml）に充填して噴射装置に取り付け密封し
てエアゾール剤の形態の本発明害虫忌避剤組成物
を得る。かくして得られた各エアゾール剤を用い、実施
例７と同様にしてチヤバネゴキブリに対する忌避
効果試験を行なつた所、第８表記載の結果と同等
の結果を得た。実施例 10 実施例７で用いた本発明の供試化合物夫々５
ｇ、ニトロセルロース25ｇ、シンナー25ｇ及びジ
ブチルフタレート２ｇを混合溶解して、塗料形態
の本発明害虫忌避剤組成物を得る。かくして得られた各塗料を用い、実施例７と同
様に忌避効果試験を行なつた所、第８表記載の結
果と同様の結果を得た。実施例 11 実施例７で用いた本発明の供試化合物の夫々５
ｇ及び効力増強剤としてＮ−（２−エチルヘキシ
ル）−ビシクロ−〔２，２，１〕−５−ヘプテン−
２，３−ジカルボキシイミド５ｇをｎ−ヘキサン
１に希釈し、不織布（ポリエチレン−木綿
（３：１重量比）製、厚さ300μ、面積１m²）に、
供試化合物が３ｇとなるように含浸後乾燥して、
シート状形態の本発明害虫忌避材を得る。得られたシートを、入口内寸４cm×30cmのベニ
ヤ板製箱（内寸20×30×４cm）の各内壁５面に合
つた大きさに切断後貼り合せ、実施例７と同様に
忌避効果試験に供した所、第８表記載の結果とほ
ぼ同等の結果を得た。実施例 12 実施例７で用いた本発明の供試化合物３重量
部、酸化ケイ素１重量部及びシクロドデカン96重
量部を充分に擂潰混合後、300Kg／cm²の加圧下に
10ｇ／錠に打錠し、錠剤の形態を有する本発明害
虫忌避剤組成物を得る。得られた錠剤を実施例７記載のベニヤ板製箱内
に各箱２錠づつ入れ、同様の忌避効果試験を行な
つた所略々同様の結果を得た。実施例 13 実施例７で用いた本発明の供試化合物の夫々を
酸化ケイ素の同重量と充分撹拌混合後粉状化し
て、粉末状形態の本発明害虫忌避剤組成物を得
る。得られた粉末各３ｇを布製袋に充填しその各１
袋を実施例12と同様にベニヤ板製箱内に入れ同様
の忌避効果試験に供した所、ほぼ同様の結果を得
た。実施例 14 実施例７で用いた本発明の供試化合物６重量部
を２，４，６−トリイソプロピル−１，３，５−
トリオキサン94重量部と混合後約90℃で加熱溶解
した液中に、桐製板（15cm×150cm×２cm厚さ）
を浸漬し、15Kg／cm²で加圧処理して、木材重量の
約25％となる量の液を含浸させて、害虫忌避剤保
持木材の形態の本発明害虫忌避材を得る。得られた各木材を用いて実施例７記載の箱と同
一寸法の箱を貼合せ作成し、この箱（有効成分保
持量約15ｇ）につき同様の害虫忌避効果試験を行
なつた所ほぼ同様の結果を得た。実施例 15 10×５cmに裁断したカーペツト（未防虫処理市
販品）の表面に供試化合物のアセトン溶液３mlを
スプレーして処理する（薬量は0.6ｇ／m²）。この
処理カーペツトと、同じ大きさの未処理カーペツ
トとを長辺で間隙なくつなぎあわせ、その上にプ
ラスチツクの円筒を置く。別に30頭のアミメアリ
（職蟻）を入れた直径３cmの小型シヤーレを用意
し、未処理カーペツト上に伏せておく。しばらく
放置してアリの活動を安定させたのちシヤーレを
取り除き、時間の経過に伴つて処理カーペツトに
侵入するアリの数を観察して忌避効果を判定し
た。結果を第９表に示す。[Table] Example 8 Using each of the test compounds listed in Table 8 above, a pest repellent composition of the present invention having the form of a formulation having the following composition is produced. Active ingredient compound 5g polyoxyethylene oleyl ether (15 mol)
10g water Amount to bring the total amount to 100g A control formulation containing no active ingredient compound is manufactured in the same manner. A circular paper with a diameter of 15 cm is impregnated with 2 ml of these drops and air-dried to obtain a sample of the present invention and a control sample. Fifty slugs were released in a plywood box measuring 30 cm long x 40 cm wide x 20 cm high, and two samples of each of the above-mentioned inventive sample and control sample were placed side by side on the bottom of the plywood box, and each Plastic shear dish with vegetable scraps placed on the sample (diameter 5cm x height 1cm)
The number of slugs on the vegetable scraps was counted on the first and third day of installation. As a result, the slugs did not approach the dish containing vegetable scraps placed on the sample of the present invention at all, and all slugs were present in the dish containing vegetable scraps placed on the control sample. It was clear that it had a slug repellent effect. Example 9 To 10 g of each of the test compounds of the present invention used in Example 7 above, a trace amount of fragrance, 20 ml of ethyl cellosolve, and an amount of odorless kerosene to bring the total to 150 ml were added, and this was mixed with a mixture of liquefied petroleum gas and dimethyl ether (50:
50 volume ratio) into a pressure-resistant aerosol can (content: 400 ml), which is attached to an injection device and sealed to obtain the pest repellent composition of the present invention in the form of an aerosol. Using each of the aerosols thus obtained, a test for repelling effect on German cockroaches was conducted in the same manner as in Example 7, and results equivalent to those shown in Table 8 were obtained. Example 10 5 of each of the test compounds of the present invention used in Example 7
g, 25 g of nitrocellulose, 25 g of thinner and 2 g of dibutyl phthalate are mixed and dissolved to obtain the pest repellent composition of the present invention in the form of a paint. Using each of the paints thus obtained, a repellent effect test was conducted in the same manner as in Example 7, and results similar to those shown in Table 8 were obtained. Example 11 5 of each of the test compounds of the present invention used in Example 7
g and N-(2-ethylhexyl)-bicyclo-[2,2,1]-5-heptene- as a potency enhancer.
5 g of 2,3-dicarboximide was diluted with 1 part of n-hexane and applied to a nonwoven fabric (made of polyethylene-cotton (3:1 weight ratio), thickness 300 μ, area 1 m ² ).
After impregnation with 3 g of the test compound, dry it.
A sheet-like pest repellent material of the present invention is obtained. The obtained sheet was cut into a size that matched each of the five inner walls of a plywood box (inner dimensions 20 x 30 x 4 cm) with an entrance inner dimension of 4 cm x 30 cm, and then pasted, and a repellent effect test was conducted in the same manner as in Example 7. When the sample was subjected to the same procedure, results almost the same as those shown in Table 8 were obtained. Example 12 3 parts by weight of the test compound of the present invention used in Example 7, 1 part by weight of silicon oxide, and 96 parts by weight of cyclododecane were thoroughly ground and mixed, and then placed under a pressure of 300 kg/cm ²
The pest repellent composition of the present invention in tablet form is obtained by compressing into 10 g/tablet. The obtained tablets were placed in the plywood boxes described in Example 7, 2 tablets in each box, and the same repellent effect test was conducted, and almost the same results were obtained. Example 13 Each of the test compounds of the present invention used in Example 7 is sufficiently stirred and mixed with the same weight of silicon oxide, and then pulverized to obtain a powdered pest repellent composition of the present invention. Fill 3g of each of the obtained powders into cloth bags and
The bag was placed in a plywood box in the same manner as in Example 12 and subjected to the same repellent effect test, and almost the same results were obtained. Example 14 6 parts by weight of the test compound of the present invention used in Example 7 was added to 2,4,6-triisopropyl-1,3,5-
A paulownia wood board (15cm x 150cm x 2cm thick) was mixed with 94 parts by weight of trioxane and heated to about 90°C.
The pest repellent material of the present invention in the form of pest repellent-retaining wood is obtained by soaking the wood and applying a pressure treatment at 15 kg/cm ² to impregnate it with a liquid in an amount of about 25% of the weight of the wood. A box with the same dimensions as the box described in Example 7 was made using each of the obtained woods, and a similar pest repellent effect test was conducted on this box (active ingredient holding amount: approximately 15 g). Got the results. Example 15 The surface of a carpet cut to 10 x 5 cm (commercially available product that has not been treated with insect repellent) is treated by spraying 3 ml of an acetone solution of the test compound (dose amount: 0.6 g/m ² ). This treated carpet and an untreated carpet of the same size are joined together along the long sides without gaps, and a plastic cylinder is placed on top of them. Separately, prepare a small 3 cm diameter sieve containing 30 worker ants and place it face down on an untreated carpet. After leaving it for a while to stabilize the ant activity, the shear was removed and the repellent effect was determined by observing the number of ants that invaded the treated carpet over time. The results are shown in Table 9.

【table】

Claims

[Claims] 1. General formula (In the formula, X and Y may be the same or different and represent a hydrogen atom or a halogen atom. R represents a hydrogen atom, an alkyl group having 3 to 8 carbon atoms, an alkenyl group, an alkynyl group, or a cycloalkyl group. However, X and Y both represent a halogen atom, R is not an alkyl group having 5 to 8 carbon atoms.) An insect repellent composition comprising a maleimide compound as an active ingredient. 2 General formula (In the formula, X and Y may be the same or different and represent a hydrogen atom or a halogen atom. R represents a hydrogen atom, an alkyl group having 3 to 8 carbon atoms, an alkenyl group, an alkynyl group, or a cycloalkyl group. However, X and Y both represent a halogen atom, R is not an alkyl group having 5 to 8 carbon atoms. A pest repellent material that retains insects.