MD4247C1 - Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. - Google Patents

Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr.

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Publication number
MD4247C1
MD4247C1 MDA20120126A MD20120126A MD4247C1 MD 4247 C1 MD4247 C1 MD 4247C1 MD A20120126 A MDA20120126 A MD A20120126A MD 20120126 A MD20120126 A MD 20120126A MD 4247 C1 MD4247 C1 MD 4247C1
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MD
Moldova
Prior art keywords
cis
sex pheromone
alcohol
synthesis
plum fruit
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MDA20120126A
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English (en)
Russian (ru)
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MD4247B1 (ro
Inventor
Георге РОШКА
Василиса ОДОБЕСКУ
Тудор НАСТАС
Дина ЕЛИСОВЕЦКАЯ
Original Assignee
Институт По Защите Растений И Экологического Сельского Хозяйства Анм
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Priority to MDA20120126A priority Critical patent/MD4247C1/ro
Publication of MD4247B1 publication Critical patent/MD4247B1/ro
Publication of MD4247C1 publication Critical patent/MD4247C1/ro

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Invenţia se referă la sinteza compuşilor organici nesaturaţi, în special la sinteza feromonului sexual al viermelui prunelor, care se utilizează în protecţia prunului.Esenţa invenţiei constă în aceea că la interacţiunea alcoolului propargilic cu 1-bromhexan în amoniac lichid se obţine compusul (1) nonin-2-ol-1 (v. schema de sinteză), care în prezenţa amidurii de sodiu şi etilendiamină se transformă în alcoolul acetilenic cu legătura triplă terminală nonin-8-ol-1 (2). Se protejează grupa hidroxilică în alcoolul (2) cu 2,3-dihidropiran cu formarea acetalului 1-(21-tetrahidropiraniloxi)-8-nonin (3), care în continuare se alchilează cu bromură de propil în 1-(21-tetrahidropiraniloxi)-dodecin-8 (4). După deprotejarea grupei hidroxilice (acid sulfuric de 16%, etanol) se obţine alcoolul acetilenic dodecin-8-ol-1 (5), reducerea căruia în prezenţa catalizatorului de Ni cu etilendiamină în etanol duce la cis-8-dodecenol-1 (6). La acetilarea alcoolului (6) cu clorură de acetil în benzen, în prezenţa piridinei, se obţine cis-8-dodecenilacetatul (7) - feromonul sexual al viermelui prunelor, care posedă o activitate biologică înaltă în condiţii de câmp.Schema de sinteză: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 constă în ieftinirea procesului de sinteză şi obţinerea feromonului sexual cu puritate izomerică şi activitate biologică la nivel cu etalonul.
MDA20120126A 2012-10-19 2012-10-19 Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. MD4247C1 (ro)

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MDA20120126A MD4247C1 (ro) 2012-10-19 2012-10-19 Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr.

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MDA20120126A MD4247C1 (ro) 2012-10-19 2012-10-19 Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr.

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MD4247B1 MD4247B1 (ro) 2013-08-31
MD4247C1 true MD4247C1 (ro) 2014-03-31

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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

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3906035A (en) * 1973-01-30 1975-09-16 Commw Scient Ind Res Org Process for the preparation of cis-8-dodecen-1-ol acetate
GB1504077A (en) * 1975-07-08 1978-03-15 Procida Method for controlling cryptophlebia leucotreta using dodecenyl acetate
US4877891A (en) * 1987-08-08 1989-10-31 Basf Aktiengesellschaft 1,1-dialkoxy- or 1,1-(alpha, omega-methylenedioxy)-non-2-yn-9-01 and their OH-protected derivatives
JPH08231304A (ja) * 1995-02-24 1996-09-10 Norin Suisansyo Sanshi Konchu Nogyo Gijutsu Kenkyusho 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

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3906035A (en) * 1973-01-30 1975-09-16 Commw Scient Ind Res Org Process for the preparation of cis-8-dodecen-1-ol acetate
GB1504077A (en) * 1975-07-08 1978-03-15 Procida Method for controlling cryptophlebia leucotreta using dodecenyl acetate
US4877891A (en) * 1987-08-08 1989-10-31 Basf Aktiengesellschaft 1,1-dialkoxy- or 1,1-(alpha, omega-methylenedioxy)-non-2-yn-9-01 and their OH-protected derivatives
JPH08231304A (ja) * 1995-02-24 1996-09-10 Norin Suisansyo Sanshi Konchu Nogyo Gijutsu Kenkyusho 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

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Holan G. and O,Keefe D.F. An improved synthesis of insect sex attractant: cis-8-dodecen-1-ol acetate. Tetrahedron Letters, No 9, pp. 673-674, 1973 *
Kenji Mori and Takuya Tashiro. Useful reactions in Modern Pheromone Synthesis. Current Organic Synthesis, 2004, 1, 11-29, Regăsit în Internet la 2013.06.24, url: http://benthamscience.com/cos/sample/cos1-1/Mori.pdf *
Kenji Mori. The Synthesis of Insect Pheromones, in The Total Synthesis of Natural Products, Vol. 4, 1981. Edited by John ApSimer vezi pag. 6, 9-10, 25-26 *
Одиноков В.Н., Ишмуратов Г.Ю., Балезина Г.Г., Толстиков Г.А. Феромоны насекомых и их аналоги. ХIII. Синтез (Е)- и (Z)-8-додеценилацетатов - компонентов половых феромонов Grapholitha funebrana и Grapholitha molesta. Химия природных соединений, № 3, с. 398-400, 1985 *

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