(Also known as: flamprop-M; CL 901444; AC 901444; L-flamprop-isopropyl)
SUMMARY
Flamprop-M-isopropyl is a discontinued herbicide. It has a moderate 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 health risks have been identified. It is moderately toxic to birds, most aquatic organisms, honeybees 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.
Environmental fate
Ecotoxicity
Human health
Environmental fate Moderate alert: GUS: Transition state; Drainflow: Slightly mobile; Potential for particle bound transport: Medium
A translocated, post-emergence arylalanine herbicide used to control wild-oats
Example pests controlled
Wild oats (Avena fatua)
Example applications
Wheat
Efficacy & activity
-
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
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
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
Australia
Chemical structure
Isomerism
Flamprop-M-isopropyl exhibits stereoisomerism, specifically due to the presence of a chiral centre in its alanine-derived structure. It is the stereospecific ester of the L-isomer of flamprop, meaning it is derived from the naturally occurring L-alanine configuration rather than the racemic mixture of D- and L-forms.
Example manufacturers & suppliers of products using this active now or historically
Cyanamid
Example products using this active
Barnon
Formulation and application details
Usually formulated into emulsifiable concentrates, often requiring oil-based adjuvants to enhance field performance
Commercial production
The commercial production of flamprop-M-isopropyl involves the synthesis of a stereospecific ester derived from L-alanine, ensuring herbicidal selectivity and potency. The process begins with the preparation of N-benzoyl-N-(3-chloro-4-fluorophenyl)-L-alanine, which is then esterified using isopropyl alcohol under controlled conditions to yield the desired isopropyl ester. This reaction typically requires acid catalysis and precise temperature regulation to maintain the integrity of the chiral centre.
Impact on climate of production and use
Data for the amount of life cycle GHGs produced by flamprop-M-isopropyl are not available in the public domain. However, whilst estimates vary, more general data suggests that between 18 and 27 kilograms of CO₂e is emitted per kilogram of herbicide produced.
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
Moderate
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)
-
-
-
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
Fat solubility of residues
Solubility
-
-
-
Data type
-
-
-
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; Chemspider; PubChem. (ChemID ) 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)
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 (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)
-
W3 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available. 3 = Unverified data of known source
Slightly mobile
Koc (mL g⁻¹)
750
Notes and range
Best available data
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
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
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
120
P4 P = Other non-EU, UK or US Governments and Regulators 4 = Verified data
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:
Human health
