Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety
To develop novel 2-cyanoacrylate derivatives with potential bioactivity, a number of 2-cyanoacrylate compounds, including substituted pyrazole or 1,2,3-triazole ring, were designed, prepared, and structurally detected by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and elemental an...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-03-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/28/7/3141 |
| _version_ | 1797607358305665024 |
|---|---|
| author | Yang Wang Yudie Chen Ye Qian Jia Chen Xianchao Du Yujun Shi Baolin Xu Sheng Hua Hong Dai |
| author_facet | Yang Wang Yudie Chen Ye Qian Jia Chen Xianchao Du Yujun Shi Baolin Xu Sheng Hua Hong Dai |
| author_sort | Yang Wang |
| collection | DOAJ |
| description | To develop novel 2-cyanoacrylate derivatives with potential bioactivity, a number of 2-cyanoacrylate compounds, including substituted pyrazole or 1,2,3-triazole ring, were designed, prepared, and structurally detected by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and elemental analysis. The biological assessment displayed that some designed compounds had significant herbicidal activities against <i>Brassica juncea</i>, <i>Chenopodium serotinum</i>, <i>Rumex acetosa</i>, <i>Alopecurus aequalis</i>, <i>Polypogon fugax,</i> and <i>Poa annua</i> at a dosage of 1500 g/ha. Furthermore, some derivatives still expressed satisfactory herbicidal activities against <i>Brassica juncea</i>, <i>Chenopodium serotinum,</i> and <i>Rumex acetosa</i> when the dosage was lowered to 150 g/ha, especially the inhibitory effects of compounds <b>9a</b>, <b>9d</b>, <b>9f</b>, <b>9i</b>, <b>10a</b>, <b>10b</b>, <b>10e</b>, and <b>10n</b> against <i>Brassica juncea</i> were all over 80%, compounds <b>9d</b>, <b>9f</b>, <b>9g</b>, <b>9h</b>, <b>9i</b>, <b>10h</b>, <b>10i</b>, <b>10m</b>, <b>10n</b>, and <b>10o</b> possessed more than 70% inhibition rates against <i>Chenopodium serotinum</i>, and compound <b>9d</b> indicated 70% herbicidal activity against <i>Rumex acetosa</i>. These results provided an important basis for further design and discovery of biologically active 2-cyanoacrylate compounds. |
| first_indexed | 2024-03-11T05:29:56Z |
| format | Article |
| id | doaj.art-a559debd30e348369c11fd6d602c5475 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T05:29:56Z |
| publishDate | 2023-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a559debd30e348369c11fd6d602c54752023-11-17T17:14:07ZengMDPI AGMolecules1420-30492023-03-01287314110.3390/molecules28073141Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl MoietyYang Wang0Yudie Chen1Ye Qian2Jia Chen3Xianchao Du4Yujun Shi5Baolin Xu6Sheng Hua7Hong Dai8College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaCollege of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, ChinaTo develop novel 2-cyanoacrylate derivatives with potential bioactivity, a number of 2-cyanoacrylate compounds, including substituted pyrazole or 1,2,3-triazole ring, were designed, prepared, and structurally detected by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and elemental analysis. The biological assessment displayed that some designed compounds had significant herbicidal activities against <i>Brassica juncea</i>, <i>Chenopodium serotinum</i>, <i>Rumex acetosa</i>, <i>Alopecurus aequalis</i>, <i>Polypogon fugax,</i> and <i>Poa annua</i> at a dosage of 1500 g/ha. Furthermore, some derivatives still expressed satisfactory herbicidal activities against <i>Brassica juncea</i>, <i>Chenopodium serotinum,</i> and <i>Rumex acetosa</i> when the dosage was lowered to 150 g/ha, especially the inhibitory effects of compounds <b>9a</b>, <b>9d</b>, <b>9f</b>, <b>9i</b>, <b>10a</b>, <b>10b</b>, <b>10e</b>, and <b>10n</b> against <i>Brassica juncea</i> were all over 80%, compounds <b>9d</b>, <b>9f</b>, <b>9g</b>, <b>9h</b>, <b>9i</b>, <b>10h</b>, <b>10i</b>, <b>10m</b>, <b>10n</b>, and <b>10o</b> possessed more than 70% inhibition rates against <i>Chenopodium serotinum</i>, and compound <b>9d</b> indicated 70% herbicidal activity against <i>Rumex acetosa</i>. These results provided an important basis for further design and discovery of biologically active 2-cyanoacrylate compounds.https://www.mdpi.com/1420-3049/28/7/31412-cyanoacrylatepyrazole1,2,3-triazolesynthesisbiological activity |
| spellingShingle | Yang Wang Yudie Chen Ye Qian Jia Chen Xianchao Du Yujun Shi Baolin Xu Sheng Hua Hong Dai Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety Molecules 2-cyanoacrylate pyrazole 1,2,3-triazole synthesis biological activity |
| title | Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety |
| title_full | Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety |
| title_fullStr | Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety |
| title_full_unstemmed | Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety |
| title_short | Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety |
| title_sort | design synthesis and biological activities of novel 2 cyanoacrylate compounds containing substituted pyrazolyl or 1 2 3 triazolyl moiety |
| topic | 2-cyanoacrylate pyrazole 1,2,3-triazole synthesis biological activity |
| url | https://www.mdpi.com/1420-3049/28/7/3141 |
| work_keys_str_mv | AT yangwang designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT yudiechen designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT yeqian designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT jiachen designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT xianchaodu designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT yujunshi designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT baolinxu designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT shenghua designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety AT hongdai designsynthesisandbiologicalactivitiesofnovel2cyanoacrylatecompoundscontainingsubstitutedpyrazolylor123triazolylmoiety |