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Azocyclotin

HCID 91634
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Basic information

CAS
41083-11-8
Standard SMILES
c1nc[n]([Sn]([CH]2CCCCC2)([CH]2CCCCC2)[CH]2CCCCC2)n1
InChIKey
ONHBDDJJTDTLIR-UHFFFAOYSA-N
Molecular formula
C20H35N3Sn
Average molar mass
436.2 g/mol
Monoisotopic mass
437.185301

Overview

Azocyclotin is a member of the class of triazoles that is 1,2,4-triazole substituted at position 1 by a tricyclohexylstannyl group. It is a member of triazoles and an organotin acaricide.

Names & identifiers

Preferred name
Azocyclotin
IUPAC
tricyclohexyl(1,2,4-triazol-1-yl)stannane
English name
Azocyclotin
Molecular formula
C20H35N3Sn
Molecular weight
436.22

Names & synonyms

Azocyclotin41083-11-8Peropal1-(Tricyclohexylstannyl)-1H-1,2,4-triazoleBAY bue 1452(1H-1,2,4-Triazolyl)tricyclohexylstannaneTri(cyclohexyl)-1H-1,2,4-triazol-1-yltinV4YRQ367KECHEBI:2959DTXSID2058091(1H-1,2,4-triazol-1-yl)tricyclohexylstannaneRefChem:116141
Show more names
ClermaitTriclotintriclotainbaybue1452PEROPAL(R)CLERMAIT(R)CLAIRMAIT(R)
DTXCID4031859255-209-1685-653-5tricyclohexyl(1,2,4-triazol-1-yl)stannane1H-1,2,4-Triazole, 1-(tricyclohexylstannyl)-Tri(cyklohexyl)-1H-1,2,4-triazol-1-ylstanniumStannane, (1H-1,2,4-triazol-1-yl)tricyclohexyl-Tricyclotin

Database identifiers

CAS
41083-11-8
PubChem CID
91634
DTXSID
DTXSID2058091
ChEBI
CHEBI:2959
UNII
V4YRQ367KE
EC Number
255-209-1、685-653-5

Properties

Computed structural properties

Topological polar surface area
30.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
24
Formal charge
0
Complexity
339

Experimental & physicochemical properties

Chemical ClassesMetals -> Tin Compounds, Organic
Pesticides · 3 items

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Acaricides

LogPlog Kow = 5.30
Color/FormColorless crystals
Solubility · 2 items

In isopropanol 10-20, dichloromethane 20-50, n-hexane 0.1-1, toluene 2-5 (all in g/l at 20 °C).

In water, 0.12 mg/l @ 20 °C.

Endocrine DisruptorsPotential endocrine disrupting compound
Decomposition · 2 items

Decomposition half-time (22 °C) 96 hr at pH 4; 81 hr at pH 7; 8 hr at pH 9.

When heated to decomposition it emits toxic fumes of NOx /nitrogen oxides/.

Melting Point210 °C (decomposes)
Vapor Pressure4.5X10-13 mm Hg at 25 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Regulation (EC) No 1107/2009 (amended)

2008/296

Azocyclotin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - 1H-1,2,4-Triazole, 1-(tricyclohexylstannyl)-: Human health tier I assessment
Hazards Summary · 1 item

A strong skin and eye irritant, based on animal studies; [HSDB] A skin and respiratory tract irritant; May cause severe damage to eyes; [eChemPortal: ESIS] Rapidly hydrolyzed to cyhexatin and 1,2,4-triazole in aqueous solution; In high-dose animal studies, causes spastic gait, diarrhea, and apathy; Corrosive to rabbit skin; At doses >2 mg/kg/day causes miscellaneous adverse effects in animals, including elevated liver enzymes; Unlikely to be genotoxic; [Reference #1] See Cyhexatin. See 1,2,4-Triazole.

Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of NOx /nitrogen oxides/.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Metabolized by hydrolysis, forming 1,2,4-triazole & tricyclohexyl tin hydroxide which is further oxidized to form dicyclohexyl tin oxide.

Though tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (L308)

Uses & manufacturing

Uses · 5 items

Used as a long lasting acaricide on fruit (including citrus), vines, hops, cotton, vegetables, and ornamentals; Not registered for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For Azocyclotin (USEPA/OPP Pesticide Code: 484600) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Long lasting acaricide with contact action used to control all motile stages of spider mites on fruit (including citrus), vines, hops, cotton, vegetables and ornamentals. /Former/

This is a man-made compound that is used as a pesticide.

Formulations/Preparations · 2 items

USEPA/OPP Pesticide Code 484600; Trade Names: Bay bue 1452, Peropal.

Wettable powder

Use ClassificationAcaricides
General Manufacturing InformationNot registered for use in U.S.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Nikkaji
J15.830E
Physical Description
Colorless solid; [HSDB]
Dissociation ConstantspKa=5.36

Physicochemical properties

Melting point
210 ℃ · 210℃
Boiling point
487.4 · 487.4±28.0 °C(Predicted)
vapor pressure
2 · 2×10-11 Pa (20 °C, est.)
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
5.36 · 5.36 (weak base)
Water Solubility
0.12 mg · 0.12 mg l-1 (20 °C)
BRN
621636 · 621636
Henry's Law Constant
4.6 · 4.6×106 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
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
InChIKey
ONHBDDJJTDTLIR-UHFFFAOYSA-N
SMILES
N1([Sn](C2CCCCC2)(C2CCCCC2)C2CCCCC2)C=NC=N1
CAS DataBase Reference
41083 · 41083-11-8(CAS DataBase Reference)
FDA UNII
4 YRQ367KE · V4YRQ367KE
NIST Chemistry Reference
1 H-1,2,4-triazole, · 1H-1,2,4-triazole, 1-(tricyclohexylstannyl)-(41083-11-8)
EPA Substance Registry System
Azocyclotin (41083-11-8)
Symbol(GHS)
5 · GHS05,GHS06,GHS09
Signal word
Danger
Hazard statements
301 · H301-H315-H318-H330-H335-H410
Precautionary statements
264 · P264-P270-P280-P260-P271-P284-P261-P273-P301+P310-P330-P302+P352-P332+P313-P362+P364-P305+P351+P338-P310-P304+P340-P312-P391-P405-P403+P233-P501
Hazard Codes
T+;N,N,T+
Risk Statements
25 · 25-26-37/38-41-50/53
Safety Statements
26 · 26-28-36/37/39-38-45-60-61
RIDADR
2786 · UN 2786
WGK Germany
3 · 3
RTECS
8637700 · WH8637700
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Hazardous Substances Data
41083 · 41083-11-8(Hazardous Substances Data)
Hazard Classes and Categories · 3 items

Acute Tox. 3 (100%)

Specific target organ toxicity (single exposure) - category 3

Acute Tox. 2 *

Shipping Name/ Number DOT/UN/NA/IMO · 3 items

UN 3146; Organotin cmpd, solid, not otherwise specified

UN 2788; Organotin cmpd, liquid, not otherwise specified

IMO 6.1; Organotin cmpd, liquid or solid, not otherwise specified

Skin, Eye, and Respiratory IrritationsStrong dermal irritant; strong & corrosive eye irritant (rabbits).

Safety & protection

Exposure Control and Personal Protection0.1 [mg/m3], inhalable fraction, as Sn[German Research Foundation (DFG)]
Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 1 item

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Threshold Limit Values (TLV) · 2 items

0.1 [mg/m3], as Sn

0.2 [mg/m3], as Sn

Permissible Exposure Limit (PEL)0.1 [mg/m3], as Sn
Immediately Dangerous to Life or Health (IDLH)25.0 [mg/m3], as Sn

Toxicology

Health EffectsBreathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (L307, L308)
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 18,000(SRC), determined from a log Kow of 5.3(2) and a regression-derived equation(3), indicates that azocyclotin is expected to be immobile in soil(SRC). Volatilization of azocyclotin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-12 atm-cu m/mole(SRC), derived from its vapor pressure, 4.5X10-13 mm Hg(2), and water solubility, 1.2X10-1 mg/l(2). Azocyclotin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 18,000(SRC), determined from a log Kow of 5.3(2) and a regression-derived equation(3), indicates that azocyclotin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4), derived from its vapor pressure, 4.5X10-13 mm Hg(2), and water solubility, 1.2X10-1 mg/l(2). The pKa of azocyclotin is 5.36(2), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). According to a classification scheme(6), an estimated BCF of 2,400(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low very high(SRC). Using a fresh water microcosm, azocyclotin was observed to be rapidly hydrolyzed to cyhexatin (tricyclohexyltinhydroxide) in a matter of days(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), azocyclotin, which has a vapor pressure of 4.5X10-13 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase azocyclotin may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral (L308) ; inhalation (L308) ; dermal (L308)
Toxicity Summary · 1 item

Organotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (L308, A182, A184)

Signs and SymptomsInorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)
Soil Adsorption/Mobility · 1 item

The Koc of azocyclotin is estimated as 18,000(SRC), using a log Kow of 5.3(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that azocyclotin is expected to be immobile in soil. The pKa of azocyclotin is 5.36(1), indicating that this compound will partially exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4).

Artificial Pollution SourcesAzocyclotin's former(2) production and use as an acaricide(1) may result in its direct release to the environment(SRC).
Environmental BiodegradationIn a fresh water microcosm study, 14C-azocyclotin was observed to be rapidly hydrolyzed to cyhexatin, which in turn was mineralized to 14CO2(1).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1 item

An estimated BCF of 2,400 was calculated for azocyclotin(SRC), using a log Kow of 5.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for azocyclotin is estimated as 2.15X10-12 atm-cu m/mole(SRC) derived from its vapor pressure, 4.5X10-13 mm Hg(1), and water solubility, 1.2X10-1 mg/l(1). This Henry's Law constant indicates that azocyclotin is expected to be essentially nonvolatile from water surfaces(2). Azocyclotin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Safety data

wgk
3
rtecs
WH8637700
ridadr
UN 2786
risk_code
25-26-37/38-41-50/53
Signal word
Danger
Symbol(GHS)
GHS05,GHS06,GHS09
hazard_code
T+;N,N,T+
safety_code
26-28-36/37/39-38-45-60-61
hazard_class
6.1(a)
packing_group
I
Hazard statements
H301-H315-H318-H330-H335-H410
Precautionary statements
P264-P270-P280-P260-P271-P284-P261-P273-P301+P310-P330-P302+P352-P332+P313-P362+P364-P305+P351+P338-P310-P304+P340-P312-P391-P405-P403+P233-P501
Hazardous Substances Data
41083-11-8(Hazardous Substances Data)
Applications · 3 items

DescriptionAzocyclotin 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.

UsesAzocyclotin is an organotin aracacide used in the control of mites. Azocyclotin showed weak antifeedant activity against other insects such as Spodoptera littoralis.

UsesAzocyclotin is used to control all motile stages of spider mites on fruit, vines, hops, cotton, vegetables and ornamentals.

Upstream & downstream products

Upstream raw materials

Tricyclohexyltin chlorideTinChlorocyclohexaneMagnesiumCyhexatin

Downstream products

Azocyclotin suspensoidAzocyclotin W.P.

Additional notes

DefinitionChEBI: A member of the class of triazoles that is 1,2,4-triazole substituted at position 1 by a tricyclohexylstannyl group.