Benalaxyl (Ref: M 9834)

Benalaxyl (Ref: M 9834)	Last updated: 15/03/2024
(Also known as: benalaxil)

SUMMARY

Benalaxyl is a fungicide that is widely used but now being phased out in many countries. It has a low aqueous solubility, is quite volatile and a low potential for bioaccumulation. It is non-mobile, moderately persistent in soil systems but may be persistent in water systems. It is moderately toxic to mammals but would not be expected to bioaccumulate. It is moderately toxic to most aquatic organisms, honeybees and earthworms but less so to birds.

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 Moderate alert: Moderately persistent; GUS: Transition state; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

A phenylamide (acylalanine) fungicide used to control Oomycetes

Example pests controlled

Blue mould; Late blight; Downey mildew

Example applications

Tomatoes; Hops; Grapes; Lettuce; Peppers; Potatoes; Tobacco; Onions; Strawberries; Sunflowers; Soybeans; Turf; Ornamentals and flowers;

Efficacy & activity

Data supports good efficiacy. No adverse effects noted on treated crops.

Availability status

Current

Introduction & key dates

1981, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Romania/Portugal

Date EC 1107/2009 inclusion expires

Expired

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

Australia

Chemical structure

Isomerism

A chiral molecule existing in both the R- and S-forms

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

No data

International Chemical Identifier key (InChIKey)

CJPQIRJHIZUAQP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H6ClNO3S/c10-5-2-1-3-6-8(5)11(4-7(12)13)9(14)15-6/h1-3H,4H2,(H,12,13)

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

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protective, curative and eradicant action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1

CAS RN

71626-11-4

EC number

275-728-7

CIPAC number

416

US EPA chemical code

127001

PubChem CID

51369

CLP index number

No data found

Molecular mass

325.40

PIN (Preferred Identification Name)

methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate

IUPAC name

methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate

CAS name

methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alaninate

Other status information

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

Colourless solid

Related substances & organisms

benalaxyl acid

benalaxyl-M

Formulations

Property

Value

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

Interfarm
Sipcam
FCC Ltd
King Tech
ISAGRO S.p.A.
Farmoplant

Example products using this active

Galben M
Tairel

Formulation and application details

Available in a variety of formulations including suspension concentrates, granules, wettable powders and as a slurry for seed treatment.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

28.6

Low

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

19400

n-Heptane

250000

Methanol

250000

Acetone

250000

Ethyl acetate

Melting point (°C)

76.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

250

Flashpoint (°C)

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

3.47 X 10⁰³

Calculated

Log P

3.54

High

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.572

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

6.50 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

203nm, No absorption at 290nm

Surface tension (mN m⁻¹)

47.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

33.2

Moderately persistent

DT₅₀ (lab at 20 °C)

33.2

Moderately persistent

DT₅₀ (field)

66.8

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

222

DT₅₀ modelling endpoint

Note

EU RAR 2017: Lab studies DT₅₀ range 18.9-114 days, DT₉₀ range 60.2 days - >1 year, Soils=14; Field studies DT₅₀ range 26.6-127.6 days, DT₉₀ range 88.2-424 days, Soils=5

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

3.2

Note

Published literature RL₅₀ range 0.5-8.3 days, 5 field & undercover grown crops, various matrices, n=6

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

365

Very persistent

Note

Stable at pH 4 to pH 7, at pH 9 DT₅₀ = 157 days at 20 °C, 86 days at 25 °C, 55 days at 50 °C and < 1 day at 70 °C

Water-sediment DT₅₀ (days)

168.2

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)

71.0

Non-mobile

K_oc (mL g⁻¹)

4998

Notes and range

EU dossier K_d range 49.1-108 mL g⁻¹, K_oc range 2728-7173 mL g⁻¹, Soils=3

Freundlich

K_f (mL g⁻¹)

8.05

Slightly mobile

K_foc (mL g⁻¹)

555

¹/_n

0.630

Notes and range

EU RAR 2016: K_f range 7.77-8.33 mL g⁻¹, K_foc range 555-707 mL g⁻¹, ¹/_n range 0.630-0.714, Soils=2

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.29

Calculated

Transition state

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

Value

1.19 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

4.2

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)

Not available

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-DL-alaninate

Major fraction

0.234

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

Minor fraction

0.034

benalaxyl acid

Major fraction

0.101

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)

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

Not relevant

benalaxyl acid

Not relevant

2-[2-carboxy-N-(1-methoxy-1-oxopropan-2-yl)acetomido]-3-methylbenzoic acid

Not relevant

2-[2-carboxy-N-(1-methoxy-1-oxopropan-2-yl)acetomido]-3-methylbenzoic acid

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-(hydroxyphenylacetyl)-N-(2-hydroxymethylyl-6-methylphenyl)-alaninate

Rat

N-(phenylacetyle)-N-(2-carboxy-6-methylphenyl)-alaninate

Rat

methyl-N-malonyl-N-2,6-xylyl-DL-alaninate

BM-M7

Human; Surface water

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

BM-M3

Human; Rat; Surface water

methyl-N-(2,6-dimethylphenyl)-N-acetyl-DL-alaninate

Acetyl F4

Human

benalaxyl acid

Human; Rat; Plant; Surface water; Sediment

methyl N-(phenylacetyl)-N-(2-hydroxymethyl-6-methylphenyl)-alaninate

Rat

2-hydroxymethyl benalaxyl glucoside

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

680

Mouse

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

100

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

Birds - Acute LD₅₀ (mg kg⁻¹)

3700

Coturnix coturnix

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 ppm

Unknown species

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

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

180

Eisenia foetida

Moderate

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

36.4

Eisenia foetida

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)

31.25

Folsomia candida

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)

> 22.6

Apis mellifera

Moderate

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

> 3.61

Apis mellifera

Bumblebees (Bombus spp.)

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

> 100

Bombus terrestris 48 hr

Low

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

> 35.46

Bombus terrestris 48 hr

Moderate

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)

Harmless to 6 kg ha⁻¹

Chrysoperla carnea Larva

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

61.5

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at 1 DA4T

as LR₅₀ g ha⁻¹ 75.3

Typhlodromus pyri Adult

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)

3.75

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)

0.59

Daphnia magna

Moderate

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

0.03

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)

3.13

Chironomus riparius

Moderate

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)

2.4

Selenastrum capricornutum

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

680

Mouse

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

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

0.5

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

None allocated

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

0.05

Dermal penetration studies (%)

0.7-18

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk of dietary exposure

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Extensive metabolism, excretion >95% within 72 hrs, mainly via faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive
A weak oxidising agent
Not expected to auto-ignite; Not highly flammable
IMDG Transport \hazard Class 9

CLP classification 2013

Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

benalaxyl

French

benalaxil

German

Benalaxyl

Danish

benalaxyl

Italian

benalaxil

Spanish

benalaxil

Greek

benalaxyl

Polish

benalaksyl

Swedish

Hungarian

benalaxyl

Dutch

benalaxyl

Norwegian

Record last updated:	15/03/2024
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