Inhibition of bacterial biofilms and microbial growth with imidazole derivatives

Patent metadata

Field	Value
Publication number	US-9815794-B2
Application number	US-201615019025-A
Country	US
Kind code	B2
Filing date	Feb 9, 2016
Priority date	Mar 25, 2011
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

Disclosure is provided for imidazole derivative compounds useful to inhibit the formation of biofilms and/or inhibit microbial growth, compositions including these compounds, devices including these compounds, and methods of using the same.

First claim

That which is claimed is:

1. A compound of Formula (I)(a):

wherein:
R 1a , R 1b and R 2 are each H;
n=3 to 7;
m=0;
R 3 and R 4 are each aryl; and
each occurrence of R w , R x , R y and R z is H,
or a salt thereof.

2. The compound of claim 1 , wherein said compound has microbicidal activity.

3. A composition comprising a carrier and an effective amount of the compound of claim 1 .

4. The composition of claim 3 , wherein said composition is formulated for topical use.

5. The composition of claim 3 , wherein said composition is an ointment, cream, lotion, paste, gel, spray, aerosol, or oil.

6. A composition comprising the compound of claim 1 covalently coupled to a substrate.

7. A biofilm or bacterial growth inhibiting coating composition, comprising:
(a) a film-forming resin;
(b) a solvent that disperses said resin;
(c) an effective amount of the compound of claim 1 , wherein said effective amount of said compound inhibits the growth of a biofilm and/or bacteria thereon; and
(d) optionally, at least one pigment.

8. The compound of claim 1 , wherein R 3 and R 4 are each phenyl.

9. The compound of claim 8 , wherein n=5.

10. A composition comprising a carrier and an effective amount of the compound of claim 9 .

11. A composition comprising the compound of claim 9 covalently coupled to a substrate.

12. A method of controlling biofilm formation or microbial growth on a substrate comprising the step of contacting the compound of claim 1 to said substrate in an amount effective to inhibit biofilm formation or microbial growth.

13. The method of claim 12 , wherein said method comprises the step of clearing a preformed biofilm from said substrate by administering an effective amount of the compound to said substrate, wherein said effective amount will reduce the amount of said biofilm on said substrate.

14. A method for treating a chronic bacterial infection in a subject in need thereof, comprising administering to said subject the compound of claim 1 in an amount effective to inhibit, reduce, or remove a biofilm component of said chronic bacterial infection.

15. The method of claim 14 , wherein said chronic bacterial infection is selected from the group consisting of urinary tract infection, gastritis, respiratory infection, cystitis, pyelonephritis, osteomyelitis, bacteremia, skin infection, rosacea, acne, chronic wound infection, infectious kidney stones, bacterial endocarditis, and sinus infection.

16. A medical device comprising:
(a) a medical device substrate; and
(b) an effective amount of the compound of claim 1 , either coating the substrate, or incorporated into the substrate, wherein said effective amount of said compound inhibits the growth of a biofilm and/or bacteria thereon.

17. A method of preventing, removing or inhibiting microbial biofilm formation or microbial infection in a plant or plant part thereof, comprising applying to said plant or plant part a treatment effective amount of a compound of claim 1 , or an agriculturally acceptable salt thereof.

18. The method of claim 17 , wherein said plant is a fruit crop plant or a vegetable crop plant.

19. The method of claim 17 , wherein said microbial biofilm formation or microbial infection is caused by a fungi.

20. The method of claim 17 , wherein said compound is applied to said plant in an amount effective to treat or control a fungal disease selected from the group consisting of rots, leaf molds, blights, wilts, damping-off, spot, root rot, stem rot, mildew, brown spot, gummosis, melanose, post-bloom fruit drop, scab, alternaria, canker, flyspeck, fruit blotch, dieback, downy mildews, ear rots, anthracnose bunts, smut, rust, eyespot and pecky rice.

21. A method of enhancing the effects of a fungicide, comprising applying the compound of claim 1 in combination with said fungicide.

22. The method of claim 21 , wherein said fungicide comprises copper.

23. The method of claim 21 , wherein said fungicide and said compound are applied simultaneously.

24. The method of claim 21 , wherein said fungicide and said compound are applied sequentially.

25. The method of claim 21 , wherein said applying is carried out on a plant or plant part.

26. A method of controlling biofilm formation or microbial growth on a substrate comprising the step of contacting the compound of claim 9 to said substrate in an amount effective to inhibit biofilm formation or microbial growth.

Assignees

• Univ North Carolina State

Inventors

• Melander Christian
• Mccall W Steve
• Su Zhaoming
• Melander Roberta

Classifications

• A01N59/20

  Copper · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• C07D233/88 Primary

  Nitrogen atoms, e.g. allantoin · CPC title