Development of a New Acaricide, Fenpyroximate

Hamaguchi, Hiroshi; Kajihara, Osamu; Katoh, Minoru

doi:10.1584/jpestics.20.173

Cited by 27 publications

(8 citation statements)

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“…For the biological activity of pyrazole derivatives, see: Hamaguchi et al (1995); Motoba et al (1992). For a related structure, see: Yokoyama et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

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5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Shen

Fan

2011

Acta Crystallogr E Struct Rep Online

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“…For the biological activity of pyrazole derivatives, see: Hamaguchi et al (1995); Motoba et al (1992). For a related structure, see: Yokoyama et al (2004).…”

Section: Related Literaturementioning

confidence: 99%

“…The pyrazole ring is a prominent heterocyclic scaffold in numerous bioactive molecules. Many pyrazole-based compounds are reported to possess diverse biological activities (Motoba et al, 1992;Hamaguchi et al, 1995). The title compound (I), is an important intermediate for the synthesis of agrochemicals and drugs.…”

Section: S1 Commentmentioning

confidence: 99%

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Shen

Fan

2011

Acta Crystallogr E Struct Rep Online

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“…目前已商品化的杀虫剂有吡螨胺 (Tebufenpyrad) 和氯虫苯甲酰胺 (Chlorantraniliprole) 等 (图 1) [12] . 吡唑肟作为吡唑类化合物中的重要一员, 在农药与医药领域发挥着举足轻重的作用, 被广泛应用于杀菌、杀虫及抗肿瘤等分支 [13～15] , 其中典型性代表为杀螨剂唑螨酯(Fenpyroximate, 图 1), 该化合物一直被用来防治多种植食性螨 [16,17] . 近年来, 一些科研工作者在唑螨酯结构基础上衍生制备出不少具有新颖结构的吡唑肟衍生物, 如 Fu 等研发的化合物 D 在浓度为 100 mg/L 时对蚜虫和螨虫的杀灭活性分别为 90% 和 100% [18] ; He 课题组研究发现化合物 E 在浓度为 200 μg/mL 时对小菜蛾、蚜虫和螨虫均有 100%的防效 [19] ; Shi 等合成的化合物 F 在浓度为 500 μg/mL 时对粘虫的杀灭活性为 100%, 同时化合物 F 对人肝癌细胞 HepG2 还表现出较好的抗肿瘤活性, 其 IC 50 值为 2.6 μmol/L(图 1) [20] .…”

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Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

Zhu¹,

Zheng²,

Ni³

et al. 2020

Chin. J. Org. Chem.

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In search of novel pyrazole oximes with good biological activities, twenty pyrazole oxime compounds were prepared by introducing an oxazole unit into pyrazole oxime based on the structure of fenpyroximate. The structures of the target compounds were confirmed by 1 H NMR, 13 C NMR and elemental analysis. Preliminary bioassay displayed that some target compounds had wonderful insecticidal activities against Oriental armyworm or Aphis medicaginis at the concentrations of 500 and 100 μg/mL. At the concentration of 100 μg/mL, 5- 9s) showed 100% mortality rate against Oriental armyworm, and 5-(4-bromophenoxy)-1,3-dimethyl-1H-pyrazole-4-formyl-O-((5-(4-fluorophenyl)oxazol-2-yl)methyl)oxime (9g) and 9s exhibited 100% insecticidal property against Aphis medicaginis. Additionally, compound 9s possessed 70% insecticidal activity against Tetranychus cinnabarinus at 500 μg/mL.

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“…吡唑类衍生物作为含氮杂环体系中的一员, 以其优良的杀菌、杀虫、杀螨、抗病毒及抗肿瘤等活性而倍受农药与药物化学工作者的关注 [1～5] . 近年来, 具有多种农用生物活性的吡唑类化合物被相继开发出来, 如日本 Nihon Nohyaku 公司研制的杀螨剂唑螨酯(Fenpyroximate)具有击倒快、持效时间长、受季节影响小等特点, 可用于防治多种植食性螨 [6,7] , 美国 Du Pont 公司开发的杀虫剂氯虫苯甲酰胺对鳞翅目和半翅目类害虫表现优异的防效 [8] . 许多含吡唑基化合物在医疗保健方面也扮演着十分重要的角色, 如环氧合酶-2 选择抑制剂塞来考昔、镇痛药安乃近等 [9,10] .…”

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Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

Dai¹,

Chen²,

Hong³

et al. 2017

Chin. J. Org. Chem.

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In order to explore novel pyrazole derivatives with good biological activities, a series of novel pyrazole oxime ester compounds containing pyridyl moiety were designed and synthesized according to the method of active substructure combination. The structures of the target compounds were determined by 1 H NMR, 13 C NMR and elemental analysis. Preliminary bioassay data indicated that some of the title compounds showed certain insecticidal activities. At a concentration of 500 μg/mL, seven compounds exhibited insecticidal activity against Oriental armyworm with 50%～90%, and six compounds exhibited insecticidal activity against Aphis medicaginis with 50%～90%. When the dosage was lowered to 100 μg/mL, 1,3-dimethyl-5-(4-chlorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5f) and 1,3-dimethyl-5-(4-methylphenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5j) were still active against Aphis medicaginis with inhibitory values of 50% and 50%, respectively. Insecticidal activities against Nilaparvata lugens of 1,3-dimethyl-5-(3-fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5b) and 5f were both 100% at 500 μg/mL. Additionally, 1,3-dimethyl-5-(4fluorophenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5c), 1,3-dimethyl-5-(3-chlorophenoxy)-pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5e), 1,3-dimethyl-5-(4-trifluoromethoxyphenoxy)pyrazole-4-formyl-O-(2-chloropyridin-3-formyl)oxime (5i) and 5j displayed good anti-tumor activity against HepG2 cells with IC 50 values of 2.6, 4.6, 1.8和 1.1 μmol/L, respectively.

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Development of a New Acaricide, Fenpyroximate

Cited by 27 publications

References 0 publications

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

5-Chloro-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

Synthesis and Biological Activities of Novel Pyrazole Oxime Derivatives Bearing an Oxazole Moiety

Synthesis and Bioactivities of Novel Pyrazole Oxime Ester Derivatives Containing Pyridyl Moiety

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