Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-01-25
1998-01-27
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
504155, 504156, 504221, A61K 3154, A01N 4334, A01N 4336, A01N 4372
Patent
active
057122750
DESCRIPTION:
BRIEF SUMMARY
The present invention concerns a method of controlling bacteria and fouling organisms with 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides, a method of protecting non-living materials other than wood, and industrial antibacterial and antifouling compositions. Surfaces of objects exposed to humid or aqueous environments are readily colonized by micro-organisms and occasionally by other, higher life forms such as molluscs and crustacea. As these organisms settle on or attach to said surfaces, the value of the exposed objects diminishes. The exterior, but possibly also the interior of the object may deteriorate, the surface changes (e.g. from smooth, clean and streamlined to rough, foul and turbulent), the weight of the object increases by the deposit of the organisms and their remnants, and the vicinity of the object may become obstructed or encumbered. The function of the object and system involved lowers and the quality of the aqueous environment deteriorates. Similar problems beset industrially used compositions such as coatings, lubricants and the like. All these phenomena are referred to as fouling. The oxathiazines of the present method and their oxides are disclosed in U.S. Pat. No. 4,569,690 as herbicides, plant fungicides, plant desiccants and defoliants.
The present invention provides a method of controlling bacteria and fouling organisms, said method comprising applying to said bacteria or fouling organisms, or to the locus thereof an effective antibacterial or antifouling amount of a compound having the formula ##STR3## wherein n is 0, 1 or 2; R.sup.1 is hydrogen, C.sub.1-4 alkyl or benzyl; and R represents (a) phenyl; phenyl substituted with 1 to 3 substituents independently selected from hydroxyl, halo, C.sub.1-12 alkyl, C.sub.5-6 cycloalkyl, trihalomethyl, phenyl, C.sub.1-5 alkoxy, C.sub.1-5 alkylthio, tetrahydropyranyloxy, phenoxy, C.sub.1-4 alkylcarbonyl, phenylcarbonyl, C.sub.1-4 alkylsulfinyl, C.sub.1-4 alkylsulfonyl, carboxy or its alkali metal salt, C.sub.1-4 alkyloxycarbonyl, C.sub.1-4 alkylaminocarbonyl, phenylaminocarbonyl, tolylaminocarbonyl, morpholinocarbonyl, amino, nitro, cyano, dioxolanyl or C.sub.1-4 alkyloxyiminomethyl; naphthyl; pyridinyl; thienyl, preferably when n is not 2; furanyl; or thienyl or furanyl substituted with one to three substituents independently selected from C.sub.1-4 alkyl, C.sub.1-4 alkyloxy, C.sub.1-4 alkylthio, halo, cyano, formyl, acetyl, benzoyl, nitro, C.sub.1-4 alkyloxycarbonyl, phenyl, phenylaminocarbonyl and C.sub.1-4 alkyloxyiminomethyl; or R represents a radical of formula ##STR4## wherein X is oxygen or sulfur; Y is nitrogen, CH or C(C.sub.1-4 alkyloxy); and R" is hydrogen or C.sub.1-4 alkyl.
The present invention in particular provides a method of protecting non-living materials other than wood, and the objects made of or covered by said non-living materials, against bacteria and/or fouling organisms, said method comprising applying to the surface or incorporating into said materials or objects an effective antibacterial or antifouling amount of a compound of formula (I).
In the foregoing definitions halo is generic to fluoro, chloro, bromo and iodo; C.sub.1-4 alkyl defines straight and branch chained saturated hydrocarbon radicals having from 1 to 4 carbon atoms comprising methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethylethyl, 1-methylpropyl, 2-methylpropyl; C.sub.1-5 alkyl includes C.sub.1-4 alkyl radicals as defined above and saturated hydrocarbon radicals having five carbon atoms, e.g. n-pentyl and the branched pentyl isomers; C.sub.1-6 alkyl includes C.sub.1-5 alkyl radicals as defined above and six carbon containing homologs, e.g. n-hexyl and the branched hexyl isomers. C.sub.1-12 alkyl includes C.sub.1-6 alkyl and saturated hydrocarbon radicals having from 7 to 12 carbon atoms, e.g. heptyl, octyl, nonyl, decyl, undecyl and their isomers. The term alkali metal cation in particular is a sodium or potassium cation. Trihalomethyl defines a methyl group being fully substituted with halo atoms, in particular trifluoromethyl
REFERENCES:
patent: 4569690 (1986-02-01), Brouwer et al.
Janssen Pharmaceutica N.V.
Metz Charles J.
Robinson Allen J.
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