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.
Colorless crystals. Insoluble in water, soluble in dichloromethane and isopropanol.
Azocyclotin is used to control all motile stages of spider mites on
fruit, vines, hops, cotton, vegetables and ornamentals.
Azocyclotin is an organotin aracacide used in the control of mites. Azocyclotin showed weak antifeedant activity against other insects such as Spodoptera littoralis.
ChEBI: A member of the class of triazoles that is 1,2,4-triazole substituted at position 1 by a tricyclohexylstannyl group.
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.
Contact action. Inhibits oxidative phosphorylation. Inhibitor of mitochondrial ATP synthase.
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.
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).
