New adamantane derivative and aqueous disinfectant composition containing it

Abstract: The subject matter of the present invention is the adamantane 5,7-diphenyl-1,3-diazoadamantan-6-one derivative per se and the aqueous disinfectant compositions, characterised in that they contain this molecule, and/or the molecule of at least another adamantane derivative, associated in particular with peracetic acid. The disinfectant compositions according to the invention can be utilised as such or water-diluted at the time of use. The disinfectant compositions according to the invention are sporicidal, bactericidal, fungicidal and virucidal for very short contact times.

Description: The present invention relates to an adamantane derivative, the 5,7-diphenyl-1,3-diazoadamantan-6-one, per se and to the aqueous disinfectant compositions containing, associated in particular with peracetic acid, this molecule, and optionally the molecule of at least another adamantane derivative. Disinfectant compositions containing, among other components, molecules with adamantane residues, are known in the art. However, none of the disinfectant compositions as proposed so far contains the 5,7-diphenyl-1,3-diazoadamantan-6-one molecule, and optionally the molecule of another adamantane derivative, in particular associated to peracetic acid. Therefore, a subject of the present invention is the 5,6-diphenyl-1,3-diazoadamantan-6-one molecule, having the following formula (each atom of the adamantane molecule skeleton is conventionally assigned a number; the numbers of the atoms involved in relevant substitutions are evidenziated in the formula): A further subject of the present invention is the use of the 5,7-diphenyl-1,3-diazoadamantan-6-one molecule, and optionally the molecule of at least another adamantane derivative, for the formulation of disinfectant compositions. Finally, the aqueous solutions of disinfectant compositions, characterised in that they comprise, associated to peracetic acid, the 5,7-diphenyl-1,3-diazoadamantan-6-one molecule, and optionally the molecule of another adamantane derivative, constitute a further subject of the present invention. The disinfectant composition according to the invention comprises, in one embodiment thereof, the following components, expressed as percent w/v: 5,7-diphenyl-1,3-diazoadamantan-6-one 0.005-5 peracetic acid 0.015-15 optionally, phenolic derivatives ≤ 10 optionally, additives ≤ 50 water as volumetrically needed to 100. The phenolic derivatives can be selected from the group comprising o-phenyl-phenol, p-chloro-m-cresol, 2-benzyl-4-chlorophenol, phenol and combinations thereof. The additives can be selected from the group comprising solvents, sequestering agents, anticorrosives, buffers, perfumes and combinations thereof. The formulations according to the present invention can be utilised as such or water-diluted at the time of use. Dilutions depend on the required rate of the biocidal action. The formulations according to the invention proved sporicidal, bactericidal (Gram+ and Gram- Mycobacterium tuberculosis included), fungicidal and virucidal, for very short contact times (starting from 5 minutes). All the microbiological values were tested and are testable according to the CEN TC/216 methods. So far, only a general description of the present invention has been given. With the aid of the examples a more detailed description of some embodiments will be provided hereinafter, finalized to give a better understanding of objects, features, advantages and applications thereof. EXAMPLE 1 5,7-diphenyl-1,3-diazoadamantan-6-one preparation 1.5 moles dibenzylketone, 7.5 moles paraformaldehyde and 3.0 moles ammonium acetate are measured in a roundbottomed flask. The mixture is dispersed in a volume of ethanol (at least 95°), assessed in the approximate ratio 1:1 with respect to the sum of the reagent weights. The reaction vessel closed with a fluxing system is brought to boiling onto a water bath. The reagent solubilisation takes place with the temperature increase. Thereafter, the solution becomes red and a crystalline precipitate begins to form. After a 4-hour boiling the reaction is considered to be completed. The mixture is cooled in a freezer and filtered under vacuum. The raw product is rinsed twice in 95° ethanol, dissolved into a minimum quantity of hot chloroform and filtered. The filtered solution is diluted with an equal volume of 95° ethanol and left overnight in a freezer. The resulting white crystalline compound is collected on a Buckner, rinsed with 95° ethanol and dried. The evidence of the attainment of the compound according to the invention is provided by the empirical formula C 22 H 20 ON 2 , with a molecular weight of 328 and a melting point of 263-264°C. Yield: about 25% of the reagent total. EXAMPLE 2 A disinfectant and sporicidal solution according to the invention has the following composition in percent w/v: 5,7-diphenyl-1,3-diazoadamantan-6-one 0.050 peracetic acid 0.100 p-chloro-m-cresol 0.075 o-phenyl-phenol 0.005 phenol 0.100 additives 15 water as volumetrically needed to 100 EXAMPLE 3 A disinfectant and sporicidal solution according to the invention has the following composition in percent w/v: 5,7-diphenyl-1,3-diazoadamantan-6-one 0.050 peracetic acid 0.100 p-chloro-m-cresol 0.188 additives 15 water as volumetrically needed to 100 EXAMPLE 4 A disinfectant and sporicidal solution according to the invention has the following composition in percent w/v: 5,7-diphenyl-1,3-diazoadamantan-6-one 0.050 peracetic acid 0.150 additives 15 water as volumetrically needed to 100 EXAMPLE 5 The compositions of the examples 2, 3 and 4 were tested to determine the sporicidal, bactericidal, fungicidal and virucidal activities thereof for different contact times according to the methods set by the CEN TC/216 (Comité Européen de Normalisation, Technical Committee) norms. Test results confirmed the expected activities.

Claims: The chemical compound 5,7-diphenyl-1,3-diazo-adamantan-6-one, having the formula: Use of 5,7-diphenyl-1,3-diazo-adamantan-6-one, according to claim 1, for the formulation of disinfectant compositions. Aqueous disinfectant composition, characterised in that it comprises, associated with peracetic acid, 5,7-diphenyl-1,3-diazoadamantan-6-one according to claim 1, and optionally at least another adamantane derivative. Aqueous disinfectant composition according to claim 3, having the following composition expressed in percent w/v: 5,7-diphenyl-1,3-diazoadamantan-6-one 0.005-5 peracetic acid 0.015-15 optionally, phenolic derivatives ≤ 10 optionally, additives ≤ 50 water as volumetrically needed to 100. Disinfectant composition according to claim 4, wherein the phenolic derivatives are selected from the group comprising: o-phenyl-phenol, p-chloro-m-cresol, 2-benzyl-4-chlorophenol, phenol and combinations thereof. Disinfectant composition according to claim 5, wherein the additives are selected from the group comprising solvents, sequestering agents, anticorrosive agents, buffers, perfumes and combinations thereof. Use of the disinfectant compositions according to any one of the claims 3 to 6, water-diluted at the time of use.

Inventors: AFFAITATI PIETRO, FOLCHITTO GIANCARLO, AFFAITATI, PIETRO, FOLCHITTO, GIANCARLO
Applicants: IMS S R L, IMS S.R.L.
Application year: 2000
Main classification: C07D487
IPC codes: C07D487, A01N43