DE2244778C3 - 1 -n-Dodecylaminomethyl-2-aminocyclopentan, dessen Herstellung und Verwendung als mikrobicider Wirkstoff - Google Patents
1 -n-Dodecylaminomethyl-2-aminocyclopentan, dessen Herstellung und Verwendung als mikrobicider WirkstoffInfo
- Publication number
- DE2244778C3 DE2244778C3 DE2244778A DE2244778A DE2244778C3 DE 2244778 C3 DE2244778 C3 DE 2244778C3 DE 2244778 A DE2244778 A DE 2244778A DE 2244778 A DE2244778 A DE 2244778A DE 2244778 C3 DE2244778 C3 DE 2244778C3
- Authority
- DE
- Germany
- Prior art keywords
- compound
- mixture
- aminocyclopentane
- compounds
- dodecylaminomethyl
- 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.)
- Expired
Links
- 230000003641 microbiacidal effect Effects 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000004480 active ingredient Substances 0.000 title claims 5
- WFEQYYJABZWFBM-UHFFFAOYSA-N 2-[(dodecylamino)methyl]cyclopentan-1-amine Chemical compound C(CCCCCCCCCCC)NCC1C(CCC1)N WFEQYYJABZWFBM-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 229940124561 microbicide Drugs 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 229940087291 tridecyl alcohol Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 5
- -1 n-dodecyl halide Chemical class 0.000 claims 4
- 241000894006 Bacteria Species 0.000 claims 3
- 244000052616 bacterial pathogen Species 0.000 claims 3
- 238000004508 fractional distillation Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 241000233866 Fungi Species 0.000 claims 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 241000195493 Cryptophyta Species 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002563 ionic surfactant Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- IIIUOBIBHJTDAG-UHFFFAOYSA-N n,n-dimethyl-1-phenyltridecan-1-amine Chemical compound CCCCCCCCCCCCC(N(C)C)C1=CC=CC=C1 IIIUOBIBHJTDAG-UHFFFAOYSA-N 0.000 claims 1
- 230000001717 pathogenic effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 3
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000110797 Polygonum persicaria Species 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 229960004068 hexachlorophene Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YKGDAMWMFVRGDH-UHFFFAOYSA-N 1-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1(N)CCCC1 YKGDAMWMFVRGDH-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 101100279436 Caenorhabditis elegans egg-2 gene Proteins 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- YIRYDJKAZDFWPI-UHFFFAOYSA-N N-dodecyl-2-[(dodecylamino)methyl]cyclopentan-1-amine Chemical compound C(CCCCCCCCCCC)NCC1C(CCC1)NCCCCCCCCCCCC YIRYDJKAZDFWPI-UHFFFAOYSA-N 0.000 description 1
- 241000893976 Nannizzia gypsea Species 0.000 description 1
- 241000863548 Paralecanium expansum Species 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244778A DE2244778C3 (de) | 1972-09-13 | 1972-09-13 | 1 -n-Dodecylaminomethyl-2-aminocyclopentan, dessen Herstellung und Verwendung als mikrobicider Wirkstoff |
| US383679A US3896171A (en) | 1972-09-13 | 1973-07-30 | 1-dodecylaminomethyl-2-amino-cyclopentane |
| CH1172773A CH587220A5 (enExample) | 1972-09-13 | 1973-08-15 | |
| BE134866A BE803942A (fr) | 1972-09-13 | 1973-08-23 | Composes microbicides, leur procede de preparation et leur utilisation |
| FR7332568A FR2224149A1 (en) | 1972-09-13 | 1973-09-11 | 1,2 Substd cyclopentanes - used as bactericides |
| NL7312589A NL162894C (nl) | 1972-09-13 | 1973-09-12 | Werkwijze voor het bereiden van een microbicide preparaat en werkwijze voor het bereiden van een n,n&001-dialkylalkyleenderivaat. |
| AT790473A AT326103B (de) | 1972-09-13 | 1973-09-12 | Verfahren zur herstellung des neuen 1-dodecylaminomethyl-2-amino-cyclopentans |
| NLAANVRAGE7908727,A NL170625C (nl) | 1972-09-13 | 1979-12-03 | Werkwijze voor het bereiden van een microbicide preparaat, gevormd preparaat en werkwijze voor het bereiden van een n-alkyl-alkyleendiaminederivaat. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244778A DE2244778C3 (de) | 1972-09-13 | 1972-09-13 | 1 -n-Dodecylaminomethyl-2-aminocyclopentan, dessen Herstellung und Verwendung als mikrobicider Wirkstoff |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2244778A1 DE2244778A1 (de) | 1974-04-04 |
| DE2244778B2 DE2244778B2 (de) | 1974-06-27 |
| DE2244778C3 true DE2244778C3 (de) | 1975-02-20 |
Family
ID=5856145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2244778A Expired DE2244778C3 (de) | 1972-09-13 | 1972-09-13 | 1 -n-Dodecylaminomethyl-2-aminocyclopentan, dessen Herstellung und Verwendung als mikrobicider Wirkstoff |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3896171A (enExample) |
| AT (1) | AT326103B (enExample) |
| BE (1) | BE803942A (enExample) |
| CH (1) | CH587220A5 (enExample) |
| DE (1) | DE2244778C3 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4140798A (en) * | 1976-11-24 | 1979-02-20 | Kewanee Industries, Inc. | Method of inhibiting microorganisms |
| DE2658401A1 (de) * | 1976-12-23 | 1978-07-06 | Merck Patent Gmbh | Cyclopentan-1-amine, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| US6712347B1 (en) * | 2003-02-18 | 2004-03-30 | Clyde R. Fredrickson | Automatic truss jig setting system |
| US7922158B2 (en) | 2003-02-18 | 2011-04-12 | Truss Industry Production Systems, Inc. | Automatic truss jig setting system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3227761A (en) * | 1962-12-26 | 1966-01-04 | Monsanto Res Corp | Fluorine-containing amines |
-
1972
- 1972-09-13 DE DE2244778A patent/DE2244778C3/de not_active Expired
-
1973
- 1973-07-30 US US383679A patent/US3896171A/en not_active Expired - Lifetime
- 1973-08-15 CH CH1172773A patent/CH587220A5/xx not_active IP Right Cessation
- 1973-08-23 BE BE134866A patent/BE803942A/xx not_active IP Right Cessation
- 1973-09-12 AT AT790473A patent/AT326103B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2244778A1 (de) | 1974-04-04 |
| DE2244778B2 (de) | 1974-06-27 |
| CH587220A5 (enExample) | 1977-04-29 |
| BE803942A (fr) | 1973-12-17 |
| AT326103B (de) | 1975-11-25 |
| US3896171A (en) | 1975-07-22 |
| ATA790473A (de) | 1975-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |