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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
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)
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
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
35000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Dichloromethane
-
30
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Isopropanol
-
500
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
n-Hexane
-
3.5
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Toluene
-
Melting point (°C)
210
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Boiling point (°C)
Decomposes before boiling
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
-
Degradation point (°C)
210
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
2.40 X 1005 Calculated -
Log P
5.38
T4 T = UN EPFA database. Dataset no longer available.
4 = Verified data
High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.34
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
5.36
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Weak base
Vapour pressure at 20 °C (mPa)
1.17 X 10-04
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
7.00 X 10-02
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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)
27
W4 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available.
4 = Verified data
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
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Rapid
Note
Complete hydrolysis occurs in under 10 mins at pH 5, 7 and 9
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
Kd (mL g⁻¹)
-
W3 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available.
3 = Unverified data of known source
Non-mobile
Koc (mL g⁻¹)
4450
Notes and range
Best available data
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (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
J3 J = Pesticide Action Network database (click here )
3 = Unverified data of known source
High potential
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
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)
80
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr
-
(ppm diet)
5 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
144
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Apis mellifera
Low
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)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
Harmful
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
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
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
0.16
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Scenedesmus subspicatus
Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
80
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.02
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.003
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.02
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
-
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
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
XNo, known not to cause a problem
No data found
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
No data found
Eye irritant Phototoxicant  
Yes, known to cause a problem
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