DE1642062B2 - ANTIMICROBIAL AGENTS - Google Patents

Description

in which Y is chlorine or a nitro group, η the numbers 0 to 2. R is hydrogen or a methyl radical, B is hydrogen, a methyl radical, an ethyl radical or a phenylcarbamic acid ester group of the formula

—C — O — CH

Il I

ο R

represents. according to patent 1668 195, characterized by a content of 2-bromo-2-nitrobuty 1 - N - phenylcarbamate and 2 - brorr, - 2 - nitrobutyl - N - (3,4 - dichlorophenyl) - carbamate in a weight ratio of 1: 4 to 4: 1.

2. Antimicrobial agents according to claim 1, characterized due to a content of 2-bromo-2-nitrobutyl - N - phenj! carbamate and 2 - bromo - 2-nitrobutyl - N - (3,4 - dichlorophenyl) - carbamate in a weight ratio of 1: 1.

The subject of patent 16 68195 are bromonitroalkyl-N-phenylcarbamates the formula

NO ₂ I NH-C-O-CH-C-Br

I! I I

O RB

Y.

in which Y is chlorine or a nitro group, η the numbers up to 2, R is hydrogen or a methyl radical, B is hydrogen, a methyl radical, an ethyl radical or a phenylcarbamic acid group of the formula

Y.

^ NH-C-O-CH-O R.

represents.

The patent also relates to antimicrobials at 0.05 to 5%. preferably 0.1 up to 1%. the bromonitroalkyl-N-phenylcarbamates defined above contain.

Such agents are effective against both gram-positive and gram-negative bacteria, even in low concentrations, and can be used over them can also be used successfully as fungicides. However, in order to ensure that even under unfavorable conditions, like very strong dilution of the antimicrobial agent. Influencing the effectiveness the effort goes through other substances, there is always a sufficient antimicrobial effect there. Finding products that have a killing effect even in extremely low concentrations Develop microorganisms. There is another advantage of such particularly powerful products in that there are harmful or unpleasant side effects as a result of the very low level of use Completely prevent or at least largely reduce ίο.

It has now been found that particularly effective antimicrobial agents based on nitroalkyl-N-phenylcarbamates are available obtained when a synergistic combination of 2-bromo-2-nitro-

butyl N-phenyl carbamate and 2-bromo-2-nitrobutyl-N- (3,4-dichloropheuyl) carbamate used in weight ratios from 1: 4 to 4: 1, in particular 1: 1. This synergistic increase in effectiveness is against both bacteria and against

Observe mushrooms, and it will also significantly improve the spectrum of action achieved,

This synergistic increase in the effectiveness of the substances to be combined according to the invention was all the more surprising than previously with combinations of nitro alcohols, their esters with monobasic and polybasic Carboxylic acids and nitroalkyl-N-phenylcarbamates no mutual influence was found.

Can be used in antimicrobial agents the active ingredient combination according to the invention incorporated into liquid, pasty or solid preparations become, such as B. aqueous suspensions. Emulsions. Solutions in organic solvents or oils.

Ointments, creams, pens, powders, soaps, toothpastes, mouthwashes, used as detergents, general and special skin care products and other cosmetic preparations can be used. But also in antimicrobial cleaning agents, disinfectants and preservatives for textiles, floors, hospital facilities and instruments, commercial establishments such as dairies, breweries, and laundries the active ingredient combinations according to the invention can be used with advantage. The salary of the antimicrobial agent in the active ingredient combination according to the invention is 0.05-5 percent by weight, preferably 0.1-1 percent by weight.

Due to their very good antimicrobial effectiveness and the improved spectrum of activity the combination according to the invention is also particularly suitable for the preservation of textile, Leather, paper auxiliaries, adhesives, paints, drilling oils and all kinds of cosmetic Preparations. For this purpose, a use of 0.005 to 0.02 percent by weight is recommended, primarily from 0.01 percent by weight.

In preparations in which the addition of complexing agents is appropriate. the combination according to the invention can also be combined with complexing agents which, in the Hampshire test, have a calcium carbonate binding capacity greater than 230 mg per g complexing agent. This enables a further increase in effectiveness.
The subject of the present application is explained in more detail by the following examples.

The inhibitory concentrations of the 2 - bromine - 2 - nitrobutyl -N-phenylcarbamate to be combined and 2 - bromine - 2 - nitrobuty! - N - (3,4 - dichlorophenyl) - carb-

amats as well as the synergistic combinations of these compositions below are some

Products were indicated with the help of the so-called plate antimicrobial agent.

testes determined. This test is a variant

Embodiment of the guidelines for the antimicrobial solution

Testing of chemical disinfectants of the Germans 5 parts by weight

Society for Hygiene and Microbiology under 2-Bromo-2-nitrobuty] -N-phenylcarbamate 1

the methods for preliminary testing of such agents include 2-bromo-2-nitrobutyl-N- (3,4-dichloro-

written dilution test to determine the phenyl) carbamate 1

microbiostatic effect and can be with alcohol dil., ad 50

Advantage in various tests instead of the _{l0 there}

specified use of liquid nutrient media - Antimicrobial ointments

set. The advantage of solid nutrient media lies in particular in parts by weight

when testing the effectiveness. Substances 2-bromo-2-nitrobutyl-N-phenyI-

as opposed to mushrooms clearly on the Hind. carbamate 0.5

The desired test concentrations were 15 2-bromo-2-nitrobutyl-N- (3,4-dichloro-

by mixing measured amounts of the sub-phenyl) carbamate 0.5

Punch solutions of suitable concentrations with ab- Vaseline alba, ad 100

measured amounts of liquefied bouillon or 2-bromo-2-nitrobutyl-N-phenyI-

Beer wort agars made in sterile petri dishes. carbamate 0.5

The pipetted amounts of the substance solutions 20 2-bromo-2-nitrobutyl-N- (3.4-dichloro-

were 0.1 to a maximum of 1 ml, the total volume of phenyl) carbamate was 0.5

in the Petri dishes after mixing with the oleic acid decyl ester 15

Nutrient medium 10 ml. After the nutrient-colloidal mixture of 90 pieces of soil had solidified, the surface was inoculated with the test cimic suspension C ₁₆ -C ₁₈ alcohol and 10 parts of nasion in broth or wort, which contained 25 trium-C _lf , per ml. -C ₁₈ -arkoho! Sulfate 26

contained approx. 10 "germs. Incubation took place with water 58

37 C or 30 ° C in the incubator and lasted 8 days. _A , · -. , ■ " _no _

Then it was left in the nutritional antimicrobial cream

substance concentration incorporated into the ground the weight> iaie

The growth of the germs is just below the limit. 30 Mineral oil 45.9

could bind. This value determined in this way was called beeswax 5

Denotes inhibitory concentration. The investigations Walrat ^fi

were given in the following concentration intervals by cetyl alcohol 1

led: lanolin 1

250, 200, 150, 100, 75, 50, 40, 30, 25, 20, 15, 10, 5, 2.5, 35 water 40

1,0,5.0,25,0.1 ppm. Perfume 0.1

In this plate test, the 2-bromo-2-nitrobutyl-N-phenyl-

Table listed inhibitory concentrations for the carbamate 0.5

individual active ingredients as well as their combinations 2-bromo-2-nitrobutyl-N- (3,4-dichloro-

determined. 40 pher> .yl) carbamate 0.5

Antimicrobial powder

Substance A: 2-bromo-nitrobutyl-N-phenyl parts by weight

ο S ^a i> ^bama , ·. ν. 1 χι 7 λ α- ui 2-bromo-2-nitrobutyl-N-phenyl-

Substance B: I-Bro ^ iitrobutyl-N ^ / Wichlur _carbamate 0.5

phenyl carbamate. 2-bromo-2-nitrobutyl-N- (3.4-dichloro-

phenyl) carbamate 0.5

Inhibition-inhibition-inhibition ratio test germ Talcum enet., Ad 100

Concentration Concentration Concentration A: B Antimicrobial tooth powder

traiion tration A + B 50

Subst. A Subst. B in ppm parts by weight

in ppm in ppm Precipitated calcium carbonate 94.7

Powdered soap 5

100 25 20 + 5 4: 1 staphylo- 2-bromo-2-nitrobutyl-N-phenyl-

10 + 10 1: 1 coccus 55 a'rbamat 0.15

aurcus 2-bromo-2-nitro-butyl-N- (3,4-dichloi-

phenyM carbamate 0.15

100 KK) 15 + 60 1: 4 Hscherichia Disinfecting H.mdwaschpaste

40 + 20 2: 1 coli _6o c-cwichiMeilc

25 + 25 1: 1 sodium lauryl sulfate 4?

Coconut fatty acid monoethanolamide .... 3

, - ",,.,. · "Pumice stone, finely ground 4S

^{25 50 S + 5 1: 1} Aspergillus nitrilotriacetic acid, sodium salt 2

^less 65 2-bromo-2-nitrobuty] -N-phenyl-

25 50 10 + 10 1: 1 Pcnicilli- carbamate 1

um-came- 2-bromo-2-nitrobutyl-N (3,4-dichloro-

runense phenyl carbamate 1

16 42

5
Antimicrobial abrasive

ücwichlstcilc

Dodecylbenzenesulfonate (WAS 30%) .. 22

Sodium sulfate 2 5

Pumice stone, finely ground 7

Quartz flour, finely ground 66

Nitrilotriacetic acid 2

2-bromo-2-nitrobutyl-N-pheny) -

carbamate 0.5 10

2-Bromo-2-nitrobutyl-N- (3,4-dichlorophenyl) -ca; rbamate 0.5

Antimicrobial detergent

dewichlstcile

Dodecylbenzenesulfonate 24

Sodium tripolyphosphate 44

Sodium Sulphate 14.5

Water glass 6.5 20

2-bromo-2-nitrobutyl-N-phenyl-

carbamate 0.5

2-bromo-2-nitrobutyl-N- (3,4-dichloro-

phenyl) carbamate 0.5

Water 10; ₅

Antiseptic shampoo

(most important! e

Sodium lauryl ether sulfate (27 28%

WHAT) 42

Coconut fatty acid diethanolamide 5

Ethylenediaminetetraacetic acid 0.4

2-bromo-2-nitrobutyl-N-phenyl-

carbamate 0.5

2-bromo-2-nitrobutyl-N- (3.4-dichloro-

phenyl) carbamate 0.5

Fragrances 0.1

Water 51.5

In the following recipes, the added one is used Active ingredient combination according to the invention for the preservation of the products sieeen bacterial and Fungal attack.

Day cream and lotion

C i '-' lAldlMClIc

2-bromo-2-nitrobutyl-N-phenyl-

carbamate 0.005 so

2-bromo-2-nitrobutyl-N- (3,4-dichloro-

phenyl) carbamal 0.005

oleic acid cccyl ester 10

Vegetable oil 10

Glycerin 28 Bc 4 ^ s

Colloidal mixture of 90 T. C ₁₁₁ -C ₁ H-AlkOhOl and 10T. Sodium-

lauryl sulfate 15

Water W)

?

shampoo

Weight parts

2-bromo-2-nitrobutyl-N-phenyl-

carbamate C \ (X) 5

2-bromo-2-nitrobuiyl-N- (3,4-dichloro-

phenylj-carbamate 0.005

Sodium lauryl ether sulfate (27 - 28%

WHAT) 40

Coconut fatty acid diethanolamide 6

Water 54

Emulsion shampoo

Parts by weight

"'-Bromo-2-nitrobutyl-N-phenyl-

carbamate '0.W5

2-bromo-2-nitrobutyl-N- (3,4-dichloro-

phenyU-carbamate 0.005

Sodium Lauryl Sulphate (90% WAS) ... 10

Coconut fatty acid diethanolamide 3

Ethylene glycol stearate 2

Sodium chloride 1

Water S3

Shampoo with egg yolk

<iettichlslcile

2-bromo-2-nitrobutyl-N-phenyl-

carbamate 0.01

2-bromo-2-nitrobutyl-N- (3,4-dichloro-

phcnyl) carbamate 0.01

Cp-Cüj fatty alcohol sulfate mixture

(40., WHAT) 44

Egg yolk liquid technical Γ

Sodium chloride 0.3

Water 52. "

foam bath

<i.'WK-hlsleile

2-bromo-2-nitrobutyl-N-phenyl-

carbamate 0.005

2-bromo-2-nitrobuty] -N- (3,4-dichloro-

phenylj-carbamate 0.005

Sodium Lauryl Ether Sulphate (27 28 "π

WHAT) W

Coconut fatty acid diethanolamide 5

Water 25

The advantage that can be achieved with the agents according to the invention is that, due to the strong Effectiveness of their active ingredient combination and the wide range of active ingredients already in very low Concentrations provide reliable protection against both gram-positive and gram-negative bacteria and ensure against fungal attack. This is of particular importance in all those cases when due to higher concentrations the disinfecting substance can cause harmful or unpleasant side effects can how this z. B. happen with body detergents and other cosmetic preparations can.

Claims (1)

6 42 062 2) Claims before: 1. Bromine-based antimicrobial agents nitroalkyl-N-phenykarbamaten of the formula NO ₂ NH-C-O-CH-C-Br II I! O RB