Isotope-Labeled Insecticide, Radioactive Sevin (1-Naphthyl-1-Carbon-14 N-Methylcarbamate), a Convenient Synthesis

Skraba, Walter J.; Young, Frank G.

doi:10.1021/jf60103a001

Cited by 13 publications

(4 citation statements)

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“…14C ring-labeled carbaryl was prepared in the laboratory in a reaction between l-naphthol-l-14C and methyl isocyanate (14). The insecticide was isolated and purified by the method of Krishna,Dorough,and Casida (8).…”

Section: Methodsmentioning

confidence: 99%

MARINE DECOMPOSITION Persistence of carbaryl in the marine estuarine environment. Chemical and biological stability in aquarium systems

Karinen¹,

Lamberton²,

Stewart³

et al. 1967

J. Agric. Food Chem.

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Colorimetric and radiometric analyses have been used to study the persistence of carbaryl in estuarine water and mud in laboratory aquaria held at two temperatures. In the absence of mud, the carbaryl concentration decreased approximately 50% in 38 days at 80 C. Most of this decrease was accounted for by the production of 1-naphthol.At 20°C. after 17 days, the carbaryl had almost completely disappeared, with 43 % converting to 1-naphthol. When mud was present, both carbaryl and 1-naphthol declined to less than 10% in the sea water in 10 days. Both compounds were adsorbed by the mud, where decomposition continued at a slower rate. Radioactive carbon dioxide was produced in the aquaria containing 14C carbonyl-labeled and 14C ring-labeled carbaryl, indicating decomposition by hydrolysis of the carbamate and oxidation of the naphthyl ring. The total recovery of the 14C activity was only 40%. It is postulated that much of the remainder was evolved as methane. In a preliminary field experiment in which a portion of a mud flat was treated with carbaryl at rates similar to those used in the control of pests of oyster beds, carbaryl could be detected in the mud for 42 days. 1-Naphthol persisted in significant quantities for only one day.

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Section: Methodsmentioning

confidence: 99%

MARINE DECOMPOSITION Persistence of carbaryl in the marine estuarine environment. Chemical and biological stability in aquarium systems

Karinen¹,

Lamberton²,

Stewart³

et al. 1967

J. Agric. Food Chem.

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“…In this case, the carbamate was radiolabeled at three different sites on the molecule with carbon-14. One preparation had carbon 1 of the naphthyl ring radioactive (Skraba and Young, 1959), another batch of carbaryl was labeled on the carbonyl carbon, and the final preparation was labeled on the A-methyl carbon (Krishna et al, 1962). With this arrangement, each labeled preparation of carbaryl could be subjected to identical experimental parameters and the presence or absence of each labeled carbon on a particular metabolite determined.…”

mentioning

confidence: 99%

Metabolism of insecticidal methylcarbamates in animals

Hw¹

1970

J. Agric. Food Chem.

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The life of methylcarbamate insecticides in the animal body is very short. From 70 to 80% of an administered carbamate dose is usually eliminated, primarily in the urine, by 24 hr. The compounds are metabolized by hydrolytic and oxidative mechanisms and the resulting metabolites are excreted largely as sulfate and/or glucuronide conjugates. Some carbamates are reported to be conjugated directly, forming A-glucuronides, and then excreted.Hydrolysis of the carbamic acid ester results in detoxication of the insecticide. Carbamate metabolites formed by oxidation may be more or less toxic than the original compound. The toxicological properties of the conjugate metabolites have not been critically evaluated. This paper reviews recent findings on carbamate metabolism in animals, with particular emphasis on their metabolism by dairy cows and their residues in the milk.The toxicological significance of most foreign compounds entering the animal body is dependent, in part, on the manner in which they are metabolized. Some chemicals, such as strong bases, strong acids, and highly chlorinated hydrocarbons, are highly resistant to metabolism (Williams, 1963). These compounds, if toxic, would tend to retain their toxic action until excreted from the body. Usually, a chemical entering the body does undergo some type of transformation. The new chemical may be more toxic, less toxic, or equal in toxicity to the original compound. All three of these possibilities are known to occur as the result of metabolic transformation of certain carbamate insecticides by animal systems.The carbamate insecticides are esters of carbamic acid and those discussed herein are monomethyl derivatives of such esters. The first insecticidal carbamates synthesized were dimethyl carbamates (Gysin, 1952;Wiesmann, 1951;Wiesmann et al., 1951) but these did not have adequate insecticidal activity, and emphasis on the development of carbamate insecticides was placed on the more effective methylcarbamates (Casida, 1963;Fukuto, 1961;Kolbezen et al., 1954). The structures and chemical and common names of some of these compounds are given below.Although each of the compounds is a monomethyl carbamate, these three materials demonstrate that the carbamate insecticides are highly variable in their chemical makeup. Additional evidence as to the variability of the chemistry of this

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“…Reaction of geranyl bromide with phenol in anhydrous benzene led to the C-alkylated product ortho to the phenol (10-12) (Daves et al, 1967). The carbamates were then prepared from the terpenoid phenols and from 1-naphthol by reaction with the appropriate isocyanate under basic conditions (Skraba and Young, 1959). Equimolar mchloroperoxybenzoic acid selectively oxidized the 6,7-olefin of the carbamate (5) to its epoxide (20).…”

Section: Synthesis the Geranyl Phenyl Ethers (mentioning

confidence: 99%

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

Mumby

Hammock

Sparks

et al. 1979

J. Agric. Food Chem.

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Isotope-Labeled Insecticide, Radioactive Sevin (1-Naphthyl-1-Carbon-14 N-Methylcarbamate), a Convenient Synthesis

Cited by 13 publications

References 0 publications

MARINE DECOMPOSITION Persistence of carbaryl in the marine estuarine environment. Chemical and biological stability in aquarium systems

MARINE DECOMPOSITION Persistence of carbaryl in the marine estuarine environment. Chemical and biological stability in aquarium systems

Metabolism of insecticidal methylcarbamates in animals

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

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