Patent GB-967016-A (GB)
Title: Mixed sulphite diesters
IPC: C07C301/00
Filed: 1962-06-15
Abstract: The invention comprises mixed sulphite diesters of a phenol or naphthol and a glycol ether, the glycol ether being an ether of a glycol having 1 to 10 alkyleneoxy groups each having 2 to 10 carbon atoms and an alcohol, phenol or naphthol. Preferably the diesters are of the formula <FORM:0967016/C1/1> wherein R is an alkyl, cycloalkyl, alkenyl, cyanoalkyl or haloalkyl or a phenyl or naphthyl radical unsubstituted or substituted by alkyl, cycloalkyl, halo alkyl, alkoxy orhalo; R1 is a phenyl or naphthyl radical unsubstituted or substituted by alkyl, cycloalkyl, haloalkyl, alkoxy or halo; n is 2 to 10 and m is 1 to 10. Where m is greater than 1, the repeating alkoxy groups may be the same or different. Examples of R include methyl, propyl, tert. butyl, isodecyl, cyclohexyl, allyl, methallyl, 2-cyanoethyl, 2-chloroethyl, 2,2,2-trichloroethyl, phenyl, 1-naphthyl, p-tolyl, isopropylphenyl, cyclohexyl phenyl, chloromethyl phenyl, methoxy phenyl, bromophenyl and pentachlorophenyl. Examples of R1 include phenyl, 1-naphthyl, p-tolyl, tert. butylphenyl, cyclohexylphenyl, chloromethylphenyl, methoxyphenyl, bromophenyl and pentachlorophenyl groups. Examples of the -(OCnH2n)- group are ethyleneoxy, trimethyleneoxy, tetramethyleneoxy, propyleneoxy, and 1, 2-dimethylethyleneoxy.  The esters are prepared from the chlorosulphinates of the glycol ethers by treatment in a solvent, for example, benzene, xylene or solvent naphtha with the phenol in the presence of an HCl acceptor, for example: pyridine, aniline or trimethylamine, at between -10 DEG  and 50 DEG C. These compounds may be used as insecticides (see Division A5).  The above chlorosulphinates may be prepared by reaction at between -5 DEG C. and 30 DEG C. of thionyl chloride with the required glycol ethers which may be prepared by the reaction of one mole of the alcohol or phenol with 1 to 10 moles of alkylene oxide preferably in the presence of alkali.ALSO:Insecticide compositions contain as the active ingredients, sulphite di-esters of a phenol or naphthol and a glycol ether, the glycol ether being an ether of a glycol having 1 to 10 alkyleneoxy groups each having 2 to 10 carbon atoms and an alcohol, phenol or naphthol, preferably of the formula <FORM:0967016/A5-A6/1> wherein R is an aliphatic radical, e.g. alkyl, cycloalkyl, alkenyl, cyanoalkyl or haloalkyl or a phenyl or naphthyl radical unsubstituted or substituted by alkyl, cycloalkyl, haloalkyl, alkoxy or halo; R1 is a phenyl or naphthyl radical, unsubstituted or substituted by alkyl, cycloalkyl, haloalkyl, alkoxy or halo; n is 2 to 10 and m is 1 to 10 (see Division C2). The chemicals may be applied as dusts mixed with powdered solid carriers, for example, mica, talc, pyrophyllite and clays; as liquids or sprays when dissolved in a solvent, for example, octane, benzene or kerosene or as aerosol sprays when dissolved directly in an aerosol carrier. They are preferably used in aqueous emulsions containing an anionic, non-ionic or cationic surface active dispersing agent or as aqueous suspensions containing solid powder carriers and dispersing agents. Examples describe the use of o - tolyl - p - tert. butylphenoxy isopropyl sulphite, o-tolyl-isodecoxyethyl sulphite and nonylphenyl - p - tert. butylphenoxy isopropyl sulphite in the control of mosquito larv , and o-tolyl - p - tert. butylphenoxy isopropylsulphite, o - tolyl - isodecoxyethyl sulphite, nonylphenyl-p - tert. butylphenoxy isopropyl sulphite, p-tert. butylphenyl - p - tert. amylphenoxyethyl sulphite and o-tolyl-p-tert. amylphenoxyethyl sulphite in the control of mites.