Synthesis, Acaricidal Activity, and Structure–Activity Relationships of Pyrazolyl Acrylonitrile Derivatives

Yu, Haibo; Chen, Yan; Xu, Man; Song, Yuquan; Luo, Yanmei; Li, Bin

doi:10.1021/acs.jafc.6b04221

Cited by 33 publications

(30 citation statements)

References 21 publications

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“…The pyridine ring and benzene ring are perfect flat planes indicating that carbon atoms from these rings adopt sp 2 hybridization, which is consistent with their aromatic rings (Tables S2–S5). Chlorine atom (Cl1) bonds to a carbon atom (C7) of the benzene ring and the Cl1–C7 distance ranges from 1.730 (2) to 1.744 (2) Å (Tables S2–S5) that matches the ClC single bond length 21,22 …”

Section: Resultsmentioning

confidence: 96%

Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Cong

et al. 2020

Pest Management Science

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BACKGROUND: Pyrisoxazole is a fungicide that has two chiral carbon atoms and four isomers: (3S,5R)-, (3R,5S)-, (3S,5S)-, and (3R,5R)-pyrisoxazole. RESULTS: Pure crystals of four pyrisoxazole isomers were prepared by chiral separation and single-crystal cultivation. Their absolute configurations were established by X-ray single crystal diffraction analysis. Bioassays indicated that compound (3S,5R)-pyrisoxazole showed excellent fungicidal activity with a median effective concentration (EC 50) value of 0.14 ∼g mL −1 and protective activity with an EC 50 value of 13.29 ∼g mL −1. These values are superior to the commercial fungicides boscalid and racemic pyrisoxazole. CONCLUSIONS: The biological activity of racemic pyrisoxazole is due almost exclusively to the isomer (3S,5R)-pyrisoxazole; the other three isomers had very low activity.

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Section: Resultsmentioning

confidence: 96%

Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Cong

et al. 2020

Pest Management Science

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“…In the citrus growing region of South China, SYP-9625 and abamectin are commonly used against different pests, including citrus red mite (Meng, Wang & Jiang, 2002;Fang et al, 2013;Tian, Li & Ran, 2013;Liao et al, 2016;Dou et al, 2017). SYP-9625 is commonly used against phytophagous mites with minimum hazard to animals (Li et al, 2010;Chai et al, 2011;Tian, Li & Ran, 2013;Yu et al, 2016;Liu et al, 2018;Ouyang et al, 2018;Chen et al, 2019). Liu et al (2018) reported that SYP-9625 gave maximum mortality and dispersed against P. cirti in the no-choice test, similar to our results and against Tetranychus citri (Chen et al, 2019).…”

Section: Discussionmentioning

confidence: 99%

Behavioral response ofPanonychus citri(McGregor) (Acari: Tetranychidae) to synthetic chemicals and oils

Qayyoum

Song

Zhang

et al. 2021

PeerJ

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Background Panonychus citri (McGregor) (Acari: Tetranychidae) population outbreaks after the citrus plantation’s chemical application is a common observation. Dispersal behavior is an essential tool to understand the secondary outbreak of P. citri population. Therefore, in the current study, the dispersal activity of P. citri was observed on the leaf surfaces of Citrus reticulata (Rutaceae) treated with SYP-9625, abamectin, vegetable oil, and EnSpray 99. Method Mites were released on the first (apex) leaf of the plant (adaxial surface) and data were recorded after 24 h. The treated, untreated, and half-treated data were analyzed by combining the leaf surfaces (adaxial right, adaxial left, abaxial right, and abaxial left). All experiments were performed in open-air environmental conditions. Results The maximum number of mites was captured on the un-treated or half-treated surfaces due to chemicals repellency. Chemical bioassays of the free-choice test showed that all treatments significantly increased the mortality of P. citri depending on application method and concentration. A significant number of mites repelled away from treated surfaces and within treated surfaces except adaxial left and abaxial right surfaces at LC30. In the no-choice test, SYP-9625 gave maximum mortality and dispersal by oils than others. No significant differences were observed within the adaxial and abaxial except abaxial surface at LC30. Therefore, the presence of tested acaricides interferes with P. citri dispersal within leaf surfaces of plantations depending on the mites released point and a preferred site for feeding.

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“…19 Safeners, having structural features closely resembling those of herbicides, may interfere in the metabolism of herbicides that protect crops. 20 In recent years, the active substructure combination has become an effective method for improving the hit of compounds. The safener benzhydryloxy-acetic acid combined with the potential safener 5-phenyl-4,5-dihydroisoxazole-3-ethyl ester led to the production of the strong rice safener isoxadifenethyl.…”

Section: Introductionmentioning

confidence: 99%

Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

Zhai

et al. 2018

RSC Adv.

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Synthesis, Acaricidal Activity, and Structure–Activity Relationships of Pyrazolyl Acrylonitrile Derivatives

Cited by 33 publications

References 21 publications

Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Absolute configuration of four chiral isomers of pyrisoxazole and their bioactivity

Behavioral response ofPanonychus citri(McGregor) (Acari: Tetranychidae) to synthetic chemicals and oils

Design, microwave-assisted synthesis, bioactivity and SAR of novel substituted 2-phenyl-2-cyclohexanedione enol ester derivatives

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