The discovery of isocycloseram: A novel isoxazoline insecticide

Cassayre, Jérôme; Šmejkal, Tomáš; Blythe, Judith; Hoegger, Patrik J.; Renold, Peter; Pitterna, Thomas; Prasanna, C.S.; Smits, Helmars; Godineau, Edouard; Luksch, Torsten; Berthon, Guillaume; Rawal, Girish; Patre, Rupesh E.; Lal, Mukul; Boussemghoune, Mohamed; Masala, Simonetta; Barreteau, Fabien; Flaeschel, Michael; Vogt, Juliane; Qacemi, Myriem El

doi:10.1016/b978-0-12-821035-2.00008-5

Cited by 15 publications

(7 citation statements)

References 59 publications

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“…The Aichi-R-ns strain also exhibited resistance to other avermectin insecticides and compounds belonging to six different insecticide classes (diamides, oxadiazines, spinosyns, pyrethroids, organochlorines and fiproles). Only one insecticide tested, isocycloseram, a novel insecticide that acts as an allosteric modulator of GABA gated chloride channels, 29 was not severely affected by resistance. Acquiring knowledge on the resistance profile of regional pest populations is a prerequisite for the development of effective pest and resistance management programs.…”

Section: Discussionmentioning

confidence: 99%

Characterization of emamectin benzoate resistance in the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae)

Oplopoiou,

Elias,

Slater

et al. 2023

Pest Management Science

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BACKGROUNDPlutella xylostella (L.) is a destructive pest of cruciferous crops worldwide that has evolved resistance to many insecticides. Here we examined the mode of inheritance, cross‐resistance profile, and potential mechanisms of emamectin benzoate resistance in a field‐derived strain of P. xylostella from Japan.RESULTSA field‐collected population of P. xylostella, was found to exhibit strong (>150‐fold) resistance to emamectin benzoate in insecticide bioassays when compared with a laboratory susceptible strain. Genetic analysis showed that resistance is inherited as an autosomal, recessive trait, and is conferred by a single or a few closely linked loci. The emamectin benzoate resistant strain also exhibited resistance to abamectin, lepimectin, chlorantraniliprole, lufenuron, spinetoram, indoxacarb, fipronil, dieldrin, endosulfan and lambda‐cyhalothrin, demonstrating a remarkable multi‐resistance profile. Insecticide bioassays employing inhibitors of detoxification enzymes revealed that piperonyl butoxide (PBO) increased the toxicity of emamectin benzoate in the resistant strain by 10‐fold indicating the potential involvement of cytochrome P450 monooxygenases in avermectin resistance. Furthermore, cloning and sequencing of the primary receptor of avermectins, the GluCl channel, revealed the absence of target‐site mutations in the resistant strain.CONCLUSIONSOur data on the mode of inheritance and mechanisms of resistance to emamectin benzoate in a P. xylostella strain from Japan provide a foundation for the development of regional resistance management strategies. However, the high levels of phenotypic resistance in this strain to a diverse range of other insecticide classes available for control illustrate the challenges associated with the sustainable control of this important pest.This article is protected by copyright. All rights reserved.

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Section: Discussionmentioning

confidence: 99%

Characterization of emamectin benzoate resistance in the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae)

Oplopoiou,

Elias,

Slater

et al. 2023

Pest Management Science

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“…demonstrated the lack of cross‐resistance with cyclodienes using WT and cyclodiene‐resistant strains of Drosophila . Other members of IRAC group 30, such as the isoxazolines fluralaner, fluxametamide and isocycloseram, and the meta‐diamide broflanilide, previously were shown to exhibit excellent acaricidal activity against T. urticae , with in some cases even higher activity compared to commercially available acaricides 31,32,42–45 …”

Section: Discussionmentioning

confidence: 99%

Activity, selection response and molecular mode of action of the isoxazoline afoxolaner in Tetranychus urticae

Mermans

Dermauw

Geibel

et al. 2022

Pest Management Science

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BACKGROUND Afoxolaner is a novel representative of the isoxazolines, a class of ectoparasiticides which has been commercialized for the control of tick and flea infestations in dogs. In this study, the biological efficacy of afoxolaner against the two‐spotted spider mite Tetranychus urticae was evaluated. Furthermore, as isoxazolines are known inhibitors of γ‐aminobutyric acid‐gated chloride channels (GABACls), the molecular mode of action of afoxolaner on T. urticae GABACls (TuRdls) was studied using functional expression in Xenopus oocytes followed by two‐electrode voltage‐clamp (TEVC) electrophysiology, and results were compared with inhibition by fluralaner, fipronil and endosulfan. To examine the influence of known GABACl resistance mutations, H301A, I305T and A350T substitutions in TuRdl1 and a S301A substitution in TuRdl2 were introduced. RESULTS Bioasassays revealed excellent efficacy of afoxolaner against all developmental stages and no cross‐resistance was found in a panel of strains resistant to most currently used acaricides. Laboratory selection over a period of 3 years did not result in resistance. TEVC revealed clear antagonistic activity of afoxolaner and fluralaner for all homomeric TuRdl1/2/3 channels. The introduction of single, double or triple mutations to TuRdl1 and TuRdl2 did not lower channel sensitivity. By contrast, both endosulfan and fipronil had minimal antagonistic activities against TuRdl1/2/3, and channels carrying single mutations, whereas the sensitivity of double and triple TuRdl1 mutants was significantly increased. CONCLUSIONS Our results demonstrate that afoxolaner is a potent antagonist of GABACls of T. urticae and has a powerful mode of action to control spider mites. © 2022 Society of Chemical Industry.

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“…A requirement for a reduced amount of product allows for the exploration of more diverse and complex chemistry that can meet more stringent performance, safety, and sustainability criteria while continuing to reduce the cost of application per hectare . As a result, agricultural chemicals are increasing in complexity and approaching that of drug candidates. − Examples that illustrate this trend include cyclobutrifluram ( 272 ), an inhibitor of the mitochondrial succinate dehydrogenase (SDH) in nematodes, isocycloseram ( 273 ), a modulator of the insect γ-aminobutyric acid (GABA)-gated chloride channels, and insecticide and acaricide spiropidion ( 274 ), a procide of the active acetyl-CoA-carboxylase-inhibiting principle. − …”

Section: Epiloguementioning

confidence: 99%

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 2

Meanwell

Loiseleur

2022

J. Agric. Food Chem.

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Applications of piperazine and homopiperazine in drug design are well-established, and these heterocycles have found use as both scaffolding and terminal elements and also as a means of introducing a water-solubilizing element into a molecule. In the accompanying review (10.1021/acs.jafc.2c00726), we summarized applications of piperazine and homopiperazine and their fused ring homologues in bioactive compound design along with illustrations of the use of 4-substituted piperidines and a sulfoximine-based mimetic. In this review, we discuss applications of pyrrolidine- and fused-pyrrolidine-based mimetics of piperazine and homopiperazine and illustrate derivatives of azetidine that include stretched and spirocyclic motifs, along with applications of a series of diaminocycloalkanes.

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The discovery of isocycloseram: A novel isoxazoline insecticide

Cited by 15 publications

References 59 publications

Characterization of emamectin benzoate resistance in the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae)

Characterization of emamectin benzoate resistance in the diamondback moth, Plutella xylostella (Lepidoptera: Plutellidae)

Activity, selection response and molecular mode of action of the isoxazoline afoxolaner in Tetranychus urticae

Applications of Isosteres of Piperazine in the Design of Biologically Active Compounds: Part 2

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