PEST MANAGEMENT SCIENCE
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2016
·Vol. 73
·期 5
·917-924
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IF 2.811
Qi Liu,Rui Zhu,Shang Gao,Shi-Han Ma,Hai-Jun Tang,Jian-Jun Yang,Ya-Mei Diao,Hong-Lei Wang,Hong-Jun Zhu
BACKGROUND Anthranilic diamide derivatives are among the most important classes of synthetic insecticides. Moreover, the 1,2,4-oxadiazole heterocycle, a bioisostere of amide, has been extensively used in pesticides. In order to discover novel molecules with high insecticidal activities, a series of anthranilic diamide analogues containing 1,2,4-oxadiazole rings were designed and synthesised. RESULTS A series of novel anthranilic diamide derivatives containing 1,2,4-oxadiazole were obtained, and confirmed by 1 H and 13 C nuclear magnetic resonance and high-resolution mass spectrometry. The structure of 3-bromo- N -(4-chloro-2-methyl-6-{3-[(methylsulphonyl)methyl]-1,2,4-oxadiazol-5-yl}phenyl)-1-(3-chloropyridin-2-yl)-1 H -pyrazole-5-carboxamide was further characterised by X-ray diffraction analysis. In addition, bioassays showed that most of the newly synthesised compounds displayed 100% mortality against Plutella xylostella at 100 mg L −1 , and compound 3IIl showed 90% larvicidal activities at a concentration of 0.5 mg L −1 . The LC 50 value of 3IIl was 0.20 mg L −1 , which indicated that it may be used as a potential leading compound for further structural optimisation. Furthermore, brief comparative molecular field analysis (CoMFA) models were established to study the structure–activity relationships (SARs) of the title compounds. CONCLUSION Compound 3IIl may be used as a potential leading compound for further structural optimisation, and SARs and CoMFA models could provide reliable clues for further structural optimisation. © 2016 Society of Chemical Industry
研究领域:
农药化学
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有机合成
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生物活性研究
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DOI
高影响因子
RSC Advances
·
2014
·Vol. 4
·期 98
·55445-55451
·
IF 3.708
Qi Liu,Kai Chen,Qiang Wang,Jueping Ni,Yufeng Li,Hongjun Zhu,Yuan Ding
A series of anthranilic diamides analogs (5a–x) containing 1,3,4-oxadiazole rings were synthesized and characterized by 1H NMR, 13C NMR and mass spectrometry. The structure of N-(4-chloro-2-methyl-6-(5-(thiophen-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)methacrylamide (5u) was determined by X-ray diffraction crystallography. The insecticidal activities of these new compounds against diamondback moth (Plutella xylostella) were evaluated. Preliminary bioassays indicated that some of these compounds exhibited good insecticidal activities against P. xylostella, especially 3-bromo-N-(4-bromo-2-methyl-6-(5-(pyrazin-2-yl)-1,3,4-oxadiazol-2-yl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (5d), which displayed 100%, 80.95% and 57.14% activity against P. xylostella at 40 μg mL−1, 10 μg mL−1 and 4 μg mL−1, respectively. The relationship between structure and insecticidal activity was discussed. The density functional theory (DFT) studies could be helpful to understand the various insecticidal activities.
研究领域:
农药化学
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有机化学
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昆虫学
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DOI
高影响因子
JOURNAL OF HETEROCYCLIC CHEMISTRY
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2021
·Vol. 58
·期 11
·2189-2202
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IF 2.193
Abdalla Khallaf,Ping Wang,Shuping Zhuo,Hongjun Zhu,Hui Liu
The preparation of novel anthranilic diamide derivatives is extremely important for agricultural pest control. In this study, pyridylpyrazole-4-carboxamides containing a 1,3,4-oxadiazole ring were designed and synthesized via the dehydration of aromatic hydrazine derivatives and formanilides in the presence of an alkali. The insecticidal activities of these new compounds against the diamondback moth ( Plutella xylostella ) were evaluated. N-(4-chloro-2-methyl-6-(5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl)phenyl)-5-methyl-1-(pyridin-2-yl)-1H-pyrazole-4-carboxamide ( 8h6 ) showed 67%, 50%, 34%, 20%, and 17% activity at concentrations of 100, 50, 10, 5, and 1 μg ml −1 , respectively. Density functional theory calculations showed that the introduction of the 1,3,4-oxadiazole ring significantly changed the electron distributions in both the highest occupied and lowest unoccupied molecular orbitals, resulting in these compounds having much larger energy gaps than the well-known insecticide chlorantraniliprole, which may account for their lower activity. The results of this study demonstrate that anthranilic diamides substituted with a 1,3,4-oxadiazole ring are effective insecticides that can be used for pest management.
研究领域:
农业科学
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有机化学
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DOI
高影响因子
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