Aminopyralid (Ref: XDE 750)

Aminopyralid (Ref: XDE 750)	Last updated: 22/08/2024
(Also known as: 4-amino-3,6-dichloropicolinic acid; DE 750; XR 750; GF 839)

SUMMARY

Aminopyralid is a pyridine carboxylic acid herbicide. It is non-volatile, highly soluble in water and, based on its chemical properties, is mobile and has a high potential for leaching to groundwater. It may be moderately persistent in soil systems but would not be expected to persistent in surface water under normal conditions. It has a low mammalian toxicity and there is some concern regarding its potential for bioaccumulation. Aminopyralid has a low to moderate toxicity to most terrestrial and aquatic species.

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: GUS: High leachability; Drainflow: Very mobile	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate	Human health Moderate alert: Genotoxic

GENERAL INFORMATION

Description

A pyridine carboxylic acid herbicide for the long-term control of noxious and invasive broad-leaved weeds in grassland

Example pests controlled

Broomweed; Buttercups; Cocklebur; Daisy; Fleabane; Knapweed; Ragweed; Ragwort; Lambsquarter

Example applications

Rangeland; Permanent grass; Non-cropped areas including paths; roadways

Efficacy & activity

Availability status

Current

Introduction & key dates

2005, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Finland/Denmark

Date EC 1107/2009 inclusion expires

31/12/2024

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, USA, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₆H₄Cl₂N₂O₂

Canonical SMILES

C1=C(C(=C(N=C1Cl)C(=O)O)Cl)N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NIXXQNOQHKNPEJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H4Cl2N2O2/c7-3-1-2(9)4(8)5(10-3)6(11)12/h1H,(H2,9,10)(H,11,12)/f/h11H,9H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Pyridine herbicide; Picolinic acid herbicide

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, post-emergence action, absorbed by leaves and roots, some residual action

CAS RN

150114-71-9

EC number

604-721-7

CIPAC number

771

US EPA chemical code

005100

PubChem CID

213012

CLP index number

No data found

Molecular mass

207.03

PIN (Preferred Identification Name)

4-amino-3,6-dichloropyridine-2-carboxylic acid

IUPAC name

4-amino-3,6-dichloropyridine-2-carboxylic acid

CAS name

4-amino-3,6-dichloro-2-pyridinecarboxylic acid

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

Off-white powder

Related substances & organisms

aminopyralid-dimethylammonium

aminopyralid-potassium

aminopyralid-tripromine

Formulations

Property

Value

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

Dow Agrosciences

Example products using this active

CleanWave
Forefront
Pharoah
Milestone
Banish
Lancelot

Formulation and application details

Often available as an oil in water concentrate that is mixed with water and used as a spray.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2480

High

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

29200

Acetone

3940

Ethyl acetate

52200

Methanol

Xylene

Melting point (°C)

163.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

334

Flashpoint (°C)

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

1.35 X 10^-03

Calculated

Log P

-2.87

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.76

Dissociation constant pKa) at 25 °C

2.56

Strong acid

Vapour pressure at 20 °C (mPa)

2.59 X 10^-05

Low volatility

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

9.61 X 10^-12

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

24 hr

From soil surface

2.6

24 hr

Volatilisation is not considered critical for air pollution

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

At pH 1.4 maxima = 217nm
At pH 5 maxima = 217nm
At pH 12.6 maxima = 220nm

Surface tension (mN m⁻¹)

71.0

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)

55.5

Moderately persistent

DT₅₀ (field)

12.1

Non-persistent

DT₉₀ (lab at 20 °C)

185

Persistent

DT₉₀ (field)

40.2

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 26.4-146.9 days, DT₉₀ range 87.6-488 days, field studies DT₅₀ range 3.75-21.6 days, DT₉₀ range 12.5-71.8 days; Manufacturer lab data DT₅₀ 9-54 days; Other literature Lab studies range 31.5-533.2 days, 5 soils

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

0.6

Fast

Note

DT₅₀: 0.6 days at pH 5. Main route of degradation on aquatic environments

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

Value

Stable

Note

Stable pH 5 to pH 9 at temps 20 and 50 °C

Water-sediment DT₅₀ (days)

712

Stable

Water phase only DT₅₀ (days)

250

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

0.17

Very mobile

K_foc (mL g⁻¹)

8.3

¹/_n

0.852

Notes and range

EU dossier K_f range 0.01-0.73 mL g⁻¹, K_foc range 0.31-21.7 mL g⁻¹, ¹/_n range 0.32-1.52, Soils=8

pH sensitivity

Adsorption higher at low pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.34

Calculated

High leachability

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

Value

1.60 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Very mobile

Calculated

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

153.6

Calculated using the Atkinson method, 12 hr

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

100

Threshold for concern

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 465

Rat

Moderate

(ppm diet)

> 1000

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

1000

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

185.6

Unknown species

Moderate

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

> 1000

Eisenia foetida

Low

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

Soil micro-organisms

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

Dose: 100x field rate for grassland

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)

> 6.26

Apis mellifera

Moderate

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

> 3.13

Apis mellifera

Moderate

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) as % Mortality at dose at 8.3 g ha⁻¹

11.76

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as % Mortality at dose 0.03 kg ha⁻¹

21.46

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at dose 0.08 kg ha⁻¹

12.6

Typhlodromus pyri Protonymph

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)

> 100

Oncorhynchus mykiss

Low

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

1.3

Pimephales promelas

Moderate

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

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

> 100

Daphnia magna

Low

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

100

Daphnia magna

Low

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

100

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

130

Chironomus riparius

Low

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

46.7

Chironomus riparius

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Lemna gibba

Low

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

Pseudokirchneriella subcapitata

Low

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.5

Rat 4 hr

Other Mammal toxicity endpoints

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

0.26

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

0.26

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

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

0.26

Dermal penetration studies (%)

UK ACP

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk to bystanders

Occupational

Acceptable risk to operators with PPE/PPC
Low risk to other farm workers

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

EU MRL levels for some commodities subject to change in mid-2022

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=4260 µg l⁻¹

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

May damage the corneal resulting in permanent impairment of vision and blindness

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable
Corrosive

CLP classification 2013

Health: H315, H318, H319, H335
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

aminopyralid

French

aminopyralid

German

Aminopyralid

Danish

aminopyralid

Italian

aminopyralid

Spanish

aminopiralida

Greek

Polish

aminopiralid

Swedish

aminopyralid

Hungarian

Dutch

Norwegian

aminopyralid

Record last updated:	22/08/2024
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