Design, Synthesis, Biological Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moieties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
No. | Method | Time | condition | Yield/% |
---|---|---|---|---|
2 | No-MW | 24 h | r.t. | 88 |
MW | 4 min | 200 W | 95 | |
3 | No-MW | 5 h | reflux | 90 |
MW | 1 min | 500 W | 96 |
2.2. Herbicidal Activities
No. | R | CRC | Ech. | Bra. | Dig. | Ama. | ||||
---|---|---|---|---|---|---|---|---|---|---|
Pre- | Post- | Pre- | Post- | Pre- | Post- | Pre- | Post- | |||
4a | cyclopropyl | −100 | 6.2 | 15.0 | 92.9 | 100 | 72.5 | 30.0 | 100 | 100 |
4b | phenyl | −100 | 5.4 | 26.3 | 86.9 | 100 | 52.9 | 20.0 | 100 | 100 |
4c | p-nitrophenyl | −100 | 0 | 10.0 | 71.7 | 100 | 21.6 | 0 | 100 | 100 |
4d | p-chlorophenyl | −100 | 19.5 | 18.9 | 11.2 | 100 | 53.7 | 10.7 | 91.6 | 100 |
4e | p-fluorophenyl | −100 | 0 | 28.5 | 12.4 | 100 | 100 | 0 | 95.8 | 100 |
4f | m-methylphenyl | −100 | 12.1 | 27.3 | 32.0 | 100 | 11.1 | 7.1 | 91.6 | 100 |
4g | m-chlorophenyl | −100 | 0 | 6.5 | 33.7 | 100 | 16.7 | 21.4 | 87.4 | 100 |
4h | o-fluorophenyl | −100 | 11.6 | 19.4 | 100 | 100 | 37.0 | 21.5 | 89.5 | 100 |
4i | o-chlorophenyl | −100 | 9.1 | 22.3 | 64.5 | 100 | 64.8 | 7.1 | 91.6 | 100 |
4j | 2,4-dichlorophenyl | −100 | 21.0 | 0 | 56.8 | 100 | 50.0 | 0 | 78.9 | 100 |
4k | o-methoxyphenyl | −100 | 0 | 21.7 | 49.1 | 100 | 22.2 | 3.6 | 81.1 | 100 |
4l | p-methoxyphenyl | −100 | 16.6 | 20.0 | 62.1 | 100 | 48.1 | 21.4 | 100 | 100 |
4m | p-iodophenyl | −100 | 23.5 | 0 | 52.1 | 100 | 3.7 | 3.6 | 70.5 | 100 |
4n | 5-methylisoxazole-4-yl | −100 | 8.1 | 9.1 | 100 | 100 | 38.9 | 0 | 78.9 | 100 |
4o | 1-CN-cyclopropyl | −100 | 20.5 | 14.9 | 14.8 | 100 | 0 | 17.9 | 49.5 | 100 |
4p | propyl | −100 | 100 | 27.9 | 100 | 100 | 87.0 | 28.6 | 100 | 100 |
4q | isopropyl | −100 | 100 | 20.0 | 100 | 100 | 70.4 | 21.4 | 83.2 | 100 |
4r | 2,4-dichlorophenoxymethyl | −63.5 | 100 | 7.6 | 18.3 | 58.6 | 25.9 | 0 | 78.9 | 100 |
4s | (2-(2,4-dichlorophenoxy)-acetyl)propyl | −100 | 5.6 | 0 | 56.2 | 100 | 87.0 | 3.6 | 87.4 | 100 |
4t | furan | −100 | 0 | 7.6 | 100 | 100 | 63.0 | 17.9 | 85.3 | 100 |
4u | (2 E,4Z)-hexa-2,4-diene- | −100 | 100 | 31.8 | 100 | 100 | 31.5 | 0 | 93.7 | 100 |
4v | 3-pyridine | −100 | 100 | 20.0 | 100 | 100 | 25.9 | 0 | 100 | 100 |
4w | 4-pyridine | −100 | 100 | 17.2 | 100 | 100 | 66.7 | 10.7 | 83.2 | 100 |
4x | Methyl | −100 | 68.2 | 26.2 | 88.8 | 100 | 87.0 | 0 | 70.5 | 100 |
2,4-D | 65.7 | 100 | 85.4 | 100 | 100 | 100 | 100 | 81.1 | 100 |
No. | Rate g/ha | Ech. | Bra. | Dig. | Ama. | ||||
---|---|---|---|---|---|---|---|---|---|
Pre | Post | Pre | Post | Pre | Post | Pre | Post | ||
4a | 187.5 | 0 | 37.7 | 55.7 | 100 | 0 | 8.3 | 100 | 100 |
375 | 0 | 50.4 | 53.3 | 100 | 0 | 12.7 | 100 | 100 | |
750 | 0 | 61.2 | 59.1 | 100 | 89.0 | 31.5 | 100 | 100 | |
2,4-D | 187.5 | 0 | 0 | 0 | 100 | 0 | 0 | 0 | 100 |
375 | 0 | 0 | 0 | 100 | 0 | 0 | 52.4 | 100 | |
750 | 32.6 | 32.4 | 0 | 100 | 50.0 | 0 | 78.6 | 100 |
2.3. Plant Growth Regulatory Activity
2.4. CoMFA Analysis
method | q2 | r2 | S | F | No. | Contributor (%) | |
---|---|---|---|---|---|---|---|
Steric | Electrostatic | ||||||
CoMFA | 0.57 | 0.886 | 0.435 | 97.628 | 4f | 66.9% | 33.1% |
3. Experimental
3.1. Instruments
3.2. General Procedure
3.3. 3D-QSAR Analysis
No. | R | pIC50 | pIC50' | Residue |
---|---|---|---|---|
4a | cyclopropyl | −2.06064 | −2.1257 | 0.06506 |
4b | phenyl | −2.47998 | −2.5328 | 0.05282 |
4c | p-nitrophenyl | −3.14439 | −3.0982 | −0.04619 |
4d | p-chlorophenyl | −2.50804 | −2.5895 | 0.08146 |
4e | p-fluorophenyl | −0.55723 | −0.6172 | 0.05997 |
4f * | m-methylphenyl | −3.4516 | −3.5621 | 0.1105 |
4g | m-chlorophenyl | −3.27036 | −3.5229 | 0.25254 |
4h | o-fluorophenyl | −2.784 | −2.8013 | 0.0173 |
4i | o-chlorophenyl | −2.3074 | −2.4085 | 0.1011 |
4j # | 2,4-dichlorophenyl | −2.61072 | −2.8691 | 0.25838 |
4k | o-methoxyphenyl | −3.11189 | −3.0097 | −0.10219 |
4l | p-methoxyphenyl | −2.60028 | −2.4112 | −0.18908 |
4m | p-iodophenyl | −4.08294 | −4.1954 | 0.11246 |
4n | 5-methylisoxazole-4-yl | −2.73284 | −2.6376 | −0.09524 |
4o | 1-CN-cyclopropyl | −4.51171 | −4.2652 | −0.24651 |
4p # | propyl | −1.65895 | −1.6622 | 0.00325 |
4q | isopropyl | −2.10825 | −2.3056 | 0.19735 |
4r | 2,4-dichlorophenoxymethyl | −3.09808 | −3.2077 | 0.10962 |
4s | (2-(2,4-dichlorophenoxy)acetyl)propyl | −1.82968 | −1.9661 | 0.13642 |
4t | furan | −2.28624 | −2.1627 | −0.12354 |
4u | (2E,4Z)- hexa-2,4-diene- | −2.85481 | −2.6382 | −0.21661 |
4v # | 3-pyridine | −2.9882 | −2.7025 | −0.2857 |
4w | 4-pyridine | −2.23 | −2.3669 | 0.1369 |
3.4. Herbicidal Activities Assay
3.5. Plant Growth Regulatory Activity Assay
4. Conclusions
Acknowledgments
Conflicts of Interest
References
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Sun, G.-X.; Sun, Z.-H.; Yang, M.-Y.; Liu, X.-H.; Ma, Y.; Wei, Y.-Y. Design, Synthesis, Biological Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moieties. Molecules 2013, 18, 14876-14891. https://doi.org/10.3390/molecules181214876
Sun G-X, Sun Z-H, Yang M-Y, Liu X-H, Ma Y, Wei Y-Y. Design, Synthesis, Biological Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moieties. Molecules. 2013; 18(12):14876-14891. https://doi.org/10.3390/molecules181214876
Chicago/Turabian StyleSun, Guo-Xiang, Zhao-Hui Sun, Ming-Yan Yang, Xing-Hai Liu, Yi Ma, and Yun-Yang Wei. 2013. "Design, Synthesis, Biological Activities and 3D-QSAR of New N,N'-Diacylhydrazines Containing 2,4-Dichlorophenoxy Moieties" Molecules 18, no. 12: 14876-14891. https://doi.org/10.3390/molecules181214876