Benzpyrimoxan: Design, synthesis, and biological activity of a novel insecticide

Satoh, Eikoh; Kasahara, Ryota; Fukatsu, K.; Aoki, Takao; Harayama, Hiroto; Murata, Tetsuya

doi:10.1584/jpestics.d20-069

Cited by 8 publications

(9 citation statements)

References 1 publication

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“…Imidacloprid 17.8SL @ 25 g a.i./ ha was found inferior to benzpyrimoxan 10SC @ 100, 125 and 150g a.i./ ha and buprofezin 25SC @ 200 g a.i./ ha in controlling N. lugens and S. furcifera. These results corroborate the findings of Ghosh et al (2013) and Satoh et al (2021). Data in Table 2 reveal non-significant differences among the treatment plots w.r.t pretreatment number of spider/ hill.…”

Section: Resultssupporting

confidence: 91%

“…Similarly, at 15 DAS the differences in spider population were non-significant among treatment plots. These results corroborate the findings of Satoh et al (2021) on pollinators and beneficial arthropods.…”

Section: Resultssupporting

confidence: 91%

“…A similar trend was observed at 10 DAS and 15 DAS where benzpyrimoxan 10SC @ 150 g a.i./ ha recorded the lowest N. lugens incidence (4.78 and 6.67 hoppers/ hill, respectively) and was found equally effective to its lower doses @ 100 (4.92 and 6.80 hoppers/ hill, respectively), 125 g a.i./ ha (4.87 and 6.72 hoppers/ hill, respectively) and buprofezin (4.62 and 6.12 hoppers/ hill, respectively). Satoh et al (2021) also reported remarkable activity of benzpyrimoxan against nymphs of rice planthoppers, including strains resistant to existing insecticides. Asai et al (1983) and Ghosh et al (2013) also reported the slow action of buprofezin in controlling the N. lugens.…”

Section: Resultsmentioning

confidence: 97%

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Efficacy of Benzpyrimoxan 10SC Against Rice Planthoppers

Suri

Makkar

2022

ije

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The efficacy of foliar application of benzpyrimoxan 10SC @ 50, 75, 100, 125 and 150 g a.i./ ha besides the insecticidal checks imidacloprid 17.8SL @ 25 g a.i./ha and buprofezin 25SC @ 187.5 g a.i./ha was evaluated against the brown planthopper (BPH) Nilaparvata lugens (Stal.) and the white backed planthopper (WBPH) Sogatella furcifera (Horvath) on rice during kharif 2017 and 2018 at the Punjab Agricultural University, Ludhiana. Experimental design consisted of random blocks in three replications. Two years data revealed that benzpyrimoxan 10SC @ 100 g a.i./ha is significantly superior against the N. lugens and S. furcifera complex. Benzpyrimoxan 10SC @ 100 g a.i./ha gave significantly higher yield (34.17 q/ ha) than its lower doses but was statistically at par with its higher doses. Non-significant differences in number of spiders/hill among treated plots and untreated check at 10- and 15-DAS indicated the safety of benzpyrimoxan.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 97%

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Efficacy of Benzpyrimoxan 10SC Against Rice Planthoppers

Suri

Makkar

2022

ije

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“…Because N1-functionalized pyrazoles, such as 31, are incapable of directing C−H functionalizations (vide supra), we also evaluated the formation of N1-substituted pyrazoles (Figure 4C). Phenylhydrazine provided N1-phenylpyrazole (31) in 50% yield, which was a lower yield than when unsubstituted hydrazine was used likely due to the reduced nucleophilicity of the phenyl-bearing nitrogen. The constitution of 31 is consistent with a faster initial attack of the terminal phenylhydrazine nitrogen.…”

Section: ■ Results and Discussionmentioning

confidence: 89%

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

2022

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A method for the conversion of pyrimidines into pyrazoles by a formal carbon deletion has been achieved guided by computational analysis. The pyrimidine heterocycle is the most common diazine in FDA-approved drugs, and pyrazoles are the most common diazole. An efficient method to convert pyrimidines into pyrazoles would therefore be valuable by leveraging the chemistries unique to pyrimidines to access diversified pyrazoles. One method for the conversion of pyrimidines into pyrazoles is known, though it proceeds in low yields and requires harsh conditions. The transformation reported here proceeds under milder conditions, tolerates a wide range of functional groups, and enables the simultaneous regioselective introduction of N-substitution on the resulting pyrazole. Key to the success of this formal one-carbon deletion method is a room-temperature triflylation of the pyrimidine core, followed by hydrazine-mediated skeletal remodeling.

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“…Satoh and colleagues 35) describe multistep chemical derivatization of existing insecticidal and lead compounds using pyrimidin substituents. Their synthesis yielded benzpyrimoxan, a new, currently registered insecticide active against the brown planthopper (Nilaparvata lugens), a major pest of rice.…”

Section: Stage-specific Organismal Effects Of Jh Juvenoid Igrs and Of A Novel Insecticidementioning

confidence: 99%

New ways and new hopes for IGR development

Jindra

2021

J. Pestic. Sci.

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Insect Growth Regulators (IGRs) represent advanced, bio-rational insecticides. This Special Issue reflects progress in IGR development that has been enabled by insight into the molecular principles of biosynthetic or hormone signaling pathways. The unifying principle is aiming at processes and molecular targets that are unique to arthropods and ideally to narrower insect taxa representing pests or disease vectors. While some strategies of obtaining the desired compounds for chemical intervention rely on rational, structure-based design or computational power, others exploit technologies allowing automated, high-throughput screening of large chemical libraries. All avenues leading to selective and environmentally safe pest control are valid as we face the imminent threat of the declining world insect population.

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Benzpyrimoxan: Design, synthesis, and biological activity of a novel insecticide

Cited by 8 publications

References 1 publication

Efficacy of Benzpyrimoxan 10SC Against Rice Planthoppers

Efficacy of Benzpyrimoxan 10SC Against Rice Planthoppers

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

New ways and new hopes for IGR development

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