Patent GB-790198-A (GB)
Title: Benzyl phenyl sulphoxides and acaricidal compositions thereof
Inventor: STEVENSON HERBERT AUBREY
Filed: 1954-02-18
Abstract: The invention comprises benzyl phenyl sulphoxides of the formula <FORM:0790198/IV (b)/1> in which phenyl radical X may be unsubstituted or be substituted by one or more radicals selected from the group consisting of chlorine, bromine, fluorine or iodine, alkyl or alkoxy groups (either of which are of 1 to 8 carbon atoms) and the phenyl Y may be unsubstituted or be substituted by one or more radicals selected from the group consisting of chlorine, bromine, fluorine or iodine atoms, alkyl groups of 1 to 8 carbon atoms or nitro groups, provided that Y may not be unsubstituted or be substituted by one or more chlorine atoms when X is unsubstituted or is substituted by one or more chlorine atoms.  Compounds specified are p-fluorobenzyl p-tolyl sulphoxide, m-chlorobenzyl p-fluorophenyl sulphoxide, p-chlorobenzyl p-fluorophenyl sulphoxide, p-iodobenzyl p-iodophenyl sulphoxide, p-chlorobenzyl p-iodophenyl sulphoxide, p-iodobenzyl p-chlorophenyl sulphoxide, benzyl p-iodophenyl sulphoxide, p-fluorobenzyl p-iodophenyl sulphoxide, p-iodobenzyl phenyl sulphoxide, p-iodobenzyl p-bromophenyl sulphoxide, p-iodobenzyl p-fluorophenyl sulphoxide, p - bromobenzyl phenyl sulphoxide, p - bromobenzyl p - chlorophenyl sulphoxide, p - iodobenzyl p - tolyl sulphoxide, p - bromobenzyl p - iodophenyl sulphoxide, p-iodobenzyl p-methoxyphenyl sulphoxide, p-methylbenzyl p-iodophenyl sulphoxide, p-nitrobenzyl p-chlorophenyl sulphoxide, p-bromobenzyl p-tolyl sulphoxide, p-bromobenzyl p-bromophenyl sulphoxide, p-bromobenzyl p-fluorophenyl sulphoxide, p - fluorobenzyl p-fluorophenyl sulphoxide, benzyl p-fluorophenyl sulphoxide, p - chlorobenzyl p - bromophenyl sulphoxide, and benzyl p-bromophenyl sulphoxide.  The compounds are prepared by oxidizing the corresponding benzyl phenyl sulphides with hydrogen peroxide in glacial acetic acid solution.  In an example, p-fluorobenzyl p-tolyl sulphide in glacial acetic acid is heated under reflux with aqueous hydrogen peroxide, diluted with water and p-fluorobenzyl p-tolyl sulphoxide isolated by filtration and purified by recrystallization from alcohol.  The compounds are used in acaricidal compositions (see Group VI].  In the Provisional Specification, compounds of the above general formula in which Y is unsubstituted or is substituted by one or more chlorine atoms when X is unsubstituted or substituted by one or more chlorine atoms are not excluded.  Specifications 713,984, 738,170, 748,604, 758,926, 790,197 are referred to and Specification 749,446 is referred to in the Provisional Specification.ALSO:Acaricidal compositions are described containing as active ingredient a compound of the formula: <FORM:0790198/VI/1> where phenyl X may be unsubstituted or be substituted by one or more radicals selected from chlorine, bromine, fluorine or iodine atoms, or alkyl or alkoxy groups containing from 1 to 8 carbon atoms, and phenyl Y may be unsubstituted or be substituted by one or more radicals selected from chlorine, bromine, fluorine or iodine, alkyl groups of 1 to 8 carbon atoms or nitro groups, provided that Y may not be unsubstituted or be substituted by one or more chlorine atoms when X is unsubstituted or is substituted by one or more chlorine atoms.  The compositions also contain a diluent or carrier.  Examples of many compounds having the above general formula are given.  The compositions may be used in the form of dusts, dispersions and emulsions.  Dusts comprise up to 50 gms. of active ingredient per 100 c.cs. of a pulverulent solid diluent.  Compositions for the formation of dispersions contain active ingredient, a dispersing agent and/or suspending agent and optionally a water-miscible organic solvent such as acetone, and give a dispersion having a solid dispersed phase on addition to water.  Other dispersion compositions contain active ingredient, a dispersing and/or suspending agent, an emulsifying agent, a non-volatile oil such as liquid paraffin and water, giving a solid suspension in an aqueous oil emulsion, the active ingredient being insoluble in the oil.  Compositions for the formation of emulsions contain active ingredient, an emulsifying agent and an organic solvent such as xylene or an aromatic solvent boiling between 80 DEG  and 300 DEG  C. and may optionally contain a non-volatile vegetable or mineral oil such as liquid paraffin and a wetting agent, so that an emulsion is formed on addition to water.  The aqueous dispersions and emulsions may be diluted with water to give a final concentration of active ingredient of 0.001-10 gms. per 100 ccs.  In examples: (2) a composition for preparing an aqueous suspension contains p-chlorobenzyl p-fluorophenyl sulphoxide, an emulsifying agent and kaolin; (3) an aqueous dispersion containing p-chlorobenzyl p-fluorophenyl sulphoxide, a dispersing agent and water is added to (4) an emulsion prepared from liquid paraffin, an emulsifying agent, a thickening agent and water to form a white oil suspension. Specifications 713,984, 738,170, 748,604, 758,926, 790,197 are referred to and Specification 749,446 is referred to in the Provisional Specification.