DE1907149B2 - Gemische aus Alkylieningsprodukten der N- eckige Klammer auf 3-(NMsP-Dialkylamino)-propyl eckige Klammer zu asparaginsäure und diese enthaltende bakericide und fungicide Mittel - Google Patents
Gemische aus Alkylieningsprodukten der N- eckige Klammer auf 3-(NMsP-Dialkylamino)-propyl eckige Klammer zu asparaginsäure und diese enthaltende bakericide und fungicide MittelInfo
- Publication number
- DE1907149B2 DE1907149B2 DE19691907149 DE1907149A DE1907149B2 DE 1907149 B2 DE1907149 B2 DE 1907149B2 DE 19691907149 DE19691907149 DE 19691907149 DE 1907149 A DE1907149 A DE 1907149A DE 1907149 B2 DE1907149 B2 DE 1907149B2
- Authority
- DE
- Germany
- Prior art keywords
- cooh
- compounds
- mixture
- mixtures
- alkyl
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 27
- 230000029936 alkylation Effects 0.000 title claims 3
- 238000005804 alkylation reaction Methods 0.000 title claims 3
- 239000000417 fungicide Substances 0.000 title claims 3
- 235000003704 aspartic acid Nutrition 0.000 title description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 title description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 24
- 230000000844 anti-bacterial effect Effects 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000645 desinfectant Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 230000000622 irritating effect Effects 0.000 claims description 3
- 210000004400 mucous membrane Anatomy 0.000 claims description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 229960003237 betaine Drugs 0.000 claims description 2
- 230000000855 fungicidal effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000002070 germicidal effect Effects 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000002280 amphoteric surfactant Substances 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000003899 bactericide agent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012459 cleaning agent Substances 0.000 claims 1
- 239000002085 irritant Substances 0.000 claims 1
- 230000007794 irritation Effects 0.000 claims 1
- PDZKPUQLQNDXMQ-UHFFFAOYSA-M sodium 5-(carbamoyldiazenyl)-6-hydroxy-1-methyl-2,3-dihydroindole-2-sulfonate Chemical compound CN1C(CC2=CC(=C(C=C21)O)N=NC(=O)N)S(=O)(=O)[O-].[Na+] PDZKPUQLQNDXMQ-UHFFFAOYSA-M 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 N, N-Dipropylamino Chemical group 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000721 bacterilogical effect Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 231100000286 mucous membrane, eye irritation or corrosion testing Toxicity 0.000 description 3
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 210000000795 conjunctiva Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DSAJRCNSPOSHPL-UHFFFAOYSA-N didodecyl sulfate Chemical compound CCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCC DSAJRCNSPOSHPL-UHFFFAOYSA-N 0.000 description 1
- VQUHJCXEMYESBB-UHFFFAOYSA-N dihexadecyl sulfate Chemical compound CCCCCCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCCCCCC VQUHJCXEMYESBB-UHFFFAOYSA-N 0.000 description 1
- BNMHIKTUFBWOAM-UHFFFAOYSA-N dioctadecyl sulfate Chemical compound CCCCCCCCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCCCCCCCC BNMHIKTUFBWOAM-UHFFFAOYSA-N 0.000 description 1
- OOZFJMRPUVMHEW-UHFFFAOYSA-N dioctyl sulfate Chemical compound CCCCCCCCOS(=O)(=O)OCCCCCCCC OOZFJMRPUVMHEW-UHFFFAOYSA-N 0.000 description 1
- ZCBCCZQKHUFTPV-UHFFFAOYSA-N ditetradecyl sulfate Chemical compound CCCCCCCCCCCCCCOS(=O)(=O)OCCCCCCCCCCCCCC ZCBCCZQKHUFTPV-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH238768A CH509267A (de) | 1968-02-19 | 1968-02-19 | Verfahren zur Herstellung von Mischungen von Aminosäurederivaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1907149A1 DE1907149A1 (de) | 1969-09-11 |
| DE1907149B2 true DE1907149B2 (de) | 1974-07-11 |
| DE1907149C3 DE1907149C3 (enrdf_load_stackoverflow) | 1975-03-06 |
Family
ID=4232587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691907149 Granted DE1907149B2 (de) | 1968-02-19 | 1969-02-13 | Gemische aus Alkylieningsprodukten der N- eckige Klammer auf 3-(NMsP-Dialkylamino)-propyl eckige Klammer zu asparaginsäure und diese enthaltende bakericide und fungicide Mittel |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT290489B (enrdf_load_stackoverflow) |
| CH (1) | CH509267A (enrdf_load_stackoverflow) |
| DE (1) | DE1907149B2 (enrdf_load_stackoverflow) |
| FR (1) | FR2014111A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1228735A (enrdf_load_stackoverflow) |
| NL (1) | NL6902241A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022059A3 (en) * | 1979-05-08 | 1981-06-03 | Ciba-Geigy Ag | N-substituted esters of aspartic acid, their preparation and use |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2844814A1 (de) * | 1978-10-14 | 1980-04-24 | Max Rosenberg | Zinkchelate bildende fungizide zusammensetzung |
| JPS59196809A (ja) * | 1983-04-22 | 1984-11-08 | Lion Corp | 毛髪化粧料組成物 |
| DE3509822A1 (de) * | 1985-03-19 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Aminobernsteinsaeurederivate und ihre verwendung als emulgatoren fuer polymerdispersionen |
| DE3829001A1 (de) * | 1988-08-26 | 1990-07-05 | Trigon Chemie Gmbh | Asparaginsaeure-derivate und verfahren zu ihrer herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB817261A (en) * | 1955-02-02 | 1959-07-29 | Armour & Co | Diamine salts of n-substituted trimethylene diamine-n-alkanoic acids |
-
1968
- 1968-02-19 CH CH238768A patent/CH509267A/de not_active IP Right Cessation
-
1969
- 1969-02-04 GB GB1228735D patent/GB1228735A/en not_active Expired
- 1969-02-06 AT AT121969A patent/AT290489B/de active
- 1969-02-13 NL NL6902241A patent/NL6902241A/xx unknown
- 1969-02-13 DE DE19691907149 patent/DE1907149B2/de active Granted
- 1969-02-18 FR FR6903981A patent/FR2014111A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0022059A3 (en) * | 1979-05-08 | 1981-06-03 | Ciba-Geigy Ag | N-substituted esters of aspartic acid, their preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1907149A1 (de) | 1969-09-11 |
| GB1228735A (enrdf_load_stackoverflow) | 1971-04-15 |
| DE1907149C3 (enrdf_load_stackoverflow) | 1975-03-06 |
| CH509267A (de) | 1971-06-30 |
| FR2014111A1 (enrdf_load_stackoverflow) | 1970-04-17 |
| AT290489B (de) | 1971-06-11 |
| NL6902241A (enrdf_load_stackoverflow) | 1969-08-21 |
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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 |