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Butralin

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Butralin
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 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 1.063[2]
Melting point 59[2] °C (138 °F; 332 K)
Vapor pressure 0.000013 mmHg
Hazards
GHS labelling:[1][3]
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)
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 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 preëmergent dinitroaniline, first registered in the US in 1976.[8] It was used in the EU, until a ban for exotoxicity in 2009.[7][9]

Mode of Action and Effects

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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 depolymerisation.

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 like chlorpropham rather than other dinitroanilines.[10]

Usage

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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 mouthes.[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 like toluene and xylene used as solvent in EC formulations.[13] The powder is recommended to be applied at 2100 g/Ha (active ingredient).[14]

Health

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

It is very toxic to daphnia.[2]

In Soil

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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,[15] which has lost all but two carbon atoms over the nitrogen. 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.[16]

References

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  1. ^ a b Hertfordshire, University of. "Butralin (Ref: Amchem70-25)". sitem.herts.ac.uk.
  2. ^ a b c d e f g "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. ^ 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.
  7. ^ a b c 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. doi:10.1016/j.scitotenv.2023.162369. PMID 36828059.
  8. ^ a b "Pesticides - Fact Sheet for Butralin" (PDF). EPA. May 1998.
  9. ^ a b 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. 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. ^ "Development of new environment-friendly pesticides formulation butralin". 2012 International Symposium on Geomatics for Integrated Water Resource Management: 1–3. October 2012. doi:10.1109/giwrm.2012.6349603.
  14. ^ "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: 1–4. October 2012. doi:10.1109/giwrm.2012.6349604.
  15. ^ "ECM - Butralin & Degradate in Soil - MRID 43749801" (PDF). EPA.
  16. ^ "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.
[edit]
  • Butralin in the Pesticide Properties DataBase (PPDB)
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