metalaxyl-M (Ref: CGA 329351) ** mefenoxam ** R-metalaxyl ** Translations

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GENERAL INFORMATION

Description: A fungicide used to control diseases caused by air- and soil-borne Peronosporales

Introduction: 1996, first reported & introduced USA

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

Status	Annex 1
Dossier rapporteur/co-rapporteur	Belgium
Date inclusion expires	31/12/2015

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:

Pesticide type	Fungicide
Substance group	Phenylamide
Substance origin	Synthetic
Mode of action	Systemic with curative and protective action
CAS RN	70630-17-0
EC number	-
CIPAC number	580
US EPA chemical code	-
Chemical formula	C15H21NO4
SMILES	O=C(N(c1c(cccc1C)C)[C@@H](C(=O)OC)C)COC
International Chemical Identifier (InChI)	InChI=1/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3/t12-/m1/s1
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	279.33
IUPAC Name	methyl N-(methoxyacetyl)-N-(2,6-xylyl)-D-alaninate
CAS Name	methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)-D-alaninate
Other status information	-
Herbicide Resistance Classification (HRAC)	Not applicable
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	4
Physical state	Colourless crystals
Related substances & organisms	chlorothalonil

Formulations:

Property	Value
Example manufacturers of products using this active	Fargro Syngenta Clayton
Example products using this active	Folio Fubol Gold SL567 Wakil XL
UK LERAP status	LERAP Category B (may vary across products)
Formulation and application details	Often supplied as a soluble concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		26000	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		59000	A5 - n-Hexane	-
		Miscible	A5 - Toluene	-
		Miscible	A5 - Methanol	-
		Miscible	A5 - Acetone	-
Melting Point (oC)		-38.7	L3	-
Boiling Point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		-	-	-
Flashpoint (oC)		179	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	5.13 X 1001	Calculated	-
	Log P	1.71	A5	Low
Bulk density (g ml-1)/Specific gravity		1.13	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 25oC (mPa)		3.3	A5	Volatile
Henry's law constant at 25oC (Pa m3 mol-1)		3.50 X 10-05	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		1.46 X 10-08	Calculated	Non-volatile
GUS leaching potential index		1.88	Calculated	Transition state
SCI-GROW groundwater index (µg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	6.44 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		266nm = 512, 274nm = 477, no absorption 290-750nm	A5	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	39	A5	Moderately persistent
	DT50 (lab at 20oC)	33	A5	Moderately persistent
	DT50 (field)	39	A4	Moderately persistent
	DT90 (lab at 20oC)	45	A5	-
	DT90 (field)	128	A5	-
	Note	EU dossier lab studies DT50 range 7-58 days, DT90 range 35.7-140 days, field study DT50 range 20-87 (USA), DT90 range 64.7-288.7 days
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	Stable
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	Very persistent
	Note	Stable at all pH values
Water-Sediment DT50 (days)		47.5	A5	Moderately fast
Water phase only DT50 (days)		47.5	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	3.85	A5	Slightly mobile
	Kfoc	660
	1/n	0.93
	Notes and range	EU dossier Kf range 0.1-7.6 mL/g, Kfoc range 20-1299 mL/g, 1/n range 0.69-1.12, Soils=5
pH sensitivity		Yes - relationship undefined in dossier

Key metabolites:

Metabolite		Formation Medium	Estimated Maximum Occurrence Fraction	91/414 Relevancy
N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine (Ref: CGA 62826)		Soil	0.404	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation Medium / Rate	Estimated Maximum Occurrence Fraction	Metabolising Enzymes
N-(2-hydroxymethyl-6-methylphenyl)-N-(methoxyacetyl)alanine Note: CAS 53823-88-4	-	-	-	-
N-(2,6-dimethyl- 5-hydroxyphenyl)-N-(methoxyacetyl)alanine methyl ester (Ref: CGA 100255) Note: CAS 96258-85-4	-	-	-	-
N-(2,6-dimethylphenyl)-N-(hydroxyacetyl)alanine (Ref: CGA 107955) Note: CAS 104390-55-8	-	Rat	-	-
N-(2-carboxy-6-methylphenyl)-N-(methoxyacetyl)alanine methyl ester (Ref: CGA 108905)	-	-	-	-
N-(2-carboxy-6-methylphenyl)-N-(methoxyacetyl)alanine (Ref: CGA 108906) Note: CAS: 104390-56-9; LC50(fish) = 100 mg l-1; LC50(Daphnia) = 100 mg l-1	-	Plant; Soil	-	-
N-(3-hydroxy-2,6-dimethylphenyl)-N-(methoxyacetyl)alanine (Ref: CGA 119857)	-	-	-	-
N-hydroxyacetyl-2,6-dimethyl-aniline (Ref: CGA 37734) Note: CAS 29183-14-0	-	-	-	-
N-(2,6-dimethylphenyl) alanine (Ref: CGA 67867)	-	-	-	-
N-methoxyacetyl-2,6-dimethyl-aniline (Ref: CGA 67868) Note: LC50(fish) = 98.9 mg l-1; LC50(Daphnia) = 158 mg l-1	-	Water	-	-
N-(2,6-dimethylphenyl)-N-(hydroxyacetyl)alanine methyl ester (Ref: CGA 67869) Note: CAS 66637-79-4	-	-	-	-
2,6-dimethylanilinoxoacetic acid (Ref: CGA 68124) Note: CAS 2903-48-2	-	-	-	-
N-(carboxycarbonyl)-N-(2,6-dimethylphenyl)alanine (Ref: CGA 78532)	-	-	-	-
N-(carboxycarbonyl)-N-(2,6-dimethylphenyl)alanine methyl ester (Ref: CGA 79353)	-	-	-	-
N-(2-hydroxymethyl-6-methylphenyl)-N-(methoxyacetyl)alanine methyl ester (Ref: CGA 94689) Note: CAS 85933-49-9	-	-	-	-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	15	A5	Low potential
	CT50 (days)	Not available		-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD50 (mg kg-1)		375	A4 Rat	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	2.5	L1 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		981	A5 Colinus virginianus	Moderate
Birds - Short term dietary (LC50/LD50)		> 5620 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		> 100	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		9.1	A4 Pimephales promelas	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 100	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		1.2	A4 Daphnia magna, as metalaxyl	-
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)		69.5	F3 Lemna gibba	Low
Algae - Acute 72 hour EC50, growth (mg l-1)		36	A4 Unknown species	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees - Acute 48 hour LD50 (µg bee-1)		> 127	A5 Oral	Low
Earthworms - Acute 14 day LC50 (mg kg-1)		830	A5	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	-14.5	Beneficial capacity Dose: 3.5 kg ha-1 A5 Aphidius rhopalosiphi, adult	Harmless
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	11.8	Beneficial capacity Dose: 2.5 kg ha-1, 5 applications at 14 day interval, 7 day A5 Typhlodromus pyri	Harmless
Soil micro-organisms		Nitrogen mineralisation: No significant effect Carbon mineralisation: No significant effect	A5 Dose: 6.6 mg/kg soil, 100 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		375	A4 Rat	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		2.29	A5 Rat (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.08	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.5	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.08	A5 Rat, 90 day, SF=100	-
Dermal penetration studies (%)		10	A5	-
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 identified]
Examples of European MRLs (mg kg-1)	Value	Table grapes and lettuce: 2.0; Wine grapes, pomes and cabbages: 1.0; Strawberries, citrus, sweet peppers, onions and garlic: 0.5; Carrots, cauliflower and broccoli: 0.1; Other vegetables and other fruit: 0.05; Cereal grains: 0.02
	Note	[Current May 2007.] [Limits include metalaxyl applying to sum of isomers/enantiomers.] For the EU pesticides database click here
Drinking Water MAC (µg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
		-				-
General human health issues		[No further information available]

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

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		[Not explosive or oxidising]
EC Risk Classification		[Xn - Harmful: R22], [Xi - Irritant: R41]
EC Safety Classification		S2, S26, S39, S46
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		-	-	-
UN Number		-
Waste disposal & packaging		-

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