Microbicidal active substances

Details Microbicidal active substances Microbicidal active substances

2000-02-01

2004-02-10

Padmanabhan, Sreeni (Department: 1619)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C424S401000, C514S360000, C514S439000, C514S448000

Reexamination Certificate

active

06689372

ABSTRACT:

The present invention relates to the use of oxathiazolones in the antimicrobial treatment of surfaces.
The oxathiazolones used according to the invention correspond to formula
wherein
R
1
, is C
1
-C
16
alkyl, C
2
-C
16
alkenyl or C
5
-C
8
cycloalkyl, each unsubstituted or substituted by halogen, —CN, —NO
2
, —C═O, —C═S, —NR
2
, —OR
3
, —SR
4
, —SO
2
R
5
, —COOR
6
or by a 1,3,4-oxathiazol-2-one radical; C
6
-C
10
aryl unsubstituted or substituted by one or more C
1
-C
5
alkyl, C
6
-C
10
aryl, halogen, hydroxy, acyl, —CN, —CF
3
, —NO
2
, —NR
2
, —OR
3
, —SR
4
, —SO
3
H, —SO
2
R
5
, —COOR
6
substituents or by a 1,3,4-oxathiazol-2-one radical; or a 5- or 6-membered heterocyclic radical;
R
2
and R
3
are each independently of the other hydrogen; C
1
-C
5
alkyl; C
6
-C
10
aryl, or acyl;
R
4
is hydrogen; C
1
-C
5
alkyl; or C
6
-C
10
aryl;
R
5
is C
1
-C
5
alkyl; or C
6
-C
10
aryl;
R
6
is hydrogen; C
1
-C
5
alkyl; or C
6
-C
10
aryl.
C
1
-C
16
Alkyl are straight-chain or branched alkyl radicals, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl or hexadecyl.
C
2
-C
16
Alkenyl is e.g. allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, 3,6,8-decatrienyl or isododecenyl.
C
6
-C
10
Aryl can be a mono- or bi-cyclic aromatic radical, e.g. phenyl or naphthyl.
C
5
-C
8
Cycloalkyl can be cyclopentyl, cycloheptyl, cyclooctyl or preferably cyclohexyl.
Examples of 6-membered heterocyclic radicals are pyranyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, piperazinyl, indolinyl and morpholinyl.
Examples of 5-membered heterocyclic radicals are thienyl, furyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, isoxazolyl, furazanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolidinyl and pyrazolinyl.
The 5- or 6-membered heterocyclic radicals can be unsubstituted or substituted by halogen, such as chlorine or bromine, nitro, C
1
-C
5
alkyl or by C
1
-C
5
alkoxy.
According to the invention, preference is given to the use of compounds of formula (1) wherein
R
1
is C
1
-C
16
alkyl unsubstituted or substituted by halogen, —CN, —NO
2
, —C═O, —C═S, —NR
2
, —OR
3
, —SR
4
, —SO
2
R
5
, —COOR
6
or by a 1,3,4-oxathiazol-2-one radical; or C
6
-C
10
aryl unsubstituted or substituted by one or more C
1
-C
5
alkyl, C
6
-C
10
aryl, halogen, hydroxy, acyl, —CN, —CF
3
, —NO
2
, —NR
2
, —OR
3
, —SR
4
, —SO
3
H, —SO
2
R
5
, —COOR
6
substituents or by a 1,3,4-oxathiazol-2-one radical; and
R
2
, R
3
, R
4
, R
5
and R
6
are as defined for formula (1).
Special preference is given to compounds of formula (1) wherein
R
1
is C
1
-C
16
alkyl; especially C
1
-C
12
alkyl and more especially methyl or ethyl.
According to the invention, use is also preferably made of oxathiazolones of formula
wherein
R
7
, R
8
and R
9
are each independently of the others hydrogen; halogen; hydroxy; or C
1
-C
5
alkyl.
Examples of compounds that can be used according to the invention correspond to formulae
In formula (7), R=—CH
3
; or —(CH
2
)
10
CH
3
.
The compounds of formulae (1) to (8) are known in the literature. The compound of formula (9) is a new compound.
The preparation of the oxanilides used according to the invention is effected in accordance with known procedures by reacting a carboxylic acid amide of formula
with chlorocarbonylsulfenic acid chloride, corresponding to formula
in accordance with the following scheme:
wherein R
1
is as defined for formula (1).
The starting materials corresponding to formula (7) are known. Chlorocarbonylsulfenic acid chloride (compound of formula (11)) is a known reagent of organic chemistry.
The preparation process is preferably carried out without an acid acceptor but can also be carried out in the presence of a suitable acid acceptor. As such there come into consideration all customary organic and inorganic bases. These include, for example, alkaline earth metal and alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates and hydrogen carbonates, e.g. sodium hydride, sodium amide, sodium methanolate, sodium ethanolate, potassium tert-butanolate, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, sodium potassium carbonate or hydrogen carbonate, ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine, N-methylpiperidine and N,N-dimethylaminopyridine.
The process is preferably carried out in the presence of a solvent. All customary organic solvents come into consideration for that purpose. These include especially aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, e.g. benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as dimethyl ether, diethyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether, ketones, such as acetone, butanone and methyl isobutyl ketone, nitriles, such as acetonitrile, propionitrile and benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N,N-methylformanilide, N-methyl-pyrrolidone and hexamethylphosphoric acid triamide; esters, such as methyl acetate and ethyl acetate, sulfoxides, such as dimethyl sulfoxide, preferably hydrocarbons. Special preference is given to toluene and dioxane.
The reaction temperatures can be varied within a wide range. The operation is generally carried out at temperatures of from −10 to +180° C., preferably at temperatures of from 20 to 130° C.
The process is usually carried out under normal pressure, but may also be carried out at elevated or reduced pressure.
For carrying out the process, generally from 1 to 10 mol, preferably from 1.0 to 3 mol, of chlorocarbonylsulfenic acid chloride are used per mole of carboxylic acid amide of formula (10).
The oxathiazolones used according to the invention exhibit a pronounced antimicrobial action, especially against pathogenic gram-positive and gram-negative bacteria and also against bacteria of skin flora, e.g.
Corynebacterium xerosis
(bacteria that cause body odour), and also against yeasts and moulds. They are therefore especially suitable in the disinfection of the skin and mucosa and also of integumentary appendages (hair), more especially in the disinfection of the hands and of wounds.
They are therefore suitable as antimicrobial active ingredients in personal care preparations, for example shampoos, bath additives, hair-care products, liquid and solid soaps (based on synthetic surfactants and salts of saturated and/or unsaturated fatty acids), lotions and creams, deodorants, other aqueous or alcoholic solutions, e.g. cleansing solutions for the skin, moist cleansing cloths, oils or powders.
The invention therefore relates also to a personal care preparation comprising at least one compound of formula (1) as well as cosmetically tolerable carriers or adjuvants.
The personal care preparation according to the invention comprises from 0.01 to 15% by weight, preferably from 0.5 to 10% by weight, based on the total weight of the composition, of the oxathiazolone compound of formula (1), and cosmetically tolerable adjuvants.
Depending upon the form of the personal care preparation, it will comprise, in addition to the oxathiazolone compound of formula (1), further constituents, for example sequestering agents, colourings, perfume oils, thickening or solidifying (consistency regulator) agents, emollients, UV absorbers, skin-protective agents, antioxidants, additives that improve mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca and Mg salts of C
14
-C
22
fatty acids, and optionally preservatives.
The personal care preparation according to the invention may be formulated as a water-in-oil or oil-in-water emulsion, as an alcoholic or a

Affiliated with

Also associated with

Rating

Microbicidal active substances does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Microbicidal active substances, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Microbicidal active substances will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3294098