JP3189917B2 - An insecticide, insect repellent and repellent containing a cyclopropanecarboxylic acid ester derivative, and an insecticide, insect repellent and repellent method using the same. - Google Patents
An insecticide, insect repellent and repellent containing a cyclopropanecarboxylic acid ester derivative, and an insecticide, insect repellent and repellent method using the same.Info
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- JP3189917B2 JP3189917B2 JP03392293A JP3392293A JP3189917B2 JP 3189917 B2 JP3189917 B2 JP 3189917B2 JP 03392293 A JP03392293 A JP 03392293A JP 3392293 A JP3392293 A JP 3392293A JP 3189917 B2 JP3189917 B2 JP 3189917B2
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- repellent
- insecticide
- compound
- insect repellent
- insect
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Description
【０００１】[0001]
【産業上の利用分野】本発明は、常温または加熱揮散性
殺虫、防虫、忌避剤、ならびにこれを用いた殺虫、防
虫、忌避方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an insecticide, insect repellent and repellent which are volatile at normal temperature or under heat, and a method for insect repellent, insect repellent and repellent using the same.
【０００２】[0002]
【従来の技術】ベンジルアルコールエステル系の殺虫剤
としては今まで各種のものが知られており、３−フェノ
キシベンジルアルコールの菊酸エステルであるフェノト
リン等はその代表的なものである。これらのベンジルア
ルコールエステル系ピレスロイドは、殺虫活性が高く化
学的にも安定で、合成が比較的簡便であり、温血動物に
低毒性であるなどの特徴を有しており、その用途の拡大
が期待されているが、常温および加熱時の揮散性がやや
悪く、衣料用防虫剤や、加熱蒸散用の殺虫剤としては満
足すべきものではなかった。2. Description of the Related Art Various benzyl alcohol ester-based insecticides have been known so far, and phenothrin, which is a chrysanthemic acid ester of 3-phenoxybenzyl alcohol, is a typical example. These benzyl alcohol ester pyrethroids have high insecticidal activity, are chemically stable, are relatively easy to synthesize, and have low toxicity to warm-blooded animals. Although expected, the volatility at normal temperature and during heating is somewhat poor, and it was not satisfactory as an insecticide for clothing or an insecticide for heat evaporation.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、衛生害虫、
不快害虫および衣料害虫駆除用に供される殺虫、防虫、
忌避剤について、高い殺虫、防虫、忌避効果、温血動物
に対する低毒性、化学的安定性、ならびに常温および加
熱時の高揮散性等の要求を全て満足させることを目的と
してなされたものである。SUMMARY OF THE INVENTION The present invention relates to a sanitary pest,
Insecticides, insect repellents used for controlling discomfort pests and clothing pests,
The purpose of the repellent is to satisfy all requirements such as high insecticidal, insect repellent, repellent effects, low toxicity to warm-blooded animals, chemical stability, and high volatility at normal temperature and when heated.
【０００４】[0004]
【課題を解決するための手段】上記目的を達成するた
め、本発明は、一般式ＩIn order to achieve the above object, the present invention provides a compound of the general formula I
【化３】 （式中、Ｒは、フッ素、塩素、トリフルオロメチルを表
す。）で表されるシクロプロパンカルボン酸エステル誘
導体を含有する常温または加熱揮散性殺虫、防虫、忌避
剤、ならびにこれを用いた殺虫、防虫、忌避方法に係
る。Embedded image (In the formula, R represents fluorine, chlorine, or trifluoromethyl.) A normal-temperature or heated volatile insecticide, an insect repellent, a repellent, and an insecticide using the same containing a cyclopropanecarboxylate derivative represented by the formula: Related to insect repellent and repellent methods.
【０００５】[0005]
【作用】本発明において一般式Ｉを構成する酸部分（式
中、Ｒは、フッ素、塩素、トリフルオロメチルを表
す。）は既に公知であり、３−フェノキシベンジルアル
コール、５−ベンジル−３−フリルメチルアルコール等
との組み合わせで、イエバエ、チャバネゴキブリ等の衛
生害虫、ハスモンヨトウ、コナガ、アメリカシロヒトリ
等の農業害虫に対し高い殺虫活性を示すことが知られて
いるが、加熱蒸散用殺虫、防虫、忌避剤及び衣料用防虫
剤への適用を開示したものは全くない。しかるに本発明
者らは、一般式Ｉを構成するアルコールの揮散性に着目
し、これと前記酸部分との組み合わせを試験したとこ
ろ、一般式Ｉのピレスロイドが、実用化されている揮散
性ピレスロイドの特徴を保持し、本目的に適することを
知見した。In the present invention, the acid moiety constituting the general formula I (wherein R represents fluorine, chlorine or trifluoromethyl) is already known, and 3-phenoxybenzyl alcohol, 5-benzyl-3- It is known that in combination with furyl methyl alcohol, etc., it shows high insecticidal activity against sanitary pests such as house flies, German cockroaches, and agricultural pests such as Spodoptera litura, Japanese moth, and American white-throated pests. There are no disclosures of application to insecticides and clothing insect repellents. However, the present inventors focused on the volatility of the alcohol constituting the general formula I, and tested a combination of the alcohol and the acid moiety. As a result, the pyrethroid of the general formula I was converted to a volatile pyrethroid of a commercially available volatile pyrethroid. It has been found that it retains its features and is suitable for this purpose.
【０００６】本発明で有効成分として用いられる化合物
を例示すれば下記の如くである。 化合物１The following are examples of compounds used as active ingredients in the present invention. Compound 1
【化４】 ５−プロパルギル−２−フリルメチル ３−（２，３，
３，３−テトラフルオロ−１−プロペニル）−２，２−
ジメチルシクロプロパンカルボキシレート 化合物２Embedded image 5-propargyl-2-furylmethyl 3- (2,3,
3,3-tetrafluoro-1-propenyl) -2,2-
Dimethylcyclopropane carboxylate Compound 2
【化５】 ５−プロパルギル−２−フリルメチル ３−（２−クロ
ロ−３，３，３−トリフルオロ−１−プロペニル）−
２，２−ジメチルシクロプロパンカルボキシレー 化合物３Embedded image 5-propargyl-2-furylmethyl 3- (2-chloro-3,3,3-trifluoro-1-propenyl)-
2,2-dimethylcyclopropanecarboxylate Compound 3
【化６】 ５−プロパルギル−２−フリルメチル ３−〔３，３，
３−トリフルオロ−２−（トリフルオロメチル）−１−
プロペニル〕−２，２−ジメチルシクロプロパ Embedded image 5-propargyl-2-furylmethyl 3- [3,3
3-trifluoro-2- (trifluoromethyl) -1-
Propenyl] -2,2-dimethylcyclopropa
【０００７】上記化合物はエステル製造の一般方法に準
じて、次式ＩＩThe above compound is prepared by the following formula II according to a general method for producing an ester.
【化７】 （式中、Ｒは、フッ素、塩素、トリフルオロメチルを表
す。）で表されるカルボン酸又はその反応性誘導体と、
次式ＩＩＩEmbedded image (Wherein, R represents fluorine, chlorine or trifluoromethyl) or a reactive derivative thereof;
Formula III
【化８】 で表されるアルコール又はその反応性誘導体とを反応さ
せることにより調製できる。カルボン酸の反応性誘導体
としては、例えば酸ハライド、酸無水物、低級アルキル
エステル、アルカリ金属塩等があげられ、一方、アルコ
ールの反応性誘導体としては、例えばハライドがあげら
れる。反応は適当な溶媒中で、必要により脱酸剤又は触
媒としての有機又は無機塩基又は酸の存在下に必要によ
り加熱下に行われる。なお一般式Ｉの化合物において、
光学異性体が存在するが、それらの単独及び混合物、い
ずれも本発明に包含される。Embedded image By reacting with an alcohol represented by the formula or a reactive derivative thereof. Examples of the reactive derivative of a carboxylic acid include an acid halide, an acid anhydride, a lower alkyl ester, and an alkali metal salt. On the other hand, examples of the reactive derivative of an alcohol include a halide. The reaction is carried out in a suitable solvent, if necessary, in the presence of an organic or inorganic base or acid as a deoxidizing agent or a catalyst, optionally with heating. In the compound of the general formula I,
Although optical isomers exist, they alone and in mixtures are encompassed in the present invention.
【０００８】次に、本発明で用いられる化合物の合成例
を示す。Next, a synthesis example of the compound used in the present invention will be described.
【０００９】[0009]
【合成例】３−（２−クロロ−３，３，３−トリフルオ
ロ−１−プロペニル）−２，２−ジメチルシクロプロパ
ンカルボン酸 ０．５２ｇ，５−プロパルギル−２−フ
リルメタノール ０．３０ｇをジクロロメタンに溶解
し、ジシクロヘキシルカルボジイミド０．５１ｇ，Ｎ，
Ｎ−ジメチルアミノピリジン ０．１０ｇを加え、密栓
して室温で一晩放置した。析出した結晶をろ過し、ろ液
を濃縮して得られた油状物質をシリカゲルカラムクロマ
トグラフィーで分離し、５−プロパルギル−２−フリル
メチル３−（２−クロロ−３，３，３−トリフルオロ−
１−プロペニル）−２，２−ジメチルシクロプロパンカ
ルボキシレート（化合物２）０．３２ｇを得た。[Synthesis Example] 0.52 g of 3- (2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid and 0.30 g of 5-propargyl-2-furylmethanol Dissolve in dichloromethane and dicyclohexylcarbodiimide 0.51 g, N,
0.10 g of N-dimethylaminopyridine was added, sealed, and left at room temperature overnight. The precipitated crystals were filtered, the filtrate was concentrated, and the obtained oil was separated by silica gel column chromatography, and 5-propargyl-2-furylmethyl 3- (2-chloro-3,3,3-trifluoro −
0.32 g of (1-propenyl) -2,2-dimethylcyclopropanecarboxylate (compound 2) was obtained.
【００１０】本発明の化合物は常温で液体であり、有機
溶剤一般に易溶である。これらの化合物は、従来のピレ
スロイドに比べて揮散性が高く、低濃度では忌避効果も
発揮するため、常温及び加熱下で使用する殺虫、防虫、
忌避剤として有用であり、衣料害虫をはじめハエ、蚊、
ゴキブリ、屋内塵性ダニ類などに対して幅広い適用が期
待されるものである。本発明の殺虫、防虫、忌避剤は前
記有効成分化合物をそのまま使用することも可能である
が、通常好ましくは適当な担体、その他の賦形剤を用い
て、例えば、粉末、錠剤、マット、シート状等の固剤形
態又は乳剤、噴霧剤、エアゾール剤の液剤形態に調製
し、これら各形態に応じた方法により害虫の防除に適用
される。The compounds of the present invention are liquid at room temperature and are generally readily soluble in organic solvents. These compounds have a higher volatility than conventional pyrethroids, and also exhibit a repellent effect at a low concentration, so that insecticides and insect repellents used at room temperature and under heating can be used.
It is useful as a repellent, and it includes clothing pests, flies, mosquitoes,
It is expected to be widely applied to cockroaches and indoor dust mites. The insecticide, insect repellent and repellent of the present invention can use the active ingredient compound as it is, but usually preferably using a suitable carrier and other excipients, for example, powder, tablets, mats and sheets It is prepared in the form of a solid preparation in the form of a liquid or in the form of a liquid such as an emulsion, a spray, or an aerosol, and is applied to the control of pests by a method according to each of these forms.
【００１１】固剤の形態に調製するにあたり用いられる
担体としては、代表的には例えばケイ酸、カオリン、タ
ルク等の各種鉱物質粉末や、木粉、小麦粉などの各種植
物質粉末などを例示できる。なお、アダマンタン、シク
ロドデカン、トリイソプロピル−トリオキサン等の昇華
性担体を用いて本発明化合物の揮散性調節を図ることも
でき、また、ポリビニルアルコール、アルギン酸、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、マット、シート状の基材としては、
パルプ製マット、紙、織布、不織布あるいはポリエチレ
ン、ポリプロピレン、ポリ塩化ビニル、ポリエステル、
エチレン酢酸ビニール等のプラスチック成形品、多孔性
ガラス材料等をあげることができる。[0011] The carrier used in the preparation of a solid preparation can be typically exemplified by various mineral powders such as silicic acid, kaolin and talc, and various plant powders such as wood flour and wheat flour. . The volatility of the compound of the present invention can be controlled by using a sublimable carrier such as adamantane, cyclododecane, and triisopropyl-trioxane.Also, a gel can be formed by using a gelling agent such as polyvinyl alcohol, alginic acid, and carrageenan. It can also be prepared in form. Further, as a mat or sheet-like base material,
Pulp mat, paper, woven fabric, non-woven fabric or polyethylene, polypropylene, polyvinyl chloride, polyester,
Plastic molded articles such as ethylene vinyl acetate, porous glass materials, and the like can be given.
【００１２】また、本発明の化合物にＮ−オクチルビシ
クロヘプテンジカルボキシイミド（商品名ＭＧＫ−２６
４）、Ｎ−オクチルビシクロヘプテンジカルボキシイミ
ドとアリールスルホン酸塩との混合物（商品名ＭＧＫ−
５０２６）、サイネピリン５００、オクタクロロジプロ
ピルエーテル、ピペロニルブトキサイドなどの共力剤を
加えても良い。The compound of the present invention may be added to N-octylbicycloheptenedicarboximide (trade name: MGK-26).
4), a mixture of N-octylbicycloheptenedicarboximide and an aryl sulfonate (trade name: MGK-
5026), a synergist such as sinepirin 500, octachlorodipropyl ether, piperonyl butoxide may be added.
【００１３】また、他の殺虫剤、例えばフェニトロチオ
ン、ＤＤＶＰ、ダイアジノン等の有機リン剤、ＮＡＣ、
ＭＴＭＣ、ＢＰＭＣ、ＰＨＣ等のカーバメート剤、ピレ
トリン、アレスリン、フタールスリン、フェノトリン、
ペルメトリン、エムペントリン等の従来のピレスロイド
系殺虫剤あるいは芳香剤、防臭剤、殺菌剤等を混合する
ことによって効力のすぐれた多目的組成物が得られ、労
力の省力化、薬剤間の相乗効果も十分期待しえるもので
ある。Also, other insecticides such as organophosphorus agents such as fenitrothion, DDVP and diazinon, NAC,
MTMC, BPMC, carbamates such as PHC, pyrethrin, allethrin, phthalthrine, phenothrin,
By mixing conventional pyrethroid insecticides such as permethrin and empentrin, or fragrances, deodorants, bactericides, etc., a multipurpose composition with excellent efficacy can be obtained, labor savings and a synergistic effect between drugs are also expected. It can be done.
【００１４】こうして得られた本発明の常温又は加熱揮
散性殺虫、防虫、忌避剤は、タンス、衣裳箱等の衣類収
納家具に適用して、イガ、コイガ、ヒメカツオブシム
シ、ヒメマルカツオブシムシ等の衣料害虫に高い駆除効
果を奏するほか、適当な加熱器具を用いた、ハエ、蚊等
の防除にも極めて有用なものである。例えば、発熱体と
して無機もしくは有機の正特性サーミスタを用いて、５
０−１００°Ｃ程度に加熱することにより、本発明化合
物の殺虫、防虫、忌避効力を一層高めることができる。The room temperature or heated volatile insecticide, insect repellent and repellent of the present invention thus obtained are applied to clothing storage furniture such as a closet and a clothing box, and are applied to clothing pests such as Iga, Koiga, Himematsu-obushi, Himemaruka-obushi, etc. In addition to its high control effect, it is extremely useful for controlling flies, mosquitoes and the like using an appropriate heating device. For example, using an inorganic or organic PTC thermistor as a heating element,
By heating to about 0-100 ° C, the insecticidal, insect repellent and repellent effects of the compound of the present invention can be further enhanced.
【００１５】本発明によって提供される製剤がすぐれた
ものであることをより明らかにするため次に実施例及び
効果の試験成績を示す。In order to further clarify that the preparations provided by the present invention are excellent, the following examples and test results of the effects are shown.
【００１６】[0016]
【実施例１】本発明の化合物（１）０．３ｇ、香料０．
０１ｇを、厚さ１ｍｍ、縦６０ｍｍ、横８０ｍｍの厚紙
シートに浸み込ませて衣料用防虫マットを得た。Example 1 0.3 g of the compound (1) of the present invention and 0.1% of a fragrance were added.
01 g was impregnated into a cardboard sheet having a thickness of 1 mm, a length of 60 mm and a width of 80 mm to obtain an insect repellent mat for clothing.
【００１７】[0017]
【実施例２】本発明の化合物（２）０．４ｇ、ＭＧＫ−
５０２６ １．０部を除虫菊抽出粕粉、木粉、デン粉等
の蚊取線香用基材９８．６部に均一に混合し公知の方法
によって蚊取線香を得た。Example 2 0.4 g of compound (2) of the present invention, MGK-
5026 1.0 part was uniformly mixed with 98.6 parts of a mosquito coil base material such as pyrethrum extract meal powder, wood flour, and starch powder to obtain a mosquito coil by a known method.
【００１８】[0018]
【実施例３】本発明の化合物（３）０．２５ｇにケロシ
ンを加えて１００ｍｌとした溶液を耐圧容器に入れ、液
化石油ガス、ジメチルエーテルの混合ガス２００ｍｌを
加え、噴射バルブを取り付けて殺虫、防虫エアゾールを
得た。Example 3 A solution prepared by adding kerosene to 0.25 g of the compound (3) of the present invention to make 100 ml was placed in a pressure vessel, and 200 ml of a mixed gas of liquefied petroleum gas and dimethyl ether was added. An aerosol was obtained.
【００１９】[0019]
【実施例４】本発明の化合物（１）１部及び適量の香料
の混合物に灯油を加えて１００部とし、よくかく拌混合
して加熱蒸散用殺虫、防虫液を得た。Example 4 Kerosene was added to a mixture of 1 part of the compound (1) of the present invention and an appropriate amount of a fragrance to make 100 parts, and the mixture was thoroughly stirred and mixed to obtain an insecticidal and insect repellent for heat evaporation.
【００２０】[0020]
【試験例１】 燻蒸による殺虫試験 実施例２に準じ、殺虫成分として供試化合物０．５％を
含む蚊取線香を作り、アカイエカの成虫を落下仰転せし
める効果を試験した。この実験は、防虫科学１６巻（１
９５１年）第１７６頁、長沢、勝田等の方法に従い前記
線香の相対有効度を算出したところ、表１の如くであっ
た。Test Example 1 Insecticidal Test by Fumigation In accordance with Example 2, a mosquito coil containing 0.5% of a test compound as an insecticidal component was prepared, and the effect of turning a Culex pipiens offspring was tested. In this experiment, insect repellent science volume 16 (1
951) Page 176, the relative effectiveness of the incense stick was calculated according to the method of Nagasawa, Katsuta et al.
【００２１】[0021]
【表１】 [Table 1]
【００２２】試験の結果、本発明化合物を含有する蚊取
線香は、アカイエカ成虫に対して高い殺虫効果を示し、
市販のアレスリンよりすぐれた効果を示した。As a result of the test, the mosquito coil containing the compound of the present invention shows a high insecticidal effect on adult Culex pipiens
The effect was superior to that of commercial allresulin.
【００２３】[0023]
【試験例２】 蒸散による実用試験 実施例１により調製した衣料用防虫マットをプラスチッ
クケースに収納し、容積６００ｌのタンス内につるし
た。試験開始直後及び６ヶ月後に、イガの１令幼虫１０
匹を放飼した直径４ｃｍ、幅２ｃｍのガラスリング（両
面を羊毛布でカバー）をタンス内に設置し、１日後、２
日後、７日後の死虫率を観察したところ表２の如くであ
った。Test Example 2 Practical test by transpiration The insect repellent mat for clothing prepared in Example 1 was housed in a plastic case, and suspended in a 600-liter closet. Immediately after the start of the test and 6 months later, the first instar larva of iga 10
A glass ring of 4 cm in diameter and 2 cm in width (covered on both sides with a wool cloth) in which the animals were released was placed in a closet.
After 2 days and 7 days, the mortality was observed, as shown in Table 2.
【００２４】[0024]
【表２】 上記表２中、対照化合物Ａは、次式（Ａ）[Table 2] In the above Table 2, the control compound A is represented by the following formula (A)
【化９】 で表されるピレスロイドである。Embedded image It is a pyrethroid represented by
【００２５】試験の結果、本発明化合物は、衣料害虫の
イガ幼虫に対して対照化合物Ａにまさる殺虫、防虫効果
を示し、その揮散性と効力が衣料用殺虫、防虫剤として
最適であることが確認された。ヒメカツオブシムシ、ヒ
メマルカツオブシムシ、コイガ、ジュウタンガ等の他の
衣料害虫に対しても同様に有効であった。なお、本発明
化合物の類縁体であっても、対照化合物Ａのように、シ
クロプロパン環側鎖が臭素原子で置換されているもの
は、蒸散性が悪く、揮散性を加味した殺虫、防虫効力
は、本発明化合物に特有のものであることも明らかとな
った。As a result of the test, the compound of the present invention showed an insecticidal and insect repellent effect more than the control compound A against the harmful larva of the insect pest of clothing, and its volatility and efficacy were most suitable as insecticides and insect repellents for clothing. confirmed. It was similarly effective against other clothing pests such as burrowing beetle, burdock beetle, kioga, and jutanga. In addition, even if it is an analog of the compound of the present invention, the compound in which the cyclopropane ring side chain is substituted with a bromine atom, such as the control compound A, has a poor transpiration property and has an insecticidal and insecticidal effect in consideration of volatility. Was also found to be unique to the compound of the present invention.
【００２６】[0026]
【発明の効果】本発明で用いられる一般式Ｉで表される
化合物は、常温または加熱揮散性を有し、高い殺虫、防
虫、忌避効果、温血動物に対する低毒性、ならびに化学
的安定性等を兼備した常温または加熱揮散性殺虫、防
虫、忌避剤、ならびにこれを用いた殺虫、防虫、忌避方
法を提供する。The compound represented by the general formula I used in the present invention has room temperature or heat volatility, high insecticidal, insect repellent, repellent effects, low toxicity to warm-blooded animals, chemical stability and the like. Provided are an insecticide, an insect repellent, and a repellent which are normal temperature or heat volatile and have an insecticide, insect repellent, and repellent method using the same.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭55−89248（ＪＰ，Ａ) 特開 昭54−130537（ＪＰ，Ａ) 特開 昭49−445（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) A01N 53/04 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continuation of the front page (56) References JP-A-55-89248 (JP, A) JP-A-54-130537 (JP, A) JP-A-49-445 (JP, A) (58) Field (Int.Cl. 7 , DB name) A01N 53/04 CA (STN) REGISTRY (STN)
Claims (2)
す。）で表されるシクロプロパンカルボン酸エステル誘
導体を含有することを特徴とする常温または加熱揮散性
殺虫、防虫、忌避剤。1. A compound of the general formula I (In the formula, R represents fluorine, chlorine, or trifluoromethyl.) An insecticide, insect repellent or repellent which is volatile at normal temperature or under heating, comprising a cyclopropanecarboxylic acid ester derivative represented by the following formula:
す。）で表されるシクロプロパンカルボン酸エステル誘
導体を常温または加熱により揮散させることを特徴とす
る殺虫、防虫、忌避方法。2. A compound of the general formula I (In the formula, R represents fluorine, chlorine or trifluoromethyl.) A method for killing insects, controlling insects, and repelling, comprising subjecting a cyclopropanecarboxylate derivative represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03392293A JP3189917B2 (en) | 1993-01-11 | 1993-01-11 | An insecticide, insect repellent and repellent containing a cyclopropanecarboxylic acid ester derivative, and an insecticide, insect repellent and repellent method using the same. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03392293A JP3189917B2 (en) | 1993-01-11 | 1993-01-11 | An insecticide, insect repellent and repellent containing a cyclopropanecarboxylic acid ester derivative, and an insecticide, insect repellent and repellent method using the same. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06211611A JPH06211611A (en) | 1994-08-02 |
| JP3189917B2 true JP3189917B2 (en) | 2001-07-16 |
Family
ID=12400017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP03392293A Expired - Lifetime JP3189917B2 (en) | 1993-01-11 | 1993-01-11 | An insecticide, insect repellent and repellent containing a cyclopropanecarboxylic acid ester derivative, and an insecticide, insect repellent and repellent method using the same. |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3189917B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048892A (en) * | 1997-12-30 | 2000-04-11 | Sumitomo Chemical Company, Limited | Ester compound pesticide containing thereof |
| AU753585B2 (en) * | 1998-09-15 | 2002-10-24 | Sumitomo Chemical Company, Limited | Ester compound and pesticide containing thereof |
| US7651974B2 (en) | 2002-11-01 | 2010-01-26 | Kureha Chemical Industry Co., Ltd. | Adsorbent for oral administration |
| JP2010106007A (en) | 2008-08-14 | 2010-05-13 | Sony Corp | Drug sustained-release agent, adsorbent, functional food, mask and adhesive sheet |
-
1993
- 1993-01-11 JP JP03392293A patent/JP3189917B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06211611A (en) | 1994-08-02 |
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