Isobutylidenediurea

Isobutylidenediurea (abbreviated IBDU) is an organic compound with the formula (CH₃)₂CHCH{NHC(O)NH₂}₂. It is a derivative of urea (OC(NH₂)₂), which itself is highly soluble in water, but IBDU is not. It functions as a controlled-release fertiliser owing to its low solubility, which limits the rate of its hydrolysis to urea, which is a fast-acting fertiliser.[1]

Isobutylidenediurea

Names
Other names Isodur; Diureidoisobutane; Isobutylenediurea; Isobutylidene biurea; 1,1-Diureidisobutane; Isobutylidendiharnstoff;1,1'-Isobutylidenedi-urea; 1,1'-Isobutylidenebisurea; N,N-(isobutylidene)diurea; N,N-(Isobutylidene)bisurea
Identifiers
CAS Number	6104-30-9
3D model (JSmol)	Interactive image
ChemSpider	21083
ECHA InfoCard	100.025.505
EC Number	228-055-8
MeSH	C014058
PubChem CID	22478
UNII	20K1225668
CompTox Dashboard (EPA)	DTXSID8027614
InChI InChI=1S/C6H14N4O2/c1-3(2)4(9-5(7)11)10-6(8)12/h3-4H,1-2H3,(H3,7,9,11)(H3,8,10,12) Key: QFHMNFAUXJAINK-UHFFFAOYSA-N InChI=1/C6H14N4O2/c1-3(2)4(9-5(7)11)10-6(8)12/h3-4H,1-2H3,(H3,7,9,11)(H3,8,10,12) Key: QFHMNFAUXJAINK-UHFFFAOYAM
SMILES CC(C)C(NC(=O)N)NC(=O)N
Properties
Chemical formula	C6H14N4O2
Molar mass	174.204 g·mol^−1
Appearance	White solid
Solubility in water	Low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is produced by the condensation reaction of isobutyraldehyde and two equivalents of urea:

(CH₃)₂CHCHO + 2 OC(NH₂)₂ → (CH₃)₂CHCH{NHC(O)NH₂}₂ + H₂O

The controlled-release process is the reverse of the above reaction, which only occurs after the IBDU dissolves.

References

1. C. Nitschke, G. Scherr (2012). "Urea Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o04.CS1 maint: uses authors parameter (link)