Trifluoroethyl
(CH2CF3) is an important functional
group in many pharmaceutical and agrochemical compounds. Herein, we
report an efficient method for the copper-catalyzed direct trifluoroethylation
of heteroarenes. The reaction exhibited good compatibility to various
substrates, and the desired products were obtained in good yields.
Preliminary mechanistic investigations indicate the trifluoroethyl
radical is involved in the catalytic circle. Moreover, the late-stage
modification of bioactive molecules further confirmed the practical
applications of this method.
Diamide insecticides, represented by chlorantraniliprole (CHL), were widely applied in the control of lepidopteran insects. In efforts to develop bioactive diamides with novel scaffolds, we design and synthesized a series of diamides containing central amino acids to conformationally simulate CHL. Bioassay results indicated that most compounds containing 1‐aminocyclopropane‐1‐carboxylic acid exhibited excellent larvacidal potency against Mythimna separate and Plutella xylostella. After a systematic structure–activity relationship study, 1–23 was identified as a potential insecticidal candidate with LC50 values of 34.920 mg·L−1 against M. separate and 61.992 mg·L−1 on P. xylostella. Finally, molecular docking revealed the possible binding mode of 1–23 with the target protein, ryanodine receptors.
Deuteriodifluoromethythio (SCF 2 D) and deuteriodifluoromethyl (CF 2 D) are important functional groups in pharmaceutical and agrochemical compounds, and the introduction of these functional groups remains a challenging. We herein report a robust reagent for deuteriodifluoromethylthiolation and deuteriodifluoromethylation. Its potentials were successfully showcased by deuteriodifluoromethylation and deuteriodifluoromethylthiolation of indoles with high-level deuterium incorporation. The reagent also has potential for deuteriodifluoromethylation and deuteriodifluoromethylthiolation of wide range of other natural or synthetic bioactive molecules.
Phenylpyrazole insecticides are widely used for crop
protection
and public sanitation by blocking gamma-aminobutyric acid (GABA)-gated
chloride channels and glutamate-gated chloride (GluCl) channels. Herein,
36 novel phenylpyrazole derivatives containing a trifluoromethylselenyl
moiety were designed and synthesized based on the strategy of introducing
a selenium element. All derivative structures were characterized by
nuclear magnetic resonance (NMR) and high-resolution mass spectrometry
(HRMS). The insecticidal activity results indicated that some derivatives
had good insecticidal activities against Aedes albopictus (A. albopictus) and Plutella xylostella (P. xylostella). The larvicidal activity against mosquitos of compounds 5, 5a, 5k, and 5l at 0.5 mg/L
was 60–80%. At a concentration of 500 mg/L, compounds 5, 5a, 5h, 5k, 5l, 5r, 6, 6j, 6k, and 7 showed a 70–100% mortality against P. xylostella. Among them, derivatives 5 and 6 had a better insecticidal effect with mortality
rates of 87 and 93% at 50 mg/L, respectively. It was summarized that
the different binding poses of fipronil and compounds 5 and 6 in the Musca domestica (M. domestica) GABARs might lead
to the disparity in bioactivity from docking studies. Toxicity tests
on zebrafish suggested that compound 6 may be slightly
less toxic to the embryos than fipronil on hatching rate.
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