A Convenient Method for the Synthesis of Insect Growth Regulators Cyclopentene Analogs of Alkyl (2E,4E)-Dodecadienoates

✍ Scribed by Novák, Lajos ;Rohály, János ;Gálik, György ;Fekete, Jenö ;Varjas, László ;Szántay, Csaba

• Book ID: 102902743
• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: English
• Weight: 977 KB
• Volume: 1986
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198619860309

✦ Synopsis

Starting with the aldehydes 7 and methyl vinyl ketone the title compounds 3a-d and their corresponding 2 2 isomers 16a -d are prepared in three steps: 1) thiazolium salt-catalyzed addition reaction to yield the diketone 8, 2) cyclocondensation reaction to give the corresponding cyclopentenone 11, and 3) Wittig-Horner reaction. This procedure is used to synthesize the 5-substituted 2,4-pentadienoates 3f-i and 16f-i. The results from pesticide screening are also reported.

Eine einfache

Synthesevorschrift fur lnsektenwachstumsregulatoren. -Cyclopenten-Analoge von (2E,4E)-Dodecadiensaureestern Ausgchend von den Aldehyden 7 und Methylvinylketon werden die Titelverbindungen 3a-d und deren entsprechende 2Z-lsomeren 16a -d in drei Stufen hergestellt: 1) Thiazoliumsalz-katalysierte Addition zu den Diketonen 8, 2) cyclisierende Aldolreaktion zu den entsprechenden Cyclopentenonen 11, 3) Wittig-Horner-Reaktion. Dadurch lieBen sich 5-substituierte 2,4-Pentadienoate aufbauen. Ferner werden die Ergebnisse von Pestizid-Eignungstests mitgeteilt.

Juvenoids represent a type of insect growth regulators. They are considered as novel, nontoxic, environmentally safe insecticides. The practical use of juvenoids is based upon their specific inhibitory action on morphogenesis accompanying insect metamorphosis. Thcy induce irreversible developmental disturbances during metamorphic moults leading to retarded mortality in treated population. Juvenoids are perspectivic for controlling insect pests in agriculture and forestry. Significant and notorious pests belonging to orders Homoptere and Lepidoptera should be mentioned as ideal targets. In addition, these selective compounds are also highly effective against some Diptera harmful for human and animal health ' p3)