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Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis

Herbert, Myles B. and Marx, Vanessa M. and Pederson, Richard L. and Grubbs, Robert H. (2013) Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis. Angewandte Chemie International Edition, 52 (1). pp. 310-314. ISSN 1433-7851. PMCID PMC3789658. doi:10.1002/anie.201206079. https://resolver.caltech.edu/CaltechAUTHORS:20130215-105939642

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Abstract

The use of insect sex pheromones to limit specifically targeted pest populations has gained increasing popularity as a viable, safe, and environmentally friendly alternative to insecticides. While broad-spectrum insecticides are toxic compounds that have been shown to adversely affect human health,[1] extensive studies have shown that insect pheromones are nontoxic and safe for human consumption at the levels used in pest control practices.[2] Female sex pheromones are mainly employed in pest control in a process termed mating disruption. This involves dispersing pheromones over a large area, overloading the sensory organs of male insects and preventing them from locating and mating with females who are releasing a much smaller amount of the same pheromone blends; this strategy has proven to reduce specific insect populations dramatically.[3] To date, the United States Environmental Protection Agency (EPA) has approved approximately twenty lepidopteran female sex pheromones as active ingredients for pest control.[2]


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201206079DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201206079/abstractPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3789658/PubMed CentralArticle
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: July 30, 2012, Published online: October 10, 2012. Dr. David VanderVelde is thanked for his assistance with NMR characterization and experiments. Zachary K. Wickens and Dr. Daryl P. Allen are thanked for helpful discussion related to pheromone synthesis. This work was financially supported by the NIH (NIH 5R01GM031332-27), the NSF (CHE-1048404), and NSERC (fellowship to V.M.M.). Materia Inc. is acknowledged for the generous donation of metathesis catalyst 1. Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/anie.201206079.
Funders:
Funding AgencyGrant Number
NIH5R01GM031332-27
NSFCHE-1048404
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Subject Keywords:insect pheromones; metathesis; ruthenium; seed-oil derivatives; unconjugated dienes
Issue or Number:1
PubMed Central ID:PMC3789658
DOI:10.1002/anie.201206079
Record Number:CaltechAUTHORS:20130215-105939642
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130215-105939642
Official Citation:Herbert, M. B., Marx, V. M., Pederson, R. L. and Grubbs, R. H. (2013), Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis . Angew. Chem. Int. Ed., 52: 310–314. doi: 10.1002/anie.201206079
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:36953
Collection:CaltechAUTHORS
Deposited By: Donna Wrublewski
Deposited On:15 Feb 2013 19:39
Last Modified:09 Nov 2021 23:25

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