Recently, the structural optimization of natural bioactive products has been one of the important ways to discover new pesticide candidates. Based on osthole as a lead compound, herein, a series of new 2-isopropanol-4-methoxy-7-alkyl/aryloxycarbonyl-()-vinyl-2,3-dihydrobenzofuran derivatives were synthesized. Steric configurations of compounds , , , , , , and were confirmed by X-ray monocrystallography. Notably, an efficient method for preparation of 2-isopropanol-2,3-dihydrobenzofurans from osthole by the epoxidation and rearrangement reactions was developed. Against Linnaeus, compound ( = CHCHPh; LC: 0.759 mg/mL) displayed a 1.9-fold insecticidal activity compared to that of osthole; against Boisduval, compound ( = (CH)CH; LC: 0.401 mg/mL) exhibited a 3.3-fold acaricidal activity and good control effects compared to those of osthole. By the scanning electron microscope (SEM) imaging method, it was demonstrated that the acaricidal activity of compound may be related to the damage of the cuticle layer crest of . Compound could be further studied as a potential acaricide.
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