DE1105876B - Process for the preparation of bactericidal triazines - Google Patents

Description

Process for the preparation of bactericidal triazines The invention relates to a process for the production of new triazines with a bactericidal effect, namely of substituted 1-hydroxy-4,6-diamino-1,2-dihydro-s-triazines or their Salt.

The bactericidal triazines prepared according to the invention correspond to the general formula in which R is an alkyl radical with a straight or branched chain with 7 to 16 carbon atoms or an aralkyl radical of the general formulas X # C, H4 - CH2 - or X - Cl, H, - CH, -, in which X is hydrogen, a methyl radical or Is halogen and R 'is hydrogen or a methyl radical.

According to the invention, N-arylalkyloxydiguanides of the general formula are used for the preparation of the new bactericidal substances in which R has the meaning given above, in the presence of acidic catalysts with carbonyl compounds of the general formula in which R 'also has the meaning given above. At least 1 molar equivalent of acid is used for best results.

The carbonyl compounds can be used without solvents or diluents or in a solvent, for example a lower aliphatic alcohol, be applied.

The substances are usually obtained in the form of their salts and can be treated through treatment be converted to their free base with an alkali hydroxide such as sodium hydroxide.

Compounds with a particularly good bactericidal effect are: 4,6-diamino-1,2-dihydro-2,2-dimethyl-l-n-decyloxy-s-triazine, 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-n-dodecyloxy-s-triazine, 4,6-diamino-1,2-dihydro-2,2-dimethyl-ln-nonyloxy- s-triazine, 4,6-diamino-1,2-dihydro-2,2-dimethyl-1- (1'-naphthylmethoxy) -s-triazine and 4,6-diamino-1,2-dihydro-2,2-dimethyl-1- ( 2'-naphthylmethoxy) -s-triazine and salts of these compounds. As already mentioned, those are suitable according to the invention compounds prepared as bactericidal agents. It was found that she against organisms such as Staphylococcus aureus, Streptococcus pyogenes, Corynebacteria diphtheriae, Escherichia coli, Pseudomonas aeruginosa, Ebethella typhosa and Klebsiella pneumoniae have a high effectiveness when used in vitro, so that they can be used for medical, surgical and veterinary purposes.

The invention is illustrated in the following examples; the parts are parts by weight. Example 1 To a suspension of 103 parts of N-n-decyloxydiguanide in 750 parts of acetone, 52 parts of concentrated hydrochloric acid are added, the Solid goes into solution. The mixture is refluxed for 4 hours and concentrated by distillation. The white solid precipitated on cooling is filtered and dried; Melting point 196 to 197 ° C. When recrystallizing acetone, which contains a small amount of ethyl alcohol, turns into colorless needles of 1-n-decyloxy-4,6-diamino-1,2-dihydro-2,2-dimethyls-triazine monohydrochloride obtained from melting point 198 to 200 ° C. The substance forms a picrate of yellow needles from alcohol; Melting point 193 to 194 ° C. Example 2 A mixture from 20 parts of N-n-dodecyloxydiguanide dihydrochloride, 150 parts of acetone and 50 parts Alcohol is refluxed for 8 hours. After evaporation of the solvents a gum is obtained which solidifies when titrated with acetone. 4,6-diamino-1,2-dihydro 2,2-dimethyl-1-n-dodecyloxy-s-triazine hydrochloride crystallizes from acetone-alcohol in the form of white needles; Melting point 200 ° C.

Example 3 A mixture of '17, 5 parts of N-n-tetradecyloxydiguanide monohydrochloride, 4 parts of concentrated hydrochloric acid and 150 parts of acetone are refluxed for 8 hours cooked. After traces of insoluble substances have been removed, the filtrate is cooled, whereby a white solid precipitates. When recrystallizing from acetone-alcohol, 4,6-diamino-1-, 2-dihydro-2,2-dimethyl-1-n-tetradecyloxy-s-triazine hydrochloride is obtained obtain; Melting point 196 to 197 ° C.

Example 4 A mixture of 51 parts of N-n-decyloxydiguanide, 26 parts concentrated hydrochloric acid, 117 parts of acetaldehyde and 350 parts of alcohol is on Heated reflux condenser for 8 hours. After evaporation of the solvent remains a colorless gum that solidifies when titrated with dry ether-acetone (1: 1). The solid is filtered and recrystallized from acetone-alcohol, being acicular 1-n-decyloxy-4,6-diamino-1,2-dihydro-2-methyl-s-triazine hydrochloride deposited will. Melting point 205-206 ° C. The picrat forms needles-vom Schrrielzpürikt-178 up to 179 ° C.

The further compounds according to the invention listed in Examples 5 to 14 were prepared by analogous processes. manufactured. The . Compounds correspond to the general formula I, v @ obei R and R 'have the values listed in the table: - - Melting point of - Melting point of Example - - -R- R # monohydrochloride picrates - OG ° C 5 n - C7H 1 _ 5 C H3 201 '- 186-187 6 n-C8 1-11 7 CH, 205 to 206 - 7 n - C 9H19 CH, 220 to 222 180 to 181 8th ,- . n - C1sH'33 CH3 187 to 190 9 08H5-- CH2- CH, 219 to 220: 207 to 208 10 1-naphthylmethyl - CH3 215 11 2 = Naphthyhnethyi t, CH $ 231 -to 232-, - - - 12 p-CH3 # CBH4 # CH2 .- @ CH3. 245- __. . _ - 13 p - Cl - CBH4 - CH2 CH3. 243 ---- 14 p-Br.CBH1-CH.2 - CH3 -... '; 225 _

Claims (2)

PATENT4NSPRt1CUE: 1. Process for the preparation of bactericidal triazines of the more general. Formula: - in which R is a straight or branched chain alkyl radical with 7 to 16 carbon atoms or an arylalkyl radical of the general formulas X # C6 H4 - C H2 and X # C1oHs - C-H2, in which X is hydrogen, a methyl radical - or halogen, and_R 'denotes hydrogen or a methyl radical, or salts thereof, characterized in that N arylalkyloxydiguanides of the general formula. in which R has the meaning given above, with carboryl compounds, of the general formula in which R 'has the meaning given above, is reacted in the presence of acidic catalysts. 2. The method according to claim 1, characterized in that at least 1-. Molecular equivalent of acid is used. German patent specification No. 879 696. With the announcement is a test report (2 pages) has been laid out.