Buturon
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| Names | |
|---|---|
| Preferred IUPAC name
1-but-3-yn-2-yl-3-(4-chlorophenyl)-1-methylurea | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.021.080 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C12H13ClN2O | |
| Molar mass | 236.70 g·mol−1 |
| Appearance | Colourless crystalline solid[1] |
| Density | 1.233[2] |
| Melting point | 145 °C (293 °F; 418 K)[1] |
| 30 mg/L[1] | |
| Solubility in acetone | 279 g/L[1] |
| Solubility in methanol | 128 g/L[1] |
| Solubility in benzene | 9.8 g/L[1] |
| Vapor pressure | 0.01 mPa[1] |
| Hazards | |
| GHS labelling: | |
 [2] | |
| Danger | |
| H302, H311[1] | |
| P262, P264, P270, P280, P301+P317, P302+P352, P316, P321, P330, P361+P364, P405, P501 | |
| Flash point | >100°C[2] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Soil behaviour
[edit]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.[6]
Buturon has low volatility.[1]
Safety
[edit]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.[7]
Rats metabolise buturon within 4 days and remove 68% and 20% by urine and faeces respectively.[8]
Usage
[edit]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
[edit]- 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Hertfordshire, University of. "Buturon (Ref: H 95 (BASF))". sitem.herts.ac.uk. Pesticide Properties Database.
- 1 2 3 "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.
- 1 2 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.
- ↑ 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.
- ↑ 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.