Microbial formation of methylamine from 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Wright, K. A.; Cain, Ronald B.

doi:10.1016/0038-0717(69)90029-7

Cited by 14 publications

(13 citation statements)

References 23 publications

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“…In the present paper we describe the metabolism of N-methylisonicotinate by an Achromobacter, washed suspensions of which released stoicheiometric amounts of methylamine from the N-methyl group of the molecule (Wright & Cain, 1969). No other products accumulated with washed cells, but by using cell-free extracts, we have been able to show that the carbon skeleton of N-methylisonicotinate can be accounted for as C02, formate, succinate and methylamine (Wright & Cain, 1970).…”

mentioning

confidence: 77%

“…The isolation of the organism used and its cultivation in large volumes have been described by Wright & Cain (1969).…”

Section: Organismmentioning

confidence: 99%

“…Methylamine was detected by t.l.c. on silica gel or kieselguhr (0.25mm-thick) plates with solvent H and was determined colorimetrically or enzymically after microdiffusion in Conway units for 18h as described by Wright & Cain (1969).…”

Section: Determinationsmentioning

confidence: 99%

“…N-Methylisonicotinate was, however, rapidly decomposed in soil (Calderbank, 1968). Micro-organisms with this ability were isolated from soil by Wright & Cain (1969) and by Orpin et al (1971), but the metabolic pathways by which these organisms degraded N-methylisonicotinate appeared to differ considerably.…”

mentioning

confidence: 99%

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Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Wright

Cain

1972

Biochemical Journal

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1. A bacterium, Achromobacter D, isolated from garden soil by elective culture, utilized N-methylisonicotinic acid (4-carboxy-1-methylpyridinium chloride) as sole carbon source. 2. Extracts of N-methylisonicotinate-grown cells oxidized this substrate only after supplementation with a source of nicotinamide nucleotides and then consumed 1 mol of O(2) and released 1 mol of CO(2)/mol of N-methylisonicotinate supplied. 3. The N-methyl group of the substrate was released as methylamine whereas the five C atoms of the pyridine ring were accounted for as succinate and formate. The CO(2) evolved by extracts was believed to derive from the carboxyl group on C-4 of the heterocyclic ring. 4. The immediate precursor of the succinate end-product was succinic semialdehyde; the inducible nature of succinic semialdehyde dehydrogenase in N-methylisonicotinate-grown cells supported this finding. 5. There was no evidence for monohydroxylation of the ring, but the time sequence of the appearance of the end-products indicated that the oxygen-requiring, NADH-requiring and decarboxylation steps clearly preceded the formation of methylamine and succinate. 6. The results are consistent with the oxidative cleavage of a partially reduced heterocyclic ring followed by several hydrolytic and dehydrogenase steps resulting in the appearance of the end-products.

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mentioning

confidence: 77%

“…The isolation of the organism used and its cultivation in large volumes have been described by Wright & Cain (1969).…”

Section: Organismmentioning

confidence: 99%

Section: Determinationsmentioning

confidence: 99%

mentioning

confidence: 99%

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Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Wright

Cain

1972

Biochemical Journal

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“…Recently, Lee et al 19 have shown that paraquat can be degraded microbially when sorbed to plant tissues and in light this may occur together with photolysis. The main photochemical degradation product (Fig 1, 3 ) is the betaine 1‐methyl‐4‐carboxypyridinium; this is not strongly sorbed to soil and is rapidly degraded by microbial attack yielding methylamine from the methyl moiety and ultimately a variety of other fragments including carbon dioxide, fumarate and succinate 20–23. Thus paraquat is not intrinsically stable either to photolysis or microbial metabolism but, once in the soil matrix, very strong binding reduces the bioavailability and hence greatly slows breakdown.…”

Section: Paraquat Behaviour In Plants and Soilmentioning

confidence: 99%

Paraquat and sustainable agriculture

Bromilow

2003

Pest Management Science

168

104

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Sustainable agriculture is essential for man's survival, especially given our rapidly increasing population. Expansion of agriculture into remaining areas of natural vegetation is undesirable, as this would reduce biodiversity on the planet. Maintaining or indeed improving crop yields on existing farmed land, whether on a smallholder scale or on larger farms, is thus necessary. One of the limiting factors is often weed control; biological control of weeds is generally of limited use and mechanical control is either often difficult with machinery or very laborious by hand. Thus the use of herbicides has become very important. Minimum cultivation can also be important, as it reduces the power required to work the soil, limits erosion and helps to maintain the organic matter content of the soil. This last aspect helps preserve both the structure of soil and its populations of organisms, and also sustains the Earth's soil as a massive sink for carbon, an important consideration in the light of global warming. The introduction of the bipyridinium herbicide paraquat in the early 1960s greatly facilitated weed control in many crops. Paraquat has the unusual property of being active only by direct spray onto plants and not by uptake from soil in which strong binding deactivates it. Together with its rapid action in light in killing green plant tissue, such properties allow paraquat to be used in many crops, including those grown by low-tillage methods. This paper reviews the ways in which agricultural systems have been and are being developed to make use of these properties, and provides a risk/benefit analysis of the world-wide use of paraquat over nearly 40 years.

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Simulation and experimental analysis of the influence of herbicides on soil nitrification

Domsch

Paul

1974

Arch. Microbiol.

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Microbial formation of methylamine from 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Cited by 14 publications

References 23 publications

Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Paraquat and sustainable agriculture

Simulation and experimental analysis of the influence of herbicides on soil nitrification

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