DE2247370C3 - 1,3,3-Trimethyl-1 -noctylaminomethyl-5-n-octylamino-cyclohexan, Verfahren zu deren Herstellung und deren Verwendung als mikrobicider Wirkstoff - Google Patents
1,3,3-Trimethyl-1 -noctylaminomethyl-5-n-octylamino-cyclohexan, Verfahren zu deren Herstellung und deren Verwendung als mikrobicider WirkstoffInfo
- Publication number
- DE2247370C3 DE2247370C3 DE2247370A DE2247370A DE2247370C3 DE 2247370 C3 DE2247370 C3 DE 2247370C3 DE 2247370 A DE2247370 A DE 2247370A DE 2247370 A DE2247370 A DE 2247370A DE 2247370 C3 DE2247370 C3 DE 2247370C3
- Authority
- DE
- Germany
- Prior art keywords
- trimethyl
- octylamino
- cyclohexane
- compound
- preparation
- 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 10
- 239000004480 active ingredient Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 10
- 238000000034 method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 claims description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 5
- FGJRASWVJRXSOC-UHFFFAOYSA-N 3,3,5-trimethyl-N-octyl-5-[(octylamino)methyl]cyclohexan-1-amine Chemical compound CC1(CC(CC(C1)NCCCCCCCC)(C)C)CNCCCCCCCC FGJRASWVJRXSOC-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 229960004068 hexachlorophene Drugs 0.000 description 2
- -1 n-octyl groups Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229940087291 tridecyl alcohol Drugs 0.000 description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- 241000228197 Aspergillus flavus Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 241001123663 Penicillium expansum Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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
- A01N33/12—Quaternary ammonium compounds
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2247370A DE2247370C3 (de) | 1972-09-27 | 1972-09-27 | 1,3,3-Trimethyl-1 -noctylaminomethyl-5-n-octylamino-cyclohexan, Verfahren zu deren Herstellung und deren Verwendung als mikrobicider Wirkstoff |
| CH1280573A CH579527A5 (OSRAM) | 1972-09-27 | 1973-09-06 | |
| NL7312673A NL162895C (nl) | 1972-09-22 | 1973-09-14 | Werkwijze voor het bereiden van een microbicide preparaat en werkwijze voor het bereiden van een n-dodecyl-koolwaterstofdiamine. |
| AT814673A AT325595B (de) | 1972-09-27 | 1973-09-21 | Verfahren zur herstellung des neuen 1,3,3-trimethyl-1-octylaminomethyl-5-octylamino-cyclohexans |
| FR7334241A FR2200245B1 (OSRAM) | 1972-09-27 | 1973-09-25 | |
| GB4492673A GB1413917A (en) | 1972-09-27 | 1973-09-25 | Octylamino-cyclohexano derivative, a process for its prepa ration and its use in microbicidal preparations |
| NLAANVRAGE7908728,A NL170412C (nl) | 1972-09-22 | 1979-12-03 | Werkwijze voor het bereiden van een microbicide preparaat, gevormd preparaat en werkwijze voor het bereiden van een n,n'-dioctyl-koolwaterstofdiamine. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2247370A DE2247370C3 (de) | 1972-09-27 | 1972-09-27 | 1,3,3-Trimethyl-1 -noctylaminomethyl-5-n-octylamino-cyclohexan, Verfahren zu deren Herstellung und deren Verwendung als mikrobicider Wirkstoff |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2247370A1 DE2247370A1 (de) | 1974-06-06 |
| DE2247370B2 DE2247370B2 (OSRAM) | 1974-09-05 |
| DE2247370C3 true DE2247370C3 (de) | 1975-06-05 |
Family
ID=5857524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2247370A Expired DE2247370C3 (de) | 1972-09-22 | 1972-09-27 | 1,3,3-Trimethyl-1 -noctylaminomethyl-5-n-octylamino-cyclohexan, Verfahren zu deren Herstellung und deren Verwendung als mikrobicider Wirkstoff |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT325595B (OSRAM) |
| CH (1) | CH579527A5 (OSRAM) |
| DE (1) | DE2247370C3 (OSRAM) |
| FR (1) | FR2200245B1 (OSRAM) |
| GB (1) | GB1413917A (OSRAM) |
-
1972
- 1972-09-27 DE DE2247370A patent/DE2247370C3/de not_active Expired
-
1973
- 1973-09-06 CH CH1280573A patent/CH579527A5/xx not_active IP Right Cessation
- 1973-09-21 AT AT814673A patent/AT325595B/de not_active IP Right Cessation
- 1973-09-25 GB GB4492673A patent/GB1413917A/en not_active Expired
- 1973-09-25 FR FR7334241A patent/FR2200245B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2247370A1 (de) | 1974-06-06 |
| DE2247370B2 (OSRAM) | 1974-09-05 |
| GB1413917A (en) | 1975-11-12 |
| ATA814673A (de) | 1975-01-15 |
| FR2200245B1 (OSRAM) | 1976-06-18 |
| FR2200245A1 (OSRAM) | 1974-04-19 |
| AT325595B (de) | 1975-10-27 |
| CH579527A5 (OSRAM) | 1976-09-15 |
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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 |