scholarly journals Semisynthesis of some matrine ether derivatives as insecticidal agents

RSC Advances ◽  
2017 ◽  
Vol 7 (26) ◽  
pp. 15997-16004 ◽  
Author(s):  
Jiu-Lin Huang ◽  
Min Lv ◽  
Hui Xu

Compounds 4i and 4k exhibited more potent insecticidal activities than matrine against Plutella xylostella and Mythimna separata. These matrine derivatives may be considered as promising insecticidal candidates.

2010 ◽  
Vol 5 (3) ◽  
pp. 1934578X1000500
Author(s):  
Shaopeng Wei ◽  
Minchang Wang ◽  
Zhiqin Ji ◽  
Baojun Shi ◽  
Shengkun Li ◽  
...  

Three new insecticidal sesquiterpene polyol esters with dihydro-β-agarofuran skeletons, Kupiteng esters A (1), B (2) and C (3), were isolated from the methanol extracts of the root bark of Celastrus angulatus and their structures elucidated by analyses of MS and NMR spectral data. The insecticidal activities of these compounds against the 4th instar larvae of Mythimna separata were evaluated. The KD50 values of compounds 1-3, were 260.2, 445.5 and 1260.0 μg-g−1, respectively.


Toxins ◽  
2014 ◽  
Vol 6 (8) ◽  
pp. 2453-2470 ◽  
Author(s):  
Ming-Lun Chen ◽  
Pin-Hsin Chen ◽  
Jen-Chieh Pang ◽  
Chia-Wei Lin ◽  
Chin-Fa Hwang ◽  
...  

2014 ◽  
Vol 9 (6) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Jiwen Zhang ◽  
Lihui Cui ◽  
Longbo Li ◽  
Zhan Hu ◽  
Qianliang Zhang ◽  
...  

In order to develop new biorational pesticides and clarify the potential structural factors needed for the biological activity of celangulin-V analogues, thirty novel nitrogenous derivatives were designed and synthesized. The single crystal structure of celangulin-V is reported for the first time and provides a more accurate structure than that previously reported. The structures of all the new derivatives were confirmed by either NMR or ESI-MSn analysis. Insecticidal activities of these compounds were tested against the third-instar larvae of Mythimna separata. One derivative (1–6) showed higher insecticidal activity than celangulin-V, with a KD50 of 231.2 μg.g–1, while two compounds (2–13 and 2–14) exhibited lower insecticidal activities; the others revealed no activity at a concentration of 20 mg mL−1. The results support the view that celangulin-V has the potential to be a lead structure of semi-synthetic green insecticides.


Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 562 ◽  
Author(s):  
Qi-Bo Li ◽  
Min Liao ◽  
Qing Liu ◽  
Tong Feng ◽  
Zhi-Yuan Xu ◽  
...  

New 1,3,5-trimethylpyrazole-containing malonamide derivatives based on pyflubumide were designed, synthesized, and characterized using 1H-NMR, 13C-NMR, and high-resolution mass spectra (HRMS). The results of preliminary bioassays showed that the target compounds possessed good activities against Tetranychus cinnabarinus, Plutella xylostella, and Aphis craccivora. Most of the target compounds exhibited moderate to good acaricidal activity against Tetranychus cinnabarinus at a concentration of 400 µg/mL, and some showed moderate activity at a concentration of 200 µg/mL; in particular, compounds 8m and 8p exhibited 70.0% mortality. In addition, some of the target compounds exhibited good insecticidal activities against Plutella xylostella at a concentration of 200 µg/mL, especially compounds 8i and 8o, which achieved 100.0% mortality at a concentration of 100 µg/mL. Interestingly, some of the target compounds exhibited potent anti-aphid activity against Aphis craccivora at a concentration of 200 µg/mL; furthermore, compounds 8p and 8q demonstrated 100.0% anti-aphid activity at a concentration of 50 µg/mL. The preliminary analyses of the structure–activity relationships (SAR) indicated that the acaricidal and insecticidal activities varied significantly depending on the type of substituent and substitution pattern, which provides guidance for the further investigation of such structural modifications.


2019 ◽  
Vol 15 (1) ◽  
pp. 98-102
Author(s):  
Wenda Wang ◽  
Haihuan Su ◽  
Huangyong Li ◽  
Xiufang Cao

Background: Using constantly and widely chemistry insecticides has resulted in a selection burden and favored tolerance development in various insect species. Particularly, pyrethroids are the only one which can be used for net impregnation either ITNs or LLIN as yet, however, the excessive use of pyrethroids has led to many cases of insect resistance in worldwide. Therefore, it is urgent to develop novel insecticides fighting against this sort of resistance. Methods: Based on the preliminary studies, we explored a straightforward highly stereoselective method to achieve the novel chiral ester derivatives by using Oppolzer’s 10,2-camphorsultam as chiral controlling reagent. Results: A series of tetrafluorobenzyl alcohol oriented (S)-enantiomeric esters were designed and synthesized by the asymmetric synthesis. All the compounds exhibited moderate yields, and the original synthesized compounds have been evaluated for their potential insecticidal activity against Plutella xylostella compared with those of fenvalerate and D-trans-phenothrin, and some compounds presented excellent insecticidal activities. Conclusion: The bioassay illustrated that some of the compounds exhibit obviously insecticidal activities against Plutella xylostella, especially, the insecticidal activity of compound 5i was as good as commercial fenvalerate and D-trans-phenothrin, which can be used as a lead compound for further optimization.


Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1976 ◽  
Author(s):  
Yankai Li ◽  
Jiaqi Wei ◽  
Jiameng Fang ◽  
Wenbo Lv ◽  
Yufei Ji ◽  
...  

A new lignan (T4) and three known lignans (T1, T2, and T3) were isolated from the methanol extract of the roots of Phryma leptostachya using bioassay-guided method, and their structures were identified as phrymarolin I (T1), II (T2), haedoxan A (T3), and methyl 4-((6a-acetoxy-4-(6-methoxybenzo[d][1,3]dioxol-5-yl)tetrahydro-1H,3H-furo[3,4–c]furan-1-yl)oxy)-1-hydroxy-2,2-dimethoxy-5-oxocyclopent-3-ene-1-carboxylate (T4) byNMR and ESI-MS spectral data. Bioassay results revealed that haedoxan A exhibited remarkably high insecticidal activity against Mythimna separata with a stomach toxicity LC50 value of 17.06 mg/L and a topical toxicity LC50 value of 1123.14 mg/L at 24 h, respectively. Phrymarolin I and compound T4 also showed some stomach toxicity against M. separata with KD50 values of 3450.21 mg/L at 4 h and 2807.10 mg/L at 8 h, respectively. In addition, phrymarolin I and haedoxan A exhibited some stomach toxicity against Plutella xylostella with an LC50 value of 1432.05 and 857.28 mg/L at 48 h, respectively. In conclusion, this study demonstrated that lignans from P. leptostachya are promising as a novel class of insecticides or insecticide lead compounds for developing botanical pesticides.


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