fluchloralin

{{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

| Density =

| MeltingPtC = 42

| MeltingPt_notes =

| BoilingPtC =

| BoilingPt_notes =

| Solubility = 0.9 mg/L

| VaporPressure = 4.0 mPa

}}

| Section3 = {{Chembox Hazards

| MainHazards = Skin and eye irritant

| FlashPtC = 30

| FlashPt_notes =

| GHS_ref=

| GHSPictograms =

| GHSSignalWord =

| HPhrases =

| PPhrases =

| AutoignitionPt =

| LD50 = {{ubl|1550 mg/kg (rat, oral)|10000 mg/kg (dermal, rat)}}

| LC50 = {{ubl||}}

}}

Fluchloralin is a pre-emergent dinitroaniline herbicide, introduced in 1972, and used to control broad-leaved weeds and annual grasses. It is used in India.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: 10.1080/10807039.2015.1133242Choudhury 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 In other countries, it might be considered obsolete. 71 tonnes of fluchloralin was sold in India in fiscal year 2009–2010. Basalin was registered in the US in 1975 as "Basalin", whose registration expired in 1986.

Mechanism

Fluchloralin's resistance class is D (Australia), K1 (global) or 3 (numeric); its mode of action is inhibition of microtubule formation. Since it is incorporated into the top 1-2 inches of soil,{{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}} germinating weeds grow up and contact fluchloralin.{{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}}

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.

Environmental behaviour

It can persist for 3 to 6 months in soil, with a half-life of 12 to 46 days, variable with temperature and soil type. In water, photolysis degrades it rapidly, with a half life of half an hour. The 24 hour LC₅₀ in fish is 0.027 mg/L.

Zebrafish exposed to fluchloralin during embryogenesis showed inhibited neurogenesis in the nervous system, reduced length and dysfunction of the heart, liver and pancreas.{{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 |pages=109679 |doi=10.1016/j.cbpc.2023.109679}} At high concentrations, of 20 mg/L and above, fluchloralin has a genotoxic effect on human lymphocytes.{{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}}

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.{{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|pmc=291690 }}

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.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

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.{{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}}

Fluchloralin has been used on peas, beans, cotton, okra, sunflowers, soybean and peanuts.

= 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.

Tradenames

It has been sold as Basalin (BASF), Dhanulin (Dhanuka Agritech), Nagflur (Multiplex), Anulin (Anu), Vicolin (Ghujarat Krishi), Herbilin (Herbicide India) and Flight (Devidayal).