| Identification | More | [Name]
Azocyclotin | [CAS]
41083-11-8 | [Synonyms]
1-(TRICYCLOHEXYL-STANNYL)-1H-1,2,4-TRIAZOLE
AZOCYCLOTIN
CLAIRMAIT(R)
CLERMAIT(R)
PEROPAL
PEROPAL(R)
(1h-1,2,4-triazol-1-yl)tricyclohexyl-stannan
(1h-1,2,4-triazolyl)tricyclohexylstannane
2,4-Triazole,1-(tricyclohexylstannyl)-1H-1
baybue1452
tri(cyklohexyl)-1h-1,2,4-triazol-1-ylstannium
Triclotin
AZOCYCLOTIN PESTANAL (1-(TRICYCLO-HEXYL
AZOCYCLOTIN, 250MG, NEAT
Tricyclotin
1H-1,2,4-Triazole, 1-(tricyclohexylstannyl)-
azocyclotin (bsi,iso,esa)
AZOCYCLOTIN STANDARD
1-(tricyclohexylstannyl)-1H-1,2,4-triazole azocyclotin
Clermait | [EINECS(EC#)]
255-209-1 | [Molecular Formula]
C20H35N3Sn | [MDL Number]
MFCD00055290 | [Molecular Weight]
436.22 | [MOL File]
41083-11-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
210℃ | [Boiling point ]
487.4±28.0 °C(Predicted) | [vapor pressure ]
2×10-11 Pa (20 °C, est.) | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
5.36 (weak base) | [Water Solubility ]
0.12 mg l-1 (20 °C) | [BRN ]
621636 | [Henry's Law Constant]
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]
41083-11-8(CAS DataBase Reference) | [NIST Chemistry Reference]
1H-1,2,4-triazole, 1-(tricyclohexylstannyl)-(41083-11-8) | [EPA Substance Registry System]
41083-11-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+;N,N,T+ | [Risk Statements ]
R25:Toxic if swallowed.
R26:Very Toxic by inhalation.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S38:In case of insufficient ventilation, wear suitable respiratory equipment .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2786 | [WGK Germany ]
3 | [RTECS ]
WH8637700 | [HazardClass ]
6.1(a) | [PackingGroup ]
I | [Hazardous Substances Data]
41083-11-8(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Description]
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. | [Chemical Properties]
Colorless crystals. Insoluble in water, soluble in dichloromethane and isopropanol. | [Uses]
Azocyclotin is an organotin aracacide used in the control of mites. Azocyclotin showed weak antifeedant activity against other insects such as Spodoptera littoralis. | [Uses]
Azocyclotin is used to control all motile stages of spider mites on
fruit, vines, hops, cotton, vegetables and ornamentals. | [Definition]
ChEBI: A member of the class of triazoles that is 1,2,4-triazole substituted at position 1 by a tricyclohexylstannyl group. | [Production Methods]
Azocyclotin is synthesised through a multi-step process involving organotin and triazole chemistry. The production begins with the reaction of tin tetrachloride and chlorocyclohexane to form a cyclohexylated tin intermediate. This intermediate is then reacted with 1,2,4-triazole, followed by chlorination and alkalization steps to yield azocyclotin. | [Mechanism of action]
Contact action. Inhibits oxidative phosphorylation. Inhibitor of mitochondrial ATP synthase. | [Metabolic pathway]
The sedimentation of particles coated with the
pesticide is relatively fast. Shortly after application of
14C-azocyclotin, distribution, solubilizing, and
metabolism in fresh water microcosms begin, and
azocyclotin is quickly hydrolyzed to cyhexatin
(tricyclohexyltin hydroxide) by splitting of the triazole
residue, and, according to the solubility of cyhexatin,
cyhexatin is mainly absorbed to sediment and the
layer of biota in direct contact with the sediment and
further undergoes successive metabolism to result in
dicyclohexyltin oxide and cyclohexyltin acid. | [Degradation]
Azocyclotin undergoes hydrolysis with DT50 values (22 °C) of 96 hours at
pH 4,81 hours at pH 7 and 8 hours at pH 9 (I'M). | [Pesticide Type]
Acaricide |
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