Insecticide Screening, Insecticidal Activity of Alkylthiophenyl N-Methylcarbamates

Metcalf, Robert L.; Fukuto, T. R.; Frederickson, Mary; Peak, L.

doi:10.1021/jf60141a025

Cited by 14 publications

(10 citation statements)

References 2 publications

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“…The meta position in turn is superior to the para (26 vs. 24, 29 vs. 35, 31 vs. 36). A similar positional relationship is observed with alkoxy or alkylthio substituents of similar bulk (Metcalf et al, 1965) and with the cyclohexyl group (Metcalf et al, 1962).…”

Section: Biological Aspectssupporting

confidence: 67%

Insecticidal 2-(Methylcarbamoyloxyphenyl)-1,3-dioxolanes,-oxathiolanes, and-dithiolanes

Durden¹,

Weiden²

1969

J. Agric. Food Chem.

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2-(2-Methylcarbamoyloxyphenyl)-l,3-dithiolane (1), -dioxolane (3), and -oxathiolane (2) were effective inhibitors of fly-head acetylcholinesterase and had activity against certain aphids, coleopterous pests, and the housefly. Analogs and homologs of these materials were of diminished activity; in particular, insecticidal activity is more drastically affected by structural changes than is acetylcholinesterase inhibition. 5-oxidation of 1 also decreased activity. The parent phenol of 1 was relatively effective as an acetylcholinesterase inhibitor, I-,o = 5 X 10~5. Carbamate 1 showed systemic activity against cer-

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Section: Biological Aspectssupporting

confidence: 67%

Insecticidal 2-(Methylcarbamoyloxyphenyl)-1,3-dioxolanes,-oxathiolanes, and-dithiolanes

Durden¹,

Weiden²

1969

J. Agric. Food Chem.

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“…With Mexican bean beetles, methyl groups in the azophenyl ring, (compounds V, VI, and VII) display an effect similar to that shown by the single-ring aromatic carbamates studied earlier (Metcalf and Fukuto, 1965), ortho, meta > para.…”

Section: Synthesissupporting

confidence: 63%

“…In addition to a physical fit of the carbamate molecule in the enzyme surface, an electrostatic attraction was proposed to keep it in position and thereby deny access to acetylcholine (Metcalf and Fukuto, 1965). In the enzyme, a positively charged esteratic and negatively charged anionic site, separated by a distance of about 5 A., were matched and held in place by oppositely polarized portions of the carbamate substrate.…”

Section: Synthesismentioning

confidence: 99%

Azobenzene carbamates as insecticides

Kaeding¹,

Kenaga²

1967

J. Agric. Food Chem.

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“…whereas in flies the LD50 is 90ug./g. (Metcalf & Fukuto, 1965). Oxidation of the carbamates is generally believed to result in their detoxication (Metcalf & Fukuto, 1965) and it is significant that the enzyme preparations from several strains of fly studied in the present work were about three times more active in oxidizing isopropylbenzene than those from locusts (Tables 3 and 4).…”

Section: Rabbitmentioning

confidence: 99%

Enzymic oxidation of some alkylbenzenes in insects and vertebrates

Chakroborty¹,

Smith²

1967

Biochemical Journal

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1. Oxidation rates of alkylbenzenes have been measured in 10000g supernatants of vertebrate livers, locust fat bodies and housefly abdomens. 2. Activity per g. of insect was greater in fly than locust preparations but both were of the same order as a range of vertebrate species. 3. Methyl groups of toluene and p-nitrotoluene were oxidized more rapidly than the side chains of higher homologues. 4. In the higher homologues hydroxylation occurred most readily at the alpha-methylene group and less readily at penultimate methylene and terminal methyl groups. 5. Oxidations in both vertebrates and insects were inhibited by piperonylbutoxide and similar synergists. 6. Oxidation activity was stimulated by pretreatment of rats, but not locusts, with phenobarbitone or 3,4-benzopyrene.

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Insecticide Screening, Insecticidal Activity of Alkylthiophenyl N-Methylcarbamates

Cited by 14 publications

References 2 publications

Insecticidal 2-(Methylcarbamoyloxyphenyl)-1,3-dioxolanes,-oxathiolanes, and-dithiolanes

Insecticidal 2-(Methylcarbamoyloxyphenyl)-1,3-dioxolanes,-oxathiolanes, and-dithiolanes

Azobenzene carbamates as insecticides

Enzymic oxidation of some alkylbenzenes in insects and vertebrates

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