Phenyl phosphorodiamidate

Phenyl phosphorodiamidate is an organophosphorus compound with the formula C6H5OP(O)(NH2)2. A white solid, it is used as an inhibitor of urease,[1] an enzyme that accelerates the hydrolysis of urea. In this way, phenyl phosphorodiamidate enhances the effectiveness of urea-based fertilizers. It is a component of the technology of controlled release fertilizers.[2]

Phenyl phosphorodiamidate
Names
Preferred IUPAC name
Phenyl phosphorodiamidate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.028.380
EC Number
  • 231-218-6
UNII
  • InChI=1S/C6H9N2O2P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H,(H4,7,8,9)
    Key: AYRRNFHDJUXLEQ-UHFFFAOYSA-N
  • C1=CC=C(C=C1)OP(=O)(N)N
Properties
C6H9N2O2P
Molar mass 172.124 g·mol−1
Appearance white solid
Melting point 185 °C (365 °F; 458 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H319
P264, P270, P280, P301+P312, P305+P351+P338, P330, P337+P313, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In terms of its molecular structure, phenyl phosphorodiamidate is a tetrahedral molecule structurally related to urea, hence its inhibitory function. It is a derivative of phosphoryl chloride.

See also

References
  1. Gholivand, Khodayar; Pooyan, Mahsa; Mohammadpanah, Fahimeh; Pirastefar, Foroogh; Junk, Peter C.; Wang, Jun; Ebrahimi Valmoozi, Ali Asghar; Mani-Varnosfaderani, Ahmad (2019). "Synthesis, Crystal Structure and Biological Evaluation of New Phosphoramide Derivatives as Urease Inhibitors Using Docking, QSAR and Kinetic Studies". Bioorganic Chemistry. 86: 482–493. doi:10.1016/j.bioorg.2019.01.064. PMID 30772649. S2CID 73460771.
  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. doi:10.1016/j.agee.2016.08.019.
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