JPS59155344A - Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active component - Google Patents
Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active componentInfo
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- JPS59155344A JPS59155344A JP2826183A JP2826183A JPS59155344A JP S59155344 A JPS59155344 A JP S59155344A JP 2826183 A JP2826183 A JP 2826183A JP 2826183 A JP2826183 A JP 2826183A JP S59155344 A JPS59155344 A JP S59155344A
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Abstract
Description
【発明の詳細な説明】
本発明は一般式(r)
〔式中、R1は水素原子、)・・ノ素原子、塩素原子、
臭素原子またはメチル基を表わし、R2は水素原子また
はフ・・ノ素原子を表わす、、R8は炭素数2〜4のア
ルキル基または2,2.2−トリフルオロエチル基を表
わす。〕
で示されるエーテル化合物、その製造法およびそれを有
効成分として含有する殺虫、殺ダニ剤に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (r) [wherein R1 is a hydrogen atom]... a nitrogen atom, a chlorine atom,
It represents a bromine atom or a methyl group, R2 represents a hydrogen atom or a hydrogen atom, and R8 represents an alkyl group having 2 to 4 carbon atoms or a 2,2.2-trifluoroethyl group. ] The present invention relates to an ether compound represented by the following, a method for producing the same, and an insecticide and acaricide containing the same as an active ingredient.
本発明者らは、優れた殺虫、殺ダニ剤を開発すべく鋭意
検討を重ねた結果、前記一般式(I)で示されろエーテ
ル化合物が、高い殺虫、殺ダニ効力を有することを見出
し、本発明を完成するに至った。As a result of intensive studies to develop excellent insecticidal and acaricidal agents, the present inventors discovered that the ether compound represented by the general formula (I) has high insecticidal and acaricidal effects, The present invention has now been completed.
本発明化合物が特に有効な具体的害虫としては、ウンカ
類、ヨコバイ類、アブラムシ類、カメムシ類などの半翅
目、コナガ類、ヨトウガ類などの鱗翅目、コクゾウムシ
、マメコガネなどの鞘翅目、アカイエカ、イエバエなど
の双翅目コバネイプゴなどの直翅目、チャバネコキブリ
などの網翅目などが挙げられる。Specific pest insects for which the compound of the present invention is particularly effective include Hemiptera such as planthoppers, leafhoppers, aphids, and stink bugs; Lepidoptera such as mealybugs and armyworms; Coleoptera such as weevils and bean beetles; Culex pipiens; Examples include Diptera such as the house fly, Orthoptera such as Kobaneipugo, and Orthoptera such as the German cat roach.
本発明化合物は、一般式(II)
pつ
〔式中、R1およびR2は前述と同じ意味を有し、Zは
ハロゲン原子を表わす。〕
テ示すれるベンジルハライドと一般式+111)〔式中
、釉は前述と同じ意味を有する。]で示されるアルコー
ルのアルカリ金属塩とを反応させることにより得られ、
さらに詳しくは、例えば前記一般式〇Wで示されろアル
コールを非プロトン性極性溶媒(例えばジメチルホルム
アミド、ジメチルスルホキシド等)中、アルカリ金属水
素化物と反応させてアルカリ金属塩とし、これに一般式
(Jl)で示されるベンジルハライドを0℃〜50℃で
1〜12時間反応させて製造することができる。The compound of the present invention has the general formula (II) p [wherein R1 and R2 have the same meanings as above, and Z represents a halogen atom. ] Benzyl halide and general formula +111) [In the formula, glaze has the same meaning as above. ] is obtained by reacting the alcohol with an alkali metal salt,
More specifically, for example, the alcohol represented by the general formula It can be produced by reacting benzyl halide represented by Jl) at 0°C to 50°C for 1 to 12 hours.
一般式On)で示されるアルコールとしては以下のよう
なものが挙げられる。Examples of the alcohol represented by the general formula On) include the following.
2.2−ジメチル−2−(4−エトキシフェニル)エタ
ノール
2.2−ジメチル−2−(4−n−プロピルオキシフェ
ニル)エタノール
2.2−ジメチル−2(41so−プロピルオキシフェ
ニル)エタノール
2.2−ジメチル−2−(4−n−ブチルオキシフェニ
ル)エタノール
2.2−ジメチル−2−(4−(2、2、2−トリフル
オロエトキシ)フェニル)エタノ−lし
また、一般式(II)で示されるベンジルハライドとし
て以下のようなものが挙げられる。2.2-dimethyl-2-(4-ethoxyphenyl)ethanol2.2-dimethyl-2-(4-n-propyloxyphenyl)ethanol2.2-dimethyl-2(41so-propyloxyphenyl)ethanol2. 2-dimethyl-2-(4-n-butyloxyphenyl)ethanol 2.2-dimethyl-2-(4-(2,2,2-trifluoroethoxy)phenyl)ethanol-1 also has the general formula (II ) Examples of the benzyl halide represented by the formula include the following.
8−アニリノベンジルプロミド
8−(4−フルオロアニリノ)ペンジルクロリ ド
8−(4−クロロアニリノ)ベンジルプロミド
8−(4−ブロモアニリノ)ベンジルプロミド
8−(4−メチルアニリノ)ベンジルプロミド
(8−アニリノ−4−フルオロ)ベンジルプロミド
4−フルオロ−8−(4−フルオロアニリノ)ベンジル
クロリド
4−フルオロ−8−(4−クロロアニリノ)ベンジルク
ロリド
4−フルオロ−8−(4−ブロモアニリノ)ベンジルプ
ロミド
4−フルオロ−8−(4−メチルアニリノ)ベンジルプ
ロミド
次に本発明化合物の製造例を示す。8-Anilinobenzylbromide 8-(4-fluoroanilino)penzyl chloride 8-(4-chloroanilino)benzylbromide 8-(4-bromoanilino)benzylbromide 8-(4-methylanilino)benzylbromide (8 -anilino-4-fluoro)benzylbromide 4-fluoro-8-(4-fluoroanilino)benzyl chloride 4-fluoro-8-(4-chloroanilino)benzyl chloride 4-fluoro-8-(4-bromoanilino)benzyl Bromide 4-Fluoro-8-(4-methylanilino)benzyl bromide Next, an example of the production of the compound of the present invention will be shown.
製造例 化合物(2)の合成
水素化ナトリウム(60%オイルサスペンション)11
4q(2,86ミリモル)をラメ20モル)のジメチル
ホルム7ミドa nd、 溶液を滴下し、水素発生が終
わるまで内温5o〜80℃に保つ。Production example Synthesis of compound (2) Sodium hydride (60% oil suspension) 11
A solution of 4q (2.86 mmol) and 20 mol of dimethylform 7amide was added dropwise, and the internal temperature was maintained at 5o to 80°C until hydrogen generation was completed.
その後、室温まで冷やし3−アニリノ−4−フルオロベ
ンジルクロリド61211P(2,60ミリモル)のジ
メチルホルムアミド8 rnL溶液を滴下し、そのまま
室温で一夜攪拌する。次にその反応混合溶液を水50m
1に注入し、エーテル20m1で2回抽出し、そのエー
テル層を無水硫酸マグネシウムで乾燥した後、エーテル
を留去し、シリカゲルをつめたカラムクロマトグラフィ
ーにより分離m製し、8−アーチルア83グを淡芦色液
体として得た。Thereafter, the mixture was cooled to room temperature, and a solution of 3-anilino-4-fluorobenzyl chloride 61211P (2.60 mmol) in 8 rnL of dimethylformamide was added dropwise, and the mixture was stirred overnight at room temperature. Next, add the reaction mixture solution to 50ml of water.
1, extracted twice with 20ml of ether, dried the ether layer over anhydrous magnesium sulfate, distilled off the ether, and separated by column chromatography packed with silica gel to obtain 83g of 8-Archia. Obtained as a pale orange liquid.
前記の製造例と同じ様にして製造できろ本発明化合物の
いくつかをまとめて第1表に示す。Table 1 summarizes some of the compounds of the present invention that can be produced in the same manner as in the above production examples.
第1表
OR,pl
(注) 上記一般式で示されるエーテル化合物の置換幕
引 、 R11および助の内容
本発明化合物を殺虫、殺ダニ剤の有効成分として用いる
場合は、通常、固体担体、液体担体、ガス状担体あるい
はその他の製剤用補助剤(例えば界面活性剤、分散剤、
湿展剤、安定剤等)と混合して各種の製剤、例えば乳剤
、水和剤、粉剤、粒剤、油剤、エアゾール、加熱燻蒸剤
(蚊取線香、電気蚊取等)、フォッギング等の灯
一霧剤、非加熱燻蒸剤、毒餌等にする。Table 1 OR, pl (Note) Substitution of the ether compound represented by the above general formula, R11, and contents of the auxiliary When the compound of the present invention is used as an active ingredient of an insecticide or acaricide, it is usually prepared using a solid carrier or a liquid. carriers, gaseous carriers or other formulation auxiliaries (e.g. surfactants, dispersants,
Wetting agents, stabilizers, etc.) can be mixed with various preparations such as emulsions, wettable powders, powders, granules, oils, aerosols, heating fumigants (mosquito coils, electric mosquito repellents, etc.), fogging lights, etc. Use as a fog, non-heated fumigant, poison bait, etc.
これらの製剤中の有効成分含量は0.1%〜95%であ
る。The active ingredient content in these formulations is between 0.1% and 95%.
固体担体としては粘土類(例えばカオリン、ベントナイ
ト、酸性白土、ピロフィライト、セリサイト、)、タル
ク類、その他無機鉱物(たとえば水和二酸化ケイ素、軽
石、珪藻土、硫黄粉末、活性炭)などの微粉末ないし粉
状物が挙げられる。Solid carriers include fine powders or powders such as clays (e.g. kaolin, bentonite, acid clay, pyrophyllite, sericite), talcs, and other inorganic minerals (e.g. hydrated silicon dioxide, pumice, diatomaceous earth, sulfur powder, activated carbon). Examples include things like this.
また液体担体としてはアルコール類(例えばメチルアル
コール)、ケトン類(例えばアセトン、メチルエチルケ
トン)、エーテル類(例えばエチルエーテル、ジオキサ
ン、セロソルブ、テトラヒドロフラン)、芳香族炭化水
素類(例えばベンセン、トルエン、キシレン、メチルナ
フタレン)、脂肪族炭化水素類(例えばケロシン、灯油
)、エステル類、ニトリル類、酸アミド類(例えばジメ
チルホルム7εド、ジメチルアセドアミド)、ハロゲン
化炭化水素(例えばジクロロエタン、トリクロロエチレ
ン、四塩化炭素)などがあげられる。Liquid carriers include alcohols (e.g. methyl alcohol), ketones (e.g. acetone, methyl ethyl ketone), ethers (e.g. ethyl ether, dioxane, cellosolve, tetrahydrofuran), aromatic hydrocarbons (e.g. benzene, toluene, xylene, methyl naphthalene), aliphatic hydrocarbons (e.g. kerosene, kerosene), esters, nitriles, acid amides (e.g. dimethylform 7e, dimethylacedeamide), halogenated hydrocarbons (e.g. dichloroethane, trichloroethylene, carbon tetrachloride) ) etc.
また、界面活性剤としてはアルキル硫酸エステル類、ア
ルキルスルホン酸塩、アルキルアリールスルホン酸塩、
ポリエチレングリコールエーテル類、多価アルコールエ
ステル類などが挙げられる。In addition, as surfactants, alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates,
Examples include polyethylene glycol ethers and polyhydric alcohol esters.
さらに、使用できる固着剤や分散剤としてはカゼイン、
ゼラチン、でんぷん粉、CMC,アラビアゴム、アルギ
ン酸、リグニンスルフォネート、ベントナイト、精密、
ポリビニルアルコール、松根油、寒天などがあり、安定
剤としては例えばPAP(リン酸イソプロピル)、1’
CP(トリクレジルホスフェート)、トール油、エポキ
シ化油、各種界面活性剤、各種脂肪酸またはそのエステ
ルなどがあげられる。In addition, casein, fixing agents and dispersants that can be used include
Gelatin, starch powder, CMC, gum arabic, alginic acid, lignin sulfonate, bentonite, precision,
Examples of stabilizers include polyvinyl alcohol, pine oil, agar, and stabilizers such as PAP (isopropyl phosphate) and 1'
Examples include CP (tricresyl phosphate), tall oil, epoxidized oil, various surfactants, and various fatty acids or esters thereof.
次に製剤例を示す。Examples of formulations are shown below.
製剤例1
本発明化合物(1)〜(8)の各々0.5部を各々白灯
油に溶解し、全体を100部とすれば各々の油剤を得ろ
。Formulation Example 1 Dissolve 0.5 part of each of the compounds (1) to (8) of the present invention in white kerosene to make a total of 100 parts to obtain each oil solution.
製剤例2
本発明化合物(1)〜(8)の各々10部、それらに各
々乳化剤(ツルポール8005X(東邦化学登録商標名
))10部、キジロール70部を加え、これらをよく攪
拌混合すれば各々の乳剤を得ろ。Formulation Example 2 10 parts each of the compounds (1) to (8) of the present invention, 10 parts of an emulsifier (Tsurpol 8005X (registered trademark of Toho Chemical)), and 70 parts of Kijirol are added to each of them, and these are stirred and mixed well. Obtain the emulsion of
製剤例8
本発明化合物(1) 0.2部、テトラメスリン0.8
部、キジロール5部、脱臭灯油44.5部を混合溶解し
、エアゾール容器に充填し、バルブ部分を取り付けた後
、該バルブ部分を通じて噴射剤(液化石油ガス)50部
を加圧充填すればエアゾールを得る。Formulation Example 8 Compound of the present invention (1) 0.2 parts, tetramethrin 0.8
1 part, 5 parts of Kijiroll, and 44.5 parts of deodorized kerosene are mixed and dissolved, filled into an aerosol container, a valve part is attached, and 50 parts of propellant (liquefied petroleum gas) is pressurized and filled through the valve part to form an aerosol. get.
製剤例4
本発明化合物(2) 0.2部、アレスリンのd −ト
ランス酸体0.3部、脱臭灯油8.5部と乳化剤(アト
モス300(アトラスク°εカル社登録商標名))1部
とを混合し、純水60部を加えて乳化させたのち脱臭ブ
タン、脱臭プロパンの3二1混合物80部とともにエア
ゾール容器に充填すればウォーター・ベースエアゾール
を得る。Formulation Example 4 0.2 parts of the compound of the present invention (2), 0.3 parts of the d-trans acid form of allethrin, 8.5 parts of deodorized kerosene, and 1 part of emulsifier (Atmos 300 (registered trademark of Atlask Cal Inc.)) A water-based aerosol is obtained by mixing the mixture with 60 parts of pure water to emulsify it, and then filling it into an aerosol container with 80 parts of a 321 mixture of deodorized butane and deodorized propane.
製剤例5
本発明化合物(2)の10部に乳化剤(ソルボ ′−
ル5029−0(東邦化学登録商標名))5部をよく混
合し、800メツシュ珪i±85部を加え、充分攪拌混
合すれば水和剤を得ろ。Formulation Example 5 10 parts of the compound (2) of the present invention and an emulsifier (Sorbo'-
5029-0 (registered trademark of Toho Chemical Co., Ltd.)), add 800 mesh silicon i±85 parts, and stir and mix thoroughly to obtain a wettable powder.
製剤例6
本発明化合物(1)〜(8)の各々0.5部を適当量の
アセトンに溶解し、800メ・ソシュタルク99.5部
を加え充分攪拌混合した後、アセトノを蒸発除去すれば
各々の粉剤を得る。Formulation Example 6 Dissolve 0.5 parts of each of the compounds (1) to (8) of the present invention in an appropriate amount of acetone, add 99.5 parts of 800 Messstarc, stir thoroughly, and then remove the acetone by evaporation. Obtain each powder.
本発明化合物は広く農園芸用殺虫、殺ダニ剤として水田
、畑、果樹園、茶園、桑園、芝生地、牧草地、森林等の
ほか防疫用殺虫、殺ダニ剤として用いることもできる。The compounds of the present invention can be widely used as insecticides and acaricides for agricultural and horticultural purposes such as paddy fields, fields, orchards, tea gardens, mulberry gardens, lawns, pastures, forests, etc., and can also be used as insecticides and acaricides for epidemic prevention.
次に本発明化合物が殺虫、殺ダニ剤の有効成分として有
用であることを試験例をあげて示す。Next, test examples will be given to demonstrate that the compounds of the present invention are useful as active ingredients for insecticides and acaricides.
本発明化合物は第1表の化合物番号で、また比較対照と
して用いた化合物は次の化合物記号でそれぞれ示す。The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used as comparative controls are indicated by the following compound symbols.
付熱化合物 構 造 式 備 考試
験例1
直径5.5cmのポリエチレンカップの低に同大のr紙
を敷いた。製剤例2で得られた乳剤の200倍水希釈液
(500ppm相当)o、7mlをr紙の上に滴下した
。餌としてシヨ糖80svを沖紙上に入れた。その中に
イエバエ雌成虫10頭を放ち、フタをして48時間後に
その生死を調査し、成虫率を求めた(2反復)、。Heating Compound Structural Formula Remarks Test Example 1 R paper of the same size was placed on the bottom of a polyethylene cup with a diameter of 5.5 cm. 7 ml of a 200-fold water dilution (equivalent to 500 ppm) of the emulsion obtained in Formulation Example 2 was dropped onto R paper. 80 sv of sucrose was placed on the paper as bait. Ten female adult house flies were released into the container, the lid was closed, and 48 hours later, their survival and death were investigated to determine the adult rate (2 repetitions).
試験例2
製剤例2で得られた本発明化合物の乳剤の200倍水希
釈液(500PPm相当)2mlを1511のハスモン
ヨトウ用人工飼料にしみこませ、直径11ctnのポリ
エチレンカップに入れた。その中にハスモンヨトウ8令
幼中を10頭放ち、24時間後に生死を調査し、死生率
を求めた。(2反復)
試験例8
播種5日後の鉢植えツルナシインゲン4葉に1葉あたり
10頭のニセナミハダニ雌成虫(へン
物−の乳剤の200倍水希釈液(500ppm相当)を
ターンテーブル上で1鉢あたり10奴散布した。6日後
、植物上のニセナミハダニ雌成虫を数えた。Test Example 2 2 ml of a 200-fold water dilution (equivalent to 500 PPm) of the emulsion of the compound of the present invention obtained in Formulation Example 2 was impregnated into 1511 artificial feed for armyworm and placed in a polyethylene cup with a diameter of 11 ctn. Ten 8-year-old young and middle-aged Spodoptera were released into the cage, and 24 hours later, they were examined to see if they were alive or dead, and the mortality rate was calculated. (2 repetitions) Test Example 8 A 200-fold water dilution (equivalent to 500 ppm) of an emulsion of 10 female adult spider mites per leaf was applied to 4 leaves of potted green beans 5 days after sowing on a turntable. Ten spider mites were sprayed per pot. Six days later, female adult spider mites on the plants were counted.
効果判定基準は
十千1葉に雌成虫が0〜9頭寄生している+10〜80
〃
− 1葉に雌成虫が31頭以上寄生している
とした。結果を以下に示す。The criteria for determining effectiveness is 0 to 9 female adults per 1,000 leaves + 10 to 80.
- It is assumed that 31 or more adult female insects are infested on one leaf. The results are shown below.
千続補市書(e宜)
141件の表示
昭和夕を年 持r(゛願第282z/月2 発明の名称
ニー7−/し化合¥fJ2玉の製送汰右゛よび°玉凡1
有交hΔに令 と−J′v イた懺、王ミタ゛ 二」ト
〕3 補正をする者
事件どの関係 特許出願人
住 所 大阪市東区北浜5丁目15番地5、補正の対
象
明細書の発明の詳細な説明の欄
6、 補正の内容
(])明細書第9頁第8行目にr’ 788 Jとある
を[’18.8JとdJ圧する。141 items displayed in the Showa era
3. Relationship between the person making the amendment and the case Patent applicant address: 5-15-5 Kitahama, Higashi-ku, Osaka, invention of the specification subject to the amendment Detailed explanation column 6, Contents of amendment (]) On page 9, line 8 of the specification, r' 788 J is changed to ['18.8 J and dJ pressure.
(2)同第9頁の表をF記のように訂正する。(2) Correct the table on page 9 as shown in F.
「 」 以 上" ” that's all
Claims (3)
原子またはメチル基を表オフし、助は水素原子またはフ
ッ素原子を表わす。 助は炭素数2〜4のアルキル基または2゜2.2−)リ
フルオロエチル基ヲ表わす。〕で示されるエーテル化合
物。(1) General formula (1) [In the formula, R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or a methyl group, and the auxiliary represents a hydrogen atom or a fluorine atom. Substitute represents an alkyl group having 2 to 4 carbon atoms or a 2.2.2-)lifluoroethyl group. ] An ether compound represented by
原子またはメチル基を表わし、R2は水素原子または)
・ソ素原子を表オ〕才Zはハロゲン原子を表わす。〕 で示されるベンジルハライド、!: −ff式O1])
C式中、Kgは炭素数2〜4のアルキル基マタは2,2
.2−トリフルオロエチル基を表わす。〕 で示されるアルコールのアルカリ金属塩とを反応させる
ことを特徴とする一般式(I)1式中、R1,R2およ
びR3は前記と同じ意味を有する。] で示されるエーテル化合物の製造法。(2) General formula α1) 'CH2-Z [In the formula, R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom or a methyl group, and R2 represents a hydrogen atom or]
・Z represents a halogen atom. ] Benzyl halide, denoted by ! : -ff expression O1])
In formula C, Kg is an alkyl group having 2 to 4 carbon atoms, and 2,2
.. Represents a 2-trifluoroethyl group. ] In general formula (I) 1, which is characterized by reacting with an alkali metal salt of an alcohol represented by the above, R1, R2 and R3 have the same meanings as above. ] A method for producing an ether compound shown in the following.
素原子またはメチル基を表わし、R2は水素原子または
フ・ソ素原子を表わす。 R8は炭素数2〜4のアルキル基才たは2.2.2−ト
リフルオロエチル基を表オ)才。〕で示されろエーテル
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。(3) General formula (I) R8 In the formula, R1 represents a hydrogen atom, a hydrogen atom, a chlorine atom, a bromine atom, or a methyl group, and R2 represents a hydrogen atom or a hydrogen atom. R8 represents an alkyl group having 2 to 4 carbon atoms or a 2,2,2-trifluoroethyl group. ] An insecticide and acaricide characterized by containing an ether compound as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2826183A JPS59155344A (en) | 1983-02-21 | 1983-02-21 | Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active component |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2826183A JPS59155344A (en) | 1983-02-21 | 1983-02-21 | Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active component |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59155344A true JPS59155344A (en) | 1984-09-04 |
JPH0414098B2 JPH0414098B2 (en) | 1992-03-11 |
Family
ID=12243623
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2826183A Granted JPS59155344A (en) | 1983-02-21 | 1983-02-21 | Ether compound, its preparation and insecticidal and miticidal agent containing said compound as active component |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59155344A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157004A (en) * | 1983-02-26 | 1984-09-06 | Yoshio Katsuta | Insecticidal and miticidal agent containing novel 2-phenylpropyl ether derivative and its preparation |
JPS63159329U (en) * | 1987-04-08 | 1988-10-19 |
-
1983
- 1983-02-21 JP JP2826183A patent/JPS59155344A/en active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157004A (en) * | 1983-02-26 | 1984-09-06 | Yoshio Katsuta | Insecticidal and miticidal agent containing novel 2-phenylpropyl ether derivative and its preparation |
JPH0368841B2 (en) * | 1983-02-26 | 1991-10-30 | Yoshio Katsuta | |
JPS63159329U (en) * | 1987-04-08 | 1988-10-19 |
Also Published As
Publication number | Publication date |
---|---|
JPH0414098B2 (en) | 1992-03-11 |
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