Citation: Zhou Shaa, Zhou Sha, Xie Yongtao, Meng Xiangde, Wang Baolei, Xiong Lixia, Yang Na, Li Zhengming. Synthesis, insecticidal activities and SAR studies of novel anthranilic diamides containing trifluoroethoxyl substituent and chiral amino acid moieties[J]. Chinese Chemical Letters, ;2018, 29(8): 1254-1256. doi: 10.1016/j.cclet.2017.10.022 shu

Synthesis, insecticidal activities and SAR studies of novel anthranilic diamides containing trifluoroethoxyl substituent and chiral amino acid moieties

State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China

Corresponding author: Li Zhengming, nkzml@vip.163.com
Received Date: 7 August 2017
Revised Date: 16 October 2017
Accepted Date: 18 October 2017
Available Online: 1 August 2017

Figures(1)

Ryanodine receptors (RyRs) activator has become one class of popular insecticide because of its unique mode of action. In order to find more new RyRs activators as insecticidal agents, a series of 18 novel chiral anthranilic diamides were designed by introducing the _D-alanine acid and _D-serine acid esters as well as trifluoroethoxyl group into the anthranilic diamide skeleton and synthesized successfully based on anthranilic diamide and FKI-1033 structures. The structures of the title compounds Ⅰa-i and Ⅱa-i were confirmed by melting points, ¹H NMR, ¹³C NMR, elemental analysis and specific optical rotation analysis. The preliminary bioassay results indicated that most of the title compounds exhibited considerable larvicidal activities against oriental armyworm at 10 mg/L, especially Ⅰb, Ⅰe and Ⅱh showed remarkable insecticidal activities at 0.5 mg/L. The larvicidal activity against diamondback moth of Ⅰa and Ⅱd were 80% and 90% respectively at 0.0001 mg/L, which was similar to that of chlorantraniliprole. The relationship between structure and insecticidal activity was analyzed to reveal a possible co-regulated effect of the chiral amino acid ester, halogen atom or cyano group, and trifluoroethyloxyl group of the skeleton structures of the title compounds, which will provide useful information for guiding the design and discovery of new RyRs activators and insecticidal agrochemicals.
- Chiral anthranilic diamides,
- Trifluoroethoxyl,
- Synthesis,
- Insecticidal activity,
- Ryanodine receptor
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