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Flamprop-M-isopropyl (Ref: WL 43425)
Last updated: 23/01/2021
(Also known as: flamprop-M; CL 901444; AC 901444; L-flamprop-isopropyl)

SUMMARY
Flamprop-M-isopropyl is a discontinued herbicide that no longer has approval for use in the EU. It has a low solubility in water, is volatile and there is some concern regarding risk of leaching to groundwater. It is moderately persistent in soils. Whilst it has a low mammalian toxicity there is some concern about bioaccumulation. No serious human heath risks have been identified. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.
GENERAL INFORMATION
Description
A translocated, post-emergence arylalanine herbicide used to control wild-oats
Example pests controlled
Avena fatua
Example applications
Wheat
Efficacy & activity
-
Availability status
Current
Introduction & key dates
circa 1978
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
                 
Also used in
Also used in
Australia
Chemical structure
Isomerism
Flamprop-M-isopropyl is the sterospecific ester of the L-isomer of flamprop.
Chemical formula
C₁₆H₁₃ClFNO₃
Canonical SMILES
CC(C)OC(=O)C(C)N(C1=CC(=C(C=C1)F)Cl)C(=O)C2=CC=CC=C2
Isomeric SMILES
C[C@@H](C(=O)OC(C)C)N(C1=CC(=C(C=C1)F)Cl)C(=O)C2=CC=CC=C2
International Chemical Identifier key (InChIKey)
IKVXBIIHQGXQRQ-CYBMUJFWSA-N
International Chemical Identifier (InChI)
InChI=1S/C19H19ClFNO3/c1-12(2)25-19(24)13(3)22(15-9-10-17(21)16(20)11-15)18(23)14-7-5-4-6-8-14/h4-13H,1-3H3/t13-/m1/s1
2D structure diagram/image available?
Yes
General status
Pesticide type
Herbicide
Substance group
Aryaminopropionic acid
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Selective, systemic, absorbed by leaves
CAS RN
63782-90-1
EC number
-
CIPAC number
349
US EPA chemical code
-
PubChem CID
92366
Molecular mass
363.81
PIN (Preferred Identification Name)
isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate
IUPAC name
isopropyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate
CAS name
1-methylethyl N-benzoyl-N-(3-chloro-4-fluorophenyl)-D-alaninate
Other status information
-
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Z
Herbicide Resistance Classification (WSSA)
0
Insecticide Resistance Classification (IRAC)
Not applicable
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Avena fatua
Physical state
White crystals
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Barnon
Example products using this active
  • Cyanamid
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
12
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)
1560000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
147000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Ethanol
-
16000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane
-
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene
-
Melting point (°C)
73.5
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)
Not expected to self ignite; Not highly flammable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
4.90 X 1003 Calculated -
Log P
3.69
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
High
Bulk density (g ml⁻¹)
1.32
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)
8.50 X 10-02
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)
2.58 X 10-03
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
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)
55
S1 S = Expert judgement
1 = Estimated data with little or no verification
Moderately 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
- - -
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
- - -
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
-
W3 W = French database provided by ARVALIS-Institut du Végétal
3 = Unverified data of known source
Slightly mobile
Koc
750
Notes and range
Best available data
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
1.96 Calculated Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
7.45 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Slightly mobile Calculated -
Key metabolites
Metabolite
Formation medium
Estimated maximum occurrence fraction
1107/2009 relevancy
flamprop
Soil - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
120
P4 P = Other governments and regulators
4 = Verified data
Threshold for concern
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4000
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)
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
(ppm diet)
2.5 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
2000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Gallus gallus
Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 2.4
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 12
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Unknown species
Moderate
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)
6.8
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Unknown species
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)
- - -
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)
40
L1 L = Pesticide manuals and hard copy reference books / other sources
1 = Estimated data with little or no verification
Moderate
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)
1000
L1 L = Pesticide manuals and hard copy reference books / other sources
1 = Estimated data with little or no verification
Moderate
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)
> 4000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
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 II - -
Exposure Routes
Public
-
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
No data found
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
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
May cause skin damage if contact occurs
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H312
Environment: H400, H410
EC Risk Classification
N - Dangerous for the environment: R50/53
EC Safety Classification
S60, S61
WHO Classification
III (Slightly hazardous)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
flamprop-M-isopropyl
French
flamprop isopropyl r-(-)-isomere
German
Flamprop-M-isopropyl
Danish
flamprop-M-isopropyl
Italian
flamprop-isopropile R
Spanish
flamprop-M-isopropil
Greek
-
Polish
flamprop-M-izopropylu
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 23/01/2021
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