GB790199A - Benzyl phenyl sulphides and acaricidal compositions thereof - Google Patents

Benzyl phenyl sulphides and acaricidal compositions thereof

Info

Publication number
GB790199A
GB790199A GB360655A GB360655A GB790199A GB 790199 A GB790199 A GB 790199A GB 360655 A GB360655 A GB 360655A GB 360655 A GB360655 A GB 360655A GB 790199 A GB790199 A GB 790199A
Authority
GB
United Kingdom
Prior art keywords
substituted
nitro
chloro
methyl
unsubstituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB360655A
Inventor
Herbert Aubrey Stevenson
Nigel George Clark
John Ray Marshall
Douglas Greenwood
John Ernest Cranham
Dennis John Higgons
Robert Frederick Brookes
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure Drug Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB360655A priority Critical patent/GB790199A/en
Publication of GB790199A publication Critical patent/GB790199A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00Thiols, sulfides, hydropolysulfides or polysulfides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises benzyl phenyl sulphides of the formula: <FORM:0790199/IV (b)/1> in which (a) one of the phenyl radicals X and Y is substituted by one or more lower alkyl, lower alkoxy, alkenyloxy, or nitro groups and may be additionally substituted by one or more halogen atoms when the other radical is substituted by one or more halogen atoms or lower alkyl, lower alkoxy, or nitro groups; (b) Y is substituted by one or more lower alkyl, lower alkoxy, or nitro groups when X is unsubstituted; (c) X is substituted by one or more nitro groups and by one or more halogen atoms when Y is unsubstituted; (d) X is substituted by one or more halogen atoms or nitro groups when Y is unsubstituted; provided that (1) if X is unsubstituted or is substituted by one or more chlorine atoms only then Y is not substituted only by one or more nitro groups, (2) if X is substituted by one lower alkyl group only, then Y is not substituted only by more than one lower alkyl group. The groups "lower alkyl" and "lower alkoxy" contain 1 to 8 carbon atoms inclusive. The compounds are prepared by reacting a halide of the formula: <FORM:0790199/IV (b)/2> with a thiol of the formula: <FORM:0790199/IV (b)/3> in the presence of an alkaline condensing agent such as potassium hydroxide in aqueous alcohol or sodium ethoxide, X and Y having the meanings given above. Compounds of the above general formula are mentioned wherein X is unsubstituted or is p-methyl-, p-ethyl-, p-methoxy-, p-allyloxy-, p-chloro-, p-iodo, p-fluoro, p-nitro -, 4 - chloro - 2 - methyl -, 4 - chloro - 3-methyl -, 5 - chloro - 2 - methyl -, 2:4 - dichloro - 3 - methyl -, 2:4 - dichloro - 5 - methyl-, 4 - methyl - 3 - nitro -, 2 - methoxy - 4 - nitro-, 2 - chloro - 5 - nitro -, and 4 - chloro - 2 - nitrophenyl, and wherein Y is unsubstituted or is p-methyl -, p - methoxy -, o -, m - or p - chloro-, p - bromo -, p - fluoro -, p - iodo -, p - nitro-2:6 - dichloro -, and 4 - methoxy - 3 - nitrobenzyl. Examples are given. The compounds are used in acaricidal compositions (see Group VI). The Provisional Specification relates to benzyl phenyl sulphides of the above formula where Y is substituted by one or more halogen, lower alkyl, lower alkoxy, nitro or amino groups and Y is unsubstituted or is substituted by one or more of the substituents given for Y. Specifications 713,984, 738,170, 745,360, [Group VI], 748,604 and 758,926 are referred to in the Provisional Specification.ALSO:An acaricidal composition comprises a diluent or carrier and as active ingredient a benzyl phenyl sulphide of the formula <FORM:0790199/VI/1> in which (a) one of the phenyl radicals X and Y is substituted by one or more lower alkyl, lower alkoxy, alkenyloxy, or nitro groups and may be additionally substituted by one or more halogen atoms when the other radical is substituted by one or more halogen atoms or lower alkyl, lower alkoxy, or nitro groups; (b) Y is substituted by one or more lower alkyl, lower alkoxy, or nitro groups when X is unsubstituted; (c) X is substituted by one or more nitro groups and by one or more halogen atoms when Y is unsubstituted; (d) X is substituted by one or more lower alkyl or alkoxy groups and one or more halogen atoms or nitro groups when Y is unsubstituted; provided that (1) if X is unsubstituted or is substituted by one or more chlorine atoms only, then Y is not substituted only by one or more nitro groups, and (2) if X is substituted by one lower alkyl group only, then Y is not substituted only by more than one lower alkyl group. The groups "lower alkyl" and "lower alkoxy" contain 1 to 8 carbon atoms inclusive. Compounds of the above formula are mentioned in which X is unsubstituted or is p-methyl-, p-ethyl-, p-methoxy-, p-allyloxy-, p-chloro, iodo, or fluoro-, p-nitro-, 4-chloro-2-methyl (or 3-methyl)-, 5-chloro-2-methyl-, 2 : 4-dichloro-3(or 5)-methyl-, 4-methyl-3-nitro-, 2-methoxy - 4 - nitro -, 2 - chloro - 5 - nitro -, and 4-chloro-2-nitro-phenyl, and wherein Y is unsubstituted or is p-methyl (or methoxy, bromo, fluoro, iodo, or nitro)-, o, m- or p-chloro-, 2 : 6-dichloro-, and 4-methoxy-3-nitro-benzyl. Examples of these are p-chlorobenzyl p-methoxyphenyl sulphide, p-fluorophenyl p-methoxybenzyl sulphide, 2 : 6-dichlorobenzyl 2 : 4-dichloro-3-methylphenyl sulphide, 4-methoxy-3-nitrobenzyl p-chlorophenyl sulphide, and p-nitrobenzyl 4 - chloro - 2 - nitrophenyl sulphide. The composition may be in the form of a dust, dispersion, emulsion, smoke, mist, or aerosol. It may contain a water-miscible organic solvent such as acetone. It may be in the form of a solid dispersed phase in an aqueous oil emulsion and the oil may be paraffin oil. The composition may comprise the active ingredient with an emulsifying agent and an organic solvent such as xylene and, if desired, a vegetable or mineral oil. The carrier may be a pulverulent solid, e.g. kaolin. For smoke compositions the carrier comprises an ignitable slow-burning substance so that a smoke containing the active ingredient is generated on ignition. For mists and aerosols the active ingredient may be dissolved in a mixture of a vegetable oil and cyclohexanone or acetone and the solution may be dispersed by mechanical means or by incorporating a volatile propellant such as a mixture of chloro-fluoro derivatives of methane and ethane. Specifications 713,984, 738,170, 745,360, 748,604 and 758,926 are referred to in the Provisional Specification.
GB360655A 1954-02-18 1954-02-18 Benzyl phenyl sulphides and acaricidal compositions thereof Expired GB790199A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB360655A GB790199A (en) 1954-02-18 1954-02-18 Benzyl phenyl sulphides and acaricidal compositions thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB360655A GB790199A (en) 1954-02-18 1954-02-18 Benzyl phenyl sulphides and acaricidal compositions thereof

Publications (1)

Publication Number Publication Date
GB790199A true GB790199A (en) 1958-02-05

Family

ID=9761505

Family Applications (1)

Application Number Title Priority Date Filing Date
GB360655A Expired GB790199A (en) 1954-02-18 1954-02-18 Benzyl phenyl sulphides and acaricidal compositions thereof

Country Status (1)

Country Link
GB (1) GB790199A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0301421A2 (en) * 1987-07-28 1989-02-01 Roche Diagnostics GmbH Sulfur compounds, process for their preparation and medicines
WO2015090122A1 (en) * 2013-12-20 2015-06-25 北京智博高科生物技术有限公司 Phenyl benzyl ether derivative and preparation method and use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0301421A2 (en) * 1987-07-28 1989-02-01 Roche Diagnostics GmbH Sulfur compounds, process for their preparation and medicines
EP0301421A3 (en) * 1987-07-28 1989-05-10 Boehringer Mannheim Gmbh Sulfur compounds, process for their preparation and medicines
WO2015090122A1 (en) * 2013-12-20 2015-06-25 北京智博高科生物技术有限公司 Phenyl benzyl ether derivative and preparation method and use thereof
JP2017503012A (en) * 2013-12-20 2017-01-26 ベイジン ズィボォ バイオメディカル テクノロジー カンパニー、リミテッド Phenylbenzyl ether derivatives and their preparation and applications

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