Design, synthesis, and insecticidal/acaricidal evaluation of novel pyrimidinamine derivatives containing phenyloxazole moiety

Zhang, Ning; Huang, Mingzhi; Liu, Aiping; Liu, Min-Hua; Li, Lizhong; Zhou, Chun-Ge; Ren, Yulin; Ou, Xiaoming; Long, Chuyun; Sun, Jiong; Dang, Mingming; Zhi-li, Lan

doi:10.1007/s11696-019-00932-5

Cited by 14 publications

(12 citation statements)

References 27 publications

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“…In summary, 17 novel N-phenylbenzamide derivatives containing a trifluoromethylpyrimidine moiety were prepared, and their structures were confirmed by 1 H NMR, 13 C NMR, and HRMS. Biological activity results indicated that most of the target compounds exhibited moderate to good antifungal and insecticidal activities.…”

Section: Discussionmentioning

confidence: 95%

“…e reaction was carried out at room temperature for 8-10 h. After the completion of the reaction, the solvent was evaporated under vacuum condition and then the residue was recrystallized from ethanol to give pure target compounds 4a-4q. e physical characteristics, 1 H NMR, 13 C NMR, and HRMS data for all the target compounds are shown in Supplementary Materials.…”

Section: General Procedures For the Preparation Of The Target Compounds (4a-4q)mentioning

confidence: 99%

“…Pyrimidine is one of best important chemical scaffolds for application in pesticide chemistry, medicinal chemistry, and material chemistry. Many of pyrimidine derivatives play an important role of bioactive compounds, such as antifungal [9,10], antibacterial [11,12], acaricidal [13,14] insecticidal [15,16], herbicidal [17,18], and antiviral [19,20] activities. Meanwhile, N-phenylbenzamide, a key active fragment in pesticide chemistry, is usually used as a pesticide active fragment and exhibit extensive biological activities, such as antiviral, antifungal, antibacterial, herbicidal, and insecticidal activities [21].…”

Section: Introductionmentioning

confidence: 99%

“…9 Hz, 2H, Ph-H);13 C NMR (150 MHz, DMSO-d 6 , ppm) δ 170.38, 165.13, 159.74, 156.24 (q, J � 35.60 Hz), 154.57, 135.94, 133.17, 130.07, 122.59, 122.52, 122.17, 121.92, 121.82 (q, J � 272.30 Hz), 115.79, 115.57, 107.03; HRMS (ESI) calcd. for C 18 H 12 F 4 N 3 O 2 [M + H] + : 378.3061, found: 378.0851.…”

mentioning

confidence: 99%

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Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

Lan

Chen

et al. 2021

Journal of Chemistry

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Seventeen novel N-phenylbenzamide derivatives bearing a trifluoromethylpyrimidine moiety were synthesized via four-step reactions. Their antifungal and insecticidal properties were evaluated. Antifungal test results demonstrated that some of the synthesized compounds showed better in vitro bioactivities against Phomopsis sp., Botryosphaeria dothidea (B. dothidea), and Botrytis cinerea (B. cinerea) at 50 μg/mL than pyrimethanil. Unfortunately, the synthesized compounds revealed lower insecticidal activities against Spodoptera frugiperda (S. frugiperda) and Mythimna separata (M. separata) at 500 μg/mL than chlorantraniliprole.

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Section: Discussionmentioning

confidence: 95%

Section: General Procedures For the Preparation Of The Target Compounds (4a-4q)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

Lan

Chen

et al. 2021

Journal of Chemistry

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“…Pyrimidine is a classic nitrogen-containing heterocycle in natural products, such as caffeine, uracil, variolin B, thymine, cytosine, vitamin B1, theophylline, and heteromine. More importantly, reported synthetic pyrimidine compounds have diverse activities, such as fungicidal [1], antitumor [2], antioxidant [3], insecticidal [4], acaricidal [5], and anti-HIV activities [6]. Some of them have been developed as commercial pesticides or pharmaceuticals, especially for pyridineamine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif

Wen

et al. 2021

Front. Chem. Sci. Eng.

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Twenty six novel pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif were synthesized. Their chemical structures were confirmed by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and highresolution mass spectrography. The insecticidal activity results indicated that some of them possessed excellent insecticidal activity (100%) against Mythimna separate, especially for compounds 6d, 6f, 6o, 6w, 6y and 6z. These compounds exhibited no activity against the insects Aphis medicagini and Tetranychus cinnabarinus. The structureinsecticidal activity relationships are discussed. Density functional theory analysis can potentially be used to design more active compounds. These results provide useful insecticide design information for further optimization.

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Room‐Temperature Dialkylamination of Chloroheteroarenes Using a Cu(II)/PTABS Catalytic System

Shet

Patel

Waikar

et al. 2022

Chemistry An Asian Journal

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The dimethylamino functionality has significant importance in industrially relevant molecules and methodologies to install these efficiently are highly desirable. We report herein a highly efficient, room‐temperature dimethylamination of chloroheteroarenes performed via the in‐situ generation of dimethylamine using N,N‐dimethylformamide (DMF) as precursor wiith a large substrate scope that includes various heteroarenes, purines as well as commercially relevant drugs such as altretamine, ampyzine and puromycin precursor.

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Design, synthesis, and insecticidal/acaricidal evaluation of novel pyrimidinamine derivatives containing phenyloxazole moiety

Cited by 14 publications

References 27 publications

Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

Synthesis and Antifungal and Insecticidal Activities of Novel N-Phenylbenzamide Derivatives Bearing a Trifluoromethylpyrimidine Moiety

Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif

Room‐Temperature Dialkylamination of Chloroheteroarenes Using a Cu(II)/PTABS Catalytic System

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