Claims
- 1. A compound of the formula: ##STR14## wherein: R.sup.1 and R.sup.2 are independently 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 oxygen and Y is sulfur.
- 4. A compound of claim 1 wherein X is sulfur and Y is oxygen.
- 5. A compound of claim 1 wherein X and Y are sulfur.
- 6. A compound of claim 1 wherein R.sup.1 and R.sup.2 are independently halo substituted benzyl or halo substituted phenyl.
- 7. A compound of claim 6 wherein R.sup.1 and R.sup.2 are independently chloro substituted benzyl or chloro substituted phenyl.
- 8. A compound of claim 7 wherein the chloro substitution in R.sup.1 and R.sup.2 is 4-chloro, 2,4-dichloro or 3,4-dichloro.
- 9. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 10. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 11. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(2",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 12. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(2",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 13. The compound of claim 8 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(4"-chlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 14. The compound of claim 8 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(3",4"-dichlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 15. The compound of claim 8 which is 1-[3'-(2",4"-dichlorophenoxy)-2'-(2",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 16. The compound of claim 8 which is 1-[2'-(4"-chlorobenzylthio)-3'-(2",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 17. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzylthio)-3'-(2",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 18. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzylthio)-3'-(2", 4"-dichlorophenoxy)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 19. The compound of claim 8 which is 1-[3'-(3",4"-dichlorophenoxy)-2'-(4"-chlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 20. The compound of claim 8 which is 1-[3'-(3",4"-dichlorophenoxy)-2'-(3",4"-dichlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 21. The compound of claim 8 which is 1-[3'-(3",4"-dichlorophenoxy)-2'-(2",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 22. The compound of claim 8 which is 1-[2'-(4"-chlorobenzylthio)-3'-(3",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 23. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzylthio)-3'-(3",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 24. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzylthio)-3'-(3",4"-dichlorophenoxy)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 25. The compound of claim 8 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(2",4"-dichlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 26. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(2",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 27. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(2",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 28. The compound of claim 8 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(3",4"-dichlorophenylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 29. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 30. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(3",4"-dichlorophenylthio)-propyl]imidazole and the antimicrobial acid addition salts thereof.
- 31. The compound of claim 8 which is 1-[2'-(4"-chlorobenzyloxy)-3'-(4"-chlorobenzylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 32. The compound of claim 8 which is 1-[2'-(3",4"-dichlorobenzyloxy)-3'-(4"-chlorobenzylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 33. The compound of claim 8 which is 1-[2'-(2",4"-dichlorobenzyloxy)-3'-(4"-chlorobenzylthio)propyl]-imidazole and the antimicrobial acid addition salts thereof.
- 34. The compound of claim 8 which is 1-[2',3'-bis(4"-chlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 35. The compound of claim 8 which is 1-[2',3'-bis(2",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 36. The compound of claim 8 which is 1-[2',3'-bis(3",4"-dichlorophenylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 37. The compound of claim 8 which is 1-[2',3'-bis(4"-chlorobenzylthio)propyl]imidazole and the antimicrobial acid addition salts thereof.
- 38. A composition useful for inhibiting the growth of fungi, bacteria or protozoa which comprises an effective amount of a compound of the formula ##STR15## ##STR16## wherein: R.sup.1 and R.sup.2 are independently benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents 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.
- 39. A composition of claim 38 for pharmaceutical use wherein the carrier is a pharmaceutically acceptable, non-toxic carrier.
- 40. A composition of claim 39 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.
- 41. 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 ##STR17## wherein: R.sup.1 and R.sup.2 independently 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 and substituted phenyl; or an antimicrobial acid addition salt thereof or a composition containing same as an active ingredient.
- 42. The method of claim 41 wherein the compound of Formula (I) is administered topically.
- 43. The method of claim 41 wherein the compound of Formula (I) is administered orally or parenterally.
RELATED APPLICATIONS
This case is a continuation-in-part of U.S. Ser. No. 599,743, 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 |
599743 |
Jul 1975 |
|