The mode of action of a nitroconjugated neonicotinoid and the effects of target site mutation Y151S on its potency

Shao, Xusheng; Lü, Haiyan; Bao, Haibo; Xu, Xiaoyong; Liu, Zewen; Zhong, Li

doi:10.1016/j.ibmb.2011.04.005

Cited by 23 publications

(12 citation statements)

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“…[30][31][32] An interesting finding is that the imidacloprid resistant populations of N. lugens showed little cross-resistance to these potential neonicotinoids with a -NO 2 or -CN group in trans-configuration. 33,34) Among these potential neonicotinoids, the dicyclic neonicotinoids with cis-configuration discriminated between the highand low-affinity imidacloprid-binding sites in N. lugens and their potencies were only slightly influenced by the previously identified mutation Y151S in N. lugens. 24,34) Another potential neonicotinoids with -NO 2 or -CN group in trans-configuration was synthesized by replacing nitromethylene pharmacophore with a nitro-conjugated system, with a representative member IPPA152201.…”

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confidence: 99%

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Overall status of neonicotinoid insecticides in China: Production, application and innovation

et al. 2013

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Section: )mentioning

confidence: 99%

“…The potency of IPPA152201 on hybrid receptors Nlα1/β2 expressed in Xenopus oocytes was also only slightly influenced by the Y151S mutation, relative to that of imidacloprid and other commercial neonicotinoids. 33) …”

Section: )mentioning

confidence: 99%

Overall status of neonicotinoid insecticides in China: Production, application and innovation

et al. 2013

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“…Darüber hinaus wurde für beide Verbindungen eine 30‐fache Aktivität gegen Stämme der braunen Spitzkopfzikade ( Nilaparvata lugens Stal ) beschrieben, die gegenüber 7 resistent sind. Sowohl Paichongding ( rac ‐ 38 ) als auch IPAA152201 ( 39 ) werden durch die Y151S‐Mutation in N1α1 teilweise beeinflusst, jedoch wurde die Mutation noch in keiner im Feld gesammelten Population identifiziert 85. Für rac ‐ 38 konnte von seinem 2‐Chlor‐1,3‐thiazol‐5‐ylmethyl‐Bioisoster vor kurzem eine hohe insektizide Wirkung gegen Bohnenblattläuse ( A. craccivora ) nachgewiesen werden 86…”

Section: Aktuelle Trendsunclassified

CO₂ and Formate Complexes of Phosphine/Borane Frustrated Lewis Pairs

Peuser

Neu

Zhao

et al. 2011

Chemistry A European J

153

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The reaction of a solution of B(C6F4H)3 and either iPr3P or tBu3P with CO2 afforded the species R3P(CO2)B(C6F4H)3 (R=iPr (1), tBu (2)). In a similar fashion the boranes, RB(C6F5)2 (R=hexyl, cyclohexyl (Cy), norbornyl), ClB(C6F5)2, or PhB(C6F5)2 were combined with tBu3P and CO2 to give the species tBu3P(CO2)BR(C6F5)2 (R=hexyl (3), Cy (4), norbornyl (5), Cl (6), Ph (7)). Similarly, the compounds [tBu3PH][RBH(C6F5)2] (R= hexyl (8), Cy (9), norbornyl (10)) were prepared by reaction of the precursor frustrated Lewis pair (FLP) with H2. Subsequent reactions of 9 and 10 with CO2 afforded the species [((C6F5)2BR)2(μ-HCO2)][tBu3PH] (R= Cy (11), norbornyl (12)). In related chemistry, combinations of the boranes RBG(C6F5)2 (R=hexyl, Cy, norbornyl) with tBu3P treated with an equivalent of formic acid gave [(C6F5)2BR(HCO2)][tBu3PH] (R=hexyl (13), Cy (14), norbornyl (15)). Subsequent addition of an additional equivalent of borane provides a second synthetic route to 11 and 12. Crystallographic studies of compounds 2-6 and 8-14 are reported and discussed. Further understanding of the FLP complexation and activation of CO2 is provided by computational studies.

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“…Since the first neonicotinoid insecticide, imidacloprid, was introduced as a commercial insecticide in the early 1990s, it has shown the most rapid growth in sales among insecticides worldwide (Matsuda et al, 2001). Six other neonicotinoid chemicals also have been developed into insecticides, such as nitenpyram, acetamiprid, thiamethoxam, thiacloprid, clothianidin and dinotefuran (Shao et al, 2011). Moreover, a novel type of nAChR-targeting insecticide, the sites of which are different from imidacloprid, has been used to improve the efficiency of insect pest control.…”

Section: Introductionmentioning

confidence: 99%

Molecular characterization and expression profiles of nicotinic acetylcholine receptors in the rice striped stem borer, Chilo suppressalis (Lepidoptera: Crambidae)

Teng

et al. 2016

Insect Science

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Nicotinic acetylcholine receptors (nAChRs) are members of the cys-loop ligandgated ion channel (cysLGIC) superfamily, mediating fast synaptic cholinergic transmission in the central nervous system in insects. Insect nAChRs are the molecular targets of economically important insecticides, such as neonicotinoids and spinosad. Identification and characterization of the nAChR gene family in the rice striped stem borer, Chilo suppressalis, could provide beneficial information about this important receptor gene family and contribute to the investigation of the molecular modes of insecticide action and resistance for current and future chemical control strategies. We searched our C. suppressalis transcriptome database using Bombyx mori nAChR sequences in local BLAST searches and obtained the putative nAChR subunit complementary DNAs (cDNAs) via reverse transcription polymerase chain reaction (RT-PCR) and rapid amplification of cDNA ends methods. Similar to B. mori, C. suppressalis possesses 12 nAChR subunits, including nine α-type and three β-type subunits. Quantitative RT-PCR analysis revealed the expression profiles of the nAChR subunits in various tissues, including the brain, subesophageal ganglion, thoracic ganglion, abdominal ganglion, hemocytes, fat body, foregut, midgut, hindgut and Malpighian tubules. Developmental expression analyses showed clear differential expression of nAChR subunits throughout the C. suppressalis life cycle. The identification of nAChR subunits in this study will provide a foundation for investigating the diverse roles played by nAChRs in C. suppressalis and for exploring specific target sites for chemicals that control agricultural pests while sparing beneficial species.

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The mode of action of a nitroconjugated neonicotinoid and the effects of target site mutation Y151S on its potency

Cited by 23 publications

References 31 publications

Overall status of neonicotinoid insecticides in China: Production, application and innovation

Overall status of neonicotinoid insecticides in China: Production, application and innovation

CO₂ and Formate Complexes of Phosphine/Borane Frustrated Lewis Pairs

Molecular characterization and expression profiles of nicotinic acetylcholine receptors in the rice striped stem borer, Chilo suppressalis (Lepidoptera: Crambidae)

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The mode of action of a nitroconjugated neonicotinoid and the effects of target site mutation Y151S on its potency

Cited by 23 publications

References 31 publications

Overall status of neonicotinoid insecticides in China: Production, application and innovation

Overall status of neonicotinoid insecticides in China: Production, application and innovation

CO2 and Formate Complexes of Phosphine/Borane Frustrated Lewis Pairs

Molecular characterization and expression profiles of nicotinic acetylcholine receptors in the rice striped stem borer, Chilo suppressalis (Lepidoptera: Crambidae)

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Product

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CO₂ and Formate Complexes of Phosphine/Borane Frustrated Lewis Pairs