anilofos

{{Chembox

| Name = Anilofos

| ImageFile = Anilofos 200.svg

| OtherNames = Anilophos, Arozin

| IUPACName = S-4-chloro-N-isopropylcarbaniloylmethyl-O, O-dimethylphosphorodithioate

| SystematicName =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 64249-01-0

| ChEBI = 81728

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 82790

| EC_number = 264-756-5

| KEGG = C18394

| PubChem = 91687

| UNII = 71W48U40S6

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NXQDBZGWYSEGFL-UHFFFAOYSA-N

| SMILES = CC(C)N(C1=CC=C(C=C1)Cl)C(=O)CSP(=S)(OC)OC

}}

| Section2 = {{Chembox Properties

| C=13|H=19|Cl=1|N=1|O=3|P=1|S=2

| Appearance = white-to-brown solid{{cite web |title=Anilofos Safety Datasheet Version 6.3 |url=https://www.sigmaaldrich.com/AU/en/sds/SIAL/37876?userType=undefined |publisher=Sigma Aldrich |access-date=25 February 2025 |date=24 Jan 2025}}{{cite web |title=Anilofos |url=https://www.agropages.com/agrodata/Detail-52.htm |website=www.agropages.com |access-date=25 February 2025}}

| Density = 1.322 t/m³

| MeltingPtC = 51

| MeltingPt_notes = {{cite web |title=Anilofos - Safety Data Sheet |url=https://www.chemicalbook.com/msds/Anilofos.htm |website=www.chemicalbook.com}}

| BoilingPtC = 444

| BoilingPt_notes =

| Solubility = 9.4 mg/L

| Solvent1 = acetone

| Solubility1 = >700 g/L

| Solvent2 = chloroform

| Solubility2 = >700 g/L

| Solvent3 = toluene

| Solubility3 = >700 g/L

| VaporPressure = 2.2 mPa

}}

| Section3 = {{Chembox Hazards

| MainHazards = Acute oral toxicity, irritation

| FlashPt = 221°C, 430°F

| GHS_ref= {{cite web |title=Anilofos |url=https://pubchem.ncbi.nlm.nih.gov/compound/91687#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302}}

| PPhrases = {{P-phrases|264|270|301+317|330|501}}{{cite web |title=Anilofos LCSS |url=https://pubchem.ncbi.nlm.nih.gov/compound/Anilofos#datasheet=LCSS |website=pubchem.ncbi.nlm.nih.gov |access-date=25 February 2025 |language=en}}

| AutoignitionPt =

| LD50 = {{ubl|472 mg/kg (rat, oral)|>2000 mg/kg (rabbit, dermal)}}

| LC50 = {{ubl|26 g/m³ (rat, inhalation, 4 hr)|2.8 mg/L (trout, 96 hr)}}

}}

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.{{cite journal |last1=Hazarika |first1=Archana |last2=Sarkar |first2=S.N. |title=Effect of isoproturon pretreatment on the biochemical toxicodynamics of anilofos in male rats |journal=Toxicology |date=August 2001 |volume=165 |issue=2–3 |pages=87–95 |doi=10.1016/S0300-483X(01)00411-5|pmid=11522367 |bibcode=2001Toxgy.165...87H }} It was brought to market circa 1980.

Usage

Anilophos's herbicide resistance classification is group K (Australia), K3 (global), or 15 (numeric), 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, producing discolouration, stunted growth and death.

Anilofos is not approved in the European Union under Regulation No. 1107/2009.{{cite web |title=Anilofos CRM37876 |url=https://www.sigmaaldrich.com/AU/en/product/supelco/crm37876 |website=www.sigmaaldrich.com |access-date=25 February 2025}} It controls Indian goosegrass, barnyard grass, flatsedge, yellow nutsedge and cockspur. It is used on rice, paddy and soybean.{{cite web |title=Shoot (Anilofos 30% EC) herbicides Anilofos 30 used for control of annual grasses |url=https://www.globalcropcare.com/product/shool-anilofos-30-ec/ |website=Global Crop Care}}

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.

Forumations in India are sold as 18% or 30% emulsifiable concentrates. {{convert|631|t|lb}} was used in 2007, 2.6% of India's total herbicide usage.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

Properties

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

Anilofos is chemically stable under standard conditions, but under intense heating may form an explodable mixture with air. It has low volatility.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 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. It is insoluble in water.

Anilofos is a thiono organophosphate.{{cite journal |last1=Hazarika |first1=Archana |last2=Sarkar |first2=S.N. |title=Effect of isoproturon pretreatment on the biochemical toxicodynamics of anilofos in male rats |journal=Toxicology |date=August 2001 |volume=165 |issue=2–3 |pages=87–95 |doi=10.1016/S0300-483X(01)00411-5|pmid=11522367 |bibcode=2001Toxgy.165...87H }}

Environmental behaviour

Anilofos is moderately persistent in soil, with a half-life of about 38 days, although in flooded soil it dissipates faster, in 5 to 25 days.{{cite journal |last1=Singh |first1=D. P. |last2=Khattar |first2=J. I. S. |last3=Kaur |first3=Mandeep |last4=Kaur |first4=Gurdeep |last5=Gupta |first5=Meenu |last6=Singh |first6=Yadvinder |title=Anilofos Tolerance and Its Mineralization by the Cyanobacterium Synechocystis sp. Strain PUPCCC 64 |journal=PLOS ONE |date=31 January 2013 |volume=8 |issue=1 |pages=e53445 |doi=10.1371/journal.pone.0053445|doi-access=free |pmid=23382844 |bibcode=2013PLoSO...853445S }} It doesn't bioaccumulate in soil and shows no tendency for groundwater leaching. The water half-life is also short. 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.

Safety

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

anilofos

Usage

Properties

Environmental behaviour

Safety

References

Links