JPH0796481B2 - Insecticide, acaricide - Google Patents
Insecticide, acaricideInfo
- Publication number
- JPH0796481B2 JPH0796481B2 JP17533389A JP17533389A JPH0796481B2 JP H0796481 B2 JPH0796481 B2 JP H0796481B2 JP 17533389 A JP17533389 A JP 17533389A JP 17533389 A JP17533389 A JP 17533389A JP H0796481 B2 JPH0796481 B2 JP H0796481B2
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- weight
- methyl
- present
- nonenyl
- acetoxyquinoline
- Prior art date
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規物質である2,3−ジ置換−４−ヒドロキシ
キノリン誘導体を有効成分とする極めて優れた殺虫、殺
ダニ効果を有する殺虫、殺ダニ剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention is a novel substance, which is a 2,3-disubstituted-4-hydroxyquinoline derivative as an active ingredient. Regarding acaricide.
従来、各種の天然成分及び合成物質の殺虫、殺ダニ活性
を有する物質が研究、開発され実用に供せられている。
またキノリン系物質としては、３−ｐ−ブロモフェニル
−１−ｏ−ヒドロキシスチリルベンゾ［ｆ］キノリンに
殺ダニ活性、殺カビ活性のあることが知られている〔Ve
stsi Akad.Navuk BSSR,Ser.Khim.Navuk.（３）,76−８
（1987）〕。Conventionally, various natural components and synthetic substances having insecticidal and acaricidal activity have been researched, developed and put into practical use.
As a quinoline-based substance, 3-p-bromophenyl-1-o-hydroxystyrylbenzo [f] quinoline is known to have acaricidal activity and fungicidal activity [Ve
stsi Akad.Navuk BSSR, Ser.Khim.Navuk. (3), 76-8
(1987)].
また、８−アルコキシキノリン類の銅錯体を活性成分と
する殺菌・殺虫剤も知られている（特公昭54−34738号
公報）。しかしながら、これらの化合物の殺虫活性はそ
の強さ、選択性等の点で十分なものではない。Further, a bactericidal / insecticide containing a copper complex of 8-alkoxyquinolines as an active ingredient is also known (Japanese Patent Publication No. 54-34738). However, the insecticidal activity of these compounds is not sufficient in terms of their strength and selectivity.
従来公知の殺虫、殺ダニ活性を有する各種物質も、近年
殺虫剤抵抗性の問題によりその活性効力も十分とは言え
ず、優れた活性を有する新規殺虫、殺ダニ剤の開発が要
望されている。Conventionally known insecticides, various substances having acaricidal activity, the activity efficacy is not sufficient due to the problem of insecticide resistance in recent years, and the development of new insecticides and acaricides having excellent activity has been demanded. .
本発明はこの要望にこたえた優れた殺虫、殺ダニ剤を提
供することを目的とするものである。It is an object of the present invention to provide an excellent insecticidal and acaricidal agent that meets this need.
本発明者らは先に、微生物代謝産物及びその類縁体を純
化学的に合成し、強いロイコトリエンD4拮抗作用を有
し、ヒトを含む哺乳類の生体維持特に重要な免疫系と心
臓血流に有効に作用し、免疫疾患並びに脳疾患の治療に
有効な物質である新規2,3−ジ置換−４−ヒドロキシキ
ノリン誘導体及びその製造法を発明し、特願昭63−3192
31号として出願した。The present inventors have previously chemically synthesized microbial metabolites and their analogs, have a strong leukotriene D 4 antagonism, and maintain the living body of mammals including humans, especially for the important immune system and cardiac blood flow. A novel 2,3-disubstituted-4-hydroxyquinoline derivative which is an effective substance for treating immune diseases and brain diseases and a method for producing the same are invented, and Japanese Patent Application No. 63-3192.
Filed as No. 31
本発明者らは更に、この物質の作用を研究したところ、
殺虫、殺ダニ活性が優れていることを見出し、本発明を
完成した。The present inventors further studied the action of this substance,
The inventors have found that the insecticidal and acaricidal activities are excellent and completed the present invention.
本発明は一般式（Ｉ） 〔式中R1は水素原子又はR3CO−（R3は低級アルキル基を
示す）を示し、R2は水素原子、メチル基又はエチル基を
示し、Ａは で表される2,3−ジ置換−４−ヒドロキシキノリン誘導
体の１種又は２種以上を有効成分とする殺虫、殺ダニ剤
である。The present invention has the general formula (I) [Wherein R 1 represents a hydrogen atom or R 3 CO— (R 3 represents a lower alkyl group), R 2 represents a hydrogen atom, a methyl group or an ethyl group, and A represents The insecticide and acaricide having one or more of 2,3-disubstituted-4-hydroxyquinoline derivatives represented by the following as an active ingredient.
本発明の有効成分である上記式（Ｉ）で表される化合物
は、同式中のR1が水素原子を示す場合は式（II）で表さ
れる2,3−ジ置換−４−キノロン誘導体とは互変異性の
関係にあるが、本化合物も本発明に含まれる。The compound represented by the above formula (I) which is the active ingredient of the present invention is a 2,3-disubstituted-4-quinolone represented by the formula (II) when R 1 in the formula is a hydrogen atom. Although it has a tautomeric relationship with the derivative, the present compound also falls within the scope of the present invention.
〔式中、R2,Aは先と同一意義を有する〕 本発明の有効成分である2,3−ジ置換−４−ヒドロキシ
キノリン誘導体は全て文献未載の新規化合物である。そ
の代表的な化合物を以下に挙げる。 [Wherein R 2 and A have the same meanings as above] The 2,3-disubstituted-4-hydroxyquinoline derivatives, which are the active ingredients of the present invention, are all novel compounds which have not been published in the literature. The typical compounds are listed below.
1.2−（トランス−１−ノネニル）−３−メチル−４−
アセトキシキノリン 2.2−（シス−１−ノネニル）−３−メチル−４−アセ
トキシキノリン 3.2−（トランス−１−ノネニル）−３−メチル−４−
キノロン 4.2−（シス−１−ノネニル）−３−メチル−４−キノ
ロン 5.2−（トランス−２−ノネニル）−３−メチル−４−
アセトキシキノリン 6.2−（トランス−２−ノネニル）−３−メチル−４−
キノロン 7.2−（１−ヒドロキシ−２−ノニニル）−３−メチル
−４−アセトキシキノリン 8.2−（１−ヒドロキシ−２−ノニニル）−３−メチル
−４−キノロン 9.2−（トランス−１−ヒドロキシ−２−ノネニル）−
３−メチル−４−アセトキシキノリン 10.2−（トランス−１−ヒドロキシ−２−ノネニル）−
３−メチル−４−キノロン 等である。1.2- (trans-1-nonenyl) -3-methyl-4-
Acetoxyquinoline 2.2- (cis-1-nonenyl) -3-methyl-4-acetoxyquinoline 3.2- (trans-1-nonenyl) -3-methyl-4-
Quinolone 4.2- (cis-1-nonenyl) -3-methyl-4-quinolone 5.2- (trans-2-nonenyl) -3-methyl-4-
Acetoxyquinoline 6.2- (trans-2-nonenyl) -3-methyl-4-
Quinolone 7.2- (1-Hydroxy-2-nonynyl) -3-methyl-4-acetoxyquinoline 8.2- (1-Hydroxy-2-nonynyl) -3-methyl-4-quinolone 9.2- (trans-1-hydroxy-2 -Nonenyl)-
3-Methyl-4-acetoxyquinoline 10.2- (trans-1-hydroxy-2-nonenyl)-
3-methyl-4-quinolone and the like.
なお、本化合物名に付した番号は、下記の実施例におい
て引用される。The numbers given to the names of the compounds are cited in the examples below.
本発明の上記の一般式（Ｉ）で表した2,3−ジ置換−４
−ヒドロキシキノリン誘導体を有効成分とした殺虫剤
は、アブラムシ類，ウンカ類，ヨコバイ類，カメムシ類
等の半翅目、ハスモンヨトウ，コナガ，ニカメイガ等の
鱗翅目、ゾウムシ類、ハムシ類等の鞘翅目、イエバエ，
アカイエカ等の双翅目、ゴキブリ類等の網翅目その他直
翅目、アザミウマ目等の昆虫及びハダニ類，マダニ類，
ネダニ類等の害虫、ダニ類に特に顕著な活性を有するも
のである。2,3-disubstituted-4 represented by the above general formula (I) of the present invention
-Insecticides containing a hydroxyquinoline derivative as an active ingredient include hemiptera of aphids, planthoppers, leafhoppers, stink bugs, etc., Lepidoptera of Spodoptera litura, Kokonaga, Nikameiga etc., Coleoptera of weevils, Chrysomelidae, etc., Housefly,
Diptera, such as Culex pipiens, reticules, such as cockroaches, other orthoptera, insects such as Thrips, and spider mites, ticks,
It has a particularly remarkable activity against pests such as mite and mites.
本発明の殺虫、殺ダニ剤は、有効成分として前記一般式
（Ｉ）で表される化合物の１種又は２種以上を、そのま
ま用いてもよいが、通常は一般に農薬の製剤に使用され
る固体担体、液体担体、ガス状担体、界面活性剤、分散
剤その他製剤用補助剤、餌等と通常の方法により混合
し、乳剤、液剤、水和剤、粉剤、粒剤、油剤、エアゾー
ル剤、フロワブル剤、毒餌等の適宜の剤形にして使用す
る。In the insecticidal and acaricidal agent of the present invention, one or more compounds represented by the general formula (I) may be used as they are as an active ingredient, but they are generally used for the preparation of agricultural chemicals. Solid carriers, liquid carriers, gaseous carriers, surfactants, dispersants, other auxiliary agents for formulation, baits and the like are mixed by a usual method, and emulsions, liquids, wettable powders, powders, granules, oils, aerosols, Use it in a suitable dosage form such as a flowable agent or poison bait.
なお、固体担体としては、例えばタルク，ベントナト，
クレー，カオリン，ケイソウ土，バーミキュライト，ホ
ワイトカーボン，炭酸カルシウム等が挙げられ、液体担
体としては、例えばメタノール,n−ヘキサノール，エチ
レングリコール，セロソルブ等のアルコール類、アセト
ン，メチルエチルケトン，シクロヘキサノン等のケトン
類、ケロシン，灯油等の脂肪族炭化水素類、ベンゼン，
トルエン，キシレン，メチルナフタレン等の芳香族炭化
水素類、ジクロロエタン，トリクロロエチレン，四塩化
炭素等のハロゲン化炭化水素類、ジエチルエーテル，ジ
オキサン，テトラヒドロフラン等のエーテル類、酢酸エ
チル等のエステル類、アセトニトリル，イソブチロニト
リル等のニトリル類、ジメチルホルムアミド，ジメチル
アセトアミド等の酸アミド類、大豆油，綿実油等の植物
油類、ジメチルスルホキシド、水等が挙げられる。ガス
担体としては、例えばLPG,フロンガス，空気，窒素，炭
素ガス，ジメチルエーテル等が挙げられる。Examples of solid carriers include talc, bentonat,
Examples thereof include clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, and the like. Examples of liquid carriers include alcohols such as methanol, n-hexanol, ethylene glycol, and cellosolve, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, Kerosene, aliphatic hydrocarbons such as kerosene, benzene,
Aromatic hydrocarbons such as toluene, xylene and methylnaphthalene, halogenated hydrocarbons such as dichloroethane, trichloroethylene and carbon tetrachloride, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, acetonitrile, iso Examples thereof include nitriles such as butyronitrile, acid amides such as dimethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, and water. Examples of the gas carrier include LPG, CFC gas, air, nitrogen, carbon gas, dimethyl ether and the like.
乳化、分散、展着等のための界面活性剤、分散剤として
は、例えばアルキル硫酸エステル類、アルキル（アリー
ル）スルホン酸塩類、ポリオキシアルキレンアルキル
（アリール）エーテル類、多価アルコールエステル類、
リグニンスルホン酸塩等が用いられる。Examples of surfactants and dispersants for emulsification, dispersion, spreading and the like include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters,
Lignin sulfonate or the like is used.
更に、製剤の性状を改善するための補助剤としては、例
えばカルボキシメチルセルロース，アラビアガム，ポリ
エチレングリコール，ステアリン酸カルシウム等が用い
られる。Further, as an auxiliary agent for improving the properties of the preparation, for example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate, etc. are used.
上記の担体、界面活性剤、分散剤及び補助剤は、必要に
応じて各々単独或いは組み合わせて用いられる。The above carrier, surfactant, dispersant and auxiliary agent may be used alone or in combination as necessary.
本発明における殺虫、殺ダニ剤の有効成分の含有量は、
乳剤では通常、１〜50重量％、粉剤では通常、0.3〜25
重量％、水和剤では通常１〜90重量％、粒剤では通常、
0.5〜10重量％が適当である。Insecticide in the present invention, the content of active ingredients of acaricide,
Emulsion is usually 1 to 50% by weight, powder is usually 0.3 to 25% by weight.
% By weight, usually 1 to 90% by weight for wettable powders, usually for granules,
0.5 to 10% by weight is suitable.
これらの製剤は、そのまま或いは希釈して用いる。ま
た、他の殺虫剤、殺ダニ剤、殺菌剤、除草剤、植物成長
調節剤、肥料、土壌改良剤、共力剤等と混合して使用す
ることもできる。These formulations are used as they are or after being diluted. Further, it can be used as a mixture with other insecticides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, synergists and the like.
次に本発明の実施例並びにその効果を挙げ、本発明を更
に詳細に説明するが、本発明はこれらの実施例のみに限
定されるものではない。Next, the present invention will be described in more detail with reference to examples and effects of the present invention, but the present invention is not limited to these examples.
製造例１ 化合物１並びに２の製造例 オクチルトリフェニルホスホニウムブロマイド218mg
（0.48mmol）のテトラヒドロフラン3ml溶液にｎ−ブチ
ルリチウム0.48mmolのヘキサン溶液0.29mlを加え、室温
で５分間撹拌する。Production Example 1 Production Example of Compounds 1 and 2 Octyltriphenylphosphonium bromide 218 mg
0.29 ml of a hexane solution of 0.48 mmol of n-butyllithium is added to a 3 ml solution of (0.48 mmol) of tetrahydrofuran, and the mixture is stirred at room temperature for 5 minutes.
この溶液を−78℃に冷却した後、ヘキサメチルホスホラ
ストリアミド1.43g（8mmol）を加え５分間撹拌し、更に
２−ホルミル−３−メチル−４−アセトキシキノリン9
1.6mg（0.40mmol）のテトラヒドロフラン2ml溶液を加え
て、−78℃で15分間、−42℃で30分間撹拌する。反応液
を水20mlに加え、酢酸エチルで抽出し、飽和塩化ナトリ
ウム水溶液で洗浄した後、無水硫酸ナトリウム上で乾燥
した。溶媒を減圧留去した後、シリカゲルカラムクロマ
トグラフィー〔ワコーゲルＣ−200（和光純薬製）（溶
媒ｎ−ヘキサン：酢酸エチル＝15:1）〕により精製する
と、２−（トランス−１−ノネニル）−３−メチル−４
−アセトキシキノリン13mg（収率10％）及び２−（シス
−１−ノネニル）−３−メチル−４−アセトキシキノリ
ン15mg（収率12％）が得られる。After cooling this solution to −78 ° C., 1.43 g (8 mmol) of hexamethylphosphorus triamide was added and stirred for 5 minutes, and further 2-formyl-3-methyl-4-acetoxyquinoline 9
A solution of 1.6 mg (0.40 mmol) of tetrahydrofuran in 2 ml is added, and the mixture is stirred at -78 ° C for 15 minutes and at -42 ° C for 30 minutes. The reaction solution was added to 20 ml of water, extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography [Wakogel C-200 (Wako Pure Chemical Industries, Ltd.) (solvent n-hexane: ethyl acetate = 15: 1)] to give 2- (trans-1-nonenyl). -3-methyl-4
13 mg of acetoxyquinoline (10% yield) and 15 mg of 2- (cis-1-nonenyl) -3-methyl-4-acetoxyquinoline (12% yield) are obtained.
２−（トランス−１−ノネニル）−３−メチル−４−ア
セトキシキノリン〔化合物１〕 融点 74〜75℃ NMR（CDCl3） δ＝0.90（t,J＝7Hz,3H） 1.2〜1.5（m,10H）,2.31（s,3H）， 2.33〜2.40（m,2H）,2.51（s,3H）， 6.80（d,J＝15.4Hz,1H）， 7.08（dt,J＝15.4Hz,J＝7.1Hz,1H）， 7.4〜7.8（m,3H）,8.04（d,J＝8.8Hz,1H） ２−（シス−１−ノネニル）−３−メチル−４−アセト
キシキノリン〔化合物２〕 NMR（CDCl3） δ＝0.84（t,J＝6Hz 3H 1.1〜1.6（m,10H）， 2.2〜2.7（m,2H）,2.26（s,3H）， 2.49（s,3H）,6.02（dt,J＝12Hz,J＝7Hz,1H）， 6.61（d,J＝12Hz,1H）， 7.3〜8.1（m,4H） 実施例１ 乳剤 化合物１ 20重量％、N,N−ジメチルホルムアミド20重
量％、キシレン50重量％にポリオキシエチレンアルキル
アリルエーテル10重量％を加え均一に混合し、溶解して
乳剤を得た。2- (trans-1-nonenyl) -3-methyl-4-acetoxyquinoline [Compound 1] Melting point 74-75 ° C NMR (CDCl 3 ) δ = 0.90 (t, J = 7Hz, 3H) 1.2-1.5 (m, 10H), 2.31 (s, 3H), 2.33 to 2.40 (m, 2H), 2.51 (s, 3H), 6.80 (d, J = 15.4Hz, 1H), 7.08 (dt, J = 15.4Hz, J = 7.1) Hz, 1H), 7.4 to 7.8 (m, 3H), 8.04 (d, J = 8.8Hz, 1H) 2- (cis-1-nonenyl) -3-methyl-4-acetoxyquinoline [compound 2] NMR (CDCl 3 ) δ = 0.84 (t, J = 6Hz 3H 1.1 to 1.6 (m, 10H), 2.2 to 2.7 (m, 2H), 2.26 (s, 3H), 2.49 (s, 3H), 6.02 (dt, J = 12Hz, J = 7Hz, 1H), 6.61 (d, J = 12Hz, 1H), 7.3 ~ 8.1 (m, 4H) Example 1 Emulsion compound 1 20% by weight, N, N-dimethylformamide 20% by weight, xylene 50 10% by weight of polyoxyethylene alkylallyl ether was added to the weight% and mixed uniformly and dissolved to obtain an emulsion.
実施例２ 水和剤 化合物２ 25重量％、クレー30重量％、ケイソウ土35重
量％、リグニンスルホン酸カルシウム３重量％、ポリオ
キシエチレンアルキルアリルエーテル７重量％を均一に
混合し、粉砕して水和剤を得た。Example 2 Wettable powder 25% by weight of compound 2, 30% by weight of clay, 35% by weight of diatomaceous earth, 3% by weight of calcium lignin sulfonate, 7% by weight of polyoxyethylene alkylallyl ether were uniformly mixed and pulverized to obtain water. I got a Japanese medicine.
実施例３ 粉剤 化合物１ ２重量％、クレー60重量％、タルク37重量
％、ステアリン酸カルシウム１重量％を均一に混合して
粉剤を得た。Example 3 Powder Dust was obtained by uniformly mixing 2% by weight of compound 1, 60% by weight of clay, 37% by weight of talc, and 1% by weight of calcium stearate.
実施例４ 粒剤 化合物２ ５重量％、ベントナイト40重量％、タルク53
重量％、リグニンスルホン酸カルシウム２重量％を均一
に粉砕混合し、水を加えてよく練合した後、造粒乾燥し
て粒剤を得た。Example 4 Granules Compound 2 5% by weight, bentonite 40% by weight, talc 53
% By weight and 2% by weight of calcium ligninsulfonate were uniformly pulverized and mixed, water was added thereto and kneaded well, and then granulated and dried to obtain granules.
次に本発明の殺虫、殺ダニ剤の効果を示す試験並びに結
果を示す。Next, the tests and results showing the effects of the insecticidal and acaricidal agents of the present invention are shown.
試験例１ モモアカブラシム（無翅胎生雌成虫）に対す
る効力試験 実施例１に準じて製剤した供試試料を、界面活性剤（0.
01％）を含む水で1000ppmに希釈した供試液に、モモア
カアブラムシ無翅胎生雌成虫10頭を接種したキャベツ葉
片（5cm×5cm）を10秒間浸漬した。風乾後、直径9cmの
プラスチックカップに入れ、25℃の恒温室に放置し、１
日後の生死虫数を調査し、死虫率を求めた。Test Example 1 Efficacy test against peach mosquito (wingless fetus adult) A test sample prepared according to Example 1 was treated with a surfactant (0.
Cabbage leaf pieces (5 cm x 5 cm) inoculated with 10 adult female peach aphid wingless female embryos were immersed in a test solution diluted to 1000 ppm with water containing 01%) for 10 seconds. After air-drying, put it in a plastic cup with a diameter of 9 cm and leave it in a constant temperature room at 25 ° C.
The number of live and dead insects after the day was investigated and the mortality rate was calculated.
その結果は第１表の通りであった。The results are shown in Table 1.
試験例２ ニセナミハダニ雌成虫（有機リン剤抵抗性）
に対する効力試験 直径6cmのプラスチックポットに栽培したツルナシイン
ゲン初生葉に、ニセナミハダニ雌成虫10頭を接種した。
これに接種１日後に実施例１に準じて製剤した供試々料
を界面活性剤（0.01％）を含む水で1000ppmに希釈した
供試液を、噴霧塔で10ml散布した。処理後25℃の恒温室
に放置し、２日後の生死虫数を調査し、死虫率を求め
た。 Test Example 2 Adult female mites of the spider mites (organic phosphorus drug resistance)
Efficacy test against cultivated 6-cm diameter plastic pot cultivated primary leaves of Phellinus linteus were inoculated with 10 adult females of the spider mite mite.
One day after the inoculation, the test solution prepared according to Example 1 was diluted to 1000 ppm with water containing a surfactant (0.01%), and 10 ml of the test solution was sprayed in a spray tower. After the treatment, the sample was left in a thermostatic chamber at 25 ° C., and the number of live and dead insects was investigated 2 days later to determine the mortality rate.
その結果は第２表の通りであった。The results are shown in Table 2.
試験例３ カイコ３令幼虫に対する殺虫試験 実施例１に準じて製剤した供死試料を水で希釈して400p
pmの濃度の薬液100mlを調製した。この薬液の中に蚕用
乾燥人工飼料（協同飼料株式会社製家蚕用ビタシルク）
を浸漬し、充分に含浸させた。この人工飼料を直径9cm
のプラスチックカップに入れ、カイコ３令幼虫10頭を放
飼し、６日後の生死虫数を調査し、死虫率を求めた。 Test Example 3 Insecticidal test against 3rd-instar larvae of silkworm A dead sample prepared according to Example 1 was diluted with water to 400 p.
100 ml of the drug solution having a concentration of pm was prepared. Dry artificial feed for silkworms (Vita silk for silkworms produced by Kyodo Feed Co., Ltd.)
Was soaked and fully impregnated. This artificial feed is 9 cm in diameter
In a plastic cup of No. 10, 10 3rd-instar larvae of Bombyx mori were released, and the number of live and dead larvae was examined 6 days later to determine the mortality rate.
その結果は第３表の通りであった。The results are shown in Table 3.
〔発明の効果〕 本発明は顕著な殺虫、殺ダニ効果を有する極めて有用な
殺虫、殺ダニ剤である。 [Effects of the Invention] The present invention is an extremely useful insecticide and acaricide having a remarkable insecticidal and acaricidal effect.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 箕輪 宣人 神奈川県横浜市港北区師岡町760 明治製 菓株式会社薬品総合研究所内 (72)発明者 町並 智也 神奈川県横浜市港北区師岡町760 明治製 菓株式会社薬品総合研究所内 (72)発明者 柴原 聖至 神奈川県横浜市港北区師岡町760 明治製 菓株式会社薬品総合研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Nobuto Minowa Norito Minowa 760 Shimooka-cho, Kohoku-ku, Yokohama-shi, Kanagawa Meiji Seika Co., Ltd., Pharmaceutical Research Laboratory (72) Tomoya Machinami, 760 Meiji-cho, Kohoku-ku, Yokohama-shi, Kanagawa (72) Inventor Seiji Shibahara, 760 Seiji-cho, Kohoku-ku, Yokohama-shi, Kanagawa Meiji Seika Co., Ltd.
Claims (1)
を示す）を示し、R2は水素原子、メチル基又はエチル基
を示し、Ａは で表される2,3−ジ置換−４−ヒドロキシキノリン誘導
体の１種又は２種以上を有効成分とする殺虫、殺ダニ
剤。1. A formula [In the formula, R 1 represents a hydrogen atom or R 3 CO— (R 3 represents a lower alkyl group), R 2 represents a hydrogen atom, a methyl group or an ethyl group, and A represents An insecticidal or acaricidal agent comprising, as an active ingredient, one or more of 2,3-disubstituted-4-hydroxyquinoline derivatives represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17533389A JPH0796481B2 (en) | 1989-07-06 | 1989-07-06 | Insecticide, acaricide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17533389A JPH0796481B2 (en) | 1989-07-06 | 1989-07-06 | Insecticide, acaricide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0341004A JPH0341004A (en) | 1991-02-21 |
| JPH0796481B2 true JPH0796481B2 (en) | 1995-10-18 |
Family
ID=15994238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17533389A Expired - Fee Related JPH0796481B2 (en) | 1989-07-06 | 1989-07-06 | Insecticide, acaricide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0796481B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083644A1 (en) * | 2001-04-12 | 2002-10-24 | Meiji Seika Kaisha, Ltd. | Halogenated quinoline derivatives and ectoparasite controllers |
| JPWO2004032629A1 (en) * | 2002-10-11 | 2006-02-02 | 明治製菓株式会社 | Mixed composition for parasite control |
| WO2018169045A1 (en) * | 2017-03-17 | 2018-09-20 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | Mesostigmata mite control agent |
-
1989
- 1989-07-06 JP JP17533389A patent/JPH0796481B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0341004A (en) | 1991-02-21 |
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