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Imiprothrin (Ref: S 41311)
Last updated: 25/05/2018
(Not known by any other names)

GENERAL INFORMATION
Description
Used mainly for non-crop applications to control of a range of common insect pests
Example pests controlled
Cockroaches, Ants, Crickets, silverfish
Example applications
Indoor amentity; Domestic; Public hygiene
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1996, Japan; 1998, USA
UK regulatory status
UK approval status
Not approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) or known to be used (#) in the following EU-27 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
                 
Also used in
Also used in
USA
Chemical structure
Isomerism
Imiprothrin is a chiral molecule. The technical materail is a mixture of (1R)-cis- and (1R)-trans- isomers in an approximate ratio of 20:80.
Chemical formula
C₁₇H₂₂N₂O₄
Canonical SMILES
CC(=CC1C(C1(C)C)C(=O)OCN2C(=O)CN(C2=O)CC#C)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
VPRAQYXPZIFIOH-PYMCNQPYSA-N
International Chemical Identifier (InChI)
InChI=1S/C17H22N2O4/c1-6-7-18-9-13(20)19(16(18)22)10-23-15(21)14-12(8-11(2)3)17(14,4)5/h1,8,12,14H,7,9-10H2,2-5H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Insecticide
Substance group
Pyrethroid
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Similar to other synthetic pyrethoids, acts by over stimulation of the nervous system. Sodium channel modulator.
CAS RN
72963-72-5
EC number
428-790-6
CIPAC number
None allocated
US EPA chemical code
004006
PubChem CID
123622
Molecular mass
318.37
PIN (Preferred Identification Name)
Mix of: [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate and [2,5-dioxo-3-(prop-2-yn-1-yl)imidazolidin-1-yl]methyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
IUPAC name
Mix of: 2,5-dioxo-3-prop-2-ynylimidazolidin-1-ylmethyl (1R,3S)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate and 2,5-dioxo-3-prop-2-ynylimidazolidin-1-ylmethyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CAS name
[2,5-dioxo-3-(2-propynyl)-1-imidazolidinyl]methyl (1R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other status information
PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
3A
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
None recorded
Physical state
Yellow viscous liquid with sweet odour
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Pralle
Example products using this active
  • Sumitomo Chemical Co. Ltd
UK LERAP status
No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details
Usually used as crack, crevice and spot application
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
93.5
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
6200
P3 P = Other governments and regulators
3 = Unverified data of known source
Hexane
-
Melting point (°C)
25
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
-
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
141
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
(closed cup)
-
Octanol-water partition coefficient at pH 7, 20 °C
P
2.69 X 1002 Calculated -
Log P
2.43
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Low
Bulk density (g ml⁻¹)
1.122
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
Not applicable
P3 P = Other governments and regulators
3 = Unverified data of known source
-
No dissociation
Vapour pressure at 20 °C (mPa)
0.00186
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
6.25 X 10-06
P3 P = Other governments and regulators
3 = Unverified data of known source
Non-volatile
GUS leaching potential index
0.98 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
3.83 X 10-03 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
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)
5
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Trans isomer: DT₅₀ 1.6-2.5 days, cis isomer: DT₅₀ 3.3–12.5 days
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
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
58.6
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Moderately persistent
Note
pH sensitive: stable at pH 5, 1 day at pH 9 (L3)
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Moderately mobile
Koc
402
Notes and range
Other sources: 268 mL g⁻¹ for sewage sludge and suggests moderate mobility (B3)
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
N-carbamoyl-N-propargylglycine CPG - - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
B3 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
3 = Unverified data of known source
Based on LogP < 3
Low risk
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
900
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
P3 P = Other governments and regulators
3 = Unverified data of known source
Rat
-
(ppm diet)
100 -
Birds - Acute LD₅₀ (mg kg⁻¹)
5620
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Colinus virginianus
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.038
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Oncorhynchus mykiss
High
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.051
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
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)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
3.1
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Pseudokirchneriella subcapitata
Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.4
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
High
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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 pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
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)
900
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
P3 P = Other governments and regulators
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
>= 1.2
P3 P = Other governments and regulators
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
- - -
Exposure Routes
Public
Negligible risk to bystanders considering authorised uses
Occupational
-
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
?Possibly, status not identified
No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
Not explosive
CLP classification 2013
-
EC Risk Classification
Xn - Harmful: R22
N - dangerous for the environment: R50/53
EC Safety Classification
S2, S60, S61
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
imiprothrin
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
imiprotrin
Hungarian
-
Dutch
-

Record last updated: 25/05/2018
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