Synthesis and fungicidal activities of novel benzothiophene-substituted oxime ether strobilurins

Song, Tao; Xie, Yaqiang; Gui, Sizhe; Ye, Liyi; Huang, Zilong; Huang, Yibing; Che, Liming

doi:10.1016/j.bmcl.2014.03.024

Cited by 30 publications

(13 citation statements)

References 20 publications

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“…For the synthesis of starting materials 1 a-h, protocols already described were used, with minor modifications. [19,26] Thus, initially 3-bromo-2-(alkylthio)pyridines 5 a-f were previously synthesized from 3-bromo-2-chloropyridines 4 a-d, followed by the Sonogashira cross-coupling reaction, producing the 3-(arylethynyl)-2-(alkylthio)pyridines 1 a-h (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2‐Aryl‐(3‐Organochalcogenyl)Thieno[2,3‐b]Pyridines Promoted by Oxone®

et al. 2021

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We describe herein an alternative method for the synthesis of 2-aryl-(3-organochalcogenyl)thieno[2,3-b] pyridines through the electrophilic cyclization of 3-(arylethynyl)-2-(alkylthio)pyridines promoted by electrophilic species of organochalcogen compounds. These species were generated in situ by the oxidative cleavage of chalcogen-chalcogen (Se, Te) bond of diorganyl dichalcogenides using Oxone® in ethanol as solvent in an open-flask at 78°C. The protocol allowed the synthesis of highly substituted thieno [2,3-b] pyridines starting from several diorganyl dichalcogenides and 3-(arylethynyl)-2-(alkylthio)pyridines, obtaining 21 new compounds in good to excellent yields (70-99%). Still, the method showed good efficiency on the gram-scale synthesis. In addition, several synthetic transformations such as oxidation, selenylation and hydrogenation reactions were demonstrated.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 2‐Aryl‐(3‐Organochalcogenyl)Thieno[2,3‐b]Pyridines Promoted by Oxone®

et al. 2021

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“…As shown in Scheme 1, in the presence of piperidine, spirodiclofen enol ( 4 ) was smoothly produced from spirodiclofen ( 1 ) by removal of C‐4 ester group 22,23 . Then 21 target compounds 5a – 5u were obtained in 40–93% yields by reaction of an intermediate 4 with different halogenated hydrocarbons or methane sulfonates 24 . Their structures were characterized by IR, 1 H‐NMR, and m,p, values (see Supporting Information, Table S1).…”

Section: Resultsmentioning

confidence: 99%

Spirodiclofen ether derivatives: semisynthesis, structural elucidation, and pesticidal activities against Tetranychus cinnabarinusBoisduval, Aphis citricolaVan der Goot and Mythimna separataWalker

et al. 2021

Pest Management Science

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BACKGROUND Spirodiclofen is a spirocyclic tetronic acid‐type acaricidal agent. Nowadays, serious pests resistance to spirodiclofen and cross‐resistance to other acaricides has appeared. To overcome pests resistance and discover new potential agrochemicals, a series of ether derivatives were prepared based on spirodiclofen as a lead compound. Their pesticidal activities were investigated against three typically agricultural pests, Mythimna separata Walker, Aphis citricola Van der Goot and Tetranychus cinnabarinus Boisduval. RESULTS Four steric structures of compounds 5e, 5f, 5i and 5j were determined by single‐crystal X‐ray diffraction. Against T. cinnabarinus, compounds 5b, 5f and 5l exhibited potent acaricidal activity, and their good control effects in the glasshouse were observed when compared with spirodiclofen, especially the control efficiency of compound 5b was comparable to that of spirodiclofen; against M. separata, compound 5j showed > 1.8‐fold potent insecticidal activity of spirodiclofen; against A. citricola, compounds 5d and 5j displayed > 2.0‐fold potent aphicidal activity of spirodiclofen. The relationships between their structures and agricultural activities were also discussed. CONCLUSION Compounds 5b and 5d could be further studied as acaricidal and aphicidal agents, respectively; compound 5j can be considered as a lead compound for the insecticidal and aphicidal activities. This will pave the way for future application of these derivatives as pesticide substitutes for spirodiclofen. © 2021 Society of Chemical Industry

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“…Several synthetic oximes with antifungal properties have been reported [25]. Maize plant cytochrome P450 forms oximes from their aminoacids; phenylacetaldoxime and indole-3-acetaldoxime [26].…”

Section: Discussionmentioning

confidence: 99%

Isolation, Identification, and Characterization of the Novel Antibacterial Agent Methoxyphenyl-Oxime from Streptomyces pratensis QUBC97 Isolate

Sa¹,

Ayyad²,

Ayesh³

et al. 2017

JOURNAL OF ANTIBIOTICS RESEARCH

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Synthesis and fungicidal activities of novel benzothiophene-substituted oxime ether strobilurins

Cited by 30 publications

References 20 publications

Synthesis of 2‐Aryl‐(3‐Organochalcogenyl)Thieno[2,3‐b]Pyridines Promoted by Oxone®

Synthesis of 2‐Aryl‐(3‐Organochalcogenyl)Thieno[2,3‐b]Pyridines Promoted by Oxone®

Spirodiclofen ether derivatives: semisynthesis, structural elucidation, and pesticidal activities against Tetranychus cinnabarinusBoisduval, Aphis citricolaVan der Goot and Mythimna separataWalker

Isolation, Identification, and Characterization of the Novel Antibacterial Agent Methoxyphenyl-Oxime from Streptomyces pratensis QUBC97 Isolate

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