Synthesis and structure–activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF‐3535) as an anti‐Botrytis agent

Nagata, Toshihiro; Masuda, Katsumi; Maeno, Shinichiro; Miura, Ichiro

doi:10.1002/ps.828

Cited by 40 publications

(18 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In A6, one of the thienyl rings of α-terthienyl has been substituted by a pyrimidine, making it structurally related to another class of pesticides, the anilinopyrimidines, which are widely used to protect plants from the cryptogamic fungus, Bothritis cinerea [16]. In a previous study, we showed that A6 is able to induce the formation of sodium dodecyl sulfate (SDS)-resistant oligomers of the misfolded prion protein, called PrP Sc , in a prion-infected cell line [17,18,19].…”

Section: Introductionmentioning

confidence: 99%

Neurotoxicity of a Biopesticide Analog on Zebrafish Larvae at Nanomolar Concentrations

Nasri

Valverde

Roche

et al. 2016

IJMS

View full text Add to dashboard Cite

Despite the ever-increasing role of pesticides in modern agriculture, their deleterious effects are still underexplored. Here we examine the effect of A6, a pesticide derived from the naturally-occurring α-terthienyl, and structurally related to the endocrine disrupting pesticides anilinopyrimidines, on living zebrafish larvae. We show that both A6 and an anilinopyrimidine, cyprodinyl, decrease larval survival and affect central neurons at micromolar concentrations. Focusing on a superficial and easily observable sensory system, the lateral line system, we found that defects in axonal and sensory cell regeneration can be observed at much lower doses, in the nanomolar range. We also show that A6 accumulates preferentially in lateral line neurons and hair cells. We examined whether A6 affects the expression of putative target genes, and found that genes involved in apoptosis/cell proliferation are down-regulated, as well as genes reflecting estrogen receptor activation, consistent with previous reports that anilinopyrimidines act as endocrine disruptors. On the other hand, canonical targets of endocrine signaling are not affected, suggesting that the neurotoxic effect of A6 may be due to the binding of this compound to a recently identified, neuron-specific estrogen receptor.

show abstract

Section: Introductionmentioning

confidence: 99%

Neurotoxicity of a Biopesticide Analog on Zebrafish Larvae at Nanomolar Concentrations

Nasri

Valverde

Roche

et al. 2016

IJMS

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4] Anilinopyrimidine fungicides can control fungal diseases caused by Botrytis cinerea (gray mold), Venturia spp. (scab), Alternaria mali (alternaria leaf spot), Podosphaera leucotricha (powdery mildew) and others.…”

Section: Mepanipyrimmentioning

confidence: 99%

A Method for Monitoring the Sensitivity of Botrytis cinerea to Mepanipyrim

2004

View full text Add to dashboard Cite

Mepanipyrim is an anilinopyrimidine fungicide with a broad spectrum of activities. Mepanipyrim did not inhibit mycelial growth of Botrytis cinerea completely on complex media and therefore, this method is considered not to be useful for evaluation of the sensitivity of isolated B. cinerea to mepanipyrim. As a result of our studies, we have established new techniques to determine the fungal sensitivity to mepanipyrim in vitro by utilizing the inhibitory activity of mepanipyrim against protein secretion and germ-tube elongation. The FGA-paper disc method is considered to be more useful and more reliable for evaluation of the sensitivity of B. cinerea to mepanipyrim.

show abstract

“…In this regard, strobilurin analogues that possess methoxyiminoacetate have attracted much attention from agricultural chemists owing to their powerful antifungal activities against resistant pathogens. [21][22][23][24] Utilizing the intermediate derivatisation method based on the active substructure combination and bioisosteric replacement, [25] a series of novel strobilurin derivatives containing pyrimidine moieties and strobilurin pharmacophore were designed and synthesized with the aim of obtaining more active candidates than the conventional azoxystrobin, hopefully against resistant fungal strains. [16,17,19,20] Pyrimidine derivatives widely existing in nature usually have excellent biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activities of New Type β‐Methoxyacrylate‐Based Strobilurin Analogues

et al. 2012

View full text Add to dashboard Cite

Strobilurins have become one of the most important classes of agricultural fungicides. To discover new strobilurin derivatives with high activity against resistant pathogens, a series of novel β-methoxyacrylate analogues were designed and synthesized by integrating substituted pyrimidine with a strobilurin pharmacophore. The compounds were confirmed and characterized by infrared, 1 H nuclear magnetic resonance, elemental analysis and mass spectroscopy. The bioassays indicated that most of the compounds 1 exhibited potent antifungal activity against Colletotrichum orbiculare, Botrytis cinerea Pers and Phytophthora capsici Leonian at the concentration of 50 µg/mL. Exhilaratingly, compound 1a (R＝methyl) showed better antifungal activity against all the tested fungi than the commercial strobilurin fungicide azoxystrobin.

show abstract

Synthesis and structure–activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF‐3535) as an anti‐Botrytis agent

Cited by 40 publications

References 28 publications

Neurotoxicity of a Biopesticide Analog on Zebrafish Larvae at Nanomolar Concentrations

Neurotoxicity of a Biopesticide Analog on Zebrafish Larvae at Nanomolar Concentrations

A Method for Monitoring the Sensitivity of Botrytis cinerea to Mepanipyrim

Synthesis and Antifungal Activities of New Type β‐Methoxyacrylate‐Based Strobilurin Analogues

Contact Info

Product

Resources

About