DE1249457B - Use of alkyl dl guamdm salts as mii-robicides - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY GERMAN 4nSv PATENT OFFICE

3

EDITORIAL

Int. CL:

German class: 3Oj

Number: 1249457

File number: F 47056IV a / 30 i

Filing date: September 1, 1965

Opened on: September 7, 1967

AOtN h 7 /

It is already known that alkyl monoguanidines have a good bactericidal and fungicidal effect. Especially because of the unsatisfactory solubility in water and poor compatibility Their use is limited with hard or saline water. This is especially true regarding their use as a bactericide to suppress Desulfovibrio infections in the Secondary production of crude oil.

To the solubility of the alkyl-mono-guanidines and their stability in saline or hard To improve water, it has been proposed to use quaternary ammonium compounds or phosphonium compounds or to combine with fatty alkyl diamine salts.

US Pat. No. 2,336,605 also discloses the microbicidal effect of polymeric guanidines, which contain at least 4 guanidine groups in the molecule are known.

It has now been found that salts of alkyl di guanidines of the general formula

H ₈ NCN- (CH ₈ ) ^ - NC-NH ₂ (I)

NH

NH

in which R is an alkyl radical of 8 to 18 carbon atoms * and m is a number from 2 to 6, excellent MTcrobicides which on the one hand do not have the disadvantages of alkyl monoguanidine salts and on the other hand those known from US Pat. No. 2,336,605 polymeric guanidines are superior in their effectiveness.

The alkyl di-guanidines used according to the invention can be according to methods known per se, for. B. by reaction of diamines of the formula

R __ NH - (CH ₂ ) _m -

in which R and m have the meaning given above, produce with cyanamide or S-alkyl-isothiourea.

Both mono- and polyvalent inorganic or organic acids are used for salt formation Consideration. The choice of acid depends on the solubility properties required. So are suitable for aqueous systems especially sulfuric acid, nitric acid, phosphoric acid, formic acid and preferably Hydrochloric acid and acetic acid. The solubility in organic solvents, such as. B. perchlorethylene, is particularly good when using alkyl di-guanidine salts as organic salts Microbicides

Applicant:

Farbwerke Hoechst Aktiengesellschaft formerly Master Lucius & Brüning, Frankfurt / M.

Named as inventor:

Dr. Karl H. Wallhäußer, Hbfheim (Taunus); Dr. Helmut Diery, Frankfurt / M.-Höchst;

Dr. Max Grossmann, Frankfurt / M. ; - ·

Acids, such as acetic acid, and especially higher acids aliphatic carboxylic acids, such as lauric acid, stearic acid, oleic acid and the like, or mixtures thereof are used will.

The microbicides used according to the present invention are distinguished by a broad spectrum of antimicrobial effects. The fact that some compounds of this class are also soluble in organic solvents and with one the low water content of these solvents suppress fungal and bacterial growth. The effect of the compounds is therefore bound to the presence of certain small amounts of water. In the Representatives of the class of compounds which are soluble in organic solvents are particularly suitable as microbicides Additives for disinfecting dry cleaning as well as for the preservation of dyes and pastes or dispersions. One can use the alkyl di-guanidines also use in emulsion form, both anion-active and cation-active emulsifiers, preferably but nonionic compounds come into consideration.

Even if the effect depends on the solubility of the compounds in water and on the Amine component is influenced, it can be stated that optimal results in general can then be achieved when the alkyl radical R has 10 to 14 carbon atoms, preferably 12 to 14 carbon atoms.

Instead of uniform individuals, mixtures of the compounds mentioned can also be used, if appropriate can also be used together with other microbicides. The effectiveness of the compounds the list below shows what

709 640/493

Claims (1)

3 4 the quantities to be used can be dripped from case to case. After all, you give so much vinegar. In general, acidic, for example, that a sample after dilution with in dry cleaning, up to 1%. based on water has a pH value of 6 to 7,
the liquor volume, use, while in the place of the 97 ° / _o by weight cyanamide can also be used in the petroleum sector up to 50 ppm, customarily 5 90 g of a 5O ° / o aqueous cyanamide einweise 10 to 25 ppm, come into consideration . set and comes to the same reaction Microbicidal spectrum of activity for R = coconut fat product. alkyl, X - CH ₃ COO, η = 1, m - 3. After distilling off the solvent under Data in y / ml for a time of exposure to gentle conditions in a vacuum are obtained 24 hours. io brownish yellow, at 20 ⁰ C not flowing oil, the _,, ",. mixes with water in any proportion. Staph. aureus 1 to 3 »« »- 14860 · /} -101 Streptococcus haemolyt 0.5 to 1 ⁿ S ^ ^{i> 450} "' ^V * ° ~ ^{1> ü1} · Escherichiacoli 3 to 6, ..- t, "" ^. Pseudomonas aeruginosa 6 to 12 _{i &} , ^, ν Claim: Proteus vulgaris 6 to 12 .. _{! V} ^ _{ndung of saizen of} alkyl-di-guanidines Desulfovibno desulfuncans .... 1 to 6 of the general formula Asp. Niger 40 to 80 Asp. Oryzae 40 to 80 R H Penic. notatum 40 to 80 _M | | Example H ₂ NCN- (CH ₂ ) ^ - NC-NH ₂ (I) In a mixture of 80 g NH NH heated to 45 ° C
i-butanol and 135 g N-coconut fatty alkyl propylenedi- amine- (l, 3) is left with stirring at 45 to 50 ⁰ C as microbicides, where R is an alkyl radical from 8 to 43.5 g of acetic acid (100 ° / ₀ ) run in and then carries 45 g of 18 carbon atoms and m a number from 2 to 6 97% cyanamide mean within about 30 minutes. with a corresponding simultaneous increase in temperature to 80 ⁰ C a. In the course of other publications considered:
The mixture is then ^{heated to 100 °} C. for 30 minutes and 30 US Pat. Nos. 2,325,586, 2,336,605;
100 to 105 ^° C., the reaction mixture is stirred for a further 2 hours, Journal of Medicinal Chemistry, Vol. 6 (1963), 16.5 g of glacial acetic acid being slowly added. 709 640/493 8.67 ® Bundesdnickerel Berlin