Disruption of responses to pheromone by (<i>Z</i>)‐11‐hexadecenyl trifluoromethyl ketone, an analogue of the pheromone, in the cabbage armyworm <i>Mamestra brassicae</i>

Renou, Michel; Berthier, Andrée; Guerrero, Ángel

doi:10.1002/ps.534

Cited by 9 publications

(5 citation statements)

References 22 publications

(34 reference statements)

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“…Synthetic compounds can also alter the peripheral responses of insects. For example, trifluoromethyl ketone mimics of pheromones interfere with the EAG responses , , , and with the behavior of the insects toward their pheromone , , . Another example is DEET: it caused either a decrease or an enhancement in the response to food odors of selected olfactory neurons in Drosophila .…”

Section: Discussionmentioning

confidence: 99%

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Agonists and Antagonists of Antennal Responses of Gypsy Moth (Lymantria dispar) to the Pheromone (+)-Disparlure and Other Odorants

Plettner¹,

Gries²

2010

J. Agric. Food Chem.

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Insects use the sense of smell to guide many behaviors that are important for their survival. The gypsy moth uses a pheromone to bring females and males together over long distances. Male moth antennae are equipped with innervated sensory hairs that selectively respond to pheromone components and other odors. Host plant odors, in particular, are detected by moths and sometimes cause an enhancement of the antennal and behavioral responses of the moths to their pheromone. Inspired by naturally occurring agonists and antagonists of insect pheromone responses, we have screened, by electroantennogram (EAG) recordings, a collection of compound sets and of individual compounds. We have detected interference of some compounds with the EAG responses of male gypsy moth antennae to the pheromone. We describe three activities: (1) short-term inhibition or enhancement of mixed compound + pheromone plumes, (2) long-term inhibition of pure pheromone plumes following a mixed compound + pheromone plume, and (3) inhibition of the recovery phase of mixed compound + pheromone plumes. Long-term inhibition was robust, decayed within 30 s, and correlated with the inhibition of recovery; for both activities clear structure-activity patterns were detected. The commercial repellent N,N-diethyltoluamide (DEET) was included for comparison. The most active and reproducible short-term inhibitor was a mixture of 1-allyl-2,4-dimethoxybenzene and 2-allyl-1,3-dimethoxybenzene. The most active long-term inhibitors were a set of 1-alkoxy-4-propoxybenzenes, DEET, and 1-ethoxy-4-propoxybenzene. DEET was more specific in the olfactory responses it inhibited than 1-ethoxy-4-propoxybenzene, and DEET did not inhibit recovery, whereas 1-ethoxy-4-propoxybenzene did. Target sites for the three activities are discussed.

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Section: Discussionmentioning

confidence: 99%

“…In nature, host plant odors have been known to synergize with pheromone responses − and nonhost plant odors sometimes antagonize pheromone responses . Natural or synthetic pheromone mimics can also antagonize the response of an insect to its pheromone , .…”

Section: Introductionmentioning

confidence: 99%

Agonists and Antagonists of Antennal Responses of Gypsy Moth (Lymantria dispar) to the Pheromone (+)-Disparlure and Other Odorants

Plettner¹,

Gries²

2010

J. Agric. Food Chem.

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“…In brief, the inhibitory activity of TFMKs is due to a stable hemiacetal of tetrahedral geometry that is formed between the conserve serine residues of the antennal esterases with the highly electrophilic carbonyl (Durán et al, 1993;Wiedemann et al, 1998). Some studies have been performed with TFMKs and electrophysiological assays in Plutella xylostella (Prestwich and Streinz, 1988), Thaumetopoea pityocampa (Parrilla and Guerrero, 1994), M. brassicae (Renou et al, 2002), Cydia pomonella (Giner et al, 2009), and S. frugiperda (Malo et al, 2013). Moreover, TFMKs have been used with antennal extracts of different moth species, e.g., S. littoralis (Durán et al, 1993), Ostrinia nubilalis (Riba et al, 2005), and C. pomonella (Giner et al, 2009).…”

Section: Antennal Esterases Inhibition In Integrated Pest Managementmentioning

confidence: 99%

An Overview of Antennal Esterases in Lepidoptera

et al. 2021

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Lepidoptera are used as a model for the study of insect olfactory proteins. Among them, odorant degrading enzymes (ODEs), that degrade odorant molecules to maintain the sensitivity of antennae, have received less attention. In particular, antennal esterases (AEs; responsible for ester degradation) are crucial for intraspecific communication in Lepidoptera. Currently, transcriptomic and genomic studies have provided AEs in several species. However, efforts in gene annotation, classification, and functional assignment are still lacking. Therefore, we propose to combine evidence at evolutionary, structural, and functional level to update ODEs as well as key information into an easier classification, particularly of AEs. Finally, the kinetic parameters for putative inhibition of ODEs are discussed in terms of its role in future integrated pest management (IPM) strategies.

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“…The strict structural analogies to the natural pheromone could make the fluoro analogue 178 a good substrate for receptor recognition and transduction processes. The same compound was submitted107 to actographic investigation performed on Mamestra brassicae males. The actographic analysis showed that the latency of the response was proportional to the doses of the trifluoromethyl ketone and that the percentage of responding males was not affected.…”

Section: The Pheromonal Communication System Of Insectsmentioning

confidence: 99%

The Influence of Fluorinated Molecules (Semiochemicals and Enzyme Substrate Analogues) on the Insect Communication System

Pesenti

Viani

2004

ChemBioChem

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Can the introduction of fluorine atoms affect the bioactivity of natural semiochemicals? Can fluorine contribute in the creation of specific enzyme inhibitors to interrupt or disrupt the insect communication system? The first step for the bioactivity of a molecule is interaction with the biological sensor. Hydrogen and fluorine are almost bioisosteric and the receptor site of the enzyme can still recognize and accept the fluoro analogue of its natural substrate. However, the peculiar electronegativity of the fluorine atom can affect the binding, absorption, and transport of the molecule. The differences in the molecule's electronic properties can lead to differences in the chemical interactions between the receptor and the fluorinated substrate. Fluorine introduction can modify the metabolic stability and pathway of the semiochemicals in many different ways. Fluorinated analogues can show synergism, inhibition, or hyperagonism effects on insect behaviors, that is, the activity of the nonfluorinated parent compounds can be mimicked, lost, or increased. In any case, the fluorinated molecules can interact with the bioreceptors in a new and disrupting way. The semiochemicals are olfactory substances: fluorine can affect their volatility or smell. Production of semiochemicals from exogenous substances, perception at antennal receptors, and processing of biological responses are the main steps of communication among insects. In the production step, the fluorinated molecules can interact with enzymes that catalyze the biosynthesis of the natural pheromones. In the perception step, fluorinated semiochemicals can interact with the olfactory receptor cells; this often leads to totally unpredictable behaviors. Fluorinated molecules have been developed as probes to elucidate the complex chemorecognition processes of insects. Many of these molecules have been tested to find highly effective behavior-modifying chemicals. New analogues have been synthesized to investigate the metabolic pathway of a pheromone molecule and many of them are promising disrupting agents. Despite such titanic research efforts, the results have often been random, rational trends in the induced behaviors have sometimes been impossible to find, and practical applications of the fluorinated semiochemicals are still uncertain.

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Disruption of responses to pheromone by (Z)‐11‐hexadecenyl trifluoromethyl ketone, an analogue of the pheromone, in the cabbage armyworm Mamestra brassicae

Cited by 9 publications

References 22 publications

Agonists and Antagonists of Antennal Responses of Gypsy Moth (Lymantria dispar) to the Pheromone (+)-Disparlure and Other Odorants

Agonists and Antagonists of Antennal Responses of Gypsy Moth (Lymantria dispar) to the Pheromone (+)-Disparlure and Other Odorants

An Overview of Antennal Esterases in Lepidoptera

The Influence of Fluorinated Molecules (Semiochemicals and Enzyme Substrate Analogues) on the Insect Communication System

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