Vectorizing Pro-Insecticide: Influence of Linker Length on Insecticidal Activity and Phloem Mobility of New Tralopyril Derivatives
Abstract
:1. Introduction
2. Materials and Methods
2.1. Synthesis
2.1.1. General Information for Synthesis
2.1.2. Synthesis of Compound 4
2.1.3. General Procedures for Compounds 14–22
2.1.4. General Procedures for Compounds 23–31
2.1.5. Synthesis of Compounds 33–41
2.1.6. Synthesis of Conjugates 42–50
2.2. Insecticidal Activity of Nine Conjugates against P. xylostella
2.3. Sap Collection from Ricinus communis L. Seedlings and Analysis
2.4. Metabolism of Conjugates 42 and 43 in P. xylostella
2.5. Physicochemical Properties
3. Results and Discussion
3.1. Synthesis and Characterization
3.2. Insecticidal Activity
3.3. Phloem Mobility of Conjugates
3.4. Metabolism of Conjugates 42 and 43 in P. xylostella
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Conflicts of Interest
References
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Concentration | ||||
---|---|---|---|---|
2 mM | 1 mM | 0.5 mM | 0.1 mM | |
42 | 100.00 ± 0.00 a | 100.0 ± 0.00 a | 100.00 ± 0.00 a | 43.33 ± 0.15 b |
43 | 100.00 ± 0.00 a | 100.00 ± 0.00 a | 76.66 ± 0.15 b | 0.00 ± 0.00 c |
44 | 100.00 ± 0.00 a | 100.00 ± 0.00 a | 73.33 ± 0.12 b | 0.00 ± 0.00 c |
45 | 100.00 ± 0.00 a | 100.00 ± 0.00 a | 60.00 ± 0.26 c | 0.00 ± 0.00 c |
46 | 100.00 ± 0.00 a | 83.33 ± 0.12 b | 48.33 ± 0.19 c | 0.00 ± 0.00 c |
47 | 100.00 ± 0.00 a | 23.33 ± 0.12 c | 3.33 ± 0.06 d | 0.00 ± 0.00 c |
48 | 100.00 ± 0.00 a | 3.33 ± 0.058 d | 0.00 ± 0.00 d | 0.00 ± 0.00 c |
49 | 100.00 ± 0.00 a | 0.00 ± 0.00 d | 0.00 ± 0.00 d | 0.00 ± 0.00 c |
50 | 100.00 ± 0.00 a | 0.00 ± 0.00 d | 0.00 ± 0.00 d | 0.00 ± 0.00 c |
Chlorfenapyr | 100.00 ± 0.00 a | 100.00 ± 0.00 a | 100.00 ± 0.00 a | 100.00 ± 0.00 a |
LC50 | SE | 95% Confidence Limits | |
---|---|---|---|
42 | 0.2397 mM | 0.0366 | 0.1644 mM–0.3494 mM |
43 | 0.4413 mM | 0.0647 | 0.3311 mM–0.5882 mM |
44 | 0.4400 mM | 0.0624 | 0.3309 mM–0.5849 mM |
45 | 0.4602 mM | 0.0655 | 0.3479 mM–0.6087 mM |
Chlorfenapyr | 0.0249 mM | 0.0145 | 0.0079 mM–0.0784 mM |
Tralopyril | 0.0224 mM | 0.0601 | 0.0133 mM–0.0381 mM |
Concentration in Phloem Sap (μM) | |
---|---|
42 | 24.8493 ± 0.6730 d |
43 | 41.887 ± 0.4591 a |
44 | 36.7447 ± 0.6832 b |
45 | 30.5837 ± 1.9420 c |
chlorfenapyr | 0.00 e |
Feature | MW (D) | logP | pKa | HBD | HBA |
---|---|---|---|---|---|
Tralopyril | 349.53 | 4.02 | 14 b | 1 | 2 |
Chlorfenapyr | 407.61 | 4.76 | 14 | 0 | 3 |
42 | 633.81 | 3.00 | 3.91 | 3 | 11 |
43 | 647.83 | 3.22 | 3.92 | 3 | 11 |
44 | 661.86 | 3.52 | 3.92 | 3 | 11 |
45 | 675.88 | 3.76 | 3.92 | 3 | 11 |
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Li, T.X.; Chen, Y.; Liu, H.F.; Ma, C.Y.; Yang, W. Vectorizing Pro-Insecticide: Influence of Linker Length on Insecticidal Activity and Phloem Mobility of New Tralopyril Derivatives. Molecules 2021, 26, 4570. https://doi.org/10.3390/molecules26154570
Li TX, Chen Y, Liu HF, Ma CY, Yang W. Vectorizing Pro-Insecticide: Influence of Linker Length on Insecticidal Activity and Phloem Mobility of New Tralopyril Derivatives. Molecules. 2021; 26(15):4570. https://doi.org/10.3390/molecules26154570
Chicago/Turabian StyleLi, Tian Xing, Yao Chen, Hui Fang Liu, Chi Yu Ma, and Wen Yang. 2021. "Vectorizing Pro-Insecticide: Influence of Linker Length on Insecticidal Activity and Phloem Mobility of New Tralopyril Derivatives" Molecules 26, no. 15: 4570. https://doi.org/10.3390/molecules26154570