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Difenoxuron

Names
IUPAC name 3--1,1-dimethylurea
Identifiers
CAS Number	14214-32-5
3D model (JSmol)	Interactive image
ChemSpider	24757
ECHA InfoCard	100.034.592
EC Number	238-068-0
PubChem CID	26576
UNII	C74279E50O
CompTox Dashboard (EPA)	DTXSID9041863
InChI InChI=1S/C16H18N2O3/c1-18(2)16(19)17-12-4-6-14(7-5-12)21-15-10-8-13(20-3)9-11-15/h4-11H,1-3H3,(H,17,19)Key: AMVYOVYGIJXTQB-UHFFFAOYSA-N
SMILES CN(C)C(=O)NC1=CC=C(C=C1)OC2=CC=C(C=C2)OC
Properties
Chemical formula	C16H18N2O3
Molar mass	286.331 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Difenoxuron is a phenylurea herbicide. It is also called 3--1,1-dimethylurea and is soluble in acetone. There are very few studies about the genotocicity of difenoxuron and these studies are inconcordant but there appears to be a dose dependent relationship between the rate of observed chromosomal aberrations and rate of difenoxuron. It appears as a solid powder, and is stereochemically achiral.

Difenoxuron's hazards include acute toxicity caused by oral ingestion, and acute toxicity of inhalation. It has no notable explosion hazards.

Difenoxuron is commercially known as "Lironion", possibly taking partial inspiration from onions, which it is thereto most notably applied. In the Russian language, difenoxuron is called "дифеноксурон" (transliterated: difenoksuron).

Liming in Boddington soil has been shown by a 1976 study to increase the herbicidal toxicity of difenoxuron by two to three times compared to soil without the additional level of liming. The mammalian oral LD50 of difenoxuron is >7750 mg/kg, and the dermal LD50 is over 2150 mg/kg. The mode of action of the herbicidal properties of difenoxuron is the inhibition of photosynthesis at photosystem II by binding to protein and halting electron transfer. The target plant of the herbicide application suffers then from inhibited CO2 fixation and lack of production of energy, preventing it from growing.

Difenoxuron is also used on carrots, jojoba, and celery.

References

1. "difenoxuron data sheet". www.bcpcpesticidecompendium.org.
2. "Difenoxuron". www.chemservice.com.
3. Federico, Concetta; Motta, Salvatore; Palmieri, Cristina; Pappalardo, Matteo; Librando, Vito; Saccone, Salvatore (18 March 2011). "Phenylurea herbicides induce cytogenetic effects in Chinese hamster cell lines". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 721 (1): 89–94. Bibcode:2011MRGTE.721...89F. doi:10.1016/j.mrgentox.2010.12.013. PMID 21238602.
4. "Difenoxuron featured". MedKoo Biosciences, Inc. Retrieved 20 November 2024.
5. "GSRS". gsrs.ncats.nih.gov.
6. "Difenoxuron SDS" (PDF). cdn.chemservice.com/. Retrieved 20 November 2024.
7. Federico, Concetta; Motta, Salvatore; Palmieri, Cristina; Pappalardo, Matteo; Librando, Vito; Saccone, Salvatore (18 March 2011). "Phenylurea herbicides induce cytogenetic effects in Chinese hamster cell lines". Mutation Research/Genetic Toxicology and Environmental Mutagenesis. 721 (1): 89–94. Bibcode:2011MRGTE.721...89F. doi:10.1016/j.mrgentox.2010.12.013. ISSN 1383-5718. PMID 21238602. Retrieved 20 November 2024.
8. "difenoxuron data sheet". www.bcpcpesticidecompendium.org.
9. Richardson, W. G.; Banting, J. D. (June 1977). "The phytotoxicity of various herbicides in two sandy loam soils and the effect of liming". Weed Research. 17 (3): 203–207. Bibcode:1977WeedR..17..203R. doi:10.1111/j.1365-3180.1977.tb00467.x.
10. "Difenoxuron". Grainews.
11. "imtrade advert difenoxuron 800 wg" (PDF).
12. "IMTRADE LINURON 800 WG HERBICIDE" (PDF). Retrieved 20 November 2024.

• Herbicides
• Ureas
• Diphenyl ethers