Methylene dioxyphenyls

A number of synergists are used with pyrethrum to increase its toxicity. Most of the better ones, as far as flying insects are concerned, are of the methylene dioxyphenyl type. The best known of this type is piperonyl butoxide. 

Philleo et al. (29) recently confirmed the inhibitory action of methylene dioxyphenyl groups on biological oxidations in insects, including epoxidation and hydroxylation of certain compounds. 

In additional in vitro studies with a number of methylene-dioxyphenyl compounds, only tropital, in addition to piperonyl butoxide, had similar inhibitory effects on the metabolism of DEHP by trout liver homogenates and serum (16). Of the methyl-enedioxyphenyl compounds studied, only tropital had a long side chain like that of piperonyl butoxide. This suggests that similarities in the side chains of these two compounds and the side chains of DEHP and 2,4-dichlorophenoxyacetic acid-n-butyl ester may be responsible for this inhibition. 

Operational activities have continued under Project Prism, the international initiative designed to address diversion of the five main precursors used in the illicit manufacture of amphetamine-type stimulants, namely, ephedrine, 3,4-methylene-dioxyphenyl-2-propanone (3,4-MDP-2-P), l-phenyl-2-propanone (P-2-P), pseudo-ephedrine and safrole, as well as the equipment used in such illicit manufacture. Activities during 2004 have focused on launching operations to address weaknesses in control and monitoring mechanisms identified during 2003, such as monitoring... 

The final group of natural benzofurans includes the 2-phenylbenzo-furans and 2-phenyl-2,3-dihydrobenzofurans. 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl)benzofuran (64)147 has recently been isolated from yeast. Other members of the same group recently isolated from various plants are eupomatene (7-methoxy-3-methyl-2-(3,4-methylene-dioxyphenyl)-5-fi-Gms-propenylbenzofuran (65) 180 egonol (66),147,181-184... 

B. Newman, V. T. Sullivan, and A. Dihrberg, Thin-layer chromatography of lysergic acid diethylamide (LSD), iV,N-dimethyl trypt-amine (DMT), methylene dioxyphenyl isopropylamine (STP), and ibogaine, J. Crim. Law Criminol., 61 112 (1970). 

A number of classes of monooxygenase inhibitors, in addition to methylene-dioxyphenyl compounds, are now known to form metabolic-intermediate complexes including amphetamine and its derivatives and SKF-525A and its derivatives. 

Although the trimethoxyphenyl part shows some similarity to the methylene-dioxyphenyl group in tadalafil and both are connected to a hydrophobic aromatic core residue, the H-bond donor function is lacking. On the other hand, for the analogs of 51, the presence of the carbonyl groups was also found to be important, another parallel to the SAR in the tadalafil series. 

The Kohonen neural network has been used to develop bioisosteres of the methylen-dioxyphenyl group found in a variety of antag-... 

Indonesia" Acetic anhydride, A -acetyl anthranilic acid, ephedrine, ergometrine, ergotamine, isosafrole, 3,4-methylene-dioxyphenyl-2-propanone, 1 -phenyI-2-propanone, piperonal, pseudoephedrine, safrole anthranilic acid, phenylacetic acid 18 February 2000... 

Franklin, M.R. (1971). The enzymic formation of a methylene dioxyphenyl derivative exhibiting an isocyanide-like spectrum with reduced cytochrome P-450 in hepatic microsomes. Xenobiotica 1, 581-591. 

Accidental spraying of beehives in Connecticut with diazinon resulted in a complete kill of resident honeybees. Dead bees contained up to 3.0mg/kg of diazinon. Diazinon is an effective insecticide. LD50 values for diazinon and adult houseflies (Musca domestica), applied topically, were 0.4 (xg/insect, or4.6 mg/kg BW. LD50 values for larvae of the large white butterfly, applied topically, were 8.8 mg/kg BW for diazinon, and 11.0 mg/kg BW for diazoxon. Pretreatment of larvae with methylene dioxyphenyl compounds antagonized the action of diazinon by a factor of about 2, but synergized the action of diazoxon by an order of magnitude. 

See 2 5-Dihydroxy-p-xylene. a-Hydropiperic Acid (4-[3 A-Methylene-dioxyphenyl]-2-bi4tylene-l-carboxylic add, 3 4-methylenedioxyphenylethylidenepropionic add, 3 4-methylen ioxyphenylpropenylacetic add)... 

Weinstein. Ann., 1885, 227, 32. p-Hydropiperic i id (2-[3 4-MeAylene-dioxyphenylethyl]-acrylic add, 4-[3 4-methylene-dioxyphenyl]- -bmtylem- -iMrboxylic add)... 

---