Fluchloralin

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Fluchloralin
Names
IUPAC name
N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)aniline
Other names
N-(2-chloroethyl)-2,6-dinitro-N-propyl-4-(trifluoromethyl)benzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.736 Edit this at Wikidata
EC Number
  • 251-426-0
KEGG
UNII
  • InChI=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
    Key: MNFMIVVPXOGUMX-UHFFFAOYSA-N
  • CCCN(CCCl)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]
Properties
C12H13ClF3N3O4
Molar mass 355.70 g·mol−1
Appearance Yellow crystalline solid[1]
Melting point 42 °C (108 °F; 315 K) [1]
0.9 mg/L[1]
Vapor pressure 4.0 mPa[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Skin and eye irritant[1]
Flash point 30 °C (86 °F; 303 K) [1]
Lethal dose or concentration (LD, LC):
  • 1550 mg/kg (rat, oral)
  • 10000 mg/kg (dermal, rat)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1][2] In other countries, it might be considered obsolete.[1] 71 tonnes of fluchloralin was sold in India in fiscal year 2009–2010.[2] Basalin was registered in the US in 1975 as "Basalin", whose registration expired in 1986.[3]

Mechanism

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Fluchloralin's resistance class is D (Australia), K1 (global) or 3 (numeric); its mode of action is inhibition of microtubule formation.[1] Since it is incorporated into the top 1-2 inches of soil,[3] germinating weeds grow up and contact fluchloralin.[4]

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.[5]

Environmental behaviour

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It can persist for 3 to 6 months in soil,[2] with a half-life of 76 days. In water, photolysis degrades it rapidly, with a half life of half an hour.[1]

Usage

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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.[2][5]

Fluchloralin can be planted 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.[6]

Fluchloralin has been used on peas, beans, cotton, okra, sunflowers, soybean and peanuts.[1]

List of susceptible weeds

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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.[6]

Tradenames

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It has been sold as Basalin (BASF), Dhanulin (Dhanuka Agritech), Nagflur (Multiplex), Anulin (Anu), Vicolin (Ghujarat Krishi), Herbilin (Herbicide India) and Flight (Devidayal).[2]

References

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  1. ^ a b c d e f g h i j k l 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
  2. ^ a b c d e 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
  3. ^ a b "Basalin Emulsifiable Concentrate Preplant Incorporated Herbicide pesticide information". www.pomerix.com. Retrieved 26 June 2025.
  4. ^ "Exploring the Effects and Benefits of Basalin Herbicide on Agricultural Productivity and Weed Control". www.cnagrochem.com. Retrieved 26 June 2025.
  5. ^ a b 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
  6. ^ a b "U.S. EPA, Pesticide Product Label, BASALIN EMULSIFIABLE CONCENTRATE PREPLANT INCORPORATED HERBICIDE, 11/30/1983" (PDF). 1 March 1983. Retrieved 26 June 2025.
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