Optimization of
Osthole as a Pesticide Candidate:
Synthesis, Crystal Structures, and Agrochemical Properties of Acrylate
Derivatives of Isopropenyl 2,3-Dihydrobenzofurans
posted on 2023-11-15, 16:06authored byZili Ren, Min Lv, Huqi Liu, Houpeng Wen, Yuling Zhang, Hui Xu
For high-value-added application of osthole derivatives
as a pesticide
candidate in crop protection, by the use of osthole as a lead compound,
a series of novel acrylate derivatives of isopropenyl 2,3-dihydrobenzofurans
were prepared by the successive bromination, rearrangement, and esterization
reactions. Three-dimensional structures of four compounds were determined
by single-crystal X-ray diffraction. The possible mechanism for construction
of this new isopropenyl 2,3-dihydrobenzofuran skeleton from the osthole
was presented. Against Plutella xylostella Linnaeus, compound 32 (R = PhCH2CH2) displayed 3.5-fold potent insecticidal activity of osthole. Against Tetranychus cinnabarinus Boisduval, compound 40 (LC50: 0.165 mg/mL; R = (CH2)13CH3) showed 8.3-fold pronounced acaricidal activity
of osthole (LC50: 1.367 mg/mL); notably, its control effect
can be comparable to that of the commercial acaricide spirodiclofen.
Additionally, the scanning electron microscopy imaging method demonstrated
that compound 40 can destroy the stratum corneum of T. cinnabarinus. Compound 40 can be
further explored as a lead acaricidal agent.