N-Sulfinylated derivatives of methylcarbamate esters

Fahmy, M. A. H.; Fukuto, T. R.

doi:10.1021/jf00105a034

Cited by 24 publications

(9 citation statements)

References 6 publications

(12 reference statements)

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“…For example, on a weight basis DCDM-S-carbofuran was 76-fold less toxic than carbofuran. In general, the data were similar to those reported previously for the -ZV^ZV-thiodicarbamate (Fahmy et al, 1978) and N-sulfinylated carbamate derivatives (Fahmy and Fukuto, 1981).…”

Section: Resultssupporting

confidence: 90%

Formamidine-S-carbamates: a new procarbamate analog with improved ovicidal and acaricidal activities

Eya¹,

Fukuto²

1986

J. Agric. Food Chem.

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Section: Resultssupporting

confidence: 90%

Formamidine-S-carbamates: a new procarbamate analog with improved ovicidal and acaricidal activities

Eya¹,

Fukuto²

1986

J. Agric. Food Chem.

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“…The increased mammalian safety of the sulfenylated derivatives of toxic methylcarbamate esters (like carbosulfan) has been attributed to the delay factor provide by the N-sulfenyl moiety; i.e., derivatization allows the compound to be metabolized to nontoxic products before intoxication can take place (Fahmy and Fukuto, 1981). Maged et al, (2006) were reported that the two carbosulfan used forms caused several subacute histological damages in liver and kidney tissues, where the damages were more occurred by the technical than the formulation.…”

Section: Resultsmentioning

confidence: 99%

Some Subacute Histopathological Effects of Carbosulfan Technical and Marsal 20% Ec Formulation in Male Albino Rats

Alla

2011

Egyptian Journal of Agricultural Research

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Six equal groups of adult male albino rats were orally administered with three different concentrations (14, 7, 3.5 mg/kg bw.) of carbosulfan technical (88.5%) and Marsal 20% EC Formulation (one conc. of each form per group) for 28 consecutive days, then kept two other weeks without treatment as a recovery period.Samples of brain, thyroid, lung and spleen tissues were taken from all groups at the end of treatment and recovery periods, examined microscopally and compared with control tissues.Results showed that the treatment with technical carbosulfan not affected on thyroid tissues, when affected on brain, lung and spleen tissues, then lung and spleen tissues were repaired after the recovery period but brain tissues still damaged.In case of Marsal 20%EC formulation treatment both thyroid and brain tissues not affected, when both lung and spleen tissues affected and this effect was repaired after the recovery period and the tissues returned to normal state.

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“…However, unlike the phosphotriester chemistry, which is not synthesized naturally, the insecticidal carbamates are derived from carbamic acid, a chemistry used in a wide range of common cellular metabolites (carbamoyl phosphate and urea, for example). Again, like the OPs, carbamates are usually applied as chemically modified protoxins that are more readily activated in insects than mammals, such as the N ‐sulfonyl carbamates (Kinoshita and Fukuto 1980; Fahmy and Fukuto 1981).…”

Section: Insecticidal Carbamate Metabolizing Enzymesmentioning

confidence: 99%

The evolution of new enzyme function: lessons from xenobiotic metabolizing bacteria versus insecticide‐resistant insects

Russell

Scott

Jackson

et al. 2011

Evolutionary Applications

124

100

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Here, we compare the evolutionary routes by which bacteria and insects have evolved enzymatic processes for the degradation of four classes of synthetic chemical insecticide. For insects, the selective advantage of such degradative activities is survival on exposure to the insecticide, whereas for the bacteria the advantage is simply a matter of access to additional sources of nutrients. Nevertheless, bacteria have evolved highly efficient enzymes from a wide variety of enzyme families, whereas insects have relied upon generalist esterase-, cytochrome P450- and glutathione-S-transferase-dependent detoxification systems. Moreover, the mutant insect enzymes are less efficient kinetically and less diverged in sequence from their putative ancestors than their bacterial counterparts. This presumably reflects several advantages that bacteria have over insects in the acquisition of new enzymatic functions, such as a broad biochemical repertoire from which new functions can be evolved, large population sizes, high effective mutation rates, very short generation times and access to genetic diversity through horizontal gene transfer. Both the insect and bacterial systems support recent theory proposing that new biochemical functions often evolve from ‘promiscuous’ activities in existing enzymes, with subsequent mutations then enhancing those activities. Study of the insect enzymes will help in resistance management, while the bacterial enzymes are potential bioremediants of insecticide residues in a range of contaminated environments.

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N-Sulfinylated derivatives of methylcarbamate esters

Cited by 24 publications

References 6 publications

Formamidine-S-carbamates: a new procarbamate analog with improved ovicidal and acaricidal activities

Formamidine-S-carbamates: a new procarbamate analog with improved ovicidal and acaricidal activities

Some Subacute Histopathological Effects of Carbosulfan Technical and Marsal 20% Ec Formulation in Male Albino Rats

The evolution of new enzyme function: lessons from xenobiotic metabolizing bacteria versus insecticide‐resistant insects

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