Female-Produced Sex Pheromone of Tetrastichus planipennisi, a Parasitoid Introduced for Biological Control of the Invasive Emerald Ash Borer, Agrilus planipennis

Sex pheromone communication in an insect parasitoid, Campoletis chlorideae Uchida

“…For instance, ( Z )-4-tridecenal, ( Z )-9-hexadecenal, and ( Z , Z )-9,12-octadecadienal have been reported as one sex pheromone component of Macrocentrus grandii (Braconidae) ( 59 ), Ascogaster reticulatus (Braconidae) ( 60 ), and A. quadridentata (Braconidae) ( 20 ), respectively. Moreover, methyl 6-methylsalicylate and (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene were identified as one sex pheromone component of Spalangia endius (Pteromalidae) ( 61 ) and Tetrastichus planipennisi (Eulophidae) ( 62 ), respectively. In this study, using comprehensive electrophysiological analyses and behavioral tests, we discovered that 14:Ald and 2-Hep comprise the volatile sex pheromone of C. chlorideae .…”

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

“…Chourreu et al (2020) reported a short and scalable synthesis of (8E,10Z)-tetradeca-8,10-dienal (123), the sex pheromone of the horse chestnut leaf miner moth Cameraria ohridella. 95 The natural product was obtained in 6 steps and 40% yield.…”

“…6) are pheromones of Alabama argillacea (Lep., Erebidae): (S)-136, 106 Neoclytus acuminatus acuminatus (Col., Cerambycidae): (S)-137 and (S)-138, 107 Cacopsylla pyricola (Hem., Psyllidae): 139, 108 Lyonetia prunifoliella (Lep., Lyonetiidae): (5S,9S)-140, 109 Galleria mellonella (Lep., Pyralidae): 141, 110,111 Leucoptera sinuella (Lep., Lyonetiidae): 142, 112 Eurytoma maslovskii (Hym., Eurytomidae): 143, 144, 145, 146, and 147, 113 Antitrogus parvulus (Col., Melolonthidae): 148, 114 Eurytoma maslovskii (Hym., Eurytomidae): 149 and 150, 110,111 Psacothea hilaris (Col., Cerambycidae): 151, 115 Lyonetia clerkella (Lep., Lyonetiidae): (S)-152, [116][117][118][119][120] Lyonetia prunifoliella (Lep., Lyonetiidae): (10S,14S)-153, 121 Trichogramma turkestanica (Hym., Trichogrammatidae): (2E,4E,6S,8S,10S)-154, 122 and Tetrastichus planipennisi (Hym., Eulophidae): 155. 123 Generally, methyl branching is introduced by (asymmetric) alkylation reactions (oen using Evans oxazolidinones) or by using a methyl-branched precursor such as citronellol, a natural product commonly used as a building-block for total synthesis. The enantioselective gram-scale synthesis of (R)-and (S)-13methylheptacosane (139), the sex pheromone of the pear psylla Cacopsylla pyricola was described by Yuan et al (2021) starting from tetradecanoic acid (Scheme 10).…”