Antibacterial and antifouling oxathiazines and their oxides

• US 5,922,113 A
• Filed: 10/16/1997
• Issued: 07/13/1999
• Est. Priority Date: 08/24/1993
• Status: Expired due to Term

• Current Assignee: Janssen Pharmaceutica NV (Johnson & Johnson)
• Original Assignee: Janssen Pharmaceutica NV (Johnson & Johnson)
• Inventors: Van Gestel, Jozef Frans Elizabetha
• Primary Examiner(s): GREEN, ANTHONY J
• Application Number:
  US08/951,278
• Time in Patent Office: 635 Days
• Field of Search: 106/18.33, 106/18.34, 106/18.35, 514/222.5, 504/155, 504/156, 504/221, 544/2, 523/122
• US Class Current: 106/18.33
• CPC Class Codes: A01N 43/88 six-membered rings with three ring hetero atoms
• CPC Class Codes: C07D 291/06 Six-membered rings
• CPC Class Codes: C07D 419/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C09D 5/1625 organic

Abstract

Use of 3-aryl-5,6-dihydro-1,4,2-oxathiazines and their oxides having the formula ##STR1## wherein n is 0, 1 or 2; R¹ is hydrogen, C_1-4 alkyl or benzyl; and R represents (a) phenyl; phenyl substituted with 1 to 3 substituents independently selected from hydroxyl, halo, C_1-12 alkyl, C_5-6 cycloalkyl, trihalomethyl, phenyl, C_1-5 alkoxy, C_1-5 alkylthio, tetrahydropyranyloxy, phenoxy, C_1-4 alkylcarbonyl, phenylcarbonyl, C_1-4 alkylsulfinyl, C_1-4 alkylsulfonyl, carboxy or its alkali metal salt, C_1-4 alkyloxycarbonyl, C_1-4 alkylaminocarbonyl, phenylaminocarbonyl, tolylaminocarbonyl, morpholinocarbonyl, amino, nitro, cyano, dioxolanyl or C_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_1-4 alkyl, C_1-4 alkyloxy, C_1-4 alkylthio, halo, cyano, formyl, acetyl, benzoyl, nitro, C_1-4 alkyloxycarbonyl, phenyl, phenylaminocarbonyl and C_1-4 alkyloxyiminomethyl; or R represents a radical of formula ##STR2## wherein X is oxygen or sulfur, Y is nitrogen, CH or C(C_1-4 alkyloxy); and R" is hydrogen or C_1-4 alkyl, as an antibacterial, anti-yeast, antifungal, algicidal, anticrustacean, molluscicidal and general antifouling agent and compositions containing the same.

Claims

1. A coating composition in the form of a paint, varnish, lacquer or whitewash comprising:

a) as active ingredient an effective antibacterial or antifouling amount of a compound of formula I ##STR10## wherein n is 0, 1 or 2;

R is hydrogen, C_1-4 alkyl or benzyl; and

R represents phenyl;

phenyl substituted with 1 to 3 substituents independently selected from hydroxyl, halo, C_1-12 alkyl, C_5-6 cycloalkyl, trihalomethyl, phenyl, C_1-5 alkoxy, C_1-5 alkylthio, tetrahydropyranylox, phenoxy, C_1-4 alkylcarbonyl, phenylcarbonyl, C_1-4 alkylsulfinyl, C_1-4 alkylsulfonyl, carboxy or its alkali metal salt, C_1-4 alkyloxycarbonyl, C_1-4 alkylaminocarbonyl, phenylaminocarbonyl, tolylaminocarbonyl, morpholinocarbonyl, amino, nitro, cyano, dioxolanyl or C_1-4 alkyloxyiminomethyl;

naphthyl;

pyridinyl, thienyl;

furanyl;

or thienyl or furanyl substituted with one to three substituents independently selected from C_1-4 alkyl, C_1-4 alkyloxy, C_1-4 alkylthio, halo, cyano, formyl, acetyl, benzoyl, nitro, C_1-4 alkyloxycarbonyl, phenyl, phenylaminocarbonyl and C_1-4 alkyloxyiminomethyl;

or R represents a radical of formula (II) ##STR11## wherein X is oxygen or sulfur;

Y is nitrogen, CH or C(C_1-4 alkyloxy); and

R" is hydrogen or C_1-4 alkyl, and

(b) polymers or copolymers derived from monomers selected from the group consisting of dialkyl siloxanes, (meth)acrylic acid, (meth)acrylic acid esters, vinyl and allyl alcohols and derived esters, maleic acid, styrene, vinylchloride, butadiene, acrylamide, acrylonitrile, and resins selected from the group consisting of alkyd resins, polyurethanes, epoxy resins, phenolic resins and ureaformaldehyde resins.

2. A coating composition according to claim 1 further comprising one or more additives selected from the group consisting of water-repelling agents;

surface slipping agents;

organic binding agents;

insecticides;

fungicides;

bactericides;

auxiliary solvents;

processing additives;

fixatives;

plasticizers;

UV-stabilizers or stability enhancers;

dyes;

color pigments;

siccatives;

corrosion inhibitors;

antisettling agents;

anti-skinning agents; and

antifoaming agents.

3. A coating composition according to claim 1 in the form of a paint, wherein the active ingredient is present in an amount of from 0.5% to 20% by weight of the composition.

4. A coating composition according to claim 1 in the form of a paint, wherein the active ingredient is present in an amount of from 1 to 10% by weight of the composition.

5. A coating composition according to claim 1 in the form of an antifouling paint composition comprising up to 50% of the active ingredient by weight based on the total weight of the antifouling paint composition.

6. A coating composition according to claim 1 in the form of an antifouling paint composition comprising from 5 to 25% of the active ingredient by weight based on the total weight of the antifouling paint composition.

7. A coating composition according to claim 1, wherein the compound of formula I is 5,6-dihydro-3-(2-thienyl)-1,4,2-oxathiazine, 4-oxide or 3-(4-chlorophenyl)-5,6-dihydro-1,4,2-oxathiazine, 4,4-dioxide.

8. A coating composition according to claim 6, wherein the compound of formula I is 5,6-dihydro-3-(2-thienyl)-1,4,2-oxathiazine, 4-oxide or 3-(4-chlorophenyl)-5,6-dihydro-1,4,2-oxathiazine, 4,4-dioxide.