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benalaxyl-M (Ref: IR 6141)
** kiralaxyl ** IR 6141 ** Translations

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

SUMMARY

Benalaxyl-M is a fungicide that has EU approval for use and is widely used. It has a low aqueous solubility and is quite volatile. Based on its chemical properties it would not be expected to leach to groundwater. It is moderately persistent in soil systems but may be persistent in water. It is moderately toxic to mammals, birds, most aquatic organisms, honey bees and earthworms.

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

Description: A common fungicide used to control fungal infections on a variety of crops

Example pests controlled: Downy mildew; Powdery mildew; Late blight; Grey mould

Example applications: Tomatoes; Potatoes; Grapes

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 2003

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Portugal
Date inclusion expires 30/04/2024
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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism Benalaxyl is a chiral molecule and benalxyl-M is the (-)-isomer of this substance.
Chemical formula C20H23NO3
Canonical SMILES CC1=C(C(=CC=C1)C)N(C(C)C(=O)OC)C(=O)CC2=CC=CC=C2
Isomeric SMILES CC1=C(C(=CC=C1)C)N([C@H](C)C(=O)OC)C(=O)CC2=CC=CC=C2
International Chemical Identifier key (InChIKey) CJPQIRJHIZUAQP-MRXNPFEDSA-N
International Chemical Identifier (InChI) InChI=1S/C20H23NO3/c1-14-9-8-10-15(2)19(14)21(16(3)20(23)24-4)18(22)13-17-11-6-5-7-12-17/h5-12,16H,13H2,1-4H3/t16-/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
Benalaxy 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 950
Known relevant impurities EU dossier : None declared
Substance origin Synthetic
Mode of action A systemic fungicide with protective, curative and eradication action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1.
CAS RN 98243-83-5
EC number -
CIPAC number 766
US EPA chemical code -
PubChem CID 176648
Molecular mass (g mol-1) 325.40
PIN (Preferred Identification Name) methyl N-(phenylacetyl)-N-(2,6-xylyl)-D-alaninate
IUPAC name methyl N-(phenylacetyl)-N-(2,6-xylyl)-D-alaninate
CAS name methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-D-alaninate
Other status information Potential groundwater pollutant
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 White crystalline solid
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
  • Isagro
Example products using this active
  • Kiralaxyl
UK LERAP status No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details -


ENVIRONMENTAL FATE

for benalaxyl-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) 33 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 17074 A5 - n-Heptane -
500000 A5 - Methanol -
500000 A5 - 1,2-Dichloromethane -
500000 A5 - Acetone -
Melting point (oC) 76 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 280 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 4.79 X 1003 Calculated -
Log P 3.68 A5 High
Bulk density (g ml-1)/Specific gravity 1.17 L3 -
Dissociation constant (pKa) at 25oC Not applicable - -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.0595 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.33 X 10-04 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 0.43 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 9.34 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 High
Maximum UV-vis absorption L mol-1 cm-1 Max at: 252.7nm; 258.6nm; 264.6nm & 274.1nm; No absorbance >290nm A5 -
Surface tension (mN m-1) 59.82 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) 80 L3 Moderately persistent
DT50 (lab at 20oC) 98.5 A5 Moderately persistent
DT50 (field) 44 A5 Moderately persistent
DT90 (lab at 20oC) 294 A5 -
DT90 (field) 178 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 49.0 to 207 days, DT90 range 148 to 484 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 Stable L3 -
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable L3 -
Note Stable pH 4 to pH 7, DT50 at pH 9: 301 days at 25 degC, 11 days at 50 degC
Water-sediment DT50 (days) 125 A5 Slow
Water phase only DT50 (days) 38 A5 Stable

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 - L3 Non-mobile
Koc 7175
Notes and range Koc range 2005-12346 mL/g 4 soils
Freundlich Kf 66.4 A5 Non-mobile
Kfoc 6063
1/n 0.98
Notes and range EU dossier Kf range 45.51-74.91, Kfoc range 2005-12346, 1/n range 0.92-1.04, soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
methyl N-(malonyl)-N-(2,6-xylyl)-Dalaninate This metabolite may cause environmental pollution, click here for further information Soil   0.241   Major fraction, Relevant
N-(malonyl)-N-(2,6-xylyl)-D-alanine This metabolite may cause environmental pollution, click here for further information Soil   0.285   Major fraction, Relevant
N-(phenylacteyl)-N-(2,6-xylyl)-D-alanine This metabolite may cause environmental pollution, click here for further information Soil   0.333   Major fraction, Relevant
2-((carboxyacetyl)((2R)-1-methoxy-1-oxo-2-propanyl)amino)-3-methylbenzoic acid Soil   -   -

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
Ethylene thiourea - - - -
methyl N-(formyl)-N-(2,6-xylyl)-DLalaninate
(Ref: B-F4)
- Groundwater - -
2-{(carboxyacetyl)[(1RS)-1-carboxyethyl]amino}-3-methylbenzoic acid
(Ref: B-F7)
- Groundwater - -
2-{(carboxyacetyl)[(2RS)-1-methoxy-1-oxo-2-propanyl]amino}-3-methylbenzoic acid
(Ref: B-F8)
- Groundwater - -
methyl N-(malonyl)-N-(2,6-xylyl)-DLalaninate
(Ref: B-M1)
- Groundwater - -
N-(malonyl)-N-(2,6-xylyl)-DL-alanine
(Ref: B-M2)
- Groundwater - -
methyl N-(formyl)-N-(2,6-xylyl)-Dalaninate
(Ref: R-isomer of B-F4)
- Groundwater - -
2-{(carboxyacetyl)[(1R)-1-carboxyethyl]amino}-3-methylbenzoic acid
(Ref: R-isomer of B-F7)
- Groundwater - -
2-{(carboxyacetyl)[(2R)-1-methoxy-1-oxo-2-propanyl]amino}-3-methylbenzoic acid
(Ref: R-isomer of B-F8)
- Groundwater - -


ECOTOXICOLOGY

for benalaxyl-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) 57 A5 Low potential
CT50 (days) 0.25 -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 4.4 L3 Rat, 2 year High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 775.2 mg kg-1 BW A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 4.9 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.49 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 22.8 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.2 A5 Daphnia magna 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) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 16.5 A5 Scenedemus subspicatus Low
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) > 100 A5 Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 104 A5 Low
Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) - - -
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) 236 A5 corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 26 A5 corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 172.2 >, Mortality
A5 Typhlodromus pyri
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 2745.6 >, Mortality
A5 Aphidius rhopalosiphi
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 1.65 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for benalaxyl-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) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 4.42 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.04 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) 0.06 A5 Rat, SF=100 -
Dermal penetration studies (%) 2.5-29% A5, Concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public Very low risk estimated
Occupational PPC/PPE advised
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Genotoxic Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

A3; B0; C3; D0; E2

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Possible liver toxicant
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: 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 oxidising or explosive
CLP classification 2013 Environment: H411
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R51/53
EC Safety Classification Click here to view information omn the EU safety phrases -
WHO Classification NL - Not listed
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for benalaxyl-M

Language Name
English benalaxyl-M
French benalaxil-M
German Benalaxyl-M
Danish benalaxyl-M
Italian benalaxil-M
Spanish benalaxil-M
Greek -
Slovenian benalaksil-M
Polish benalaksyl-M
Swedish -
Hungarian benalaxyl-M
Dutch -

Record last updated: Saturday 29 June 2019
Contact: aeru@herts.ac.uk