| Citation: |
YANG Shuai, JIANG Xunyuan, ZHANG Yue, et al. Synthesis, insecticidal activity and toxicity to bees of phenylpyrazoles[J]. Journal of South China Agricultural University, 2020, 41(3): 72-79. DOI: 10.7671/j.issn.1001-411X.201906018
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To obtain phenylpyrazoles which have insecticidal activities and are eco-friendly based on fipronil framework.
Using anilines with different substituents as materials, phenylpyrazole compounds 1−21 with different substituents were synthesized in two steps. The product structures were confirmed by 1H NMR, 13C NMR and ESI-MS analysis. The biological activities of target products against Plutella xylostella were determined by leaf immersion method. Acute oral toxicities of compounds 1, 5, 12, and 16 to Apis cerana were determined.
After 24 h treatment, LC50 of compounds 1, 5, 12, 16 against P. xylostella were 0.26, 0.95, 0.33 and 1.10 mg·L−1 respectively. The activities of compounds 1 and 12 against P. xylostella were higher than that of fipronil. Compounds 5, 12 and 16 showed lower acute oral toxicities to A. cerana compared with fipronil(0.05 mg·L−1), but still were highly toxic with LC50 of 0.21, 0.22 and 0.09 mg·L−1 respectively. The structure-activity relationship indicated that the substituent of the phenyl-ring had a great influence on the activity of the phenylpyrazole compound. When the ortho position of the benzene ring was —Cl or —Br, the para position was —Cl, —CF3 or —OCF3, the compound had excellent activity against P. xylostella.
Replacement of substituents on the phenyl-ring of fipronil can improve the biological activity against P. xylostella, and reduce the toxicity to A. cerana, which has certain guiding significance for the development and structural optimization of arylpyrazole insecticides in the future.
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