GB800713A - Sulphur-containing benzoxazole derivatives and compositions containing them - Google Patents

Sulphur-containing benzoxazole derivatives and compositions containing them

Info

Publication number
GB800713A
GB800713A GB1216455A GB1216455A GB800713A GB 800713 A GB800713 A GB 800713A GB 1216455 A GB1216455 A GB 1216455A GB 1216455 A GB1216455 A GB 1216455A GB 800713 A GB800713 A GB 800713A
Authority
GB
United Kingdom
Prior art keywords
benzoxazole
mixture
compounds
phenol
active
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
GB1216455A
Inventor
Herbert Aubrey Stevenson
Douglas Greenwood
John Ernest Cranham
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 GB1216455A priority Critical patent/GB800713A/en
Publication of GB800713A publication Critical patent/GB800713A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/58Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Abstract

The invention comprises compounds having the general formula <FORM:0800713/IV (b)/1> in which m and n have the values 0 or 1 such that m has the value 0 when n has the value 1 and the benzene nucleus X is substituted by one or more radicals selected from chlorine, bromine, fluorine and iodine atoms and nitro groups, and m has the value 1 when n has the value 0 and the benzene nucleus X is unsubstituted or substituted by one or more radicals as hereinbefore specified. The compounds of the class where m is 0 and n is 1 may be prepared by heating benzoxazole-2-thiol with a benzyl halide, wherein the benzene nucleus is substituted as described above, in the presence of an alkaline condensing agent. The compounds of the class where m is 1 and n is 0 may be prepared by ring closure of an o-(phenylthioacetylamino)-phenol of the formula HO.C6H5.NH.CO.CH2S.X, where the benzene nucleus X is unsubstituted or substituted, as described above, by known methods, for example, by heating with phosphorus pentoxide in an inert solvent. The novel compounds are useful as active ingredients in acaricidal compositions ((see Group VI). In examples: (1) 2 - (41 - bromobenzylthio)-benzoxazole is obtained by refluxing for 2 hours a mixture of p-bromobenzyl bromide, benzoxazole-2-thiol and anhydrous potassium carbonate in acetone; in a similar manner, 2-(41-chlorobenzylthio) - benzoxazole, 2 - (41 - nitrobenzylthio)-benzoxazole and 2-(41-fluorobenzylthio)-benzoxazole are obtained; (2) 2-(phenylthiomethyl) - benzoxazole is obtained by refluxing for 4 hours a mixture of o-(phenylthioacetylamino)-phenol and phosphorus pentoxide in dry benzene; (3) 2-(p-chlorophenylthiomethyl)-benzoxazole is obtained by refluxing for 6 hours a mixture of o-(p-chlorophenylthioacetylamino)-phenol and phosphorus pentoxide in toluene. o-(Phenylthioacetylamino)-phenol is obtained by adding aqueous methanolic sodium hydroxide to a boiling solution of o-(chloroacetylamino)-phenol and benzenethiol in methanol and refluxing the mixture for 20 minutes. o - (p - Chlorophenylthioacetylamino)-phenol is prepared in a similar manner from o-(chloroacetylamino)-phenol and p-chlorobenzenethiol. The Provisional Specification describes also the preparation of 2-benzylthiobenzoxazole by refluxing a mixture of benzyl chloride, benzoxazole-2-thiol and anhydrous potassium carbonate in dry acetone.ALSO:An acaricidal composition contains as its active ingredient a compound of the formula <FORM:0800713/VI/1> in which m is 0 when n is 1 and the benzene nucleus X is substituted by one or more radicals selected from chlorine, bromine, fluorine or iodine atoms and nitro groups, and m is 1 when n is 0 and the benzene nucleus X is unsubstituted or substituted as indicated above, together with a diluent or carrier. For preparation of the active compounds (see Group IV (b)). Dusts, dispersions, emulsions and aerosols containing the above compounds are valuable for the control of the eggs and active stages of the plant feeding Tetranychidae or Red Spider mites, e.g. Tetranychua telaurius L. and Metatetranychus ulmi Koch and the Tea Red Spider mite Metatetranydus bisculatus Wood-Mason. The active ingredient may be admixed with a dispersing and/or suspending agent such that a dispersion is formed when the mixture is added to water. Such a composition may also contain a water-miscible organic solvent such as acetone. Other suitable dispersions comprise the active compounds in admixture with a dispersing agent, an emulsifying agent, a non-volatile oil, such as liquid paraffin, and water. Suitable emulsions may comprise the active compound together with an emulsifying agent and an organic solvent, e.g. xylene or an aromatic solvent boiling in the range 80-300 DEG C. It may be advantageous to add a non-volatile vegetable oil or mineral oil such as liquid paraffin. The emulsion may also contain a wetting agent. The aqueous dispersions and emulsions may be diluted with water to a concentration of active ingredient in the range 0.001-10 per cent w./v. The compositions may also comprise dispersions of up to 50 per cent active compound in a pulverulent solid diluent. Compositions suitable for dispersion as aerosols may contain the active compound dissolved in a volatile solvent, e.g. acetone, or in a high-boiling aromatic solvent such as xylene or non-volatile oil such as a vegetable oil together with cyclohexanone or acetone. Such compositions are readily dispersed as aerosols by mechanical means or by incorporating a volatile propellant such as a mixture of chlorofluoro derivatives of methane and ethane. Other compounds which are active against the adult stages of mites may be incorporated into the compositions, e.g. Parathion and "Malathion" (Registered Trade Mark). In examples: (4) a dispersible powder is prepared by mixing 2-(41-bromobenzylthio)-benzoxazole with a condensate of formaldehyde and an alkyl aryl sulphonate, and kaolin; this composition may be added to water; (5) 2-(41-bromo - benzylthio) - benzoxazole is dissolved in a mixture of Insem 108 (an oleic acid ester of a glycol) and benzene to give a solution containing 5 per cent w./v. of active compound, the composition being suitable for dilution with water to obtain a stable emulsion; (6) a solution readily dispersed as an aerosol is obtained by dissolving 2-(41-bromobenzylthio)-benzoxazole in acetone to a concentration of 5 per cent w./v.; (7) an acaricidal dust comprises 5 parts by weight of 2-(41-bromobenzylthio) benzoxazole and 95 parts of kaolin. Similar compositions may be obtained using 2-(41-chlorobenzylthio)-benzoxazole, 2 - (41 - nitrobenzylthio) - benzoxazole, 2-(41-fluorobenzylthio)-benzoxazole, 2-(phenylthiomethyl) - benzoxazole, and 2 - (p - chlorophenylthiomethyl) - benzoxazole. The Provisional Specification describes also a dispersible powder comprising 2-benzylthiobenzoxazole, a condensate of formaldehyde and an alkyl aryl sulphonate, and kaolin which may be added to water to form a dispersion suitable for horticultural use.
GB1216455A 1955-04-27 1955-04-27 Sulphur-containing benzoxazole derivatives and compositions containing them Expired GB800713A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1216455A GB800713A (en) 1955-04-27 1955-04-27 Sulphur-containing benzoxazole derivatives and compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1216455A GB800713A (en) 1955-04-27 1955-04-27 Sulphur-containing benzoxazole derivatives and compositions containing them

Publications (1)

Publication Number Publication Date
GB800713A true GB800713A (en) 1958-09-03

Family

ID=9999529

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1216455A Expired GB800713A (en) 1955-04-27 1955-04-27 Sulphur-containing benzoxazole derivatives and compositions containing them

Country Status (1)

Country Link
GB (1) GB800713A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2181135A (en) * 1985-10-03 1987-04-15 American Home Prod Substituted benzene derivatives
EP1967514B1 (en) * 1999-10-04 2013-01-02 Nippon Soda Co., Ltd. Phenolic compounds and recording materials containing the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2181135A (en) * 1985-10-03 1987-04-15 American Home Prod Substituted benzene derivatives
GB2181135B (en) * 1985-10-03 1989-09-13 American Home Prod Substituted benzene derivatives
EP1967514B1 (en) * 1999-10-04 2013-01-02 Nippon Soda Co., Ltd. Phenolic compounds and recording materials containing the same

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