Buturon
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| Preferred IUPAC name
1-but-3-yn-2-yl-3-(4-chlorophenyl)-1-methylurea | |
| Identifiers | |
3D model (JSmol)
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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: | |
| GHS07: Exclamation mark[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]
Rats metabolise buturon within 4 days and remove 68% and 20% by urine and faeces respectively.[6]
Soil behaviour
[edit | edit source]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
[edit | edit source]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
[edit | edit source]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
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- ^ 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
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