Benzo[b]thienyl Carbamate Insecticides

Kilsheimer, John R.; Kaufman, H. W.; Foster, Harold M.; Driscoll, P. Robert; Glick, Laverne A.; Napier, Roger

doi:10.1021/jf60161a608

Cited by 18 publications

(7 citation statements)

References 12 publications

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“…Those listed represent but a small fraction of the thousands of carbamate chemicals which have been tested for their insecticidal activity during the past 20 years. Interest in these compounds as insecticides is greater than ever, as evidenced by their continued synthesis and evaluation Gilbert et al, 1968;Kilsheimer et al, 1969;Mahfouz et al, 1969;Nikles, 1969).…”

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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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confidence: 99%

Metabolism of insecticidal methylcarbamates in animals

Hw¹

1970

J. Agric. Food Chem.

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“…In a search for safe and hydrolytically stable carbamates, the same group developed, later on, the hydroxyquinoline derivatives such as the 2-methylquinolyl-8 methylcarbamate (Gubler et al, 1968). Kilsheimer et al (1969) describe yet another class of heterocyclic methylcarbamates based on benzothiophene; preeminent among these is benzo [6]thien-4-yl methylcarbamate (Mobam). This communication presents data on a new group of heterocyclic carbamates with interesting anticholinesterase properties.…”

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confidence: 99%

Insecticidal and anticholinesterase activity of benzotriazolyl methyl and dimethylcarbamates

Sacher¹,

Alt²,

Darlington³

1973

J. Agric. Food Chem.

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“…Benzo(b)thien-4-yl methylcarbamate (Mobam) is an effective pesticide that exhibits broad spectrum insecticidal activity coupled with an apparent low mammalian toxicity (2,7). Ruminants administered "IC-Mobam as single oral doses excreted 87 to 96% of the 14C dose via the urine in 24 hr (10).…”

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confidence: 99%