CH393311A - Verfahren zur Herstellung von gereinigtes Pyrethrin enthaltenden Zusammensetzungen - Google Patents
Verfahren zur Herstellung von gereinigtes Pyrethrin enthaltenden ZusammensetzungenInfo
- Publication number
- CH393311A CH393311A CH247860A CH247860A CH393311A CH 393311 A CH393311 A CH 393311A CH 247860 A CH247860 A CH 247860A CH 247860 A CH247860 A CH 247860A CH 393311 A CH393311 A CH 393311A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyrethrin
- parts
- pyrethrins
- hydrocarbons
- cinerin
- Prior art date
Links
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 title claims description 58
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 title claims description 53
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 title claims description 51
- 239000000203 mixture Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 34
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 claims description 33
- VMORCWYWLVLMDG-YZGWKJHDSA-N Pyrethrin-II Natural products CC(=O)OC(=C[C@@H]1[C@H](C(=O)O[C@H]2CC(=O)C(=C2C)CC=CC=C)C1(C)C)C VMORCWYWLVLMDG-YZGWKJHDSA-N 0.000 claims description 29
- 239000007788 liquid Substances 0.000 claims description 28
- 239000000284 extract Substances 0.000 claims description 27
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 claims description 26
- 229940070846 pyrethrins Drugs 0.000 claims description 26
- 239000002728 pyrethroid Substances 0.000 claims description 26
- 240000004460 Tanacetum coccineum Species 0.000 claims description 19
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims description 19
- 229940015367 pyrethrum Drugs 0.000 claims description 19
- 229930193529 cinerin Natural products 0.000 claims description 16
- FMTFEIJHMMQUJI-UHFFFAOYSA-N Cinerin I Natural products C1C(=O)C(CC=CC)=C(C)C1OC(=O)C1C(C)(C)C1C=C(C)C FMTFEIJHMMQUJI-UHFFFAOYSA-N 0.000 claims description 14
- FMTFEIJHMMQUJI-DFKXKMKHSA-N cinerin I Chemical compound C1C(=O)C(C\C=C/C)=C(C)[C@H]1OC(=O)[C@H]1C(C)(C)[C@@H]1C=C(C)C FMTFEIJHMMQUJI-DFKXKMKHSA-N 0.000 claims description 14
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- LTNDZDRYUXNFCU-NEWSRXKRSA-N Cinerin II Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]2[C@@H](C=C(C)OC(=O)C)C2(C)C LTNDZDRYUXNFCU-NEWSRXKRSA-N 0.000 claims description 10
- SHCRDCOTRILILT-WOBDGSLYSA-N cinerin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C)C(=O)C1 SHCRDCOTRILILT-WOBDGSLYSA-N 0.000 claims description 10
- 239000008601 oleoresin Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003209 petroleum derivative Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 35
- 239000003921 oil Substances 0.000 description 25
- 239000012188 paraffin wax Substances 0.000 description 16
- 238000009835 boiling Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229940057995 liquid paraffin Drugs 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 241000196324 Embryophyta Species 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical group O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006103 coloring component Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- -1 pentadienyl chain Chemical group 0.000 description 1
- 229940048383 pyrethrum extract Drugs 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/16—Ericaceae [Heath or Blueberry family], e.g. rhododendron, arbutus, pieris, cranberry or bilberry
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7817/59A GB927892A (en) | 1959-03-06 | 1959-03-06 | Production of purified pyrethrum extract |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH393311A true CH393311A (de) | 1965-06-15 |
Family
ID=9840335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247860A CH393311A (de) | 1959-03-06 | 1960-03-04 | Verfahren zur Herstellung von gereinigtes Pyrethrin enthaltenden Zusammensetzungen |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE588295A (fr) |
| CH (1) | CH393311A (fr) |
| GB (1) | GB927892A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679662A (en) * | 1995-06-06 | 1997-10-21 | Thermo Trilogy Corporation | Synergistic use of azadirachtin and pyrethrum |
-
1959
- 1959-03-06 GB GB7817/59A patent/GB927892A/en not_active Expired
-
1960
- 1960-03-04 CH CH247860A patent/CH393311A/de unknown
- 1960-03-04 BE BE588295A patent/BE588295A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB927892A (en) | 1963-06-06 |
| BE588295A (fr) | 1960-09-05 |
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