JP2003335757A - Method for producing ether compound - Google Patents
Method for producing ether compoundInfo
- Publication number
- JP2003335757A JP2003335757A JP2002142616A JP2002142616A JP2003335757A JP 2003335757 A JP2003335757 A JP 2003335757A JP 2002142616 A JP2002142616 A JP 2002142616A JP 2002142616 A JP2002142616 A JP 2002142616A JP 2003335757 A JP2003335757 A JP 2003335757A
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- JP
- Japan
- Prior art keywords
- formula
- weight
- parts
- compound represented
- ether compound
- 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.)
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Links
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- Pyridine Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、殺虫・殺ダニ剤の
有効成分又はその製造中間体として有用なエーテル化合
物の製造法に関する。TECHNICAL FIELD The present invention relates to a method for producing an ether compound which is useful as an active ingredient for insecticides and acaricides or an intermediate for the production thereof.
【０００２】[0002]
【従来の技術および発明が解決しようとする課題】式
（４）
（式中、Ｒ2は水素原子又はハロゲン原子を表し、Ｒ3は
塩素原子又は臭素原子を表す。）で示されるジハロプロ
ペン化合物が殺虫・殺ダニ剤の有効成分として有用であ
り、また、式（５）
（式中、Ｒ2は水素原子又はハロゲン原子を表す。）で
示される化合物がその製造中間体として有用であること
が知られている（特開平９−１５１１７２号公報）。そ
して、該公報には１−ベンジルオキシ−３，５−ジクロ
ロ−４−［３−（５−トリフルオロメチルピリジン−２
−イルオキシ）プロピルオキシ］ベンゼン（上記式
（５）においてＲ2が水素原子である化合物）の製造法
として３−（２，６−ジクロロ−４−ベンジルオキシ）
フェノキシ−１−プロピルアルコールと２−クロロ−５
−トリフルオロメチルピリジンと水素化ナトリウムと
を、Ｎ，Ｎ−ジメチルホルムアミド中で反応させる方法
が具体的に記載されている。しかしながら、この方法は
収率が必ずしも十分なものとはいえない。本発明は、工
業的に汎用性が高い化合物を溶媒として用いて式（３）
（式中、Ｒ1はハロゲン原子で置換されていてもよいベ
ンジル基又は３，３−ジハロ−２−プロペニル基を表
し、Ｒ2は水素原子又は塩素原子を表す。）で示される
エーテル化合物を収率よく製造する方法を提供すること
を課題とする。PRIOR ART AND PROBLEM TO BE SOLVED BY THE INVENTION Equation (4) (In the formula, R 2 represents a hydrogen atom or a halogen atom, and R 3 represents a chlorine atom or a bromine atom.) A dihalopropene compound represented by the formula (1) is useful as an active ingredient of insecticides and acaricides. 5) It is known that a compound represented by the formula (wherein R 2 represents a hydrogen atom or a halogen atom) is useful as a production intermediate thereof (JP-A-9-151172). And, in the publication, 1-benzyloxy-3,5-dichloro-4- [3- (5-trifluoromethylpyridine-2
3- (2,6-dichloro-4-benzyloxy) as a method for producing -yloxy) propyloxy] benzene (a compound in which R 2 is a hydrogen atom in the above formula (5))
Phenoxy-1-propyl alcohol and 2-chloro-5
A method for reacting trifluoromethylpyridine with sodium hydride in N, N-dimethylformamide is specifically described. However, this method does not always give a sufficient yield. INDUSTRIAL APPLICABILITY The present invention uses a compound having industrially high versatility as a solvent to obtain a compound of formula (3) (In the formula, R 1 represents a benzyl group or a 3,3-dihalo-2-propenyl group which may be substituted with a halogen atom, and R 2 represents a hydrogen atom or a chlorine atom.) An object of the present invention is to provide a method for producing a high yield.
【０００３】[0003]
【課題を解決するための手段】本発明者等は、上記課題
を解決すべく鋭意検討した結果、工業的に汎用性が高い
炭化水素化合物を溶媒として、後記式（１）で示される
アルコール化合物と後記式（２）で示されるピリジン化
合物とアルカリ金属水素化物とを反応させることによ
り、式（３）で示されるエーテル化合物が収率よく得ら
れることを見出し、本発明を完成した。Means for Solving the Problems As a result of intensive studies to solve the above problems, the present inventors have found that an alcohol compound represented by the following formula (1) using a hydrocarbon compound having high industrial versatility as a solvent. The present invention was completed by finding that the ether compound represented by the formula (3) can be obtained in good yield by reacting the pyridine compound represented by the formula (2) with an alkali metal hydride.
【０００４】すなわち、本発明は、式（１）
（式中、Ｒ1はハロゲン原子で置換されていてもよいベ
ンジル基又は３，３−ジハロ−２−プロペニル基を表
す。）で示されるアルコール化合物と式（２）
（式中、Ｒ2は水素原子又は塩素原子を表す。）で示さ
れるピリジン化合物とアルカリ金属水素化物とを、炭化
水素化合物中で反応させることを特徴とする式（３）
（式中、Ｒ1及びＲ2は前記と同じ意味を表す。）で示さ
れるエーテル化合物の製造法（以下、本発明製造法と記
す。）を提供する。That is, the present invention uses the formula (1) (In the formula, R 1 represents a benzyl group which may be substituted with a halogen atom or a 3,3-dihalo-2-propenyl group.) And the formula (2). (Wherein R 2 represents a hydrogen atom or a chlorine atom) and an alkali metal hydride are allowed to react in a hydrocarbon compound. (In the formula, R 1 and R 2 have the same meanings as described above.) A method for producing an ether compound (hereinafter, referred to as the present invention production method) is provided.
【０００５】[0005]
【発明の実施の形態】本発明において、Ｒ1で示される
ハロゲン原子で置換されていてもよいベンジル基として
は、例えばベンゼン環がハロゲン原子で置換されていて
もよいベンジル基があげられ、具体的には例えば４−ク
ロロベンジル基及びベンジル基があげられる。Ｒ1で示
される３，３−ジハロ−２−プロペニル基としては例え
ば３，３−ジクロロ−２−プロペニル基および３，３−
ジブロモ−２−プロペニル基があげられる。BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, examples of the benzyl group which may be substituted with a halogen atom represented by R 1 include a benzyl group whose benzene ring may be substituted with a halogen atom. Specific examples thereof include a 4-chlorobenzyl group and a benzyl group. Examples of the 3,3-dihalo-2-propenyl group represented by R 1 include 3,3-dichloro-2-propenyl group and 3,3-
An example is a dibromo-2-propenyl group.
【０００６】Ｒ2で示されるハロゲン原子としては、例
えば塩素原子があげられる。Examples of the halogen atom represented by R 2 include chlorine atom.
【０００７】本発明製造法は式（１）で示されるアルコ
ール化合物と式（２）で示されるピリジン化合物とアル
カリ金属水素化物とを、炭化水素化合物中で反応させる
ことを特徴とする。該反応に用いられる炭化水素化合物
としては、ヘキサン、ヘプタン、オクタン、ノナン、デ
カン、３−メチルペンタン、シクロヘキサン、メチルシ
クロへキサン等の脂肪族炭化水素化合物及びトルエン、
キシレン、メシチレン、エチルベンゼン等の芳香族炭化
水素化合物があげられる。反応に用いられる炭化水素化
合物の量は式（１）で示されるアルコール化合物１重量
部に対して通常０．３〜５０重量部の割合であり、中で
も反応速度の点から好ましくは５重量部以下の割合であ
ることが好ましい。該反応において式（１）で示される
アルコール化合物と式（２）で示されるピリジン化合物
との量比は式（１）で示されるアルコール化合物１モル
に対して、式（２）で示されるピリジン化合物が通常
０．９〜３モルの割合である。反応に用いられるアルカ
リ金属水素化物としては、例えば水素化ナトリウムがあ
げられる。反応に用いられるアルカリ金属水素化物の量
は、反応が進行する範囲で変化させることができるが、
式（１）で示されるアルコール化合物１モルに対して通
常０．９モル以上、式（２）で示されるピリジン化合物
１モルに対して１．２モル以下の割合である。該反応は
例えば、アルカリ金属水素化物、式（２）で示されるピ
リジン化合物及び炭化水素化合物の混合物に、式（１）
で示されるアルコール化合物を添加することにより実施
することができる。該反応の反応温度は通常５０〜１０
０℃の範囲であり、反応時間は通常１〜４８時間の範囲
である。該反応の進行状況は、例えば反応混合物を高速
液体クロマトグラフィー等のクロマトグラフィーで分析
することにより確認することができる。反応終了後は、
反応混合物に炭化水素化合物及び食塩水を加えて濾過
し、濾液を分液して得られる有機層を水（必要に応じて
希塩酸等の酸性水）で洗浄した後、濃縮する等の後処理
操作を行うことにより、式（３）で示されるエーテル化
合物を単離することができる。単離した式（３）で示さ
れるエーテル化合物は必要に応じてクロマトグラフィー
等によりさらに精製することもできる。The production method of the present invention is characterized in that an alcohol compound represented by the formula (1), a pyridine compound represented by the formula (2) and an alkali metal hydride are reacted in a hydrocarbon compound. Examples of the hydrocarbon compound used in the reaction include hexane, heptane, octane, nonane, decane, 3-methylpentane, cyclohexane, methylcyclohexane, and other aliphatic hydrocarbon compounds and toluene,
Examples thereof include aromatic hydrocarbon compounds such as xylene, mesitylene, and ethylbenzene. The amount of the hydrocarbon compound used in the reaction is usually 0.3 to 50 parts by weight relative to 1 part by weight of the alcohol compound represented by the formula (1), and preferably 5 parts by weight or less from the viewpoint of reaction rate. Is preferable. In the reaction, the amount ratio of the alcohol compound represented by the formula (1) and the pyridine compound represented by the formula (2) is 1 mol of the alcohol compound represented by the formula (1), and the pyridine compound represented by the formula (2). The amount of the compound is usually 0.9 to 3 mol. Examples of the alkali metal hydride used in the reaction include sodium hydride. The amount of alkali metal hydride used in the reaction can be changed within the range where the reaction proceeds,
The ratio is usually 0.9 mol or more with respect to 1 mol of the alcohol compound represented by the formula (1) and 1.2 mol or less with respect to 1 mol of the pyridine compound represented by the formula (2). The reaction is carried out, for example, by adding a mixture of an alkali metal hydride, a pyridine compound represented by the formula (2) and a hydrocarbon compound,
It can be carried out by adding an alcohol compound represented by. The reaction temperature of the reaction is usually 50 to 10
It is in the range of 0 ° C., and the reaction time is usually in the range of 1 to 48 hours. The progress of the reaction can be confirmed, for example, by analyzing the reaction mixture by chromatography such as high performance liquid chromatography. After the reaction,
A hydrocarbon compound and saline are added to the reaction mixture, the mixture is filtered, and the organic layer obtained by separating the filtrate is washed with water (acidic water such as dilute hydrochloric acid as necessary) and then concentrated. By carrying out, the ether compound represented by the formula (3) can be isolated. The isolated ether compound represented by the formula (3) can be further purified by chromatography or the like, if necessary.
【０００８】本発明製造法により製造することができる
式（６）
（式中、Ｒ2は水素原子又はハロゲン原子を表し、Ｒ4は
ハロゲン原子で置換されていてもよいベンジル基を表
す。）で示されるエーテル化合物は例えば特開平９−１
５１１７２号公報に記載の方法に準じて式（７）
（式中、Ｒ2は水素原子又はハロゲン原子を表し、Ｒ5は
３，３−ジハロ−２−プロペニル基を表す。）で示され
るジハロプロペン化合物に変換することができる。Formula (6) that can be produced by the production method of the present invention An ether compound represented by the formula (wherein R 2 represents a hydrogen atom or a halogen atom and R 4 represents a benzyl group which may be substituted with a halogen atom) is, for example, JP-A-9-1.
Formula (7) according to the method described in Japanese Patent No. 51172. (In the formula, R 2 represents a hydrogen atom or a halogen atom, and R 5 represents a 3,3-dihalo-2-propenyl group.), And can be converted into a dihalopropene compound.
【０００９】式（１）で示されるアルコール化合物は例
えば特開平９−１５１１７２号公報に記載の方法又はそ
れに準じた方法で製造することができる。The alcohol compound represented by the formula (1) can be produced, for example, by the method described in JP-A-9-151172 or a method analogous thereto.
【００１０】[0010]
【実施例】以下、実施例により本発明をさらに詳しく説
明するが、本発明はこれらの例に限定されるものではな
い。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples.
【００１１】実施例１
水素化ナトリウム（純度：６４％）２０重量部、２−ク
ロロ−５−トリフルオロメチルピリジン（純度：１００
％）１１０重量部及びヘキサン１００重量部の混合物に
７２℃で、３−（２，６−ジクロロ−４−ベンジルオキ
シ）フェノキシプロピルアルコール（純度：９９％）を
約１４．３重量部ずつ、１時間毎に７回注加した（注加
した３−（２，６−ジクロロ−４−ベンジルオキシ）フ
ェノキシプロピルアルコールの合計量は１００重量
部）。その後、加熱還流温度で１２時間攪拌した。続い
て、反応混合物を１０℃まで冷却し、ヘキサン１５０重
量部、２０％食塩水２００重量部およびセライト１８重
量部を加えて濾過した。濾過残渣をヘキサン１５０重量
部で洗浄した。得られた濾液を分液した。有機層を３％
塩酸９４重量部および水９４重量部で順次洗浄し、減圧
下で濃縮して、３，５−ジクロロ−１−ベンジルオキシ
−４−［３−（５−トリフルオロメチルピリジン−２−
イルオキシ）プロピルオキシ］ベンゼン １３８重量部
（純度：９３％、収率：８９％）を得た。Example 1 20 parts by weight of sodium hydride (purity: 64%), 2-chloro-5-trifluoromethylpyridine (purity: 100
%) 110 parts by weight and hexane 100 parts by weight at 72 ° C., about 14.3 parts by weight of 3- (2,6-dichloro-4-benzyloxy) phenoxypropyl alcohol (purity: 99%), 1 part each. It was added 7 times every hour (the total amount of 3- (2,6-dichloro-4-benzyloxy) phenoxypropyl alcohol added was 100 parts by weight). Then, the mixture was stirred at a heating reflux temperature for 12 hours. Subsequently, the reaction mixture was cooled to 10 ° C., 150 parts by weight of hexane, 200 parts by weight of 20% saline and 18 parts by weight of Celite were added and filtered. The filtration residue was washed with 150 parts by weight of hexane. The obtained filtrate was separated. 3% organic layer
It was washed successively with 94 parts by weight of hydrochloric acid and 94 parts by weight of water, concentrated under reduced pressure and concentrated to give 3,5-dichloro-1-benzyloxy-4- [3- (5-trifluoromethylpyridine-2-
138 parts by weight (purity: 93%, yield: 89%) were obtained.
【００１２】３，５−ジクロロ−１−ベンジルオキシ−
４−［３−（５−トリフルオロメチルピリジン−２−イ
ルオキシ）プロピルオキシ］ベンゼン
3,5-dichloro-1-benzyloxy-
4- [3- (5-trifluoromethylpyridin-2-yloxy) propyloxy] benzene
【００１３】実施例２
水素化ナトリウム（純度：６４％）１４重量部、２−ク
ロロ−５−トリフルオロメチルピリジン（純度：９８
％）１０１重量部及びヘキサン８６重量部の混合物に７
２℃で３−［２，６−ジクロロ−４−（３，３−ジクロ
ロ−２−プロペニルオキシ）］フェノキシプロピルアル
コール１００重量部（純度９３％）を６時間かけて滴下
した。滴下終了後、７１℃〜７４℃で１２時間攪拌し
た。その後、反応混合物を１０℃に冷却し、ヘキサン１
５０重量部、２０％食塩水２００重量部およびセライト
１８重量部を加えて濾過した。濾過残渣をヘキサン１５
０重量部で洗浄した。得られた濾液を分液した。有機層
を３％塩酸９４重量部および水９４重量部で順次洗浄
し、減圧下で濃縮して３，５−ジクロロ−１−（３，３
−ジクロロ−２−プロペニルオキシ）−４−［３−（５
−トリフルオロメチルピリジン−２−イルオキシ）プロ
ピルオキシ］ベンゼンを１３３重量部（純度：８８％、
収率：８８％）を得た。Example 2 14 parts by weight of sodium hydride (purity: 64%), 2-chloro-5-trifluoromethylpyridine (purity: 98)
%) 7 to a mixture of 101 parts by weight and 86 parts by weight of hexane.
100 parts by weight of 3- [2,6-dichloro-4- (3,3-dichloro-2-propenyloxy)] phenoxypropyl alcohol (purity 93%) was added dropwise at 2 ° C over 6 hours. After the completion of dropping, the mixture was stirred at 71 ° C to 74 ° C for 12 hours. Then the reaction mixture is cooled to 10 ° C. and hexane 1
50 parts by weight, 200 parts by weight of 20% saline and 18 parts by weight of Celite were added and filtered. The filtration residue is hexane 15
Washed with 0 parts by weight. The obtained filtrate was separated. The organic layer was washed successively with 94% by weight of 3% hydrochloric acid and 94% by weight of water and concentrated under reduced pressure to give 3,5-dichloro-1- (3,3
-Dichloro-2-propenyloxy) -4- [3- (5
-Trifluoromethylpyridin-2-yloxy) propyloxy] benzene 133 parts by weight (purity: 88%,
Yield: 88%) was obtained.
【００１４】実施例３
水素化ナトリウム（純度：６４％）１４重量部、２−ク
ロロ−５−トリフルオロメチルピリジン（純度：９７
％）１００重量部及びヘプタン１３０重量部の混合物に
６０℃で３−［２，６−ジクロロ−４−（３，３−ジク
ロロ−２−プロペニルオキシ）］フェノキシ−１−プロ
ピルアルコール１００重量部（純度９３％）を６時間か
けて滴下した。滴下終了後、６５℃で２６時間攪拌し
た。その後、反応混合物を１０℃に冷却し、ヘプタン１
３３重量部、２０％食塩水１９５重量部およびセライト
１８重量部を加えて濾過した。濾過残渣をヘプタン１４
６重量部で洗浄した。得られた濾液を分液した。有機層
を３％塩酸９３重量部および水９３重量部で順次洗浄
し、３，５−ジクロロ−１−（３，３−ジクロロ−２−
プロペニルオキシ）−４−［３−（５−トリフルオロメ
チルピリジン−２−イルオキシ）プロピルオキシ］ベン
ゼンのヘプタン溶液５１２重量部（純度：２２％、収
率：８５％）を得た。Example 3 14 parts by weight of sodium hydride (purity: 64%), 2-chloro-5-trifluoromethylpyridine (purity: 97)
%) 100 parts by weight and 130 parts by weight of heptane in a mixture at 60 ° C. 100 parts by weight of 3- [2,6-dichloro-4- (3,3-dichloro-2-propenyloxy)] phenoxy-1-propyl alcohol ( (Purity 93%) was added dropwise over 6 hours. After the completion of dropping, the mixture was stirred at 65 ° C for 26 hours. Then the reaction mixture is cooled to 10 ° C. and heptane 1
33 parts by weight, 195 parts by weight of 20% saline and 18 parts by weight of Celite were added and filtered. The filter residue is heptane 14
Washed with 6 parts by weight. The obtained filtrate was separated. The organic layer was washed successively with 93 parts by weight of 3% hydrochloric acid and 93 parts by weight of water to give 3,5-dichloro-1- (3,3-dichloro-2-
512 parts by weight of a heptane solution of propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propyloxy] benzene was obtained (purity: 22%, yield: 85%).
【００１５】３，５−ジクロロ−１−（３，３−ジクロ
ロ−２−プロペニルオキシ）−４−［３−（５−トリフ
ルオロメチルピリジン−２−イルオキシ）プロピルオキ
シ］ベンゼン
3,5-Dichloro-1- (3,3-dichloro-2-propenyloxy) -4- [3- (5-trifluoromethylpyridin-2-yloxy) propyloxy] benzene
【００１６】上記実施例において、目的物の純度分析は
以下の条件で行った。
高速液体クロマトグラフィー
カラム：Ｌ−ｃｏｌｕｍｎ（化学物質評価研究機構製）
移動層：アセトニトリル／水＝８／２
移動層流量：１ｍｌ／分
カラム温度：４０℃
検出器：紫外吸光光度計（波長２７０ｎｍ）
内部標準：フタル酸 ジ（２−エチルヘキシル）In the above examples, the purity analysis of the target substance was carried out under the following conditions. High-performance liquid chromatography column: L-column (manufactured by Chemicals Evaluation and Research Institute) Mobile bed: acetonitrile / water = 8/2 Mobile bed flow rate: 1 ml / min Column temperature: 40 ° C Detector: UV absorptiometer (wavelength 270 nm) Internal standard: Di (2-ethylhexyl) phthalate
【００１７】[0017]
【発明の効果】本発明製造法によれば工業的に汎用性が
高い炭化水素化合物を溶媒として用いて、式（３）で示
されるエーテル化合物を高収率で得ることができる。According to the production method of the present invention, an ether compound represented by the formula (3) can be obtained in a high yield by using a hydrocarbon compound which is industrially widely used as a solvent.
───────────────────────────────────────────────────── フロントページの続き Ｆターム(参考） 4C055 AA01 BA02 BA42 BB02 BB08 CA02 CA06 CA13 DA01 FA11 FA37 ─────────────────────────────────────────────────── ─── Continued front page F-term (reference) 4C055 AA01 BA02 BA42 BB02 BB08 CA02 CA06 CA13 DA01 FA11 FA37
Claims (4)
ンジル基又は３，３−ジハロ−２−プロペニル基を表
す。）で示されるアルコール化合物と式（２） （式中、Ｒ2は水素原子又は塩素原子を表す。）で示さ
れるピリジン化合物とアルカリ金属水素化物とを、炭化
水素化合物中で反応させることを特徴とする式（３） （式中、Ｒ1及びＲ2は前記と同じ意味を表す。）で示さ
れるエーテル化合物の製造法。1. A formula (1) (In the formula, R 1 represents a benzyl group which may be substituted with a halogen atom or a 3,3-dihalo-2-propenyl group.) And the formula (2). (Wherein R 2 represents a hydrogen atom or a chlorine atom) and an alkali metal hydride are allowed to react in a hydrocarbon compound. (In the formula, R 1 and R 2 have the same meanings as described above.) A process for producing an ether compound.
あることを特徴とする請求項１記載のエーテル化合物の
製造法。2. The method for producing an ether compound according to claim 1, wherein the hydrocarbon compound is an aliphatic hydrocarbon compound.
あることを特徴とする請求項１記載のエーテル化合物の
製造法。3. The process for producing an ether compound according to claim 1, wherein the hydrocarbon compound is hexane or heptane.
する請求項１〜３いずれか１項記載のエーテル化合物の
製造法。4. The process for producing an ether compound according to claim 1, wherein the reaction is carried out at 50 to 100 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002142616A JP2003335757A (en) | 2002-05-17 | 2002-05-17 | Method for producing ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002142616A JP2003335757A (en) | 2002-05-17 | 2002-05-17 | Method for producing ether compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003335757A true JP2003335757A (en) | 2003-11-28 |
Family
ID=29702855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002142616A Pending JP2003335757A (en) | 2002-05-17 | 2002-05-17 | Method for producing ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2003335757A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116178249A (en) * | 2023-02-22 | 2023-05-30 | 北京亦农生物科技有限公司 | Ether derivative with insecticidal and acaricidal activities as well as preparation method and application thereof |
-
2002
- 2002-05-17 JP JP2002142616A patent/JP2003335757A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116178249A (en) * | 2023-02-22 | 2023-05-30 | 北京亦农生物科技有限公司 | Ether derivative with insecticidal and acaricidal activities as well as preparation method and application thereof |
| CN116178249B (en) * | 2023-02-22 | 2024-02-09 | 北京亦农生物科技有限公司 | Ether derivative with insecticidal and acaricidal activities as well as preparation method and application thereof |
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