mecoprop-P (Ref: BAS 037H) ** CMPP-P ** MCPP-P ** mechlorprop-P ** RP 591066 ** Translations

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GENERAL INFORMATION
for mecoprop-P

Description: A herbicide for post-emergence control of broad-leaved weeds on grass

Example pests controlled: Cleavers; Chickweed; Clover; Plantains; Ground ivy; Knotweed; Bluegrasses; Bent grass

Example applications: Lawns; Sports fields; Golf courses; Fairways; Cereals including wheat, barley, oats, triticale

Efficacy & activity: Well established herbicide used across the Europe for broad leaved weed control for many years.

Availability status: Current

Introduction & key dates: 1987, Germany

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	UK/Ireland
Date inclusion expires	31/01/2019
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: Australia

Chemical structure:

Isomerism	Mecoprop-P is the herbicidally active D+ isomer of chiral mecoprop.
Chemical formula	C10H11ClO3
Canonical SMILES	CC1=C(C=CC(=C1)Cl)OC(C)C(=O)O
Isomeric SMILES	CC1=C(C=CC(=C1)Cl)O[C@H](C)C(=O)O
International Chemical Identifier key (InChIKey)	WNTGYJSOUMFZEP-SSDOTTSWSA-N
International Chemical Identifier (InChI)	InChI=1S/C10H11ClO3/c1-6-5-8(11)3-4-9(6)14-7(2)10(12)13/h3-5,7H,1-2H3,(H,12,13)/t7-/m1/s1
2D structure diagram/image available?	Yes

Cambridge Crystallographic Data Centre diagrams:

Common Name	Relationship	Link
Mecoprop	Unstated isomer

General status:

Pesticide type	Herbicide
Substance group	Aryloxyalkanoic acid
Minimum active substance purity	890 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Selective, systemic, absorbed through leaves and translocated to roots. Synthetic auxin.
CAS RN	16484-77-8
EC number	240-539-0
CIPAC number	475
US EPA chemical code	129046
PubChem CID	185588
Molecular mass (g mol-1)	214.65
PIN (Preferred Identification Name)	-
IUPAC name	(R)-2-(4-chloro-o-tolyloxy)propionic acid
CAS name	(2R)-2-(4-chloro-2-methylphenoxy)propanoic acid
Other status information	Potential groundwater contaminant
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	O
Herbicide Resistance Classification (WSSA)	4
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	-
Physical state	White to light brown crystalline solid
Related substances & organisms	bromoxynil carfentrazone-ethyl dicamba MCPA iron sulphate

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	BASF Belchim Certis Headland Nufarm Scotts
Example products using this active	Compitox Plus Di-Farmon R Foundation Optica Prompt Relay P
UK LERAP status	No approval for use
Formulation and application details	Often supplied as soluble concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE
for mecoprop-P

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		250000	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		1000000	A5 - Acetone	-
		1000000	A5 - Ethyl acetate	-
		1000000	A5 - Methanol	-
		314000	A5 - p-Xylene	-
Melting point (oC)		93.5	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		240	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	6.46 X 10-01	Calculated	-
	Log P	-0.19	A5	Low
Bulk density (g ml-1)/Specific gravity		1.31	A5	-
Dissociation constant (pKa) at 25oC		3.7	A5	-
		Note: Weak acid
Vapour pressure at 20oC (mPa)		0.23	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		5.70 X 10-05	A5	Non-volatile
GUS leaching potential index		1.60	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	4.41 X 10-03	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		Neutral soln: 229nm=9530, 280nm=1470, 285nm=1290, no absorption above 400nm; [Acid soln: 227nm=8860, 279nm=1340, 284 nm=1770, no absorption above 400nm; [Alkaline soln: 229nm=9520, 280nm=1560, 289nm=1360, no absorption above 400nm	A5	-
Surface tension (mN m-1)		50	A5 at 20 degC, 99.8%	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	5.24	A5	Non-persistent
	DT50 (lab at 20oC)	5.24	A5	Non-persistent
	DT50 (field)	21	H4	Non-persistent
	DT90 (lab at 20oC)	26	A5	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier lab studies DT50 range 4.0-8.2 days, DT90 range 23.1-33.6 days, Soils=3; Other field studies: DT50 5-17 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	44	A4	Stable
	Note	pH sensitive: DT50 42 days at pH 5, 44 days at pH 7, 32 days at pH 9 (for mecoprop)
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A4	-
	Note	Stable pH 5 to pH 9 at 25 & 70 degC
Water-sediment DT50 (days)		141	A5	Slow
Water phase only DT50 (days)		92	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	1.54	A5	Mobile
	Kfoc	59.8
	1/n	0.85
	Notes and range	EU 2016 RAR dossier Kf range 0.3-4.5 mL/g, Kfoc range 12-167 mL/g, 1/n range 0.66-1.01, Soils=10
pH sensitivity		Adsorption higher at lower pH

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
hydroxymethyl-mecoprop-P	HMCPP	Plant; Rat	-	-
carboxymecoprop-P	CCPP	Plant; Rat	-	-
o-cresol	2-methylphenol	Water (photolysis)	-	-

ECOTOXICOLOGY
for mecoprop-P

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	3	A5	Low potential
	CT50 (days)	1.1		-
Mammals - Acute oral LD50 (mg kg-1)		431	A5 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	> 20	A5 Mice	High
	(ppm diet)	> 100		-
Birds - Acute LD50 (mg kg-1)		500	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		> 5600 mg kg feed-1	A4 Unknown species	-
Fish - Acute 96 hour LC50 (mg l-1)		> 93	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		> 50	A5 Oncorhynchus mykiss	Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 91	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		22.7	A5 Daphnia magna	Low
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)		1.6	A5 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		16.2	A4 Unknown species	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		56	Q2 Unknown species	Low
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 988	A5	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	7.7	Mortality Fecundity Dose: 1.8 kg ha-1 A5 Aphidius rhopalosiphi	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	23	Mortality Dose: 1.064 g ha-1 A5 Carabus nemoralis	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 33.6 kg ha-1	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for mecoprop-P

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		431	A5 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 2.13	A5 Rat, 4 hr (whole body)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.01	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.04	A5 Rat, 90 day, SF=100	-
Dermal penetration studies (%)		1-10	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks to bystanders identified
	Occupational	No unacceptable risks to operators or other workers using PPE/PPC identified
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
General human health issues		Possible kidney & liver toxicant USEPA - some evidence to suggest possible human carcinogen

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Prevent generation of mists Not explosive or oxidising IMDG Transport Code is usually 9
CLP classification 2013		Health: H302, H318 Environment: H411
EC Risk Classification		Xn - Harmful: R22, R41 N - Dangerous for the environment: R51, R53
EC Safety Classification		S2, S13, S26, S37/39, S60, S61
WHO Classification		II	-	Moderately hazardous
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		Usually 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for mecoprop-P

Language	Name
English	mecoprop-P
French	mecoprop-P
German	Mecoprop-P
Danish	mechlorprop-P
Italian	mecoprop-P
Spanish	mecoprop-P
Greek	mecoprop-P
Slovenian	mekoprop-P
Polish	mekoprop-P
Swedish	mekoprop-P
Hungarian	mecoprop-P
Dutch	mecoprop-P

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Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk