Noruron

Noruron
Names
Preferred IUPAC name
rac-N,N-dimethyl-N'-[(3aR,4S,5R,7S,7aR)-octahydro-1H-4,7-methanoinden-5-yl]urea
Other names
  • Norea
  • 1,1-dimethyl-3-[(1S,2R,6R,7S,8R)-8-tricyclo[5.2.1.02,6]decanyl]urea
  • N,N-Dimethyl-N′-(octahydro-4,7-methano-1H-inden-5-yl)urea
  • l-5-(3a,4,5,6,7,7ahexahydro-4, 7 -methanoindanyl-3 ,3-dimethylurea
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.536 Edit this at Wikidata
EC Number
  • 242-406-2
UNII
  • InChI=1S/C13H22N2O/c1-15(2)13(16)14-12-7-8-6-11(12)10-5-3-4-9(8)10/h8-12H,3-7H2,1-2H3,(H,14,16)
    Key: YGLMVCVJLXREAK-UHFFFAOYSA-N
  • O=C(NC1CC2CC1C3CCCC23)N(C)C
Properties
C13H22N2O
Molar mass 222.332 g·mol−1
Density 1100 kg/m3[1]
Melting point 177 °C (351 °F; 450 K)[2]
194 mg/L[1]
Hazards
GHS labelling:[3]
GHS07: Exclamation mark
Warning
H302, H311
P264, P280, P312, P321, P361+P364, P501
Lethal dose or concentration (LD, LC):
  • 2000 mg/kg (rat, oral)
  • 723 mg/kg (rabbit, dermal)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Noruron (or norea) is a preëmergent urea herbicide active ingredient. It is considered obsolete, but may still be used. Introduced in the US in 1962, was used to control grass weeds and broadleaf weeds on crops including broomcorn, cotton, potatoes, sugarcane, spinach, soybeans and sorghum.[1][4]

Noruron is not approved for use in the EU.[5]

Chemistry

Noruron is stereochemically racemic, with 5 stereocenters.[6] It is a chiral molecule, and the technical grade stuff is mixed from two racemates.[7]

Application

Noruron is applied at 0.75 to 4 kg/ha of active ingredient, typically supplied as wettable powder or granules.[4]

Performance

Norea (in conifer seedbeds in Connecticut) provided fair to excellent weed control for two months, at 1.5 to 2 lbs/ac (1.68 to 2.24 kg/Ha), with injury to pine and spruce seedlings in most tests, though at 4 lbs/ac it injured white pine. Norea's control was comparable to simazine but shorter-lasting.[8]

A 1960s trial found noruron promising for growing dioscorea crops (such as yams), as of the tested herbicides it showed the most control without causing crop-injury.[9]

Products

It has been sold under the tradename "Herban",[1] a 76% norea wettable powder.[10] "Daban-1", "Maban-2" were liquid formulations containing 1 lb per gallon Herban. Maban was registered in 1967 and discontinued in 1989.[11][12] Herban was trademarked in 1963, renewed in 1983, but expired in 2004.[13]

Maban was registered for use on cotton, drainage ditch banks, fencerows, noncrop areas, rights-of-way, and storage yards.[12]

References

  1. ^ a b c d Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
  2. ^ "CAS Common Chemistry". commonchemistry.cas.org.
  3. ^ a b "SAFETY DATA SHEET" (PDF). LGC. 19 October 2022. Retrieved 21 May 2025.
  4. ^ a b "Noruron". Grainews. Retrieved 21 May 2025.
  5. ^ "EU Pesticides Database". ec.europa.eu.
  6. ^ "GSRS". gsrs.ncats.nih.gov.
  7. ^ "Noruron Solution". ESSLAB. Retrieved 21 May 2025.
  8. ^ Ahrens, J. F.; Merril, C. G.; Cubanski, M. (September 1976). "Herbicides for Conifer Seedbeds" (PDF). The Connecticut Agricultural Experiment Station (Bulletin 766). New Haven. Retrieved 13 June 2025.
  9. ^ Gaskins, M. H.; Delpin, H. (1973). "Weed Control in New Plantings of Steroid-Producing Dioscorea Species". Weed Science. 21 (3): 263–265. ISSN 0043-1745.
  10. ^ Williams, H.h. (1974). "Effects of certain preemergence herbicides on Diochondra SPP". Proceedings of the Second International Turfgrass Research Conference. pp. 410–417. doi:10.2135/1974.proc2ndintlturfgrass.c60. ISBN 978-0-89118-573-4.
  11. ^ "U.S. EPA, Pesticide Product Label, MABAN - 2, 05/24/1967" (PDF). Retrieved 13 June 2025.
  12. ^ a b "Maban - 2 pesticide information". www.pomerix.com. Retrieved 13 June 2025.
  13. ^ "HERBAN Trademark - Registration Number 0759031 - Serial Number 72164244 :: Justia Trademarks". trademark.justia.com. Retrieved 13 June 2025.
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