Azocyclotin (Ref: BAY BUE 1452)

Azocyclotin (Ref: BAY BUE 1452)	Last updated: 25/09/2024
(Also known as: tricyclotin)

SUMMARY

Azocyclotin is an organotin acaricide which is 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.

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: Potential for particle bound transport: Medium Warning: Significant data are missing	Ecotoxicity High alert: Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Reproduction/development effects

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

Introduction & key dates

1978, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Italy

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

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

Chemical structure

Isomerism

None

Chemical formula

C₂₀H₃₅N₃Sn

Canonical SMILES

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

Isomeric SMILES

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 groups

Organometal acaricide; Organometal insecticide; Organotin acaricide; Organotin insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Contact action. Inhibits oxidative phosphorylation. Inhibitor of mitochondrial ATP synthase.

CAS RN

41083-11-8

EC number

255-209-1

CIPAC number

404

US EPA chemical code

484600

PubChem CID

91634

CLP index number

050-019-00-3

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

12B

Fungicide Resistance Class (FRAC MOA class)

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

AgroCare
King Tech Corp
Arysta LifeScience Corp
Bayer

Example products using this active

Caligur
Peropal

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)

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

2.40 X 10⁰⁵

Calculated

Log P

5.38

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.34

Dissociation constant pKa) at 25 °C

5.36

Weak base

Vapour pressure at 20 °C (mPa)

1.17 X 10^-04

Low volatility

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

7.00 X 10^-02

Non-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)

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 (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

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)

Sediment 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)

Non-mobile

K_oc (mL g⁻¹)

4450

Notes and range

Best available data

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

0.50

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

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

Bio-concentration factor

BCF (l kg⁻¹)

7500

High potential

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

cyhexatin (Ref: OMS 3029)

dicyclohexyltin oxide

cyclohexyltin acid

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

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

Plant; Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

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)

144

Coturnix japonica

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)

806

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)

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

Apis mellifera

Low

Chronic

Notes

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)

Harmful

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)

0.004

Oncorhynchus mykiss

High

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)

0.04

Daphnia magna

High

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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Aquatic plants (rooted, growth) - Acute 14 day EC₅₀, biomass (mg l⁻¹)

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

0.16

Scenedesmus subspicatus

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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

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

0.02

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

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

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

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

Exposure many cause gastric mucosa, haematological changes and hepatotoxicity

Handling issues

Property

Value and interpretation

General

Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

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

WHO Classification

II (Moderately hazardous)

UN Number

UN2786

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

azocyclotin

French

azocyclotin

German

Azocyclotin

Danish

azocyclotin

Italian

azociclotin

Spanish

azociclotin

Greek

Polish

azocyklocyna

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	25/09/2024
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