| azocyclotin (Ref: BAY BUE 1452) |
 |
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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 
for azocyclotin
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
Availability status: Unknown
Introduction & key dates: 1978
EC Regulation 1107/2009 (repealing 91/414):
| Status | Not approved |
| Dossier rapporteur/co-rapporteur | Italy |
| Date inclusion expires | Expired |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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Also used in: Nw Zealand; Chile; Australia; Morocco; South Africa; Iran; Lebanon
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 | - | |||
| Chiral molecule | No | |||
| Chemical formula | C20H35N3Sn | |||
| SMILES | [n-]1ncnc1.[Sn+](C1CCCCC1)(C2CCCCC2)C3CCCCC3 | |||
| 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 | |||
| Structure diagram/image available? | Yes | |||
| Molecular mass (g mol-1) | 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 | |||
| 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 | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use or outside scope | |||
| Formulation and application details | Usually supplied as a wettable powder. | |||
ENVIRONMENTAL FATE
for azocyclotin
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.04 | F3 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 35000 | L3 - Dichloromethane | - | |
| 30 | L2 - Isopropanol | - | ||
| 500 | L2 - n-Hexane | - | ||
| 3.5 | L2 - Toluene | - | ||
| Melting point (oC) | 210 | L3 | - | |
| Boiling point (oC) | Decomposes before boiling | V3 | - | |
| Degradation point (oC) | 210 | L3 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | V3 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.40 X 1005 | Calculated | - |
| Log P | 5.38 | T4 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.34 | L3 | - | |
| Dissociation constant (pKa) at 25oC | 5.36 | L3 | - | |
| Note: Weak base | ||||
| Vapour pressure at 25oC (mPa) | 2.00 X 10-08 | L3 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 7.00 X 10-02 | L3 | Non-volatile | |
| Henry's law constant at 20oC (dimensionless) | 8.80 X 10-04 | Q2 | Volatile | |
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 |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | - | - | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Soil degradation (days) (aerobic) | DT50 (typical) | 27 | W4 | Non-persistent |
| DT50 (lab at 20oC) | - | - | - | |
| DT50 (field) | - | - | - | |
| DT90 (lab at 20oC) | - | - | - | |
| DT90 (field) | - | - | - | |
| Note | Best available data | |||
| Plant matrix DT50 (days) | Value | - | - | - |
| Note | - | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | - | - | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Rapid | F3 | - |
| 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/Other Information |
Interpretation |
|
| Linear | Kd | - | W3 | Non-mobile |
| Koc | 4450 | |||
| Notes and range | Best available data | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | - | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 91/414 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) Note: - |
- | Plant; Animal | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 7500 | J3 | High potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 80 | F4 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | L2 Rat, 2 year | - |
| (ppm diet) | 5 | - | ||
| Birds - Acute LD50 (mg kg-1) | 144 | L3 Coturnix japonica | Moderate | |
| Birds - Short term dietary (LC50/LD50) | - | - | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.004 | L3 Oncorhynchus mykiss | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | - | - | - | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.04 | L3 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 | L3 Scenedemus subspicatus | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | 100 | L3 | Moderate | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 806 | L3 | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | Harmful | AB1 Typhlodromus pyri | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | - | - | - | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for azocyclotin
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | 80 | F4 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | L3 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.02 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.003 | JMPR 2005 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.02 | JMPR 2005 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | - | - | - | |
| Dermal penetration studies (%) | - | - | - | |
| Dangerous Substances Directive 76/464 | List I; List II | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | - | ||
| Occupational | Occupational exposure may occur through inhalation of dust and dermal contact | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
- |
- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | No further information available | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
No information available | |||
| CLP classification 2013 | Health: H301, H315, H318, H330, H335 Environment: H400, H410 |
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| EC Risk Classification |
T+ - Very toxic: R26 T - Toxic: R25 Xn - Harmful: R41 Xi - Irritant: R37/38 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S26, S28, S45, S61, S36/37/39, S38, S60 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | I | - | Danger - Highly toxic | |
| UN Number | 2786 | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | azocyclotin |
| French | azocyclotin |
| German | Azocyclotin |
| Danish | azocyclotin |
| Italian | azociclotin |
| Spanish | azociclotin |
| Greek | - |
| Slovenian | azociklotin |
| Polish | azocyklocyna |
| Swedish | - |
| Hungarian | - |
| Dutch | - |
Record last updated: Tuesday 01 March 2016
Contact: aeru@herts.ac.uk