View source for Butralin

{{Short description|Weed control herbicide}}
{{Chembox
| Reference =
| ImageFile =
[[File:Butralin simplified.png|frameless]]
| PIN =	''rac''-''N''-[-butan-2-yl]-4-tert-butyl-2,6-dinitroaniline
| OtherNames = 	{{ubl|amexine|dibutaline|(''RS'')-''N''-''sec''-Butyl-4-''tert''-butyl-2,6-dinitroaniline|4-(1,1-dimethylethyl)-''N''-(1-Methylpropyl)-2,6-dinitrobenzenamine}}
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 33600
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C18582
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 81847
| StdInChI=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
| StdInChIKey = 	SPNQRCTZKIBOAX-UHFFFAOYSA-N
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1256669
| EC_number = 251-607-4
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 33629-47-9
| PubChem = 36565
| UNII = 5CZK3K1YPB
| UNNumber =
| SMILES = CCC(C)NC1=C(C=C(C=C1[N+](=O)[O-])C(C)(C)C)[N+](=O)[O-]
}}
|Section2={{Chembox Properties
| C=14|H=21|N=3|O=4
| Appearance = Yellow/orange powder<ref NAME = "database">{{cite web |last1=Hertfordshire |first1=University of |title=Butralin (Ref: Amchem70-25) |url=https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/104.htm |website=sitem.herts.ac.uk}}</ref>
| Odour =
| Density = 1.063<ref name="Tolban SDS">{{cite web |title=MSDS : TOBRALIN 36% EC |url=https://mz.uplcorp.com/download_links/YRY2fkm1b9uoQey4Qc50DIe57vcry7ot9hmAjqGW.pdf |publisher=ARYSTA LIFESCIENCE (PTY)LTD |access-date=18 November 2024 |date=July 2005}}</ref>
| MeltingPtC = 59<ref name = "Tolban SDS"/>
| MeltingPt_notes =
| BoilingPtF =
| BoilingPt_notes =
| Solubility =
| Solvent1 = acetone
| Solubility1 =
| VaporPressure = 0.000013 mmHg
}}
|Section3={{Chembox Hazards
| MainHazards =
| HPhrases       = {{HPhrases|302|319|341|361|410}}
| GHS_ref=<ref name = "database"/><ref>{{cite web |title=Butralin |url=https://pubchem.ncbi.nlm.nih.gov/compound/36565#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| PPhrases = {{P-phrases|203|264|264+265|270|273|280|301+317|305+351+338|318|330|337+317|391|405|501}}
| LD50 = {{ubl|1100 mg/kg (rat, oral)<ref name = "Tolban SDS"/>|>2000 mg/kg (rat, dermal)<ref name = "Tolban SDS"/>|2250 mg/kg (bobwhite quail, oral)<ref name = "Tolban SDS"/>}}
| LC50 = {{ubl|0.37 mg/L (rainbow trout)<ref name = "Tolban SDS"/>|0.12 mg/L (algae)}}
| FlashPtC = 36
| AutoignitionPtF =
}}
}}
'''Butralin''' is a [[preemergent herbicide]] used to control suckers on [[tobacco]] in the [[United States]],<ref>{{cite web |title=Butralin® Sucker Control Specimen Label |url=https://www.upl-ltd.com/us/product-details/butralin-sucker-control}}</ref><ref>{{cite web |title=Pesticide Product Label, NUFARM SAS TECHNICAL BUTRALIN,04/25/2019 |url=https://www3.epa.gov/pesticides/chem_search/ppls/033688-00002-20190425.pdf |publisher=US EPA |date=April 25, 2019}}</ref> Australia,<ref name = "toxno"/> Mozambique and, for food crops also, China.<ref name = "the chinese"/> It is a [[dinitroaniline]], first registered in the US in 1976.<ref name="epa 1998">{{cite web |title=Pesticides - Fact Sheet for Butralin |url=https://www3.epa.gov/pesticides/chem_search/reg_actions/reregistration/fs_PC-106501_19-May-98.pdf |publisher=EPA |date=May 1998}}</ref> It was used in the EU until a ban in 2009 due to its [[exotoxicity]].<ref name="the chinese">{{cite journal |last1=Chen |first1=Zenglong |last2=Kang |first2=Shanshan |last3=Ren |first3=Xin |last4=Cheng |first4=Youpu |last5=Li |first5=Wei |last6=Zhao |first6=Lilin |title=Large-scale fate profiling of butralin between cultivated and processed garlics for multi-risk estimations |journal=Science of the Total Environment |date=May 2023 |volume=873 |pages=162369 |doi=10.1016/j.scitotenv.2023.162369|pmid=36828059 }}</ref><ref name="baguette cancer">{{cite journal |last1=Boulanger |first1=Mathilde |last2=Tual |first2=Séverine |last3=Lemarchand |first3=Clémentine |last4=Baldi |first4=Isabelle |last5=Clin |first5=Bénédicte |last6=Lebailly |first6=Pierre |journal=Occupational & Environmental Medicine |title=0441 Exposure to dinitroanilines and risk of lung cancer (Lc) by subtypes: Results from the agrican cohort |date=August 2017 |volume=74 |issue=Suppl 1|page=A140.1  |doi=10.1136/oemed-2017-104636.365}}</ref>
== Mode of action and effects ==
Butralin works by the HRAC mode of action Group D / K1 / 3, (Australian, Global, Numeric respectively), which involves [[Trifluralin#Mechanism_and_effects|inhibition of microtubule formation]], by binding to tubulin, halting growth, and causing [[depolymerization]].
In [[ryegrass]] [[meristem]]s, butralin-treated roots show reduced elongation, but greater diameter. The cells' rate of mitosis lowers 36% after one hour, and they develop multiple [[Cell nucleus|nuclei]]. Butralin's effect is more similar to [[carbamate]] herbicides such as [[chlorpropham]] rather than other dinitroanilines.<ref>{{cite journal |last1=Elmore |first1=C. L. |last2=Bayer |first2=D. E. |title=Mitotic and structural effects of nitralin and butralin on ryegrass ( Lolium perenne L.) root meristems |journal=Weed Research |date=April 1992 |volume=32 |issue=2 |pages=77–86 |doi=10.1111/j.1365-3180.1992.tb01864.x}}</ref>
== Usage ==
Butralin is sold in [[Mozambique]] as "Tobralin 36% [[emulsifiable concentrate|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.<ref>{{cite web |title=TOBRALIN 36% EC |url=https://mz.uplcorp.com/download_links/lJoyx37DIqFxswyZ6tPKiDARMwDcPdiXQJ94Ht04.pdf |publisher=AgriFocus Limitada |access-date=18 November 2024 }}</ref><ref>{{cite web |title=UPL {{!}} Mozambique |url=https://www.upl-ltd.com/mz/Detalhes-do-Produto/tobralin-36-9-ec |website=www.upl-ltd.com}}</ref>
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.<ref name="the chinese" /> The growing Chinese market sells it in 36% or 48% [[emulsifiable concentrate]]s, 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.<ref>{{cite journal |title=Development of new environment-friendly pesticides formulation butralin |journal=2012 International Symposium on Geomatics for Integrated Water Resource Management |date=October 2012 |pages=1–3 |doi=10.1109/giwrm.2012.6349603}}</ref> The powder is recommended to be applied at 2100 g/Ha (active ingredient).<ref>{{cite journal |title=Applied research on butralin-new environmentally friendly formulation and analysis of its environmental and economic effects |journal=2012 International Symposium on Geomatics for Integrated Water Resource Management |date=October 2012 |pages=1–4 |doi=10.1109/giwrm.2012.6349604}}</ref>
== Health ==
Butralin is of low acute toxicity.<ref name = "toxno">{{cite web |title=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 |url=https://www.toxno.com.au/toxins/substance_id_9577.html |website=www.toxno.com.au}}</ref> There is no association with lung [[cancer]].<ref name = "baguette cancer"/>
It is very toxic to ''[[Daphnia]]''.<ref name = "Tolban SDS"/>
== 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.<ref name = "epa 1998"/> Butralin's major soil metabolite is 4-''tert''-butyl-2,6-dinitroaniline.<ref>{{cite web |title=ECM - Butralin & Degradate in Soil - MRID 43749801 |url=https://www.epa.gov/sites/default/files/2014-12/documents/43749801-butralin-ecm-soil.pdf |publisher=EPA}}</ref> 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.<ref>{{cite journal |title=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 |journal=EFSA Journal |date=April 2012 |volume=10 |issue=4 |pages=2651 |doi=10.2903/j.efsa.2012.2651}}</ref>
== References ==
{{reflist}}
== Links ==
* {{PPDB|104}}
{{Herbicides}}
[[Category:Preemergent herbicides]]
[[Category:Nitrotoluene derivatives]]
[[Category:Anilines]]
[[Category:Herbicides]]
[[Category:Products introduced in 1976]]
[[Category:Sec-Butyl compounds]]
[[Category:Tert-butyl compounds]]