DE2247370C3 - 1,3,3-Trimethyl-1-noctylaminomethyl-5-n-octylamino-cyclohexane, process for their preparation and their use as a microbicidal active ingredient - Google Patents

Description

The invention relates to a new compound 1,3,3-trimethyl-1-n-octylaminomethyl-5-n-octylamino-cyclohexane and a process for the preparation of this compound and its use as a microbicider Active ingredient.

In the context of the present invention, microbicides are understood to mean the killing of gram-positive and gram-negative bacteria, fungi and yeasts. These are the main benefits, but the compounds also have some Effectiveness against viruses and algae.

When using microbicidally active compounds, it is desirable to have a wide range to have various chemical compounds available in order to avoid that the Bacteria to be killed and the like form resistant strains or that strains that have already become resistant can again be fought with success.

The provision of a new class of microbicidally active compounds is thus enriched by state of the art from the outset.

The present invention relates to a new active ingredient, which compared to known active ingredients under other has the particular advantage that R he particularly effective against a number of bacteria, fungi and yeasts, which are relatively difficult are to be combated and are very often blamed for so-called hospitalism. This means the spread of pathogenic germs, especially in hospitals, these germs are characterized by high resistance to microbicidal compounds. Examples of such germs are S. aureus, P. aeruginosa and K. pneumoniae.

This new microbicidal compound is 1,3,3-trimelhyl-l-n-octylaminomethyl-5-n-octylamino-cyclohexane, which can be represented by the following formula:

H ₃ C

-N

H ₃ C

H ₃ C CH ₂ N

The basic structure with two amino groups is also known as isophoronediamine. The underlying diamine has no effect.

The mono-n-octylamine derivative shows only slight microbicides Effect. The molecule has three or four n-octyl groups attached to the nitrogen atom on, the solubility of these compounds in water or aqueous alcohol drops so much that they are practically no longer usable in aqueous preparations. It is therefore of particular interest the di-n-octylamino compound claimed according to the invention.

This connection can then be established. that one 1,3,3-trimethyl -1 - aminomethyl-5-aminocyclohexane Reacts in a manner known per se with approximately equimolar amounts of n-octyl chloride, after the exothermic reaction has ended, for about 1 hour to temperatures of 100 to 150 ° C heated, freed from residue and the desired compound from the reaction mixture, preferably by fractional distillation.

In this implementation with approximately equimolar amounts Octyl chloride results in a mixture of unreacted starting compound, simply octylated Compound and the desired dioctylated compound. The compound of the invention can can be obtained from this mixture by fractional distillation. One would be larger than equimolar Using amounts of n-octyl chloride, based on the starting compound, would also result in proportions higher alkylated product, which are not desired and of the desired compound according to the invention would be difficult to separate.

The 1,3,3-trimethyl-1-n-octylaminomethyl-5-n-octylamino-cyclohexane according to the invention is not soluble in water. Since the application of the compound according to the invention, however, preferably from aqueous or aqueous-alcoholic solution takes place, it is therefore necessary that in the preparation of the a solubilizer is used in the preparation containing this compound. Examples of suitable ones Solubilizers are z. B. the addition products' of ethylene oxide to higher alcohols, such as. B. tridecyl alcohol, or cation-active compounds, such as. B. dodecyldimethylbenzylammonium chloride. Man uses these solubilizing agents in approximately the same amounts, based on the active substance.

The compound according to the invention can be prepared in the usual way, i. h., the solved resp. solubilized compound can be used together with other microbicidal compounds and with further additives, such as odorants or dyes. The compound can also be fluorinated in Chlorinated hydrocarbons are dissolved and are used in aerosol form. By adding the solubilizing agent when using an aqueous solution becomes the cleaning power at the same time

of solutions, especially when nonionic surfactants are used as solubilizing agents be used.

In the following example, the inventive Procedure explained. The effectiveness of the invention is then shown in tabular form connection established. The test for microbicides was carried out according to the guidelines of the German Society for Hygiene and Microbiology e. V., Gustav Fischer Verlag. Stuttgart, 1959. In the tables + means germ growth, - means no germ growth.

example

In a 2-1 four-necked flask equipped with a KPG scrambled egg (= Küppers precision glass stirrer), thermometer, reflux condenser and dropping funnel, 2 mol 1,3,3 - trimethyl -1 - aminomethyl - 5 - aminocyclohexane, 3 2 mol NaOH and 5 ml H ₂ O heated to 10O ⁰ C zo. 2 moles of n-octyl chloride are then added in small portions (2 hours) and the mixture is then heated to about 140 ° C. for 1 hour. The inorganic residue is then decanted while still hot and the decanted liquid is subjected to fractional vacuum distillation. After a pre

cyclohexane and 1,3,3 - trimethyl -1 - η - oclylaminomethyl-5-aminocyclohexane go between 192 and 194 C at 0.5 Torr 340 g of pure 1,3,3-trimethyl-1 - η - octylaminomethyl - 5 - η - octylamino - cyclohexane

Elemental analysis for C ₂₆ H ₅₃ N ₂ (molecular weight 395):

Calculated:
C 79.0, H 13.8, N 7.2 percent by weight;

found:

C 79.2, H 13.2, N 7.1 weight percent.

To test the microbicidal effectiveness, the following preparations were made:

Preparation 1

The pH of the 0.1% active ingredient aqueous solution was adjusted to 7.5 with acetic acid.

Test strain Conc
tration Exposure line in min. I. 2 5 10 20th 30th in % - - - - - - S. aureus 0.1 + + - - - - 0.05 + + + - - - 0.01 + + + + + - 0.005 + + + + + + 0.001 - - - - - - E. coli 0.1 - - - - - - 0.05 + - - - - - 0.01 + + + + + 0.005 + + + + + + 0.001 - - - - - - P. vulgaris 0.1 + + ~ - - - 0.05 + + 4- + + + 0.01 + + + + + + 0.005 + + + + + + 0.001 - - - - - - P. aeruginosa 0.1 - - - - - - 0.05 + + + + + + 0.01 + + + + + + 0.005 + + + + + 0.001.

35 Preparation 2

The pH of the aqueous solution containing 0.1% active substance was adjusted to 5.1 with acetic acid.

Preparation 1

10 parts by weight of 1,3,3-trimethyl-1-n-octylaminomethyl-5-n-octylamino-cyclohexane, 10 parts by weight of an addition product of 12 moles of ethylene oxide and 1 mole of isotridecyl alcohol, 10 parts by weight of acetic acid and 70 parts by weight of water are stirred at 40 ^° C homogenized. A clear solution which can be diluted _{with H 2 O is obtained.}

Preparation 2

10 parts by weight of 1,3,3-trimethyl-1-n-octylaminomethyl-5-n-octylamino-cyclohexane, 10 parts by weight of a solution that is 80%

CH ₃

C ₁₂ H ₂₅ - N ^ -CH ₂ - ^ 3
CH ₃

OO

Cl

and contains 20% ethanol, as well as 10 parts by weight of acetic acid and 70 parts by weight of water are under Stir homogenized at about 40 ° C.

65

Test strain Conc
tration 1 Action rate in min 5 10 20th 30th in % 2 S. aureus 0.1 - - - - - 0.05 - - - - - - 0.01 - - - - - - 0.005 - + + + - 0.001 - + - - - - E. coli 0.1 - - - - - - 0.05 - - - - - - 0.01 + - - - - - 0.005 + - + + + + 0.001 - + - - - - C. albicans 0.1 - - - - - - 0.05 + - - - - - 0.01 + + - - - 0.005 + + + + + - 0.001 + - - - - A. flavus 0.1 + - - - - 0.05 + + + - - - 0.01 + + + + - 0.005 + + + + -f 0.001 +

A mixture of equal parts by weight of hexachlorophen (= 2,2'-methylene-bis- (3,4,6-trichlorophenole and a reaction product of 12 moles of ethyl oxide with tridecyl alcohol used. The stated concentrations relate to the hexachlorophene content. The pH of the aqueous solution is 7.7.

Test lamb Conc
tralion Exposure time in min. 1 2 5 10 20 ' 30th in % + : S. aureus 0.1 + - - - - - 0.05 + + + + + - 0.01 + + + + + + 0.005 + + + + + - E. coli 1.0 + + + + + + 0.5

IO P. expansum Conc
tration 6th Action line in min. 1 5 10 20th 30th Test strain : r. % + - - 2.0 + + + + 4th - 5
P. aeruginosa 1.0 + + + + + 4- 0.5 + + + + 4- 4- 5.0 + + + + 4- " 4- C. albicans 2.5 + + + + 4- 4- 1.0 + + + + 4- 4- 5.0 + + + 4- 4- 2.5 + + + 4- 4- 1.0

A comparison of the tables shows the superiority of the compound according to the invention with respect to theirs microbicidal effectiveness.

Claims (3)

Patent claims: 1. 1,3,3 - trimethyl -1 - η - octylaminomethyl-5-n-octylamino-cyclohexane. 2. A method for producing the compound of claim 1, characterized in that one 1,3,3 - trimethyl -1 - aminomethyl - 5 - aminocyclohexane reacts in a manner known per se with approximately equimolar amounts of octyl chloride, according to The exothermic reaction ends for about 1 hour to temperatures of 100 to 150 ° C heated, freed from residue and the desired compound from the reaction mixture, preferably by fractional distillation. 3. Use of the compound of claim 1 as a microbicidal active ingredient.