Metabolism of 2,2-dimethyl-2,3-dihydrobenzofuran-7-N-methylcarbamate (Furadan) in plants, insects, and mamals

Metcalf, Robert L.; Fukuto, T. R.; Collins, C.; Borck, Kathleen; El-Aziz, S. Abd; Muñoz, Ricardo; Cassil, C. C.

doi:10.1021/jf60156a033

Cited by 136 publications

(73 citation statements)

References 8 publications

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“…In that paper, Dorough et al incubated carbaryl with rat liver homogenate and found two ring hydroxylation products, which are 4-hydroxy-and 5-hydroxycarbaryl. Later, the same metabolism processes were also found for other carbamate insecticides, such as carbofuran (Dorough 1968;Metcalf et al 1968). An example of ring hydroxylation is shown below ( As mentioned above, sulfoxidation is a unique oxidation process that can sometimes activate rather than detoxicate aldicarb in Phase I reactions.…”

Section: Phase I Reactionssupporting

confidence: 53%

Evaluation of novel carbamate insecticides for neurotoxicity to non-target species

Jiang

Swale

Carlier

et al. 2013

Pesticide Biochemistry and Physiology

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Malaria (vector: Anopheles gambiae) is a major infectious disease that kills about 1 million people each year. For the improvement of its treatment and vector control during the past decades, several issues such as high medicine cost, insecticide resistance, and lack of an effective vaccine have prevented adequate control of malaria. Additionally, the low selectivity of malaria vector insecticides also presents a public health problem. The purpose of developing novel carbamate insecticides in our laboratory is to offer effective and selective insecticide options to achieve the ultimate goal of malaria control.First, 50% inhibition concentration (IC 50 ) data was collected from three mammalian AChEs with eight commercial carbamate insecticides by using the Ellman assay. The IC 50 values varied from 57 nM to 7358 nM. The AChE sensitivity pattern and level were shown to be similar between the recombinant mouse and ICR male mouse brain cortex homogenate (slope = 0.99, R 2 = 0.96).Then eight novel carbamate insecticides that are possible malaria vector control agents were selected for further neurotoxicity testing in non-target organisms. Neurotoxic esterase (NTE) assay showed that the novel carbamates did not significantly inhibit NTE, inhibition of which underlies a significant hazard for anticholinesterases, especially organophosphates, in several nontarget vertebrate organisms. The NTE activity in the presence of novel carbamate insecticides ranged from 93% to 116% of the control, while in the commercial group, bendiocarb significantly inhibited NTE, leaving only 76.5% of the initial reactivity at 1 mM inhibitor concentration.Further in vivo bioassay using Daphnia magna was conducted to compare the aquatic toxicity of commercial and novel carbamates. The data showed that except for PRC331 (3-tertbutylphenylmethylcarbamate), all novel carbamates were of similar potency as bendiocarb (LC 50 = 611 nM) for aquatic toxicity, and their LC 50 values ranged from 172 nM (PRC331) to 1109 nM.In conclusion, the novel carbamate insecticides would appear to be an improvement over commercial carbamate insecticides because of greater selectivity, negligible NTE inhibition capacity, but in some cases with potent in vivo toxicity to Daphnia magna. However, since the envisioned usage of these compounds is in bednets or as indoor residual sprays (IRS), any environmental exposures to nontarget aquatic organisms are expected to be minimal.iv ACKNOWLEDGEMENTS

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Section: Phase I Reactionssupporting

confidence: 53%

Evaluation of novel carbamate insecticides for neurotoxicity to non-target species

Jiang

Swale

Carlier

et al. 2013

Pesticide Biochemistry and Physiology

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“…Large quantities of this carbamate are particularly applied to different environments worldwide. Metabolism of carbofuran has been extensively studied in plants and animals (Dorough & Casida, 1964;Metcalf et al, 1968). In mammals, it reversibly inhibits acethylcholinesterase by carbamylation as well as others non-specific serine-containing enzymes, such as carboxylesterases and butyrylcholinesterases (Gupta, 1994).…”

Section: Carbofuran Genotoxicity and Cytotoxicity Profilesmentioning

confidence: 99%

Genetic Toxicological Profile of Carbofuran and Pirimicarb Carbamic Insecticides

Soloneski¹,

Larramendy²

2012

Insecticides - Pest Engineering

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“…Carbofuran (an insecticide) On the basis of radiolabeling studies, the major metabolite of carbofuran was identified as 3-hydroxycarbofuran, along with N-hydroxymethyl and 7-hydroxy analogues as minor components These compounds can be further transformed to the corresponding 3-keto, 3,7-dihydroxy, and 3-keto-7-hydroxy metabolites before conjugation and excretion ( Figure 16). 38 Biomimetic oxidation of carbofuran was firstly carried out using mCPBA, NaOCl, and H 2 O 2 in the presence of TCl 8 PPFeCl. Comparing the results with the metabolite profile measured in houseflies (Musca domestica), we found that in contrast to in vivo experiments, hydrolysis of carbamate side chain took place in all systems.…”

Section: Issn 1424-6376mentioning

confidence: 99%

Metalloporphyrin mediated biomimetic oxidations. A useful tool for the investigation of cytochrome P450 catalyzed oxidative metabolism

Balogh¹,

Keserü²

2004

Arkivoc

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Metabolism of 2,2-dimethyl-2,3-dihydrobenzofuran-7-N-methylcarbamate (Furadan) in plants, insects, and mamals

Cited by 136 publications

References 8 publications

Evaluation of novel carbamate insecticides for neurotoxicity to non-target species

Evaluation of novel carbamate insecticides for neurotoxicity to non-target species

Genetic Toxicological Profile of Carbofuran and Pirimicarb Carbamic Insecticides

Metalloporphyrin mediated biomimetic oxidations. A useful tool for the investigation of cytochrome P450 catalyzed oxidative metabolism

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