Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest

Brito, Tiago O.; Souza, Aline X. de; Mota, Yane C. C.; Morais, Vinicius Stefano Santos; Souza, Leandro Torres de; Fátima, Ângelo de; Macedo, Fernando; Modolo, Luzia V.

doi:10.1039/c5ra07886e

Cited by 51 publications

(27 citation statements)

References 52 publications

(62 reference statements)

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“…The high-ammonia volatilization measured for RTB68 corroborated a previous report, in which jack bean urease had low efficacy in vitro (Brito et al, 2015). In contrast, the results of the present work do not corroborate those reported for soils of Brazilian Cerrado, where RTB68 ("compound 18") inhibited soil urease as effectively as NBPT.…”

Section: Resultssupporting

confidence: 56%

“…They are stable during storage and transport. In these respects, they are superior to NBPT (Brito et al, 2015). Benzimidazole derivatives are also potent urease inhibitors (Santosh et al, 2011).…”

Section: Introductionmentioning

confidence: 99%

“…Exploratory-phase studies with BTUs (Brito et al, 2015) and benzimidazoles (Araújo, 2015), in both laboratory and field conditions, have produced promising results. Therefore, it is necessary to test and elucidate their efficacies against soil ureases.…”

Section: Introductionmentioning

confidence: 99%

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Use of urease inhibitors to reduce ammonia volatilization in Amazonian soils

Barberena

Espindula

Araújo

et al. 2019

Pesq. agropec. bras.

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The objective of this work was to evaluate urease inhibitors for the reduction of ammonia volatilization in Amazonian soils. The work was carried out on a clayey yellow Oxisol, a clayey red Oxisol, and on a light silty Ultisol. Each experiment was conducted in split plots, using standard urea, urea + a benzimidazole-type urease inhibitor (BZI1), urea + a benzoylthiourea-type urease inhibitor (RTB68), urea + N-(n-butyl) triamide thiophosphate (NBPT), or a fertilizer-free control. Volatilized ammonia was collected at 48, 96, 144, 192, 240, 288, 336, and 384 hours after fertilization. Ammonia volatilization reached a maximum at 144 hours in the urea, urea + benzimidazole, and urea + benzoylthiourea treatments. A peak level was reached at 192 and 288 hours in the urea + N-(n-butyl) triamide thiophosphate treatment. In yellow Oxisols, benzimidazole and benzoylthiourea reduced the ammonia losses by 22 and 10%, respectively, in soils without urease inhibitors. However, neither of these agents significantly reduced ammonia volatilization at the rate determined for standard urea in red Oxisols or Ultisols. N-(n-butyl) triamide thiophosphate is the most efficient urease inhibitor for the soils of southwestern Amazonia.

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Section: Resultssupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

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Use of urease inhibitors to reduce ammonia volatilization in Amazonian soils

Barberena

Espindula

Araújo

et al. 2019

Pesq. agropec. bras.

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“…Recently, our group has described that phosphoramidate, benzothiazole and benzoylthiourea compounds are also promising urease inhibitors. [10][11][12] Up to now, phosphorodiamide and phosphorotriamide derivatives Vol. 27, No.…”

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.

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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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“…The screening for identifying potential urease inhibitors was done by incubating each 2,5‐bis(alkyl/arylamino)‐1,4‐benzoquinones ( 1 – 12 ) at 5 μ m (5,000 n m ) in reactions containing 50 m m phosphate buffer (pH 7.4), urea (10 m m ), and 1.25×10 −2 U Canavalia ensiformis (jack bean) type III urease (Sigma U‐1500‐100 kU). Each mixture was incubated for 15 min at 25 °C, and the reactions were interrupted according to Weatherburn, with modifications reported by Brito et al . The ammonium concentration was determined by the phenol‐hypochlorite assay (measured at 636 nm), and the inhibition percentage [INH (%)] was calculated using the equation: INH (%)=100–[(AINH/AB)×100], where AINH and AB are ammonium concentration in the tubes with and without inhibitor, respectively.…”

Section: Methodsmentioning

confidence: 99%

Antiureolytic Activity of Substituted 2,5‐Diaminobenzoquinones

Nain-Pérez

Barbosa

Rodríguez-Hernández

et al. 2019

Chemistry & Biodiversity

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A series of 2,5-bis(alkyl/arylamino)-1,4-benzoquinones (1-12) were investigated in vitro for their potential to inhibit the activity of jack bean urease. Compounds 1 -6, 8, 9, 11 and 12 effectively inhibited the jack bean urease activity by 90.8 % when tested at 5 μM, whereas 7 and 10 had relatively little effect. The IC 50 for most compounds was in the nanomolar range (31.4 nM and 36.0 nM for 2 and 8, respectively). The mechanism of enzyme inhibition shown by 2 and 8 is typical of mixed-type inhibitors, whose affinity for the active site is over 6-and 2-fold higher (K i = 30.0 and 22.8 nM, for 2 and 8, respectively) than that of an allosteric site. Molecular docking studies revealed that both 2 and 8 establish hydrogen bonds with the amino acids residues Asp494, Met588, His593 and Ala636 in the active site of jack bean urease. These results indicate that such aminoquinones are useful leads for the development of more efficient urease inhibitors of wider utility. Scheme 1. Structures of 2,5-bis(alky/arylamino)-1,4-benzoquinones used in this study.

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Design, syntheses and evaluation of benzoylthioureas as urease inhibitors of agricultural interest

Abstract: Urea is one of the most used nitrogen fertilizers worldwide.

Cited by 51 publications

References 52 publications

Use of urease inhibitors to reduce ammonia volatilization in Amazonian soils

Use of urease inhibitors to reduce ammonia volatilization in Amazonian soils

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

Antiureolytic Activity of Substituted 2,5‐Diaminobenzoquinones

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