Synthesis of C 14 -Labeled 2-Methyl-2-(methylthio)propionaldehyde O-(Methylcarbamoyl)oxime

The metabolism of 14C-Temik aldicarb pesticide [2-methyl-2-(methylthio)propionaldehyde ¿>-(methylcarbamoyl)oxime] was investigated in greenhouseand field-grown potato plants. Aldicarb was metabolized through oxidation to 2-methyl-2-(methylsulfinyl)propionaldehyde O-(methylcarbamoyl)oxime and 2-methyl-2-(methylsulfonyl)propionaldehyde 0-(methylcarbamoyl)oxime. The former was the major metabolite in the foliage during early stages of plant growth and the latter became the predominant one during maturation of the plant. Sub-sequent degradation of these two carbamate metabolites yielded 2-methyl-2-(methylsufinyl)propionaldehyde oxime and 2-methyl-2-(methylsulfonyl)propionaldehyde oxime. The relative concentrations

Section: Methodsmentioning

confidence: 99%

Metabolism of 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime (Temik aldicarb pesticide) in potato plants

Andrawes¹,

Bagley²,

Herrett³

1971

“…Compounds I, II, and III will be referred to hereafter as ¿-methyl, tertbutyl, and '-methyl labeled Temik, respectively. 2 -Methyl -2 -(methyl-C14 -thio)propionaldehyde oxime (Smethyl labeled oxime) and 2-methyl-2-(methylthio) propionaldehyde -2 -CM oxime (ieri-butyl labeled oxime) were synthesized by Bartley et al (4). The specific activities of ¿-methyl-C14 and 7frf-butyl-C14 oximes were 7.0 me.…”

Section: Methodsmentioning

confidence: 99%

“…Labeled 2 -methyl -2 -(methylsulfinyl) propionaldehyde 0 -(methyl-C14 -carbamoyl) oxime ( -methyl-C14 Temik sulfoxide) was synthesized by Bartley et al (4).…”

Section: Methodsmentioning

confidence: 99%

Metabolism of 2-Methyl-2-(methylthio)propionaldehyde O-(Methylcarbamoyl)oxime in Rat

Knaak¹,

Tallant²,

Sullivan³

1966

The metabolic fate of S-methyl-C14, ferf-butyl-C14, and N-methyl-C14 Temik [2-methyl-2-(methylthio)propionaldehyde 0-(methylcarbamoyl)oxime] was investigated in the rat. The over-all recovery of the S-methyl, ferf-butyl, and N-methyl label was, respectively, 95, 96 and 72% of the doses. Tissue residues (8 to 10% of the dose) were found only in the case of N-methyl labeled Temik. Seventy per cent of an oral dose of Temik was excreted as 2-methyl-2-(methylsulfinyl)propionaldehyde oxime and 2methyl-2-(methylsulfinyl)propionaldehyde 0-(methylcarbamoyl)oxime.The remaining metabolites appeared to be acids formed by further oxidation of the oxime. In conjunction with the metabolic studies, in vivo cholinesterase depression and recovery curves were obtained with plasma, red blood cells, and brain. At an oral dose of 0.33 mg. per kg., the cholinesterase activity of Temik-treated rats recovered from inhibition two hours prior to the rats treated with 2-methyl-2-(methylsulfinyl)propionaldehyde O-(methylcarbarnoyl)oxime.

“…per mmole) and one of C14-(S-methyl)Temik (1.2 me. per mmole) were prepared in this laboratory from a procedure supplied by Union Carbide Corp. (Bartley et al, 1966;Knaak et al, 1966;Payne et al, 1966). C14-(carbonyl)Temik (2.08 me.…”

Section: Xh Ch3mentioning

confidence: 99%

Fate of 2-methyl-2-(methylthio)propionaldehyde O-(methylcarbamoyl)oxime (Temik) in cotton plants and soil

Coppedge¹,

Lindquist²,

Bull³

et al. 1967

In the cotton plant, Temik [10% granular formulation of UC-21149, 2-methyl-2-(methylthio)propionaldehyde 0-(methylcarbamoyl)oxime] was rapidly metabolized to its sulfinyl derivative (Temiksulfoxide); further oxidation to the sulfonyl compound (Temik-sulfone) was slow. No evidence of oxidative A-demethylation was found. The sulfinyl derivative was degraded primarily by hydrolysis to a sulfinyl-oxime. Both Temik-sulfoxide and Temik-sulfone were stable in cotton. Relatively large amounts of radioactivity were lost from C14-Temik-treated excised cotton leaves. In the three soil types studied under laboratory conditions,