Semiochemical and Communication Ecology of the Emerald Ash Borer, Agrilus planipennis (Coleoptera: Buprestidae)
Abstract
:1. Background
2. Visual Cues
3. Host Kairomones
3.1. Bark Sesquiterpenes
3.2. Foliar Volatiles
4. The Natural Female-Produced Sex Pheromone
5. Contact Chemoreception
6. Acoustics
7. Progress in Identifying Odor Processing Genes in EAB
8. Semiochemistry of EAB Parasitoids
9. Development of EAB Detection Tools
9.1. Trap Development
9.2. Effective Range of the Trap
9.3. Mechanism of Pheromonal Activity
10. Attractants for Other Agrilus Species
11. Pheromone Analogs
11.1. Macrocycle Isomers
11.2. Macrocyclic Fluoro Analogs
12. Synthetic Chemistry of EAB Macrolides
12.1. Synthesis of (3Z)-12-Dodecenolide 2
- 1. O3, CH2Cl2, −78 °C. 2. PPh3, −78 °C—RT, 93%.
- 13 + Sodium bis(trimethylsilyl)amide, tetrahydrofuran (THF) and toluene, 0 °C—RT, then 12, −99 °C—RT, 90% yield, 98% Z-selectivity.
- TsOH, wet THF, reflux.
- NaClO2, H2NSO3H, 1-methyl-1-cyclohexene, CH2Cl2, H2O, 0 °C—RT, 70% over 2 steps.
- diisopropylazodicarboxylate (DIAD) or diethylazodicarboxylate (DEAD), PPh3, toluene, RT, 64% with DIAD; overall yield = 37% over 6 steps.
12.2. Synthesis of (3E)-12-Dodecenolide 3
- 1. NaH, DMF, 0 °C–90 °C. 2. 3-chloropropionaldehyde diethylacetal 18, NaI, 90 °C, 76%.
- (NH4)6Mo7O24·4H2O, H2O2, EtOH, RT, 73%.
- 1. Potassium bis(trimethylsilyl)amide, dimethyoxyethane (DME), −56 °C, then 12, −56 °C—RT, 60% yield, 97% E-selectivity.
- TsOH, wet THF, reflux.
- NaClO2, H2NSO3H, 1-methyl-1-cyclohexene, CH2Cl2, H2O, 0 °C—RT, 60% over 2 steps.
- DIAD or DEAD, PPh3, toluene, RT, 82% with DIAD; overall yield = 16% over 6 steps.
12.3. Synthesis of (3Z)- and (3E)-12-Dodecenolide Mixture (2 and 3)
- 2 equiv. sodium bis(trimethylsilyl)amide, THF, 0 °C—RT, then 25a, 25b or 12, −78 °C—RT, 70%, 67% and 61% yields, respectively and 2:1 Z/E in all 3 cases.
- For 25a and 25b, K2CO3, KI (only for 25a), acetone, reflux, 82% and 72% yields, respectively, 2:1 2:3 (Z:E) for both 26a and 26b.
- 1. O3, CH2Cl2, −78 °C. 2. PPh3, −78 °C—RT, 100% yield for 25a and 93% for 25b.
- HCl, H2O, THF, RT, 100%.
- DIAD, PPh3, toluene, RT, 84% combined yield of 2 and 3, ~5% 28. 2:3 = 2:1.
- CBr4, PPh3, CH2Cl2, 0 °C, 100%.
- I2, PPh3, imidazole, 1:3 CH3CN/Et2O, RT, 100%.
12.4. Synthesis of Saturated Lactone Analog, 12-Dodecanolide 4
- 2.1 equiv. mCPBA, 0.04 equiv. TsOH·H2O, CH2Cl2, RT, 87%.
- 10 equiv. mCPBA, 2 equiv. NaHCO3, CH2Cl2, RT, 59%.
- 10 equiv. H2O2 (35 wt% aqueous), 31 equiv. (CF3CO)2, 1 equiv. Na2HPO4·7H2O, CH2Cl2, RT, 72%.
- Permaleic acid 30 (generated in situ from maleic anhydride, 35 wt% aqueous H2O2 and acetic anhydride), CH2Cl2, RT, 75%.
13. Future Directions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Silk, P.; Mayo, P.; Ryall, K.; Roscoe, L. Semiochemical and Communication Ecology of the Emerald Ash Borer, Agrilus planipennis (Coleoptera: Buprestidae). Insects 2019, 10, 323. https://doi.org/10.3390/insects10100323
Silk P, Mayo P, Ryall K, Roscoe L. Semiochemical and Communication Ecology of the Emerald Ash Borer, Agrilus planipennis (Coleoptera: Buprestidae). Insects. 2019; 10(10):323. https://doi.org/10.3390/insects10100323
Chicago/Turabian StyleSilk, Peter, Peter Mayo, Krista Ryall, and Lucas Roscoe. 2019. "Semiochemical and Communication Ecology of the Emerald Ash Borer, Agrilus planipennis (Coleoptera: Buprestidae)" Insects 10, no. 10: 323. https://doi.org/10.3390/insects10100323