Patent GB-790197-A (GB)
Title: Benzyl phenyl sulphides and acaricidal compositions thereof
Inventor: STEVENSON HERBERT AUBREY
Filed: 1954-02-18
Abstract: The invention comprises benzyl phenyl sulphides of the general formula <FORM:0790197/IV (b)/1> in which the phenyl radical X may be unsubstituted or may carry as substituents one or more atoms of chlorine, bromine, fluorine or iodine and in which the phenyl radical Y may be unsubstituted or may carry as substituents one or more atoms of chlorine, bromine, fluorine or iodine provided that the phenyl radical X may not be unsubstituted or be substituted with a single chlorine atom or one or more atoms of bromine or of fluorine when the phenyl radical Y is unsubstituted, and provided that the phenyl radical X may not be unsubstituted or may not carry one or more atoms of chlorine or of fluorine when the phenyl radical Y carries one or more atoms of chlorine or of fluorine.  Compounds specified are p-bromobenzyl p-bromophenyl sulphide, p-bromobenzyl phenyl sulphide, benzyl 2:5-dichlorophenyl sulphide, p-bromobenzyl p-fluorophenyl sulphide, p-bromobenzyl p-chlorophenyl sulphide, p-chlorobenzyl p-bromophenyl sulphide, p-fluorobenzyl p-bromophenyl sulphide, p-fluorobenzyl p-bromophenyl sulphide, p-chlorobenzyl p-iodophenyl sulphide, p-iodobenzyl p-chlorophenyl sulphide, p-iodobenzyl p-iodophenyl sulphide, benzyl p-iodophenyl sulphide, p-iodobenzyl p-fluorophenyl sulphide, p-iodobenzyl phenyl sulphide, p-fluorobenzyl p-iodophenyl sulphide, p-iodobenzyl p-bromophenyl sulphide, and p-bromobenzyl p-iodophenyl sulphide.  The compounds are prepared by reacting a substituted benzyl halide of the general formula <FORM:0790197/IV (b)/2> where Hal is a halogen atom such as chlorine, with a thiol of the general formula <FORM:0790197/IV (b)/3> in the presence of an alkaline condensing agent such as sodium hydroxide or sodium ethoxide in a solvent such as methanol or ethanol.  The compounds are used in acaricidal compositions (see Group VI). Examples are given.  The Provisional Specification is not restricted to halogen-substituted benzyl phenyl sulphides and describes compounds of the above structural formula in which phenyls X and Y may carry one or more chlorine, bromine, iodine or fluorine atoms, lower alkyl, lower alkoxy, nitro or amino groups. The compounds described, which are not already mentioned above are p-chlorobenzyl p-methoxyphenyl sulphide, p-methoxy-benzyl p-chlorophenyl sulphide, p-chlorobenzyl p-allyloxyphenyl sulphide, p-methoxybenzyl phenyl sulphide, p-methoxybenzyl p-methoxyphenyl sulphide, p-chlorobenzyl p-tolyl sulphide, p-methyl benzyl p-chlorophenyl sulphide, 4-chlorobenzyl 2-methyl-5-chlorophenyl sulphide, p-methylbenzyl p-tolyl sulphide, p-methylbenzyl phenyl sulphide, p-fluorobenzyl p-tolyl sulphide, p-methylbenzyl p-fluorophenyl sulphide, p-fluorobenzyl p-methoxyphenyl sulphide and p-methoxybenzyl p-fluorophenyl sulphide.  Specifications 713,984, 738,170, 745,360, [Group VI], 748,604 and 758,926 are referred to in the Provisional Specification.ALSO:Acarical compositions are described as containing, together with a diluent or carrier, a benzyl phenyl sulphide of the formula: <FORM:0790197/VI/1> in which the phenyl radical X may be unsubstituted or may carry as substituents one or more atoms of chlorine, bromine, fluorine or iodine and in which the phenyl Y may be unsubstituted or may carry as substituents one or more atoms of chlorine, bromine, fluorine or iodine provided that the phenyl X may not be unsubstituted or substituted by a single chlorine atom or one or more atoms of bromine or of fluorine when the phenyl Y is unsubstituted, and provided that the phenyl X may not be unsubstituted or may not carry one or more atoms of chlorine or of fluorine when phenyl Y carries one or more atoms of chlorine or of fluorine.  Diluents or carriers used in compositions for the preparation of dispersions of solid in water comprise a dispersing agent and/or a suspending agent with an optional water-miscible organic solvent such as acetone, and may include an emulsifying agent and a non-volatile oil such as liquid paraffin for the preparation of solid dispersions in aqueous oil emulsions. Compositions for the preparation of aqueous emulsions comprise, as diluent or carrier, an emulsifying agent and an organic solvent such as xylene or an aromatic solvent boiling from 80-300 DEG  C. and optionally, a non-volatile vegetable or mineral oil such as liquid paraffin and a wetting agent.  Dispersions containing a pulverulent solid diluent are mentioned.  In smoke compositions the carrier comprises an ignitable slow-burning composition such that a smoke containing the active ingredient is generated on ignition.  Compositions for the preparation of mists and aerosols comprise the active ingredient and a mixture of a non-volatile oil such as a vegetable oil and a miscible supplementary solvent such as cyclohexanone or acetone and may contain a liquid propellant such as a mixture of chlorofluoro derivatives of methane and ethane.  In examples: (4) a water-dispersible powder containing p-bromobenzyl p-bromophenyl sulphide, kaolin and a condensate of formaldehyde and an alkyl aryl sulphonate, and compositions for the preparation of aqueous emulsions containing (5) p-chlorobenzyl p-bromophenyl sulphide, or (6) p-bromobenzyl phenyl sulphide, together with benzene and an emulsifying agent comprising an oleic acid ester of a glycol are described.  Many benzyl phenyl sulphides of the above general formula which may be used in similar dispersions and compositions are specified.  The Provisional Specification mentions compositions containing as active ingredient a compound of the above structural formula in which X and Y may be substituted by one or more chlorine, bromine, fluorine or iodine atoms, lower alkyl, lower alkoxy, nitro or amino groups.  Benzyl phenyl sulphides in which X and Y are substituted by methoxy, methyl and allyloxy groups and/or chlorine and fluorine atoms are described.  In examples: (2) a water-dispersible powder containing p-methoxy-benzyl p-fluorophenyl sulphide, kaolin and a dispersing agent; and (3) a composition for the preparation of aqueous emulsions containing p-methoxybenzyl p-fluorophenyl sulphide, benzene and an emulsifying agent are described.  Specifications 713,984, 738,170, 745,360, 748,604 and 758,926 are referred to in the Provisional Specification.