{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,25]],"date-time":"2026-07-25T22:25:52Z","timestamp":1785018352602,"version":"3.55.0"},"reference-count":92,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2019,9,27]],"date-time":"2019-09-27T00:00:00Z","timestamp":1569542400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Insects"],"abstract":"<jats:p>Knowledge of buprestid chemical ecology is sparse but the appearance of the invasive pest Agrilus planipennis Fairmaire in North America has provided the impetus to study in detail the semiochemistry and ecology of this important buprestid. The macrocyclic lactone (3Z)-12-dodecenolide [(3Z)-lactone] is identified as a key antennally-active compound that is produced by females and attracts males. Though a weak trap attractant alone, when combined with the host kairomone (3Z)-hexenol and the important visual cue of a green canopy trap, significant increases in male trap capture occur, thus defining (3Z)-lactone as both a sex pheromone of A. planipennis as well as the first and only known buprestid pheromone. The non-natural stereoisomer (3E)-12-dodecenolide and the saturated analog, 12-dodecanolide also exhibit mimetic activities towards male A. planipennis, suggesting a notable plasticity in this pheromonal structural motif. Efficient synthetic routes to these compounds have been developed. A series of fluoro-12-dodecanolides has also been synthesized containing CF2 groups as a strategy to bias the conformational space accessed by these macrolides and to assess if the analogs may act as mimetics for 12-dodecanolide pheromones associated in A. planipennis. These compounds also afford a unique opportunity to study the binding affinities of lactone surrogates with A. planipennis chemosensory proteins and olfactory receptors. Some progress has also been made in identifying the genes involved in the reception, processing and degradation of volatiles in this invasive insect. It is now evident that the behavior and ecology of A. planipennis involves a complex pattern of sensory modalities, including visual, tactile, olfactory and potentially acoustic components. Earlier reviews focused on studies of attractive host volatiles in development of a trapping system for early detection and visual and contact phenomena in A. planipennis mate finding. This review will update the semiochemistry and chemical ecology of A. planipennis and discuss studies on chemistry and behavior that have identified female-produced pheromone components and host kairomones.<\/jats:p>","DOI":"10.3390\/insects10100323","type":"journal-article","created":{"date-parts":[[2019,9,27]],"date-time":"2019-09-27T11:14:35Z","timestamp":1569582875000},"page":"323","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Semiochemical and Communication Ecology of the Emerald Ash Borer, Agrilus planipennis (Coleoptera: Buprestidae)"],"prefix":"10.3390","volume":"10","author":[{"given":"Peter","family":"Silk","sequence":"first","affiliation":[{"name":"Natural Resources Canada, Canadian Forest Service\u2014Atlantic Forestry Centre, 1350 Regent Street, Fredericton, NB E3B 5P7, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Mayo","sequence":"additional","affiliation":[{"name":"Natural Resources Canada, Canadian Forest Service\u2014Atlantic Forestry Centre, 1350 Regent Street, Fredericton, NB E3B 5P7, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Krista","family":"Ryall","sequence":"additional","affiliation":[{"name":"Natural Resources Canada, Canadian Forest Service\u2014Great Lakes Forestry Centre, 1219 Queen Street East, Sault Ste. Marie, ON P6A 2E5, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucas","family":"Roscoe","sequence":"additional","affiliation":[{"name":"Natural Resources Canada, Canadian Forest Service\u2014Atlantic Forestry Centre, 1350 Regent Street, Fredericton, NB E3B 5P7, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,9,27]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"The emerald ash borer: A new exotic pest in North America","volume":"47","author":"Haack","year":"2002","journal-title":"Newsl. Mich. Entomol. Soc."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1111\/j.1440-6055.1983.tb01846.x","article-title":"Beetles on the bottle: Male buprestids mistake stubbies for females (Coleoptera)","volume":"22","author":"Gwynne","year":"1983","journal-title":"Aust. J. 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