Amitraz (Ref: ENT 27967)

Amitraz (Ref: ENT 27967)	Last updated: 17/12/2020
(Also known as: amitraze; amitrazum ; BTS-27419; BAAM; U-36059)

SUMMARY

Amitraz is an amidine acaricide and insecticide that is currently not approved for use in the EU but is still used in some parts of the world. 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.

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

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

Also used in

Australia, USA

Chemical structure

Isomerism

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

No data

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 group

Amidine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic having contact and respiratory action. Octopaminergic (nervous system) agonist.

CAS RN

33089-61-1

EC number

251-375-4

CIPAC number

362

US EPA chemical code

106201

PubChem CID

36324

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

Cannot be used on horses

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

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

Physical state

Straw coloured crystalline solid

Related substances & organisms

bifenthrin

tralomethrin

Formulations

Property

Value

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

Mitac WP
Triazid
Amipaz
Zamir

Example products using this active

FCC
Agropharm
Kingtai Chemicals
Makhteshim

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)

Not expected to self ignite; Not highly flammable

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

3.16 X 10⁰⁵

Calculated

Log P

5.5

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

1000

Notes and range

Freundlich

K_f

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

semiamitraz hydrochloride (Ref: BTS-27271)

Soil

Major

2,4-dimethylformanilide (Ref: BTS 27919)

Soil

Minor

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2,4-dimethylaniline

Soil (Aerobic)

2,4-dimethylformanilide

Soil (Hydrolysis)

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

Soil (Aerobic)

2,4-dimethylbenzenamine

Soil (Aerobic)

N-(2,4-dimethylphenyl)formamide

Soil (Anaerobic)

2,4-dimethylbenzenamine

Soil (Anaerobic)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1838

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

800

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.74

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.00353

Pimephales promelas

High

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

0.035

Daphnia magna

High

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

0.002

Daphnia magna LOEC

High

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

4.7

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)

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

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

Non-target plants

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

Raphidocelis subcapitata

Low

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

Honeybees (Apis spp.)

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

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)

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 pollinators (1)

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

Mode of exposure

Other pollinators (2)

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

Mode of exposure

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

1000

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmful

[Dose: 360 g ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Moderately harmful

[Dose: 360 g l⁻¹]
Chrysoperla carnea

Soil micro-organisms

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

/ JMPR 1998

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

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

EC Risk Classification

Xn - Harmful: R22, R43, R48/22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S22, S24, S61, S36/37, S60

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

amitraz

French

amitraze

German

Amitraz

Danish

amitraz

Italian

amitraz

Spanish

amitraz

Greek

amitraz

Polish

amitraz

Swedish

Hungarian

amitraz

Dutch

amitraz

Record last updated:	17/12/2020
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