Anilofos (Ref: HOE 30374)

Anilofos (Ref: HOE 30374)	Last updated: 01/09/2023
(Also known as: HOE 574; anilophos; arozin)

SUMMARY

Anilofos is an organophosphate herbicide used to control annual grass weeds and sedges. It has a low aqueous solubility and a low volatility. It may be moderately persistent in soil systems depending on conditions. It moderately toxic to fish, aquatic invertebrates and honeybees but less so to birds. Anilofos is moderately toxic to mammals via the oral route. It is also a neurotoxin and a recognised irritant.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate	Human health High alert: Acetyl cholinesterase inhibitor; Neurotoxicant Warning: Significant data are missing

GENERAL INFORMATION

Description

Used for pre-emergence and early post-emergence control annual grass weeds and sedges in directly sown and transplanted rice crops

Example pests controlled

Indian goosegrass; Barnyard grass; Flatsedge; Yellow nutsedge; Cockspur

Example applications

Rice

Efficacy & activity

Availability status

Introduction & key dates

circa 1980

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₉ClNO₃PS₂

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NXQDBZGWYSEGFL-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H20ClN5O2/c1-2-20(12-8-4-3-5-9-12)15(23)22-16(24)21(18-19-22)14-11-7-6-10-13(14)17/h6-7,10-12H,2-5,8-9H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Organophosphate herbicide

Minimum active substance purity

95%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, absorbed mainly through roots and works by inhibiting cell division, inhibition of VLCFAs.

CAS RN

64249-01-0

EC number

264-756-5

CIPAC number

None allocated

US EPA chemical code

Not listed

PubChem CID

91687

CLP index number

No data found

Molecular mass

367.85

PIN (Preferred Identification Name)

S-{2-[(4-chlorophenyl)(propan-2-yl)amino]-2-oxoethyl} O,O-dimethyl phosphorodithioate

IUPAC name

S-4-chloro-N-isopropylcarbaniloylmethyl O,O-dimethyl phosphorodithioate

CAS name

S-(2-((4-chlorophenyl)(1-methylethyl)amino)-2-oxoethyl) O,O-dimethyl phosphorodithioate

Other status information

PAN Bad Actor Chemical

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Colourless to light brown crystalline solid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Bayer CropScience
BOC Sciences

Example products using this active

Arrozin
Ricozin
Aniloguard
Anilo-Tox

Formulation and application details

Usually supplied as an emulsifiable concentrate, granules and dispersible powders

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

9.4

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

1000000

Toluene

1000000

Acetone

2000000

Ethyl acetate

12000

Hexane

Melting point (°C)

Boiling point (°C)

443.6

Degradation point (°C)

150

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

6.46 X 10⁰³

Calculated

Log P

3.81

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.322

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

2.2

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature DT₅₀ values 30-45 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.3

Note

Published literature RL₅₀ range 1.3-3.8 days, various matrices from rice, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Not sensitive to UV light

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

7.48

Slightly mobile

K_foc

1084

¹/_n

No data

Notes and range

K_f range 3.35-11.73, K_foc range 771-1288 mL g⁻¹ soils =4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.52

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

3.99 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

472

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 3360

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

5.9

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 2.8

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 56.0

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

472

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

26.0

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List I; List II

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302

WHO Classification

II (Moderately hazardous)

UN Number

UN2783

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Limited shelf-life. Store 0-6 DegC

TRANSLATIONS

Language

Name

English

anilofos

French

German

Danish

Italian

Spanish

Greek

Polish

anilofos

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	01/09/2023
Contact:	aeru@herts.ac.uk
Please cite as:	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