Dicrotophos (Ref: OMS 253)

Dicrotophos (Ref: OMS 253)	Last updated: 22/08/2024
(Also known as: ENT 24482; SD 3546; carbomicron ; dicrotofos; C709)

SUMMARY

Dicrotofos is an organophosphate insecticide. It has a high aqueous solubility, quite volatile and, based on its chemical properties, it may leach to groundwater. It is not usually persistent in soils. It is highly toxic to mammals and has a low tendency to bioaccumulate. Dicrotofos is also an acetyl cholinesterase inhibitor. It has a highly toxicity to most biodiversity including honeybees and earthworms. However, it appears to be slightly less toxic to fish.

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 High alert: GUS: High leachability Warning: Significant data are missing	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: Mammals acute toxicity: High; Acetyl cholinesterase inhibitor

GENERAL INFORMATION

Description

An insecticide used to control sucking and chewing pests, boring insects and mites

Example pests controlled

Aphids; Thrips; Spider mites; Fleahoppers; Sink bugs; Lygus bugs; Caterpillars; Boll weevils; Elm bark bettle

Example applications

Coffee; Cotton; Rice; Pecans; Non-food producing and ornamental trees

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1965, introduced

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK 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

Not applicable

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

Isomeric existing in the E- and Z-forms. The E-isomer is more insecticidally active than the Z-isomer.

Chemical formula

C₈H₁₆NO₅P

Canonical SMILES

CC(=CC(=O)N(C)C)OP(=O)(OC)OC

Isomeric SMILES

O=P(O/C(=C/C(=O)N(C)C)C)(OC)OC

International Chemical Identifier key (InChIKey)

VEENJGZXVHKXNB-VOTSOKGWSA-N

International Chemical Identifier (InChI)

InChI=1S/C8H16NO5P/c1-7(6-8(10)9(2)3)14-15(11,12-4)13-5/h6H,1-5H3/b7-6+

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Organophosphate insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic with contact and stomach action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

141-66-2

EC number

205-494-3

CIPAC number

299

US EPA chemical code

035201

PubChem CID

5371560

CLP index number

015-073-00-4

Molecular mass

237.19

PIN (Preferred Identification Name)

(2E)-4-(dimethylamino)-4-oxobut-2-en-2-yl dimethyl phosphate

IUPAC name

(E)-2-dimethylcarbamoyl-1-methylvinyl dimethyl phosphate

CAS name

(1E)-3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate

Other status information

Potential groundwater pollutant; Marine Pollutant

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

Leucoptera meyricki, Lygus lineolaris, Panonychus ulmi, Psylla pyricola, Bemisia tabaci, Boophilus microplus, many others

Physical state

Yellow brown liquid

Formulations

Property

Value

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

Amvac Chemical Co
Shell
Ciba-Geigy
Kenogard

Example products using this active

Carbicron
Ektafos
Carbomicron
Bidrin
Diapadrin

Formulation and application details

Often supplied as a water soluble concentrate or ULV spray.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1000000

at 25 °C

High

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

Miscible

Acetone

Miscible

Xylene

Miscible

Dichloromethane

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

3.16 X 10^-01

Calculated

Log P

-0.5

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

9.3

Moderately volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

5.10 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ (days) on plant matrix

Value

1.0

Note

Cotton leaves, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

Notes and range

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

3.08

Calculated

High leachability

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

Value

2.83 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

Estimated

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

butanamide

N,N-dimethylacetoacetamide

Major fraction

0.20

2-hydroxy-N,N-dimethylacetamide

Flooded soil

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

monocrotophos (Ref: ENT 27129)

Animal; Plants

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.05

Rat 2 yr

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

9.63

Anas platyrhynchos

High

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)

0.036

Apis mellifera

High

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

0.068

Apis mellifera

High

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)

0.0003

Megachile rotundata

High

Mode of exposure

Contact

Other bee species (2)

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

0.685

Trigona spinipes

High

Mode of exposure

Contact

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

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

6.3

Oncorhynchus mykiss

Moderate

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

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

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

0.013

Daphnia magna

High

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

0.00099

Daphnia magna

High

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

> 0.014

Ceriodaphnia dubia LC₅₀

High

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

0.077

Americamysis bahia

High

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)

Rat

High

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

110

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.09

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

Low risk to Europeans as no longer approved for use

Occupational

Rapidly absorbed through the skin, PPE/PPC essential

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Toxic if ingested, inhaled or by skin contact
US EPA - weak evidence to support carcinogen classification

Handling issues

Property

Value and interpretation

General

IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H300, H311
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

UN Number

UN3018

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

dicrotophos

French

dicrotophos

German

Dicrotophos

Danish

dicrotophos

Italian

dicrotofos

Spanish

dicrotofos

Greek

dicrotophos

Polish

dikrotofos

Swedish

Hungarian

Dutch

dicrotofos

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