O-PHENYLTHIONOTHIOLPHOSPHORIC ACID ESTERS AND THEIR USE AS INSECTICIDES AND ACARICIDES

摘要

1460423 O-Substituted phenyl dithiophosphate esters BAYER AG 15 Nov 1974 [17 Nov 1973] 49513/74 Headings C2P and C2C The invention comprises dithiophosphate esters of the formula wherein R1 is H or halogen (e.g. Cl or Br) and R2 is alkylsulphonyl, haloalkylsulphonyl, or 1 - fluoro - 1 - carbalkoxy - methylmercapto having 1 to 4 C atoms in the alkyl group. They may be obtained by reacting a substituted phenol: in the presence of an acid binding agent or in the form of an alkali metal-, alkaline earth metal- or ammonium salt, with a halide: (C 2 H 5 O)(nC 3 H 7 S)P(S)Hal, where Hal is halogen, preferably Cl. The products have insecticidal and acaricidal properties and may be used as active ingredients in conventional pesticidal compositions. 4-Chloromethylsulphonyl phenol is obtained by adding sulphuryl chloride dropwise to a mixture of 4-methylmercapto phenol, ethylene chloride, acetic anhydride and a small amount of cone. H 2 SO 4 , stirring the mixture at 40‹ to 45‹ C., passing a stream of air through the solution and then adding 50% H 2 O 2 and sodium molybdate at 50‹ C. with further stirring at 60‹ to 65‹ C., the product being isolated after first destroying excess peroxide with sodium bisulphite solution, adding an aqueous solution of NaOH, filtering off the precipitated sodium phenolate and then dissolving the latter in water and acidifying with aqueous HCl. Treatment of the product (dissolved in acetic acid) with chlorine yields 2- chloro-4-chloromethylsulphonyl phenol. The following compounds: can be obtained in an analogous manner to the last-mentioned chlorination method. The compound: is obtained by adding first thiohydroquinone and then fluorochloroacetic acid ethyl ester to a solution of sodium in ethanol at 20‹ to 25‹ C., stirring the mixture for 3 days in the same temperature range and then pouring into water.