Fenitrothion (Ref: OMS 43)

Fenitrothion (Ref: OMS 43)	Last updated: 28/10/2024
(Also known as: MEP; OMS 223; ENT 25715)

SUMMARY

Fenitrothion is an insecticide for the control of sucking and chewing pests. It has a low aqueous solubility, is highly soluble in many organic solvents and is volatile. Fenitrothion has a low potential for leaching to groundwater and is not expected to be persistent in soil or water systems. It is moderately toxic to mammals, considered to be an endocrine disrupter and a cholinesterase inhibitor. It is highly toxic to birds, aquatic invertebrates and honeybees, and moderately toxic to fish, algae and earthworms.

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	Ecotoxicity High alert: Birds acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Endocrine disrupter; Acetyl cholinesterase inhibitor

GENERAL INFORMATION

Description

An insecticide used to control chewing, sucking and boring pests on a range of crops.

Example pests controlled

Leafminers, Locusts, Stem borers, Wheat bugs, Flour beetles, Grain beetles, Grain weevils

Example applications

Cereals; Cotton; Rice; Top fruit; Vegetables; Forestry; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1960, first reported

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

Date EC 1107/2009 inclusion expires

Expired. Withdrawn 2007

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

Australia

Chemical structure

Isomerism

None

Chemical formula

C₉H₁₂NO₅PS

Canonical SMILES

CC1=C(C=CC(=C1)OP(=S)(OC)OC)[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

ZNOLGFHPUIJIMJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H12NO5PS/c1-7-6-8(4-5-9(7)10(11)12)15-16(17,13-2)14-3/h4-6H,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Other substance

Other bioactivity & uses

Biocide, Wood preservative

Substance groups

Organophosphate insecticide; Organothiophosphate insecticide; Phenyl organothiophosphate insecticide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - S-methyl fenitrothion <5g/Kg

Substance origin

Synthetic

Mode of action

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

CAS RN

122-14-5

EC number

204-524-2

CIPAC number

US EPA chemical code

105901

PubChem CID

31200

CLP index number

015-054-00-0

Molecular mass

277.23

PIN (Preferred Identification Name)

O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate

IUPAC name

O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate

CAS name

O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate

Other status information

Chemical subject to PIC regulations. USA: withdrawn 2020; Canada: voluntarily discontinued 2004; New Zealand: withdrawn 2016; India: restricted use only 2007

Relevant Environmental Water Quality Standards

UK Statutory standard for the protection of aquatic life in inland waters, coastal and territorial waters: 0.01 µg l⁻¹ as annual average

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

Many recorded cases, mosquitoes, Adoxophyes orana, Boophilus microplus, Lucilia cuprina, Myzus persicae, Spodoptera littoralis

Physical state

Yellow to brown coloured viscous liquid

Formulations

Property

Value

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

FCC
Agropharm
King Tech Corp
Bayer
Sumitomo
Denka, Kendon Plant Care Pty Ltd
Sumitomo Chemical Australia Pty Ltd

Example products using this active

IPM 400
Fenitrocap IPM400
Fenifos
Nition
Accothion
Novathion
Grain-Guard Duo Insecticide
Titan Dual Grain Treatment
Freezone Fenitrothion Insecticide

Formulation and application details

Supplied in a variety of formulations including emulsifiable concentrates, wettable powders, granules and dusts as well as ULV

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Low

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

25000

n-Hexane

500000

Methanol

500000

Acetone

500000

Ethyl acetate

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

210

Flashpoint (°C)

157

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

2.09 X 10⁰³

Calculated

Log P

3.32

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.328

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.676

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

9.86 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 290nm = 4210
Acidic solution: 290nm = 4390
Basic solution: 290nm = 2370

Surface tension (mN m⁻¹)

68.5

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

2.7

Non-persistent

DT₅₀ (lab at 20 °C)

2.7

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

4.48

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 0.04-1.98 days, DT₉₀ range 2.16-6.58 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

8.0

Note

Published literature RL₅₀ range 0.5-4.2 days, 7 field & undercover grown crops, various matrices, n=8

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.3

Note

Published literature RL₅₀ range 1.5-10.6 days, 15 field & undercover grown crops, various matrices, n=23; lettuce in cold storage RL₅₀=27 days.

Aqueous photolysis DT₅₀ (days) at pH 7

Value

3.5

Moderately fast

Note

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

Value

183

Persistent

Note

Slightly sensitive to pH: DT₅₀ 195 days at pH5, 100 days at pH 9

Water-sediment DT₅₀ (days)

1.57

Fast

Water phase only DT₅₀ (days)

1.1

Moderately fast

Sediment phase only DT₅₀ (days)

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

[Wheat grain: 14 wks @ 30 DegC, 50% RH; Modelled data], [Malt: 413 days @ 20-22 DegC, dark conditions; Field study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

2000

Notes and range

Freundlich

K_f (mL g⁻¹)

180

Slightly mobile

K_foc (mL g⁻¹)

791

¹/_n

0.982

Notes and range

EU dossier K_f range 4.9-830 mL g⁻¹, K_foc range 252-1966 mL g⁻¹, ¹/_n range 0.86-1.10, Soils=5

pH sensitivity

Some indication that adsorption may increase with decreasing pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.48

Calculated

Low leachability

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

Value

1.25 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

(Other literature values Log BCF ranger 0.8-2.9 (R3))

Low potential

CT₅₀ (days)

0.19

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-methyl-4-nitrophenol

Major fraction

0.445

aminofenitrothion

Aerobic

fenitrooxon

Aerobic

formylaminofenitrothion

desmethylfenitrooxon

Aerobic

3-methyl-4-nitroanisole

Aerobic

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

desmethylfenitrothion

Water

O,O-dimethyl O-(3-carboxy-4-nitrophenyl)phosphate

COOH-SMO

Water (Photolysis)

fenitrooxon

Water

acetylaminofenitrothion

Water

o-methyl o-hydrogen o-(3-methyl-4-nitrophenyl)phosphate

DM-SMO

Water (Photolysis)

o-methyl s-methyl o-(3-methyl-4-nitrophenyl)phosphorothioate

SCH3-SMT

Water (Photolysis)

o,o-dimethyl o-(3-methyl-4-nitrophenyl)phosphorothioate

SMO

Water (Photolysis)

carboxyfenitrothion

Water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

330

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

> 10

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

Birds - Acute LD₅₀ (mg kg⁻¹)

2.3

Phasianidae

High

Birds - Short term dietary (LC₅₀/LD₅₀)

23 mg kg bw⁻¹ day⁻¹

Unknown species

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

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

231

Eisenia foetida

Moderate

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

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 10 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)

0.16

Apis mellifera

High

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

0.20

Apis mellifera

High

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

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 95 hrs (range 24-120 hrs) - USEPA data]

Bumblebees (Bombus spp.)

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

0.756

Bombus terricola 48 hr

High

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)

0.1

Andrena erythronii

High

Mode of exposure

Contact

Other bee species (2)

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

0.039

Megachile rotundata

High

Mode of exposure

Contact

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as % Mortality at dose 2 x 750 g ha⁻¹

10.8

Aphidius rhopalosiphi Adult corr

Beneficial insects (Predatory mites) as % Mortality at dose 2 x 750 g ha⁻¹

5.6

Typhlodromus pyri Protonymph corr

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)

1.3

Oncorhynchus mykiss

Moderate

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

0.088

Oncorhynchus mykiss 96 day

Moderate

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

9.3

Danio rerio EC₅₀ Embryo

Moderate

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

0.0086

Daphnia magna

High

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

0.000087

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)

0.012

Chironomus salinarius,/i> 24 hr

High

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

0.0017

Chironomus riparius

High

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)

1.3

Raphidocelis subcapitata

Moderate

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

0.1

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

0.017

Aquatic invertebrates

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)

330

Rat

Moderate

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

890

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.2

Rat

Other Mammal toxicity endpoints

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

0.005

Rat SF=100

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

0.013

Rat 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)

Dermal penetration studies (%)

3.9-20.9

concentration dependent

Dangerous Substances Directive 76/464

List I; List II

Exposure Routes

Public

Occupational

Possible risk when applied inside glasshouses
Re-entry after application should be avoided

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Risk of serious eye damage
Bioaccumulates
Endocrine issues - Competitive binding to androgen receptor, inhibition of estrogens action

Handling issues

Property

Value and interpretation

General

Potentially explosive under certain conditions
Prevent generation of mists
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2810

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

fenitrothion

French

fenitrothion

German

Fenitrothion

Danish

fenitrothion

Italian

fenitrotion

Spanish

fenitrotion

Greek

fenitrothion

Polish

fenitrotion

Swedish

fenitrotion

Hungarian

fenitrothion

Dutch

fenitrothion

Norwegian

Record last updated:	28/10/2024
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