Butralin

Last updated
Butralin
Butralin simplified.png
Names
Preferred IUPAC name
rac-N-[-butan-2-yl]-4-tert-butyl-2,6-dinitroaniline
Other names
  • amexine
  • dibutaline
  • (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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 251-607-4
KEGG
PubChem CID
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
AppearanceYellow/orange powder [1]
Density 1.063 [2]
Melting point 59 [2]  °C (138 °F; 332 K)
Vapor pressure 0.000013 mmHg
Hazards
GHS labelling: [1] [3]
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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)
Lethal dose or concentration (LD, LC):
  • 1100 mg/kg (rat, oral) [2]
  • >2000 mg/kg (rat, dermal) [2]
  • 2250 mg/kg (bobwhite quail, oral) [2]
  • 0.37 mg/L (rainbow trout) [2]
  • 0.12 mg/L (algae)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Butralin is a preemergent herbicide used to control suckers on tobacco in the United States, [4] [5] Australia, [6] Mozambique and, for food crops also, China. [7] It is a dinitroaniline, first registered in the US in 1976. [8] It was used in the EU until a ban in 2009 due to its ecotoxicity. [7] [9]

Contents

Mode of action and effects

Butralin 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 depolymerization.

In ryegrass meristems, butralin-treated roots show reduced elongation, but greater diameter. The cells' rate of mitosis lowers 36% after one hour, and they develop multiple nuclei. Butralin's effect is more similar to carbamate herbicides such as chlorpropham rather than other dinitroanilines. [10]

Usage

Butralin is sold in Mozambique as "Tobralin 36% EC", made in South Africa. Users are instructed to pour 10 mL on each tobacco plant by hand, and not to unclog nozzles with their mouths. [11] [12]

In China, over 100 tons per year are used, as of 2022, on garlic, soybean, tomato, rice, peanut, pepper, cotton, eggplant, and watermelon. The maximum residue limit is 0.02 to 0.1 mg/kg. [7] The growing Chinese market sells it in 36% or 48% emulsifiable concentrates, and in development as of 2012, a 41% wettable powder. The powder claims to be environmentally friendly, as it lacks the volatile organic molecules such as toluene and xylene used as solvent in EC formulations. [13] The powder is recommended to be applied at 2100 g/Ha (active ingredient). [14]

In Australia, butralin was registered in 1996. Butralin as an active ingredient is still registered, though no product containing it has been registered since 2008. [15] [16] [17] It may have been registered before 1990. [18]

American usage (by USGS estimates) has held roughly steady at about 40,000 pounds (18 t) per year (data from 1996 to 2018). [19]

Health

Butralin is of low acute toxicity. [6] There is no association with lung cancer. [9]

It is very toxic to Daphnia . [2]

In soil

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. [8] Butralin's major soil metabolite is 4-tert-butyl-2,6-dinitroaniline. [20] Other major metabolites see the loss of more or all of the carbons and hydrogen over the nitrogen, or loss of oxygen from the nitro groups. The principle residue in crops, however, is the parent butralin. [21]

References

  1. 1 2 Hertfordshire, University of. "Butralin (Ref: Amchem70-25)". sitem.herts.ac.uk.
  2. 1 2 3 4 5 6 7 "MSDS: TOBRALIN 36% EC" (PDF). ARYSTA LIFESCIENCE (PTY)LTD. July 2005. Retrieved 18 November 2024.
  3. ↑ "Butralin". pubchem.ncbi.nlm.nih.gov.
  4. ↑ "Butralin® Sucker Control Specimen Label".
  5. ↑ "Pesticide Product Label, NUFARM SAS TECHNICAL BUTRALIN,04/25/2019" (PDF). US EPA. April 25, 2019.
  6. 1 2 "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.
  7. 1 2 3 Chen, Zenglong; Kang, Shanshan; Ren, Xin; Cheng, Youpu; Li, Wei; Zhao, Lilin (May 2023). "Large-scale fate profiling of butralin between cultivated and processed garlics for multi-risk estimations". Science of the Total Environment. 873 162369. Bibcode:2023ScTEn.87362369C. doi:10.1016/j.scitotenv.2023.162369. PMID   36828059.
  8. 1 2 "Pesticides - Fact Sheet for Butralin" (PDF). EPA. May 1998.
  9. 1 2 Boulanger, Mathilde; Tual, Séverine; Lemarchand, Clémentine; Baldi, Isabelle; Clin, Bénédicte; Lebailly, Pierre (August 2017). "0441 Exposure to dinitroanilines and risk of lung cancer (Lc) by subtypes: Results from the agrican cohort". Occupational & Environmental Medicine. 74 (Suppl 1): A140.1. doi:10.1136/oemed-2017-104636.365.
  10. ↑ Elmore, C. L.; Bayer, D. E. (April 1992). "Mitotic and structural effects of nitralin and butralin on ryegrass ( Lolium perenne L.) root meristems". Weed Research. 32 (2): 77–86. Bibcode:1992WeedR..32...77E. doi:10.1111/j.1365-3180.1992.tb01864.x.
  11. ↑ "TOBRALIN 36% EC" (PDF). AgriFocus Limitada. Retrieved 18 November 2024.
  12. ↑ "UPL | Mozambique". www.upl-ltd.com.
  13. ↑ Li Zhao; Ji-Xing Zhao; Qian Cheng (October 2012). "Development of new environment-friendly pesticides formulation butralin". 2012 International Symposium on Geomatics for Integrated Water Resource Management. pp. 1–3. doi:10.1109/giwrm.2012.6349603. ISBN   978-1-4673-1282-0.
  14. ↑ Li Zhao; Qian Cheng; Ji-Xing Zhao (October 2012). "Applied research on butralin-new environmentally friendly formulation and analysis of its environmental and economic effects". 2012 International Symposium on Geomatics for Integrated Water Resource Management. pp. 1–4. doi:10.1109/giwrm.2012.6349604. ISBN   978-1-4673-1282-0.
  15. ↑ "APVMA PubCRIS: Nufarm Tobacco Sucker Control Agent 48894". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.
  16. ↑ "APVMA PubCRIS: TOBAGO TOBACCO SUCKER CONTROL AGENT 46862". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.
  17. ↑ "APVMA PubCRIS: BUTRALIN". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.
  18. ↑ "APVMA PubCRIS: Union Carbide Tobacco Sucker Control Agent". portal.apvma.gov.au. Australian Pesticides and Veterinary Medicines Authority. Retrieved 10 August 2025.
  19. ↑ "2019 Pesticide Use Maps -". water.usgs.gov. USGS.
  20. ↑ "ECM - Butralin & Degradate in Soil - MRID 43749801" (PDF). EPA.
  21. ↑ "Reasoned opinion on the review of the existing maximum residue levels (MRLs) for butralin according to Article 12 of Regulation (EC) No 396/2005: Review of the existing MRLs for butralin". EFSA Journal. 10 (4): 2651. April 2012. doi: 10.2903/j.efsa.2012.2651 .
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