{{Short description |Herbicide active ingredient}} {{Chembox | Name = | ImageFile = Fluchloralin pic.svg | ImageSize = 120px | OtherNames = N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine | IUPACName = N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)aniline | SystematicName = |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 33245-39-5 | EC_number = 251-426-0 | ChEBI = 81919 | ChEMBL = 1256704 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 33448 | KEGG = C18730 | PubChem = 36392 | UNII = 98UIF19AH9 | StdInChI=1S/C12H13ClF3N3O4/c1-2-4-17(5-3-13)11-9(18(20)21)6-8(12(14,15)16)7-10(11)19(22)23/h6-7H,2-5H2,1H3 | StdInChIKey = MNFMIVVPXOGUMX-UHFFFAOYSA-N | SMILES = CCCN(CCCl)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-] }} | Section2 = {{Chembox Properties | C=12|H=13|Cl=1|N=3|O=4|F=3 | Appearance = Yellow crystalline solid<ref name = "database"/> | Density = | MeltingPtC = 42 | MeltingPt_notes = <ref name = "database"/> | BoilingPtC = | BoilingPt_notes = | Solubility = 0.9 mg/L<ref name = "database"/> | VaporPressure = 4.0 mPa<ref name = "database"/> }} | Section3 = {{Chembox Hazards | MainHazards = Skin and eye irritant<ref name = "database"/> | FlashPtC = 30 | FlashPt_notes = <ref name = "database"/> | GHS_ref= | GHSPictograms = | GHSSignalWord = | HPhrases = | PPhrases = | AutoignitionPt = | LD50 = {{ubl|1550 mg/kg (rat, oral)|10000 mg/kg (dermal, rat)<ref name = "database"/>}} | LC50 = {{ubl||}} }} }}
'''Fluchloralin''' is a preëmergent dinitroaniline herbicide, introduced in 1972, and used to control broad-leaved weeds and annual grasses. It is used in India.<ref name = "database">Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242</ref><ref name = "bulletin 22">Choudhury PP, Singh R, Ghosh D and Sharma AR. 2016. Herbicide Use in Indian Agriculture. ICAR - Directorate of Weed Research, Jabalpur, Madhya Pradesh, 110 p. https://dwr.icar.gov.in/Downloads/Information_Bulletin/Information%20Bulletin%20No%20-%2022%20-%20Herbicide%20Use%20in%20Indian%20Agriculture.pdf</ref> In other countries, it might be considered obsolete.<ref name = "database"/> 71 tonnes of fluchloralin was sold in India in fiscal year 2009–2010.<ref name = "bulletin 22"/> Basalin was registered in the US in 1975 as "Basalin", whose registration expired in 1986.<ref name = "pomerix"/>
The USGS estimates fluchloralin use in the US to be 50,000 to 250,000 pounds in 1994, (22 to 112 tonnes) with no usage after 1995.<ref>{{cite web |title=2007 Pesticide Use Maps |url=https://water.usgs.gov/nawqa/pnsp/usage/maps/show_map.php?year=2007&map=FLUCHLORALIN&hilo=L |website=water.usgs.gov |publisher=USGS |access-date=15 August 2025}}</ref>
== Mechanism == Fluchloralin's resistance class is D (Australia), K1 (global) or 3 (numeric); its mode of action is inhibition of microtubule formation.<ref name = "database"/> Since it is incorporated into the top 1-2 inches of soil,<ref name="pomerix">{{cite web |title=Basalin Emulsifiable Concentrate Preplant Incorporated Herbicide pesticide information |url=https://www.pomerix.com/pesticides/basalin-emulsifiable-concentrate-preplant-incorporated-herbicide |website=www.pomerix.com |access-date=26 June 2025}}</ref> germinating weeds grow up and contact fluchloralin.<ref name="i dont trust this source but im pretty sure this is right anyway">{{cite web |title=Exploring the Effects and Benefits of Basalin Herbicide on Agricultural Productivity and Weed Control |url=https://www.cnagrochem.com/ar/news/exploring-the-effects-and-benefits-of-basalin-herbicide-on-agricultural-productivity-and-weed-control.html |website=www.cnagrochem.com |access-date=26 June 2025}}</ref>
Fluchloralin seems to affect cells during metaphase most. Applied to sunflower and flax, the germination rate and the plants' cells' mitotic index decreased, and the rate of chromosomal abnormality increased.<ref name = "i1994"/>
==Environmental behaviour== It can persist for 3 to 6 months in soil,<ref name = "bulletin 22"/> with a half-life of 12 to 46 days, variable with temperature and soil type.<ref name = "zebra"/> In water, photolysis degrades it rapidly, with a half life of half an hour.<ref name = "database"/> The 24 hour LC<sub>50</sub> in fish is 0.027 mg/L.<ref name = "sinha"/>
Zebrafish exposed to fluchloralin during embryogenesis showed inhibited neurogenesis in the nervous system, reduced length and dysfunction of the heart, liver and pancreas.<ref name = "zebra">{{cite journal |last1=Hong |first1=Taeyeon |last2=Park |first2=Hahyun |last3=An |first3=Garam |last4=Park |first4=Junho |last5=Song |first5=Gwonhwa |last6=Lim |first6=Whasun |title=Fluchloralin induces developmental toxicity in heart, liver, and nervous system during early zebrafish embryogenesis |journal=Comparative Biochemistry and Physiology Part C: Toxicology & Pharmacology |date=September 2023 |volume=271 |article-number=109679 |doi=10.1016/j.cbpc.2023.109679 |pmid=37290698 }}</ref> At high concentrations, of 20 mg/L and above, fluchloralin has a genotoxic effect on human lymphocytes.<ref name = "sinha">{{cite journal |last1=Panneerselvam |first1=Natarajan |last2=Sinha |first2=Sapna |last3=Shanmugam |first3=Govindaswamy |title=Genotoxicity of the herbicide fluchloralin on human lymphocytes in vitro: chromosomal aberration and micronucleus tests |journal=Mutation Research/Genetic Toxicology |date=August 1995 |volume=344 |issue=1–2 |pages=69–72 |doi=10.1016/0165-1218(95)90040-3 |pmid=7565895 }}</ref>
Fluchloralin is cometabolised by microörganisms in sewage, as are nitrofen, trifluralin and profluralin; i.e. enzymes from other active metabolic processes also break up these chemicals. Over 88 days, fluchloralin levels reduced by 91% under aerobic conditions. Discontinuous anaerobic conditions made little difference, with a 95% reduction. Fluchloralin had 12 identified metabolites.<ref>{{cite journal |last1=Jacobson |first1=Stuart N. |last2=O'Mara |first2=Nancy L. |last3=Alexander |first3=Martin |title=Evidence for Cometabolism in Sewage |journal=Applied and Environmental Microbiology |date=November 1980 |volume=40 |issue=5 |pages=917–921 |doi=10.1128/aem.40.5.917-921.1980|pmid=16345657 |pmc=291690 |bibcode=1980ApEnM..40..917J }}</ref>
==Usage== It has been sold as a 45% (480 g/L) emulsifiable concentrate (EC), and applied at rates of 0.75 to 1.5 kg/ha of active ingredient.<ref name = "bulletin 22"/><ref name = "i1994">Sadhana Saxena & Sheela Srivastava (1994) Cytotoxicity of the herbicide basalin (fluchloralin) in helianthus and linum, Journal of Environmental Science & Health Part B, 29:6, 1137-1152, DOI: 10.1080/03601239409372920</ref>
Fluchloralin can be applied up to six or eight weeks before sowing, but must be incorporated into soil (one or two inches deep) within a day of application. If treated soil is then removed, or furrowed too deeply, untreated soil can be exposed and allow weed growth.<ref name="basalin label">{{cite web |title=U.S. EPA, Pesticide Product Label, BASALIN EMULSIFIABLE CONCENTRATE PREPLANT INCORPORATED HERBICIDE, 11/30/1983 |url=https://www3.epa.gov/pesticides/chem_search/ppls/007969-00046-19831130.pdf |access-date=26 June 2025 |date=1 March 1983}}</ref>
Fluchloralin has been used on peas, beans, cotton, okra, sunflowers, soybean and peanuts.<ref name = "database"/>
=== List of susceptible weeds === It is effective on grasses and broadleaves. These grasses: smooth crabgrass (Digitaria ischaemum), large crabgrass (Digitaria sanguinalis), barnyardgrass (watergrass), giant foxtail (Setaria viridis), green foxtail (Setaria lutescens), yellow foxtail (Setaria Indica), Japanese millet (Echinochloa crus-galli var. frumentacea), junglerice (Echinochloa colonum), fall panicum (Panicum dichotomiflorum), broadleaf signalgrass (Brachiaria platyphylla), seedling johnsongrass (Sorghum halepense), Texas panicum (buffalograss, Coloradograss, Panicum texanum), shattercane (Sorghum bicolor), rhizome johnsongrass and red rice (Oryza sativa). It is effective against the broadleaf weeds: various species of pigweed (Amaranthus), lambsquarters (Chenopodium album), common purslane (Portulaca oleracea), Florida pursley (Richardia scabra) and carpetweed (Mollugo verticillata). Morningglory (Ipomoea) is also moderately susceptible.<ref name="basalin label"/>
==Tradenames== It has been sold as ''Basalin'' (BASF), ''Dhanulin'' (Dhanuka Agritech), ''Nagflur'' (Multiplex), ''Anulin'' (Anu), ''Vicolin'' (Ghujarat Krishi), ''Herbilin'' (Herbicide India) and ''Flight'' (Devidayal).<ref name = "bulletin 22"/>
==References== {{reflist}}
==Links== *{{PPDB|1281}}
{{Aniline Herbicides}} {{Herbicides}}
Category:Herbicides Category:Anilines Category:Nitrobenzene derivatives Category:Trifluoromethyl compounds Category:Chloroethyl compounds Category:Group 3 herbicides Category:Preemergent herbicides Category:Dinitroaniline herbicides