DIOGO MONTES VIDAL IDENTIFICAÇÃO E SÍNTESE DOS ...

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ABSTRACT
Chapter I: The Poplar crop has gaining attention in the southern region of Brazil,
principally to supply the match industry and manufacturing matchsticks boxes. The poplar
moth Condylorrhiza vestigialis, is considered the major pest of this
culture. The defoliation caused by this Lepidoptera occurs on the higher phase of plant
grown, affecting seriously the production. The natural pheromone was extracted from
female pheromonal glands by the use of solvent extraction, between the 7 th and
10 th hours of scotophase. Y-olfactometer bioassays showed great attractiveness of males to
extracts with notable behavioral changing with exposure to natural compounds. The
electroantennographic activity of these compounds in male antennae was tested in GC-
EAD assays, and it was observed the presence of six possible pheromonal
components. The chemical structure of the compounds was studied by
analyzing their chromatographic profiles, mass (GC-MS) and infrared spectra (GC-
FTIR), as well as by analysis of microderivatizations products with 4-methyl-1,2,4-
triazolina-3 ,5-dione (MTAD), with DMDS and isomerization of double
bonds employing thiophenol. The spectroscopic and
chromatographic information obtained indicated that the compounds refer to aldehydes
belonging to the type I Lepidoptera pheromonal class and their structures were identified
as: E-hexadec-12-enal (1), (11E,14Z)-hexadeca-11 ,14-dienal (2), Z-hexadec-14-enal (3),
(10Z,12E)-hexadeca-10,12-dienal (4), (10E, 12Z)-hexadeca-10,12-dienal (5)
and (10E,12E)-hexadeca-10,12-dienal (6). The chemical structure of the compound 2 has
to be confirmed by its respective synthesis which is underway.
Chapter II: Brazil is one of the major soybean producers in the world. In the
piercing-sucking complex that occurs in soybean crops, Edessa meditabunda is considered
a secondary pest. The behavioral responses of males and females to aeration extracts from
conspecifics suggested the presence of a male sex pheromone. GC analyses of aeration
extracts released by males and females revealed the presence of two male-specific
compounds in a ratio of 92:8. GC-EAD assays indicated that the major component is
bioactive in females, supporting the bioassay data. Analysis of the mass and infrared
spectra of the male specific compounds suggested that they were both methyl branched
long chain methyl esters. The structure of these methyl esters were proposed based on the
mass spectra (EI) of the respective hydrocarbons obtained from microderivatizations, as