Buturon
Chemical compound
From Wikipedia, the free encyclopedia
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]
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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's HRAC classification is Group C (Australia), Group C2 (global) or Group 5 (numeric).[1]
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.[6]
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.[7]
Rats metabolise buturon within 4 days and remove 68% and 20% by urine and faeces respectively.[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]