Carpropamid is a rice fungicide. It is not very soluble in water, volatile and, based on its chemical properties, it is non-mobile. Little is known regarding its persistent in soil and aquatic systems. It is not highly toxic to mammals. It shows a moderate level of toxicity to birds, fish and earthworms.
Hazard 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. These hazard alerts do not take account of usage patterns or exposure, thus do not represent risk.
Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate
Human health Low alert
Warning: Significant data are missing
GENERAL INFORMATION
Description
A systemic fungicide primarily used in rice cultivation
Example pests controlled
Rice blast fungus (Magnaporthe grisea)
Example applications
Rice
Efficacy & activity
-
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
GB LERAP status
No UK approval for use as a plant protection agent
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
Not applicable
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
Carpropamid exhibits diastereomeric isomerism due to the presence of multiple chiral centres in its cyclopropane ring and side chains. The technical material is a mixture of four stereoisomers, specifically: (1R,3S,1'R), (1S,3R,1'R), (1S,3R,1'S), and (1R,3S,1'S). These isomers differ in the spatial arrangement of atoms around the chiral centres, which significantly affects their biological activity. The 1S,3R,1'R isomer has been identified as the most effective against rice blast.
Systemic, protective, melanin inhibiting - no curative properties but does induce disease resistance in rice plants. Shown to be a potent inhibitor of scytalone dehydratase, the target enzyme in the melanin biosynthesis pathway of the rice blast fungus.
CAS RN
104030-54-8
EC number
No data found
CIPAC number
None allocated
US EPA chemical code
Not listed
PubChem CID
153847
CLP index number
No data found
Molecular mass
334.67
PIN (Preferred Identification Name)
A mixture of : (1R*,3S*)-2,2-dichloro-N-[(1R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropane-1-carboxamide and (1R*,3S*)-2,2-dichloro-N-[(1S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropane-1-carboxamide where the first pair cited comprises at least 95% of the total
IUPAC name
A mixture of: (1R,3S)-2,2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, (1S,3R)-2,2-dichloro-N-[(R)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide, (1S,3R)-2,2-dichloro-N-[(S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide and (1R,3S)-2,2-dichloro-N-[(S)-1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide where the first two cited comprise at least 95% of the total
Example manufacturers & suppliers of products using this active now or historically
Bayer
Zeneca Agrochemicals
Syngenta
Example products using this active
Arcado
Protega
Formulation and application details
Often supplied as a suspension concentrate
Commercial production
Carpropamid is synthesised through a targeted condensation reaction that forms its distinctive cyclopropylcarboxamide structure. The production begins with 2,2-dichloro-1-ethyl-3-methylcyclopropanecarboxylic acid, which is reacted with 1-(4-chlorophenyl)ethylamine. This formal condensation of the carboxylic acid group with the amine yields the active compound, carpropamid.
Impact on climate of production and use
Data for the amount of life cycle GHGs produced by carpropamide are not available in the public domain. However, whilst estimates vary, more general data suggests that between 11 and 30 kilograms of CO₂e is emitted per kilogram of fungicide produced.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1.8
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
-
-
-
Melting point (°C)
159.7
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
-
Boiling point (°C)
-
-
-
Degradation point (°C)
-
-
-
Flashpoint (°C)
-
-
-
Octanol-water partition coefficient at pH 7, 20 °C
P
1.78 X 1004
Calculated
-
Log P
4.25
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
High
Fat solubility of residues
Solubility
-
-
-
Data type
-
-
-
Density (g ml⁻¹)
1.17
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)
0.0025
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.50 X 10-04
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
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)
-
-
-
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
DT₅₀ in paddy fields reported to be several weeks to several months.
Dissipation rate RL₅₀ (days) on plant matrix
Value
-
-
-
Note
-
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)
-
-
-
Sediment 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
Kd (mL g⁻¹)
-
Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source
Non-mobile
Koc (mL g⁻¹)
4917
Notes and range
Estimated
Freundlich
Kf (mL g⁻¹)
-
-
-
Kfoc (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
-
-
-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated
-
-
Note
-
Potential for particle bound transport index
-
-
-
Potential for loss via drain flow
Non-mobile
Calculated
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
-
-
-
CT₅₀ (days)
-
-
Known metabolites
None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Rat
Low
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)
> 2000
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Phasianidae
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
-
-
-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
-
-
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
> 1000
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Eisenia foetida
Low
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
-
-
-
Soil micro-organisms
-
-
-
Collembola
Acute LC₅₀ (mg kg⁻¹)
-
-
-
Chronic NOEC (mg kg⁻¹)
-
-
-
Non-target plants
Vegetative vigour ER₅₀ (g ha⁻¹)
-
-
-
Seedling emergence ER₅₀ (g ha⁻¹)
-
-
-
Honeybees (Apis 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)
-
-
-
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
-
-
-
Chronic
-
-
-
Notes
-
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)
-
-
-
Mode of exposure
-
Other bee species (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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
5.6
L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source
Cyprinidae spp.
Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
-
-
-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
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
Environmental fate
Warning:
Ecotoxicity
