Monocrotophos (Ref: ENT 27129)

Monocrotophos (Ref: ENT 27129)	Last updated: 19/01/2023
(Also known as: azadrin; corophos; OMS 834)

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 High alert: GUS: High leachability; Drainflow: Mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

Used to control sucking and chewing pests typically on cotton, citrus and many other crops

Example pests controlled

Aphids; Common mites; Ticks; Spiders; Caterpillars

Example applications

Cotton; Palms; Ornamental conifers; Ornamental shrubs and flowers; Peanuts; Sugarcane; Citrus; Olives

Efficacy & activity

Availability status

Banned in many countries

Introduction & key dates

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Italy

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

Additional information

Also used in

Chemical structure

Isomerism

Exists in the cis- and trans-forms.The cis-form is the major constituent of the technical material.

Chemical formula

C₇H₁₄NO₅P

Canonical SMILES

C/C(=C\C(=O)NC)/OP(=O)(OC)OC

Isomeric SMILES

C/C(=C\C(=O)NC)/OP(=O)(OC)OC

International Chemical Identifier key (InChIKey)

KRTSDMXIXPKRQR-AATRIKPKSA-N

International Chemical Identifier (InChI)

InChI=1S/C7H14NO5P/c1-6(5-7(9)8-2)13-14(10,11-3)12-4/h5H,1-4H3,(H,8,9)/b6-5+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
monocrotophos	-

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Organophosphate insecticide; Organophosphate acaricide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Broad spectrum, systemic with stomach and contact action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

6923-22-4

EC number

230-042-7

CIPAC number

287

US EPA chemical code

058903

PubChem CID

5371562

CLP index number

015-072-00-9

Molecular mass

223.16

PIN (Preferred Identification Name)

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

IUPAC name

dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinyl phosphate

CAS name

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

Other status information

PIC Annex III; Marine Pollutant; Rotterdam Convention (Class Ib)

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Bemisia tabaci, Boophilus microplus, Cacopsylla pyri, Earias vittella, Lygus hesperus, Spodoptera littoralis, many others

Physical state

Colourless crystals when pure reddish-brown as technical substance

Formulations

Property

Value

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

BASF
AgroCare
King Tech Corp
United Phosphorus

Example products using this active

Nuvacron
Crisodrin
Monophos
Monodrin
Phoskill

Formulation and application details

Available as a water soluble concentrate and ULV formulation

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

818000

High

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

700000

Acetone

1000000

Methanol

10000

Toluene

292000

Ethanol

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

6.03 X 10^-01

Calculated

Log P

-0.22

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.16

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.29

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)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Literature values for soil DT₅₀ range 1-35 days

Dissipation rate RL₅₀ on plant matrix

Value

5.0

Note

Published literature RL₅₀ range 2.4-7.8 days, 2 field grown crops, various matrices, n=2

Dissipation rate RL₅₀ on and in plant matrix

Value

3.7

Note

Published literature RL₅₀ range 1.3-14.5 days, 10 field grown crops, various matrices, n=11

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

134

Persistent

Note

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

Mobile

K_oc

Notes and range

Literature values for K_oc range 0.9-30.8 mL g⁻¹

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

4.02

Calculated

High leachability

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

Value

8.78 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known metabolites

None

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)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 0.94

Colinus virginianus

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)

Moderate

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)

0.13

Apis mellifera

High

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

0.02

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 pollinators (1)

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

1.1

Megachile rotundata

Moderate

Mode of exposure

Contact

Other pollinators (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)

> 7.0

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.023

Daphnia magna

High

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)

Rat

High

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

157

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.0006

JMPR 1995

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

0.002

JMPR 1995

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

Minimal risk from food residues
Exposure by general public unlikely

Occupational

Full protective clothing required including respirator to minimise operator and worker exposure
May be absorbed through skin

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

In mammals, 60-65% is excreted within 24 hours, predominantly in the urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Highly toxic orally

Handling issues

Property

Value and interpretation

General

Corrosive
IMDG Transport Code is 6.1

CLP classification 2013

Health: H300, H311; H330; H340
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

UN Number

2783

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

monocrotophos

French

monocrotophos

German

Monocrotophos

Danish

Italian

Spanish

monocrotofos

Greek

Polish

monokrotofos

Swedish

Hungarian

Dutch

Record last updated:	19/01/2023
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