Stability of epoxide-containing juvenoids to dilute aqueous acid

Abstract

Table III, C). This increased persistence of [14C]paraoxon due to anethole could, therefore, be related to the increased toxicity of paraoxon.In summary, four major results should be mentioned. (1) Topically applied anethole and anisaldehyde increased the toxicity of several classes of topically applied synthetic insecticides to houseflies (Table I). ( 2) The presence of anethole in the housefly diet increased the toxicity of topically applied parathion or paraoxon to houseflies. (3) The presence of anethole in the diet resulted in an increased penetration of [14C]paraoxon derived radiocarbon into the housefly body (Table II). ( 4) The presence of anethole in the housefly diet reduced the degradation of [14C]paraoxon by a cell-free supernatant prepared from houseflies fed anethole for 3 days (Table III). It appears, therefore, that the increased mortalities of houseflies fed anethole in their diet for 3 days prior to topical application of paraoxon was due to an increased penetration of paraoxon into the insect body and an increased stability of paraoxon due to a reduction in the degradation of paraoxon to nontoxic, water-soluble metabolites. Both of these effects would increase the amount of toxic paraoxon within the houseflies and hence increase mortalities.

Novel assay for determining the metabolic fate of juvenile hormone III: A study with Drosophila melanogaster

“…Thus, it appears that incubation in acid of nanogram quantities of JH yields very low levels of the JH diol, while enzymatic generation results in quantitative yields. This low yield of diol and production of materials that are less polar than the diol agrees with the results reported by Schooley [28] and Mumby and Hammock [29] who caution that the use of strong acid for the production of diols from submicrogram quantities of JH and other epoxides could result in the cyclization and rearrangement of the parent molecule. The use of dilute acetic acid [29], periodic acid 1301, or carrier molecules (such as epoxycitronellyl acetate) can reduce some of the side reactions between JH and strong acid.…”

“…This low yield of diol and production of materials that are less polar than the diol agrees with the results reported by Schooley [28] and Mumby and Hammock [29] who caution that the use of strong acid for the production of diols from submicrogram quantities of JH and other epoxides could result in the cyclization and rearrangement of the parent molecule. The use of dilute acetic acid [29], periodic acid 1301, or carrier molecules (such as epoxycitronellyl acetate) can reduce some of the side reactions between JH and strong acid. However, even when the reaction is done on the milligram scale, the presence of trace amounts of metal ions can result in major contamination from side reactions The Rfs of the enzymatically generated standards and the nonradioactive standards in four different solvent systems are shown in Table 1.…”

Effects of parasitization of Trichoplusia ni by Chelonus sp.

“…(1-(4'-ethlyphenoxy)-6,7-epoxy-3ethyl-7-methyl nonane, MW=303) was a gift from Dr Peter Masner, Dr Maag AG, Switzerland, while R 20458 [(2E)-1-(4'-ethyl phenoxy)-6,7-epoxy-3,7-dimethyl-2-octene was synthesized in this laboratory (Mumby & Hammock, 1979).…”

Synthesis and bioassay of carbamate inhibitors of the juvenile hormone hydrolyzing esterases from the housefly, Musca domestica

“…Caled for C20H31NO4: C, 68.74; H, 8.94. Found, C, 68.66; , 8.70. prepared by a Williamson ether synthesis, reacting the corresponding monoacetate of catechol, resorcinol, or hydroquinone with geranyl bromide (Table I, 1-9) or 0021-8561/79/1427- 7-methoxygeranyl bromide (13-19) (Hammock et al, 1974;Henrick et al, 1978;Mumby and Hammock, 1978).…”