Protected antimicrobial compounds for high temperature applications
View Patent ↗Provided are protected antimicrobial compounds which are useful for controlling microorganisms in aqueous or water-containing systems, such as oil or gas field fluids, at elevated temperature. The antimicrobial compounds are of the formula I: wherein R, R 1 , R 2 , X and Y are as defined herein.
1. A method for reducing the quantity of microorganisms in an aqueous or water-containing system having a temperature of at least 40° C., the method comprising contacting the aqueous or water-containing system with a protected antimicrobial compound of the formula I:
wherein R is C 1 -C 6 alkyl optionally substituted with hydroxyl;
X and Y are independently O or NR″ wherein R″ is independently H or C 1 -C 6 alkyl; and
R 1 and R 2 are H or R 1 and R 2 , together with the CH—N—CH group to which they are attached, form a piperidinyl ring.
2. A method according to claim 1 wherein X and Y are each O.
3. A method according to claim 1 wherein X and Y are each NH.
4. A method according to claim 1 wherein R is C 1 -C 3 alkyl optionally substituted with one hydroxyl.
5. A method according to claim 1 wherein the compound of formula I is: 7a-methylhexahydro-1H-imidazo[1,5-c]imidazole; 7a-ethylhexahydro-1H-imidazo[1,5-c]imidazole; 2a-methyloctahydro-1,4-dioxa-2a1-azacyclopenta[cd]indene; 2a-ethyloctahydro-1,4-dioxa-2a1-azacyclopenta[cd]indene; (Octahydro-1,4-dioxa-2a′-azacyclopenta[cd]inden-2a-yl)methanol; 2a-methyldecahydro-1,2a-1,4-triazacyclopenta[cd]indene; 2a-ethyldecahydro-1,2a-1,4-triazacyclopenta[cd]indene; or a mixture of two or more thereof.
6. A method according to claim 1 wherein the aqueous or water-containing system is an oil or gas field fluid, a paper machine white water, an industrial recirculating water, a starch solution, a latex emulsion, a hot rolling machining fluid, or an industrial dishwashing or laundry fluid.
7. A method according to claim 1 wherein the aqueous or water-containing system is a fracturing fluid, a drilling fluid, a water flood system, or an oil field water.
8. A compound that is: 7a-methylhexahydro-1H-imidazo[1,5-c]imidazole; 7a-ethylhexahydro-1H-imidazo[1,5-c]imidazole; 2a-methyldecahydro-1,2a-1,4-triazacyclopenta[cd]indene; or 2a-ethyldecahydro-1,2a-1,4-triazacyclopenta[cd]indene.