Synthesis of (7Z,9Z)-dodecadienyi acetate, a component of sex pheromones of the leafrollersEpinotia andEucosma, using conjugated diynols

Chrelashvili, Z. G.; Mavrov, M. V.; Уграк, Б. И.; Kutin, A. A.; Serebryakov, É. P.

doi:10.1007/bf00699203

Cited by 1 publication

(3 citation statements)

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“…This approach differs from previous reports starting from diynols 17 since it avoids the use of protecting groups and does not afford complex mixtures of stereoisomers. Using 2-pentynol (1) as starting material, it was developed a novel oxidation-olefination strategy to afford compound 4 in a rapid and efficient manner (Figure 1).…”

Section: Resultsmentioning

confidence: 89%

“…22 The presence of a J coupling of 10.7 Hz for the olefinic protons in the 1 H NMR of the major isomer of 4 confirmed the Z-stereochemical assignment, in agreement with previous reports. 17,23 For the reduction of the conjugated triple bond, the traditional Lindlar hydrogenation protocol 24,25 was not stereoselective, resulting in a mixture of geometrical isomers. Using instead activated Zn as the reducing agent 26 afforded the Z7,Z9-12:Ac isomer with complete stereoselectivity and 66% yield.…”

Section: Resultsmentioning

confidence: 99%

“…[28][29][30][31][32] Traps loaded with hexane (control) and the proportion 0:1 (OH:Ac) did not catch any males and were therefore not included in the statistical analysis. All the remaining treatments captured males, showing a population peak toward the end of the experiment (Figure 2A) blocks F 7,140 = 6.63, and treatments F 2,140 = 30.86; p < 0.0001.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and field evaluation of synthetic blends of the sex pheromone of Crocidosema aporema (Lepidoptera: Tortricidae) in soybean

González

Altesor

Alves

et al. 2012

J. Braz. Chem. Soc.

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Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae) é uma broca das axilas que se alimenta de soja e leguminosas forrageiras. Sua importância econômica é restrita à América do Sul onde pode alternar, ao longo do ano, entre leguminosas forrageiras e grãos. O feromônio sexual das fêmeas de C. aporema é composto de uma mistura 15:1 de (7Z,9Z)-dodeca-7,9-dieno-1-ol e acetato de (7Z,9Z)-dodeca-7,9-dienila. Com o intuito de desenvolver uma ferramenta para monitoramento deste inseto praga, os dois componentes do feromônio foram sintetizados e avaliou-se, em um experimento de campo no Uruguai, a captura de machos em armadilhas iscadas com diferentes misturas do feromônio sintético. Os dienos conjugados foram obtidos a partir de 2-pentin-1-ol e 1,7-heptanodiol, através da oxidação do primeiro, seguido pelo acoplamento de Wittig e redução da ligação tripla catalisada com Zn. A mistura 1:1 testada no campo foi a mais eficiente na captura dos machos. As armadilhas de feromônio foram atrativas por mais de 40 dias, mesmo com pequenas quantidades dos compostos (0,1 mg) impregnadas nos septos, e com baixas densidades populacionais dos insetos no campo.Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae) is a bud borer that feeds on soybean and forage legumes. Its economic importance is restricted to South America, where it can alternate throughout the year between forage and grain legumes. The sex pheromone of C. aporema females is composed of a 15:1 mixture of (7Z,9Z)-dodeca-7,9-dien-1-ol and (7Z,9Z)-dodeca-7,9-dienyl acetate. Aiming at the development of a monitoring tool, it was synthesized both components of the pheromone and evaluated male captures in pheromone traps baited with different blends of synthetic pheromone, in an experimental soybean field in Uruguay. The conjugated dienes were obtained from 2-pentyn-1-ol and 1,7-heptanediol, by oxidation of the former, Wittig coupling and Zn-catalyzed reduction of the triple bond. The 1:1 mixture was the most efficient in capturing males. The pheromone traps were attractive for up to 40 days, even with small septum loads (0.1 mg) and low population levels.Keywords: sex pheromone synthesis, Crocidosema (= Epinotia) aporema, pest monitoring, pheromone traps IntroductionSoybean production in Uruguay has increased dramatically in the past decade, 1 resulting in an expansion of legume-specialized insects such as Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae). This trend correlates with a significant increase in the use of insecticides, which has risen up to three-fold between 2001 and 2011. 2 C. aporema is a stem and bud borer that has become a major pest of legumes in Uruguay, Argentina, Chile and Southern Brazil.3-6 Originally from Costa Rica, this speciesSynthesis and Field Evaluation of Synthetic Blends of the Sex Pheromone of Crocidosema aporema J. Braz. Chem. Soc. 1998 is now widely distributed across South America. The insect is active throughout the year, going through 5-6 generations per year conce...

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Section: Resultsmentioning

confidence: 89%