Antimicrobial compounds

Patent metadata

Field	Value
Publication number	US-9550740-B2
Application number	US-201314565890-A
Country	US
Kind code	B2
Filing date	Jun 12, 2013
Priority date	Jun 19, 2012
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

Provided are compounds which are useful for controlling microorganisms in aqueous or water-containing systems or in systems which are exposed to moisture, including at elevated temperature. The antimicrobial compounds are of the formula I:

wherein n, R 1 , R 2 , R 3 , R 4 , R 5 , and X are as defined herein.

First claim

We claim:

1. A compound of formula I:

wherein n is 0 or 1;
R 1 is linear or branched C 1 -C 10 alkyl;
R 2 is H, linear or branched C 1 -C 10 alkyl, C 3 -C 8 cycloalkyl, or aryl;
R 3 , R 4 , and R 5 at each occurrence are independently H, linear or branched C 1 -C 10 alkyl, or C 3 -C 8 cycloalkyl;
or R 2 and R 3 together with the carbon to which they are attached form C 3 -C 3 cycloalkyl;
or R 4 and R 5 together with the carbon to which they are attached form C 3 -C 3 cycloalkyl; and

X is O or NR 6 , wherein R 6 is linear or branched C 1 -C 6 alkyl.

2. The compound of claim 1 n is 1, R 2 is aryl and R 3 , R 4 , and R 5 are each H.

3. The compound of claim 1 wherein n is 0, and R 2 , R 3 , R 4 , and R 5 are each H.

4. The compound of claim 1 wherein X is O.

5. The compound of claim 1 that is: 1,3-bis(3-methyloxazolidin-2-yl)propane; 1,3-bis (3-butyloxazolidin-2-yl)propane; 1,3-bis(3-octyloxazolidin-2-yl)propane; or 1,3-bis(3-methyl-6-phenyl-1,3-oxazinan-2-yl)propane.

6. A method for controlling microorganisms in an aqueous or water-containing system or in a system which is exposed to moisture, the method comprising contacting the system with the compound of claim 1 .

7. The method of claim 6 wherein the system is at a temperature of at least 40° C.

8. The method of claim 6 wherein the system is an oil or gas field fluid, paper machine white water, industrial recirculating water, a starch solution, a latex or polymer emulsion, a coating or building product or household product or personal care product which is manufactured at elevated temperature, a plastic, a hot rolling machining fluid, an industrial dishwashing or laundry fluid, an animal biosecurity fluid, or a high level disinfection fluid.

9. The method of claim 6 wherein the system is a fracturing fluid, a drilling fluid, a water flood system, an oil field water, or a produced fluid.

Assignees

• Dow Global Technologies Llc
• Rohm & Haas

Inventors

• Coburn Charles E
• Koehler Thomas
• Mcginley Heather R
• Peera Asghar A

Classifications

• C07D263/06

  with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms · CPC title

• C07D265/06 Primary

  not condensed with other rings · CPC title

• A01N43/76

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title

• A01N43/86

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3 · CPC title

• C07D263/04

  having no double bonds between ring members or between ring members and non-ring members · CPC title