Urease inhibitory activity associated with N-(n-butyl)thiophosphoric triamide is due to formation of its oxon analog

Creason, Gary L.; Schmitt, Melanie; Douglass, E.A.; Hendrickson, L. L.

doi:10.1016/0038-0717(90)90088-h

Cited by 79 publications

(41 citation statements)

References 3 publications

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“…Taking these into account it is likely that the PA derivative 2B10 undergoes some structural transformation caused by soil microbiota as it is known to occur with NBPT. 16 It is well known that NBPT is sensitive to heat. 44 For the most active derivatives on soil (2A7 and 2D2), thermogravimetric analysis shows no decomposition of such compounds up to 170 o C ( Figure S1; Supplementary Information section).…”

Section: Discussionmentioning

confidence: 99%

“…[13][14][15] Indeed, the N-(butyl)thiophosphoric triamide (NBPT) was found to become a very effective inhibitor when transformed to its corresponding oxo-derivative (oxo-NBPT) by soil microorganisms. 16 The NBPT effectiveness is directly related to soil properties in which low concentration of this urease proinhibitor is needed to achieve the desired result in temperate soils while greater concentrations are required for tropical soils. [17][18][19][20] Additionally, NBPT is more efficient in neutral soils with limited organic matter.…”

Section: Introductionmentioning

confidence: 99%

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Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

Horta¹,

Mota²,

Barbosa³

et al. 2016

J. Braz. Chem. Soc.

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The plant phenolic natural products (PNPs) protocatechuic aldehyde, syringaldehyde and vanillin were used as platforms for obtaining four urease inhibitors. Urea (urease substrate) or thiourea (urease inhibitor) core was added to the structure of newly synthesized compounds to provide inhibitors up to 230-fold more active than the PNPs they originated from. The PNP derivatives are mixed inhibitors with higher affinity to urease active site. Two compounds were as efficient as N-(butyl)thiophosphoric triamide (NBPT) toward soil. Overall, PNPs derivatives are promising urease inhibitors for use as additive in urea-based fertilizers formulations.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

Horta¹,

Mota²,

Barbosa³

et al. 2016

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…The active inhibitory chemical species has been thought to be the oxon derivative N-(n-butyl) phosphoric triamide (NBPTO, Fig. 5a) which has been found to display 50% inhibition at a 1000-fold lower concentration than the parent NBPT compound (Creason et al 1990;Font et al 2008;Kot et al 2001). NBPTO is slowly but spontaneously formed from NBPT under aerobic conditions.…”

Section: Ammonia Emission Mitigation By Urease Inhibitorsmentioning

confidence: 99%

The molecular processes of urea hydrolysis in relation to ammonia emissions from agriculture

Sigurdarson

Svane

Karring

2018

Rev Environ Sci Biotechnol

243

129

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Ammonia emissions from the agricultural sector give rise to numerous environmental and societal concerns and represent an economic challenge in crop farming, causing a loss of fertilizer nitrogen. Ammonia emissions from agriculture originate from manure slurry (livestock housing, storage, and fertilization of fields) as well as urea-based mineral fertilizers. Consequently, political attention has been given to ammonia volatilization, and regulations of ammonia emissions have been implemented in several countries. The molecular cause of the emission is the enzyme urease, which catalyzes the hydrolysis of urea to ammonia and carbonic acid. Urease is present in many different organisms, encompassing bacteria, fungi, and plants. In agriculture, microorganisms found in animal fecal matter and soil are responsible for urea hydrolysis. One strategy to reduce ammonia emissions is the application of urease inhibitors as additives to urea-based synthetic fertilizers and manure slurry to block the formation of ammonia. However, treatment of the manure slurry with urease inhibitors is associated with increased livestock production costs and has not yet been commercialized. Thus, development of novel, environmentally friendly and cost-effective technologies for ammonia emission mitigation is important. This mini-review describes the challenges associated with the volatilization of ammonia in agriculture and provides an overview of the molecular processes of urea hydrolysis and ammonia emissions. Different technologies and strategies to reduce ammonia emissions are described with a special focus on the use of urease inhibitors. The mechanisms of action and efficiency of the most important urease inhibitors in relation to agriculture will be briefly discussed.

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“…After application, nBTPT is quickly converted to its oxygen analog N-(n-butyl) phosphoric triamide) (NBPT) (Eq. 5.1.1), which is the actual UI (McCarty et al, 1989;Christianson et al, 1990;Creason et al, 1990), and it is bound and moves along with urea molecule in the soil (Christianson & Howard, 1994). The conversion of nBTPT to NBPT is rapid, occurring within minutes/hours in aerobic soils (Byrnes & Freney, 1995), but can take several days in the floodwater of tropical soils.…”

Section: Factors Affecting N 2 O and N 2 Emissions And Possible Mitigmentioning

confidence: 99%

Emissions of Nitrous Oxide (N2O) and Di-Nitrogen (N2) from the Agricultural Landscapes, Sources, Sinks, and Factors Affecting N2O and N2 Ratios

Zaman¹,

Nguyen²,

Šimek³

et al. 2012

Greenhouse Gases - Emission, Measurement and Management

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Urease inhibitory activity associated with N-(n-butyl)thiophosphoric triamide is due to formation of its oxon analog

Cited by 79 publications

References 3 publications

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

Urease Inhibitors of Agricultural Interest Inspired by Structures of Plant Phenolic Aldehydes

The molecular processes of urea hydrolysis in relation to ammonia emissions from agriculture

Emissions of Nitrous Oxide (N2O) and Di-Nitrogen (N2) from the Agricultural Landscapes, Sources, Sinks, and Factors Affecting N2O and N2 Ratios

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