Anilofos

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Anilofos
Anilofos 200.svg
Names
IUPAC name
S-4-chloro-N-isopropylcarbaniloylmethyl-O, O-dimethylphosphorodithioate [1]
Other names
Anilophos, Arozin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.058.851 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 264-756-5
KEGG
PubChem CID
UNII
  • InChI=1S/C13H19ClNO3PS2/c1-10(2)15(12-7-5-11(14)6-8-12)13(16)9-21-19(20,17-3)18-4/h5-8,10H,9H2,1-4H3 Yes check.svgY
    Key: NXQDBZGWYSEGFL-UHFFFAOYSA-N Yes check.svgY
  • CC(C)N(C1=CC=C(C=C1)Cl)C(=O)CSP(=S)(OC)OC
Properties
C13H19ClNO3PS2
Molar mass 367.84 g·mol−1
Appearancewhite-to-brown solid [2] [3] [4]
Density 1.322 t/m3 [5]
Melting point 51 °C (124 °F; 324 K) [5]
Boiling point 444 °C (831 °F; 717 K) [5]
9.4 mg/L [4]
Solubility in acetone >700 g/L [3]
Solubility in chloroform >700 g/L [3]
Solubility in toluene >700 g/L [3]
Vapor pressure 2.2 mPa [4]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Acute oral toxicity, irritation
GHS labelling: [6]
GHS-pictogram-exclam.svg
Warning
H302
P264, P270, P301+P317, P330, P501 [7]
Flash point 221°C, 430°F [5]
Lethal dose or concentration (LD, LC):
  • 472 mg/kg (rat, oral)
  • >2000 mg/kg (rabbit, dermal) [2]
  • 26 g/m3 (rat, inhalation, 4 hr)
  • 2.8 mg/L (trout, 96 hr) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anilofos, or anilophos, is an organophosphorus, anilide herbicide, used as a pre- or post-emergent selective herbicide to control annual grassy weeds and sedges in transplanted rice. It is used in India. [1] It was brought to market circa 1980. [4]

Contents

Usage

Anilophos's herbicide resistance classification is group K (Australia), K3 (global), or 15 (numeric), [4] which is the inhibition of very long chain fatty acid synthesis. It is absorbed though roots and to some extent through newly emerging shoots and young leaves. It acts on meristematic tissue to affect cell division and elongation, [8] producing discolouration, stunted growth and death. [3]

Anilofos is not approved in the European Union under Regulation No. 1107/2009. [9] It controls Indian goosegrass, barnyard grass, flatsedge, yellow nutsedge and cockspur. It is used on rice, [4] paddy and soybean. [8]

Formulations of anilophos have been sold under the tradenames Arrozin, Ricozin, Aniloguard, Shoot and Anilo-Tox, which are usually sold as emulsifiable concentrates, granules or dispersible powders. [4] [8] In India, they are applied at 300 to 350 grams per hectare active ingredient. Anilofos is adsorbed initially on the plant's surface and slowly by intracellular uptake. [10]

Forumations in India are sold as 18% or 30% emulsifiable concentrates. 631 tonnes (1,391,000 lb) was used in 2007, 2.6% of India's total herbicide usage. [11]

Properties

Anilophos is lipophilic. Organophosphorus lipophilics interact strongly with cell membrane phospholipid, such as chlorpyrifos, an insecticide with this site of action. [1]

Anilofos is chemically stable under standard conditions, but under intense heating may form an explodable mixture with air. [2] It has low volatility. [4] Anilofos is soluble in acetone, chloroform and toluene, to over 700 g/L, and in benzene, dichloromethane, ethanol, ethyl acetate to 53 g/L, hexane to 7.4 g/L. [3] It is insoluble in water. [2]

Anilofos is a thiono organophosphate. [1]

Environmental behaviour

Anilofos is moderately persistent in soil, with a half-life of about 38 days, [4] although in flooded soil it dissipates faster, in 5 to 25 days. [10] It doesn't bioaccumulate in soil and shows no tendency for groundwater leaching. The water half-life is also short. [3] It is not toxic to birds, with an LD50 over 3360 mg/kg, though the LD50 for bees via contact is 5.9μg, moderately toxic. [4]

Safety

There is evidence that anilofos is a neurotoxin, that it inhibits acetyl cholinesterase and that it irritates the skin and respiratory tract. [4]

References

  1. 1 2 3 4 Hazarika, Archana; Sarkar, S.N. (August 2001). "Effect of isoproturon pretreatment on the biochemical toxicodynamics of anilofos in male rats". Toxicology. 165 (2–3): 87–95. Bibcode:2001Toxgy.165...87H. doi:10.1016/S0300-483X(01)00411-5. PMID   11522367.
  2. 1 2 3 4 5 "Anilofos Safety Datasheet Version 6.3". Sigma Aldrich. 24 Jan 2025. Retrieved 25 February 2025.
  3. 1 2 3 4 5 6 7 "Anilofos". www.agropages.com. Retrieved 25 February 2025.
  4. 1 2 3 4 5 6 7 8 9 10 11 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
  5. 1 2 3 4 "Anilofos - Safety Data Sheet". www.chemicalbook.com.
  6. ↑ "Anilofos". pubchem.ncbi.nlm.nih.gov.
  7. ↑ "Anilofos LCSS". pubchem.ncbi.nlm.nih.gov. Retrieved 25 February 2025.
  8. 1 2 3 "Shoot (Anilofos 30% EC) herbicides Anilofos 30 used for control of annual grasses". Global Crop Care.
  9. ↑ "Anilofos CRM37876". www.sigmaaldrich.com. Retrieved 25 February 2025.
  10. 1 2 Singh, D. P.; Khattar, J. I. S.; Kaur, Mandeep; Kaur, Gurdeep; Gupta, Meenu; Singh, Yadvinder (31 January 2013). "Anilofos Tolerance and Its Mineralization by the Cyanobacterium Synechocystis sp. Strain PUPCCC 64". PLOS ONE. 8 (1): e53445. Bibcode:2013PLoSO...853445S. doi: 10.1371/journal.pone.0053445 . PMC   3561370 . PMID   23382844.
  11. ↑ 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
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