Bilanafos (Ref: MW 801)

Bilanafos (Ref: MW 801)	Last updated: 23/05/2024
(Also known as: AIDS 132579; bialaphos; SF 1293; bilanaphos; bialafos)

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
	Ecotoxicity Low alert: Birds acute ecotoxicity: Low; Fish acute ecotoxicity: Low; Daphnia acute ecotoxicity: Low; Earthworms acute ecotoxicity: Low	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A naturally occurring peptide herbicide used to control various annual and perennial crops

Example pests controlled

Annual and perennial weeds

Example applications

Grapes: Apples; Citrus

Efficacy & activity

Appearance and life cycle

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

1984, introduced

Taxonomic classification

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

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

Known to be also used in the following countries

Chemical structure

Isomerism

Bilanafos is a chiral molecule.

Chemical formula

C₁₁H₂₂N₃O₆P

Canonical SMILES

CC(C(=O)NC(C)C(=O)O)NC(=O)C(CCP(=O)(C)O)N

Isomeric SMILES

C[C@@H](C(=O)N[C@@H](C)C(=O)O)NC(=O)[C@H](CCP(=O)(C)O)N

International Chemical Identifier key (InChIKey)

GINJFDRNADDBIN-FXQIFTODSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H22N3O6P/c1-6(9(15)14-7(2)11(17)18)13-10(16)8(12)4-5-21(3,19)20/h6-8H,4-5,12H2,1-3H3,(H,13,16)(H,14,15)(H,17,18)(H,19,20)/t6-,7-,8-/m0/s1

2D structure diagram/image available?

Yes

General status

Biopesticide type

Herbicide

Substance groups

Micro-organism derived substance; Peptide herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Pro-toxin. Non-selective, systemic, contact action. Glutamine synthetase inhibitor: accumulates ammonium ions, inhibits photosynthesis.

Substance source

Isolated from the soil bacterium Streptomyces hygroscopicus (Jensen) Waksman & Henrici and Streptomyces viridochromeogenes (Krainsky) Waksman & Henrici, It is a protoxin, degrading to glufosinate in the plant.

Substance production

Produced by controlled fermentation usually as the sodium salt

Uses

Crop protection

Target pests

A wide range of post-emergence annual and perennial broad-leaved weeds

Target host

Grapes: Apples; Citrus

Farming system suitability

CAS RN

35597-43-4

EC number

CIPAC number

None allocated

US EPA chemical code

PubChem CID

5462314

Molecular mass

323.28

PIN (Preferred Identification Name)

IUPAC name

(2S)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyryl-L-alanyl-L-alanine

CAS name

(2S)-2-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-alanine

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Solid

Formulations

Property

Product

Manufacturer

Example products

Formulation and application details

Usually suplied as a soluble powder or as liquid formulations

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1000

High

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

250000

Ethanol

500000

Methanol

Melting point (°C)

160

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

8.71 X 10^-03

Calculated

Log P

-2.06

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

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

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

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

Not pH sensitive

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

4-[(hydroxy)(methyl)phosphinyl]butyric acid

Mice (Faeces)

glufosinate (Ref: HOE 00661)

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

268

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5000

Gallus domesticus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

> 1000

Non-toxic

Low

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

Soil micro-organisms

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)

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

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)

Beneficial insects (Predatory mites)

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)

> 1000

Cyprinus carpio

Low

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

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

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

> 5000

Daphnia magna

Low

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

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)

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

268

Rat

Moderate

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

3000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.57

Rat

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 80 mg kg⁻¹

Mouse

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

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

Eye irritant

Phototoxicant

No data found

General human health issues

No adverse health effects noted

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H301, H302, H312, H315, H319, H332, H335, H361, H370

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bilanafos

French

German

Danish

bilanafos

Italian

bilanafos

Spanish

bilanafos

Greek

Polish

bilanafos

Swedish

bilanafos

Hungarian

Dutch

bilanafos

Norwegian

Record last updated:	23/05/2024
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