Butralin is a herbicide, used in the United States to control suckers on tobacco,[3] and approved in Australia.[4] It is a preemergent dinitroaniline, first registered in the US in 1976.[5]

Butralin
Names
Preferred IUPAC name
rac-N-[-butan-2-yl]-4-tert-butyl-2,6-dinitroaniline
Other names
  • (RS)-N-sec-Butyl-4-tert-butyl-2,6-dinitroaniline
  • 4-(1,1-dimethylethyl)-N-(1-Methylpropyl)-2,6-dinitrobenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.902 Edit this at Wikidata
EC Number
  • 251-607-4
KEGG
UNII
  • InChI=1S/C14H21N3O4/c1-6-9(2)15-13-11(16(18)19)7-10(14(3,4)5)8-12(13)17(20)21/h7-9,15H,6H2,1-5H3
    Key: SPNQRCTZKIBOAX-UHFFFAOYSA-N
  • CCC(C)NC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-]
Properties
C14H21N3O4
Molar mass 295.339 g·mol−1
Appearance Yellow/orange powder[1]
Density 1.06
Melting point 61 °C (142 °F; 334 K)
Vapor pressure 0.000013 mmHg
Hazards
GHS labelling:[1][2]
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H319, H341, H361, H410
P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P391, P405, P501
Flash point 36 °C (97 °F; 309 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

It works by the HRAC mode of action Group D / K1 / 3, (Australian, Global, Numeric respectively), which involves inhibition of microtubule formation, by binding to tubulin, halting growth and causing depolymerisation.

Butralin is of low acute toxicity.[4]

Butralin is likely to be moderately persistent to persistent and relatively immobile in terrestrial environments. Butralin is stable to abiotic hydrolysis and photodegradation on soil. Its characteristics are unlike those of chemicals that leach to groundwater.[5]

References

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  1. ^ a b Hertfordshire, University of. "Butralin (Ref: Amchem70-25)". sitem.herts.ac.uk.
  2. ^ "Butralin". pubchem.ncbi.nlm.nih.gov.
  3. ^ "Butralin® Sucker Control Specimen Label".
  4. ^ a b "Butralin • Potentially found in food, soil, water, dust, compost, hair, cosmetics, a medication, animals & pets, home or workplace • its health effects • should I avoid it • testing with Toxtest in Australia • substance_id_9577 • CASRN: 33629-47-9". www.toxno.com.au.
  5. ^ a b "Pesticides - Fact Sheet for Butralin" (PDF). EPA. May 1998.
edit
  • Butralin in the Pesticide Properties DataBase (PPDB)