JPS603300B2 - Imidazole derivatives and insecticides and acaricides - Google Patents
Imidazole derivatives and insecticides and acaricidesInfo
- Publication number
- JPS603300B2 JPS603300B2 JP3855177A JP3855177A JPS603300B2 JP S603300 B2 JPS603300 B2 JP S603300B2 JP 3855177 A JP3855177 A JP 3855177A JP 3855177 A JP3855177 A JP 3855177A JP S603300 B2 JPS603300 B2 JP S603300B2
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- group
- river
- compound
- lower alkyl
- insecticide
- Prior art date
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Description
【発明の詳細な説明】
本発賜は新規な化合物及びその使用に関し、詳しくは−
般式(1)
(式中、X,、X2及び×3はハロゲン原子を、Yはハ
ロゲン原子、低級アルキル基又は低級アルコキシ基を、
nは0、1又は2を、R,及びR2は水素原子、低級ア
ルキル基、フェニル基又はペンジル基を示す。[Detailed Description of the Invention] The present invention relates to a novel compound and its use, and in detail -
General formula (1) (wherein, X, X2 and x3 are halogen atoms, Y is a halogen atom, lower alkyl group or lower alkoxy group,
n represents 0, 1 or 2; R and R2 represent a hydrogen atom, a lower alkyl group, a phenyl group or a penzyl group.
)で表わされる化合物及び該化合物類を有効成分として
含有する殺虫殺ダニ剤に関するものである。本発明の目
的とするところは植物に対する薬害がほとんどなく、か
つ人畜魚類に対する叢性が低く、安全に使用しうる殺虫
殺ダニ剤を提供するにある。) and insecticides and acaricides containing the compounds as active ingredients. The object of the present invention is to provide an insecticide and acaricide that causes almost no phytotoxicity to plants, has a low clump-like effect on humans, livestock, and fish, and can be used safely.
衛生害虫、植物害虫及び植物寄生性ダニ類の防除に用い
られる天然及び合成の薬剤は年々その量も種類も多くな
っているが、裁培植物に対する薬害や温血動物に対する
急性菱性、更には裁塔植物や蓄産物に於ける長期残留毒
性の故に安全に使用しうるものは少ない。The amount and variety of natural and synthetic agents used to control sanitary pests, plant pests, and plant parasitic mites have increased year by year, but they have been shown to cause phytotoxicity to cultured plants, acute rhododendrons to warm-blooded animals, and even more. There are few products that can be used safely due to long-term residual toxicity in turmeric plants and stored products.
また最近は現在使用されている薬剤に抵抗性を有する昆
虫、ダニ類が出現しそれらの防除は困難を極めている。
従ってこれらの諸問題を鱗決すべ〈有効な、かつ経済的
な有害生物防除剤の出現が強く要請されている。本発明
者らは、多数の有機化合物を合成し、各種の生物試験を
行って釆たところ、前記一般式(1)で表わされる化合
物類が衛生害虫、植物害虫及び植物寄生性ダニ類に対し
て優れた毅虫殺ダニ効力を有することを見出し、更に、
生物学的、物理化学的研究を重ね本発明を完成した。In addition, insects and mites that are resistant to currently used drugs have recently appeared, making it extremely difficult to control them.
Therefore, there is a strong demand for the emergence of effective and economical pest control agents that can solve these problems. The present inventors synthesized a large number of organic compounds and conducted various biological tests, and found that the compounds represented by the general formula (1) are effective against sanitary pests, plant pests, and plant parasitic mites. It was discovered that it has excellent insecticidal and acaricidal efficacy, and furthermore,
The present invention was completed through repeated biological and physicochemical research.
本発明化合物に類似の化合物としては、N・Nージメチ
ル−N′−(3・4ージニトロフエニル)一(4・5一
ジクロロイミダゾリル)一【11−アミジン等があり、
除草剤として、また、弱い殺ダニ効力を有するものとし
て知られている(持開昭50一13斑3号)。Compounds similar to the compounds of the present invention include N,N-dimethyl-N'-(3,4-dinitrophenyl)-(4,5-dichloroimidazolyl)-[11-amidine, etc.
It is known as a herbicide and as having a weak acaricidal effect (Jikai Sho 50-13 Spot No. 3).
本発明化合物類は、上記既知化合物類に比し2〜1“音
の殺ダニ効力を有しており、しかも薬害が軽減されてい
る。The compounds of the present invention have acaricidal efficacy of 2 to 1" higher than the above-mentioned known compounds, and have reduced chemical damage.
特に、前記一般式(1)において、X,、X2及び×3
が臭素原子でありR,及びR2が低級アルキル基である
化合物は薬害もなく、効力も優れている。In particular, in the general formula (1), X, , X2 and x3
Compounds in which is a bromine atom and R and R2 are lower alkyl groups have no phytotoxicity and are excellent in efficacy.
本発明化合物の製造にあたっては、一般式(〇)
(式中、Y、n、R,及びR2は先に定義したものと同
一の意味を有する。In the production of the compound of the present invention, the general formula (〇) (wherein Y, n, R, and R2 have the same meanings as defined above) is used.
)で表わされる化合物とトリハロィミダゾールとを、不
活性溶媒中、酸結合剤の存在下で反応させる。不活性溶
媒としては、アセトニトリル、アセトン、ク。ロホルム
、ジクロルメタン、ジメチルスルホキシド、テトラヒド
ロフラン等の極性溶媒が用いられ、酸結合剤としては炭
酸ナトリウム、炭酸カリウム、水酸化ナトリウム、イミ
ダゾール、トリメチルアミン、トリェチルアミン、ピリ
ジン等が用いられる。反応温度は0〜90午○、好まし
くは室温〜溶媒の沸点である。反応時間としては3粉ご
〜数時間を要する。反応終了後、酸結合剤の塩が折出し
た場合はこれを猿別後溶媒を留去する。残燭を、クロロ
ホルム等の適当な溶媒に溶解し、水洗、乾燥後、溶媒を
蟹去すれば略純粋な本発明化合物が好収率で得られる。
必要ならば更に再結晶又はカラムクロマトグラフィーに
より精製し、元素分析、IRスペクトル、NMRスペク
トル、マススベクトル等の分析結果から構造を決定した
。次に、合成例を挙げて本発明化合物の製造方法につい
て更に詳しく説明する。) and trihaloimidazole are reacted in an inert solvent in the presence of an acid binder. Examples of inert solvents include acetonitrile, acetone, and chlorine. Polar solvents such as roform, dichloromethane, dimethyl sulfoxide, and tetrahydrofuran are used, and sodium carbonate, potassium carbonate, sodium hydroxide, imidazole, trimethylamine, triethylamine, pyridine, and the like are used as acid binders. The reaction temperature is from 0 to 90 o'clock, preferably from room temperature to the boiling point of the solvent. The reaction time is 3 minutes to several hours. After the reaction is complete, if the salt of the acid binder is precipitated, it is separated and the solvent is distilled off. By dissolving the residual candle in a suitable solvent such as chloroform, washing with water, drying, and removing the solvent, a substantially pure compound of the present invention can be obtained in a good yield.
If necessary, it was further purified by recrystallization or column chromatography, and the structure was determined from the results of elemental analysis, IR spectrum, NMR spectrum, mass vector, etc. Next, the method for producing the compound of the present invention will be explained in more detail by giving a synthesis example.
合成例 1(化合物番号9)
20泌のアセトニトリル中に、トリプロムイミダゾール
2夕及び4ークロロフェニルイミノクロロカルボン酸ジ
ェチルアミド塩酸塩1.9夕を加え、縄投下に、室温で
トリェチルアミン1.4夕を滴下した。Synthesis Example 1 (Compound No. 9) In 20 parts of acetonitrile, 2 parts of tripromimidazole and 1.9 parts of 4-chlorophenyliminochlorocarboxylic acid diethylamide hydrochloride were added, and 1.4 parts of triethylamine was added to a rope at room temperature. dripped.
そのまま2〜3時間蝿拝を続けた後、反応液を200の
【の氷水中に法加し、析出した白色晶を猿取し、エタノ
ールより再結晶してN・Nージメチル−N一(4ークロ
ロフエニル)一(2・4・5ートリブロモイミダゾリル
)−m−アミジン3夕(収率90%)を得た。融点 8
7〜900合成例 2(化合物番号16)20の‘のア
セトニトリル中にトリブロムイミダゾール2夕及び2・
4ージクロロフェニルイミノクロロカルボン酸ジェチル
アミド塩酸塩1.9夕を加え、更に室温灘梓下にトリメ
チルアミン1・4夕を加えた。After continuing to stir for 2 to 3 hours, the reaction solution was added to 200 ml of ice water, the precipitated white crystals were filtered out, and recrystallized from ethanol to give N.N-dimethyl-N-(4 -chlorophenyl)-(2,4,5-tribromoimidazolyl)-m-amidine 3 (yield 90%) was obtained. Melting point 8
7-900 Synthesis Example 2 (Compound No. 16) Tribromimidazole 2 and 2.
1.9 hours of 4-dichlorophenyliminochlorocarboxylic acid diethylamide hydrochloride was added, and further 1.4 hours of trimethylamine was added at room temperature.
そのまま3時間蝿拝した後、反応物を200の‘の氷水
中に注加し析出した結晶を濃取し、エタノールより再結
晶してN・Nージメチル−N′−(2・4ージクロロフ
エニル)一(2・4・5ートリブロモイミダゾリル)一
【1’一アミジン3夕(収率88%)を得た。融点 1
43〜4℃合成例 3(化合物番号2)20の【のアセ
トニトリル中にトリブロモイミダゾール3夕及び2ーメ
チルー4ークロロフェニルィミノクロロカルボン酸ジェ
チルアミド塩酸塩2・7夕を加えた。After incubating for 3 hours, the reaction product was poured into 200 °C of ice water, the precipitated crystals were concentrated, and recrystallized from ethanol to give N.N-dimethyl-N'-(2,4-dichlorofluorophore). (yield: 88%). Melting point 1
43-4°C Synthesis Example 3 (Compound No. 2) Into 20 ml of acetonitrile were added 3 ml of tribromoimidazole and 2.7 ml of 2-methyl-4-chlorophenyliminochlorocarboxylic acid diethylamide hydrochloride.
更にトリメチルアミン2夕を麓梓下に室温で加え、その
まま3時間燈梓を続けた。その後、反応液を200肌【
氷水中に洋加し析出した結晶を渡取し、エタノールより
再結晶してN・N−ジメチルーN′−(2ーメチルー4
−クロロフヱニル)一(2・4・5ートリプロモイミダ
ゾリル)‘1’ーアミジン4.1夕(収率滋%)を得た
。融点 172〜4℃(分解)第1表に本発明代表化合
物の構造式及び物理定数を示す。Further, two portions of trimethylamine were added to the bottom of the azure at room temperature, and the azure was continued for 3 hours. After that, apply the reaction solution to 200 skin [
The crystals precipitated by dipping in ice water were taken and recrystallized from ethanol to obtain N・N-dimethyl-N'-(2-methyl-4
-chlorophenyl)-(2,4,5-tripromoimidazolyl)'1'-amidine (4.1 units (yield: %)) was obtained. Melting point: 172-4°C (decomposed) Table 1 shows the structural formulas and physical constants of representative compounds of the present invention.
第1表 一般式‘1}
本発明の殺虫殺ダニ剤は、有効成分化合物の納品のまま
でも使用できるし、また農薬として使用する目的で、一
般の農薬のとり得る形態、即ち、水和剤、粒剤、粉剤、
乳剤等の形態で使用することができる。Table 1 General formula '1} The insecticide and acaricide of the present invention can be used with the active ingredient compound as delivered, and for the purpose of using it as an agricultural chemical, it can be used in the form that general agricultural chemicals can take, that is, as a hydrating powder. , granules, powders,
It can be used in the form of an emulsion or the like.
添加剤及び担体としては、固定剤を目的とする場合は、
大豆粉、小麦粉等の植物性粉末、珪藻±、燐灰石、石膏
、夕ルク、パィロフイラィト、クレイ等の鉱物性微粉末
が使用される。液体の剤型を目的とする場合はケロシン
、鍵油、石油、ソルベントナフサ、キシレン、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、アルコール、アセトン、水等を溶
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
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、粉剤、粒剤はそのまま、植物に散布する方法で
使用される。次に製剤の実施例を示すが、本発明化合物
に添加する担体、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。As additives and carriers, when intended as a fixative,
Vegetable powders such as soybean flour and wheat flour, and mineral fine powders such as diatoms, apatite, gypsum, turk, pyrophyllite, and clay are used. When a liquid dosage form is intended, kerosene, key oil, petroleum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, water, etc. are used as the solvent. In these preparations, a surfactant may be added if necessary in order to obtain a uniform and stable form. The wettable powders and emulsions thus obtained are diluted with water to a predetermined concentration and used as a suspension or emulsion, and the powders and granules are sprayed on plants as they are. Next, examples of formulations will be shown, but the carrier, surfactant, etc. added to the compound of the present invention are not limited to these examples.
実施例 1
乳剤
本発駅ヒ合物 雌都アル
キルアリルポリオキシェチレン 5部ジメチルホル
ムアミド 5の郭キシレン
35部以上を混合溶解し、
使用に際し水で希釈して乳蟻液として散布する。Example 1 Emulsion main compound Meto alkylaryl polyoxyethylene 5 parts dimethylformamide 5 parts xylene
Mix and dissolve 35 parts or more,
Before use, dilute with water and spray as milk ant liquid.
実施例 2
水和物
本発明イヒ合物 2庇都高
級アルコール硫酸ェステル 5部蓬藻±
7$部ホワイトカ
ーボン 5部以上を混合して徴粉に粉
砕し、使用に際して水にて希釈する。Example 2 Hydrate Ihi compound of the present invention 2 parts Higher alcohol sulfate ester 5 parts Porphyllum ±
7$ parts white carbon Mix 5 parts or more, grind into a fine powder, and dilute with water before use.
実施例 3
粉剤 ,
本発明化合物 5部タルク
94.6部シリコン
0.3口アル
キルアリルポリオキシェチレン 0.1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 Powder, compound of the present invention 5 parts talc
94.6 parts silicon
Mix and grind 0.1 part or more of 0.3-mouth alkylaryl polyoxyethylene, and sprinkle as is before use.
実施例 4
粒剤
本発明化合物 5部タルク
41.75部珪藻
± 41.75部ペ
ントナイト 1の部リグニ
ンスルホン酸ソーダ 1.5部以上を混
合し、粒剤にして得る。Example 4 Granules Compound of the present invention 5 parts Talc
41.75 parts diatoms + 41.75 parts pentonite 1 part sodium ligninsulfonate 1.5 parts or more are mixed to obtain granules.
次に試験例を挙げ本発明化合物の殺虫剤ダニ効力を説明
する。Next, test examples will be given to explain the insecticidal and mite efficacy of the compound of the present invention.
試験例 1
アシノワハダニに対する効力
2寸鉢に植えられたインゲンの第1本葉にアシノワハダ
ニ雌成虫を30頭接種した。Test Example 1 Efficacy against Spider mites Thirty female adult spider mites were inoculated onto the first true leaves of green beans planted in a 2-inch pot.
1日後に傷害虫を取り除いて前記実施例に示された乳剤
の処方に従って調製された本発明薬剤を、化合物濃度が
500跡になるように水で希釈して散布した。One day later, the injured pests were removed, and the agent of the present invention prepared according to the emulsion formulation shown in the above example was diluted with water to a compound concentration of 500 mg and sprayed.
散布3日後に殺虫率を求めるとともに成虫を除去し、そ
の間に産下された卵に関して、成虫まで発育し得たか否
かを11日目に調査して、殺ダニ有効度を求めた。結果
は次の通りである。*3日後殺虫率及び殺ダニ有効度の
評価
100%川、80〜99%日、50〜79%十、0〜5
0%「殺ダニ有効度孫)=無処理区成虫完成数−処理区
成虫完成数 X ,。Three days after spraying, the insecticidal rate was determined and the adults were removed, and the eggs laid during that time were investigated on the 11th day to see if they had developed to adults to determine the degree of acaricidal effectiveness. The results are as follows. *Evaluation of insecticidal rate and acaricidal effectiveness after 3 days: 100%, 80-99%, 50-79%, 0-5
0% (acidicidal effectiveness) = Number of adults completed in the untreated area - Number of completed adults in the treated area X.
〇無処理区成虫完成数(特開和50−13533号)
( ″ )
( ″ )
試験例 2
ナミハダニに対する効力
2寸鉢に播種したインゲンの発芽後7〜10日を経過し
た第1本棄上に、有機リン剤抵抗性のナミハダニの雌成
虫を30頭接種した後、前記実施例の乳剤の処方に従っ
て調製された本発明薬剤を、化合物濃度が62.ふ31
.3及び15.銃肌こなるように水で希釈して散布した
。〇Number of adults completed in untreated area (Japanese Patent Application Laid-open No. 50-13533) ('') ('') Test Example 2 Efficacy against two-spotted spider mites Discarding of the first green beans 7 to 10 days after germination of green beans sown in 2-inch pots After inoculating 30 female adults of organophosphate-resistant two-spotted spider mites, the drug of the present invention prepared according to the formulation of the emulsion in the above example was applied at a compound concentration of 62. Fu31
.. 3 and 15. It was diluted with water and sprayed on the gun skin.
散布3日後に毅虫率を求めるとともに成虫を除去し、こ
の3日間に産付された卵に関し、成虫まで発育し得たか
否かを11日目に調査し殺ダニ有効度を求めた。結果は
次の通りである。3日後殺虫率の評価* 殺
グニ有効度の評価*化合物番号62.5ppm 31
.3ppm 15.6ppm 62.5ppm
31.3ppm 15.6ppml 川 州 W
W 升 十2 川 川 十日 十
3 M 川 什 十
4 M 川 日 +
5 州 川 日 +
6 M 川 川 川 什 十
7 川 州 川 日 日 +
8 州 M M 日 什 十
9 州 什 川 十
11 M 川 升 川 日 +12 川
川 什 十13 M 川
升 十 十14 川 十 日 十
十15 什 川 日 什 十16
什 川 川 川 什 十18 川 州
川 M 日 +19 川 川
日 +24 州 川 什 十
B** −
−C** − ÷ −
一ケルセン 川 州 十 什
日 +*、**3日後殺虫率の評価、殺ダニ有
効度の評価並びに比較化合物BびCは試験例1に同じ。Three days after spraying, the mite rate was determined, and the adults were removed.The eggs laid during these three days were examined on the 11th day to see if they had developed to adults, and the degree of acaricidal effectiveness was determined. The results are as follows. Evaluation of insecticidal rate after 3 days * Evaluation of crinicidal effectiveness * Compound number 62.5 ppm 31
.. 3ppm 15.6ppm 62.5ppm
31.3ppm 15.6ppml Kawashu W
W square 12 river river 10th 13 M river 14 M river day + 5 state river day + 6 M river river river 17 river state river day day + 8 state MM day 19 state river day 10 11 M river square river day +12 river river 113 M river
Masu 114 River 10 Day 10
115 tithe river day tithe 116
Ji River River River Ji 118 River State River M Day +19 River River
Day +24 State River 10B** -
−C** − ÷ −
One Kelsen river state ten tenths
Days +*, **Evaluation of insecticidal rate after 3 days, evaluation of acaricidal efficacy, and comparative compounds B and C were the same as in Test Example 1.
試験例 3ミカンハダニに対する効力
シャーレにミカン葉をのせ、ミカンハダニ雌成虫を20
頭接種した。Test example 3 Efficacy against citrus spider mites Place tangerine leaves on a petri dish, and add 20 female adult citrus spider mites.
Head inoculated.
葉の周囲には成虫が逃げないようにタングルを塗った。
1日後に、前記実施例の乳剤の処方に従い調製された本
発明薬剤を、化合物濃度が125柳になるように水で希
釈して散布し、散布3日後に殺虫率を求めた。Tangle was applied around the leaves to prevent adult insects from escaping.
One day later, the agent of the present invention prepared according to the formulation of the emulsion in the above example was diluted with water to a compound concentration of 125 willows and sprayed, and the insecticidal rate was determined three days after spraying.
結果は次の通りである。試験例 4
アワョトウに対する効力
本発明化合物を前記実施例に示された乳剤の処方に従に
、化合物濃度が500胸になるように水で希釈した。The results are as follows. Test Example 4 Efficacy against Armyworm The compound of the present invention was diluted with water to a compound concentration of 500% according to the emulsion formulation shown in the above example.
その薬液にトウモロコシ葉を3現砂間浸潰し、風乾後、
アワョトウ3令幼虫が5頭入っているシャーレにその葉
を入れた。ガラス蓋をして、温度25q0、湿度65%
の陣温室内に置き、4劉時間後に殺虫率を調べた。結果
は次の通りである。試験例 5イエバエに対する効力
粉末ミルクと砂糖を1:1の割合で混合した餌に、本発
明化合物を1%になるように浸入した。Corn leaves were soaked in the chemical solution for 3 minutes, and after air drying,
The leaves were placed in a petri dish containing five 3rd instar larvae. Close the glass lid, temperature 25q0, humidity 65%
The insecticide rate was examined after 4 hours. The results are as follows. Test Example 5 Efficacy against Houseflies The compound of the present invention was infiltrated to a concentration of 1% into a feed prepared by mixing powdered milk and sugar at a ratio of 1:1.
その餌をイエバエ雌成虫が20頭入ったポIJエチレン
カップの中に入れ、水も与えて蓋をし、温度25℃、湿
度65%の恒温室内に置き、5日後に殺虫率を調べた。
結果は次の通りである。試験例 6
チカィェカに対する効力
本発明化合物を前記実施例に示された乳剤の処方に従い
、水で3脚になるように希釈した。The bait was placed in a PoIJ ethylene cup containing 20 female adult house flies, water was added, the cup was covered, and the cup was placed in a thermostatic chamber at a temperature of 25°C and humidity of 65%, and the killing rate was examined after 5 days.
The results are as follows. Test Example 6 Efficacy against Chicajeka The compound of the present invention was diluted with water to three parts according to the emulsion formulation shown in the above example.
その薬液を200の‘のビーカーに150の【入れ、チ
カィェカ3令幼虫を10頭放った。2反復で、ビーカー
は温度25qC、湿度65%の恒温室内に置き、・7日
後の殺虫率を調べた。I put 150 of the chemical solution into a 200' beaker and released 10 3rd instar larvae. The beaker was placed in a thermostatic chamber at a temperature of 25 qC and a humidity of 65% for two repetitions, and the insect killing rate was examined after 7 days.
Claims (1)
Yはハロゲン原子、低級アルキル基又は低級アルコキシ
基を、nは0、1又は2を、R_1及びR_2は水素原
子、低級アルキル基、フエニル基又はベンジル基を示す
。 )で表わされる化合物。2 X_1、X_2及びX_3
が臭素原子である特許請求の範囲第1項記載の化合物。 3 R_1及びR_2が低級アルキル基である特許請求
の範囲第1又は2項記載の化合物。 4 R_1及びR_2がメチル基又はエチル基である特
許請求の範囲第3項記載の化合物。 5 Yが塩素原子、臭素原子又はメチル基である特許請
求の範囲第4項記載の化合物。 6 一般式 ▲数式、化学式、表等があります▼ (式中、X_1、X_2及びX_3はハロゲン原子をY
はハロゲン原子、低級アルキル基又は低級アルコキシ基
を、nは0、1又は2を、R_1及びR_2は水素原子
、低級アルキル基、フエニル基又はベンジル基を示す。 )で表わされる化合物を有効成分として含有することを
特徴とする殺虫殺ダニ剤。7 X_1、X_2及びX_
3が臭素原子である特許請求の範囲第6項記載の殺虫殺
ダニ剤。 8 R_1及びR_2が低級アルキル基である特許請求
の範囲第6項又は7項記載の殺虫殺ダニ剤。 9 R_1及びR_2がメチル基又はエチル基である特
許請求の範囲第8項記載の殺虫殺ダニ剤。 10 Yが塩素原子、臭素原子又はメチル基である特許
請求の範囲第9項記載の殺虫殺ダニ剤。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, X_1, X_2 and X_3 are halogen atoms,
Y represents a halogen atom, a lower alkyl group or a lower alkoxy group, n represents 0, 1 or 2, and R_1 and R_2 represent a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group. ). 2 X_1, X_2 and X_3
The compound according to claim 1, wherein is a bromine atom. 3. The compound according to claim 1 or 2, wherein R_1 and R_2 are lower alkyl groups. 4. The compound according to claim 3, wherein R_1 and R_2 are a methyl group or an ethyl group. 5. The compound according to claim 4, wherein Y is a chlorine atom, a bromine atom, or a methyl group. 6 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X_1, X_2 and X_3 represent halogen atoms with Y
represents a halogen atom, a lower alkyl group or a lower alkoxy group, n represents 0, 1 or 2, R_1 and R_2 represent a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group. ) An insecticide and acaricide characterized by containing a compound represented by the following as an active ingredient. 7 X_1, X_2 and X_
The insecticide and acaricide according to claim 6, wherein 3 is a bromine atom. 8. The insecticide and acaricide according to claim 6 or 7, wherein R_1 and R_2 are lower alkyl groups. 9. The insecticide and acaricide according to claim 8, wherein R_1 and R_2 are a methyl group or an ethyl group. 10. The insecticide and acaricide according to claim 9, wherein Y is a chlorine atom, a bromine atom, or a methyl group.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3855177A JPS603300B2 (en) | 1977-04-06 | 1977-04-06 | Imidazole derivatives and insecticides and acaricides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3855177A JPS603300B2 (en) | 1977-04-06 | 1977-04-06 | Imidazole derivatives and insecticides and acaricides |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS53124266A JPS53124266A (en) | 1978-10-30 |
JPS603300B2 true JPS603300B2 (en) | 1985-01-26 |
Family
ID=12528418
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3855177A Expired JPS603300B2 (en) | 1977-04-06 | 1977-04-06 | Imidazole derivatives and insecticides and acaricides |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS603300B2 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USD620809S1 (en) | 2009-04-23 | 2010-08-03 | Del Monte Corporation | Condiment package |
US9061796B2 (en) | 2009-04-23 | 2015-06-23 | H.J. Heinz Company | Multi-function condiment container |
-
1977
- 1977-04-06 JP JP3855177A patent/JPS603300B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS53124266A (en) | 1978-10-30 |
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