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ChemInform Abstract: STRUCTURE AND SYNTHESIS OF THE WING GLAND PHEROMONE OF THE MALE AFRICAN SUGAR-CANE BORER: ELDANA SACCHARINA (WLK.) (LEPIDOPTERA, PYRALIDAE)
Abstract
Aus dem 2-Butenl-ol (I) erhält man mit Orthoester den Alken-carbonsäureester (III), der mit Peroxid ein Epoxid (IV) liefert, das mit dem Lithium-cuprat (V) zum Tetrahydrofuranon (VI) in Form der beiden Stereoisomeren kondensiert wird und dessen trans-Form mit dem gesuchten Pheromon identisch ist.
... Decane-4-olide, undecane-4-olide, tetradecane-4-olide, and dodecane-5-olide are not known from other insect glands where similar lactones with isolated penta-and hexacyclic rings have a very limited distribution. 7-Lactones are known as pheromones from Trogoderma glabrum (hexane-4-olide;Yarger et al., 1975), Popilliajaponica (5tetradecene-4-olide; Tumlinson, 1979), Lasiusflavus (9-octadecene-4-olide, 9-hexadecene-4-olide, function unknown; Bergstr~m and L6fquist, 1970), and Eldana saccharina (3,7-dimethyl-6-octene-4-olide; Kunesch et al., 1981). 6-Lactones were found in the mandibular gland secretions of Xylocopa hirsutissima (2-methyl-hexane-5-olide;Wheeler et al., 1976) and two Camponotus species (2-decene-5-olide; Cavill et al., 1968). ...
The secretions of the abdominal glands ofBledius spectabilis Kraatz,Platystethus arenarius Fourcr., andOxytelus piceus L. have been shown to contain four 1-alkenes; toluquinone; toluhydroquinone; C10 (-)-,C11 (-), C12 (-)-, and C14 (-) γ-lactones; C12-δ-lactone; citral; and decyl-, undecyl-, and dodecyl acetates. Quantitative results indicate that 1-alkenes are formed probably from present lactones by decarboxylation. According to the known life histories of the beetles, it is suggested that the gland material is not used as an algal growth regulator but represents a unique defensive blend characteristic for the whole subfamily.
... 6-Methyl-5-hepten-2-one and the corresponding alcohol were found in the abdominal brushes of the noctuid, Phlogophora meticulosa (Aplin and Birch, 1970), and pinocarvone in the brushes of another noctuid, Apamea monoglypha (Aplin and Birch, 1970). More notably, the monoterpene lactone (3S, 4R)-trans-3,7-dimethyl-6-octen-4-olide, is produced in the wing glands of the male galleriid, Eldana saccharina (Kunesch et al., 1981;Vigneron et al., 1982), and the diterpene, (E)-3,7,t 1,15-tetramethyl-2-hexadecen-1ol [(E)-phytol], is produced in the wing glands of the male phycitid, Ephestia elutella (Phelan et al., 1986). ...
Behavioral observations of the rice moth (Corcyra cephalonica, Pyralidae, Galleriinae) in the laboratory have shown that a male wing-gland pheromone induces attraction of female moths. This pheromone was identified as a blend of (E,E) and (Z,E)-farnesal. Wing-gland extracts or synthetic compounds were shown to be attractive to females by inducing walking.
... Eldanolide [(3S,4R)-3,7-dimethyl-6-octen-4-olide, (39)] is a male-produced monoterpenoid sex attractant for the African sugarcane stem borer Eldana sacharina [104]. ...
The synthesis of insect pheromones published in the period 2005-2007 is reviewed. A total of 66 compounds from different insect orders and belonging to different structural classes were included.
The term “pheromones,” in general, refers to chemical substances, which when produced and released to the outside by an individual cause specific behavioral or physiological responses in other individuals of the same species. Ever since the sex pheromone of the silkmoth, Bombyx mori, was reported as the first chemically identified pheromone nearly 30 years ago (Butenandt et al. 1959), considerable research has been conducted on pheromones in insect species.
The wing gland secretion in teh male pyralid moth Achroid innotata obscurevittella RAGONOT consisted of 2 components, which were identified as nonanol and nonanal. Nonanol (96.8%) was present as a major component responsible for sexual attractancy of the virgin female moth, while nonanal (3.2%) was a minor component and indicated no activity alone. © 1990, JAPANESE SOCIETY OF APPLIED ENTOMOLOGY AND ZOOLOGY. All rights reserved.
The molecular structures of insect sex pheromones are quite diverse. They vary from the very simple straight-chain alcohols, acetates, and aldehydes that are predominant in the repertory of lepidopteran sexual communication to the more elaborate isoprenoids employed by scale insects. Synthesis of the simpler pheromones has been concerned primarily with chain elongation and the establishment of the required geometry about one or more double bonds. The more varied fare of other insect pheromones has focused considerable attention on their three-dimensional nature.
Besides optical, acoustical and tactile stimuli, living organisms use chemical cues for the transmission of information. Chemotaxis is a general archaic principle, and a wide range of living beings, microorganisms as well as primates, are capable of releasing compounds (‘semiochemicals’) which are used in intraspecific and interspecific chemical communication.
The two major components of the female sex pheromones of twoCreatonotos species have been identified as an achiral C21 triene, (Z,Z,Z)-3,6,9-heneicosatriene, and a chiral epoxide, (Z,Z)-2(2,5-octadienyl)-3-undecyloxirane. The ratios of these components in the two species fall into nonoverlapping ranges. Two additional achiral minor components, (Z,Z)-6,9-heneicosadiene and (Z,Z,Z)-3,6,9-tricosatriene, were also identified in the female sex gland extracts. The male pheromone of both species consists of hydroxydanaidal, a chiral dihydropyrrolizine derived from pyrrolizidine alkaloids in the larval diet.Creatonotos transiens was found to convert dietary heliotrine into (R)-(-)-hydroxydanaidal, with inversion at the single asymmetric carbon atom. The possible biological and biosynthetic significance of the chiral pheromone components are discussed, and they are compared with known examples of chiral lepidopteran pheromones.
The structure of the sex attractant isolated from the wing glands of has been determined by chemical and physical methods as -3-methyl-4-dimethylallyl- γ -lactone . The synthesis of racemic is described.