Buturon

Buturon
Names
	Preferred IUPAC name 1-but-3-yn-2-yl-3-(4-chlorophenyl)-1-methylurea
Identifiers
CAS Number	3766-60-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82199;
ChEMBL	ChEMBL3185882;
ChemSpider	18451;
ECHA InfoCard	100.021.080
KEGG	C19074;
PubChem CID	19587;
UNII	1961BJU91F;
CompTox Dashboard (EPA)	DTXSID5041699 ;
	InChI InChI=1S/C12H13ClN2O/c1-4-9(2)15(3)12(16)14-11-7-5-10(13)6-8-11/h1,5-9H,2-3H3,(H,14,16) Key: BYYMILHAKOURNM-UHFFFAOYSA-N;
	SMILES CC(C#C)N(C)C(=O)NC1=CC=C(C=C1)Cl;
Properties
Chemical formula	C12H13ClN2O
Molar mass	236.70 g·mol−1
Appearance	Colourless crystalline solid
Density	1.233
Melting point	145 °C (293 °F; 418 K)
Solubility in water	30 mg/L
Solubility in acetone	279 g/L
Solubility in methanol	128 g/L
Solubility in benzene	9.8 g/L
Vapor pressure	0.01 mPa
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H311
Precautionary statements	P262, P264, P270, P280, P301+P317, P302+P352, P316, P321, P330, P361+P364, P405, P501
Flash point	>100°C
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	>1791 mg/kg (rat, oral); 500 mg/kg (rabbit, dermal);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Buturon is a methylurea, phenylurea herbicide,^[4] used to control grassy weeds, largely on cereals. It is now considered obsolete,^[1] having been first released as "Eptapur" in 1962.^[5]

Buturon's HRAC classification is Group C (Australia), Group C2 (global) or Group 5 (numeric).^[1]

Rats metabolise buturon within 4 days and remove 68% and 20% by urine and faeces respectively.^[6]

Soil behaviour

Buturon rapidly degrades in the environment, and is not persistent, though some metabolites are.^[5]

Wheat metabolises about 25% of buturon after seven days. Nutrient deficient plants metabolise it significantly faster though. The main metabolite groups are carbamates, unstable products, a group containing p-chloroacetanilide and conjugates. Nutrient-deficiency also decreases absorption and translocation, which is conjectured to passively rely on the flow of water. Plant metabolism may occur independently in roots and shoots.^[7]

Buturon has low volatility.^[1]

Safety

In a trial on mice given high daily doses of buturon, 100 to 400 mg/kg/day, and for comparison the LD₅₀ is 1791 mg/kg, buturon induced postimplantative loss and retardation of development at doses over 300 mg/kg/day, and a dose-dependent trend of cleft palate, wavy or fused ribs and hypoplasia of the upper jaw.^[8]

Usage

Buturon is usually sold as a wettable powder, to be applied on berry fruits, maize, vines, and cereals including wheat and barley, to control such weeds as spurge, annual meadow grass and foxtails.^[1]

It has been sold under the tradenames "Arisan", "Basfitox" and "Eptapur".^[1]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Hertfordshire, University of. "Buturon (Ref: H 95 (BASF))". sitem.herts.ac.uk. Pesticide Properties Database.
^ ^a ^b ^c "buturon". www.chemsrc.com. Retrieved 29 May 2025.
^ "Buturon PESTANAL SDS". Retrieved 29 May 2025.
^ "Buturon". pubchem.ncbi.nlm.nih.gov. PubChem. Retrieved 29 May 2025.
^ ^a ^b Reiml, Dieter; Scheunert, Irene; Korte, Friedhelm (January 1989). "Leaching of conversion products of [14C]-buturon from soil during 12 years after application". Journal of Agricultural and Food Chemistry. 37 (1): 244–248. Bibcode:1989JAFC...37..244R. doi:10.1021/jf00085a057.
^ Grunow, W.; Altmann, H. -J.; Böhme, Chr. (1 January 1978). "Metabolisierung von Buturon in der Ratte". Food and Cosmetics Toxicology. 16 (4): 349–353. doi:10.1016/S0015-6264(78)80006-6. PMID 711055.
^ HAQUE, A.-U., WEISGERBER, I., & KLEIN, W. (1977). Absorption, Efflux, and Metabolism of the Herbicide [14C]Buturon as Affected by Plant Nutrition. Journal of Experimental Botany, 28(103), 468–479. http://www.jstor.org/stable/23689388
^ Matthiaschk, G.; Roll, R. (1 December 1977). "Untersuchungen über die Embryotoxizität von Monolinuron und Buturon bei NMRI-Mäusen". Archives of Toxicology. 38 (4): 261–274. Bibcode:1977ArTox..38..261M. doi:10.1007/BF00352031.

[database-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Hertfordshire, University of. "Buturon (Ref: H 95 (BASF))". sitem.herts.ac.uk. Pesticide Properties Database.

[chemsrc-2] "buturon". www.chemsrc.com. Retrieved 29 May 2025.

[3] "Buturon PESTANAL SDS". Retrieved 29 May 2025.

[pubchem-4] "Buturon". pubchem.ncbi.nlm.nih.gov. PubChem. Retrieved 29 May 2025.

[reimi-5] Reiml, Dieter; Scheunert, Irene; Korte, Friedhelm (January 1989). "Leaching of conversion products of [14C]-buturon from soil during 12 years after application". Journal of Agricultural and Food Chemistry. 37 (1): 244–248. Bibcode:1989JAFC...37..244R. doi:10.1021/jf00085a057.

[german_rat_torturers-6] Grunow, W.; Altmann, H. -J.; Böhme, Chr. (1 January 1978). "Metabolisierung von Buturon in der Ratte". Food and Cosmetics Toxicology. 16 (4): 349–353. doi:10.1016/S0015-6264(78)80006-6. PMID 711055.

[7] HAQUE, A.-U., WEISGERBER, I., & KLEIN, W. (1977). Absorption, Efflux, and Metabolism of the Herbicide [14C]Buturon as Affected by Plant Nutrition. Journal of Experimental Botany, 28(103), 468–479. http://www.jstor.org/stable/23689388

[8] Matthiaschk, G.; Roll, R. (1 December 1977). "Untersuchungen über die Embryotoxizität von Monolinuron und Buturon bei NMRI-Mäusen". Archives of Toxicology. 38 (4): 261–274. Bibcode:1977ArTox..38..261M. doi:10.1007/BF00352031.

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