Dicrotophos (Ref: OMS 253)-Pesticide database

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Dicrotophos (Ref: OMS 253)

(Also known as: ENT 24482; SD 3546; carbomicron ; dicrotofos; C709)

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.

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

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

Introduction & key dates

UK regulatory status

UK COPR regulatory status

Date COPR inclusion expires

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

Listed in EU database

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

Chemical structure

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?

Insecticide, Acaricide

Substance groups

Organophosphate insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

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

US EPA chemical code

CLP index number

PIN (Preferred Identification Name)

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

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

(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 Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

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

Yellow brown liquid

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

Source; quality score; and other information

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

V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Dichloromethane

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data

Fat solubility of residues

Density (g ml⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data

Moderately volatile

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

H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data

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

Surface tension (mN m⁻¹)

Source; quality score; and other information

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
4 = Verified data

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Best available data

Dissipation rate RL₅₀ on plant matrix

R3 R = Peer reviewed scientific publications
3 = Unverified data of known source

Cotton leaves, n=1

Dissipation rate RL₅₀ on and in plant matrix

Aqueous photolysis DT₅₀ (days) at pH 7

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

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Source; quality score; and other information

M3 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
3 = Unverified data of known source

Moderately mobile

Notes and range

Notes and range

Source; quality score; and other information

GUS leaching potential index

High leachability

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

Potential for particle bound transport index

Potential for loss via drain flow

Moderately mobile

Bio-concentration factor

BCF (l kg⁻¹)

Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source

CT₅₀ (days)

Known soil metabolites

Major/Minor fraction

Estimated maximum occurrence fraction

N,N-dimethylacetoacetamide

2-hydroxy-N,N-dimethylacetamide

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

monocrotophos (Ref: ENT 27129)

Terrestrial ecotoxicology

Source; quality score; and other information

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Short term dietary NOEL

L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source

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

Birds - Acute LD₅₀ (mg kg⁻¹)

F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data

Anas platyrhynchos

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

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)

F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source

Apis mellifera

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

F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data

Apis mellifera

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

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)

R4 R = Peer reviewed scientific publications
4 = Verified data

Megachile rotundata

Mode of exposure

Other bee species (2)

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

R4 R = Peer reviewed scientific publications
4 = Verified data

Trigona spinipes

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Source; quality score; and other information

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data

Oncorhynchus mykiss

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source

Daphnia magna

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

F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source

Daphnia magna

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

F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source

Americamysis bahia

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

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

Source; quality score; and other information

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Inhalation LC₅₀ (mg l⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

Low risk to Europeans as no longer approved for use

Rapidly absorbed through the skin, PPE/PPC essential

EU MRL pesticide database

GB MRL Register

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Specific human health issues

Endocrine disruptor

?Possibly, status not identified

A0 A = Chromosome aberration (EFSA database)
0 = No data

B0 B = DNA damage/repair (EFSA database)
0 = No data

C0 C = Gene mutation (EFSA database)
0 = No data

D0 D = Genome mutation (EFSA database)
0 = No data

E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results

?Possibly, status not identified

Reproduction / development effects

Acetyl cholinesterase inhibitor

✓Yes, known to cause a problem

Respiratory tract irritant

Skin sensitiser

?Possibly, status not identified

?Possibly, status not identified

General human health issues

Toxic if ingested, inhaled or by skin contact

Handling issues

Value and interpretation

IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H300, H311
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

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