Roseobacticides and uses thereof

Abstract

Embodiments of the invention relate to compounds and methods for controlling algal growth, for example, in bodies of water or surfaces exposed to algae. Provided are compounds having algicidal activities and methods of use of these compounds as well as formulations and compositions comprising the compound having algicidal activities.

What is claimed: 
     
         1 . A compound comprising the formula: 
       
         
           
           
               
               
           
         
         wherein R 1  is optionally substituted aryl, optionally substituted heteroary, optionally substituted phenyl or an optionally substitute indole; 
         wherein R 2  is OR 7 , SR 7 , SO 2 R 7 , or SSR 7 ; 
         wherein R 7  is H, methyl, ethyl, propyl, butyl, pentyl, hexyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted acyl, optionally substituted arylcarbonyl, optionally substituted aryl or formula (I); 
         wherein m is 0, 1, 2, 3, or 4, and 
         wherein R 3  is OR 6 , SR 6 , SSR 6 , halogen, CN, N(R 6 ) 2 , NO 2 , optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl; 
         wherein R 6  is H, methyl, ethyl, propyl, butyl, pentyl, hexy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted acyl; 
         and wherein X is O, S, NR 6 . 
       
     
     
         2 . The compound of  claim 1 , wherein the R 1  optionally substituted phenyl is 
       
         
           
           
               
               
           
         
         wherein R 4  is H, OR 6 , SR 6 , halogen, CN, CF 3 , N(R 6 ) 2 , NO 2 , optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl; 
         n is 0, 1, 2, 3, or 4; and 
         R 5  is OR 6 , SR 6 , SSR 6 , halogen, CN, CF 3 , N(R 6 ) 2 , NO 2 , optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl. 
       
     
     
         3 . The compound of  claim 2 , wherein R 4  is H or OR 6 . 
     
     
         4 . The compound of  claim 2 , wherein R 4  is H, OH, or OMe. 
     
     
         5 . The compound of  claim 2 , wherein R 4  is 
       
         
           
           
               
               
           
         
       
     
     
         6 . The compound of  claim 1 , wherein R 7  is 
       
         
           
           
               
               
           
         
       
       wherein the R 1 , R 3 , and X are as defined for formula (I). 
     
     
         7 . The compound of  claim 1 , wherein the R 7    optionally substituted arylcarbonyl is   
       
         
           
           
               
               
           
         
       
       wherein R 8  is H, OR 6 , SR 6 , halogen, CN, CF 3 , N(R 6 ) 2 , NO 2 , optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl. 
     
     
         8 . The compound of  claim 1 , wherein m is 1 and R 3  is OH, SH, or SSH. 
     
     
         9 . The compound of  claim 1 , wherein X is O. 
     
     
         10 . The compound of  claim 1 , wherein the compound is selected from the group consisting of 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         11 . The compound of  claim 1 , wherein the compound has algicidal activity. 
     
     
         12 . The compound of  claim 11 , wherein the algicidal activity has an LC 50  of 0.01 μM to 35 μM. 
     
     
         13 . The compound of  claim 11 , wherein the algicide composition specifically kills the algae  Emiliana huxleyi.    
     
     
         14 . A composition comprising a compound of  claim 1 . 
     
     
         15 . An algicide formulation comprising a compound of  claim 1 . 
     
     
         16 . The algicide formulation of  claim 15  further comprising an algicide, a herbicide, a bactericide or a fungicide. 
     
     
         17 . A method of controlling algal growth in a body of water, the method comprising adding to the water a sufficient amount of a compound, composition or formulation of  claim 1  or a salt thereof to kill or inhibit growth of algae in the water. 
     
     
         18 . The method of  claim 17 , wherein the body of water is selected from the group consisting of swimming pools, aquaculture ponds, freshwater ponds, aquariums, urban drainage systems and industrial cooling water systems. 
     
     
         19 . A method for protecting an industrial product against infestation and destruction by algae, cyanobacteria and other photoautotrope microorganisms, the method comprising incorporating in the industrial product an effective amount of a compound, composition or formulation of  claim 1  or a salt thereof to kill and/or prevent algae growth. 
     
     
         20 . A material or industrial product comprising a compound, composition or formulation of  claim 1 , wherein the compound, composition or formulation applied thereon or is incorporated within. 
     
     
         21 . The material or industrial product of  claim 20 , wherein material or industrial product is selected from the group consisting of paints, polyvinyl chloride-containing plastics, varnishes, sealing materials, textile finishes, synthetic resin rendering, wood finishes and coatings, and roof tile coatings.