N-(n-Butyl)thiophosphoric triamide

N-(n-Butyl)thiophosphoric triamide (NBPT) is the organophosphorus compound with the formula SP(NH₂)₂(NHC₄H₉). It is an amide of thiophosphoric acid. A white solid, NBPT is an "enhanced efficiency fertilizer", intended to limit the release of nitrogen-containing gases following fertilization.^[1] Regarding its chemical structure, the molecule features tetrahedral phosphorus bonded to sulfur and three amido groups.

N-(n-Butyl)thiophosphoric triamide

Names
Other names Agrotain N-Butylphosphorothioic triamide
Identifiers
CAS Number	94317-64-3
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3186430
ChemSpider	84405
ECHA InfoCard	100.103.392
EC Number	435-740-7
PubChem CID	93502
UNII	A6103OK7GF
CompTox Dashboard (EPA)	DTXSID4044747
InChI InChI=1S/C4H14N3PS/c1-2-3-4-7-8(5,6)9/h2-4H2,1H3,(H5,5,6,7,9) Key: HEPPIYNOUFWEPP-UHFFFAOYSA-N
SMILES CCCCNP(=S)(N)N
Properties
Chemical formula	C4H14N3PS
Molar mass	167.21 g·mol−1
Appearance	white solid
Melting point	54 °C (129 °F; 327 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H318, H361
Precautionary statements	P201, P202, P280, P281, P305+P351+P338, P308+P313, P310, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Use

NBPT functions as an inhibitor of the enzyme urease.^[2] Urease, pervasive in soil microorganisms, converts urea into ammonia, which is susceptible to volatilization if produced faster than it can be utilized by plants. Approximately 0.5% by weight NBPT is mixed with the urea.^[3]

See also

• Phenyl phosphorodiamidate, another urease inhibitor

References

1. Rose, Terry J.; Wood, Rachel H.; Rose, Michael T.; Van Zwieten, Lukas (2018). "A re-evaluation of the agronomic effectiveness of the nitrification inhibitors DCD and DMPP and the Urease Inhibitor NBPT". Agriculture, Ecosystems & Environment. 252: 69–73. Bibcode:2018AgEE..252...69R. doi:10.1016/j.agee.2017.10.008.
2. Pan, Baobao; Lam, Shu Kee; Mosier, Arvin; Luo, Yiqi; Chen, Deli (2016). "Ammonia Volatilization from Synthetic Fertilizers and its Mitigation Strategies: A Global Synthesis". Agriculture, Ecosystems & Environment. 232: 283–289. Bibcode:2016AgEE..232..283P. doi:10.1016/j.agee.2016.08.019.
3. Zaman, M.; Zaman, S.; Quin, B.F; Kurepin, L.V; Shaheen, S.; Nawaz, S.; Dawar, K.M (2014). "Improving Pasture Growth and Urea Efficiency Using N inhibitor, Molybdenum and Elemental Sulphur". Journal of Soil Science and Plant Nutrition. doi:10.4067/S0718-95162014005000020.