JPH0558811A - Insecticidal composition - Google Patents
Insecticidal compositionInfo
- Publication number
- JPH0558811A JPH0558811A JP3238925A JP23892591A JPH0558811A JP H0558811 A JPH0558811 A JP H0558811A JP 3238925 A JP3238925 A JP 3238925A JP 23892591 A JP23892591 A JP 23892591A JP H0558811 A JPH0558811 A JP H0558811A
- Authority
- JP
- Japan
- Prior art keywords
- group
- application
- optionally substituted
- formula
- insecticidal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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
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
Description
【0001】[0001]
【産業上の利用分野】本発明は後記式〔I〕のアミン誘
導体とメチレンジオキシフェニ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。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel insecticidal composition having an excellent insecticidal effect, which comprises a combination of an amine derivative of the following formula [I] and a synergist having a methylenedioxyphenyl group.
【0002】[0002]
【従来の技術】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が、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った
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。2. Description of the Related Art A large number of insecticides have been conventionally used for controlling agricultural and horticultural crops and sanitary pests, but their use is insufficient due to the insufficient control effect or the emergence of drug-resistant pests. It is difficult to say that it is a satisfactory control agent because it is limited, or it causes phytotoxicity or contamination on plants, or is highly toxic to human livestock and fish. Therefore, there has been a demand for the development of a drug that can be used safely with few such drawbacks.
【0003】[0003]
【発明が解決しようとする課題】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、メチレンジオキシフェニ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。DISCLOSURE OF THE INVENTION The present inventor studied a combination with a synergist having a methylenedioxyphenyl group in examining more effective utilization of an amine derivative represented by the formula [I] described later. As a result, they found that a synergistic insecticidal effect was obtained.
【0004】[0004]
【課題を解決するための手段】本発明は、一般式〔I〕The present invention has the general formula [I]
【化2】 (式中、R1 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、ピラジル基又はチアゾリル基
を、R2 は水素原子、置換されていてもよいアルキル
基、シクロアルキル基、又はアルコキシ基を、R3 は水
素原子、置換されていてもよいアルキル基を、R4 はシ
アノ基、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オキシフェニ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。[Chemical 2] (In the formula, R 1 is an optionally substituted pyridyl group, pyrazyl group or thiazolyl group excluding unsubstituted 2-pyridyl group, and R 2 is a hydrogen atom, an optionally substituted alkyl group or a cycloalkyl group. Or an alkoxy group, R 3 represents a hydrogen atom, an optionally substituted alkyl group, and R 4 represents a cyano group or a nitro group) or a salt thereof and a methylenedioxyphenyl group. It has been found that the insecticidal composition comprises a synergist having a novel active substance combination and exhibits an excellent insecticidal effect.
【0005】一般式〔I〕のアミン誘導体又はその塩に
メチレンジオキシフェニ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アミン誘導体単独
の効果より大であり、優れた共力作用を示した。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、水稲の重要害虫であるウンカ、ヨコバイ類、イネミ
ズゾウムシ、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エ、カ、ゴキブリ等に対してアミ
ン誘導体単独の場合より効果が大で、共力的な殺虫効果
を示した。The insecticidal composition of the present invention comprising the amine derivative of the general formula [I] or a salt thereof and a synergist having a methylenedioxyphenyl group has a greater insecticidal effect than that of the amine derivative alone. It showed synergism. That is,
By applying the insecticidal composition according to the present invention, for example, planthoppers that are important pests of paddy rice, leafhoppers, rice weevil, rice leaf weevil, aphids that are important pests such as fruit tree, vegetables, diamondback moth, leaf beetle, syncytidae,
It was more effective than the amine derivative alone against sanitary insects such as house flies, mosquitoes and cockroaches, and showed a synergistic insecticidal effect.
【0006】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〕のアミン誘導体は下記のごとく
定義される。Preferred amine derivatives of the general formula [I] used in the insecticidal composition according to the present invention are defined as follows.
【化3】 式中、R1 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たピリジル基もしくはチア
ゾリル基を、R2 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、R3 は水素原子、ア
ルキル基を、R4 はシアノ基又はニトロ基を表す。[Chemical 3] In the formula, R 1 represents a pyridyl group or a thiazolyl group substituted with a halogen atom such as a chloro atom, excluding an unsubstituted 2-pyridyl group, and R 2 represents a hydrogen atom, a lower alkyl group, a cyclopropyl group or a lower alkoxy group. , R 3 represents a hydrogen atom or an alkyl group, and R 4 represents a cyano group or a nitro group.
【0007】本発明による殺虫組成物において使用され
る一般式〔I〕のア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。該ア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、WO91/
04965に記載されている。Examples of the amine derivative of the general formula [I] used in the insecticidal composition according to the present invention include the compounds shown in Table 1 below. A method for producing the amine derivative or a salt thereof and use thereof as an insecticide are described in WO91 /
04965.
【0008】[0008]
【表1】 [Table 1]
【0009】一方、本発明で用いられるメチレンジオキ
シフェ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。On the other hand, examples of the synergist having a methylenedioxyphenyl group used in the present invention include the compounds shown in Table 2.
【0010】[0010]
【表2】 [Table 2]
【0011】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〕のアミン誘導体またはその塩
の活性物質群の活性物質1重量部当たり、メチレンジオ
キシフェニル基を有する共力剤を例えば1〜20重量部
使用できる。本発明による殺虫組成物は、優れた殺虫効
果を示し、散布、トップドレッシング、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。The weight ratio of the active substance of each group in the active substance is generally such that the synergistic compound having a methylenedioxyphenyl group per 1 part by weight of the active substance group of the amine derivative of the general formula [I] or a salt thereof. For example, 1 to 20 parts by weight of the agent can be used. The insecticidal composition according to the present invention shows an excellent insecticidal effect, spraying, top dressing, underwater application, water surface application, soil surface application, soil admixture treatment, planting hole treatment, seedling dipping, seed disinfection, seedling box application, smoking. , Fumigation, coating, poison bait, etc. can be used.
【0012】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 pesticidal composition according to the present invention exhibits a stronger pesticidal effect than the case where each active compound is applied alone, so that it has no phytotoxicity to crops and low toxicity to mixed-blooded animals and can be used safely.
【0013】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オキシフェニル基を有する
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 contains a compound represented by the general formula [I] and a synergist having a methylenedioxyphenyl group as active ingredients, and the active ingredient compounds are pure products. Although it can be used, it is usually in the form of general insecticides, that is, wettable powders, water solutions, powders, emulsions, oils, granules, flowables, fumigants, fumigants, aerosols, coatings, poison baits The preparations may be used in the form of an agent or the like in the form of a mixture at the same time, or the preparations separately may be mixed and used. As the additives and carriers, when the purpose is a solid agent, soybean flour, vegetable powder such as wheat flour,
Mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite and clay, and organic and inorganic compounds such as sodium benzoate, urea and mirabilite are used.
【0014】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トナフサ
等の石油留分、シクロヘキサン、シクロヘキサノン、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。When a liquid dosage form is intended, petroleum fractions such as vegetable oil, mineral oil, kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, trichloroethylene, methyl isobutyl ketone, water. Is used as a solvent. In these preparations, a surfactant can be added if necessary to take a uniform and stable form. The wettable powder, emulsion, water solvent, flowable agent, etc. thus obtained are diluted with water to a predetermined concentration to give a suspension or emulsion, and the oil, powder, and granules are used as they are.
Used in the method of spraying.
【0015】[0015]
【実施例】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。 実施例1 乳剤 式〔I〕の活性化合物 5部 ピペロニルブトキシド 10部 アルキルフェニルポリオキシエチレン 5部 ジメチルホルムアミド 45部 キシレン 35部 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。[Examples] Examples of formulations are shown below.
The surfactant and the like are not limited to these examples. Example 1 Emulsion Active compound of formula [I] 5 parts Piperonyl butoxide 10 parts Alkylphenyl polyoxyethylene 5 parts Dimethylformamide 45 parts Xylene 35 parts The above ingredients are mixed and dissolved, and diluted with water before use and sprayed as an emulsion.
【0016】 実施例2 水和剤 式〔I〕の活性化合物 10部 セサメックス 20部 高級アルコール硫酸エステル 5部 珪藻土 60部 シリカ 5部 以上を混合して微粉に粉砕し、使用に際し水で希釈して
懸濁液として散布する。Example 2 Wettable powder Active compound of formula [I] 10 parts Sesamex 20 parts Higher alcohol sulfate ester 5 parts Diatomaceous earth 60 parts Silica 5 parts Mix the above with fine powder and dilute with water before use Spray as a suspension.
【0017】 実施例3 粉剤 式〔I〕の活性化合物 5部 ピペロニルブトキシド 10部 タルク 84.7部 シリカ 0.3部 以上を混合粉砕し、使用に際してはそのまま散布する。Example 3 Dust formulation Active compound of formula [I] 5 parts Piperonyl butoxide 10 parts Talc 84.7 parts Silica 0.3 parts
【0018】 実施例4 粒剤 式〔I〕の活性化合物 5部 ピペロニルブトキシド 10部 クレー 63部 ベントナイト 20部 ジオクチルスルホサクシネートナトリウム塩 1部 リン酸ナトリウム 1部 以上を造粒し、使用に際してはそのまま施用する。Example 4 Granules Active compound of formula [I] 5 parts Piperonyl butoxide 10 parts Clay 63 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Sodium phosphate 1 part The above is applied as it is when used. To do.
【0019】 実施例5 油剤 式〔I〕の活性化合物 1部 ピペロニルブトキシド 5部 ケロシン 94部 以上を混合溶解し、使用に際してはそのまま散布する。Example 5 Oil agent Active compound of the formula [I] 1 part Piperonyl butoxide 5 parts Kerosene 94 parts The above components are mixed and dissolved and sprayed as they are before use.
【0020】[0020]
試験例1 イエバエに対する試験 直径3cmの小型シャーレに脱脂綿を入れ、実施例2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10頭を接種した。金網で蓋をして、温度25
℃、湿度65%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 against housefly A cotton pad was put in a small petri dish having a diameter of 3 cm, and an aqueous sugar solution having a predetermined concentration of a wettable powder according to Example 2 was dropped to be used as a poison bait. This petri dish was placed in a high waist petri dish, and 10 adult houseflies were inoculated. Cover with a wire net, temperature 25
It was placed in a thermostatic chamber at a temperature of 65 ° C. and a humidity of 65%, and the insecticidal rate was investigated 2 days later. The results are shown in Table 3.
【表3】 [Table 3]
【0021】試験例2 コナガに対する試験 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、キャベツ葉片を30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10頭を接種し
た。ガラス蓋をして、温度25℃、湿度65%の恒温室
内に置き、3日後に殺虫率を調査した。結果を表4に示
した。Test Example 2 Test against diamondback moth A piece of cabbage leaf was immersed for 30 seconds in an aqueous solution of a drug prepared by diluting a wettable powder according to Example 2 to a predetermined concentration. After air-drying, treated leaves were placed in a petri dish and 10 second-instar larvae of diamondback moth were inoculated. The glass cover was placed and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%, and the insecticidal rate was examined 3 days later. The results are shown in Table 4.
【表4】 [Table 4]
Claims (1)
ていてもよいピリジル基、ピラジル基又はチアゾリル基
を、R2 は水素原子、置換されていてもよいアルキル
基、シクロアルキル基、又はアルコキシ基を、R3 は水
素原子、置換されていてもよいアルキル基を、R4 はシ
アノ基、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オキシフェニ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。1. A compound represented by the general formula [I]: (In the formula, R 1 is an optionally substituted pyridyl group, pyrazyl group or thiazolyl group excluding unsubstituted 2-pyridyl group, and R 2 is a hydrogen atom, an optionally substituted alkyl group or a cycloalkyl group. Or an alkoxy group, R 3 represents a hydrogen atom, an optionally substituted alkyl group, and R 4 represents a cyano group or a nitro group) or a salt thereof and a methylenedioxyphenyl group. An insecticidal composition, which comprises a synergist with the compound as an active ingredient.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3238925A JPH0558811A (en) | 1991-08-27 | 1991-08-27 | Insecticidal composition |
PCT/JP1992/001070 WO1993003617A1 (en) | 1991-08-27 | 1992-08-25 | Insecticidal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3238925A JPH0558811A (en) | 1991-08-27 | 1991-08-27 | Insecticidal composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0558811A true JPH0558811A (en) | 1993-03-09 |
Family
ID=17037319
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3238925A Pending JPH0558811A (en) | 1991-08-27 | 1991-08-27 | Insecticidal composition |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPH0558811A (en) |
WO (1) | WO1993003617A1 (en) |
Cited By (2)
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 |
JP2008536894A (en) * | 2005-04-22 | 2008-09-11 | エンデュラ ソシエタ ペル アチオニ | New biologically active formulations |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3495056B2 (en) * | 1993-03-18 | 2004-02-09 | バイエルクロップサイエンス株式会社 | Insecticidal composition |
DE4426942A1 (en) * | 1994-07-29 | 1996-02-01 | Bayer Ag | Insecticidal agents |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE122006000027I2 (en) * | 1989-10-06 | 2010-10-21 | Nippon Soda Co | AMIN DERIVATIVES |
-
1991
- 1991-08-27 JP JP3238925A patent/JPH0558811A/en active Pending
-
1992
- 1992-08-25 WO PCT/JP1992/001070 patent/WO1993003617A1/en active Application Filing
Cited By (2)
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 |
JP2008536894A (en) * | 2005-04-22 | 2008-09-11 | エンデュラ ソシエタ ペル アチオニ | New biologically active formulations |
Also Published As
Publication number | Publication date |
---|---|
WO1993003617A1 (en) | 1993-03-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
UA58500C2 (en) | 5-amino-4-ethylsulfinyl-pyrazole compounds, process for their preparation, intermediates, pesticides and method for pest control | |
JPH03115266A (en) | N-phenylpyrazole derivative | |
KR100742976B1 (en) | Pesticidal 1-aryl-3-iminopyrazoles | |
RU2077201C1 (en) | Derivatives of 1-phenylimidazole, method of struggle against agriculture pests and composition for pesticide treatment | |
JP3681397B2 (en) | How to attract and control insects | |
JPH04235104A (en) | Insecticidal and miticidal composition | |
CS253597B2 (en) | Insecticide and/or ectoparasiticide and method of efficient substances production | |
JP5189642B2 (en) | Diazene oxide carboxylate for pesticides | |
JPH0558811A (en) | Insecticidal composition | |
JP2929213B2 (en) | Field-acting herbicide composition and herbicidal method | |
PL83258B1 (en) | Substituted amino diazinyl compounds and pesticidal compositions thereof[gb1394816a] | |
JP2990872B2 (en) | Insecticidal composition for agricultural and horticultural use | |
JPS6368505A (en) | Agricultural, insecticidal and germicidal composition | |
JPS63126805A (en) | Agricultural and horticultural insecticidal composition | |
JPS5829281B2 (en) | Barbiturate herbicide | |
JP3625012B2 (en) | Insecticidal composition | |
WO1992021241A1 (en) | Agrohorticultural insecticidal and bactericidal composition | |
JP2016520651A (en) | Parasite control compounds, methods and formulations | |
JP2990865B2 (en) | Insecticidal composition for agricultural and horticultural use | |
JPS6372610A (en) | Insecticidal and fungicidal composition for agricultural use | |
JP4602491B2 (en) | Pest control agent | |
JPS63162608A (en) | Expellent against noxious gastropods | |
JPS58192807A (en) | Insecticidal composition | |
JPS63154602A (en) | Agricultural and horticultural insecticidal and germicidal composition | |
UA144437U (en) | MEANS OF PLANT PROTECTION AGAINST HARMFUL INSECTS |