Patent GB-687177-A (GB)
Title: Improvements in or relating to insecticidal and fungicidal compositions and active thiocyanates therefor
Inventor: BARBER HARRY JAMES
IPC: C07C331/10
Filed: 1949-10-08
Abstract: Organic thiocyanates of the general formula RXCH2SCN (in which R is an aromatic nucleus and X is an oxygen or sulphur atom) are prepared by reacting a compound of the formula RXCH2Y (in which Y is a chlorine or bromine atom) with an inorganic thiocyanate.  The reaction is effected at room temperature or slightly above, preferably in the presence of a liquid diluent. The invention comprises also the thiocyanates of the above general formula, particularly 2,4-dichlorophenoxymethyl thiocyanate, 4 - chloro - 3 - methylphenoxymethyl-thiocyanate, and 4-chloro-phenoxymethyl thiocyanate.  The following are also specified: 3,5 - dimethyl - 4 - chlorophenoxymethyl thiocyanate, 4-bromophenoxy-methyl thiocyanate, 2-methyl-4-chlorophenoxymethyl thiocyanate, 3,4 - dichlorophenoxymethyl thiocyanate, 2,5-dichlorophenoxymethyl thiocyanate, 4-nitro-phenoxymethyl thiocyanate, 2-nitro-4-chlorophenoxymethyl thiocyanate, a  - naphthoxymethyl thiocyanate, 4-methoxyphenoxymethyl thiocyanate and 4-chlorophenylthiomethyl thiocyanate.  In examples: (1) potassium thiocyanate is added to a solution of 2,4-dichlorophenoxymethyl chloride in acetone to yield 2,4-dichlorophenoxymethyl thiocyanate; (2) and (3) 4-chlorophenoxymethyl chloride and 4-chloro-3-methylphenoxymethyl chloride are reacted similarly with potassium thiocyanate to yield 4 - chlorophenoxymethyl thiocyanate and 4 - chloro - 3 - methylphenoxymethyl thiocyanate, respectively. Specification 647,215 is referred to.ALSO:Seeds are treated with a fungicidal and insecticidal composition comprising a thiocyanate of the general formula RXCH2SCN (in which R is an aromatic nucleus and X is oxygen or sulphur).  Examples of such thiocyanates (see Group IV(b)) are 2, 4-dichlorophenoxymethyl-, 4-chlorophenoxymethyl-, 4-chloro-3-methylphenoxymethyl-, 3, 5-dimethyl-4-chlorophenoxymethyl-, 4-bromophenoxymethyl-, 2-methyl-4-chlorophenoxymethyl-, 3, 4- dichlorophenoxymethyl-, 2, 5-dichlorophenoxymethyl-, 4-nitrophenoxymethyl-, 2-nitro-4-chlorophenoxymethyl-, a -naphthoxymethyl-, 4-methoxyphenoxymethyl-, and 4 chlorophenylthiomethyl-thiocyanates. An Example is given of the treatment of seed oats infected with Helminthosporium avenae with a dust made by adding a solution of 4-chlorophenoxymethyl thiocyanate in acetone to kaolin and drying.ALSO:A composition having insecticidal, acaricidal, fungicidal and herbicidal activity comprises a thiocyanate of the general formula RXCH2SCN (in which R is an aromatic nucleus and X is oxygen or sulphur) in association with a solid or liquid diluent. Thiocyanates specified (see Group IV (b)) are 2,4-dichlorophenoxymethyl-, 4-chlorophenoxymethyl-, 4-chloro-3-methylphenoxymethyl-, 3,5 - dimethyl - 4 - chlorophenoxy - methyl-, 4-bromophenoxymethyl-, 2-methyl-4-chlorophenoxymethyl -, 3,4 - dichlorophenoxy - methyl-, 2,5-dichlorophenoxymethyl-, 4-nitro-phenoxymethyl-, 2-nitro-4-chlorophenoxymethyl-, a -naphthoxymethyl-, 4-methoxyphenoxymethyl-, and 4-chlorophenylthiomethyl-thiocyanates.  The diluent may be a liquid, conveniently water, preferably together with a solvent or solid carrier in the presence of a wetting, dispersing or emulsifying agent.  The agents may be used as spray formations of the wettable powder type in which kaolin or the like is impregnated with the active agent either dry or in solution.  For treating soil infestation, the active agent may be mixed with kaolin, gypsum or chalk.  The agents may also be employed in the form of aerosols or smoke generators, or they may be used as fumigants e.g., by impregnating strips of porous material with the agent and locating the impregnated material in the closed space to be treated.  An example is given of a self-emulsifying concentrate containing 4-chlorophenoxymethyl thiocyanate, a non-ionic emulsifying agent, a mineral oil and xylene.