Hydantoin derivatives and broad spectrum bactericidal/fungicidal compositions thereof

{
  "publication_number": "US4073924A",
  "country": "US",
  "kind": "A",
  "title": "Hydantoin derivatives and broad spectrum bactericidal/fungicidal compositions thereof",
  "abstract": "Described herein are quaternary ammonium salts of hydantoin having the formula: ##STR1## wherein: WHEN R 1 is -- C n H 2n OH, R 2 is ##STR2## and WHEN R 1 is ##STR3## R 2 is --C n H 2n OH; R 3 and R 4, which may be the same or different, are selected from the group consisting of hydrogen, alkyl of 1 to 6 carbons, phenyl or taken together R 3 and R 4 may be a cycloaliphatic group of 4 or 5 carbon atoms; R 5, r 6 and R 7, which may be the same or different, are selected from the group consisting of benzyl or --C p H 2p+1; X is a physiologically acceptable anion; n is an integer from 1 to 4; and p is an integer from 1 to 24. The salts are useful anti-static agents, and certain possess broad spectrum fungicidal and/or bactericidal activity and, accordingly, compositions having such activity contain as an active ingredient certain quaternary ammonium salts of hydantoin.",
  "claims": [
    "1. A hydantoin derivative having the formula: ##STR18## wherein: when R 1 is --C n H 2n OH, R 2 is ##STR19## and when R 1 is ##STR20## R 2 is --C n H 2n OH; R 3 and R 4, which may be the same or different, are selected from the group consisting of hydrogen, alkyl of 1 to 6 carbons, phenyl or taken together R 3 and R 4 may be a cycloaliphatic group of 4 or 5 carbon atoms; R 5, r 6 and R 7, which may be the same or different, are a group selected from the group consisting of benzyl or --C p H 2p+1; X is a physiologically accepted anion; n is an integer from 1 to 4; and p is an integer from 1 to 24.",
    "2. A compound according to claim 1 wherein R 3 and R 4 are both methyl.",
    "3. A compound according to claim 1 wherein: R 3 and R 4, which may be the same or different, are selected from the group consisting of alkyl of 1 to 6 carbons, phenyl or taken together R 3 and R 4 may be a cycloaliphatic group of 4 or 5 carbon atoms.",
    "4. A compound according to claim 1 wherein R 5 and R 6, which may be the same or different, are lower alkyl of 1 to 6 carbon atoms and R 7 is --C p H 2p+1 wherein p is an integer from 8 to 24.",
    "5. A compound according to claim 4 wherein X is bromine, R 5 and R 6 are methyl and p is from 12 to 18.",
    "6. A compound according to claim 1 having the formula: ##STR21## wherein: R 8 is --C n H 2n OH, Z is a physiologically acceptable anion and n is as defined.",
    "7. A compound according to claim 6 having the formula: ##STR22##",
    "8. A compound according to claim 6 having the formula: ##STR23##",
    "9. A broad spectrum fungicidal and bactericidal compositon containing as an active ingredient a fungicidally and bactericidally effective amount of a compound according to claim 6, and a carrier for the active ingredient comprising an inert solid diluent or an inert liquid diluent.",
    "10. A fungicidal and bactericidal composition according to claim 9 containing from about 0.0025 to about 10.0%, by weight, of the active ingredient.",
    "11. A fungicidal composition according to claim 10 containing from about 0.0025 to about 0.1%, by weight, of the active ingredient.",
    "12. A method of combating undesired bactericidal and fungicidal infestations in cosmetic compositions which comprises incorporating therein a fungicidally and bactericidally effective amount of a compound according to claim 6.",
    "13. A method of protecting skin from bacteria and fungi which comprises applying to the skin a bactericidally and fungicidally effective amount of a compound according to claim 6.",
    "14. A method of combating undesired fungicidal and bactericidal infestation in skin wounds which comprises applying to the locus of the skin wound a fungicidally and bactericidally effective amount of a compound as defined in claim 6."
  ],
  "cpc": [
    "C07D 233/72",
    "Y10S 507/92"
  ],
  "assignees": [
    "GLYCO CHEMICALS INC"
  ],
  "filing_date": "1976-10-04",
  "publication_date": "1978-02-14",
  "grant_date": "1978-02-14",
  "priority_date": "1976-10-04",
  "application_number": "US-72934476-A",
  "family_id": "24930622",
  "citations": [
    "US2591103A",
    "US2886487A",
    "US3641248A",
    "US3681377A",
    "US3716552A",
    "US3835151A",
    "US3843677A",
    "US3892748A"
  ]
}