MD4247B1 - Procedeu de sinteza a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. - Google Patents
Procedeu de sinteza a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. Download PDFInfo
- Publication number
- MD4247B1 MD4247B1 MDA20120126A MD20120126A MD4247B1 MD 4247 B1 MD4247 B1 MD 4247B1 MD A20120126 A MDA20120126 A MD A20120126A MD 20120126 A MD20120126 A MD 20120126A MD 4247 B1 MD4247 B1 MD 4247B1
- Authority
- MD
- Moldova
- Prior art keywords
- cis
- sex pheromone
- alcohol
- synthesis
- plum fruit
- Prior art date
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- 230000015572 biosynthetic process Effects 0.000 title abstract 6
- 238000003786 synthesis reaction Methods 0.000 title abstract 6
- 239000000877 Sex Attractant Substances 0.000 title abstract 4
- SUCYDSJQVVGOIW-WAYWQWQTSA-N 8Z-Dodecenyl acetate Chemical compound CCC\C=C/CCCCCCCOC(C)=O SUCYDSJQVVGOIW-WAYWQWQTSA-N 0.000 title abstract 3
- 241000923682 Grapholita funebrana Species 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 241000659076 Grapholitha Species 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- -1 acetylene alcohol Chemical compound 0.000 abstract 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 2
- 230000004071 biological effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 abstract 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 235000021018 plums Nutrition 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Inventia se refera la sinteza compusilor organici nesaturati, în special la sinteza feromonului sexual al viermelui prunelor, care se utilizeaza în protectia prunului.Esenta inventiei consta în aceea ca la interactiunea alcoolului propargilic cu 1-bromhexan în amoniac lichid se obtine compusul (1) nonin-2-ol-1 (v. schema de sinteza), care în prezenta amidurii de sodiu si etilendiamina se transforma în alcoolul acetilenic cu legatura tripla terminala nonin-8-ol-1 (2). Se protejeaza grupa hidroxilica în alcoolul (2) cu 2,3-dihidropiran cu formarea acetalului 1-(21-tetrahidropiraniloxi)-8-nonin (3), care în continuare se alchileaza cu bromura de propil în 1-(21-tetrahidropiraniloxi)-dodecin-8 (4). Dupa deprotejarea grupei hidroxilice (acid sulfuric de 16%, etanol) se obtine alcoolul acetilenic dodecin-8-ol-1 (5), reducerea caruia în prezenta catalizatorului de Ni cu etilendiamina în etanol duce la cis-8-dodecenol-1 (6). La acetilarea alcoolului (6) cu clorura de acetil în benzen, în prezenta piridinei, se obtine cis-8-dodecenilacetatul (7) - feromonul sexual al viermelui prunelor, care poseda o activitate biologica înalta în conditii de câmp.Schema de sinteza:HC≡CCH2OH → C6H13C≡CCH2OH (1) →HC≡C(CH2)7OH (2) → HC≡C(CH2)7OR (3, R = tetrahidropiranil) →C3H7C≡C(CH2)7OR (4) → C3H7C≡C(CH2)7OH (5) →cis-C3H7CH=CH(CH2)7OH (6) → cis-C3H7CH=CH(CH2)7OCOCH3 (7).Rezultatul tehnic consta în ieftinirea procesului de sinteza si obtinerea feromonului sexual cu puritate izomerica si activitate biologica la nivel cu etalonul.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4247B1 true MD4247B1 (ro) | 2013-08-31 |
| MD4247C1 MD4247C1 (ro) | 2014-03-31 |
Family
ID=49117532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4247C1 (ro) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109609609A (zh) * | 2019-01-25 | 2019-04-12 | 河北出入境检验检疫局检验检疫技术中心 | 一种李小食心虫的实时荧光pcr检测方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6486674A (en) * | 1973-01-30 | 1975-07-24 | Commw Scient Ind Res Org | Preparation of cis-8-dodecen-1-ol acetate |
| FR2317272A1 (fr) * | 1975-07-08 | 1977-02-04 | Procida | Nouveau procede de preparation des isomeres trans et cis de l'acetate de 8-dodecenyle et procede de lutte contre le cryptophlebia leucotreta utilisant ces produits comme attractifs |
| DE3726511A1 (de) * | 1987-08-08 | 1989-02-16 | Basf Ag | 1,1-dialkoxy- oder 1,1-((alpha),(omega)-methylendioxy)-non-2-in-9-ol und deren oh-geschuetzte derivate |
| JP2689319B2 (ja) * | 1995-02-24 | 1997-12-10 | 農林水産省蚕糸・昆虫農業技術研究所長 | キボシカミキリの性刺激剤 |
| US6838576B1 (en) * | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
-
2012
- 2012-10-19 MD MDA20120126A patent/MD4247C1/ro not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109609609A (zh) * | 2019-01-25 | 2019-04-12 | 河北出入境检验检疫局检验检疫技术中心 | 一种李小食心虫的实时荧光pcr检测方法 |
| CN109609609B (zh) * | 2019-01-25 | 2022-04-19 | 河北出入境检验检疫局检验检疫技术中心 | 一种李小食心虫的实时荧光pcr检测方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4247C1 (ro) | 2014-03-31 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |