Increasing numbers of novel pesticides
have been applied in agriculture.
However, traditional evaluation of pesticides does not distinguish
between their enantiomers, which may lead to inaccurate results. In
this study, systematic research on the chiral insecticide fluxametamide
was conducted at the enantiomeric level. The methods for enantioseparation
and semipreparative separation of fluxametamide enantiomers were developed.
The optical rotation and absolute configuration of two enantiomers
were determined, and their stability was verified in solvents and
soils. Enantioselective bioactivities against four target pests (Plutella xylostella, Spodoptera exigua, Aphis gossypii, and Tetranychus cinnabarinus) were tested. Acute toxicities of fluxametamide enantiomers toward
honeybees were also evaluated. S-(+)-Isomer exhibited
52.1–304.4 times and 2.5–3.7 times higher bioactivity
than R-(−)-isomer and rac-fluxametamide, respectively. Meanwhile, rac-fluxametamide
was more toxic than S/R-isomer,
and S-(+)-isomer showed >30-fold higher acute
toxicity
than R-(−)-isomer. Molecular docking studies
were performed with γ-aminobutyric acid receptor (GABAR) to
monitor the mechanism of stereoselective bioactivity. The better Grid
score of S-(+)-fluxametamide (−60.12 kcal/mol)
than R-(−)-enantiomer (−56.59 kcal/mol)
indicated higher bioactivity of S-(+)-isomer than
of R-(−)-isomer. The dissipation of fluxametamide
in cabbage, Chinese cabbage, and soil was nonenantioselective under
field conditions. Development of S-(+)-fluxametamide
could maintain the high-efficacy and low-risk properties, which should
attract attention of producers, applicators, and managers of pesticides.
Cycloxaprid is a novel cis-configuration neonicotinoid insecticide that is effective against a wide range of insect pests, including those that are resistant to conventional neonicotinoids. In this study, life table parameters were applied to estimate the cycloxaprid-induced sublethal effects on Aphis gossypii. The results indicated that the LC20 (0.81 mg a.i. L−1) of cycloxaprid significantly decreased the pre-oviposition period in first-progeny adults. Additionally, the life expectancy of F1 generation adults was reduced. However, no significant differences were observed for the intrinsic rate of increase (ri), finite rate of increase (λ), net reproductive rate (R0), or mean generation time (T) of F1 individuals. Therefore, resurgence in the A. gossypii population induced by a low concentration of cycloxaprid might not occur. Additionally, the response of the detoxification enzymes showed that cycloxaprid at the LC20 inhibited cytochrome P450 monooxygenase (P450) and glutathione S-transferase (GST) activities at 6 h after exposure. Such inhibition of P450 and GST activities could lead to a decrease in the metabolism of cycloxaprid, which would increase the efficacy of cycloxaprid. Therefore, our results contribute to the assessment of the overall effects of cycloxaprid on A. gossypii.
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