Discovery of metaflumizone, a novel semicarbazone insecticide

Takagi, Kazuhiro; Hamaguchi, Hiroshi; Nishimatsu, Tetsuyoshi; Konno, Takamichi

doi:10.1016/j.vetpar.2007.08.031

Cited by 52 publications

(32 citation statements)

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“…Interestingly, metaflumizone, like the BZPs, lacks a chiral center, and therefore lacks the stereoselectivity demonstrated by RH-3421 and related dihydropyrazoles or indoxacarb. Despite this difference, however, metaflumizone does contain a shared core structure with dihydropyrazoles and indoxacarb which has been proposed by Takagi et al [22] (Fig. 1F) to be the toxophore responsible for the insecticidal activity of the SCBI class (BZPs do not contain this central structural element yet induce similar symptoms of poisoning and so are included in the SCBI class).…”

Section: Introductionmentioning

confidence: 94%

“…1E) is the second, and only other, member of the SCBI class to be commercialized as an insecticide [21, 22], and it features a semicarbazone structure that is essentially the opened-ring version of the dihydropyrazoles. Interestingly, metaflumizone, like the BZPs, lacks a chiral center, and therefore lacks the stereoselectivity demonstrated by RH-3421 and related dihydropyrazoles or indoxacarb.…”

Section: Introductionmentioning

confidence: 99%

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Molecular Mechanism of Action and Selectivity of Sodium Ch annel Blocker Insecticides

Silver

Dong

Zhorov

2017

CMC

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Sodium channel blocker insecticides (SCBIs) are a relatively new class of insecticides that are represented by two commercially registered compounds, indoxacarb and metaflumizone. SCBIs, like pyrethroids and DDT, target voltage-gated sodium channels (VGSCs) to intoxicate insects. In contrast to pyrethroids, however, SCBIs inhibit VGSCs at a distinct receptor site that overlaps those of therapeutic inhibitors of sodium channels, such as local anesthetics, anticonvulsants and antiarrhythmics. This review will recount the development of the SCBI insecticide class from its roots as chitin synthesis inhibitors, discuss the symptoms of poisoning and evidence supporting inhibition of VGSCs as their mechanism of action, describe the current model for SCBI-induced inhibition of VGSCs, present a model for the receptor for SCBIs on VGSCs, and highlight differences between data collected from mammalian and insect experimental models.

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Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Molecular Mechanism of Action and Selectivity of Sodium Ch annel Blocker Insecticides

Silver

Dong

Zhorov

2017

CMC

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“…Moreover, semicarbazones have been used as organic & Nosrat O. Mahmoodi mahmoodi@guilan.ac.ir; nosmahmoodi@gmail.com corrosion inhibitors [15]. Metaflumizone, under the brand name ProMeris, is a semicarbazone derivative with eco-friendly insecticide activity [16] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

et al. 2015

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New series of 2-(aryl or alkyl)-N-phenylhydrazine-1-carboxamides 1a-j were synthesized through one-pot reactions of aldehyde or ketones, hydrazine hydrate, and phenylisocyanate in MeOH. The structure of products was confirmed by Fourier transform infrared (FT-IR), proton nuclear magnetic resonance ( 1 H NMR), and 13 C NMR spectra. Minimum inhibitory concentration (MIC) of antibacterial activity of 1a-j was screened against five bacterial strains. Compound 1f showed antibacterial activity against Pseudomonas aeruginosa and Staphylococcus aureus.

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“…酰腙类化合物是分子中含有 CONHN＝C 活性单元的一类含氮化合物, 其特殊的结构单元使得酰腙类化合物表现出广泛的生物活性, 如杀虫 [1] 、杀菌 [2] 、除草 [3] 、抗肿瘤 [4,5] 等, 在农药、医药领域中应用广泛, 如氰氟虫腙(metaflumizon) 就是一种已经商品化的酰腙类杀虫剂, 它具有广谱杀虫、低毒的特点. 另外酰腙结构中的羰基氧、甲亚氨基氮具有很强的配位能力, 可与过渡金属形成配合物, 因此这类化合物还广泛应用于配位化学领域 [6] .…”

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Synthesis and Biological Activities of Novel AcylhydrazoneContaining 1,2,4-Triazole Structure

韩杰¹,

周晓霞²,

陈思宝³

et al. 2014

Chin. J. Org. Chem.

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Sixteen new acylhydrazone derivatives and twelve intermediates were synthesized using substituted aromatic acids as the staring materials. The structures of the target compounds and intermediates were characterized by IR, NMR and elemental analyses. And that the geometrical isomers of target compounds undergo a rapid cis/trans equilibrium, with the trans conformer predominating at room temperature. The auxin activity test showed that the target compounds have different effect on wheat gemma, the antibacterial activity was present in almost all the target compounds, but better activity was observed against Staphylococcus aureus than Escherichia coli. Particularly compound 4h exhibits higher antibacterial activity to Staphylococcus aureus than the others. The minimal inhibitory concentration (MIC) of 4h with Staphylococcus aureus is 3.13 μg/mL which is similar with chloramphenicol.

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Discovery of metaflumizone, a novel semicarbazone insecticide

Cited by 52 publications

References 1 publication

Molecular Mechanism of Action and Selectivity of Sodium Ch annel Blocker Insecticides

Molecular Mechanism of Action and Selectivity of Sodium Ch annel Blocker Insecticides

Practical one-pot synthesis of semicarbazone derivatives via semicarbazide, and evaluation of their antibacterial activity

Synthesis and Biological Activities of Novel AcylhydrazoneContaining 1,2,4-Triazole Structure

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