Herbicidal Activity of Cineole Derivatives

Essential oils and their constituents have potential as ecologically acceptable pesticides that may also have novel modes of action. In this work hydroxy and ester derivatives of the naturally occurring monoterpenoids 1,8-cineole 3, the main component in most eucalyptus oils, and 1,4-cineole 4 were...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2010-09, Vol.58 (18), p.10147-10155
Main Authors: Barton, Allan F. M, Dell, Bernard, Knight, Allan R
Format: Article
Language:English
Subjects:
bioassays
Biological and medical sciences
biological control agents
chemical analysis
chemical composition
cineole derivatives
Crop and Animal Protection Chemistry
Cyclohexanols - chemistry
essential oils
Eucalyptus
Eucalyptus - chemistry
Fat industries
Food industries
Fruit and vegetable industries
Fundamental and applied biological sciences. Psychology
Germination
herbicidal properties
Herbicides - chemical synthesis
Herbicides - chemistry
Lolium
Monoterpenes - chemistry
Oils, Volatile - chemistry
Raphanus
weed control
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Summary:Essential oils and their constituents have potential as ecologically acceptable pesticides that may also have novel modes of action. In this work hydroxy and ester derivatives of the naturally occurring monoterpenoids 1,8-cineole 3, the main component in most eucalyptus oils, and 1,4-cineole 4 were prepared and their pre-emergence herbicidal activity against annual ryegrass (Lolium rigidum) and radish (Raphanus sativus var. Long Scarlet) investigated in laboratory-based bioassays. 1,8-Cineole, eucalyptus oil and all derivatives showed a dose-dependent herbicidal activity against annual ryegrass and radish with many of the derivatives showing improved herbicidal activity relative to 1,8-cineole and high-cineole eucalyptus oil. Increased activity of cineole ester derivatives compared to their associated hydroxy-cineole and carboxylic acid was not observed. No relationship between lipophilicity of the carboxylic acid portion of cineole ester derivatives and herbicidal activity was observed. The results indicate that these cineole derivatives could be environmentally acceptable herbicides.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf101827v