JP2771882B2 - Process for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate - Google Patents
Process for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolateInfo
- Publication number
- JP2771882B2 JP2771882B2 JP2058678A JP5867890A JP2771882B2 JP 2771882 B2 JP2771882 B2 JP 2771882B2 JP 2058678 A JP2058678 A JP 2058678A JP 5867890 A JP5867890 A JP 5867890A JP 2771882 B2 JP2771882 B2 JP 2771882B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- oxo
- dialkyl
- thiazolidinyl
- phosphonothiolate
- 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.)
- Expired - Lifetime
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、殺虫、殺ダニ、殺線虫、殺土壌害虫剤の活
性成分として有用なS,O−ジアルキル（２−オキソ−３
−チアゾリジニル）ホスホノチオレート（以下BEOTP）
の工業的有利な製造法に関する。The present invention relates to S, O-dialkyl (2-oxo-3) useful as an active ingredient of insecticides, miticides, nematicides and soil pesticides.
-Thiazolidinyl) phosphonothiolate (BEOTP)
For an industrially advantageous production method.
従来、BEOTPの製造方法については、特開昭60−13659
0公報、同63−88193公報などにおいて不活性溶媒及び塩
基性物質の存在下に２−オキソ−３−チアゾリジン（以
下２−OT）とS,O−ジアルキルホスホロクロリドチオレ
ート（以下BEP）とを反応させてBEOTPを製造する方法が
記載され公知である。前者には塩基性物質として有機リ
チウム化合物、無機塩基及び有機塩基が列挙されている
ものの、具体的な製造例としては工業的実施に適当でな
いｎ−ブチルリチウムが使用されているに過ぎず、この
ため後者では金属ナトリウムを使用（具体的な製造例で
は２−OTとBEPとを等モル付近で反応）することによっ
て工業的実施の適用性が或程度改善されたが、金属ナト
リウムは高価であり、かつ反応時に水素ガスを発生する
などその取扱いに危険が伴ない、しかも、溶媒に均一に
溶融、分散させる必要があって操作が煩雑であり、生産
性が低下するため、依然として改良が求められている。Conventionally, a method for producing BEOTP has been disclosed in JP-A-60-13659.
Publication No. 0,63-88193, etc., in the presence of an inert solvent and a basic substance, 2-oxo-3-thiazolidine (hereinafter referred to as 2-OT) and S, O-dialkyl phosphorochloride thiolate (hereinafter referred to as BEP). The method of producing BEOTP by reacting is described and known. In the former, organolithium compounds, inorganic bases and organic bases are listed as basic substances, but n-butyllithium, which is not suitable for industrial practice, is used as a specific production example. Therefore, in the latter case, the applicability of industrial practice was improved to some extent by using metallic sodium (in a specific production example, reaction between 2-OT and BEP near equimolar), but metallic sodium is expensive. In addition, there is no danger in handling such as generation of hydrogen gas during the reaction, and it is necessary to uniformly dissolve and disperse in a solvent, and the operation is complicated, and the productivity is reduced. ing.
本出願人は、BEPに対して一定以上の２−OTを存在さ
せた反応系にて工業的適用性の高いアルカリ金属又はア
ルカリ土類金属の各水酸化物を用いることにより、BEOT
Pを良好に製造する方法について先に特願昭63−227757
として特許出願をおこなった。The present applicant has proposed a BEOT by using an alkali metal or alkaline earth metal hydroxide having high industrial applicability in a reaction system in which a certain amount or more of 2-OT is present with respect to BEP.
The method for producing P well is described in Japanese Patent Application No. 63-227757.
Filed a patent application.
本発明者達はこの方法に相間移動触媒を用いることに
より、反応原料を溶媒中に均一に分散させ、特に２−OT
を反応理論量に比し過剰に存在させなくても良好に反応
が進み目的物の生成率は向上するため、従来法に比し工
業的に有利になり、一層改良できることを見出して本発
明を完成するに至った。By using a phase transfer catalyst in this method, the present inventors disperse the reaction raw materials uniformly in a solvent,
It is found that the reaction proceeds satisfactorily even if not excessively present compared to the theoretical amount of the reaction, and the production rate of the target product is improved. It was completed.
即ち本発明は、不活性溶媒及び塩基性物質の存在下、
２−オキソ−３−チアゾリジンとS,O−ジアルキルホス
ホロクロリドチオレートとを反応させてS,O−ジアルキ
ル（２−オキソ−３−チアゾリジニル）ホスホノチオレ
ートを製造する方法において、塩基性物質としてアルカ
リ金属水酸化物又はアルカリ土類金属水酸化物を用い、
かつ相間移動触媒としてホスホニウム塩又はアンモニウ
ム塩を存在させて反応をおこなうことを特徴とする。That is, the present invention, in the presence of an inert solvent and a basic substance,
In a method for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate by reacting 2-oxo-3-thiazolidine with S, O-dialkyl phosphorochloride thiolate, a basic substance is used. Using an alkali metal hydroxide or an alkaline earth metal hydroxide,
The reaction is carried out in the presence of a phosphonium salt or an ammonium salt as a phase transfer catalyst.
本発明において使用される相間移動触媒は、次の一般
式で表わされるホスホニウム塩又はアンモニウム塩であ
る。The phase transfer catalyst used in the present invention is a phosphonium salt or an ammonium salt represented by the following general formula.
一般式 〔R1 R2 R3 R4 X〕+Y- 式中R1,R2,R3及びR4は置換されてもよいアルキル基、シ
クロアルキル基又は置換されてもよいフェニル基であ
り、Ｘは窒素原子又はリン原子である。Ｙは水酸基、ハ
ロゲン原子、有機酸残基又は無機酸残基である。置換さ
れてもよいアルキル基又は同フェニル基の置換基として
はヒドロキシ基、ハロゲン原子、アルコキン基、アリー
ル基などが挙げられ、有機酸残基の有機酸としては蟻
酸、酢酸、蓚酸などのカルボン酸、メタンスルホン酸、
エタンスルホン酸、ベンゼンスルホン酸などのスルホン
酸などが挙げられ、無機酸残基の無機酸としては硫酸、
重硫酸、硝酸、リン酸、炭酸、重炭酸などが挙げられ
る。Formula [R 1 R 2 R 3 R 4 X ] + Y - wherein R 1, R 2, R 3 and R 4 may be substituted alkyl group, a cycloalkyl group or an optionally substituted phenyl group And X is a nitrogen atom or a phosphorus atom. Y is a hydroxyl group, a halogen atom, an organic acid residue or an inorganic acid residue. Examples of the substituent of the alkyl group or the phenyl group which may be substituted include a hydroxy group, a halogen atom, an alkyne group, and an aryl group. , Methanesulfonic acid,
Ethanesulfonic acid, sulfonic acids such as benzenesulfonic acid and the like, and as the inorganic acid of the inorganic acid residue, sulfuric acid,
Examples include bisulfuric acid, nitric acid, phosphoric acid, carbonic acid, and bicarbonate.
本発明において一般に相間移動触媒は２−OT又はBEP
が不活性溶媒に溶解した油相と塩基性物質又は中間生成
物２−OTの塩からなる固相と或は反応の際水を存在させ
る場合それらの水相との２相又は３相の間での相互作用
により、これらを油相に溶解させることによって、反応
の仲立ちをすると考えられ、それにより２−OTの塩の生
成を促進し、この塩とBEPとの反応によるBEOTPの生成を
増進すると考えられる。相間移動触媒の具体例としては
テトラ−ｎ−ブチルホスホニウムブロマイド、トリフェ
ニルデシルホスホニウムアイオダイド、トリブチルヘキ
サデシルホスホニウムブロマイドなどのホスホニウム
塩、ベンジルトリブチルアンモニウムクロライド、テト
ラブチルアンモニウムブロマイド、トリオクチルアンモ
ニウムクロライドなどのアンモニウム塩が挙げられる
が、ホスホニウム塩がアンモニウムに比し望ましく、な
かでもテトラ−ｎ−ブチルホスホニウムブロマイドが望
ましい。In the present invention, the phase transfer catalyst is generally 2-OT or BEP
Between the two or three phases of an oil phase dissolved in an inert solvent and a solid phase consisting of a salt of a basic substance or an intermediate product 2-OT or, if water is present during the reaction, their aqueous phases Is considered to mediate the reaction by dissolving them in the oil phase, thereby promoting the formation of 2-OT salt and enhancing the production of BEOTP by the reaction of this salt with BEP. It is thought that. Specific examples of the phase transfer catalyst include tetra-n-butylphosphonium bromide, phosphonium salts such as triphenyldecylphosphonium iodide, tributylhexadecylphosphonium bromide, benzyltributylammonium chloride, tetrabutylammonium bromide, and ammonium such as trioctylammonium chloride. Salts may be mentioned, and a phosphonium salt is more preferable than ammonium, and among them, tetra-n-butylphosphonium bromide is more preferable.
本発明方法において使用するアルカリ金属水酸化物又
はアルカリ土類金属水酸化物としては例えば水酸化リチ
ウム、水酸化ナトリウム、水酸化カリウム、水酸化マグ
ネシウム、水酸化カルシウムなどが挙げられるが、望ま
しくは水酸化ナトリウム、水酸化カリウム、より望まし
くは水酸化ナトリウムである。また前記不活性溶媒とし
ては本発明の反応の進行に対して実質的に影響を与えな
いものであり、例えばベンゼン、トルエン、キシレン、
クロロベンゼンなどの芳香族炭化水素類、塩化メチレ
ン、クロロホルム、ジクロロエタン、シクロヘキサンな
どの環状又は非環状脂肪族炭化水素類、ジオキサン、ジ
エチルエーテル、メチルエチルエーテル、テトラヒドロ
フランなどのエーテル類、水などが挙げられるが、望ま
しくはトルエン、ジクロロエタン、テトラヒドロフラン
などであり、より望ましくはトルエンである。Examples of the alkali metal hydroxide or alkaline earth metal hydroxide used in the method of the present invention include lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, and the like. Sodium oxide, potassium hydroxide, more preferably sodium hydroxide. Further, the inert solvent does not substantially affect the progress of the reaction of the present invention, for example, benzene, toluene, xylene,
Aromatic hydrocarbons such as chlorobenzene, cyclic or non-cyclic aliphatic hydrocarbons such as methylene chloride, chloroform, dichloroethane and cyclohexane; ethers such as dioxane, diethyl ether, methyl ethyl ether and tetrahydrofuran; and water. , Preferably toluene, dichloroethane, tetrahydrofuran and the like, and more preferably toluene.
本発明においては、不活性溶媒、塩基性物質、相間移
動触媒、２−OT及びBEPを添加する順序は特に問わずい
ずれの添加順序によっても反応は進行するが、不活性溶
媒に２−OTを溶解させ次いで塩基性物質更に相間移動触
媒を加えるか或は相間移動触媒さらに塩基性物質を加
え、然る後にBEPを加えて反応させる方法が反応操作、
反応進行上望ましい。また、その際少量の水を存在させ
て反応原料を溶媒中により均一に分散させることもで
き、例えば塩基性物質をその水溶液又は水分散液として
加えたり或いは塩基性物質を加えるときに水を別に加え
たりすることもできる。しかしながら水を存在させず
に、塩基性物質を固体のまま或は必要ならば粉砕したも
のを使用して反応をおこなう方が、目的物の純度、収率
が向上するので望ましい。本発明では２−OTはBEP1モル
に対し0.8〜３モル望ましくは１〜２モル使用される。
反応の際水を使用しない場合２−OTは反応理論量に対し
著しく過剰に使用されることはないので、反応生成物か
ら２−OTを回収する煩雑な処理、操作は必要でないか或
は必要であってもそれらは簡便なものになる。また２−
OTの使用量は反応操作、循環操作などの工業的実施面を
考慮して自ずと適切な値が決定される。塩基性物質の使
用量は反応条件の相違により一概に規定できないが、普
通 BEP1モルに対し0.8〜２モル望ましくは１〜1.5モル
であり、同様に不活性溶媒の使用量は普通BEP1重量部に
対し、２〜30倍望ましくは３〜10倍量であり、相間移動
触媒の使用量は BEP1モルに対し0.1〜30g望ましくは0.
5〜10gである。In the present invention, the reaction proceeds in any order of addition of the inert solvent, the basic substance, the phase transfer catalyst, 2-OT and BEP, regardless of the order of addition. A method of reacting by dissolving and then adding a basic substance and a phase transfer catalyst further, or adding a phase transfer catalyst and a basic substance and then adding BEP and reacting,
Desirable for reaction progress. Further, at that time, a small amount of water may be present to more uniformly disperse the reaction raw materials in the solvent.For example, when a basic substance is added as an aqueous solution or an aqueous dispersion or when a basic substance is added, water is separately added. You can also add. However, it is desirable to carry out the reaction without using water and using a basic substance as a solid or, if necessary, a pulverized substance, since the purity and yield of the target substance are improved. In the present invention, 2-OT is used in an amount of 0.8 to 3 moles, preferably 1 to 2 moles per mole of BEP.
When water is not used in the reaction, 2-OT is not used in an excessive amount relative to the stoichiometric amount of the reaction. Therefore, complicated processing and operation for recovering 2-OT from the reaction product are not necessary or necessary. Even so, they become simple. Also 2-
The amount of OT used is naturally determined to be an appropriate value in view of industrial aspects such as a reaction operation and a circulation operation. The amount of the basic substance used cannot be specified unconditionally due to the difference in the reaction conditions, but is usually 0.8 to 2 mol, preferably 1 to 1.5 mol per mol of BEP, and the amount of the inert solvent is usually 1 part by weight of BEP. On the other hand, the amount is 2 to 30 times, preferably 3 to 10 times, and the amount of the phase transfer catalyst used is 0.1 to 30 g, preferably 0.1 to 30 mol per mol of BEP.
5 to 10 g.
本発明の反応は２−OTの塩の生成反応並びに２−OTの
塩とBEPから目的のBEOTPを生成する反応からなり、それ
らの反応温度及び反応時間は他の反応条件の相違により
一概に規定できないが、前者の反応は温度−50℃〜＋10
0℃望ましくは−10℃〜＋40℃で普通0.5〜50時間望まし
くは１〜20時間で終了し、後者の反応は温度−80℃〜＋
50℃望ましくは−30℃〜＋20℃で普通0.5〜50時間望ま
しくは１〜20時間で終了する。反応生成物は一般に水洗
いした後溶媒を留去すれば目的のBEOTPが取得できる。
一方反応の際水を使用したときには反応生成物から分離
した水相には２−OTが溶解しているので、必要に応じ水
相に塩酸を加えて、PH4までの酸性状態にして、塩化メ
チレンで抽出した後抽出相から塩化メチレンを留去すれ
ば２−OTが回収できるので、このものを循環して再度反
応に供することができる。本発明方法によれば目的のBE
OTPは高純度でかつ高収率で製造することができる。The reaction of the present invention comprises a reaction for producing a salt of 2-OT and a reaction for producing a desired BEOTP from a salt of 2-OT and BEP, and their reaction temperature and reaction time are stipulated by differences in other reaction conditions. Although not possible, the former reaction is performed at a temperature between -50 ° C and + 10 ° C.
The reaction is completed at 0 ° C, preferably -10 ° C to + 40 ° C, usually for 0.5 to 50 hours, preferably for 1 to 20 hours.
The reaction is usually completed at 50 ° C, preferably -30 ° C to + 20 ° C, for 0.5 to 50 hours, preferably for 1 to 20 hours. In general, the desired BEOTP can be obtained by washing the reaction product with water and then distilling off the solvent.
On the other hand, when water is used in the reaction, 2-OT is dissolved in the aqueous phase separated from the reaction product, and if necessary, hydrochloric acid is added to the aqueous phase to make it acidic to PH4, and methylene chloride is added. After extracting with, methylene chloride is distilled off from the extracted phase, so that 2-OT can be recovered. This can be recycled and used again for the reaction. According to the method of the present invention, the desired BE
OTP can be produced with high purity and high yield.
次に本発明の実施例を記載する。 Next, examples of the present invention will be described.
実施例1: ２−オキソ−３−チアゾリジン1.2モルをトルエン１
に溶解し、室温で固体水酸化ナトリウム1.1モルを加
えて４時間撹拌した。反応液に、テトラ−ｎ−ブチルホ
スホニウムブロマイド5gを加えて冷却した。−10℃で、
この反応液に、Ｓ−sec−ブチル Ｏ−エチルホスホロ
クロリドチオレート１モルを２時間かけて添加した。同
温度で更に１時間撹拌しながら反応させた後、反応液を
水で３回洗浄し、溶媒を留去してＳ−sec−ブチル Ｏ
−エチル（２−オキソ−３−チアゾリジニル）ホスホノ
チオレート274gを得た。このものの純度は94.9％であ
り、収率は96.7％であった。Example 1: 1.2 mol of 2-oxo-3-thiazolidine was added to toluene 1
, And 1.1 mol of solid sodium hydroxide was added at room temperature, followed by stirring for 4 hours. 5 g of tetra-n-butylphosphonium bromide was added to the reaction solution, followed by cooling. At -10 ° C,
To this reaction solution, 1 mol of S-sec-butyl O-ethyl phosphorochloride thiolate was added over 2 hours. After further reacting with stirring at the same temperature for 1 hour, the reaction solution was washed three times with water, and the solvent was distilled off to remove S-sec-butyl O.
274 g of -ethyl (2-oxo-3-thiazolidinyl) phosphonothiolate were obtained. Its purity was 94.9% and yield was 96.7%.
実施例2: ２−オキソ−３−チアゾリジン1.1モルをトルエン１
に溶解し、テトラ−ｎ−ブチルホスホニウムブロマイ
ド2gを加えた後、固体水酸化ナトリウム1.05モルを加え
て４時間撹拌した。−10℃で、この反応液に、Ｓ−sec
−ブチル Ｏ−エチルホスホロクロリドチオレート１モ
ルを1.5時間かけて添加した。同温度で更に１時間撹拌
しながら反応させた後、反応液を水で３回洗浄し、溶媒
を留去して、Ｓ−sec−ブチル Ｏ−エチル（２−オキ
ソ−３−チアゾリジニル）ホスホノチオレート271gを得
た。このものの純度は94.4％であり、収率は95.6％であ
った。Example 2: 1.1 mol of 2-oxo-3-thiazolidine was added to toluene 1
After adding 2 g of tetra-n-butylphosphonium bromide, 1.05 mol of solid sodium hydroxide was added, and the mixture was stirred for 4 hours. At −10 ° C., S-sec
1 mol of -butyl O-ethyl phosphorochloride thiolate was added over 1.5 hours. After further reacting with stirring at the same temperature for 1 hour, the reaction solution was washed three times with water, and the solvent was distilled off to give S-sec-butyl O-ethyl (2-oxo-3-thiazolidinyl) phosphonothio. A rate of 271 g was obtained. Its purity was 94.4% and yield was 95.6%.
実施例3: ２−オキソ−３−チアゾリジン1.1モルをトルエン１
に溶解し、テトラフェニルホスホニウムブロマイド3g
を加えた後、固体水酸化ナトリウム1.05モルを加えて５
時間撹拌した。−10℃でこの反応液に、Ｓ−sec−ブチ
ル Ｏ−エチルホスホロクロリドチオレート１モルを１
時間かけて添加した。同温度で更に１時間撹拌しながら
反応させた後、反応液を水で３回洗浄し、溶媒を留去し
て、Ｓ−sec−ブチル Ｏ−エチル（２−オキソ−３−
チアゾリジニル）ホスホノチオレート256gを得た。この
ものの純度は90.1％であり、収率は90.3％であった。Example 3 1.1 mol of 2-oxo-3-thiazolidine was added to toluene 1
3 g of tetraphenylphosphonium bromide
After addition of 1.05 mol of solid sodium hydroxide,
Stirred for hours. At -10 ° C, 1 mol of S-sec-butyl O-ethyl phosphorochloride thiolate was added to this reaction solution in an amount of 1 mol.
Added over time. After further reacting at the same temperature with stirring for 1 hour, the reaction solution was washed three times with water, and the solvent was distilled off to give S-sec-butyl O-ethyl (2-oxo-3-
256 g of thiazolidinyl) phosphonothiolate were obtained. Its purity was 90.1% and yield was 90.3%.
実施例4: ２−オキソ−３−チアゾリジン20.6g（0.20モル）を
トルエン130mlで溶解し、ベンジルトリブチルアンモニ
ウムクロライド0.86gを加え０℃に冷却した。この溶液
を撹拌しながら50％の水酸化ナトリウム水溶液0.11モル
を30℃以下で滴下した。滴下終了後約15分間撹拌した後
この溶液を０℃に冷却した。次に、Ｓ−sec−ブチル
O,O−ジエチルホスホロチオレートを５％含むＳ−sec−
ブチル Ｏ−エチルホスホロクロリドチオレート21.7g
（0.095モル）を撹拌しながら、０℃で50分間かけて滴
下した。滴下終了後、０℃で約60分間撹拌しながら反応
させた。反応終了後、反応液を100mlで３回洗浄した後
溶媒を留去し、油状のＳ−sec−ブチル Ｏ−エチル
（２−オキソ−３−チアゾリジニル）ホスホノチオレー
ト生成物26.2gを得た。このものは純度88.9％であり、
収率は97.5％であった。Example 4: 2-oxo-3-thiazolidine (20.6 g, 0.20 mol) was dissolved in toluene (130 ml), benzyltributylammonium chloride (0.86 g) was added, and the mixture was cooled to 0 ° C. While stirring this solution, 0.11 mol of a 50% aqueous sodium hydroxide solution was added dropwise at 30 ° C. or lower. After stirring for about 15 minutes after completion of the dropwise addition, the solution was cooled to 0 ° C. Next, S-sec-butyl
S-sec- containing 5% O, O-diethyl phosphorothiolate
Butyl O-ethyl phosphorochloride thiolate 21.7 g
(0.095 mol) was added dropwise at 0 ° C. over 50 minutes with stirring. After the completion of the dropwise addition, the reaction was carried out at 0 ° C. with stirring for about 60 minutes. After completion of the reaction, the reaction solution was washed three times with 100 ml, and then the solvent was distilled off to obtain oily S-sec-butyl O-ethyl.
26.2 g of (2-oxo-3-thiazolidinyl) phosphonothiolate product were obtained. This is 88.9% pure,
The yield was 97.5%.
本発明によれば２−オキソ−３−チアゾリジンとS,O
−ジアルキルホスホロクロリドチオレートとを不活性溶
媒の存在下に反応させて目的物S,O−ジアルキル（２−
オキソ−３−チアゾリジニル）ホスホノチオレートを製
造する方法において、塩基性物質としてアルカリ金属又
はアルカリ土類金属の各水酸化物を使用し、かつ一定の
相間移動触媒を使用することにより目的物を高い生成率
で製造できるので、工業的実施面で従来法に比較して有
利である。According to the present invention, 2-oxo-3-thiazolidine and S, O
-Dialkyl phosphorochloride thiolate in the presence of an inert solvent to give the desired product S, O-dialkyl (2-
In the process for producing oxo-3-thiazolidinyl) phosphonothiolate, the desired product is improved by using each hydroxide of an alkali metal or an alkaline earth metal as a basic substance and using a certain phase transfer catalyst. Since it can be produced at a production rate, it is advantageous in terms of industrial implementation as compared with the conventional method.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 浅井 信好 三重県四日市市石原町１番地 石原産業 株式会社四日市工場内 (72)発明者 奈部川 修吉 東京都江東区亀戸９丁目15番１号 日本 化学工業株式会社研究開発部内 (72)発明者 大坪 格 東京都江東区亀戸９丁目15番１号 日本 化学工業株式会社研究開発部内 (72)発明者 金沢 昭彦 東京都江東区亀戸９丁目15番１号 日本 化学工業株式会社研究開発部内 (56)参考文献 特開 平２−78692（ＪＰ，Ａ) 特許2565381（ＪＰ，Ｂ２) (58)調査した分野(Int.Cl.6，ＤＢ名) C07F 9/6539 B01J 31/02 C07B 61/00──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Nobuyoshi Asai 1 Ishiharacho, Yokkaichi-shi, Mie Ishihara Sangyo Yokkaichi Plant (72) Inventor Shukichi Nabegawa 9-15-1, Kameido, Koto-ku, Tokyo Japan Chemical Industry Co., Ltd. Research and Development Department (72) Inventor Tadashi Otsubo 9-15-1, Kameido, Koto-ku, Tokyo Japan Chemical Industry Co., Ltd. Research and Development Department (72) Inventor Akihiko Kanazawa 9-15 Kameido, Koto-ku, Tokyo No. 1 Japan Chemical Industry Co., Ltd. Research and Development Department (56) References JP-A-2-78692 (JP, A) Patent 2565381 (JP, B2) (58) Fields investigated (Int. Cl. 6 , DB name) C07F 9/6539 B01J 31/02 C07B 61/00
Claims (1)
オキソ−３−チアゾリジンとS,O−ジアルキルホスホロ
クロリドチオレートとを反応させてS,O−ジアルキル
（２−オキソ−３−チアゾリジニル）ホスホノチオレー
トを製造する方法において、塩基性物質としてアルカリ
金属水酸化物又はアルカリ土類金属水酸化物を用い、か
つ相間移動触媒としてホスホニウム塩又はアンモニウム
塩を存在させて反応をおこなうことを特徴とするS,O−
ジアルキル（２−オキソ−３−チアゾリジニル）ホスホ
ノチオレートの製造法。1. The method according to claim 1, wherein said solvent is an inert solvent and a basic substance.
In a method for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate by reacting oxo-3-thiazolidine with S, O-dialkyl phosphorochloride thiolate, an alkali metal is used as a basic substance. Using a hydroxide or an alkaline earth metal hydroxide, and the reaction is carried out in the presence of a phosphonium salt or an ammonium salt as a phase transfer catalyst, S, O-
A method for producing dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2058678A JP2771882B2 (en) | 1990-03-09 | 1990-03-09 | Process for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2058678A JP2771882B2 (en) | 1990-03-09 | 1990-03-09 | Process for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03261792A JPH03261792A (en) | 1991-11-21 |
| JP2771882B2 true JP2771882B2 (en) | 1998-07-02 |
Family
ID=13091230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2058678A Expired - Lifetime JP2771882B2 (en) | 1990-03-09 | 1990-03-09 | Process for producing S, O-dialkyl (2-oxo-3-thiazolidinyl) phosphonothiolate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2771882B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5818073B2 (en) * | 2011-07-15 | 2015-11-18 | アグロカネショウ株式会社 | Process for producing O-ethyl Sn-propyl (E)-[2- (cyanoimino) -3-ethylimidazolidin-1-yl] phosphonothioate |
-
1990
- 1990-03-09 JP JP2058678A patent/JP2771882B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03261792A (en) | 1991-11-21 |
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