Benalaxyl-M (Ref: IR 6141)

Benalaxyl-M (Ref: IR 6141)	Last updated: 17/05/2024
(Also known as: kiralaxyl; IR 6141)

SUMMARY

Benalaxyl-M is a fungicide that 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, honeybees and earthworms.

Data 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.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Potential for particle bound transport: High	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Genotoxic; Reproduction/development effects

GENERAL INFORMATION

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, introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2025

UK LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Portugal

Date EC 1107/2009 inclusion expires

30/04/2025

EU Candidate for substitution (CfS)

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

Chemical structure

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

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
Benalaxyl	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Acylamino acid fungicide; Anilide fungicide; Aromatic amide fungicide

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

619-330-7

CIPAC number

766

US EPA chemical code

Not listed

PubChem CID

176648

CLP index number

No data found

Molecular mass

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White crystalline solid

Related substances & organisms

benalaxyl acid

benalaxyl

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Isagro

Example products using this active

Kiralaxyl

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

17074

n-Heptane

500000

Methanol

500000

1,2-Dichloromethane

500000

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

280

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

4.79 X 10⁰³

Calculated

Log P

3.68

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.17

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.0595

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

2.33 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Max at: 252.7nm; 258.6nm; 264.6nm & 274.1nm; No absorbance >290nm

Surface tension (mN m⁻¹)

59.82

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

98.5

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

294

Persistent

DT₉₀ (field)

178

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 49.0 to 207 days, DT₉₀ range 148 to 484 days

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

Stable

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 4 to pH 7, DT₅₀ at pH 9: 301 days at 25 °C, 11 days at 50 °C

Water-sediment DT₅₀ (days)

125

Slow

Water phase only DT₅₀ (days)

Stable

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

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

7175

Notes and range

K_oc range 2005-12346 mL g⁻¹ 4 soils

Freundlich

K_f (mL g⁻¹)

66.4

Non-mobile

K_foc (mL g⁻¹)

6063

¹/_n

0.98

Notes and range

EU dossier K_f range 45.51-74.91, K_foc range 2005-12346, ¹/_n range 0.92-1.04, soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.36

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

8.32 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

4.17

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

0.25

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

methyl N-(malonyl)-N-(2,6-xylyl)-D-alaninate

Major fraction

0.241

N-(malonyl)-N-(2,6-xylyl)-D-alanine

Major fraction

0.285

N-(phenylacteyl)-N-(2,6-xylyl)-D-alanine

Major fraction

0.333

2-((carboxyacetyl)((2R)-1-methoxy-1-oxo-2-propanyl)amino)-3-methylbenzoic acid

Minor fraction

0.072

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2-{(carboxyacetyl)[(1RS)-1-carboxyethyl]amino}-3-methylbenzoic acid

Not relevant

2-{(carboxyacetyl)[(2RS)-1-methoxy-1-oxo-2-propanyl]amino}-3-methylbenzoic acid

Not relevant

Ethylene thiourea

Not relevant

methyl N-(malonyl)-N-(2,6-xylyl)-D-alaninate

Not relevant

N-(malonyl)-N-(2,6-xylyl)-DL-alanine

Not relevant

2-((carboxyacetyl)((2R)-1-methoxy-1-oxo-2-propanyl)amino)-3-methylbenzoic acid

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-(malonyl)-N-(2,6-xylyl)-D-alanine

Surface water; Sediment

methyl N-(malonyl)-N-(2,6-xylyl)-D-alaninate

Surface water; Sediment

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

4.4

Rat 2 yr

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 775.2 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

236

Eisenia foetida corr

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 1.65 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 104

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 2745.6

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 172.2

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

4.9

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.49

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

22.8

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.2

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

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)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

16.5

Scenedesmus subspicatus

Low

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.42

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.04

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.06

Rat SF=100

Dermal penetration studies (%)

2.5-29%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Very low risk estimated

Occupational

PPC/PPE advised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H411

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

benalaxyl-M

French

benalaxil-M

German

Benalaxyl-M

Danish

benalaxyl-M

Italian

benalaxil-M

Spanish

benalaxil-M

Greek

Polish

benalaksyl-M

Swedish

Hungarian

benalaxyl-M

Dutch

Norwegian

Record last updated:	17/05/2024
Contact:	aeru@herts.ac.uk
Please cite as:	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