Novel Anthranilic Diamides as Potent Ryanodine Receptor Activator
Chin. J. Chem.
pyrazole-5-carboxylic acid was synthesized according to the liter-
ature. The compounds 1 and 2 were prepared referring to the
known procedure.[4] Detailed synthetic procedures and spectral
data for title compounds 3, 4 a–q, 5 a–q, I a–s, and II a–q were
given in the Supporting Information.
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Bioactivities assay
Larvicidal activity of compounds I a–s and II a–q against ori-
ental armyworm (M. separata) and diamondback moth (P. xylos-
tella) was performed on testing organism reared in greenhouse.
o
The bioassay was reduplicative at 25 ± 1 C according to the re-
quirements of statistics. Evaluation results were got by a dead/
alive basis, and death rates were corrected by applying Abbott’s
formula[41] with chlorantraniliprole used as positive control. The
methods were given in the Supporting Information.
Calcium imaging
Calibration of the fluorescence signal was obtained using the
procedure developed by Takahashi et al. with minor modifica-
tions.[42] The attached neurons were rinsed in standard physio-
logical saline [(mmol∙L–1) 150 NaCl, 4 KCl, 2 MgCl2, 2 CaCl2, 10
o
HEPES, buffered to pH 7.0] and then incubated in dark at 28 C in
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standard external saline containing the dye Fluo-3 AM (Sigma, 10
μmol∙L–1). After dye loading, cells were rinsed again in physiologi-
cal saline twice.
Each experiment was replicated at least six times. The data
were analyzed by using SPSS Inc., version 17.0, and Origin, version
8.0 (Origin Lab Corp., Northampton, MA, USA). Results were ex-
pressed as the mean ± SD (n = number of cells). Fluorescence
values were expressed as F/F0, with F0 being the resting (or base-
line) fluorescence and F the change in fluorescence from baseline
after drug application.[43]
[15] Zhang, X.; Li, Y.; Ma, J.; Zhu, H.; Wang, B.; Mao, M.; Xiong, L.; Li, Y.; Li,
Z. Synthesis and insecticidal evaluation of novel anthranilic diamides
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Supporting Information
The supporting information for this article is available on the
[16] Wang, B. L.; Zhu, H. W.; Ma, Y.; Xiong, L. X.; Li, Y. Q.; Zhao, Y.; Zhang,
J. F.; Chen, Y. W.; Zhou, S.; Li, Z. M. Synthesis, insecticidal activities,
and SAR studies of novel pyridylpyrazole acid derivatives based on
amide bridge modification of anthranilic diamide insecticides. J. Agric.
Food Chem. 2013, 61, 5483–5493.
Acknowledgement
This work was supported by the NSFC/China (No. 21502229)
and Tianjin Natural Science Foundation (No. 16JCYBJC29400).
[17] Zhang, J. F.; Xu, J. Y.; Wang, B. L.; Li, Y. X.; Xiong, L. X.; Li, Y. Q.; Ma, Y.;
Li, Z. M. Synthesis and insecticidal activities of novel anthranilic dia-
mides containing acylthiourea and acylurea. J. Agric. Food Chem.
2012, 60, 7565–7572.
[18] Zhou, Y.; Feng, Q.; Di, F.; Liu, Q.; Wang, D.; Chen, Y.; Xiong, L.; Song,
H.; Li, Y.; Li, Z. Synthesis and insecticidal activities of 2,3-dihydro-
quinazolin-4(1H)-one derivatives targeting calcium channel. Bioorg.
Med. Chem. 2013, 21, 4968–4975.
[19] Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Yuan, J.; Yang, G.; Xu, T.
M.; Peng, W. L. Synthesis, nematocidal activity and docking study of
novel chiral 1-(3-chloropyridin-2-yl)-3-(trifluoromethyl)-1H-pyrazole-
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[20] Jeanguenat, A.; Durieux, P.; Edmunds, A. J. F.; Hall, R. G.; Hughes, D.;
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Crossthwaite, A. Bicyclic heterocyclic anthranilic diamides as
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