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GET ADDITIONAL DATA HERE!

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

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for metalaxyl-M

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

Example pests controlled: Foliar and tuber blight; Downey mildews; Pseudoperonospora humuli; Phytophthora infestans ; Peronospora tabacina

Example applications: Potatoes; Tomatoes; Hops; Lettuce; Vegetables; Tobacco

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1996, first reported & introduced USA

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Belgium/Greece
Date inclusion expires 30/06/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Metalaxyl-M is the biologically active enantiomer (R-form) of the isomeric compound metalaxyl
Chemical formula C15H21NO4
Canonical SMILES CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)COC
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) ZQEIXNIJLIKNTD-GFCCVEGCSA-N
International Chemical Identifier (InChI) InChI=1S/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
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Metalaxyl Unstated isomer Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Phenylamide
Minimum active substance purity 910 g/kg
Known relevant impurities EU dossier - 2,6-dimethyl-phenylamine; 4-methoxy-5-methyl-5H-(1,2)oxathiole 2,2-dioxide; 1-methoxy-1-oxopropan-2-yl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate
Substance origin Synthetic
Mode of action Systemic with curative and protective action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1.
CAS RN 70630-17-0
EC number -
CIPAC number 580
US EPA chemical code -
PubChem CID 11150163
Molecular mass (g mol-1) 279.33
PIN (Preferred Identification Name) -
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 -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 4
Examples of recorded resistance -
Physical state Clear to pale yellow viscous liquid with weak odour at 97.2% purity, darkens with reducing purity
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • Fargro
  • Syngenta
  • Clayton
Example products using this active
  • Folio
  • Fubol Gold
  • SL567
  • Wakil XL
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details Often supplied as a soluble concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE
for metalaxyl-M

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
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 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 270 A5 -
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 20oC (mPa) 3.3 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 3.50 X 10-05 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.71 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 8.56 X 10-03 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the 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) 57.6 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 6.5 A5 Non-persistent
DT50 (lab at 20oC) 6.5 A5 Non-persistent
DT50 (field) 14.1 A5 Non-persistent
DT90 (lab at 20oC) 48.7 A5 -
DT90 (field) 46.7 A5 -
DT50 modelling endpoint - - -
Note EU dossier 2015 lab studies DT50 range 1.38-73.1 days, DT90 range 12.7-87.6 days, field studies DT50 range 9.3-30.9 days DT90 range 30.7-102.6 days
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value 10.8 R4 -
Note Published literature RL50 range 1.6-19.8 days, 6 field crops, various matrices, n=8
Aqueous photolysis DT50 (days) at pH 7 Value Stable A5 -
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable at all pH values
Water-sediment DT50 (days) 32.1 A5 Moderately fast
Water phase only DT50 (days) 24.8 A5 Slow

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd - - -
Koc -
Notes and range -
Freundlich Kf 1.63 A5 Moderately mobile
Kfoc 78.9
1/n 0.955
Notes and range EU dossier (2015) Kf range 0.07-8.01 mL/g, Kfoc range 20-284 mL/g, 1/n range 0.77-1.12, Soils=20
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alanine (Ref: CGA 62826 (racemate)) This metabolite may cause environmental pollution, click here for further information Soil   0.404   Major fraction, Not Relevant
(R)-2-((2,6-Dimethyl-phenyl)-(2-methoxy-acetyl)-amino)-propionic acid (Ref: NOA 409045) This metabolite may cause environmental pollution, click here for further information Soil   0.720   Major fraction; Relevant
N-(2,6-Dimethyl-phenyl)-2-methoxy-acetamide (Ref: CGA 67868) Soil   0.06   Minor fraction; Relevant
2-(((R)-1-Carboxy-ethyl)-(2-methoxy-acetyl)-amino)-3-methyl-benzoic acid (Ref: SYN 546520) Soil   0.04   Minor 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
for metalaxyl-M

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 15 A5 Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) 375 A5 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 Low
Fish - Chronic 21 day NOEC (mg l-1) 9.1 A4 Pimephales promelas Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 100 A5 Daphnia magna Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 1.2 A4 Daphnia magna, as metalaxyl Moderate
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
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 36 A4 Unknown species Low
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 97.3 A5 Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 830 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 35.63 A5 Eisenia foetida Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect -14.5 Beneficial capacity
Dose: 3.5 kg ha-1
A5 Aphidius rhopalosiphi, adult 		-
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 		-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect 		A5
Dose: 6.6 mg kg-1 soil, 100 days 		-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION
for metalaxyl-M

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) 375 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 2.29 A5 Rat, 4 hr (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 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
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
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 liver toxicant

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

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Health: H302, H318
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22, R41
EC Safety Classification Click here to view information omn the EU safety phrases S2, S26, S39, S46
WHO Classification NL - Not listed
US EPA Classification (formulation) - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS
for metalaxyl-M

Language Name
English metalaxyl-M
French metalaxyl-M
German Metalaxyl-M
Danish metalaxyl-M
Italian metalaxil-M
Spanish metalaxil-M; mefenoxam
Greek metalaxyl-M
Slovenian metalaksil-M
Polish metalaksyl-M
Swedish metalaxyl-M
Hungarian metalaxyl-M
Dutch methalaxyl-M

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