Insecticide Metabolism, Nature of Toxic Metabolites Formed in Mammals, Insects, and Plants from 3-(Dimethoxyphosphinyloxy)-N-N-dimethyl-cis-croton-amide and Its N-Methyl Analog

Menzer, Robert E.; Casida, J. E.

doi:10.1021/jf60138a001

Cited by 98 publications

(50 citation statements)

References 12 publications

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“…Phosphatase activities were observed in both cultures, and it was suggested that the phosphates identified may be mono‐ and dimethyl phosphates (Bhadbhade et al , 2002b). Dimethyl‐ and monomethyl phosphates were involved as intermediates in monocrotophos degradation in plants and animals (Menzer & Cassida, 1965; Muck, 1994). Another intermediate identified during monocrotophos degradation was methylamine, produced by an esterase enzyme.…”

Section: Microbial Degradation Of Organophosphorus Compoundsmentioning

confidence: 99%

Microbial degradation of organophosphorus compounds

Singh¹,

Walker²

2006

FEMS Microbiol Rev

967

524

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Synthetic organophosphorus compounds are used as pesticides, plasticizers, air fuel ingredients and chemical warfare agents. Organophosphorus compounds are the most widely used insecticides, accounting for an estimated 34% of world-wide insecticide sales. Contamination of soil from pesticides as a result of their bulk handling at the farmyard or following application in the field or accidental release may lead occasionally to contamination of surface and ground water. Several reports suggest that a wide range of water and terrestrial ecosystems may be contaminated with organophosphorus compounds. These compounds possess high mammalian toxicity and it is therefore essential to remove them from the environments. In addition, about 200,000 metric tons of nerve (chemical warfare) agents have to be destroyed world-wide under Chemical Weapons Convention (1993). Bioremediation can offer an efficient and cheap option for decontamination of polluted ecosystems and destruction of nerve agents. The first micro-organism that could degrade organophosphorus compounds was isolated in 1973 and identified as Flavobacterium sp. Since then several bacterial and a few fungal species have been isolated which can degrade a wide range of organophosphorus compounds in liquid cultures and soil systems. The biochemistry of organophosphorus compound degradation by most of the bacteria seems to be identical, in which a structurally similar enzyme called organophosphate hydrolase or phosphotriesterase catalyzes the first step of the degradation. organophosphate hydrolase encoding gene opd (organophosphate degrading) gene has been isolated from geographically different regions and taxonomically different species. This gene has been sequenced, cloned in different organisms, and altered for better activity and stability. Recently, genes with similar function but different sequences have also been isolated and characterized. Engineered microorganisms have been tested for their ability to degrade different organophosphorus pollutants, including nerve agents. In this article, we review and propose pathways for degradation of some organophosphorus compounds by microorganisms. Isolation, characterization, utilization and manipulation of the major detoxifying enzymes and the molecular basis of degradation are discussed. The major achievements and technological advancements towards bioremediation of organophosphorus compounds, limitations of available technologies and future challenge are also discussed.

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Section: Microbial Degradation Of Organophosphorus Compoundsmentioning

confidence: 99%

Microbial degradation of organophosphorus compounds

Singh¹,

Walker²

2006

FEMS Microbiol Rev

967

524

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“…zThe metabolic fate of MCP in plants and animals is well documented by Bull and Lindquist (1964), Menzer and Cassida (1965), Beynon et al (1973) and Mucke (1994). Bacteria capable of degrading several pesticides have been isolated from soil.…”

Section: Introductionmentioning

confidence: 99%

Biomineralization of an organophosphorus pesticide, Monocrotophos, by soil bacteria

2002

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Aims: To study biomineralization of Monocrotophos (MCP) and identify the metabolites formed during biodegradation. Methods and Results: Two cultures, namely Arthrobacter atrocyaneus MCM B-425 and Bacillus megaterium MCM B-423, were isolated by enrichment and adaptation culture technique from soil exposed to MCP. The isolates were able to degrade MCP to the extent of 93% and 83%, respectively, from synthetic medium containing MCP at the concentration of 1000 mg l )1 , within 8 d, under shake culture condition at 30°C. The cultures degraded MCP to carbon dioxide, ammonia and phosphates through formation of one unknown compound -Metabolite I, valeric or acetic acid and methylamine, as intermediate metabolites.The enzymes phosphatase and esterase, reported to be involved in biodegradation of organophosphorus compounds, were detected in both the organisms. Conclusions: Arthrobacter atrocyaneus MCM B-425 and B. megaterium MCM B-423 isolated from soil exposed to MCP were able to mineralize MCP to carbon dioxide, ammonia and phosphates.Significance and Impact of the Study: Pathway for biodegradation of MCP in plants and animals has been reported. A microbial metabolic pathway of degradation involving phosphatase and esterase enzymes has been proposed. The microbial cultures could be used for bioremediation of wastewater or soil contaminated with Monocrotophos.

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“…The consecutive steps of N-methyl hydroxylation and de methylation of the N,N-dimethyl group of dicrotophos were initially indicated by in vivo studies (Bull and Lindquist, 1964). The sequence was later elucidated with an in vitro microsomal system using an elegant double-labeling C 2 p and 14C) technique (Menzer and Casida, 1965). Subsequent studies have shown an identical type of N-ethyl oxidation for a closely related insecticide, phosphamidon (Bull etat., 1967;Clemons and Menzer, 1968;Lucier and Menzer, 1971).…”

Section: 1 0- $- and N-alkyl Hydroxylationmentioning

confidence: 99%