Cargando…

Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests

Benzyl methyl ester, also known as methyl benzoate (MB), is a volatile organic compound that exists naturally as a floral fragrance in many plants. Our behavioral bioassays show that MB and some of its naturally occurring and synthetic analogs kill insects at different life stages. Compared to comme...

Descripción completa

Detalles Bibliográficos
Autores principales: Feng, Yan, Chen, Jian, Zhang, Aijun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5962541/
https://www.ncbi.nlm.nih.gov/pubmed/29784959
http://dx.doi.org/10.1038/s41598-018-26242-6
_version_ 1783324884947959808
author Feng, Yan
Chen, Jian
Zhang, Aijun
author_facet Feng, Yan
Chen, Jian
Zhang, Aijun
author_sort Feng, Yan
collection PubMed
description Benzyl methyl ester, also known as methyl benzoate (MB), is a volatile organic compound that exists naturally as a floral fragrance in many plants. Our behavioral bioassays show that MB and some of its naturally occurring and synthetic analogs kill insects at different life stages. Compared to commercial pesticides containing pyriproxyfen and acetamiprid, MB and some analogs are 1.3 to 3.4 times more toxic to gypsy moth larvae and brown marmorated stinkbug nymphs. The arthropod repellent DEET is also a benzyl ester, and shares the same chemical skeleton with MB. They differ by the diethylamide ester and a methyl group on the benzene ring in DEET. However, unlike MB, DEET does not kill insects; instead, it deters or repels them. Exactly how DEET causes the repellent effect in target organisms is still a mystery. Due to the MB’s structural similarity to DEET, exploring the structure – activity relationship (SAR) of the MB analogs will provide useful information for the discovery of the mode and mechanistic actions of DEET as an insect repellent. In addition, the SAR will allow researchers to modify the chemical structure of the MB molecule, leading to the development of more efficient, safe, and environmentally – friendly green pesticides.
format Online
Article
Text
id pubmed-5962541
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-59625412018-05-24 Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests Feng, Yan Chen, Jian Zhang, Aijun Sci Rep Article Benzyl methyl ester, also known as methyl benzoate (MB), is a volatile organic compound that exists naturally as a floral fragrance in many plants. Our behavioral bioassays show that MB and some of its naturally occurring and synthetic analogs kill insects at different life stages. Compared to commercial pesticides containing pyriproxyfen and acetamiprid, MB and some analogs are 1.3 to 3.4 times more toxic to gypsy moth larvae and brown marmorated stinkbug nymphs. The arthropod repellent DEET is also a benzyl ester, and shares the same chemical skeleton with MB. They differ by the diethylamide ester and a methyl group on the benzene ring in DEET. However, unlike MB, DEET does not kill insects; instead, it deters or repels them. Exactly how DEET causes the repellent effect in target organisms is still a mystery. Due to the MB’s structural similarity to DEET, exploring the structure – activity relationship (SAR) of the MB analogs will provide useful information for the discovery of the mode and mechanistic actions of DEET as an insect repellent. In addition, the SAR will allow researchers to modify the chemical structure of the MB molecule, leading to the development of more efficient, safe, and environmentally – friendly green pesticides. Nature Publishing Group UK 2018-05-21 /pmc/articles/PMC5962541/ /pubmed/29784959 http://dx.doi.org/10.1038/s41598-018-26242-6 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Feng, Yan
Chen, Jian
Zhang, Aijun
Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title_full Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title_fullStr Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title_full_unstemmed Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title_short Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests
title_sort commercially available natural benzyl esters and their synthetic analogs exhibit different toxicities against insect pests
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5962541/
https://www.ncbi.nlm.nih.gov/pubmed/29784959
http://dx.doi.org/10.1038/s41598-018-26242-6
work_keys_str_mv AT fengyan commerciallyavailablenaturalbenzylestersandtheirsyntheticanalogsexhibitdifferenttoxicitiesagainstinsectpests
AT chenjian commerciallyavailablenaturalbenzylestersandtheirsyntheticanalogsexhibitdifferenttoxicitiesagainstinsectpests
AT zhangaijun commerciallyavailablenaturalbenzylestersandtheirsyntheticanalogsexhibitdifferenttoxicitiesagainstinsectpests