Noruron

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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Legal Status

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

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