Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
  • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
  • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring

Definitions

• the present invention relates to a new class of biologically active compounds.
• an anilide contains a naphthyloxy substituent said anilide is a surprisingly effective biocidal agent.
• presence of the weighty naphthyloxy group instead of the comparatively light phenoxy group gives comparable biocidal activity and in some instances more favourable activity.
• said anilide is selected from the class of salicylanilides and carbanilides. It has been found that such naphthyloxy-substituted anilides show surprising germicidal activity. Also, they can be used advantageously in conjunction with detergents.
• the scope of the invention includes a naphthyloxy-substituted anilide in which said anilide is selected from the class consisting of salicylanilides and carbanilides.
• said naphthyloxy-substituent is in the aromatic ring of an aniline group in said anilide, particularly in the 2, Le. ortho, position of said aromatic ring.
• Particularly preferred compounds of the invention are naphthyloxy-substituted anilides in which said anilide is selected from the class consisting of halogen-substituted salicylanilides and carbanilides. Other substituents can be present.
• the halogen is chlorine or bromine and preferably the anilide contains from 1 to 3 halogen atoms.
• An aspect of the invention is a germicidal composition containing a naphthyloxy-substituted anilide according to the invention.
• a preferred aspect of the invention is a germicidal detergent composition containing a naphthyloxy-substituted anilide according to the invention.
• the detergent composition can be in any convenient form such as liquid, paste or hard-surface cleaner but preferably should be in the form of a toilet bar. Suitable formulations for germicidal detergent compositions are given in standard textbooks, for example in Schwartz and Perry, Surface -Active Agents.
• a naphthyloxy-substituted anilide according to the invention can be used in conjunction with other germicides, such as 3,4,4'-trichlorocarbanilide, 3,4,4'-tribromosalicylanilide, 2,2-dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane and 4,2,4'-trichloro-Z-hydroxy-diphenylether.
• germicides such as 3,4,4'-trichlorocarbanilide, 3,4,4'-tribromosalicylanilide, 2,2-dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane and 4,2,4'-trichloro-Z-hydroxy-diphenylether.
• a further aspect of the invention is a pharmaceutical or veterinary composition containing a naphthyloxy-substituted anilide according to the invention together with a pharmaceutically acceptable or veterinarily acceptable carrier.
• the anilides according to the invention can be prepared by a variety of methods.
• one method is the condensation of a naphthylamino-phenylether with a salicyclic acid, the ether and the salicylic acid being prepared by standard methods. A salicylanilide is thereby obtained.
• a halogenated salicylanilide according to the invention is required, a halogenated naphthylamino-phenylether and/or a halogenated salicylic acid can be used.
• An alternative method is the direct halogenation of a naphthyloxy salicylanilide.
• Another example of a method of preparing an anilide according to the invention is by reaction of a naphthylamino-phenylether with an aryl isocyanate, the ether and the isocyanate being prepared by standard methods. A carbanilide is thereby obtained.
• halogenated compounds can be made by appropriate condensation or by halogenation of a naphthyloxy carbanilide.
• EXAMPLE 2 2'-fi-naphthyloxysalicylanilide 1.0 gms. of 2-aminophenyl-jS-naphthylether, 0.58 gm. (0.0042 mole) of salicylic acid and 0.25 ml. of phosphorus trichloride in 20 mls. of chlorobenzene were refluxed for three hours.
• Working up the reaction product as described in Example 1 gave 0.5 gm. (32%) of 2'19- naphthyloxysalicylanilide, M.P. 1l8-120 C. from an alcohol-water mixture.
• EXAMPLE 6 3 ,5 ,3 -trichloro-2'-fl-naphthyloxysalicylanilide A solution of 1.5 gms. (0.005 mole) of 4-chloro-2- amino-,S-naphthylether, 1.03 gms. (0.005 mole) 3,5-di- *Minimum Inhibitory Concentration against Staph. aureus in parts per million.
• EXAMPLE 7 -chloro-2'-a-naphthyloxysalicylanilide A solution of 2.0 gms. (0.0084 mole) of Z-aminophenyl-a-naphthylether 1.45 gms. (0.0084 mole) of 5- chlorosalicylic acid and 0.5 ml. of phosphorus trichloride in mls. of chlorobenzene was refluxed for three hours. Working up the reaction product as described in Example 5 gave 0.85 gm. (25.6%) of 5-chloro-2'-a-naphthyloxysalicylanilide, M.P. 184-6 C. from an alcohol-water mixture.
• EXAM PLE 8 3,4-dichloro-2'-,8-naphthyloxycarbanilide
• 2 gms. (0.0084 mole) of 2- aminophenyl-a-naphthylether in 20 mls. chloroform was added 1.58 gms. (0.0084 mole) of 3,4-dichlorophenylisocyanate, and the mixture stirred for 3 /2 hours.
• the chloroform was removed under reduced pressure, and the crude product washed twice with 60-80 petroleum ether. Recrystallisation of this solid from an alcohol-water mixture gave 1.948 gms. (54.4%) of 3,4-dichloro-2-u-naphthyloxy-carbanilide, M.P. 18l-3 C.
• MIC l-2 By way of comparison, the MIC of salicylanilide is 50.
• a naphthyloxy-substituted salicylanilide selected from the group consisting of 2-(alphaenaphthyloxy)-.salicylanilides and 2'-(beta naphthyloxy) salicylanilides and wherein from 0 to 3 of the 3, 4, 5, 6, 3, 4, 5' and 6 positions of the salicylanilide may have attached thereto a chlorine atom instead of a hydrogen atom.
• a naphthyloxy-substituted salicylanilide according to claim 1 which is 2'-(alpha-naphthyloxy)-salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 1 which is 2'-(beta-naphthyloxy)-salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 1 which is substituted with 1 to 3 chlorine atoms.
• a naphthyloxy-substituted salicylanilide according to claim 4 which is 5-chloro-2'-(beta-naphthyloxy)-salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-dichloro-2'-(alpha naphthyloxy)- salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-dichloro-2'-('beta-naphthyloxy)-salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 4 which is 3,5-3-trichl0ro-2'-(beta naphthyloxy)- salicylanilide.
• a naphthyloxy-substituted salicylanilide according to claim 4 which is 5-chloro-2-(alpha-naphthyloxy)-salicylanilide.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1968
  • 1968-12-03 GB GB5742968A patent/GB1226438A/en not_active Expired
• 1969
  • 1969-12-03 US US881869A patent/US3706799A/en not_active Expired - Lifetime

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