Identifizierung und Synthese von Dimethylalkanen als Sexuallockstoffe weiblicher Miniermotten (Lyonetiidae) / Identification and Synthesis of Dimethylalkanes as Sex Attractants of Female Leaf Miner Moths (Lyonetiidae)

Francke, Wittko; Tóth, Miklós; Szöcs, Gábor; Krieg, Wolfgang; Ernst, Hansgeorg; Buschmann, Ernst

doi:10.1515/znc-1988-9-1025

Cited by 35 publications

(8 citation statements)

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“…L. monacha also secrets an unbranched derivative (epo7-18:H) [97], and a C 20 analog (Me2,epo7-20:H) has recently been found in females of another related species, L. xylina [98]. In addition to the epoxides, six methyl-branched hydrocarbons with a C 15 -C 18 main chain have been identified from four micro-lepidopteran species in Lyonetiidae (Yponomeutoidea) [99][100][101][102][103]. These Lyonetiidae pheromones possess one methyl group at the common 5-position, because the 14-position of 1,Me14-18:H and 1,Me10,Me14-18:H is represented as the 5-positon counting from the opposite terminal methyl group.…”

Section: Structures Of Other Female Pheromonesmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

332

289

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As a consequence of the diversity of Lepidoptera, including 150,000 described species, interesting species-specific sex pheromone systems are exhibited in this insect group. The quite varied pheromones, which have been identified from female moths of nearly 530 species from around the world, are classified into groups of Type I (75%), Type II (15%), and miscellaneous (10%), according to their chemical structures. Additionally, many pheromones produced by male moths and butterflies have been known. While new sex pheromones from about 70 lepidopteran species have been reported in the last five years utilizing GC-EAD, GC-MS, LC, and NMR, our information about the pheromones is still rudimentary, and these kinds of semiochemicals remain an exciting research target for natural product chemistry. In addition to the overview of their chemical structures, this chapter deals with current methods for their identification. Furthermore, an actual application of the synthetic pheromones for pest control is briefly introduced.

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Section: Structures Of Other Female Pheromonesmentioning

confidence: 99%

Lepidopteran Sex Pheromones

Ando

Inomata

Yamamoto

2004

Topics in Current Chemistry

332

289

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“…3 The sex pheromone was previously identified as 5,9-dimethylpentadecane (1). 4 Several aspects of pheromone biology may change significantly with age. In some species, most females initiate calling within 24 h of emergence, 5,6 while in other individuals vary considerably in the age at which calling starts.…”

Section: Introductionmentioning

confidence: 99%

Age and time related pheromone production in coffee leafminer Leucoptera coffeella Guérin-Méneville (Lepidoptera: Lyonetiidae)

Lima¹,

Vilela²,

Lúcia³

et al. 2008

J. Braz. Chem. Soc.

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Este estudo foi feito para determinar o padrão de produção de feromônio sexual em glândulas de fêmeas virgens de Leucoptera coffeella como uma medida indireta do comportamento de chamamento. O composto principal, 5,9-dimetilpentadecano (1) foi extraído de glândulas de feromônio de fêmeas virgens para ser usado em dois experimentos. No primeiro foi investigado o efeito do tempo na produção do feromônio (extratos de 10 fêmeas de dois dias de idade em intervalos de duas horas) e no outro foi avaliado o efeito da idade das fêmeas na produção de feromônio (10 fêmeas com idade entre 1 e 5 dias após a emergência). Os extratos hexânicos contendo 5 ng µL -1 de 5,9-dimetilheptadecano (2) como padrão interno foram analisados por CG. As fêmeas tiveram as maiores quantidades de feromônio nas últimas quatro horas da escotofase e nas duas primeiras horas da fotofase. Fêmeas de um dia de idade produziram as maiores quantidades de feromônio na glândula.This study was undertaken to access the pattern of sex pheromone production in glands of virgin females of Leucoptera coffeella as an indirect measure of the calling behavior. The major compound, 5,9-dimethylpentadecane (1) was extracted from pheromone glands of virgin females to be used in two experiments. The first one investigated the effect of the pheromone production time by females (extracts of 10 females with age of two days were carried out at 2-hour intervals). The other experiment evaluated the effect of female age on pheromone production (10 females with age ranged from 1 to 5 days after emergence class were used). Hexane extracts were made with 5 ng µL -1 of 5,9-dimethylheptadecane (2) as internal standard and analyzed by GC. Females had the highest amount of pheromone at the last four hours in the dark and the two first hours in the light period. One-day old females produced the highest amount of pheromone in the glands.Keywords: Leucoptera coffeella, Lepidoptera, sex pheromone, 5,9-dimethylpentadecane, pheromone titer, coffee leaf miner IntroductionCoffee leafminer (CLM) Leucoptera coffeella (Guérin-Méneville) is an important and widely distributed pest among the main coffee-producing countries in the Neotropical region. 1,2 In Brazil, it is considered a key pest of the coffee plant and causes losses up to 50% in production, due to the loss of photosynthetic area as a consequence of necrosis of the leaf surface, and early leaf fall when larval infestation is high. 2 The inclusion of CLM sex pheromone in programs of integrated pest management of coffee through population monitoring has been pointed out by Precetti and Parra. 3 The sex pheromone was previously identified as 5,9-dimethylpentadecane (1). 4 Several aspects of pheromone biology may change significantly with age. In some species, most females initiate calling within 24 h of emergence, 5,6 while in other individuals vary considerably in the age at which calling starts. 7,8 In several species, pheromone titer in the gland changes both with age and time during the scotophase or photophase. [9][10][11][12] To a...

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“…In 1988, Wittko Francke recognised that the main component of the sex attractant of females is 5,9-dimethylpentadecane. [188] Field studies with monitoring traps, which contained the different stereoisomers, revealed the (5S,9R)-isomer as the most active component. [189] For practical applications, the mixture of diastereomers can be used none the less.…”

Section: Coffee Leaf Minermentioning

confidence: 98%

Agrochemicals

Schaefer

2014

Natural Products in the Chemical Industry

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Identifizierung und Synthese von Dimethylalkanen als Sexuallockstoffe weiblicher Miniermotten (Lyonetiidae) / Identification and Synthesis of Dimethylalkanes as Sex Attractants of Female Leaf Miner Moths (Lyonetiidae)

Cited by 35 publications

References 0 publications

Lepidopteran Sex Pheromones

Lepidopteran Sex Pheromones

Age and time related pheromone production in coffee leafminer Leucoptera coffeella Guérin-Méneville (Lepidoptera: Lyonetiidae)

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