Claims
- 1. A compound of the formula: ##STR20## wherein: one of R.sup.1 and R.sup.2 is alkyl having 1 to 12 carbon atoms or the group ##STR21## in which n is 0 to 3, and the other of R.sup.1 and R.sup.2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl;
- X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof.
- 2. A compound of claim 1 wherein X and Y are oxygen.
- 3. A compound of claim 1 wherein X is sulfur and Y is oxygen.
- 4. A compound of claim 1 wherein X is oxygen and Y is sulfur.
- 5. A compound of claim 1 wherein X and Y are sulfur.
- 6. A compound of claim 1 selected from the group consisting of:
- a. those wherein R.sup.1 is halo substituted benzyl or halo substituted phenyl and R.sup.2 is alkyl;
- b. those wherein R.sup.1 is alkyl and R.sup.2 is halo substituted benzyl; or
- c. those wherein R.sup.1 is alkyl, R.sup.2 is halo substituted phenyl and Y is sulfur.
- 7. A compound of claim 6 wherein halo substituted benzyl or halo substituted phenyl group is 4-, 2,4-di- or 3,4-dichloro substituted benzyl or 4-, 2,4-di- or 3,4-dichloro substituted phenyl and the alkyl group is a straight chain alkyl having 3 to 8 carbon atoms.
- 8. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 9. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-hexylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 10. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-heptylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 11. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-hexyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 12. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-heptyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 13. The compound of claim 7 which is 1-[3'-(4"-chlorophenoxy)-2'-(n-octyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 14. The compound of claim 7 which is 1-[2'-(n-butylthio)-3'-(2",4"-dichlorophenoxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 15. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 16. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-hexylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 17. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-pentyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 18. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-hexyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 19. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(n-heptyloxy)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 20. The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-pentylthio)propyl] imidazole and the antimicrobial acid addition salts thereof.
- 21. The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-hexylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 22. The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-hexyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 23. The compound of claim 7 which is 1-[3'-(4"-chlorophenylthio)-2'-(n-heptyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 24. The compound of claim 7 which is 1-[2'-(n-butylthio)-3'-(2",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 25. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 26. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-pentyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 27. The compound of claim 7 which is 1-[3'-(2",4"-dichlorophenylthio)-2'-(n-hexyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 28. The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(4"-chlorobenzyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 29. The compound of claim 7 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 30. The compound of claim 7 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(n-hexylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 31. The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(2",4"-dichlorobenzyloxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 32. The compound of claim 7 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 33. The compound of claim 7 which is 1-[2'-(2",4"-dichlorophenylthio)-3'-(n-propylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 34. The compound of claim 7 which is 1-[3'-(n-butylthio)-2'-(2",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 35. The compound of claim 7 which is 1-[2'( 2",4"-dichlorophenylthio)-3'-(n-pentylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 36. A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR22## wherein: one of R.sup.1 and R.sup.2 is alkyl having 1 to 12 carbon atoms or the group ##STR23## in which n to 0 to 3, and the other of R.sup.1 and R.sup.2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl;
- X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof in admixture with a suitable carrier.
- 37. A composition of claim 36 for pharmaceutical use wherein the carrier is a pharmaceutically acceptable non-toxic carrier.
- 38. A composition of claim 37 for topical administration wherein the compound of Formula (I) is present in an amount ranging between 0.1 and 10.0 weight percent of the composition.
- 39. A method of inhibiting the growth of fungi, bacteria or protozoa which comprises applying to a host object containing or subject to attack by fungi, bacteria or protozoa an effective amount of a compound of the formula ##STR24## wherein: one of R.sup.1 and R.sup.2 is alkyl having 1 to 12 carbon atoms or the group ##STR25## in which n is 0 to 3, and the other of R.sup.1 and R.sup.2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substitutents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl;
- X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
- 40. The method of claim 39 wherein the compound of Formula (I) is administered topically.
- 41. The method of claim 39 wherein the compound of Formula (I) is administered orally or parenternally.
RELATED APPLICATIONS
This case is a continuation-in-part of U.S. Ser. No. 599,612, filed July 28, 1975, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3531494 |
Adolphi et al. |
Sep 1970 |
|
3940415 |
Buchel et al. |
Feb 1976 |
|
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
599612 |
Jul 1975 |
|