WO1996038042B1 - Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compound - Google Patents
Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compoundInfo
- Publication number
- WO1996038042B1 WO1996038042B1 PCT/US1996/007676 US9607676W WO9638042B1 WO 1996038042 B1 WO1996038042 B1 WO 1996038042B1 US 9607676 W US9607676 W US 9607676W WO 9638042 B1 WO9638042 B1 WO 9638042B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- heterocyclic compound
- alkyl heterocyclic
- tcmtb
- dodecyl
- growth
- 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
Microbicidal compositions are described. The compositions comprise: (a) 2-(thiocyanomethylthio)benzothiazole (TCMTB) and (b) an N-alkyl heterocyclic compound of formula (I). The variable 'n' ranges from 5 to 17, and the heterocyclic ring defined by (1) is a substituted or unsubstituted ring having four to eight members. Components (a) and (b) 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 or in aqueous systems are also described. Also described is the industrial application of the microbicidal composition in the leather industry, the lumber industry, the papermaking industry, the textile industry, the agricultural industry, and the coating industry, as well as in aqueous systems.
Claims
1. A microbicidal composition comprising:
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) 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 wherein the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
2. A microbicidal composition according to claim 1, 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.
3. A microbicidal composition according to claim 1, wherein the N-alkyl heterocyclic compound is selected from the group consisting of N-4odecyl 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-dodecyl-4-methyl-piperidine and N-dodecyl-2-methyl-piperidine.
4. A microbicidal composition according to claim 1, wherein the N-alkyl heterocyclic compound is
N-dodecyl morpholine.
5. A microbicidal composition according to claim 4 wherein (a) and (b) are present in a combined amount synergistically effective to control the growth of at least one microorganism selected from algae, fungi, and bacteria.
6. A microbicidal composition according to claim 1, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole.
7. A microbicidal composition according to claim.6 wherein (a) and (b) are present in a combined amount synergistically effective to control the growth of at least one microorganism selected from algae, fungi, and bacteria.
8. A microbicidal composition according to claim 1, wherein the composition is an aqueous formulation.
9. A method for controlling the growth of microorganisms on a substrate comprising the step of contacting a substrate susceptible to the growth of microorganisms with
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) 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 the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism on the substrate and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
10. A method according to claim 9, wherein n varies from 9 to 15, and the heterocyclic ring is selected from the group consisting of pyrroiidinyl, 2-pyrroIidinonyl, pyrrolinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, imidazolidinyl, imidazolinyl, imidazolyl, oxazolidinonyl, piperadinyl, piperazinyl, morpholinyl, hexamethyleneiminyl, and
heptamethyleneiminyl.
11. A method according to claim 9, wherein 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-piperidine, N-dodecyl piperiodine, N-dodecyl-4-methyl-piperidine and N-dodecyI-2-methyl- piperidine.
12. A method according to claim 9, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine.
13. A method according to claim 12 wherein (a) and (b) are present in a combined amount synergistically effective to control the growth of at least one microorganism selected from algae, fungi, and bacteria.
14. A method according to claim 8, wherein the N-alkyl heterocyclic compound is N-dodecyl imidazole.
15. A method according to claim 13 , wherein (a) and (b) are present in a combined amount synergistically effective to control the growth of at least one microorganism selected from algae, fungi, and bacteria.
16. A method for controlling the growth of microorganisms on a hide during a leather tanning process comprising the step of contacting the leather with
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) 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 the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism on the hide and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
17. A method according to claim 13, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine or N-dodecyl imidazole and the microorganism is algae, fungi, or bacteria.
18. A liquor for use in a leather-tanning process comprising
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) 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, the TCMTB (a) and the N-alkyl
heterocyclic compound (b) are present in the liquor in a combined amount effective to control the growth of at least one microorganism on the leather, and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a); and the liquor is selected from a pickling liquor, a chrome-tanning liquor, a vegetable-tanning liquor, a post-tan washing liquor, a retarming liquor, a dye liquor, and a fatliquor.
19. A liquor according to claim 18, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine or N-dodecyl imidazole and the microorganism is algae, fungi, or bacteria.
20. A method for controlling the growth of microorganisms on a textile substrate in a textile manufacturing process comprising the step of contacting the textile substrate with
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) and
(b) an N-alkyl heterocyclic compound of the formula: 
wherein n varies from 5 to 17, the heterocyclic ring defined by N R is a substituted or unsubstituted ring having four to eight members, and wherein the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism on the textile substrate and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
21. A method according to claim 20, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine, or N-dodecyl imidazole and the microorganism is algae, fungi, or bacteria.
22. A method for controlling the growth of microorganisms on lumber comprising the step of contacting the lumber with
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) and
(b) an N-alkyl heterocyclic compound of the formula: 
wherein n varies from 5 to 17, the heterocyclic ring defined by N R is a substituted or unsubstituted ring having four to eight members, and wherein the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism on the lumber and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
23. A method according to claim 22, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine or N-dodecyi imidazole and the microorganism is algae, fungi, or bacteria.
24. A method according to claim 22, wherein the contacting step comprises dipping the lumber in a bath containing the TCMTB and the N-alkyl heterocyclic compound.
25. A method according to claim 22, wherein the contacting step comprises spraying an aqueous formulation of the TCMTB and the N-alkyl heterocyclic compounds onto the lumber.
26. A method for controlling the growth of microorganisms on a seed or plant comprising the step of contacting the seed or plant with
(a) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) and
(b) an N-alkyl heterocyclic compound of the formula: 
wherein n varies from 5 to 17, the heterocyclic ring defined by N R is a substituted or unsubstituted ring having four to eight members, and wherein the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
27. A method according to claim 26, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine or N-dodecyl imidazole and the microorganism is algae, fimgi, or bacteria.
28. A method according to claim 26, wherein the contacting step comprises drenching the soil surrounding a seed or plant with an aqueous formulation of the TCMTB and the N-alkyl heterocyclic compound.
29. A method according to claim 26, wherein the contacting step comprises spraying an aqueous formulation of the TCMTB and the N-alkyl heterocyclic compounds onto the seed or plant.
30. 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) 2-(Thiocyanomethylthio)benzothiazole (TCMTB) 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 wherein the TCMTB (a) and the N-alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
31. A method according to claim 30, wherein the N-alkyl heterocyclic compound, is N-dodecyl morpholine or N-dodecyl imidazole and the microorganism is algae, fungi, or bacteria.
32. A method according to claim 30, 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.
33. 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) 2-(ThiocyanomethyIthio)benzothiazole (TCMTB) and
(b) an N-alkyl heterocyclic compound of the formula: 
wherein n varies from 5 to 17, the heterocyclic ring defined by N R is a substituted or unsubstituted ring having four to eight members, and wherein the TCMTB (a) and the N- alkyl heterocyclic compound (b) are present in a combined amount effective to control the growth of at least one microorganism and the amount of the N-alkyl heterocyclic compound (b) present potentiates the microbicidal activity of the TCMTB (a).
34. A method according to claim 33, wherein wet-lap pulp is contacted by spraying an aqueous formulation of the TCMTB and the N-alkyl heterocyclic compound onto the pulp after the pulp leaves a press in the papermaking process.
35. A method according to claim 33, wherein wet-lap pulp is contacted by mixing the TCMTB and an N-alkyl heterocyclic compound into a pulp/white water mixture prior to reaching a formation wire in a papermakiug process.
36. A method according to claim 33, wherein the TCMTB and the N-alkyl heterocyclic compound are incorporated into the body of the paper.
37. A method according to claim 33, wherein contacting step is accomplished by mixing the TCMTB and an N-alkyl heterocyclic compound into a coating composition and the coating composition is applied to the finished paper.
38. A method according to claim 33, wherein the N-alkyl heterocyclic compound is N-dodecyl morpholine or N-dodecyl imidazole and the microorganism is algae, fungi, or bacteria.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69615034T DE69615034T2 (en) | 1995-05-30 | 1996-05-28 | POTENTIALATION OF THE 2- (THIOCYANOMETHYLTHIO) -BENZOTHIAZOLE MICROBICIDE USING AN N-ALKYL HETEROCYCLIC COMPOUND |
| EP96920481A EP0837631B1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compound |
| AT96920481T ATE205049T1 (en) | 1995-05-30 | 1996-05-28 | POTENTIATION OF THE 2-(THIOCYANOMETHYLTHIO)-BENZOTHIAZOLE MICROBICIDE USING AN N-ALKYL HETEROCYCLIC COMPOUND |
| MX9709353A MX9709353A (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compound. |
| CA002222760A CA2222760C (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compound |
| NZ308898A NZ308898A (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)-benzothiazole using an n-alkyl heterocyclic compound |
| JP53657496A JP4082723B2 (en) | 1995-05-30 | 1996-05-28 | Activation of 2- (thiocyanomethylthio) benzothiazole, a microbicide, using N-alkyl heterocyclic compounds |
| BR9608369A BR9608369A (en) | 1995-05-30 | 1996-05-28 | Microbicidal composition method to control the growth of microorganisms and liquids for use in leather tanning processes |
| SK1607-97A SK160797A3 (en) | 1995-05-30 | 1996-05-28 | Microbicidal composition |
| AU58766/96A AU721182B2 (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)benzo thiazole using an n-alkyl heterocyclic compound |
| NO975500A NO975500L (en) | 1995-05-30 | 1997-11-28 | Potentiation of microbiocide 2- (thiocyanomethylthio) benzothiazole using an n-alkyl heterocyclic compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/456,098 | 1995-05-30 | ||
| US08/456,098 US5693631A (en) | 1995-05-30 | 1995-05-30 | Potentiation of the microbicide 2-(thiocyanomethylthio) benzothiazole using an N-alkyl heterocyclic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996038042A1 WO1996038042A1 (en) | 1996-12-05 |
| WO1996038042B1 true WO1996038042B1 (en) | 1997-02-06 |
Family
ID=23811415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/007676 Ceased WO1996038042A1 (en) | 1995-05-30 | 1996-05-28 | Potentiation of the microbicide 2-(thiocyanomethylthio)benzothiazole using an n-alkyl heterocyclic compound |
Country Status (18)
| Country | Link |
|---|---|
| US (4) | US5693631A (en) |
| EP (1) | EP0837631B1 (en) |
| JP (1) | JP4082723B2 (en) |
| AR (1) | AR002135A1 (en) |
| AT (1) | ATE205049T1 (en) |
| AU (1) | AU721182B2 (en) |
| BR (1) | BR9608369A (en) |
| CA (1) | CA2222760C (en) |
| CZ (1) | CZ377997A3 (en) |
| DE (1) | DE69615034T2 (en) |
| ES (1) | ES2162075T3 (en) |
| MX (1) | MX9709353A (en) |
| NO (1) | NO975500L (en) |
| NZ (1) | NZ308898A (en) |
| PT (1) | PT837631E (en) |
| SK (1) | SK160797A3 (en) |
| WO (1) | WO1996038042A1 (en) |
| ZA (1) | ZA964130B (en) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693631A (en) * | 1995-05-30 | 1997-12-02 | Buckman Laboratories International, Inc. | Potentiation of the microbicide 2-(thiocyanomethylthio) benzothiazole using an N-alkyl heterocyclic compound |
| 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 |
| US6576629B1 (en) * | 1999-08-06 | 2003-06-10 | Buckman Laboratories International, Inc. | Microbicidal compositions and methods using combinations of propiconazole and N-alkyl heterocycles and salts thereof |
| US8445536B2 (en) * | 2005-03-31 | 2013-05-21 | Ajinomoto Co., Inc. | Arginine-containing compositions and methods for increasing blood flow using same |
| JP4944843B2 (en) * | 2007-07-18 | 2012-06-06 | ローム アンド ハース カンパニー | Microbicidal composition |
| EP2323628B1 (en) | 2008-08-13 | 2022-04-13 | California Institute of Technology | Carrier nanoparticles and related compositions, methods and systems |
| EP3513812B1 (en) | 2013-03-01 | 2020-07-15 | California Institute of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| US9468681B2 (en) | 2013-03-01 | 2016-10-18 | California Institute Of Technology | Targeted nanoparticles |
| US9132097B2 (en) | 2013-03-01 | 2015-09-15 | California Institute Of Technology | Nanoparticles stabilized with nitrophenylboronic acid compositions |
| CN111643479B (en) | 2015-07-01 | 2023-10-27 | 加州理工学院 | Cationic mucic acid polymer-based delivery system |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2456874A1 (en) * | 1974-12-02 | 1976-06-10 | Henkel & Cie Gmbh | Antimicrobial 2-oxo-1,2,3-oxathiazolidines - contg a long chain aliph, gp., are effective in low concns |
| DE2456974A1 (en) | 1974-12-03 | 1976-06-10 | Adam Koch | Pocket cigarette lighter - has plain rectangular profile with transverse tube to accommodate flint |
| US4293559A (en) * | 1978-03-29 | 1981-10-06 | Buckman Laboratories, Inc. | Slime control compositions and methods of using the same |
| US4479961A (en) * | 1984-01-23 | 1984-10-30 | Nalco Chemical Company | Synergistic fungicide/biocide of 2-(thiocyanomethylthio) benzothiazole and bis (trichloromethyl) sulfone |
| US4595691A (en) * | 1985-07-22 | 1986-06-17 | Nalco Chemical Company | Synergistic biocide of 2-(thiocyanomethylthio) benzothiazole with a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one |
| US4944892A (en) * | 1986-01-02 | 1990-07-31 | Ppg Industries, Inc. | Fungicidal and algicidal detergent compositions |
| JPH0780730B2 (en) * | 1986-10-17 | 1995-08-30 | 株式会社片山化学工業研究所 | Industrial antiseptic and fungicide |
| EP0366839A1 (en) * | 1988-11-03 | 1990-05-09 | Yugen Kaisha Ads. Planning | Manual wiper |
| US5131939A (en) | 1988-12-22 | 1992-07-21 | Rohm And Haas Company | Synergistic microbicidal combinations containing 2-n-octyl-3-isothiazolone and certain commercial biocides |
| US4964892A (en) | 1988-12-22 | 1990-10-23 | Rohm And Haas Company | Synergistic microbicidal combinations containing 2-N-octyl-3-isothiazolone and certain commercial biocides |
| US5041457A (en) | 1989-03-10 | 1991-08-20 | Rohm And Haas Company | Synergistic microbicidal combinations containing 2-n-octyl-3-isothiazolone and certain commercial biocides |
| US5292763A (en) | 1989-11-03 | 1994-03-08 | Rohm And Haas Company | Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides |
| US5468759A (en) | 1991-12-19 | 1995-11-21 | Rohm And Haas Company | Synergistic microbicidal combinations containing 4,5-dichloro-2-octyl-3-isothiazolone and certain commercial biocides |
| US5250194A (en) * | 1991-02-13 | 1993-10-05 | Buckman Laboratories International, Inc. | N-dodecyl heterocyclic compounds useful as industrial microbicides and preservatives |
| DE4309690A1 (en) * | 1993-03-25 | 1994-09-29 | Bayer Ag | Paint |
| JPH06340504A (en) * | 1993-06-01 | 1994-12-13 | Yoshitomi Pharmaceut Ind Ltd | Underwater antifouling agent |
| JPH0769815A (en) * | 1993-06-29 | 1995-03-14 | Yoshitomi Pharmaceut Ind Ltd | Underwater antifouling agent |
| JPH0769315A (en) | 1993-09-03 | 1995-03-14 | Sakae Matsuyama | Apparatus for packing sandwich into wrapping bag |
| US5693631A (en) * | 1995-05-30 | 1997-12-02 | Buckman Laboratories International, Inc. | Potentiation of the microbicide 2-(thiocyanomethylthio) benzothiazole using an N-alkyl heterocyclic compound |
-
1995
- 1995-05-30 US US08/456,098 patent/US5693631A/en not_active Ceased
-
1996
- 1996-05-23 ZA ZA964130A patent/ZA964130B/en unknown
- 1996-05-28 NZ NZ308898A patent/NZ308898A/en not_active IP Right Cessation
- 1996-05-28 CA CA002222760A patent/CA2222760C/en not_active Expired - Fee Related
- 1996-05-28 BR BR9608369A patent/BR9608369A/en not_active IP Right Cessation
- 1996-05-28 JP JP53657496A patent/JP4082723B2/en not_active Expired - Fee Related
- 1996-05-28 AU AU58766/96A patent/AU721182B2/en not_active Ceased
- 1996-05-28 CZ CZ973779A patent/CZ377997A3/en unknown
- 1996-05-28 WO PCT/US1996/007676 patent/WO1996038042A1/en not_active Ceased
- 1996-05-28 PT PT96920481T patent/PT837631E/en unknown
- 1996-05-28 EP EP96920481A patent/EP0837631B1/en not_active Expired - Lifetime
- 1996-05-28 ES ES96920481T patent/ES2162075T3/en not_active Expired - Lifetime
- 1996-05-28 DE DE69615034T patent/DE69615034T2/en not_active Expired - Lifetime
- 1996-05-28 AT AT96920481T patent/ATE205049T1/en active
- 1996-05-28 MX MX9709353A patent/MX9709353A/en not_active IP Right Cessation
- 1996-05-28 SK SK1607-97A patent/SK160797A3/en unknown
- 1996-05-29 AR ARP960102780A patent/AR002135A1/en unknown
-
1997
- 1997-11-26 US US08/979,182 patent/US6060466A/en not_active Ceased
- 1997-11-28 NO NO975500A patent/NO975500L/en not_active Application Discontinuation
-
2002
- 2002-05-09 US US10/141,080 patent/USRE39148E1/en not_active Expired - Fee Related
- 2002-05-09 US US10/141,079 patent/USRE39033E1/en not_active Expired - Lifetime
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