Azocyclotin (Ref: BAY BUE 1452)

Azocyclotin (Ref: BAY BUE 1452)	Last updated: 31/12/2020
(Also known as: tricyclotin)

SUMMARY

Azocyclotin is an organotin acaricide that is not approved for use in the EU and largely considered obsolete. It has a low aqueous solubility, is non-volatile and is not expected to leach to groundwater. Data is limited but is not expected to be persistent in soil systems but may be persistent in aquatic systems under certain conditions. It is highly toxic to mammals and also has a high potential to bioaccumulate. It is thought to be a skin, eye and respiratory system irritant. It is highly toxic to fish and aquatic invertebrates and moderately toxic to birds, honeybees and earthworms.

GENERAL INFORMATION

Description

An organotin acaricide used mainly for Phytophagous mite control

Example pests controlled

Mites including spider mites, citrus mites, bulb mites, tomato-russet mite

Example applications

Fruit including apples, pears, strawberries, grapes, citrus; Egg plant

Efficacy & activity

Availability status

Unknown

Introduction & key dates

1978

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

Italy

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

Nw Zealand; Chile; Australia; Morocco; South Africa; Iran; Lebanon

Chemical structure

Isomerism

Chemical formula

C₂₀H₃₅N₃Sn

Canonical SMILES

C1CCC(CC1)[Sn](C2CCCCC2)(C3CCCCC3)N4C=NC=N4

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ONHBDDJJTDTLIR-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/3C6H11.C2H2N3.Sn/c3*1-2-4-6-5-3-1;1-3-2-5-4-1;/h3*1H,2-6H2;1-2H;/q;;;-1;+1/rC20H35N3Sn/c1-4-10-18(11-5-1)24(23-17-21-16-22-23,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h16-20H,1-15H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Acaricide

Substance group

Organometal

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Contact action. Inhibits oxidative phosphorylation.

CAS RN

41083-11-8

EC number

255-209-1

CIPAC number

404

US EPA chemical code

PubChem CID

91634

Molecular mass

436.22

PIN (Preferred Identification Name)

1-(tricyclohexylstannyl)-1H-1,2,4-triazole

IUPAC name

tri(cyclohexyl)-1H-1,2,4-triazol-1-yltin

CAS name

1-(tricyclohexylstannyl)-1H-1,2,4-triazole

Other status information

Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

12B

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Tetranychus urticae

Physical state

Colourless crystalline powder

Formulations

Property

Value

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

Caligur
Peropal

Example products using this active

AgroCare
King Tech Corp
Arysta LifeScience Corp
Bayer

Formulation and application details

Usually supplied as a wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.04

Low

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

35000

Dichloromethane

Isopropanol

500

n-Hexane

3.5

Toluene

Melting point (°C)

210

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

210

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.40 X 10⁰⁵

Calculated

Log P

5.38

High

Bulk density (g ml⁻¹)

1.34

Dissociation constant pKa) at 25 °C

5.36

Weak base

Vapour pressure at 20 °C (mPa)

2.00 X 10^-08

Low volatility

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

7.00 X 10^-02

Non-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)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Rapid

Note

Complete hydrolysis occurs in under 10 mins at pH 5, 7 and 9

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

Non-mobile

K_oc

4450

Notes and range

Best available data

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

0.50

Calculated

Low leachability

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

Value

9.93 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

cyhexatin (Ref: OMS 3029)

Soil

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

dicyclohexyltin oxide

Soil

cyclohexyltin acid

Soil

1,2,4-triazole (Ref: CGA 71019)

Plant; Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

7500

High potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

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)

144

Coturnix japonica

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)

0.004

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.04

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

0.16

Scenedemus subspicatus

Moderate

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)

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)

100

Moderate

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)

806

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

Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

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)

Rat

High

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.02

Rat

Other Mammal toxicity endpoints

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

0.003

JMPR 2005

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

0.02

JMPR 2005

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

List I; List II

Exposure Routes

Public

Occupational

Occupational exposure may occur through inhalation of dust and dermal contact

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H301, H315, H318, H330, H335
Environment: H400, H410

EC Risk Classification

T+ - Very toxic: R26
T - Toxic: R25
Xn - Harmful: R41
Xi - Irritant: R37/38
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S26, S28, S45, S61, S36/37/39, S38, S60

WHO Classification

II (Moderately hazardous)

UN Number

2786

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

azocyclotin

French

azocyclotin

German

Azocyclotin

Danish

azocyclotin

Italian

azociclotin

Spanish

azociclotin

Greek

Polish

azocyklocyna

Swedish

Hungarian

Dutch

Record last updated:	31/12/2020
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