Monoterpenoids and Their Synthetic Derivatives as Leads for New Insect-Control Agents

Tsao, Rong; Lee, Sangkyun; Rice, Pamela J.; Jensen, Cheryl A.; Coats, Joel R.

doi:10.1021/bk-1995-0584.ch028

Cited by 59 publications

(52 citation statements)

References 7 publications

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“…Essential oils are commonly used because they are quite efficacious against all life stages of insects. Moreover, it has been widely reported that terpenes from a variety of essential oils derived from vegetative sources have potent insect pest control properties, which affect the biology of target insects in different ways by acting either as ovicides, repellants, antifeedants, fumigants, contact toxicants or insecticides (Hough-Goldstein, 1990;Watanabe et al, 1993;Rice and Coats, 1994;Tsao et al, 1995). It is therefore, possible that the efficacy seen with the dried leaves of the three botanicals against the bruchid pests could be attributable to these and other constituents.…”

Section: Discussionmentioning

confidence: 99%

Controlling bruchid pests of stored cowpea seeds with dried leaves of Artemisia annua and two other common botanicals

Ebiamadon¹,

Brisibe²,

Sophia³

et al. 2011

Afr. J. Biotechnol.

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Insecticidal activities of dried Artemisia annua L. leaves were evaluated against bruchid (Callosobruchus maculatus F.) pests in comparison with those of Azadirachta indica, Ocimum gratissimum and a conventional grain storage insecticide, Actellic® 2% dust. Each treatment was added to a mixture of 250 g cowpea seeds and 25 adult bruchids and laid out in a completely randomized design with four replicates. Irrespective of the concentration tested, all three plant materials significantly (P < 0.05) increased mortality rate of adult insects earlier than the control. Higher concentrations of the botanical pesticides equally resulted in an increased reduction in the number of surviving bruchids and reduction to seed damage through a lower number of eggs laid and weevil perforation index (WPI) after 90 days. Comparatively, A. annua was more effective than the other plant materials at all levels evaluated though it was not as effective as Actellic 2% dust. Moreover, differences amongst the efficiency rates and interactions between A. annua and A. indica in three treatment combinations produced a significant (P < 0.05) effect on two of the parameters evaluated. Taken together, all plant materials evaluated here were seen to have significant insecticidal properties and could therefore, be used as environmentally friendly products for controlling bruchid pests during storage of cowpeas with no adverse effects on eventual mammalian consumers as observed during an animal feeding trial in this study.

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Section: Discussionmentioning

confidence: 99%

Controlling bruchid pests of stored cowpea seeds with dried leaves of Artemisia annua and two other common botanicals

Ebiamadon¹,

Brisibe²,

Sophia³

et al. 2011

Afr. J. Biotechnol.

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“…LD50s of all the monoterpenoids were calculated using the Spearman-Karber method (11). Some compounds' LD50 values were previously reported from our lab (3,10). LD50 values were converted to be expressed as µmol/fly.…”

Section: Synthesis Of Monoterpenoid Estersmentioning

confidence: 99%

QSAR Evaluation of Monoterpenoids' Insecticidal Activity

Grodnitzky

Coats

2002

J. Agric. Food Chem.

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Monoterpenoids are naturally occurring compounds that are found in higher-order plants. These compounds are secondary metabolites that seem to play no major role in the metabolic functioning of the plants. One role of monoterpenoids in the plants is to defend against plant-directed pathogens, herbivores, or competing plant species. These compounds are good leads for synthesis or isolation of more effective insecticides. To accomplish these goals, we developed quantitative structure−activity relationships (QSARs) in order to predict insect toxicity of monoterpenoids and derivatives that have not yet been synthesized or experimentally tested. Correlations were found between toxicity and certain quantum and traditional chemical parameters. We found a linear relationship between LD50 values for house fly toxicity and Mulliken populations in aromatic monoterpenoids. Multiple linear regression of an E-State descriptor and a GETAWAY (GEometry, Topology and Atomic Weights AssemblY) descriptor also showed a relationship with house fly toxicity for a wide range of monoterpenoids. KeywordsQuantitative structure−activity relationship (QSAR), monoterpenoid, insecticide, Mulliken population, quantum descriptor, electrotopological state Disciplines Entomology CommentsReprinted with permission from Journal of Agricultural and Food Chemistry 50 (2002) Monoterpenoids are naturally occurring compounds that are found in higher-order plants. These compounds are secondary metabolites that seem to play no major role in the metabolic functioning of the plants. One role of monoterpenoids in the plants is to defend against plant-directed pathogens, herbivores, or competing plant species. These compounds are good leads for synthesis or isolation of more effective insecticides. To accomplish these goals, we developed quantitative structureactivity relationships (QSARs) in order to predict insect toxicity of monoterpenoids and derivatives that have not yet been synthesized or experimentally tested. Correlations were found between toxicity and certain quantum and traditional chemical parameters. We found a linear relationship between LD 50 values for house fly toxicity and Mulliken populations in aromatic monoterpenoids. Multiple linear regression of an E-State descriptor and a GETAWAY (GEometry, Topology and Atomic Weights AssemblY) descriptor also showed a relationship with house fly toxicity for a wide range of monoterpenoids.

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“…1 Chemical modification of natural monoterpenoids has been reported to result in enhancement of biological activities when compared to parent compounds. [2][3][4][5] Thymol (1), a monoterpene biosynthetically directly related to para-cymene (1a) 6 and a naturally occurring phenol, is a well known biocide and most dominant constituent of the oils of thyme (Thymus vulgaris L.) and oregano (Origanum vulgare L.).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

Lazarević

Kolarević

Stojanović

et al. 2017

ACSi

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Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

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Monoterpenoids and Their Synthetic Derivatives as Leads for New Insect-Control Agents

Cited by 59 publications

References 7 publications

Controlling bruchid pests of stored cowpea seeds with dried leaves of Artemisia annua and two other common botanicals

Controlling bruchid pests of stored cowpea seeds with dried leaves of Artemisia annua and two other common botanicals

QSAR Evaluation of Monoterpenoids' Insecticidal Activity

Synthesis, Antimicrobial Activity and in silico Studies on Thymol Esters

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