Antimicrobial Compounds and Methods of Use

Abstract

Organophosphorus or organosulfur compounds and methods of using the compounds as cleaning agents, particle dispersants, or surfactants, or to remove, disperse or inhibit the growth of a biofilm, or inhibit the growth of, or kill a fungus or bacteria are provided.

1 . A compound of Formula I, or a salt thereof, wherein Formula I is represented by the structure: 
       
         
           
           
               
               
           
         
         where A is C 1-10  hydrocarbyl or optionally R 1  substituted C 1-10  hydrocarbyl; X is —NHR, —NHOR, —NHCOR, —NHOCOR, or —OR; and R is H or C 1-10  hydrocarbyl; 
         R 1  is selected from hydrogen, halogen, cyano, OH, C 1-6  hydrocarbyl, C 1-6  alkoxy, SOR 2 , SO 2 R 2 , SO 2 NR 3 R 4  COR 2 , CO 2 R 2 , CONR 3 R 4 , NR 3 R 4 , NR 3 COR 4 , NR 3 SO 2 R 4 , NR 3 CO 2 R 4 , NR 3 CONR 4 , OCOR 2 , and phosphonic acid, wherein each of C 1-6  hydrocarbyl, C 1-6  alkoxy, SOR 2 , SO 2 R 2 , SO 2 NR 3 R 4 , COR 2 , CO 2 R 2 , CONR 3 R 4 , NR 3 R 4 , NR 3 COR 4 , NR 3 SO 2 R 4 , NR 3 CO 2 R 4 , NR 3 CONR 4 , OCOR 2 , can be optionally substituted with halo, amino, hydroxyl, C 1-6  hydrocarbyl, C 1-6  alkoxy, cyano, or phosphonic acid; 
         R 2 , R 3  and R 4  are independently selected from hydrogen, C 1-6  hydrocarbyl, in which each of the C 1-6  hydrocarbyl can be optionally substituted with halo, amino, hydroxyl, C 1-6  alkoxy, cyano, or phosphonic acid. 
       
     
     
         2 .- 8 . (canceled) 
     
     
         9 . The compound of Formula I of  claim 1 , wherein A is C 3-5  alkyl, R′ is CH 3 , and X is OH. 
     
     
         10 . The compound of Formula I of  claim 9 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         11 .- 16 . (canceled) 
     
     
         17 . A compound of Formula II, or a salt thereof, wherein Formula II is represented by the structure: 
       
         
           
           
               
               
           
         
         where A is R, Y is O or S, X is NH 2 , OH, or OR, and G is R, where R is C 1-10  hydrocarbyl. 
       
     
     
         18 . The compound of Formula II of  claim 17 , wherein X is NH 2 . 
     
     
         19 . The compound of Formula II of  claim 18 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The compound of Formula II of  claim 17 , wherein X is OH. 
     
     
         21 . The compound of Formula II of  claim 20 , wherein the compound is: 
       
         
           
           
               
               
           
         
       
     
     
         22 . A compound of Formula III, or a salt thereof, wherein Formula III is represented by the structure: 
       
         
           
           
               
               
           
         
       
     
     
         23 . A composition comprising the compound of  claim 1 . 
     
     
         24 . A composition comprising the compound of  claim 17 . 
     
     
         25 . A composition comprising the compound of  claim 22 . 
     
     
         26 .- 27 . (canceled) 
     
     
         28 . A method of dispersing or inhibiting the growth of a biofilm, or inhibiting the growth of, or killing a fungus or bacteria, comprising contacting the biofilm, fungus or bacteria with an amount of a compound of Formula II of  claim 17 , or a composition comprising an amount of a compound of Formula II, wherein the amount of the compound of Formula II is effective to disperse or inhibit the growth of the biofilm, or inhibit the growth of or kill the fungus or bacteria. 
     
     
         29 . A method of dispersing or inhibiting the growth of a biofilm, or inhibiting the growth of, or killing a fungus or bacteria, comprising contacting the biofilm, fungus or bacteria with an amount of a compound of Formula III of  claim 22 , or a composition comprising an amount of a compound of Formula III, wherein the amount of the compound of Formula III is effective to disperse or inhibit the growth of the biofilm, or inhibit the growth of or kill the fungus or bacteria. 
     
     
         30 .- 31 . (canceled) 
     
     
         32 . A method of treating a surface with a compound of Formula II of  claim 17  comprising contacting the surface with an amount of a compound of Formula II effective to treat the surface, wherein the compound of Formula II acts as a cleaning agent, dispersant, surfactant, biofilm removal agent, or antibiofilm, antifouling, antimicrobial, or anti-fungal agent. 
     
     
         33 . A method of treating a surface with a compound of Formula III of  claim 22  comprising contacting the surface with an amount of a compound of Formula III effective to treat the surface, wherein the compound of Formula III acts as a cleaning agent, dispersant, surfactant, biofilm removal agent, or antibiofilm, antifouling, antimicrobial, or anti-fungal agent.