チオりん酸S-[2-(エチルスルフィニル)エチル]O,O-ジメチル

チオりん酸S-[2-(エチルスルフィニル)エチル]O,O-ジメチル 用途と合成の方法

• 用途

  浸透性、接触性殺虫、殺ダニ剤

• 農薬用途

  殺虫剤

• 説明

  Oxydemeton-methyl, i.e., demeton-S-methyl sulfoxide, is a colorless oil, bp 106 ?C/0.01 mm Hg, vp 3.8 mPa (20 ?C). It is miscible with water and soluble in most organic solvents, except petroleum ether. Log Kow = ?0.74(21 ?C). Oxydemeton-methyl is relatively stable in acidic media but hydrolyzed in alkalinemedia;DT₅₀ values (22 ?C) at pH 4, 7, and 9 are 107, 46, and 2 d, respectively.

• 化学的特性

  Oxydemeton methyl is a colorless to amber-colored liquid. Oxydemeton methyl is relatively slowly hydrolyzed in acidic media, but rapidly hydrolyzed in alkaline media.
  Oxydemeton methyl is miscible with water; readily soluble (10–100 g/ 100 mL) in dichloromethane, 2-propanol, and toluene; and practically insoluble (＜1 g/100 mL) in n-hexane.

• 使用

  Oxydemeton-methyl is used to control sucking insects on fruit, vines, vegetables, cereals and ornamentals.

• 一般的な説明

  Clear amber liquid.

• 空気と水の反応

  Water soluble. DEMETON-S-METHYL SULFOXIDE may be rapidly hydrolyzed by alkali .

• 反応プロフィール

  Organophosphates such as DEMETON-S-METHYL SULFOXIDE are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

• 火災危険

  DEMETON-S-METHYL SULFOXIDE is flammable.

• 安全性プロファイル

  Poison by ingestion, skin contact, intravenous, and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits very toxic fumes of POx and SOx. See also other demeton entries.

• 環境運命予測

  Soil. The sulfoxide group is oxidized to the sulfone and oxidative and hydrolytic cleavage of the side chain gives dimethylphosphoric and phosphoric acids (Hartley and Kidd, 1987). Oxamyl was degraded by the microorganism Pseudomonas putida in a laboratory study using cultured bacteria (Zeigler, 1980).
  Plant. In asparagus, oxydemeton-methyl was converted to the corresponding sulfone (Szeto and Brown, 1982).
  Chemical/Physical. Oxydemeton-methyl can be converted to the corresponding sulfone by hydrogen peroxide (Cremlyn, 1991). Emits toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987).

• 代謝経路

  Oxydemeton-methyl is the primary thiooxidation metabolite of demeton- S-methyl. It is further oxidised rapidly to demeton-Smethylsulfon in all media. The major route of further metabolism of both sulfoxide and sulfone is via hydrolysis to the sulfoxide and sulfone thiols. Stage I1 metabolism of these thiol hydrolysis products proceeds via oxidation and conjugation and is different in soil, plants and animals. In plants the thiols are conjugated, whereas in animals they are mainly methylated and oxidised to sulfoxides, sulfones and sulfonic acids. Demethylation is an important route in mammals; however, the compound is sufficiently polar for much to be excreted in the urine unchanged. Demethylation has also been reported to occur in plants.

• 代謝

  Almost 99% of orally administered oxydemeton-methyl to animals is excreted within 48 h in the urine. It is oxidized to the sulfone, followed by hydrolytic cleavage of the P?S bond. The thiol metabolites are conjugated or methylated. O-Demethylation is also an important degradation route both inmammals and plants. Oxydemeton-methyl is rapidly degraded in soils.