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Azocyclotin

Azocyclotin structure

Azocyclotin 

structure
  • CAS No:

    41083-11-8

  • Formula:

    C20H35N3Sn

  • Chemical Name:

    Azocyclotin

  • Synonyms:

    1H-1,2,4-Triazole,1-(tricyclohexylstannyl)-;1-(Tricyclohexylstannyl)-1H-1,2,4-triazole;Tricyclotin;Azocyclotin;Peropal;BAY-BUE 1452;Caligur 500SC

  • Categories:

    Agrochemicals  >  Insecticides

Description

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


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 an organotin acaricide and a member of triazoles.

Azocyclotin Basic Attributes

436.22

436.22

255-209-1

V4YRQ367KE

DTXSID2058091

Colorless crystals

2931900046

Characteristics

30.7

5.30

white, light,yellow crystal powder

210 °C (decomp)

487.4±28.0 °C at 760 mmHg

248.6±24.0 °C

In water, 0.12 mg/l @ 20 deg C.

0-6°C

2×10 -11 Pa (20 °C, est.)

Oral-rat LD50: 100 mg/kg; Oral-Mouse LD50: 700 mg/kg

Thermal decomposition of toxic nitrogen oxides and tin-containing gases

pKa=5.36

Safety Information

I

6.1(a)

UN 2786

3

25-26-37/38-41-50/53

26-28-36/37/39-38-45-60-61

WH8637700

T+;N,N,T+

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

P260-P273-P280-P284-P301 + P310-P305 + P351 + P338

H301-H315-H318-H330-H335-H410

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.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P330, P332+P313, P362, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

Strong dermal irritant; strong & corrosive eye irritant (rabbits).

Toxicity

highly toxic

LD50 Rat male oral 209 mg/kg|LD50 Rat female oral 363 mg/kg|LD50 Guinea pig oral 261 mg/kg|LD50 Mouse oral 870-980 mg/kg|For more Non-Human Toxicity Values (Complete) data for AZOCYCLOTIN (8 total), please visit the HSDB record page.

Azocyclotin's former(2) production and use as an acaricide(1) may result in its direct release to the environment(SRC).

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).

Azocyclotin, which has a vapor pressure of 4.5X10-13 mm Hg at 25 °C(1), 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). Using a fresh water microcosm, 14C-azocyclotin was observed to be rapidly hydrolyzed to cyhexatin (tricyclohexyltinhydroxide) in a matter of days, which is then mineralized to 14CO2 and polar metabolites(2).

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).

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).

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).

Occupational exposure to azocyclotin may have occurred through inhalation of dust and dermal contact with this compound at workplaces where azocyclotin was produced or used. The general population may have been exposed through inhalation and dermal contact during its former use as an acaricide. (SRC)

Drug Information

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

azocyclotin

Azocyclotin Use and Manufacturing

Methods of Manufacturing

In the preparation reactor of tricyclohexyl tin hydroxide, magnesium flakes are added in advance, and a certain amount of a mixed solution of chlorocyclohexane and THF is added to the temperature under the protection of nitrogen. After the reaction starts, continue to add the remaining mixture. After the reaction is completed, it reacts with the tin tetrachloride xylene solution to form tricyclohexyl tin chloride. Dissolve the magnesium chloride with dilute hydrochloric acid, separate the layers, remove the xylene, and then NaOH reacts to form tricyclohexyl tin hydroxide, which is separated and dried to obtain the product. Synthesis of triazole tin Add tricyclohexyl tin hydroxide and acetone to the reactor, heat to reflux, and add triazole acetone solution dropwise. After the dropping, keep the temperature under reflux, lower the temperature to 0℃, filter, and dry to obtain triazole tin. The filtrate recovers the solvent. The synthesis of triazole tin can also use the following methods.

Uses

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

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

Not registered for use in U.S.

Agrochemicals -> Acaricides|Acaricides

Computed Properties

Molecular Weight:436.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:437.185301
Monoisotopic Mass:437.185301
Topological Polar Surface Area:30.7
Heavy Atom Count:24
Complexity:339
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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