DE1642057A1 - Use of substituted phenyl ethers as potentizing agents in antimicrobial agents - Google Patents

Description

New patent application D 3398

Use of substituted Phenylätherη as Potentiating agents in antimicrobial agents

The invention relates to the use of substituted phenyl ethers to increase the antimicrobial Effectiveness of phenolic disinfectants and quaternary ammonium compounds, as well as such bactericidal compounds containing compositions.

Phenolic compounds and quaternary ammonium compounds Due to their good disinfecting power, they are used in a wide variety of antimicrobial preparations Art. In addition to many advantageous properties, they also have disadvantages for some purposes, such as unpleasant smell, discoloration of the agents prepared with it, insufficient skin tolerance, etc. Use in the required amount to develop the full antimicrobial effect not always indicated? its J, aa- ^ sen. This often results in the need to use the ^

10 ^ 017/1933

tration of the bactericide, but with the Effectiveness of the antimicrobial agent should not suffer. In many cases it is also due to the influence of the other components an antimicrobial preparation back the effectiveness of the bactericide, so that to achieve a satisfactory Effect larger amounts of the phenolic compound or quaternary ammonium compound required became. However, this increase in the concentration of the bactericides mentioned cannot always be avoided without something else Carry out disadvantages.

The present invention is now based on the object of finding products which have the effectiveness of antimicrobial Are able to increase agents based on phenolic disinfectants and quaternary ammonium compounds in such a way that that a fraction of the previous amount of these compounds used is sufficient for a satisfactory effect or that the amount used if the effectiveness of the other components of the agent is adversely affected need not be increased.

This object is achieved by using substituted phenyl ethers of the general formula

10S8t7 / 1933

- Ο

in which R _{1 stands} for a lower aliphatic radical with 1-4 carbon atoms, which can be substituted by chlorine or hydroxyl groups or interrupted by an oxygen atom and Rq, ^R 3 * ^R 4 * ^R 5 and -Rg for hydrogen, chlorine, bromine and the like Iodine can represent a lower aliphatic radical with 1-4 carbon atoms, a phenyl or nitro radical, used as a potentiating agent in such antimicrobial agents which contain a bactericidal phenolic compound or quaternary ammonium compound.

The substituted phenyl ethers used are effective in themselves Disinfectants are "capable of antimicrobial activity even in low concentrations phenolic disinfectants or quaternary ammonium compounds.

As potentizing agents for phenolic disinfectants and quaternary ammonium compounds are basically all the above-mentioned substituted phenyl ethers are suitable.

109817/1933

, _. 16A2057

However, halogen atoms or nitro groups are preferred Use substituted phenyl ethers of the type mentioned. Among these, in turn, show halogen-substituted ones on the phenyl nucleus Phenyl ethers, the aliphatic ether component of which is substituted by a hydroxyl group or by an oxygen atom interrupted is the best suitability, since with their help antimicrobial compositions with particularly high effectiveness, d. H. Produce with, if necessary, particularly low bactericidal concentrations with satisfactory effectiveness permit.

Phenyl ethers substituted with chlorine or bromine atoms on the phenyl nucleus, the aliphatic ether component of which is substituted by a hydroxyl group, such as 2- (2'-chlorophenoxy) ethan-1-ol, 2- (4'-chlorophenoxy), have proven to be preferred substances ) -ethane-1-oil, 2- (2 ^!, 4'-dichlorophenoxy) -ethan-1-ol, 2-O'-methyl-4'-chlorophenoxy) -ethane-1-oil, 2 - (3 ^f -Methyl-4'-bromophenoxy) -ethane-1-oil, 2- (2 ', 4 ¹ , 6'-trichlorophenoxy) -ethanol-ol, 1-methyl-2 (2' -isopropyl-4 ¹ -bromo-5 ^1- methyI-phenoxy) -ethanl-ol, l-methyl-2- (2'-methyl-4 ¹ -bromophenoxy) -ethane-1-oil, 1-ethyl- 2- (2i-methyl-4'-bromophenoxy) -etha-il-ol, 1-methyl-2- (2 'chlorophenoxy) -ethan ~ l-ol have been proven.

- 5 -109817/1933

Substituted phenyl ethers which can be used as bactericidal or fungicidal agents are, for example, 3-methyl-4-chloro-phenylmethyl ether, 3,5-dimethyl-4-chloro-phenylmethyl ether, 2,4,6-trichloro-phenyl-ethyl ether , 3- (5 ', 5'-dimethyl-4 ^f -chloro-phenoxy) -propene-l, 3- (2] 4', 6'-trichlorophenoxy) -propene-1, 2-phenoxy-ethane-l- ol, 2- (j5'-methylphenoxy) -ethan-1 ~ ol, 2- (2'-methyl-phenoxy) -ethane-1-oil, 2- (4 ^! -tert.Butyl · pheϊloxy) -ethane-1 -ol _> 2- (2 ', 5'-dimethylphenoxy) -ethan-1-ol, 2- (3 ** 5'-dimethylphenoxy) -ethane-1-oil, 2- (2'-isopropyl-5 '-methyl-phenoxy) -ethane-1 oil, 2- (2 ^f -Phenylphenoxy) -ethane-1-ol, 2- (2'-chloro-phenoxy) -ethane ~ l-ol, 2- (4 ^f -Chlorophenoxy) -ethane-1-oil, 2- (2 ', 4 ^! -Dichlorophenoxy) -ethan-1-ol, 2- (2', 4 ^f , 6'-trichlorophenoxy) -ethane -1-oil, '2- (4'-iodo-phenoxy) -ethan-l-ol _i 2- (J ¹ -Methyl- * ¹ -chlorphenoxy) -ethane-1-oil, 2- (3', 5 '-Dirnethyl-4 ¹ »chloro-phenoxy) -ethane-1 -oil, 2- (3' -methyl-4 '-broni-phenoxy) -ethane-1 -oil, 2- (4-nitro-phenoxy ^r) -ethan ~ l-ol, 1-methy1-2- (phenoxy) -ethari-1-ol, l-ethyl-2- (phenox y) -ethan-1-ol, 1-methyl-2- (3 ^l »5 -dimethylphenoxy) -ethane-1-oil, l-methyl-2- (2 ^f -isopropyl-5'-metal-yl -phenoxy) -ethane-1-oil, 1-ethyl-2- (J ', 5' dimethyl-phenoxy-ethane-1-oil, 1-ethyl-2- (2'-isopropyl-5'-methyl -phenpxy) -ethane-1 oil, 1-Me thy 1-2- (2 '-chloro -phenoxy) - · ethane-1-ol, l-methyl-2 ~ ^(4-bromo-t phenoxy) "ethane -l-ol,

■ '■■ · "_. · · -6- 109817/1933

1 -Xthyl-2- (2'-chlorophenoxy) -ethane-1-oil, 1 -ethyl-2- (4 * brorr.-phenoxy) -ethane-1-oil, I-methyl-2- (V -iodo-phenoxy) -ethane-l ~ ol, _l ~ ethyl-2- (V-iodo-phenoxy) -ethan-l-ol, 1-methyl-2- (2'-methyl-4'-bromo -phenoxy) -ethane-1-oil, 1-ethyl-2- (2'-methyl-4'-bromo-phenoxy) -ethane-1-oil, l-methyl-2- (4'-bromo-3 ' , 5'-dimethyl-phenoxy) -ethane-1 oil, 1-ethyl-2- (4'-bromo-3 ^1, 5'-dimethyl-phenoxy) -ethane-1 oil, l-methyl-2- (4'-bromo-5'-methyl-2'-isopropyl-phenoxy) -ethane-1-oil, l-ethyl-2- (4'-bromo-5'-methyl-2'-isopropyl-phenoxy) - Ethanol-ol, 1-ethyl-2 "(2'-nitro-phenoxy) -ethane-1-oil, 1-chloro-2-phenoxy-ethane, 1-chloro-2- (2'-methyl-phenoxy) - Ethane, 1-chloro-2 - (^ ^! -methyl-phenoxy) -ethane, 1-chloro-2- (2'-phenylphenoxy) -ethane, 1-chloro-2- (2 ⁱ -chlorophenoxy) -ethane , 1-chloro-2 - (^ '- methyl-4 ·' -chlorophenoxy) ethane, (jJ-methylphenoxy) -. methyl-ethyl-ether, (^ -Chlor-phenoxyJ-methyl-ethyl-ether.

The potentizing agents according to the invention can be used in conjunction with all antimicrobial phenolic. Compounds and quaternary ammonium compounds used be prepared to the activity of these or to dar with these Increase compositions.

-7-

109817/1933

Suitable bactericides of the phenolic type are: phenol, cresol, xylenol, p-chlorophenol, o-chlorophenol, ρ-bromophenol, p-chloro-m-cresol, 3,5-dimethyl-pchlorophenol, ο-benzyl-ρ- chlorophenol, 2,4,6-trichlorophenol, pentachlorophenol, sodium pentachlorophenolate, sodium-ophenyl-phenolate, resorcinol, methylresorcinol, phenylresorcinol, benzylresorcinol, p-chlorobenzylresorcinol, 4-n-octylpyrogallol, benzylpyrogallol, 2,2'-methylene-bis- ( 4-chlorophenol), 2,2'-. Methylene bis (3,4,6-trichlorophenol), 2,2'-methylene bis (4-chloro-3i5-xylenol), o-hydroxybenzoic acid, m-hydroxybenzoic acid, propyl-p-hydroxybenzoate, dibromo-, Dichloro-, trichloro-, tribromosalicylanilide, trifluoromethylhalosalicylanilide, m-nitrophenol, p-nitrophenol, o-nitrophenol, 2,5-dinitrophenol, 2,4,6-trinitrophenol, 3-nitro-4-hydroxybenzoic acid, ρ-aminophenol, 2,4-diaminophenol, bis- (p-hydroxypheny1) -methylene, 2,2'-dihydro ^ -J, 5,6,3 ', 5', 6'-hexachlorodiphenylmethane, J, -naphthol, ß-naphthol, Tetrabromonaphthol, 8-oxyquinoline, phenyl-mercury-8-oxyquinoline.

Suitable quaternary ammonium compounds are cationic surface-active compounds in which a substituent on the quaternary nitrogen atom is hydrophobic, i.e. a chain

109817/1933

ten length of Cg-C, η, such as dimethyldodecylbenzylammonium chloride, Diethyl-dodecyl-benzylammonium chloride, dichlorobenzyl-dimethyl-alkyl-ammonium-. chloride (trade name Benzalkon B), dimethyl-octadeeyldimethylbenzyl-ammonium chloride, Dimethyl-didecyl-ammonium chloride, Dimethyl-didodecyl-ammonium chloride, trimethyltetradecyl-ammonium chloride, Methyl diethyl decyl oxyethylammonium bromide, N-trimethyl-N-chloro-N'-benzyl-N'-dodecylglycine amide, Cetylpyridinium chloride, 2-tridecylpyridinium sulfate, 1-hexadecyl-pyridinium chloride, 2-dodecyl-isoquinolinium bromide, 2-octyl-l- (2-hydroxyathyl) imidazolinium chloride, o-dodecyloxybenzylquinolinium chloride, benzyldeoylpiperidinium chloride.

The substituted phenyl ethers used as potentiating agents can be prepared according to generally known methods Procedure. Substituted phenyl ethers, the aliphatic ether component of which is unsubstituted Represents hydrocarbon radical, by reacting equivalent amounts of the correspondingly substituted phenol with the appropriate halogenated hydrocarbon in acetone in the presence of potassium carbonate and fractionated by Work up the distillation. The manufacture of the

■ ■ '-9-'

109817/1933

Phenyl ethers, in which the aliphatic ether component - is a hydrocarbon residue substituted by a hydroxyl group, was carried out by adding 1 mol of ethylene oxide, propylene oxide or butylene oxide to 1 mol of the correspondingly substituted phenol. For this purpose, 1 mol of phenol, and 1% jio% were submitted lges sodium methylate in an autoclave, then ° C for 15 minutes vacuum was at 80-120 purged with nitrogen at 80-120 ° C and then applied from 100 150 ⁰ C. 1 to 1.1 Moles of the corresponding alkylene oxide added on. Work-up was carried out by fractional distillation. The substituted phenyl ethers, the aliphatic ether component of which is substituted by halogen, were prepared from the 2-phenoxy-ethan-1-ols by reaction with thionyl chloride and working up by fractional distillation. For the preparation of phenyl ether, the aliphatic ether component is interrupted by oxygen, the appropriately substituted phenate in an equivalent amount with was chloromethyl ethyl ether in benzene at 20 ⁰ C, stirred for 8 hours at 60 ° C and then worked up by fractional distillation.

The ratio of potentiating s phenolic compound or quaternary ammonium compound depends on the intended use of the anti !! IiIaObIeIlen composition from "It is therefore in all those cases where the adverse properties of the phenolic bactericides or quaternary ammonium compounds are particularly disturbing, try using 109817 / 1933 · " _10-

get by with the smallest possible quantities of these products, as far as a reduction by increasing the potency

rungsmittel is feasible. In many cases one will deal with the pricing with a lower consideration Have to be satisfied with increased effectiveness and even larger amounts of phenolic compound or quaternary Ammonium compound in the antimicrobial composition insert. The weight ratio of potentiating agents : phenolic compound or quaternary ammonium compound is preferably within the limits 1: 2.5 move up to 1000: 1.

The inventive antimicrobial combinations from Potentiating agents and phenolic compound or quaternary ammonium compound can generally be used for all those disinfection purposes are used for which the phenolic compounds and quaternary Ammonium compounds are used alone, such as antiseptic cleaning agents for hands, textiles, floors, Hospital equipment and instruments, antiseptic shampoos, antimicrobial ointments, liniments, Powders, cleaning agents and disinfectants for commercial operations such as dairies, breweries and laundries.

The following examples will make the subject matter this application explained in more detail.

-11-

109817/1933

The inhibitory concentrations of the phenols to be examined Compounds, quaternary ammonium compounds and the combinations of these products with the various potentiating agents were determined with the help of the so-called plate test. This test is a modified version of the guidelines for testing chemical disinfectants of the German Society for Hygiene and Microbiology among the methods for preliminary testing of such Means described dilution test to determine the microbiostatic effect and can be used with advantage Use liquid culture media for various tests instead of the use specified there.

The desired test concentrations became more suitable by mixing measured amounts of the substance solutions Liquefied concentrations with measured amounts Broth agars prepared in sterile Petri dishes. The pipetted amounts of the substance solutions were 0.1 up to a maximum of 1 ml, the total volume in the Petri dishes after mixing with the nutrient medium 10 ml. After solidification of the nutrient medium, the surface was

germ suspension inoculated in bouillon, which per ml approx. 10 Contained germs. The incubation took place at 37 ° C in the incubation

-12-

109817/1933

cupboard and lasted 8 days. It was subsequently determined which substance concentration incorporated into the nutrient medium does not affect the growth of the test; just completely under- ■ could bind. This value determined in this way was used as the inhibitory concentration designated. The tests were carried out at the following concentration intervals: 10,000, 5,000, 2,500, 1,000, 750, 500, 250, 100, 50, 25, 10, 5 ,.

2.5, 1, 0.5, 0.25, 0.1 ppm.

In these plate tests, the inhibitory concentrations listed in the tables below were determined.

The phenolic compounds to be tested were:

A xylenol B sodium pentachlorophenolate

C phenyl-mercury-8-oxyquinoline D 2,2'-methylene-bis-trichlorophenol .-

The quaternary ammonium compounds examined were

E cetyl pyridinium chloride

F dichlorobenzyl-dimethyl-alkyl-ammonium chloride d

1098 17/1933

D 3398

The following substances were used as potentizing agents:

G 3,5-dimethyl-4-chlorophenyl methyl ether (bp ^ = 105-106 ° C)

H 3- (2 ', 4 ^!, 6'-Trichlorophenoxy) -propen-1 (Pp = 45 ° C from

Ethanol)

I 2-phenoxy-ethan-l-ol (bp ₁ ^ = 121-122 ° C)

K 2- (3'-methyl-phenoxy) -ethan-l-ol (bp ₁ I ₁ = 133-134 ° C)

L 2- (4'-tert-butyl-phenoxy) -ethan-l-ol (bp _{n χ} = 102-103 ° C)

M 2- (2'-phenyl-phenoxy-ethan-l-ol (Kp _{n Q} ^ ~ 119-121 ⁰ C)

N 2- (4'-chloro-phenoxy) -ethane-l-oil (Kp _l2f = l6l-l62 ° C)

O 2- (2 '_>4'-dichlorophenoxy) -ethan-l-ol (bp ₁₁ , = 168-17O ° C)

P 2- (2 ', 4', 6'-trichlorophenoxy) -ethan-1-ol (Pp = 65-67 ⁰ C from

Petrol)

Q 2- (4'-iodo-phenoxy) -ethan-l-ol (bp ₁ = l46 ° C)

R 2- (3'-methyl-4'-chloro-phenoxy) -ethane-l-ol _(Kp. = 104

° ' ^L 105 ° C)

S 2- (3 ', 5'-dimethyl-4'-chlorophenoxy) -ethane-1-oil (Kp _{n χ} =

121-123 ° C) T 2- (3'-methyl-4'-bromophenoxy) -ethan-l-ol (bp ₁ ^ = 169-170 ° C)

U 2- (4'-nitro-phenoxy) -ethane-1-oil (Pp = 91-92 ° C from chloroform)

V 1-methyl-2- (2 ^t -isopropyl-5 ^r -methyl-phenoxy) -ethan-1-ol

W l-methyl-2- (2'-chlorophenoxy) -ethane-l-ol (bp ₂ ^ = 123 ° C) X l-methyl-2- (4'-iodo-phenoxy) -ethane-l- oil (bp ₁ = l4l-l42 ° C)

Y 1-methyl-2- (2'-methyl-4'-bromophenoxy) -ethan-1-ol

(KP3 =! 500C)

-14- 109817/1933

Z l-Ethyl-2- (2'-methyl-4'-bromophenoxy) -ethan-1-ol

( ₅ = 156 ° C)

A l-methyl-2- (4'-bromo-5'-methyl-2 ^f -isopropyl-phenoxy) -ethan-1-ol (bp ₁ ^ = l65-166 ° C)

l-chloro-2- (3'-methyl-4'-chlorophenoxyj-ethane (Κρ _{χ2 |} =

109817/1933

(3-methyl-phenoxy) -methyl-ethyl-ether (bp ₁ ^ = 94-96 ° C) -TL (4-chloro-phenpxy) -methyl-ethyl-ether (bp ₁ ^ = 126-128 ° C)

-15-

The test germ for the experiments listed in Table I was used to determine the inhibitory concentration Staphylococcus aureus.

Table I.

Of infection - hernia concentration,

middle

in onm

Potentiation inhibition concentration, medium in ppm

Inhibition Conc. the combination of disinf. + Potency, in ppm

relationship

Disinfect.

Power.

500

CO CjO Approx

G H I K L M N O P Q T U V X Y Z

τ Ψ

10 000 100 10 000 100 2 500 100 2 500 100 2 500 100 CvJ 500 100 500 50 250 50 250 50 250 100 100 25th 500 50 500 50 500 100 250 25th 500 25th 25th 25th 2 500 100 5 000 100 1 000 100

2500

2500

500

500

500

.100

250

100

100

100 100 100

100 10

500

1000 100

1

2.5

1 1 1

25 25

5 1

1. "2 1 2

2 · 2 1 2

1

10

ι

Table I.

Of infection inhibition.

medium in ppm

Potentiation inhibition conc. Inhibition Conc. the combination

relationship

middle

in ppm

Disinfect. + Potency, in ppm disinfection.

power

T)
JJ

C.
O

25th

2.5

2.5

'S W P

R H K R

2,500

100

• 500

250

100

10,000

2,500

100

5
2.5

■ °> 5

0.5
2.5
1

2.5

250 25

100 50

25 5Ö0 000

25th

■ 1 1 1 1 1 1 1 1

50

10 200

50 50

000 000

10

cc
co
cu

For oils In Table II, tests to determine the inhibitory concentration were used as the test germ Escherichia coil.

Of the infection keroma concentration *

medium in ppm

medium ■ jftjgftrc ^{Pes: i} - ^nf **

Heremkon; ζ. Bemmk ' 5000 250 5000 100 1000 50 500 50 500 250 5000 250 5000 250 5000 10 5000 25th 5000 50 500 25th 500 50. 500 25th 500 25th 5000 250 2500 250 5000 250 500 100

Ratio Deslnf,: Potency ,

500

5OO

100

1000

500

P B

K K

K E E

1000 1000

250

100 100

500

1000 1000

500 250

100

50

100

500

1000

500 500 250

1 1 1 1 2.5 1 1 1 1 1 1 ■ 1 i 1 1 1 1 1

10 '

2.5 20

20 '. 4th

2 ". 2.5

The following are compositions for some initial microbial Means indicated.

AntiBicrobial Powder

2 _J , 2 ^t -Methylene-bis-triehlophenol O, 5 parts by weight.

(Hexachlorophene)

2- (2% 4% 6'-Triehlor-phenoxy) -ethan-1-ol 0.5 Talcum venetad 100

Antiroicrobial ointments

2.2 ^f -ethylene bis trichlorophenol 0.5

2- (5 ^t -methyl-4 ^t -chlorophenoxy) -ethan-1-ol. 0.5 Vaseline alba ad 1OO

Tribromosalicylanilide 0.4

1 -Methyl-2- (2 ^f -methyl-4 ^r -bromophenoxy} -

Ethan-1-ol 0.5 "

Polyethylene Glycol 300 + Polyethylene

glycol 1500 lsi ad 1OO "

Disinfectants for facilities and instruments

2- (3 * -methyl-4-chlorophenoxy) -

Ethan-1-ol 10 "

Benzalkon B 2.5 "

Isopropanol 40 ^w

Water 4? »5 *

- ■

10 5 Parts by weight ο, 5 It ι, ti 1 Il 87 It 100 ti

De sodorant spray

2-octy1-dodecano1 2,2'-non-ethylene-bis-trichlorophenol.

2- (2 ^f , 4'-dichloro-phenoxy) -ethane-1-oil perfume

Ethanol

Propellant

De sodorant pen

Stearyl alcohol 2-octyldodecanol Coconut fatty acid monoethanolamide stearic acid monoethanolamide carnauba wax Paraffin 72 ° C perfume oil

1,2 propylene glycol 2,2'-methylene-bis-trichlorophenol

2- (5'-methyl-4'-chlorophenoxy) -ethane-1-oil

Disinfectant hand vjasch paste

Sodium lauryl sulfate, coconut fatty acid monoethanolamide, finely ground pumice stone 2,2'-methylenebis-trichlorophenol 2- (2 ', 4 * -dichlorophenoxy) -ethane-1-oil

109817/1933 -19-

10 11 ■ ίο dd 10 It 15th It 2 ti 10 It 2 It 58 It 1.5 Il 1.5 Il

52 11 It 41 It 2 It 2 It

ίο

Parts by weight 2 Il 8th It 30th Il 1 Il 2 Il 2 It 25th Il

Antimicrobial mild detergent

Dodecylbenzenesulfonate Toluo Lsulfonate

Sodium coconut fatty alcohol sulfate sodium sulfate

Sodium carboxymethyl cellulose 2,2'-methylene-bis-trichlorophenol

2 - (^ '- methyl-4'-chlorophenoxy) -ethan-1-ol

water

Antiseptic shampoo clear

Sodium Lauryl Ether Sulphate (27-28 % WHAT)

Coconut fatty acid diethanolamide 2,2'-methylene-bis-trichlorophenol

2- (3'-methyl-4'-chlorophenoxy) -ethan-1-ol

water

The advantage that can be achieved with the combination according to the invention is that it is possible to control the concentration of the disinfectant in the antimicrobial agent

40 Il 6th ti 2 Il 2 Il 50 ti

-20-

10981 7/1 933

a-i

largely without reducing its germicidal effect. This is of particular importance in all cases when harmful or unpleasant side effects are triggered by higher concentrations of the disinfecting substance. Another advantage is that the combination with the potentiating agent improves the weak activity of quaternary ammonium compounds, and in some cases also of bisphenols, against green-negative bacteria in many cases.

109817/193 3-

Claims (1)

Claims in the R, for a lower aliphatic radical with 1-4 carbon atoms, which is replaced by chlorine or hydroxyl groups may be substituted or interrupted by an oxygen atom and Rp, R ^, R ^, R ^ and Rg for Hydrogen, chlorine, bromine, iodine, a lower aliphatic radical with 1-4 carbon atoms, a phenyl or nitro residue can stand as a potentiating agent in an antimicrobial agent that is a bactericidal phenolic compound or quaternary ammonium compound contains. 2. Use of phenyl ethers substituted by halogen atoms or nitro groups according to claim 1. -22- 109817/1933 32 » j5. Use of halogen-substituted on the phenyl nucleus Phenyl ethers, the aliphatic ether component of which is substituted by a hydroxyl group or by e..n Oxygen atom is interrupted, according to claim 1 and 4. Use of substituted on the phenyl nucleus by chlorine or bromine Phenyl ethers, the aliphatic ether component of which is substituted by a hydroxyl group. 5. Use of 2- (2 ^f -chlorophenoxy) -ethan-l-ol according to claims 1-4. 6. Use of 2- (4 ^l -chlorophenoxy) -ethan-l-ol according to claims 1-5 7. Use of 2- (2 ', 4'-dichlorophenoxy) -ethan-1-ol according to claims 1-6. 8. Use of 2- (2 ^l , 4 ^l , 6'-trichloro-phenoxy) -ethan-l-ol according to claims 1-7 9. Use of 2- (3 ^l -methyl-4'-chlorophenoxy) -ethan-l-ol according to claims 1-8. 109817/1933 Henkel & Cie GmbH Patent department
D. 10. Use of 2- (j5'-methyl-4'-bromophenoxy) -ethan-1-ol according to claim I-9. 11. Use of 1-methyl-2- (2'-isopropyl-4'-bromo-5'-methyl-phenoxy) -ethan-1-ol according to claims 1-10. 12. Use of l-methyl-2- (2'-methyl-4 '-br pm-phenoxy) -ethan-1-ol according to claim 1-11. 15. Use of 1-ethyl-2- (2'-methyl - ^ '- bromophenoxy) -ethan-1-ol according to claims 1-12. 14. Use of l-methyl-2- (2'-chlorophenoxy) -ethan-1-ol according to claim 1-13 15. Use of substituted phenyl ethers in combination with phenolic compounds or quaternary ammonium compounds according to claims 1-14, wherein the Weight ratio of potentiating agent to disinfectant is in the limits 1: 2.5 to 1000: 1. Henkel & Cie. GmbH, ppa. ■. i.V. (Dr Haas) Future) 109817/1933