Phosalone (Ref: ENT 27163)

Phosalone (Ref: ENT 27163)	Last updated: 22/08/2024
(Also known as: benzofos; benzphos; NPH 1090; O,O-diethyl phosphorodithioate)

SUMMARY

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	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide and acaricide used to control Coleoptera, Homoptera, Lepidoptera and other pests mainly on fruit

Example pests controlled

Red spider mite; Caterpillars; Beetles; Codling moth; Seed weevil; Fruit maggots

Example applications

Potatoes; Artichokes; Nuts; Fruit including citrus, apples, pears, plums, apricots, grapes; Nuts; Roses

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1965, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Austria

Date EC 1107/2009 inclusion expires

Expired

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

C₁₂H₁₅ClNO₄PS₂

Canonical SMILES

CCOP(=S)(OCC)SCN1C2=C(C=C(C=C2)Cl)OC1=O

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IOUNQDKNJZEDEP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H15ClNO4PS2/c1-3-16-19(20,17-4-2)21-8-14-10-6-5-9(13)7-11(10)18-12(14)15/h5-7H,3-4,8H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Organophosphate insecticide; Organophosphate acaricide; Organothiophosphate insecticide; Organothiophosphate acaricide

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - S-chloromethyl O,O-diethyl phosphorodithioate

Substance origin

Synthetic

Mode of action

Non-systemic with contact and stomach action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

2310-17-0

EC number

218-996-2

CIPAC number

109

US EPA chemical code

097701

PubChem CID

4793

CLP index number

015-067-00-1

Molecular mass

367.8

PIN (Preferred Identification Name)

IUPAC name

S-6-chloro-2,3-dihydro-2-oxo-1,3-benzoxazol-3-ylmethyl O,O-diethyl phosphorodithioate

CAS name

(S-)(6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl) O,O-diethyl phosphorodithioate

Other status information

Severe Marine Pollutant; Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Boophilus microplus, Choristoneura rosaceana, Myzocallis coryli, Myzus persicae, Phorodon humuli, many others

Physical state

Colourless crystals

Formulations

Property

Value

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

Rhone-Poulenc

Example products using this active

Zolone
Azonfene
Benzofos
Rubitox

Formulation and application details

Supplied as an emulsifiable concentrate formulation for foliar, ground and aerial applications

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.4

Low

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

1000000

Acetone

26300

n-Heptane

1000000

Toluene

1000000

Ethyl acetate

Melting point (°C)

46.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

174.6

Flashpoint (°C)

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

1.02 X 10⁰⁴

Calculated

Log P

4.01

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.49

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

1.56 X 10^-02

Low volatility

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

2.04 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution: 203nm = 46918, 236nm = 14820, 284nm = 4602, 291nm = 3575

Surface tension (mN m⁻¹)

71.78

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

7.2

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.8-4.9 days, DT₉₀ range 2.8-16.3 days; Other sources: DT₅₀ 21 days (DW3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.7

Note

Published literature RL₅₀ range 1.4-9.9 days, 5 field & undercover grown crops, various matrices, n=7

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.5

Note

Published literature RL₅₀ range 2.5-16.0 days, 3 field crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

3.8

Moderately fast

Note

DT₅₀ 1.8 days in summer, 5.8 days in winter, artificial light, 40 deg N

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

Value

321

Persistent

Note

pH sensitive: DT₅₀ 365 days at pH 4, 17.8 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

2.8

Moderately fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

[Grapes: 5.6 days @ 25 DegC; Field study], [Grapes: 11.4 days @ 4 DegC; Field study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

21.2

Slightly mobile

K_oc (mL g⁻¹)

2063

Notes and range

EU dossier K_oc range 870-2680 mL g⁻¹, degradation reported with clay

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.21

Calculated

Low leachability

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

Value

5.55 X 10^-04

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

0.07

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

180

Whole fish

Threshold for concern

CT₅₀ (days)

0.71

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

S-6-chloro-2,3-dihydro-2-oxo-benzoxazol-3-ylmethyl (Ref: AE0941954)

Water (Hydrolysis @ pH9)

6-chloro-2(3H)-benzoxazolone (Ref: AE F054014)

Water (Hydrolysis @ pH9)

2-amino-5-chlorophenol (Ref: AE F114970)

Water (Anaerobic)

deschlorophosalone (Ref: RP 11690)

Plant

6-chlorobenzoxazolone (Ref: RP 11881)

Plant

desethyl phosalone

Phosalone metabolite M01

Rat

2-hydroxy-p-chloroaniline (Ref: RP 18709)

Rat

2-amino-7-chloro-3H-phenoxazin-3-one (Ref: AE 0651017)

phenoxazone (Ref: AE 0651017)

RP18726

Water

6-chloro-2,3-dihydro-3-methylthiomethyl-1,3-benzoxazol-2-one (Ref: RP 19914)

Animal (Liver)

6-chloro-2,3-dihydro-3-methylsulfinylmethyl-1,3-benzoxazol-2-one (Ref: RP 19889)

Animal (Liver)

oxophosalone (Ref: RP 12244)

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

120

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.9

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

503

Gallus domesticus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

1659 mg kg feed⁻¹

Anas platyrhynchos

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

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

22.5

Moderate

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

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 12.7 mg kg⁻¹ soil

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)

4.4

Apis mellifera

Moderate

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

102

Apis mellifera

Low

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)

> 4.39

Bombus terrestris

Moderate

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

> 3.98

Bombus terrestris

Moderate

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) as % Mortslity at dose 0.72 kg ha⁻¹

100

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

45.8

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.63

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.056

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.05

Danio rerio

Moderate

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

0.00074

Daphnia magna

High

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

0.00014

Daphnia magna

High

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

0.019

Chironomus riparius

Moderate

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)

1.1

Scenedesmus subspicatus

Moderate

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

0.1

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

120

Rat

Moderate

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

1530

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.26

Rat

Other Mammal toxicity endpoints

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

0.01

Dog SF=100

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

0.1

Rabbit SF=100

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

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

0.01

Dog SF=100

Dermal penetration studies (%)

0.7-3.6

concentration dependent

Dangerous Substances Directive 76/464

List I; List II

Exposure Routes

Public

No unacceptable risks to bystanders identified
Dietary risk is considered low

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

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

Rapid excretion mainly via the urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No dats

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive
IMDG Transport Hazard Class 6.1
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H301, H312, H317, H332
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

phosalone

French

phosalone

German

Phosalon

Danish

phosalon

Italian

fosalone

Spanish

fosalon

Greek

Polish

fosalon

Swedish

Hungarian

phosalon

Dutch

Norwegian

Record last updated:	22/08/2024
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