Buturon

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Buturon
Buturon v2.svg
Names
Preferred IUPAC name
1-but-3-yn-2-yl-3-(4-chlorophenyl)-1-methylurea
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.021.080 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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
  • CC(C#C)N(C)C(=O)NC1=CC=C(C=C1)Cl
Properties
C12H13ClN2O
Molar mass 236.70 g·mol−1
AppearanceColourless 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:
GHS-pictogram-exclam.svg [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):
  • >1791 mg/kg (rat, oral)
  • 500 mg/kg (rabbit, dermal) [1] [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

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

  1. 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.
  2. 1 2 3 "buturon". www.chemsrc.com. Retrieved 29 May 2025.
  3. ↑ "Buturon PESTANAL SDS" . Retrieved 29 May 2025.
  4. ↑ "Buturon". pubchem.ncbi.nlm.nih.gov. PubChem. Retrieved 29 May 2025.
  5. 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.
  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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