WO1996038043B1 - Potentiation of biocide activity using an n-alkyl heterocyclic compound - Google Patents
Potentiation of biocide activity using an n-alkyl heterocyclic compoundInfo
- Publication number
- WO1996038043B1 WO1996038043B1 PCT/US1996/007677 US9607677W WO9638043B1 WO 1996038043 B1 WO1996038043 B1 WO 1996038043B1 US 9607677 W US9607677 W US 9607677W WO 9638043 B1 WO9638043 B1 WO 9638043B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- dodecyl
- heterocyclic compound
- alkyl heterocyclic
- methyl
- microbicide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Abstract
A method for increasing the effectiveness of a microbicide is described. In the method, a microbicide and an N-alkyl heterocyclic compound are applied to a substrate or aqueous system subject to the growth of microorganisms. The N-alkyl heterocyclic compound is applied in an amount effective to increase the microbicidal activity of the microbicide. The N-alkyl heterocyclic compound has formula (I). The variable 'n' ranges from 5 to 17, and the heterocyclic ring defined by (a) is a substituted or unsubstituted ring having four to eight members. Microbicidal compositions are described where the microbicide and the N-alkyl heterocyclic compound are present in a combined amount effective to control the growth of at least one microorganism. Methods for controlling the growth of microorganisms on various substrates and in various aqueous systems are also described. The combination of the microbicide and the N-alkyl heterocyclic compound is particularly useful as a microbicide in the leather industry, the lumber industry, the papermaking industry, the textile industry, the agricultural industry, and the coating industry, as well as in industrial process waters.
Claims
AMENDED CLAIMS
[received by the International Bureau on 17 December 1996 (17.12.96); original claims 1, 5, 11, 17 and 22 amended; remaining claims unchanged (6 pages)]
1. A method to increase the effectiveness of a microbicide comprising the step of applying at least one microbicide and an N-alkyl heterocyclic compound to a substrate or aqueous system subject to the growth of microorganisms, wherein the N-alkyl heterocyclic compound has the formula:
in which n varies from 5 to 17 and the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members and the N-alkyl heterocyclic compound is applied in an amount effective to potentiate the microbicidal activity of the microbicide.
2. A method according to claim 1, wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1 ,3-diol, iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3- nitrilopropionamide, tribromophenol, and 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpnoline, N-dodecyl imidazole, N-dodecyl-2.6-dimethyl-morpholine, N-dodecyl- 5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine.
3. A method according to claim 2, wherein the N-alkyl heterocyclic compound is N-dodecyl morpnoline.
4. A method according to claim 2, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole.
5. A microbicidal composition comprising:
(a) at least one microbicide and
(b) an N-alkyl heterocyclic compound of the formula:
herein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members, and wherein (a) and (b) are present in a combined amount effective to control the growth, of at least one microorganism and the N-alkyl heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
6. A microbicidal composition according to claim 5, wherein n varies from 9 to 15, and die heterocyclic ring is selected from the group consisting of pyrrolidinyl, 2-pyrrolidinonyl, pyrrolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, imidazolidinyl, imidazolinyl, imidazolyl, oxazolidinonyl, piperidinyl, piperazinyl, morpholinyl, hexamethyleneiminyl, and
heptamethyleneiminyl.
7. A microbicidal composition according to claim 5, wherein microbicide selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1 ,3-diol iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from the group consisting of N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperigine, N-dodecyl piperidine, N-dodecyl-4-methylpiperidine and N-dodecyl-2-methyl-piperidine.
8. A microbicidal composition according to claim 5, wherein the N-alkyl heterocyclic compound is N-dodecyl morphoiine and the microorganism is selected from algae, fungi, and bacteria.
9. A microbicidal composition, according to claim 5, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole and the microorganism is selected from algae, fungi, and bacteria. 10. A microbicidal composition according to claim 5, wherein the composition is an aqueous formulation.
11. A method for controiling the growth of microorganisms on a substrate comprising the step of contacting a substrate susceptible to the growth of microorganisms with
(a) at least one microbicide, and
(b) an N-alkyl heterocyclic compound of the formula:
wherein n may be from 5 to 17, the heterocyclic ring defined by
is a substituted or unsubstituted ring having four to eight members, and wherein (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism on the substrate and the N-alkyl heterocyclic compound (b) is present in sn amount effective to potentiate the microbicidal activity of the microbicide (a).
12. A method according to claim 11, wherein n varies from 9 to 15, and the heterocyclic ring is selected from the group consisting of pyrrolidinyl, 2-pyrrolidinonyl, pyrrolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, imidazolidinyl, imidazolinyl, imidazolyl, oxazolidinonyl, piperidinyl, piperazinyl, morpholinyl, hexamethyleneiminyl, and
heptamethyleneiminyl.
13. A method according to claim 11. wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-metbyl-4-isothiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl butyl carbamate, lodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, and 1 ,2-benzisothiazoline-3-one, and mixtures thereof, and
the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine- N-dodecyl-5-chlororaethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolichne, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine. N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine.
14. A method according to claim 11. wherein the N-alkyl heterocyclic compound 35 N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria. 15. A method according to claim 11 , wherein the N-alkyl heterocyclic compound is
N-dodecyl imidazole. and the microorganism is selected from algae. fungi, and bacteria.
16. A method of claim 11 wherein the substrate is a hide, a textile substrate, lumber, a seed, or a plant.
17. A method for controlling the growth of microorganisms in an aqueous system capable of supporting growth of a microorganism comprising the step of treating the aqueous system with
(a) at least one microbicide, and
(b) an N-alkyl heterocyclic compound of the formula;
wherein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight m embers, and wherein (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism and the N-alkyl heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
18. A method according to claim 17, wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isotbiazolin-3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl butyl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribromophenol, and 1,2-benzisothiazoIine-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyI-2-pyrrolidinone, N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine. 19. A method according to claim 17, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria.
28. A method according to claim 17, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole, and. the microorganism is selected from algae, fungi, and bacteria.
21. A method according to claim 17, wherein said aqueous system is selected from the group consisting of a latex, a metal working fluid, an aqueous emulsion, an aqueous detergent, cooling water, and an aqueous resin formulation.
22. A method for controlling the growth of microorganisms on pulp or paper in a papermaking process, comprising the step of contacting the pulp or paper with
(a) at least one tnicrobicide, and
(b) an N-alkyl heterocyclic compound of the formula:
wherein n varies from 5 to 17, the heterocyclic ring defined by is a substituted or
unsubstituted ring having four to eight members, and (a) and (b) are present in a combined amount effective to control the growth of at least one microorganism and the N-alkyl
heterocyclic compound (b) is present in an amount effective to potentiate the microbicidal activity of the microbicide (a).
23. A method according to claim 22, wherein the pulp is contacted by mixing the microbicide and an N-alkyl heterocyclic compound into a pulp slurry prior to reaching a formation wire in a papermaking process.
24. A method according to claim 22. wherein the microbicide is selected from 5-chloro-2-methyl-4-isothiazolin-3-one, 2-methyl-4-isothiazolin- 3-one, 2-bromo-2-nitropropane-1,3-diol, iodopropargyl buryl carbamate, iodopropargyl carbamate, 2,2-dibromo-3-nitrilopropionamide, tribaromophenol, and 1,2-benzisothiazoline-3-one, and mixtures thereof, and the N-alkyl heterocyclic compound is selected from N-dodecyl morpholine, N-dodecyl imidazole, N-dodecyl-2,6-dimethyl-morpholine, N-dodecyl-5-chloromethyl-2-oxazolidinone, N-dodecyl-2-pyrrolidinone. N-dodecyl hexamethyleneimine, N-dodecyl pyrrolidine, N-dodecyl-3-methyl-piperidine, N-dodecyl piperidine, N-dodecyI-4-methyl-pipendine and N-dodecyl-2-methyl-piperidine.
25 A method according to claim 22, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine and the microorganism is selected from algae, fungi, and bacteria.
26. A method according to claim 22, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole, and the microorganism is selected from algae, fungi, and bacteria.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU59315/96A AU5931596A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocycl ic compound |
| CA002222864A CA2222864C (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| NZ309305A NZ309305A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| JP8536575A JPH11506103A (en) | 1995-05-30 | 1996-05-28 | Activation of bactericidal effect using N-alkylheterocyclic compound |
| SK1608-97A SK160897A3 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| DE69629713T DE69629713T2 (en) | 1995-05-30 | 1996-05-28 | BIOCIDAL ENHANCEMENT OF EFFECT THROUGH N-ALKYL-HETEROCYCLIC COMPOUND |
| MX9709354A MX9709354A (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound. |
| AT96916627T ATE247902T1 (en) | 1995-05-30 | 1996-05-28 | BIOCIDAL EFFECT INCREASED THROUGH N-ALKYL HETEROCYCLIC COMPOUND |
| BR9608368A BR9608368A (en) | 1995-05-30 | 1996-05-28 | Method to increase the effectiveness of a microbicidal agent microbicidal composition and method to control the growth of microorganisms |
| EP96916627A EP0857021B1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
| NO975501A NO975501L (en) | 1995-05-30 | 1997-11-28 | Potentiation of biocidal activity using an N-alkyl heterocyclic compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/453,001 US6034081A (en) | 1995-05-30 | 1995-05-30 | Potentiation of biocide activity using an N-alkyl heterocyclic compound |
| US08/453,001 | 1995-05-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996038043A1 WO1996038043A1 (en) | 1996-12-05 |
| WO1996038043B1 true WO1996038043B1 (en) | 1997-01-30 |
Family
ID=23798832
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/007677 Ceased WO1996038043A1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of biocide activity using an n-alkyl heterocyclic compound |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6034081A (en) |
| EP (1) | EP0857021B1 (en) |
| JP (1) | JPH11506103A (en) |
| CN (1) | CN1190869A (en) |
| AR (1) | AR002134A1 (en) |
| AT (1) | ATE247902T1 (en) |
| AU (1) | AU5931596A (en) |
| BR (1) | BR9608368A (en) |
| CA (1) | CA2222864C (en) |
| CZ (1) | CZ378097A3 (en) |
| DE (1) | DE69629713T2 (en) |
| ES (1) | ES2205033T3 (en) |
| MX (1) | MX9709354A (en) |
| NO (1) | NO975501L (en) |
| NZ (1) | NZ309305A (en) |
| PT (1) | PT857021E (en) |
| SK (1) | SK160897A3 (en) |
| WO (1) | WO1996038043A1 (en) |
| ZA (1) | ZA964131B (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19722858B4 (en) | 1997-05-23 | 2004-01-29 | Schülke & Mayr GmbH | Compositions based on iodopropynyl and formaldehyde depot compounds and their use as preservatives |
| DE19737315C2 (en) * | 1997-08-27 | 2001-05-10 | Herbert Widulle | Use of mixtures of substances to kill mycobacteria |
| US5929073A (en) * | 1997-09-16 | 1999-07-27 | Buckman Laboratories International, Inc. | Synergistic antimicrobial compositions containing dodecylmorpholine a salt thereof and dodecylamine or a salt thereof |
| US6866906B2 (en) * | 2000-01-26 | 2005-03-15 | International Paper Company | Cut resistant paper and paper articles and method for making same |
| US20030166483A1 (en) * | 2000-04-04 | 2003-09-04 | Michael Heinzel | Use of 3-iodine-2-propinyl-carbamates as antimicrobial active agent |
| IL138771A0 (en) * | 2000-09-28 | 2001-10-31 | Bromine Compounds Ltd | A compacted 2,2-dibromo-3-nitrilopropionamide |
| NZ528924A (en) * | 2001-04-11 | 2005-05-27 | Int Paper Co | Paper articles exhibiting long term storageability |
| US7279071B2 (en) * | 2001-04-11 | 2007-10-09 | International Paper Company | Paper articles exhibiting water resistance and method for making same |
| US20060254736A1 (en) * | 2001-04-11 | 2006-11-16 | Jackson John F | Paper articles exhibiting water resistance and method for making same |
| RU2387752C2 (en) | 2002-09-13 | 2010-04-27 | Интернэшнл Пейпер Компани | Paper of improved rigidity and bulk and method of its producing |
| JP4546132B2 (en) * | 2004-04-13 | 2010-09-15 | 日本エンバイロケミカルズ株式会社 | Industrial sterilization composition and method for preparing the same |
| WO2006014446A1 (en) * | 2004-07-06 | 2006-02-09 | International Paper Company | Paper substrates containing an antimicrobial compound as well as methods of making and using the same |
| US8034847B2 (en) | 2005-03-11 | 2011-10-11 | International Paper Company | Compositions containing expandable microspheres and an ionic compound, as well as methods of making and using the same |
| JP5291292B2 (en) * | 2007-02-01 | 2013-09-18 | 協同油脂株式会社 | Metal working fluid and metal working method |
| US8557292B2 (en) | 2008-08-13 | 2013-10-15 | California Institute Of Technology | Carrier nanoparticles and related compositions, methods and systems |
| US8382945B2 (en) | 2008-08-28 | 2013-02-26 | International Paper Company | Expandable microspheres and methods of making and using the same |
| WO2010148156A1 (en) | 2009-06-16 | 2010-12-23 | International Paper Company | Anti-microbial paper substrates useful in wallboard tape applications |
| GB201010374D0 (en) * | 2010-06-21 | 2010-08-04 | Mtp Innovations Ltd | Disinfectant composition |
| EP2594133B1 (en) * | 2011-11-16 | 2014-03-19 | Rohm and Haas Company | Hindered primary chlorinated amine in a latex formulation |
| EP3513812B1 (en) | 2013-03-01 | 2020-07-15 | California Institute of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| US9132097B2 (en) | 2013-03-01 | 2015-09-15 | California Institute Of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| ES2905266T3 (en) * | 2013-11-19 | 2022-04-07 | Arch Chem Inc | enhanced preservative |
| ES2980216T3 (en) | 2015-07-01 | 2024-09-30 | California Inst Of Techn | Delivery systems based on cationic mucic acid polymers |
| JP6352507B1 (en) * | 2017-07-27 | 2018-07-04 | 第一工業製薬株式会社 | Hydrogen gas barrier film composition and hydrogen gas barrier film using the same |
| US20190249360A1 (en) | 2018-02-15 | 2019-08-15 | Buckman Laboratories International, Inc. | Method And System For Tagging Leather Or Hides Treated With Biocide And Identifying Same |
| WO2019241327A1 (en) | 2018-06-13 | 2019-12-19 | California Institute Of Technology | Nanoparticles for crossing the blood brain barrier and methods of treatment using the same |
| JP2024546893A (en) | 2021-12-17 | 2024-12-26 | ビーエーエスエフ ソシエタス・ヨーロピア | Compositions Comprising Antimicrobial Agents and Carboxamides |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923870A (en) * | 1973-07-11 | 1975-12-02 | Troy Chemical Corp | Urethanes of 1-halogen substituted alkynes |
| US4173643A (en) * | 1973-12-20 | 1979-11-06 | Rohm And Haas Company | Synergistic microbiocidal compositions |
| US5182277A (en) * | 1985-03-04 | 1993-01-26 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | Fungicides and plant-growth controlling agents |
| DD243632B1 (en) * | 1985-12-02 | 1990-09-05 | Fahlberg List Veb | AGENTS FOR THE CONTROL OF PHYTOPATHOGENIC BACTERIA AND MUSHROOMS |
| US4661503A (en) * | 1986-06-16 | 1987-04-28 | Nalco Chemical Company | Synergistic biocide of dodecyl guanidine hydrochloride and a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one |
| US4945109A (en) * | 1988-08-24 | 1990-07-31 | Buckman Laboratories International, Inc. | Ester of carbamic acid useful as a microbicide and a preservative |
| US5219875A (en) * | 1990-11-27 | 1993-06-15 | Rohm And Haas Company | Antimicrobial compositions comprising iodopropargyl butylcarbamate and 1,2-benzisothiazolin-3-one and methods of controlling microbes |
| US5250194A (en) * | 1991-02-13 | 1993-10-05 | Buckman Laboratories International, Inc. | N-dodecyl heterocyclic compounds useful as industrial microbicides and preservatives |
| ZA926535B (en) * | 1991-11-07 | 1994-09-30 | Buckman Laboraties Internation | Synergistic combinations of iodopropargyl compounds with 1,2-benzisothiazolin-3-one in controlling fungal and bacterial growth in aqueous fluids |
| DE4217881A1 (en) * | 1992-05-29 | 1993-12-02 | Henkel Kgaa | Antimicrobial active ingredient mixtures |
| AU6240294A (en) * | 1993-02-26 | 1994-09-14 | Wesley-Jessen Corporation | Method and composition for disinfecting contact lenses |
| DE4316845A1 (en) * | 1993-05-19 | 1994-11-24 | Bayer Ag | Microbicidal agents |
-
1995
- 1995-05-30 US US08/453,001 patent/US6034081A/en not_active Expired - Lifetime
-
1996
- 1996-05-23 ZA ZA964131A patent/ZA964131B/en unknown
- 1996-05-28 BR BR9608368A patent/BR9608368A/en not_active IP Right Cessation
- 1996-05-28 ES ES96916627T patent/ES2205033T3/en not_active Expired - Lifetime
- 1996-05-28 NZ NZ309305A patent/NZ309305A/en unknown
- 1996-05-28 EP EP96916627A patent/EP0857021B1/en not_active Expired - Lifetime
- 1996-05-28 AU AU59315/96A patent/AU5931596A/en not_active Abandoned
- 1996-05-28 JP JP8536575A patent/JPH11506103A/en not_active Ceased
- 1996-05-28 CZ CZ973780A patent/CZ378097A3/en unknown
- 1996-05-28 DE DE69629713T patent/DE69629713T2/en not_active Expired - Lifetime
- 1996-05-28 CA CA002222864A patent/CA2222864C/en not_active Expired - Fee Related
- 1996-05-28 SK SK1608-97A patent/SK160897A3/en unknown
- 1996-05-28 MX MX9709354A patent/MX9709354A/en not_active IP Right Cessation
- 1996-05-28 WO PCT/US1996/007677 patent/WO1996038043A1/en not_active Ceased
- 1996-05-28 PT PT96916627T patent/PT857021E/en unknown
- 1996-05-28 AT AT96916627T patent/ATE247902T1/en active
- 1996-05-28 CN CN96195490A patent/CN1190869A/en active Pending
- 1996-05-29 AR ARP960102779A patent/AR002134A1/en unknown
-
1997
- 1997-11-28 NO NO975501A patent/NO975501L/en not_active Application Discontinuation
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