IL43429A - Quaternary ammonium salts of n-phenyl 2-amino-acetamide processes for their preparation and compositions containing them - Google Patents

Description

Dins MV'san manjni NEW QUATERNARY AMMONIUM SALTS OP N-PHENYL 2-AMINO-ACETAMIDE, PROCESSES FOR THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM.

The present invention relates to quaternary ammonium salts which possess disinfectant propert- I ies, to their preparation, and to the disinfectant compositions for general and therapeutic use containing them. I Quaternary ammonium salts which Carry one or two alkyl radicals containing at least 8 carbon atoms bonded to the nitrogen atom possess disinfectant properties. Amongst these quaternary ammonium salts, lauryldimethylbenzylammonium chloride, or benzallconium chloride, is active against a large number of different kinds of germ. However, this compound is much less active, as a bactericide, against Granwiegative bacteria than against Gram-positive bacteria, which leads to its use only at concentrations sufficiently high to control the most resistant bacteria, in order to avoid simply limiting bacterial growth to the latter. An oxaoplo of such resistant bacteria is Pseudomonas aeruginosa or Bacillus pyocyaneus which is responsible for numerous cases of infection in surgical and medical practice and even of whole working areas, which leads to their closure for disinfection.

The present invention provides novel quaternary ammonium salts of the formula: ' A in which R is straight or branched alkyl of 7 to © jawnovalej3&/ |V «. is-~5Tan~ion of an inorganic or organic acid known to form quaternary ammonium salts.

The symbol R preferably represents n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl , n-hexa-decyl, or 2-ethyl-hexyl, or a radical containing one or more methyl groups in which the total number of carbon atoms is between 7 and 16 and the radical corresponds to the alkyl part of alcohols containing 7 to 16 carbon atoms each produced by the oxo synthesis from petroleum olefines. A preferred class of compounds of the invention consists of the compounds of formula (I) in which R is straight chain alkyl of 8 to 14 carbon atoms.

The nature of the anion ® is immaterial; however, the solubility in water of the compounds of formula (I) varies according to the nature of the anion. Generally, chlorides are more soluble than bromides and methosulphates while iodides and nitrates are insoluble or practically insoluble. Generally, * chlorides are suitable for most uses.

According to the invention, the compounds of formula (I) are prepared by one of the following processes: j 1. When, in the general formulaj(I) , the anion χθ is a halide ion, a 4-fluoro-carbanilinomethane .. I ■ ■ of the formula: i --NH-CO-CH2TX1 (II) is reacted with a compound of the formula: X2 " CH3 (III) in which one of and is a halogen atom and the other is (CH3)R in which R is as defined above.

The reaction is generally carried out in an organic solvent which is inert under the working conditions, such as a ketone, especially acetone or methyl ethyl ketone, or an ether such as butyl ether, and at a temperature of between about 20°C and the reflux temperature of the reaction mixture. It is also possible to work in the absence of a solvent, at a temperature of between 20 and 120°C.

The compounds of formula (II) in which X,j represents a halogen atom can be produced by reacting a halogenoacetyl halide with 4-fluoro-aniline.

The compounds of formula (III) in which X2 represents (CH3)R as defined above can be prepared by one of the following methods: a) By reacting formaldehyde and formic acid with an in which X 3 is the chloride ionj. A e.odium salt dissolved in water, e.g. a bromide, iodide or j nitrate, is generally used. j c ( . ! 3. An alkyl ester of the general formula: R - X (VIII) in which R is as defined above and X is a monovalent radical corresponding to the anion X ®, is reacted with the compound of formula: which can itself be prepared by reacting dimethy- lamine with a compound of formula (II) in which .j represents a halogen atom, -jij The following Examples illustrate the invention. ' j Example 1 anilino-carbonvl- A mixture of 4-fluoro~caTbanl-j^ It is also possible to prepare this compound by reacting chloroacetyl chloride . with 4-flubro-aniline in dichloroethane. Ν,Ν-Dimethylheptylamine, also used as a starting material, can be prepared in the following Way: N-Heptylamine (230 g.) is added slowly, with stirring and cooling, to formic acid (460 g.). A commercial aqueous solution of formaldehyde (580 cc. ) is added, still with stirring, to the solution obtained; the mixture obtained is heated gradually. At about 60°C, carbon dioxide begins to be evolved; the temperature of the reaction mixture is gradually raised to 90 °C and the mixture is kept at A mixture of 4-fluoro-(»rJ3^iXij¾o^chloromethane ! (24.4 g.), N, -dimethyl-(2-ethyl-hexyl)-amine (20.4 g.) and methyl ethyl ketone (50 cc.) is heated under reflux with stirring for 4½ hours. The reaction mixture is cooled to about 20°C and stirred for 14 hours. The precipitate which has appeared is filtered off and dried at 50 C under reduced anilino-carbonyl pressure. (4-Fluoro-^ arbirinilino-methyl )-(2-ethyl-hexyl) -dimethylammonium chloride (38 g.) is thus obtained as a white powder which melts at 140°C.

The starting W,N-dimethyl-(2-ethyl-hexyl)-amine can be prepared in a manner similar to that described in Example 1 for N,N-dimethylheptylamine.

Example 4 ani li noj-c arbony 1 A mixture of 4-fluoro- arbatri-itrn'O-chloromethane (31.25 g.) and N,N-dimethyldecylamine (30.87 g.). is stirred for 1¾ hours. The temperature of the reaction mixture, which is initially about 20°C, rises spontaneously and gradually to 50-55 C and the mixture sets solid at the end of stirring. After ani lino-c arbony 1 grinding the solid, ( 4-f luoro-e¾rfaaaijba.-fte--methyl ) -decyl-dimethylammonium chloride (62 g.) is obtained as a white powder which melts at 50°C.

The starting N,N-dimethyldecylamine can be prepared in a manner similar to that described in fixample 1 for Ν,Ν-dimethylheptylamine.· Example 5 ani lino-c arbonyl A mixture of 4-fluoro-»a#feafti±i-¾e-chloro-methane (19.7 g.), Ν,Ν-dimethyldecyl amine (20,6 g.) and butyl ether (100 cc.) is stirred at a temperature of 45-50°C. After being heated for 1 hour, the mixture becomes oily and after 2 hours a precipitate gradually appears. Heating is maintained for a total of 4 hours and the reaction mixture is then cooled to about 20°C. The precipitate is filtered off, washed twice with hexane (a total of I20.cc.) and then dried first at 40 °C and then at 50°C under reduced pressure. (4-Fluoro-c^rbairt /anilino-carbonyl--/ ( iin^methyl) -decyl-dimethylairaohium chloride I · . . . (37.1 g.) is thus obtained as a white powder which melts i ■ ' ■ " ' at 112°C. The difference in the melting point compared with the product of the 'preceding Example ·.. ' · ' 1 · can be explained by the fact, that: the product has crystallised better.

Example 6 ( I . anilino-carbonyl Ά mixture of 4-fluorc^emibendtirifte-chloromethane (48.2 g.) and Ν,Ν-dimethyllaurylamine (57.5 g.) is heated at 120°C, with stirring, for 9½ hours.

Acetone (500 cc.) is added to the cooled reaction mixture and the mixture is then heated until the solid has dissolved completely. The solution obtained is cooled and the precipitate which has appeared is filtered off and dried at 40°C under anilino-carbonyl reduced pressure. (4-Fluoro-ea*fca*«Ai#-©~methyl) -dodecyl-dimethylammonium chloride (20 g.) is thus obtained as a white powder which melts at 95°C.

The same final product is obtained by working without a solvent and at a temperature of between 20 and 50°C.

The starting N, -dimethyllaurylamine can be prepared in a manner similar to that described in Example 1 for N,N-dimethylheptylamine.

Example 7 anilino-carbony1 A mixture of 4-fluoro-ea¾?baft^-ifte-chloromethane (15.6 g.) and N,N-dimethyltetradecylamine (21.2 g.) is heated at 120°C, with stirring', for 9 hours. The reaction mixture is dissolved in the minimum amount , J of hot acetone: the solution is cooled to about 20°C; the precipitate which has appeared is filtered off and dried at 50°C under reduced pressure. (4- ι Pluoro-o^-5fea«-iriiao-meth l ) -tetradecyl-dimethyl-ammonium chloride (25 g.) is thus obtained as a white powder which melts at 115°C.

Example 8 A eolution of sodium bromide dihydrate (8.7 g.) in water (30 cc. ) is added, over the course of 1 hour, to the solution obtained by heating, at 50-55°C, with stirring, a mixture of (4-fluoro-anilino-carbonyl eaa-feaR-i-l-iHe-methyl ) -decyl-dimethyl-ammonium chloride (5.8 g.) and water (80 cc). After the end of the addition, the reaction mixture is stirred at 50-55 °C for 2 hours and then dichloroethane (60 cc.) is added to it, the stirring being continued and the temperature being maintained at 50-55°C for .15 winutcri. 'The organic. phaoxE is IsbJ -fced washed 4 times with water (a total of 240 cc,), and" then concentrated to dryness under reduced pressure while the temperature is kept below 45°C.

The residue is taken up in hexane (60 cc), the crystals are filtered off, washed with hexane and dried at 50°C under reduced pressure. (4-Fluoro- anilino-carbonyl eetri-*mii--W½-methyl)-decyl-d:une^^ bromide (5.55 g.) is thus obtained as a white powder which melts at 110°C.

Example 9 anilino-carboriyl A mixture of 4-fluoro-earbeAiA-ine—bromomethane (14.8 g. ) , dimethyldecylamine (13.2 g.) and butyl ether (100 cc.) is heated at 45-5C°C, with stirring, for 4 hours. The precipitate which appears after cooling to about 20°C is filtered off, washed twice with hexane (a total of 100 cc), and then dried at 50°C under reduced pressure. (4-Fluoro-anilino-carbonyl o^bai^J^w¾o-methyl)-decyl-dimethylammonium bromide (26 g.) is thus obtained as a white powder which melts at 112°C. anilino-carbonyl The starting 4-fluoro-«wrba i-i-ii¾e-bromomethane can be prepared in the following way: Thionyl chloride (63 g.) is added, with stirring and over the course of about 1 hour, to a mixture of brom-oacetic acid (48.7 g.), dichloroethane (500 cc. ) and a few drops of dimethylformamide, heated to 60°C. The reaction mixture is heated under reflux for 2 hours and then concentrated unde reduced pressure to a residual volume of 100 cc. The Sol- ution thus obtained is added, over the course of 1 hour, to a mixture of 4-fluoro-aniline (33.8 g.), i dichloroethane ( 300 cc . ) and sodium carbonate (36 g.) kept at a temperature below 35°C for the entire duration of the addition. The reaction mixture is then heated under reflux for 2 hours, j and the inorganic salts which have precipitated are then filtered off. The organi^ filtrate is washed 4 times with water (a total of 1 , 600 cc. ) at 70°C, and then cooled to 20°C. The precipitate which has appeared is filtered off and ecrystal-lised from dichloroethane. After filtering off th crystals and drying them at 50°C under reduced anilino-carbonyl pressure, 4-fluoro-e¾^£baftiiiBO-bromomethane (40 g is obtained.

Example 10 A solution of sodium iodide (9.7 g.) in water (30 cc.) is added over the course of 1 hour to the solution obtained by heating, at 50-55°C, a mix- anilino-carbonyl ture of (4-fluoro-e«Hi¾aftaJri»e-methyl)-decyl-dimethylammonium chloride (12 g.) and water (120 cc.) After the end of the addition, the reaction mixture is stirred at 50-55°C for 2 hours and then dichloroethane (100 cc.) is added to it, stirring being continued and the temperature being maintained at 50-55°C for 15 minutes. The organic phase is isolated, washed 3 times with water (a total of 300 cc.) and then concentrated to dryness under reduced pressure while the temperature is! kept below 45°C.

The solid yellow residue is taken j up in hexane (60 cc.) and the crystals are filtered off and dried at 60°C under reduced pressure. (4-Fluoro-ani lino-carbonyl catfbani-i-irfte-methyl ) -decyl-dimethylammonium iodide (12.8 g.) is thus obtained as a yellow powder which melts at 98 °C.

Example 1 A solution of sodium nitrate (4.1 g. ) in water (20 cc.) is added over the course of 1 hour to the solution obtained by heating, at 50-55 °C, a mixture ani lino-carbonyl of ( 4— f luoro-eaa?fea«iiij»e-methyl ) -decyl-dimethylammonium chloride (6 g.) and water (80 cc.) After the end of the addition, the reaction mixture is stirred at 50-55 °C for 2 hours, and then dichloro-ethane (60 cc.) is added to it, stirring being continued and the temperature being maintained at 50-55 °C for 15 minutes. The organic phase is isolated, washed 3 times with water (a total of 180 cc ) , and then concentrated to dryness under reduced' pressure while the temperature is kept below 45°C. The oily residue obtained is triturated with hexane the latter is removed by decanting; the residue is again triturated with hexane and - - 434292 this causes it to solidify almost completely; the hexane is again removed by decanting and the residue is dried under reduced pressure at about 20°C and then at 50°C. (4-Fluoro-anillno-carbony1-methyl)-decyl-dimethyl-ammonium nitrate (6 g. ) is thus obtained.

The compounds of formula (i) possess valuable germicidal properties; in particular, they are active against Gram-negative bacteria and more especially against Pseudomonas aeruginosa. They also possess good fungicidal power and a very low toxicity.

These various properties have been demonstrated in the following way: Acute toxicity.

The acute toxioity of the products of Examples 4[(4-fluoro-an llno-carbon 1-methyli-decyl-dlmethyammonium-chloride], 6 [(4-fluoro-anilino-carbony1-methyl)-dodecyl-dlmethylammonium chloride] and 7 [(4-fluoxO-anilino-carbonyl-methyl)^^ chloride] was compared, in mice, by subcutaneous administration, with that of two known disinfectant quaternary ammonium salts,' namely benzalkonium chloride and oetrlmonium bromide. The jproduots were Injected as a f strength aqueous solution and ,the number of deaths over the course of 7 days was observed. The results obtained were as follows: roduct Maximum Minimum LD-50 dose which dose which is alv/ays is' alvays tolerated fatal of Example 4. 1,000 mg/kg No deaths ^l , 000 mg/kg of Example 6 z/1,000 mg/kg No deaths 1 , 000 mg/kg of Example 7, ^1,000 mg/kg No deaths 71,000 mg/kg Benzalkonium 50 mg/kg 80; mg/kg 65 mg/kg chloride Cetrimonium bromide 100 mg/kg 250 mg/kg 135 mg/kg Local tolerance - ocular instillation: The daily instillation, over a period of 8 days, of a solution containing 1/4,000 of the above products did not cause any irritation.

Local tolerance - cutaneous application; Solutions containing 2/1 , 000 of the above products were applied daily, over a period of 15 days, to the skin of the back, from which the hair had previously been removed, of groups of rats, at the same time brushing (two strokes in one direction and two strokes in the reverse direction) with a nylon brush. The rats thus treated did not show any irritation.

These experiments show that the local tolerance of the products of the invention is as good as for the two reference products.

Bacteriostatic properties; by successive dilution in an agar medium, against 23 species of bacteria, consisting of 8 Gram-positive bacteria: Ij .

Bacillus Subtilis (spores) ATCC 633 Bactillus cereus (spores) ATCC 96^34 Streptococcus faecalis ATCC 9354 | I Sarcine lutea ATCC 9341 , Corynebacterium xerose CIP 5216 Staphylococcus aureus ATCC 6538 P Staphylococcus aureus Ho, 1057 Staphylococcus aureus No. 1006 and 15 Gram-negative bacteria: Salmonella typhi Shigella sonnei Escherichia coli Escherichia coli 111ΒΛ Klebsiella pneumoniae Enterobacter aerogenes Serratia marcescens Proteus rettgeri Providencia Pseudomonas aeruginosa ATCC" 9027 Pseudomonas aeruginosa Haut.

Pseudomonas aeruginosa Pon^ Pseudomonas aeruginosa ou.

Moraxella glucidolytica var." norTliq.

Iloraxella lv/offi var. liq Against the Gram-positive bacteria, the 6 and 7 is less than 10 ¾¾n^ml. Against the Gram-negative bacteria, the products of Examples 4 end 6 have an inhibitory effect at a concentration of I less than 100 n ml and that of Example 7 has an inhibitory effect at a concentration of less than j 100 ug ml in the majority of cases and less than 1,000 Bactericidal properties ; They were investigated more particularly against Pseudomonas aeruginosa (ATCC 9027) because of the proved resistance of this bacterium towards a large number of disinfectants.

Using lcnown bacteriological technique, the G3∑periment is carried out by removing the bacteria from the effect of the bactericides after a particular number of minutes, namely 1,2,5,30 or 60 minutes. The number of surviving germs is determined, as a percentage. The bactericidal activity is considered to be good when not more than 0.01% of surviving germs remain.

After one minute of contact, a dose of 250 uig/ml of the product of Example 4, or a dose of 500 uf/ l of the product of Example 6, leaves less than 0.01% of surviving germs. By comparison the bactericidal doses, (based on 00% pure two product) of t e^ known quaternary ammonium salts (jgiaaiah ' ano/ which are employed especially for; medical use are 1 , 000 Pg/ml and 1 , 500Pg/ml respectively.

Fungicidal power; It is determined, in known manner, by the dilution technique in a Sabouraud medium.

The fungicidal activity of the products was determined on the following two strains: Aspergillus niger: a ubiquitous fungus, and Trichophyton mentagrophytea : a dermatophyte.

The fungicidal doses found were as follows: Aspergillus niger Product of Example 2 1,000 ug/ml Product of Example 3 4,000 μα ml 4,000 μg/ml Product of Example 4 500 g/ml 250 μα/ml Product of Example 7 4,000 ug/ml 4,000 μα/πιΐ These properties of the compounds of the invention make them suitable for use as desinfect-ants for both industrial and medical use.

As desinf ctants for industrial use, they can be employed in domestic hygiene for disinfecting crockery, sanitary equipment and floors, in laundering for disinfecting linen, and particularly hcopital linen and babies' napkins, in the foodstuffs industry for disinfecting containers, utensils and equipment in general, and in the textile industry for preventing attacks by fungi. c For disinfecting linen and treating textiles, it is generally preferred to use the compounds of formula (I) which have a low solubility inwAter, which possess a certain substantiyity with respect to textiles, which ma.:es residualj disinfecting possible.

The disinfectant, bacteriostatic, bactericidal, ■ I fungicidal, and in general terms, germicidal compositions for general use which contain, as the active agent, at least one compound of formula (I) thuo form a further subject of the present invention. These compositions can be solid or liquid. Powders or granules are examples of solid compositions. In these compositions, the active compound of the invention is mixed with one or more compatible inert diluents and optionally v/ith substances other than diluents, for example, wetting agents and detergents compatible with the compounds of formula (I), Compositions of this type are very particularly suitable for disinfecting sanitary equipment. They can also be used, after being dissolved in water, for other uses.

Liquid compositions may be dilute or concentrated solutions or suspensions containing inert diluents and substances other than diluents for example wetting ί gents, detergents or flavouring substances compatible with the compounds of formula (I).. The concentrated liquid compositions can be diluted with water at the time of use, Such liquid compositions are particularly suitable for domestic use, treating textiles and disinfecting floors.

These solid or liquid disinfectant compositions can optionally contain one or more other .disinfectants compatible with the compounds of formula (I) and the diluents and adjuvants.

The following Examples illustrate disinfectant compositions for general use according to the invention.

Example A A powder having the following ;composition is prepared in known manner: anilino-carfcony1 (4-Fluoro-caTrbaTi±±inO-methyl) -decyl-dimethylammonium chloride .'♦■·'· 50 g Ethoxylated nonylphenol ... 75 g Anhydrous sodium carbonate ... 200 g Trisodium phosphate ... 100 g Tetrasodium pyrophosphate ... 575 g The composition obtained can be used directly for disinfecting sanitary equipment.

Example B A pov/der having the following composition · is prepared in lcnown manner: anilino-carbonyl (4-Fluoro-ea-s?banA'-L-ifie-methyl) -decyl-dimethylammonium chloride ..*. 30 g Ethoxylated nonylphenol .. * 50 g c rb nate 450 Sodium bicarbonate ... 470 g This composition can be dissolved in the water at the rate of 50 to 300 g. per 100 litres of water for use as a disinfectant in the milk industry.

Example C A solution having the following composition is prepared in known manner: anilino-carbonyl (4-Fluoro-caTtjaTi±±±no-raethyl) -decyl-dimethylammonium chloride .... 50 g Ethoxylated nonylphenol ... 200 g Distilled water to l,000cc By diluting 1 to 3 cc of thi3 concentrated solution to 1 litre, a solution is obtained which can be used in domestic hygiene, for example disinfecting crockery.

As disinfectants for medical or surgical use, the compounds of formula (I) can be used for disinfecting wounds and burns, in the treatment of infected dermatoses, mycoses and ulcerations, for disinfecting operative^ ®^%n gynaecology for treating vulvo-vaginal affections, in ophthalmology as an antiseptic in eye-washe3, and for rinsing the hands of medical personnel.

The pharmaceutical compositions which can be used in therapy and which contain, as active ingredient, at least one compound of formuia (I), constitute a further subject of the invention.

These compositions can be liquids or creams in which the compounds of formula (I) are dissolved, or dispersed in compatible excipients such as polyglycols or fatty alcohols. These compositions can also contain substances other than the diluents, for example flavouring agents which are compatible with the compounds of formula (I).

These compositions are used for external ■· " .. . application and, depending on the degree of infestation of the patient to be treated, the doctor will decide the appropriate frequency of application.

The following Example illustrates pharmaceutical compositions according to the invention, EXAMPLE' A- P A solution having the following composition is prepared in known manner: * ' . ardlino-carbonyl (4-Fluoro-ea*3»HAAi«e-mdiyl) -decyl- .. dimethylammortiUm chloride ... 0.25 g 70% strength ethyl alcohol to 100 cc This solution may be used for disinfecting small wounds, cuts and burns , and for disinfecting -operative fields.

Claims (14)

1. 43429/2 A quaternary ammonium compound of the formula: in which R is straight or branched alkyl of 7 to 16 carbon atoms and is a monovalent anion.

2. A compound according to claim 1, in which the anion' is the chloride, bromide, iodide or methosulphate ion.

3. A compound according to claim 1 or 2 in which R is n-heptyl, n-octyl, 2-ethyl-hexyl, n-decyl, n-dodecy1, n-tetradecyl, n-hexadeoyl.

4. (4-Fluoro-anilino-carbony1-methyl)-heptyl-dimethyl-ammonium chloride.

5. (4-Fluoro-anilino-carbony1-methyl) -n-oct 1-dimethy1-ammonium chloride.

6. (4-Fluoro-anilino-carbonyl-methyl) - (2-ethyl-hexyl) -dimethylammonium chloride.

7. (4-Fluoro-anilino-carbony1-methyl) -n-decyl-dimethyl-ammonium chloride.

8. (4-Fluoro-anilino-carbony1-methyl) -n-dodecy1-dimethy1-ammonium chloride. 43429/2

9. (4-Fluoro-anilino-carbonyl-methyl) -n-tetradecyl- dimethylammonium chloride.

10. (4-Fluoro-anilino-carbonyl-methyl) -n-decyl-dimethyl-ammonium bromide.

11. (4-Fluoro-anilino-carbonyl-methyl) -n-decyl-dimethyl-ammonium iodide.

12. (4-Fluoro-anilino-carbonyl-raethyl) -n-decyl-dimethyl-ammonium nitrate.

13. A process for the preparation of a compound according to claim 1, for which X is a halide ion, which comprises reacting a 4-fluoro-anilino carbonyl-methane of the formula: with a compound of the formula: in which one of X^ and X2 is a halogen atom and the other is N(CH3)R in which R is defined as in claim 1.

14. A. rocess according to claim 13 in which a 4-fluoro-anilino-carbonyl-methane of the formula: in which X^ is chlorine or bromine, is reacted with a compound of the formula: T RN(CH3)2 chloride ion, which comprises reacting a metal a salt of an acid other than chloride in water with a compound according to Claim 1 in which X is the chloride ion. 17. A process according to claim 16 in which the metal salt is sodium bromide, sodium iodide or sodium nitrate, 18. A process for the preparation of a compound according to claim 1, which comprises reacting an alkyl ester of the formula: R - X in which R is as defined in Claim 1 and X is a monovalent radical corresponding to the anion X ^ defined in Claim 1, with the compound of the formul : 3 19.· A process according to claim! 13 substantially described in any one of Ejamples lj to 7 or 9, 20. A process according to claim, 16 substantially as described in Example 8, 10 or 11. 21. A compound according to claim 1 when prepared by a process claimed in any of claims i 13 to 20, ! 22. A disinfectant composition containing as active ingredient at least one compound according to any of claims 1 to 12 or 21 in oooo iation with a compatible) diluent suitable for uoo in a disin ectant, 23. A pharmaceutical composition containing as active ingredient at least one compound claims 1 to 12 or 21 according to eay ofL in association with a compatible pharmaceutically acceptable diluent, 24. A composition according to claim 22 in which the diluent comprises a surface-active agent, 25. A composition according to claim 22 substantially as described in any of Examples A to C, 26. A composition according to claim 23 A substantially as described in Example Sf*