HU184622B - Process for preparing 7/z/-dodecen-1-yl-acetate - Google Patents
Process for preparing 7/z/-dodecen-1-yl-acetate Download PDFInfo
- Publication number
- HU184622B HU184622B HU79EE2721A HUEE002721A HU184622B HU 184622 B HU184622 B HU 184622B HU 79EE2721 A HU79EE2721 A HU 79EE2721A HU EE002721 A HUEE002721 A HU EE002721A HU 184622 B HU184622 B HU 184622B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- dodecen
- acetate
- resulting
- reaction
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- MAAMIILYYYQTQW-SEYXRHQNSA-N [(z)-dodec-1-enyl] acetate Chemical compound CCCCCCCCCC\C=C/OC(C)=O MAAMIILYYYQTQW-SEYXRHQNSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 8
- -1 lithium aluminum hydride Chemical compound 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- CQKHFONAFZDDKV-QXMHVHEDSA-N (Z)-dodec-1-en-1-ol Chemical compound CCCCCCCCCC\C=C/O CQKHFONAFZDDKV-QXMHVHEDSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 8
- 241000218475 Agrotis segetum Species 0.000 abstract description 2
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 239000005667 attractant Substances 0.000 abstract 1
- 230000031902 chemoattractant activity Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000013011 mating Effects 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- BXRLUWIDTDLHQE-UHFFFAOYSA-N methyl 7-bromoheptanoate Chemical compound COC(=O)CCCCCCBr BXRLUWIDTDLHQE-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000877 Sex Attractant Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IRJUAJCYGORGMI-UHFFFAOYSA-M (7-methoxy-7-oxoheptyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC(=O)OC)C1=CC=CC=C1 IRJUAJCYGORGMI-UHFFFAOYSA-M 0.000 description 2
- IGNBKLCFKTYIRI-UHFFFAOYSA-N 7-chloroheptanoic acid Chemical compound OC(=O)CCCCCCCl IGNBKLCFKTYIRI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000252826 Brahmaea certhia Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JLPQXFFMVVPIRW-UHFFFAOYSA-N 7-bromoheptanoic acid Chemical compound OC(=O)CCCCCCBr JLPQXFFMVVPIRW-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- LDPLIHVYUJTDKY-UHFFFAOYSA-N [O-]C(=O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound [O-]C(=O)CCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 LDPLIHVYUJTDKY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- PAWGRNGPMLVJQH-KHPPLWFESA-N cis-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C/C(O)=O PAWGRNGPMLVJQH-KHPPLWFESA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PAWGRNGPMLVJQH-ZHACJKMWSA-N trans-2-dodecenoic acid Chemical compound CCCCCCCCC\C=C\C(O)=O PAWGRNGPMLVJQH-ZHACJKMWSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782893651A SU999973A3 (ru) | 1979-12-29 | 1978-12-28 | Способ получени производных пиридо (1,2-а) пиримидина или их фармацевтически приемлемых солей или их оптически активных изомеров |
| HU79EE2721A HU184622B (en) | 1979-12-29 | 1979-12-29 | Process for preparing 7/z/-dodecen-1-yl-acetate |
| DD80226261A DD155383A5 (de) | 1979-12-29 | 1980-12-18 | Lockstoffpraeparat |
| SE8008943A SE8008943L (sv) | 1979-12-29 | 1980-12-18 | Insektsattraherande komposition for vetejordfly och forfarande for framstellning av de aktiva ingredienserna deri |
| CS809198A CS226420B2 (en) | 1979-12-29 | 1980-12-22 | Insecticide agent |
| NL8006957A NL8006957A (nl) | 1979-12-29 | 1980-12-22 | Samengesteld insecten aantrekkend middel voor mannelijke scotia segetum en werkwijze voor de bereiding van de aktieve bestanddelen daarvan. |
| BE1/10086A BE886800A (fr) | 1979-12-29 | 1980-12-22 | Attractant composite d'insectes, pour les agrotis males a ligne blanche et procede de preparation des constituants actifs de cet attractant |
| DK553780A DK553780A (da) | 1979-12-29 | 1980-12-23 | Insektbekaempelsespraeparat |
| FR8027288A FR2472340A1 (fr) | 1979-12-29 | 1980-12-23 | Attractant composite d'insectes, pour les agrotis males a ligne blanche et procede de preparation des constituants actifs de cet attractant |
| FI804017A FI64736C (fi) | 1979-12-29 | 1980-12-23 | Insektsattraherande komposition foer hannar av saedesbroddfly och foerfarande foer framstaellning av dess aktiva komponenter |
| ES498615A ES8205744A1 (es) | 1979-12-29 | 1980-12-24 | Procedimiento de preparar agentes acetatico utiles para con-trolar plagas de insectos. |
| CH956580A CH646034A5 (de) | 1979-12-29 | 1980-12-24 | Lockstoffpraeparat und verfahren zur herstellung von dessen komponenten. |
| US06/220,113 US4364931A (en) | 1979-12-29 | 1980-12-24 | Composite insect attractant for male white-line dart moths and a process for preparing the active ingredients thereof |
| IT8026979A IT1195200B (it) | 1979-12-29 | 1980-12-29 | Attrattivo per insetti composito,per i maschi della nottuella delle messi,e procedimento per la preparazione degli ingredienti attivi di esso |
| PL1980228812A PL127039B1 (en) | 1979-12-29 | 1980-12-29 | Insects attracting agent |
| JP18941480A JPS56100701A (en) | 1979-12-29 | 1980-12-29 | Composite insect attractive agent* its use and its manufacture |
| DE19803049309 DE3049309A1 (de) | 1979-12-29 | 1980-12-29 | Lockstoffpraeparat und verfahren zur herstellung der wirkstoffe desselben |
| CA000367601A CA1167763A (en) | 1979-12-29 | 1980-12-29 | Composite insect attractant for male white-line dart moths and a process for preparing the active ingredients thereof |
| AT0632280A AT367600B (de) | 1979-12-29 | 1980-12-29 | Lockstoffpraeparat |
| GB8041437A GB2066666B (en) | 1979-12-29 | 1980-12-29 | Composite insect attractant for male white-line dart moths and a process for preparing the active ingredients thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2721A HU184622B (en) | 1979-12-29 | 1979-12-29 | Process for preparing 7/z/-dodecen-1-yl-acetate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184622B true HU184622B (en) | 1984-09-28 |
Family
ID=10995885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79EE2721A HU184622B (en) | 1979-12-29 | 1979-12-29 | Process for preparing 7/z/-dodecen-1-yl-acetate |
Country Status (20)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57139005A (en) * | 1981-02-19 | 1982-08-27 | Otsuka Pharmaceut Co Ltd | Composition disturbing communication between insect pests |
| HU187779B (en) * | 1982-08-10 | 1986-02-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Composition for enticing turnip moth males |
| GR860221B (en) * | 1985-02-15 | 1986-05-22 | Basf Ag | Vineyards insecticidal means and method therefor |
| US4837358A (en) * | 1986-02-26 | 1989-06-06 | Phillips Petroleum Company | Preparation of 9-alkenyl ester compounds |
| US4696676A (en) * | 1986-06-27 | 1987-09-29 | International Flavors & Fragrances Inc. | Use of 1-nonen-3-ol for repelling insects |
| US4693890A (en) * | 1986-06-27 | 1987-09-15 | International Flavors & Fragrances Inc. | Use of 1-nonen-3-ol for repelling insects |
| US4759228A (en) * | 1987-01-09 | 1988-07-26 | International Flavors & Fragrances Inc. | Process for determination of repellency and attractancy |
| US4940831A (en) * | 1989-02-15 | 1990-07-10 | Phillips Petroleum Company | Purification of cis-olefins |
| WO1992009199A1 (en) * | 1990-11-23 | 1992-06-11 | Kansas State University Research Foundation | Method of attracting male hessian flies |
| CN107836450A (zh) * | 2017-11-06 | 2018-03-27 | 中国农业科学院植物保护研究所 | 一种大地老虎性诱剂的制备方法及应用 |
-
1978
- 1978-12-28 SU SU782893651A patent/SU999973A3/ru active
-
1979
- 1979-12-29 HU HU79EE2721A patent/HU184622B/hu unknown
-
1980
- 1980-12-18 DD DD80226261A patent/DD155383A5/de unknown
- 1980-12-18 SE SE8008943A patent/SE8008943L/xx not_active Application Discontinuation
- 1980-12-22 NL NL8006957A patent/NL8006957A/nl not_active Application Discontinuation
- 1980-12-22 BE BE1/10086A patent/BE886800A/fr not_active IP Right Cessation
- 1980-12-22 CS CS809198A patent/CS226420B2/cs unknown
- 1980-12-23 FI FI804017A patent/FI64736C/fi not_active IP Right Cessation
- 1980-12-23 DK DK553780A patent/DK553780A/da not_active Application Discontinuation
- 1980-12-23 FR FR8027288A patent/FR2472340A1/fr active Granted
- 1980-12-24 US US06/220,113 patent/US4364931A/en not_active Expired - Lifetime
- 1980-12-24 CH CH956580A patent/CH646034A5/de not_active IP Right Cessation
- 1980-12-24 ES ES498615A patent/ES8205744A1/es not_active Expired
- 1980-12-29 DE DE19803049309 patent/DE3049309A1/de not_active Withdrawn
- 1980-12-29 IT IT8026979A patent/IT1195200B/it active
- 1980-12-29 GB GB8041437A patent/GB2066666B/en not_active Expired
- 1980-12-29 PL PL1980228812A patent/PL127039B1/pl unknown
- 1980-12-29 JP JP18941480A patent/JPS56100701A/ja active Pending
- 1980-12-29 CA CA000367601A patent/CA1167763A/en not_active Expired
- 1980-12-29 AT AT0632280A patent/AT367600B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL127039B1 (en) | 1983-09-30 |
| PL228812A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-12-11 |
| FI804017L (fi) | 1981-06-30 |
| GB2066666A (en) | 1981-07-15 |
| GB2066666B (en) | 1983-08-17 |
| FR2472340A1 (fr) | 1981-07-03 |
| ES498615A0 (es) | 1982-07-01 |
| IT8026979A0 (it) | 1980-12-29 |
| ES8205744A1 (es) | 1982-07-01 |
| SE8008943L (sv) | 1981-06-30 |
| SU999973A3 (ru) | 1983-02-23 |
| CH646034A5 (de) | 1984-11-15 |
| BE886800A (fr) | 1981-06-22 |
| FI64736C (fi) | 1984-01-10 |
| CA1167763A (en) | 1984-05-22 |
| FR2472340B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-01-27 |
| CS226420B2 (en) | 1984-03-19 |
| ATA632280A (de) | 1981-12-15 |
| DD155383A5 (de) | 1982-06-09 |
| IT1195200B (it) | 1988-10-12 |
| JPS56100701A (en) | 1981-08-12 |
| US4364931A (en) | 1982-12-21 |
| AT367600B (de) | 1982-07-12 |
| NL8006957A (nl) | 1981-08-03 |
| DE3049309A1 (de) | 1981-09-17 |
| FI64736B (fi) | 1983-09-30 |
| DK553780A (da) | 1981-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |