Amitraz (Ref: ENT 27967)

Amitraz (Ref: ENT 27967)	Last updated: 22/08/2024
(Also known as: amitraze; amitrazum ; BTS 27419; BAAM; U-36059)

SUMMARY

Amitraz is an amidine acaricide and insecticide. It is volatile, almost insoluble in water and, based on its chemical properties, is only slightly mobile with a low potential for leaching to groundwater. It is not persistent in soil systems, degradation being very rapid and would also not be expected to persistent in surface water under normal conditions. Amitraz has a moderate mammalian toxicity and there is some concern regarding its potential for bioaccumulation. It is considered to be a neurotoxin. Amitraz has a high to moderate toxicity to most terrestrial and aquatic species, the main exception being algae for which amitraz has a low level of toxicity.

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: Drainflow: Slightly mobile	Ecotoxicity High alert: Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Neurotoxicant

GENERAL INFORMATION

Description

An amidine acaricide and insecticide for use in top fruit, ornamentals and some vegetables. Also has veterinary treatment applications.

Example pests controlled

Bollworm; Budworm; Red spider mites; Leaf miners; Scale insects; Aphids; Ticks; Psyllids; Varroa mite

Example applications

Fruit including apples, pears and plums; Ornamentals; Some vegetables; Cotton; Livestock; Bees

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1972, introduced

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Austria

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, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₉H₂₃N₃

Canonical SMILES

CC1=CC(=C(C=C1)N=CN(C)C=NC2=C(C=C(C=C2)C)C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

QXAITBQSYVNQDR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
amitraz	-

General status

Pesticide type

Insecticide, Acaricide, Veterinary substance

Substance groups

Amidine insecticide; Formamidine insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic having contact and respiratory action. Acts on nervous system. Octopamine receptor agonist.

CAS RN

33089-61-1

EC number

251-375-4

CIPAC number

362

US EPA chemical code

106201

PubChem CID

36324

CLP index number

612-086-00-2

Molecular mass

293.41

PIN (Preferred Identification Name)

N'-(2,4-dimethylphenyl)-N-{[(2,4-dimethylphenyl)imino]methyl}-N-methylmethanimidamide

IUPAC name

N,N'-[(methylimino)dimethylidyne]di-2,4-xylidine

CAS name

N'-(2,4-dimethylphenyl)-N-[[(2,4-dimethylphenyl)imino]methyl]-N-methylmethanimidamide

Other status information

PAN Bad Actor Chemical; Cannot be used on horses

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)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Panonychus citri, Tetranychus cinnabarinus, Tetranychus urticae, Boophilus microplus, Cacopsylla pyri

Physical state

Straw coloured crystalline solid

Formulations

Property

Value

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

FCC
Agropharm
Kingtai Chemicals
Makhteshim

Example products using this active

Mitac WP
Triazid
Amipaz
Zamir

Formulation and application details

Usually supplied as emulsifiable concentrates or wettable powders for crop use and solutions for livestock topical administration

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.1

Low

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

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

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

3.16 X 10⁰⁵

Calculated

Log P

5.5

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.13

Dissociation constant pKa) at 25 °C

9.8

Weak acid

Vapour pressure at 20 °C (mPa)

0.051

Low volatility

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

1.06

Moderately volatile

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)

0.2

Non-persistent

DT₅₀ (lab at 20 °C)

0.2

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Literature DT₅₀ studies range 0.1-2 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.2

Note

Published literature RL₅₀ range 5.0-7.3 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Stable in UV light

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ 2hrs at pH 5, 1.1 days at pH 9, rapid hydrolysis

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)

Slightly mobile

K_oc (mL g⁻¹)

1000

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.00

Calculated

Low leachability

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

Value

1.92 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

1838

Threshold for concern

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

N'-(2,4-dimethylphenyl)-N-methyl-methanimidamide

Minor fraction

Aerobic

N-(2,4-dimethylphenyl)formamide

Minor fraction

Anaerobic

semiamitraz hydrochloride (Ref: BTS-27271)

Major fraction

2,4-dimethylformanilide (Ref: BTS 27919)

Minor fraction

2,4-dimethylbenzenamine

Minor fraction

Anaerobic

2,4-dimethylaniline

Minor fraction

Aerobic

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

800

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

788

Colinus virginianus

Moderate

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

Moderate

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)

Apis mellifera

Moderate

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)

Moderately harmful at dose 360 g ha⁻¹

Chrysoperla carnea

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Harmful at dose 360 g ha⁻¹

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)

0.74

Oncorhynchus mykiss

Moderate

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

> 0.00353

Pimephales promelas

High

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

4.25

Danio rerio

Moderate

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

0.035

Daphnia magna

High

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

0.002

Daphnia magna LOEC

High

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

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

4.7

Americamysis bahia

Moderate

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

> 8.0

Chironomus riparius 48 hr

Moderate

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)

Raphidocelis subcapitata

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)

800

Rat

Moderate

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

200

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

65.0

Rat

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 800 mg kg⁻¹

Rat

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

0.003

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

0.01

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

Occupational exposure may occur through inhalation and dermal contact

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

In mammals urine is the major route of excretion. 55-74% of the dose was excreted after dosing within first 24hrs

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Ingestion may cause slow heart beat, low blood pressure, sedation and low body temperature
US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H317, H373
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

amitraz

French

amitraze

German

Amitraz

Danish

amitraz

Italian

amitraz

Spanish

amitraz

Greek

amitraz

Polish

amitraz

Swedish

Hungarian

amitraz

Dutch

amitraz

Norwegian

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