Patent GB-957208-A (GB)
Title: S-(10-phenoxyarsinyl) esters and biologically active preparations containing them
IPC: C07F9/70
Filed: 1961-03-21
Abstract: The invention comprises S-(10-phenoxarsinyl) esters of C2-C18 aliphatic dicarbothioic acids, C1-C18 aliphatic carbothioic acids, C1-C18 alkyl xanthic acids, C1-C5 alkenyl xanthic acids, cyclohexyl xanthic acid, cyclohexyl, phenyl and phenoxy aliphatic carbothioic acids, or substituted aliphatic carbothioic acids wherein the substituents are chlorophenoxy, chlorophenyl, bromophenoxy, bromophenyl, alkoxyphenoxy, alkylphenoxy, alkoxyphenyl or alkylphenyl in which the alkyl, alkenyl, alkoxy groups and the substituted carbothioic acids contain 1 to 5 carbon atoms. (Carbothioic = -COSH or -CSOH).  Specified compounds are S-(10-phenoxarsinyl)-allyl xanthate, -thiooctanoate, -octyl xanthate, -cyclohexyl xanthate and -thiovalerate. They may be prepared by reacting 10, 101-oxybisphenoxarsine with the appropriate acid as listed above, conveniently in the presence of an inert organic liquid such as benzene, toluene or xylene as reaction medium.  Alternatively 10-chlorophenoxarsine or 10-bromophenoxarsine may be reacted with the alkali metal salt of the selected acid.  The product may be obtained by evaporation of the solvent (or filtering off the alkali metal halide), washing with a non-polar solvent e.g. cyclohexane or ligroin and recrystallization. The compounds may be used as active ingredients in pesticides, disinfectants and herbicides (see Divisions A5 and C4).  The sulphur containing organic acids which may be esterified to give the compounds of the invention may be prepared as follows:  Xanthic acids.  An alkali metal hydroxide, carbon disulphide and cyclohexanol, a suitable alkanol or a C1-C5 alkenyl alcohol are reacted together in an inert organic liquid.  The alkali metal xanthate may be separated by conventional methods.;  Aliphatic dicarbothioic acids, aliphatic carbothioic acids and substituted aliphatic carbothioic acids may be prepared by reacting the acid halides of the corresponding acids with ethanolic potassium hydrosulphide (KSH) at a temperature from about -10 DEG  to 25 DEG C. The separated potassium halide is filtered off, the reaction medium evaporated under reduced pressure, the residue dispersed in water and acidified with hydrochloric acid.  The acid may then be extracted with ether.  Numerous examples of these sulphur-containing acids are disclosed.ALSO:Paints may contain as a biologically active ingredient to protect against attack by plant or animal life a S-(10-phenoxarsinyl) ester of a C2-C18 aliphatic dicarbothioic acid, a C1-C18 aliphatic carbothioic acid, a C1-C18 xanthic acid, a C1-C5 alkenyl xanthic acid, cyclohexylxanthi acid, cyclohexyl, phenyl or phenoxy aliphatic carbothioic acids or a substituted aliphatic carbothioic acid wherein the substituent is chlorophenoxy, chlorophenyl, bromophenoxy, bromophenyl, alkoxyphenoxy, alkyl phenoxy, alkyl phenoxy or alkylphenyl in which the alkyl, alkenyl, alkoxy groups and the substituted carbothioic acids contain 1-5 carbon atoms.  (Carbothioic = -COSH or -CSOH).ALSO:Biologically active preparations, particularly pesticides, parasiticides, disinfectants and/or herbicides comprise a S-(10-phenoxyarsinyl) ester of an acid defined below and a carrier or diluent.  The acid may be a C2-C18 aliphatic dicarbothioic acid, a C1-C18 aliphatic carbothioic acid, a C1-C18 alkyl xanthic acid, a C1-C5 alkenyl xanthic acid, cyclohexyl xanthic acid, cyclohexyl, phenyl or phenoxy aliphatic carbothioic acids or a substituted aliphatic carbothioic acid wherein the substituent is chlorophenoxy chlorophenyl, bromophenoxy, bromophenyl, alkoxyphenoxy, alkylphenoxy, alkoxyphenyl or alkylphenyl in which the alkyl, alkenyl, alkoxy groups and the substituted carbothioic acids contain 1-5 carbon atoms.  (Carbothioic = -COSH or -CSOH.)  Specified compounds are S-(10-phenoxyarsinyl)-allyl xanthate, -thiooctanoate, -octyl xanthate, -cyclohexyl xanthate and -thiovalerate.  The active compound may be dispersed on an inert finely divided solid, dispersed in water with or without a surface-active agent or used as an oil-in-water or water-in-oil emulsion.  They may also be incorporated in paint films, plastic articles or wood.