WO1993003617A1 - Insecticidal composition - Google Patents

Insecticidal composition Download PDF

Info

Publication number
WO1993003617A1
WO1993003617A1 PCT/JP1992/001070 JP9201070W WO9303617A1 WO 1993003617 A1 WO1993003617 A1 WO 1993003617A1 JP 9201070 W JP9201070 W JP 9201070W WO 9303617 A1 WO9303617 A1 WO 9303617A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
optionally substituted
parts
insecticidal
insecticidal composition
Prior art date
Application number
PCT/JP1992/001070
Other languages
French (fr)
Japanese (ja)
Inventor
Michihiko Matsuda
Nobuo Takakusa
Jun Mitsui
Original Assignee
Nippon Soda 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 Nippon Soda Co., Ltd. filed Critical Nippon Soda Co., Ltd.
Publication of WO1993003617A1 publication Critical patent/WO1993003617A1/en

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Definitions

  • the present invention relates to a novel insecticidal composition having an excellent insecticidal effect, comprising a combination of an amide derivative of the following formula [I] and a synergist having a methylenedioxyphenyl group.
  • the present inventor studied a more effective use of the amine derivative represented by the following formula [I] and studied a combination with a synergist having a methylenedioxyphenyl group. It has been found that a powerful insecticidal effect can be obtained.
  • the present invention has the general formula (I)
  • R is an optionally substituted pyridyl group, virazyl group, or thiazolyl group, excluding an unsubstituted 2-pyridyl group
  • R 2 is a hydrogen atom
  • an optionally substituted R 3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, and represents a cyano group or a nitro group.
  • a salt thereof and a synergist having a methylenedioxyphenyl group It has been found that a novel active substance combination exhibits an excellent insecticidal effect.
  • Amin derivatives alone are used to control the insects such as aphid, leafhopper, rice weevil, brown beetle, fruit tree, vegetables, etc. It is more effective than usual and shows a synergistic insecticidal effect.
  • Preferred amide derivatives of the general formula [I] used in the insecticidal composition according to the present invention are defined as follows. .
  • R is a pyridyl group, a virazinyl group or a thiazolyl group which may be substituted with a halogen atom such as a chloro atom, excluding an unsubstituted 2-pyridyl group;
  • R 2 is a hydrogen atom;
  • R 3 represents a hydrogen atom, an alkyl group, and represents a Shimano group or a nitro group.
  • Examples of the amide derivative of the general formula [I] used in the insecticidal composition according to the present invention include the compounds shown in Table 1 below. Method for producing the amine derivative or salt thereof The methods and their use as insecticides are described in WO 91/04965 in the P Table 1
  • synergists having a methylenedioxyphenyl group used in the present invention include the compounds shown in Table 2. Common name structure
  • the weight ratio of the active substance in each group in the active substance is generally the same as that of the active substance in the active substance group of the amide derivative of the general formula [I] or a salt thereof.
  • 1 to 20 parts by weight of the agent can be used.
  • the insecticidal composition according to the present invention exhibits an excellent insecticidal effect, and is applied by spraying, top dressing, underwater application, water surface application, soil surface application, soil mixing treatment, planting hole treatment, seedling immersion, seed disinfection, seedling raising box It can be used for application, smoking, fumigation, application, bait etc.
  • the insecticidal composition according to the present invention exhibits a stronger insecticidal effect than when each active compound is applied alone, so that it has no phytotoxicity to crops, has low toxicity to mixed-breed animals, and can be used safely.
  • the insecticidal composition of the present invention comprises a compound represented by the general formula [I] and methylenedioxy. It contains a synergist having a fluorine group as an active ingredient, and can be used as it is as a pure product of the active ingredient compound. Water solvent, powder, emulsion, oil, granule, flowable, fumigation, fumigant, aerosol, liniment, bait, etc. Those prepared separately may be used as a mixture. Additives and carriers include solid powders, such as soy flour and flour, vegetable powders, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, and other mineral powders, sodium benzoate, urea, and the like. Organic and inorganic compounds such as sodium sulfate are used.
  • liquid dosage form uses vegetable oil, mineral oil, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, trichloroethylene, methylisobutyl Use ketone and water as solvents.
  • a surfactant can be added if necessary to obtain a uniform and stable form.
  • the wettable powder, emulsion, aqueous solvent, flowable, etc. thus obtained is diluted with water to a predetermined concentration to form a suspension or emulsion, and the oils, powders, and granules are sprayed as they are. Used in.
  • Example 2 wettable powder 10 parts of the active compound of the formula (I)
  • Test Example 1 Test on housefly Absorbent cotton was placed in a small petri dish having a diameter of 3 cm, and an aqueous solution of sugar having a predetermined concentration of a wettable powder according to the example was dropped, and used as poison bait. This petri dish was placed in a high petri dish and inoculated with 10 housefly adults. They were covered with a wire mesh and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%, and the insecticidal rate was examined two days later. Table 3 shows the results.
  • a cabbage leaf piece was added to an aqueous solution of a drug diluted to a predetermined concentration of a wettable powder according to Example 2. 170

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

An insecticidal composition comprising a compound represented by general formula (I) or a salt thereof and a synergist having a methylenedioxyphenyl group as the active ingredients, wherein R1 represents optionally substituted pyridyl, pyrazyl or thiazolyl, except for unsubstituted 2-pyridyl; R2 represents hydrogen, optionally substituted alkyl, cycloalkyl or alkoxy; R3 represents hydrogen or optionally substituted alkyl; and R4 represents cyano or nitro. The insecticidal effect of the composition is larger than that of the respective ingredient used alone, so that the synergism of the composition is excellent.

Description

明 殺 虫 組 成 物  Akira insecticide composition
技術分野  Technical field
本発明は後記式 〔 I〕 のァミ ン誘導体とメチレンジォキシフエ二ル基を有する 共力剤との組み合わせからなる優れた殺虫効果を有する新規な殺虫組成物に関す る。  The present invention relates to a novel insecticidal composition having an excellent insecticidal effect, comprising a combination of an amide derivative of the following formula [I] and a synergist having a methylenedioxyphenyl group.
背景技術  Background art
農園芸作物及び衛生害虫の防除に、 従来より、 多数の殺虫剤が使用されている 力 その防除効力が不十分であったり、 薬剤抵抗性の害虫の出現によりその使用 が制限されたり、 また、 植物体に薬害や汚染を生じたり、 あるいは人畜魚類など に対する毒性が強かつたりすることから、 必ずしも満足すべき防除薬剤とは言い 難いものが少なくない。 従って、 かかる欠点の少ない安全に使用できる薬剤の開 発が要望されている。  Many insecticides have been used to control agricultural and horticultural crops and sanitary pests. Power has been insufficient to control them, and the use of insect-resistant pests has limited their use. Because of the phytotoxicity and contamination of plants and the high toxicity to humans, fish, and the like, many of these are not necessarily satisfactory control agents. Therefore, there is a demand for the development of a drug that can be used safely with few such disadvantages.
本発明者は後記式 〔 I〕 で表されるアミ ン誘導体のより有効な利用を検討する 中で、 メチレンジォキシフエ二ル基を有する共力剤との組み合わせを研究した結 果、 共力的な殺虫効果が得られることを見出した。  The present inventor studied a more effective use of the amine derivative represented by the following formula [I] and studied a combination with a synergist having a methylenedioxyphenyl group. It has been found that a powerful insecticidal effect can be obtained.
発明の開示 Disclosure of the invention
本発明は、 一般式 〔 I〕  The present invention has the general formula (I)
R R
R , 一 C H 2 - N R R, one CH 2 -NR
〔 I 3 [I 3
N N
R  R
(式中、 R , は無置換 2—ピリジル基を除く、 置換されていてもよいピリジル 基、 ビラジル基又はチアゾリル基を、 R 2 は水素原子、 置換されていてもよいァ ルキル基、 シク ロアルキル基、 又はアルコキシ基を、 R 3 は水素原子、 置換され ていてもよいアルキル基を、 はシァノ基、 又はニ トロ基を示す。 ） で表され る化合物又はその塩及びメチレンジォキシフエ二ル基を有する共力剤を含有する 殺虫組成物であり、 新規な活性物質の組み合わせが優れた殺虫効果を示すことが 見出された。 (Wherein, R, is an optionally substituted pyridyl group, virazyl group, or thiazolyl group, excluding an unsubstituted 2-pyridyl group, R 2 is a hydrogen atom, an optionally substituted R 3 represents a hydrogen atom, a substituted or unsubstituted alkyl group, and represents a cyano group or a nitro group. And a salt thereof and a synergist having a methylenedioxyphenyl group. It has been found that a novel active substance combination exhibits an excellent insecticidal effect. Was.
一般式 〔 I〕 のァミ ン誘導体又はその塩にメチレンジォキシフヱ二ル基を有す る共力剤を配合した本発明による殺虫組成物の殺虫効果はァミ ン誘導体単独の効 果より大であり、 優れた共力作用を示す。  The insecticidal effect of the insecticidal composition according to the present invention in which a synergist having a methylenedioxyphenyl group is blended with the amide derivative of the general formula [I] or a salt thereof, shows the effect of the amide derivative alone. It is larger than fruit and shows excellent synergism.
即ち、 本発明による殺虫組成物を施用することにより、 例えば、 水稲の重要害 That is, by applying the insecticidal composition of the present invention, for example,
R K I  R K I
虫であるゥン力、 ョコバイ類、 イネミズゾゥムシ、 コブノメイガ、 果樹、 野菜等 の重要害虫であるアブラムシ、 コナガ、 ハマキムシ、 シンクイムシ、 衛生害虫で あるイエバニ、 力、 ゴキブリ等に対してァミ ン誘導体単独の場合より効果が大で、 共力的な殺虫効果を示す。  Amin derivatives alone are used to control the insects such as aphid, leafhopper, rice weevil, brown beetle, fruit tree, vegetables, etc. It is more effective than usual and shows a synergistic insecticidal effect.
本発明による殺虫組成物において使用される好ましい一般式 〔 I〕 のァミ ン誘 導体は下記のごとく定義される。 .  Preferred amide derivatives of the general formula [I] used in the insecticidal composition according to the present invention are defined as follows. .
RR
R C H : - N R RCH : -NR
[ I 3  [I 3
式中、 R , は無置換 2 —ピリ ジル基を除く、 クロル原子等のハロゲン原子で置 換されていてもよいピリ ジル基、 ビラジニル基もしく はチアゾリル基を、 R 2 は 水素原子、 低級アルキル基、 シクロプロピル基、 低級アルコキシ基を、 R 3 は水 素原子、 アルキル基を、 はシマノ基又はニトロ基を表す。 In the formula, R, is a pyridyl group, a virazinyl group or a thiazolyl group which may be substituted with a halogen atom such as a chloro atom, excluding an unsubstituted 2-pyridyl group; R 2 is a hydrogen atom; R 3 represents a hydrogen atom, an alkyl group, and represents a Shimano group or a nitro group.
本発明による殺虫組成物において使用される一般式 〔 I 〕 のァミ ン誘導体の例 と して次の表 1 に示す化合物が挙げられる。 該ァミ ン誘導体又はその塩の製造方 法及びそれらの殺虫剤としての使用は、 W O 9 1 / 0 4 9 6 5に記載されている P 表 1 Examples of the amide derivative of the general formula [I] used in the insecticidal composition according to the present invention include the compounds shown in Table 1 below. Method for producing the amine derivative or salt thereof The methods and their use as insecticides are described in WO 91/04965 in the P Table 1
Figure imgf000005_0001
Figure imgf000005_0001
一方、 本発明で用いられるメチレンジォキシフヱニル基を有する共力剤の例と して表 2に示す化合物が挙げられる。 一 般 名 構 造 式 On the other hand, examples of synergists having a methylenedioxyphenyl group used in the present invention include the compounds shown in Table 2. Common name structure
ピ ぺ ロ ニ ル  Pink
ブ ト キ シ ド
Figure imgf000006_0001
C Η 2〇 C 2 Η 4〇 C 2 Η 4 0 C 4 Η 0 Butoxyd
Figure imgf000006_0001
C Η 2 〇 C 2 Η 4 〇 C 2 Η 4 0 C 4 Η 0
° C H 3 ° CH 3
セサメ ッ ク ス Sesamex
5 スルフォキシ ド ピプロ タ ー ル  5 Sulfoxide piperotal
セ サ ミ ン Sesamin
サフ ロキサ ンSafloxane
Figure imgf000006_0002
活性物質における各群の活性物質の重量比は、 一般に、 一般式 〔 I〕 のァミ ン 誘導体またはその塩の活性物質群の活性物 Κ 1重量部当たり、 メチレンジォキシ フユ二ル基を有する共力剤を例えば 1〜2 0重量部使用できる。
Figure imgf000006_0002
In general, the weight ratio of the active substance in each group in the active substance is generally the same as that of the active substance in the active substance group of the amide derivative of the general formula [I] or a salt thereof. For example, 1 to 20 parts by weight of the agent can be used.
本発明による殺虫組成物は、 優れた殺虫効果を示し、 散布、 トップドレツシン グ、 水中施用、 水面施用、 土壌表面施用、 土壌混和処理、 植穴処理、 苗浸漬、 種 子消毒、 育苗箱施用、 燻煙、 燻蒸、 塗布、 毒餌等により使用することができる。 本発明による殺虫組成物は、 それぞれの活性化合物が単独で施用される場合よ り強く殺虫効果を示すため、 作物に対する薬害がなく、 混血動物に対する毒性も 低く、 安全に使用できる。  The insecticidal composition according to the present invention exhibits an excellent insecticidal effect, and is applied by spraying, top dressing, underwater application, water surface application, soil surface application, soil mixing treatment, planting hole treatment, seedling immersion, seed disinfection, seedling raising box It can be used for application, smoking, fumigation, application, bait etc. The insecticidal composition according to the present invention exhibits a stronger insecticidal effect than when each active compound is applied alone, so that it has no phytotoxicity to crops, has low toxicity to mixed-breed animals, and can be used safely.
本発明の殺虫組成物は、 一般式 〔 I〕 で表される化合物及びメチレンジォキシ フユ二ル基を有する共力剤を有効成分として含有するものであり、 有効成分化合 物の純品のままでも使用できるが、 通常、 一般の殺虫剤のとり得る形態、 即ち、 水和剤、 水溶剤、 粉剤、 乳剤、 油剤、 粒剤、 フロアブル、 燻煙剤、 燻蒸剤、 エア ゾール剤、 塗布剤、 毒餌剤等の形態に同時に混合製剤して使用しても良いし、 或 いは、 別々に製剤したものを混合して使用しても良い。 添加剤及び担体としては、 固形剤を目的とする場合は、 大豆粉、 小麦粉等の植物性粉剤、 珪藻土、 燐灰石、 石膏、 タルク、 ベントナイ ト、 クレイ等の鉱物性粉末、 安息香酸ソーダ、 尿素、 芒硝等の有機及び無機化合物が使用される。 The insecticidal composition of the present invention comprises a compound represented by the general formula [I] and methylenedioxy. It contains a synergist having a fluorine group as an active ingredient, and can be used as it is as a pure product of the active ingredient compound. Water solvent, powder, emulsion, oil, granule, flowable, fumigation, fumigant, aerosol, liniment, bait, etc. Those prepared separately may be used as a mixture. Additives and carriers include solid powders, such as soy flour and flour, vegetable powders, diatomaceous earth, apatite, gypsum, talc, bentonite, clay, and other mineral powders, sodium benzoate, urea, and the like. Organic and inorganic compounds such as sodium sulfate are used.
液体の剤型を、 目的とする場合は、 植物油、 鉱物油、 ケロシン、 キシレン及び ソルベン卜ナフサ等の石油留分、 シクロへキサン、 シクロへキサノン、 ジメチル ホルムアミ ド、 ジメチルスルホキシド、 トリクロルエチレン、 メチルイソブチル ケトン、 水を溶剤として使用する。 これらの製剤において、 均一なかつ安定な形 態をとるために必要ならば界面活性剤を添加することもできる。 このようにして 得られた水和剤、 乳剤、 水溶剤、 フロアブル剤等は水で所定の濃度に希釈して懸 濁液あるいは乳濁液として、 油剤、 粉剤、 粒剤はそのまま、 散布する方法で使用 される。  If the liquid dosage form is intended, use vegetable oil, mineral oil, petroleum fractions such as kerosene, xylene and sorbent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, trichloroethylene, methylisobutyl Use ketone and water as solvents. In these formulations, a surfactant can be added if necessary to obtain a uniform and stable form. The wettable powder, emulsion, aqueous solvent, flowable, etc. thus obtained is diluted with water to a predetermined concentration to form a suspension or emulsion, and the oils, powders, and granules are sprayed as they are. Used in.
発明を実施するための最良の形態 BEST MODE FOR CARRYING OUT THE INVENTION
次に製剤の実施例を示すが、 添加する担体、 界面活性剤等はこれらの実施例に 限定されるものではない。  Next, examples of the preparation are shown, but the carrier, surfactant and the like to be added are not limited to these examples.
実施例 1 乳剤 Example 1 Emulsion
式 〔 I〕 の活性化合物 5部  5 parts of active compound of the formula (I)
ピぺロニルブトキシド 1 0部  Pironyl butoxide 10 parts
アルキルフヱニルポリオキシエチレン 5部  Alkyl phenyl polyoxyethylene 5 parts
ジメチルホルムァミ ド 4 5部  Dimethylformamide 4 5 parts
キシレン 3 5部  Xylene 3 5 parts
以上を混合溶解し、 使用に際し水で希釈して乳濁液として散布する。  Mix and dissolve the above, dilute with water before use and spray as an emulsion.
実施例 2 水和剤 式 〔 I〕 の活性化合物 1 0部 Example 2 wettable powder 10 parts of the active compound of the formula (I)
セサメ ックス 2 0部  Sesamex 20
高級アルコール硫酸エステル 5部  Higher alcohol sulfate 5 parts
珪藻土 6 0部  Diatomaceous earth 60 parts
シリ力 5部  Siri force 5 parts
以上を混合して微粉に粉碎し、 使用に際し水で希釈して懸濁液として散布する, 実施例 3 粉剤  Combine the above, pulverize into fine powder, dilute with water before use and spray as a suspension, Example 3
式 （ I〕 の活性化合物 5部  5 parts of active compound of formula (I)
ピぺロニルブトキシド 1 0部  Pironyl butoxide 10 parts
タルク 8 4. 7部  Talc 8 4.7 parts
シリカ 0. 3部  Silica 0.3 parts
以上を混合粉砕し、 使用に際してはそのまま散布する。  Mix and grind the above and spray as it is when using.
実施例 4 粒剤  Example 4 granules
式 〔 I〕 の活性化合物 5部  5 parts of active compound of the formula (I)
ピぺロニルブトキシ ド 1 0部  Pironyl butoxide 10 parts
クレー 6 3部  Clay 6 3 parts
ベン トナイ 卜 2 0部  Bentonite 20
ジォクチルスルホサクシネー トナ ト リウム塩 1部  Dioctyl sulfosuccinate sodium salt 1 part
リ ン酸ナ ト リウム 1部  1 part sodium phosphate
以上を造粒し、 使用に際してはそのまま施用する。  Granulate the above and apply as it is when used.
実施例 5 油剤 Example 5 Oil agent
式 〔 I〕 の活性化合物 1部  1 part of active compound of the formula (I)
ピぺロニルブトキシ ド 5部  Pironyl butoxide 5 parts
ケロシン 9 4部  Kerosene 9 4 parts
以上を混合溶解し、 使用に際してはそのまま散布する。 ' 産業上の利用可能性  Mix and dissolve the above and spray as it is when using. '' Industrial applicability
試験例 1 イエバエに対する試験 直径 3 cmの小型シャーレに脱脂綿を入れ、 実施例 に準じた水和剤の所定濃度 の砂糖水溶液を滴下し、 毒餌として供試した。 このシャーレを腰高シャーレに入 れ、 イエバエ成虫 1 0頭を接種した。 金網で蓋をして、 温度 2 5 °C、 湿度 6 5 % の恒温室内に置き、 2日後に殺虫率を調査した。 結果を表 3に示した。 Test Example 1 Test on housefly Absorbent cotton was placed in a small petri dish having a diameter of 3 cm, and an aqueous solution of sugar having a predetermined concentration of a wettable powder according to the example was dropped, and used as poison bait. This petri dish was placed in a high petri dish and inoculated with 10 housefly adults. They were covered with a wire mesh and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%, and the insecticidal rate was examined two days later. Table 3 shows the results.
表 3  Table 3
Figure imgf000009_0001
試験例 2 コナガに対する試験
Figure imgf000009_0001
Test Example 2 Test for Conaga
実施例 2に準じた水和剤の所定濃度に希釈した薬剤の水溶液に、 キャベツ葉片 170 A cabbage leaf piece was added to an aqueous solution of a drug diluted to a predetermined concentration of a wettable powder according to Example 2. 170
8 を 3 0秒間浸漬した。 風乾後、 シャーレに処理葉を入れ、 コナガ 2令幼虫 1 0頭 を接種した。 ガラス蓋をして、 温度 2 5 °C、 湿度 6 5 %の恒温室内に置き、 3曰 後に殺虫率を調査した。 結果を表 4に示した。  8 was immersed for 30 seconds. After air-drying, the treated leaves were placed in a petri dish and inoculated with 10 second instar larvae. They were covered with a glass lid and placed in a thermostatic chamber at a temperature of 25 ° C and a humidity of 65%. Table 4 shows the results.
表 4 有 効 成 分 濃 度 （p pm) 殺 虫 率 薬 剤 名  Table 4 Effective ingredient concentration (p pm) Insecticidal rate
式 〔 I 〕 の活性化合物 共 力 剤 ( % ) 化 合 物 1 +  Active compound of formula (I) Synergist (%) Compound 1 +
o  o
D 1 0 0 ピぺロニルブトキシ ド 化 合 物 1 8 0 化 合 物 8 +  D 100 Pyronyl butoxide compound 180 Compound 8 +
8 1 2 5 1 0 0 ピぺロニルブトキシ ド 化 合 物 8 8 0  8 1 2 5 1 0 0 Pironyl butoxide compound 8 8 0
ピぺロニルブトキシ ド 1 2 5 0 Pironyl butoxide 1 2 5 0

Claims

請 求 の 範 囲 The scope of the claims
1 . 一般式 〔 I〕  1. General formula [I]
C I〕
Figure imgf000011_0001
CI)
Figure imgf000011_0001
N  N
I  I
(式中、 R , は無置換 2—ピリジル基を除く、 置換されていてもよいピリジル 基、 ビラジル基又はチアゾリル基を、 R 2 は水素原子、 置換されていてもよいァ ルキル基、 シクロアルキル基、 又はアルコキシ基を、 R 3 は水素原子、 置換され ていてもよいアルキル基を、 R 4 はシァノ基、 又はニトロ基を示す。 ） で表され る化合物又はその塩及びメチレンジォキシフエ二ル基を有する共力剤とを有効成 分として含有することを特徴とする殺虫組成物。 (Wherein, R, represents an optionally substituted pyridyl group, virazyl group or thiazolyl group, excluding an unsubstituted 2-pyridyl group; R 2 represents a hydrogen atom, an optionally substituted alkyl group, a cycloalkyl group; R 3 represents a hydrogen atom, an optionally substituted alkyl group, R 4 represents a cyano group or a nitro group, or a salt thereof, and methylenedioxyphene. An insecticidal composition comprising a synergist having a benzyl group as an active ingredient.
PCT/JP1992/001070 1991-08-27 1992-08-25 Insecticidal composition WO1993003617A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3238925A JPH0558811A (en) 1991-08-27 1991-08-27 Insecticidal composition
JP3/238925 1991-08-27

Publications (1)

Publication Number Publication Date
WO1993003617A1 true WO1993003617A1 (en) 1993-03-04

Family

ID=17037319

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1992/001070 WO1993003617A1 (en) 1991-08-27 1992-08-25 Insecticidal composition

Country Status (2)

Country Link
JP (1) JPH0558811A (en)
WO (1) WO1993003617A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996003879A1 (en) * 1994-07-29 1996-02-15 Bayer Aktiengesellschaft Insecticides
EP0617890B1 (en) * 1993-03-18 1998-11-18 Nihon Bayer Agrochem K.K. Synergistic insecticidal compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006298767A (en) * 2005-04-15 2006-11-02 Sumitomo Chemical Co Ltd Controlling agent for insect pest of suborder brachycera
ITMI20050729A1 (en) * 2005-04-22 2006-10-23 Endura Spa NEW BIOLOGICALLY ACTIVE FORMULATION

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991004965A1 (en) * 1989-10-06 1991-04-18 Nippon Soda Co., Ltd. Amine derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991004965A1 (en) * 1989-10-06 1991-04-18 Nippon Soda Co., Ltd. Amine derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0617890B1 (en) * 1993-03-18 1998-11-18 Nihon Bayer Agrochem K.K. Synergistic insecticidal compositions
WO1996003879A1 (en) * 1994-07-29 1996-02-15 Bayer Aktiengesellschaft Insecticides

Also Published As

Publication number Publication date
JPH0558811A (en) 1993-03-09

Similar Documents

Publication Publication Date Title
EA003186B1 (en) Pesticidal 1-arylpyrazoles
JPH03115266A (en) N-phenylpyrazole derivative
SK60094A3 (en) Phenylhydrazine derivatives, pesticidal agent containing these matters and method of controlling of nondesirable insect
KR100742976B1 (en) Pesticidal 1-aryl-3-iminopyrazoles
JPH04235104A (en) Insecticidal and miticidal composition
JPH04112805A (en) Insecticide composition
JPH0267270A (en) N-phenylphyrazol-4-yl ether derivative
PT1263734E (en) 3-thiomethylpyrazoles as pesticides
JPH03109376A (en) Derivative of n-phenylpyrazole
WO1993003617A1 (en) Insecticidal composition
WO2015135424A1 (en) Pesticidal composition and method for controlling pests
JP4796594B2 (en) Insecticidal, acaricidal and bactericidal nitromethylene compounds
PL83258B1 (en) Substituted amino diazinyl compounds and pesticidal compositions thereof[gb1394816a]
JPS5829281B2 (en) Barbiturate herbicide
JPH04112804A (en) Insecticide composition
WO1992021241A1 (en) Agrohorticultural insecticidal and bactericidal composition
JPH0368566A (en) Derivative of 5-substituted 3-aryl inoxazole, its preparation and expellant medicine for controlling harmful organism containing same
JPH04108704A (en) Insecticidal and fungicidal composition
HU222014B1 (en) Method of combatting insect eggs
JP2990865B2 (en) Insecticidal composition for agricultural and horticultural use
JPS63250306A (en) Agricultural and horticultural fungicide composition
JP4602491B2 (en) Pest control agent
JPS5843905A (en) Fungicide and insecticide composition for rice crop
JPS58188804A (en) Herbicide
JPH06503825A (en) Heterocyclic pesticidal compounds

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): BR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL SE

122 Ep: pct application non-entry in european phase