Penetration, metabolism, and synergistic activity with carbaryl of some simple derivatives of 1,3-benzodioxole in the housefly

Microsomal metabolism of the 1,3-benzodioxole ring and its possible significance in synergistic action

“…The metabolites unequivocally identified are largely those resulting from attack by conjugative enzymes on the side chain moiety of the phenyl ring. More recent studies have established the in vivo metabolism of several 1,3-benzodioxoles in houseflies (Wilkinson, 1967), and other investigations (Fishbein et al, 1967a, b) have shown that a number of commercial synergists are chemically altered and excreted largely in the bile following intravenous injection into rats. The most comprehensive investigation to date is that of Casida et al (1966).…”

“…193°-95CC.) was synthesized from TCC by a method identical to that previously reported (Wilkinson, 1967). Samples of SKF 525-A (/3-diethylaminoethyl diphenylpropyl acetate hydrochloride) and naphtho-(2,3-J)-1,3-dioxole were kindly supplied by Smith Kline and French Laboratories, Philadelphia, and Julius Hyman of the Fundamental Research Co., Berkeley, Calif., respectively.…”

The metabolism of the insecticide carbaryl (1-naphthyl N-methylcarbamate) by fat body of the blowfly larva Calliphora erythrocephala

“…Effect of a 8ynergi8t. The synergist used in the present study was 5-dimethylamino-6-nitro-1,3benzodioxole, a compound that has been shown to enhance the toxicity of carbaryl to the housefly (Wilkinson, 1967). The effect of various concentrations of this synergist on carbaryl metabolism was studied and it was found that at a concentration of 0-1mm, carbaryl metabolism was inhibited by 70% ( Fig.…”

“…of ethanol). The 4-hydroxy and 5-hydroxy derivatives of carbaryl were a gift from Union Carbide Corp., South Charleston, W. Va., U.S.A. A carbaryl synergist (5dimethylamino-6-nitro-1,3-benzodioxole) was synthesized by Wilkinson (1967). NADP, glucose 6-phosphate and glucose 6-phosphate dehydrogenase were purchased from Boehringer Corp. (London) Ltd., London W. 5.…”

Some new carbamates and carbanilates

“…Extensive investigation has been conducted on the chemistry, biology, and more recently, on the synergism of carbamates and carbanilates (1)(2)(3)5,8,9,12,15,16,18).…”