Über die Synthese von Phosphamidon und seinen Abbau in Pflanzen

Anliker, R.; Beriger, E.; Geiger, M.; Schmid, Karl

doi:10.1002/hlca.19610440621

Cited by 22 publications

(4 citation statements)

References 32 publications

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“…Jaques and Bein (1960) reported that plants metabolized phosphamidon to its des-W-ethyl derivative. Anliker et al (1961) and Bull et al (1967) confirmed that W-deethylation of phosphamidon occurs in several plant systems. Phosphamidon and its des-W-ethyl metabolite were rapidly hydrolyzed by plants to innocuous polar compounds such as a-chloro-W,W-diethylacetoacetamide, a-chloro-W-ethylacetoacetamide, and dimethyl phosphate.…”

Section: Phosphamidonsupporting

confidence: 55%

“…To prepare phosphamidon-3 2i°, a,a-dichloro-7V,7V-diethylacetoacetamide was reacted with trimethyl phosphite-3 . The chlorinated acetoacetamide was prepared according to the procedure of Anliker et al (1961). Sulfuryl chloride (516 mg, 3.84 mM), dissolved in 5 ml of methylene chloride, was added dropwise to 10 ml of a chilled methylene chloride solution containing /V,A-diethylacetoacetamide (300 mg, 1.92 mM), prepared by Clemons and Menzer (1968).…”

Section: Methodsmentioning

confidence: 99%

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Nature of neutral phosphorus ester metabolites of phosphamidon formed in rats and liver microsomes

Lucier¹,

Menzer²

1971

J. Agric. Food Chem.

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Section: Phosphamidonsupporting

confidence: 55%

Section: Methodsmentioning

confidence: 99%

Nature of neutral phosphorus ester metabolites of phosphamidon formed in rats and liver microsomes

Lucier¹,

Menzer²

1971

J. Agric. Food Chem.

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“…and, 4 days later, at 2.0 mg. per kg. Another goat, weighing 57.0 kg., was treated with a mixture of SD 9129-P32 and 7methyl-C14 and, 3 weeks later, with a mixture of Bidrin-P32 and A7-methyl-C14 at 1.0 mg. per kg. The labeled compound was distributed equally among four gelatin capsules containing crushed corn to absorb the small amount of chloroform involved in the transfer.…”

Section: Treatment Of Plants and Animalsmentioning

confidence: 99%

“…The unsubstituted amide of phosphamidon [3-(dimethoxyphosphinyloxy) -2 -chlorocrotonamide] and the des-O-methyl derivative [3-(hydroxymethoxyphosphinyloxy) -A7,A7 -diethyl -2-chloro-1 Present address, Department of Entomology, University of Maryland, College Park, Md. 2 Present address, Division of Entomology and Acarology, University of California, Berkeley, Calif. crotonamide] were not detected in plants (3,76).…”

mentioning

confidence: 99%

Insecticide Metabolism, Nature of Toxic Metabolites Formed in Mammals, Insects, and Plants from 3-(Dimethoxyphosphinyloxy)-N-N-dimethyl-cis-croton-amide and Its N-Methyl Analog

Menzer¹,

Casida²

1965

J. Agric. Food Chem.

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Bidrin, 3-(dimethoxyphosphinyloxy)-N,N-dimethyl-c/s-crotonamide, is metabolized to yield trace amounts of 3-(dimethoxyphosphinyloxy)-N-methyl-N-hydroxymethyl-c/s-crotonamide and larger amounts of 3-(dimethoxyphosphinyloxy)-N-methyl-c/s-crotonamide (SD 9129). SD 9129 is further metabolized to yield 3-(dimethoxyphosphinyloxy)-N-hydroxymethyl-c/s-crotonamide and 3-(dimethoxyphosphinyloxy)-c/s-crotonamide. The toxicity to both insects and mammals increased upon successive N-demethylation. Balance studies on the fate of the P32 and C14 from Bidrin-P32, Bidrin-N-methyl-C14, SD 9129-P32, and SD 9129-N-methyl-C14 are considered. Studies on milk residues, urinalysis, and metabolism in houseflies (Musca domestica L.) and bean plants are reported. An unusual pattern of synergism of the toxicity of the Bidrin metabolites in houseflies by sesamex [2-(2-ethoxyethoxy)ethyl-3,4-(methylenedioxy)phenyl acetal of acetaldehyde] was noted.NO. 2 MAR.-APR.

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Ketenes, Ketene Dimers, and Related Substances

Abaecherli

Miller

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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This article describes monomeric ketenes, ketene dimers, and acetoacetic acid derivatives. The parent substance, ketene itself, is the only ketene to be manufactured in large industrial quantities. The manufacturing process, chemical and physical properties, and industrial uses of ketene are described in detail. A table is included that lists examples of higher ketenes, thioketenes. The manufacture of acetic anhydride is described. The article gives a thorough review of all aspects of diketene which is an important product derived from ketene on an industrial scale. Diketene gives access to open‐chain acetoacetic acid derivatives as well as heterocyclic systems. An overview is provided on dimeric aldoketenes and ketoketenes. Acetoacetic acid derivatives are of significant economic importance. The manufacturing processes of diketene esters and of acetoacetarylides are outlined. This includes methyl acetoacetate and acetoacetanilide. Industrial uses of the various ketene and diketene derivatives are discussed with emphasis on the most important life science applications. Vol. 14, pp. 953–978, 157 refs. to December 1993.

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Über die Synthese von Phosphamidon und seinen Abbau in Pflanzen

Cited by 22 publications

References 32 publications

Nature of neutral phosphorus ester metabolites of phosphamidon formed in rats and liver microsomes

Nature of neutral phosphorus ester metabolites of phosphamidon formed in rats and liver microsomes

Insecticide Metabolism, Nature of Toxic Metabolites Formed in Mammals, Insects, and Plants from 3-(Dimethoxyphosphinyloxy)-N-N-dimethyl-cis-croton-amide and Its N-Methyl Analog

Ketenes, Ketene Dimers, and Related Substances

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