Roseobacticides and uses thereof

Patent metadata

Field	Value
Publication number	US-2016115145-A1
Application number	US-201514848399-A
Country	US
Kind code	A1
Filing date	Sep 9, 2015
Priority date	Aug 20, 2010
Publication date	Apr 28, 2016
Grant date	—

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.

First claim

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.

Assignees

• Harvard College

Inventors

• Kolter Roberto
• Case Rebecca
• Clardy Jon
• Seyedsayamdost Mohammad

Classifications

• C07D307/93 Primary

  condensed with a ring other than six-membered · CPC title

• C07D407/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/38

  condensed with carbocyclic rings · CPC title

• C07D405/14

  containing three or more hetero rings · CPC title

• A01N43/12

  condensed with a carbocyclic ring · CPC title