Pyridyl terpenoid ethers with high juvenile hormone activity

Abstract

Pyridyl terpenoid ethers have outstanding juvenile hormone activity in Tenebrio molitor compared with their phenyl analogues (6,7-epoxy-3,7-dimethyloct-2-enyl 6-ethyl-3-pyridyl ether and 7-ethoxy-3,7-dimethyloct-2-enyl 6-ethyl-3-pyridyl ether are active at 100 pg/Iarva). The compounds were also active in Galleria melloiiella and Culex pigiens.

Stability of epoxide-containing juvenoids to dilute aqueous acid

“…The cis-and trans-propyl proton epoxides (Table I, compounds 5,6) were separated by preparative LC, and subsequently found to be pure isomers by TLC, LC, and GLC. The geometrical structures of the propyl proton epoxides are assigned based on and 13C NMR of the isomers (Jackman and Sternhell, 1969;Solli et al, 1976;Rakoff and Emken, 1977), synthetic methods, chromatographic behavior, and the conversion of the cis epoxide to the three diol by acid cleavage and the threo diol to the trans olefin and the erythro diol to the cis olefin by a modification of the triethyl orthoformate method of Rakoff and Emken (1977).…”

Insect Juvenile Hormone Analogues and Their Biological Activity on Sea Lice (Lepeophtheirus salmonis)

“…The product was extracted with CH 2Cl2, and the extract was washed with saturated aqueous NaHCO3 and brine and dried (MgSO4). Evaporation of solvents and distillation gave 52.3 g (84%) of the acetal 25 as a 6:4 mixture of diastereoisomers: bp 104-106°C/0.01 mmHg; 1 H NMR δ 0.91 (d, J ) 6.2 Hz, 3H), 1.08 (t, (J ) 6.6 Hz, 1H), 1.13 (s, 3H), 1.18 (t, J ) 6.9 Hz, 6H), 1.31 (s, 3H), 1.35-1.48 (m, 5H), 1.60-1.68 (m, 2H), 3.46-3.72 (m, 4H), 4.57 (bs, 1H); 13 Biological screening. Screening for JuVenile Hormone ActiVity.…”

“…The ethers 6, 11, 12, and 14 are known compounds that were prepared according to the literature (13). The other aromatic ethers recorded in Figure 2 were prepared in the same way by reaction of the appropriate alkyl bromide with a DMF solution of the sodium salt of either a hydroxypyridine or a phenol derivative at room temperature.…”

“…Ammonia was evaporated and the residue extracted with ether and dried (MgSO4). Evaporation of the solvent gave 8.3 g (98%) of the alcohol 23: bp 82-84°C/10 mmHg; 1 H NMR δ -0.15 (bs, 1 H), 0.37 (bs,13 C NMR δ 15.65, 20.10, 22.96, 24.46, 25.01, 27.76, 27.98, 42.93, 73.38, 111.71, 145.43; IR 3400 (s), 1650 (m) cm -1 . Anal.…”

Susceptibility of stored-product insects to pyridyl ether analogs of juvenile hormone

“…One of the most active insect growth regulators (IGR) against stored-product insects is the pyridyl ether analogue of juvenile hormone, (E)-5-|[5-(3,3-dimethyloxiranyl)-3methyl-2-pentenyl]oxy|-2-ethylpyridine (Figure 1,pound III; Solli et al, 1976; Kramer and McGregor, 1978).…”