Fluorinated sterols, hormones and pheromones: Enzyme‐targeted disruptants in insects

Prestwich, Glenn D.

doi:10.1002/ps.2780170414

Cited by 59 publications

(16 citation statements)

References 36 publications

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“…The metabolic stability of the CÀF bond can be exploited to make a pro-insecticide, for example, 29-fluorostigmasterol. [10] Insects produce cholesterol by dealkylation of phytosterols like stigmasterol through a pathway not found in mammals that involves formation of monofluoroacetic acid and (À)-erythro-2-fluorocitrate, which are lethal to insects.…”

Section: Stability-metabolic Oxidative and Thermalmentioning

confidence: 99%

“…Shortening and simplification of the pentadienyl side chain of the insecticide pyrethrin I (9), [15] which was obtained from chrysanthemum flowers, led in the 1950s to the first synthetic and more stable pyrethroid, allethrin (10). [16] More than twenty years later, replacement of the cyclopentene alcohol group and introduction of the dichlorovinyl moiety resulted in permethrin (11), [17] which is applied to cotton at about 200 g a.i ha À .…”

Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

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The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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The task of inventing and developing active ingredients with useful biological activities requires a search for novel chemical substructures. This process may trigger the discovery of whole classes of chemicals of potential commercial interest. Similar biological effects can often be achieved by completely different compounds. However, compounds within a given structural family may exhibit quite different biological activities depending on their interactions with different intracellular proteins like enzymes or receptors. By varying the functional groups and structural elements of a lead compound, its interaction with the active site of the target protein, as well as its physicochemical, pharmacokinetic, and dynamic properties can be improved. In this context, the introduction of fluorine into active ingredients has become an important concept in the quest for a modern crop protection product with optimal efficacy, environmental safety, user friendliness, and economic viability. Fluorinated organic compounds represent an important and growing family of commercial agrochemicals. A number of recently developed agrochemical candidates represent novel classes of chemical compounds with new modes of action; several of these compounds contain new fluorinated substituents. However, the complex structure-activity relationships associated with biologically active molecules mean that the introduction of fluorine can lead to either an increase or a decrease in the efficacy of a compound depending on its changed mode of action, physicochemical properties, target interaction, or metabolic susceptibility and transformation. Therefore, it is still difficult to predict the sites in a molecule at which fluorine substitution will result in optimal desired effects.

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Section: Stability-metabolic Oxidative and Thermalmentioning

confidence: 99%

Section: Insecticides Containing Fluorine Pyrethroidesmentioning

confidence: 99%

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

2004

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“…Most research on the effects of plant sterols and triterpenes on insects are related to their effect on hormonal activity, often with the aim of employing them as insecticides (Prestwich, 1986). Sterols have an antagonistic effect on the ability of larvae to molt (Alder, 1995;Luu and Werner, 1996;Dugassa-Gobena et al, 1998), since insect metabolism is vulnerable to dietary sterols (Feldlaufer and Svoboda, 1988;Darvas, 1991;Svoboda, 1992).…”

Section: Biological Activitymentioning

confidence: 99%

Chemistry of Cirsium and Carduus: a role in ecological risk assessment for biological control of weeds?

Jordon‐Thaden

Louda

2003

Biochemical Systematics and Ecology

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Prediction of host plant range and ecological impact of exotic phytophagous insects, such as insects for classical biological control of weeds, represents a major challenge. Recently, the flowerhead weevil (Rhinocyllus conicus Fröl.), introduced from Europe into North America to control exotic thistles (Carduus spp.), has become invasive. It feeds heavily on some, but not all species of native North American thistles (Cirsium spp.). We hypothesized that such non-target use among native plants could be better predicted by knowledge of characteristic chemical profiles of secondary compounds to supplement the results of host specificity testing. To evaluate this hypothesis, we reviewed the literature on the chemistry of Cirsium and Carduus thistles. We asked what compounds are known to be present, what is known about their biological activity, and whether such information on chemical profiles would have better predicted realized host range and ecological effects of R. conicus in North America. We found an extensive, but incomplete literature on the chemistry of true thistles. Two main patterns emerged. First, consistent chemical similarities and interesting differences occur among species of thistles. Second, variation occurs in biologically active groups of characteristic compounds, specifically flavonoids, sterols, alkaloids and phenolic acids, that are known to influence host plant acceptance, selection, and feeding by phytophagous insects. Surprisingly, sesquiterpene lactones, which are characteristic in closely related Asteraceae, have not been extensively reported for Cirsium or Carduus. The minimal evidence on sesquiterpene lactones may reflect extraction methods vs. true absence. In summary, our review suggests further research on thistle chemistry in insect feeding is warranted. Also, since the exotic Canada thistle (Cirsium arvense) is an invasive thistle of current concern in North America, such research on mechanisms underlying host range expansion by exotic insects would be useful.

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“…18,19) Inhibition of the enzymatic degradation of odorant molecules may lead to the disruption of pheromone reception, and therefore it may be considered in new future strategies for pest control. 10,20) 3-Octylthio-1,1,1-trifluoropropan-2-one (OTFP) is a potent esterase inhibitor which has been reported to alter pheromone detection in Spodoptera littoralis and to disrupt male flight to a pheromone source after being exposed to vapors of the chemical. 21) This compound also induced lower amplitude responses to the pheromone of A. polyphemus on two receptor cells tuned to (E,Z)-6,11-hexadecadienyl acetate, substrate for the sensillar esterase, and (E,Z)-6,11-hexadecadienal, not a substrate for the esterase.…”

Section: )mentioning

confidence: 99%

Inhibition of electrophysiological response to the pheromone of the fall armyworm, Spodoptera frugiperda

2010

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In the search for new control methods for the fall armyworm (FAW), Spodoptera frugiperda (Lepidoptera: Noctuidae), we present the inhibition of the electroantennographic (EAG) response to the pheromone by 3-octylthio-1,1,1-trifluoropropan-2-one (OTFP). As a member of the trifluoromethyl ketones, OTFP is a potent inhibitor of serine esterases, particularly those of insect antennae. Exposure of antennal receptors to OTFP vapors resulted in a decreased amplitude and 2/3 repolarization time (2/3 RT) of the EAG response to the pheromone. The effect was reversible, with the amplitude and repolarization time being recovered upon suppression of the treatment. The non-fluorinated analogue 3-octhylthiopropan-2-one (OTP) did not affect either the amplitude or the 2/3 RT of the EAG response to the pheromone, confirming the key role played by fluorine atoms in this type of chemical. These results may be the basis for new behavioral studies with the aim of considering OTFP in future management strategies of the FAW.

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Fluorinated sterols, hormones and pheromones: Enzyme‐targeted disruptants in insects

Cited by 59 publications

References 36 publications

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

The Unique Role of Fluorine in the Design of Active Ingredients for Modern Crop Protection

Chemistry of Cirsium and Carduus: a role in ecological risk assessment for biological control of weeds?

Inhibition of electrophysiological response to the pheromone of the fall armyworm, Spodoptera frugiperda

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