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Dicrotophos (Ref: OMS 253)
Last updated: 22/02/2024
(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
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)
1B
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
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
at 25 °C
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene
-
Miscible
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
P
3.16 X 10-01 Calculated -
Log P
-0.5
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
Low
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.22
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)
9.3
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)
5.10 X 10-06
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
Non-volatile
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)
28
M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
4 = Verified data
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 on plant matrix
Value
1.0
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
-
Note
Cotton leaves, n=1
Dissipation rate RL₅₀ 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)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
M3 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
3 = Unverified data of known source
Moderately mobile
Koc
75
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
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 -
Bio-concentration factor
BCF (l kg⁻¹)
75
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Estimated
Low potential
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
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
Metabolising enzymes
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)
22
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
Rat
High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
0.05
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr
High
(ppm diet)
1 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
9.63
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
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
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
High
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.068
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
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
R4 R = Peer reviewed scientific publications
4 = Verified data
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
R4 R = Peer reviewed scientific publications
4 = Verified data
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
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
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
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
High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.00099
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
High
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 0.014
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
Ceriodaphnia dubia LC₅₀
High
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
0.077
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
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
- - -
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)
22
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
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
110
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.09
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
XNo, known not to cause a problem
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 Neurotoxicant
No data found
Yes, known to cause a problem
No data found
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
?Possibly, status not identified
No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
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: 22/02/2024
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