Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)

Abstract

A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 g, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 g. Compared with the existing routes, this synthetic approach is operationally simple, goodyielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.

Structure, Synthesis, and Bioassays of Sex Pheromone for Pyrausta machaeralis (Lepidoptera: Crambidae)

“…As doses of pheromone (mixture of Z-12-tetradecenyl acetate and E-12tetradecenyl acetate) ranged from 1 to 1000 μg, the highest EAG response of Ostrinia furnacalis male was elicited by the dose of 10 μg, while the EAG amplitude slightly decreased when the dose of pheromone blends increased to 100 or 1000 μg. 43 However, the EAG responses still do not reveal the pheromone compounds that are attractive to males. Consequently, the activity of the E11-14:Ac or Z11-14:Ac mixture at different ratios was evaluated using a wind tunnel bioassay.…”

“…Besides, the EAG amplitudes to sex pheromones were generally limited by a maximum and minimum dosage threshold. As doses of pheromone (mixture of Z- 12-tetradecenyl acetate and E- 12-tetradecenyl acetate) ranged from 1 to 1000 μg, the highest EAG response of Ostrinia furnacalis male was elicited by the dose of 10 μg, while the EAG amplitude slightly decreased when the dose of pheromone blends increased to 100 or 1000 μg …”

Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022

“…): 42 , 47 Plutella xylostella (Lep., Plutellidae): 43 , 48 Trichoplusia ni (Lep., Noctuidae): 44 , 49 Tortrix viridana (Lep., Tortricidae): 45 , 50 Grapholita molesta , G. funebrana , and Hedya nubiferana (Lep., Tortricidae): ( E )- and ( Z )- 46 , 51 Plutella xylostella (Lep., Plutellidae): 47 , 52 moth (Lep.) 48–52 , 47 Keiferia lycopersicella (Lep., Gelechiidae): 53 , 53 Anthistarcha binocularis (Lep., Gelechiidae): 54 and 55 , 54 Illiberis pruni (Lep., Zygaenidae): 56 and 57 , 55 Rhyacionia buoliana (Lep., Tortricidae): 58 , 50 Phyllonorycter blancardella (Lep., Gracillariidae): ( Z )- 59 , 56 Ostrinia furnacalis (Lep., Crambidae): ( E )- and ( Z )- 60 , 57 Melanotus communis (Col., Elateridae): 61 , 58 Dasineura pyri (Dip., Cecidomyiidae): 62 , 59 Ithomia salapia (Lep., Nymphalidae): 63 and 64 , 60 Cydia pomonella (Lep., Tortricidae): 65 , 61,62 Stathmopoda masinissa (Lep., Stathmopodidae): 66 and 67 , 63 Lobesia botrana (Lep., Tortricidae): 68 , 64–66 Malacosoma neustria and Dendrolimus punctatus (Lep., Lasiocampidae): 69 , Spodoptera littoralis and S. litura (Lep., Noctuidae): 70 , 67 Thaumetopoea bonjeani (Lep., Notodontidae): 71 and 72 , 68 Acanthoscelides obtectus (Col., Chrysomelidae): 73 , 69 Plodia interpunctella hb. (Lep., Pyralidae): 74 , 70 Pectinophora gossypiella (Lep., Gelechiidae): 75 , 29,71 Spodoptera exigua (Lep., Noctuidae): 76 , 72 Phyllonorycter ringoniella (Lep., Gracillariidae): 77 , 73,74 Loepa sakaei (Lep., Saturniinae): 78 , 75 Symmetrischema tangolias (Lep., Gelechiidae): 79 , 76 Tuta absoluta (Lep., Gelechiidae):…”