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Fenbutatin oxide

Fenbutatin oxide structure

Fenbutatin oxide 

structure
  • CAS No:

    13356-08-6

  • Formula:

    C60H78OSn2

  • Chemical Name:

    Fenbutatin oxide

  • Synonyms:

    Distannoxane,1,1,1,3,3,3-hexakis(2-methyl-2-phenylpropyl)-;Distannoxane,hexakis(β,β-dimethylphenethyl)-;Distannoxane,hexakis(2-methyl-2-phenylpropyl)-;1,1,1,3,3,3-Hexakis(2-methyl-2-phenylpropyl)distannoxane;Trineophyltin oxide;SD 14114;Vendex;Hexakis(2-methyl-2-phenylpropyl)distannoxane;Hexakis(β,β-dimethylphenethyl)distannoxane;Torque (pesticide);Fenbutatin oxide;Neostanox;Torque;Vendex 4L;Hexakis;Osadan;Vendex 4 Liquid;Bis[tris(2-methyl-2-phenylpropyl)tin] oxide;Partner;Bis[tri(2-phenyl-2-methylpropyl)tin] oxide;Bis[tris(2-phenyl-2-methylpropyl)tin] oxide;Bis[tri(2-methyl-2-phenylpropyl)tin] oxide;1,1,1,3,3,3-Hexakis(2,2-dimethyl-2-phenylethyl)distannoxane;12684-28-5;57547-75-8

  • Categories:

    Agrochemicals  >  Insecticides

Description

White crystalline solid or powder. Mild odorWhite crystalline solid with a mild odor.


Fenbutatin oxide is a white crystalline solid with a mild odor.|Solid


Fenbutatin oxide is a white crystalline solid with a mild odor.|Fenbutatin oxide is an organotin acaricide.

Fenbutatin oxide Basic Attributes

1052.68

1052.68

236-407-7

ZSV4C2L4E7

2811

DTXSID7032391

White crytalline powder

2902909090

Characteristics

9.2

5.2

Fenbutatin oxide is a white crystalline solid with a mild odor.

0.42 g/cm3

138-139 °C

235-240 °C @ Press: 0.05 Torr

100 °C

1.27e-05 mg/mL at 20 °C

APPROX 4°C

8.5×10 -8 Pa (20 °C)

Oral-rat LD50: 2630 mg/kg; Oral-Mouse LD50: 1450 mg/kg

Thermal decomposition of toxic tin-containing gas

Not autoflammable but tech. will explode in a dust cloud if ignited.

Mild odor

Water causes conversion of fenbutatin oxide to tris(2-methyl-2-phenylpropyl)tin hydroxide which is reconverted to parent compound slowly at room temperature and rapidly at 98 °C.|Triorganotin oxides and hydroxides are moderately strong bases and react readily with a wide variety of acidic compounds. /Triorganotin oxides/

Insoluble in water.

Hydrocarbons, Aromatic

FENBUTATIN OXIDE is in the family of tin compounds widely used as stabilizers for plastics, additives to paint(as antifouling agents). Some have catalytic properties. Examples include butyl tin, dibutyl tin oxide. Their main hazard is associated with their high toxicity, in skin adsorption or inhalation.

Safety Information

III

9

UN 2811

3

21-36/38-50/53-26

28-36/37-45-60-61

JN8770000

Xn;N,N,Xn,T+

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

Compatible with many other pesticides.

P260-P304 + P340 + P310-P305 + P351 + P338-P403 + P233

H315-H319-H330-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.

Water causes conversion of fenbutatin oxide to tris(2-methyl-2-phenylpropyl)tin hydroxide which is reconverted to the parent compound slowly at room temperature and rapidly at 98 °C.

NIOSH; Criteria Document: Organotin Compounds (1976) DHEW Pub. NIOSH 77-115|USEPA; Health Effects Assessment for Tin and Compounds p.4 (1987) EPA/600/8-88/055|WHO; Environ Health Criteria: Tin and Organotin Cmpd p.1-109 (1980)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)

|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P260, P264, P271, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P310, P320, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 156 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P271, P273, P280, P281, P284, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P320, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|P260, P264, P270, P280, P302+P352, P305+P351+P338, P307+P311, P309+P311, P321, P332+P313, P337+P313, P362, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)

Not autoflammable but tech. will explode in a dust cloud if ignited.

Not autoflammable but tech. will explode in a dust cloud if ignited.

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.

Skin and eye irritant.

Toxicity

moderately toxic

LD50 Rat acute oral 2631 mg/kg|LD50 Mouse acute oral 1450 mg/kg|LD50 Dog acute oral >1500 mg/kg|LD50 Rabbit acute percutaneous >2000 mg/kg|LD50 Rat acute percutaneous >1000 mg/kg

Fenbutatin oxide's production and use as an acaracide(1) and miticide(2) results in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on mobility studies in soil columns(1), fenbutatin oxide is expected to be immobile in soil(SRC). Volatilization from moist soil surfaces is not expected(2) based upon an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.8X10-11 mm Hg(1), and water solubility, 0.0127 mg/l(1). Fenbutatin oxide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). Fenbutatin oxide was relative stable in three soils under both aerobic (80% remained after 12 months) and anaerobic (80% remained after 60 days) conditions(1).|TERRESTRIAL FATE: Fenbutatin oxide was persistent under field conditions(1). It dissipated with half-lives between 271 and 1,367 days from the upper 30 cm of bareground plots of silt loam soil located in Delaware, loam soil located in Washington, and loam/sandy loam soil located in California(1). These plots had been treated at 8 lb a.i./A/year for 3 years with fenbutatin oxide(1). Fenbutatin oxide and its metabolites demonstrated low mobility at all of the test sites throughout the course of the study(1). After the third application, approximately 90% of the residues remained in the top 10 cm of soil at each of the sites(1). Of the three sites, only California (2% of total residues) showed residues in soil at the 60-90 cm level(1). The degradates identified in the treated soil were 1,3-dihydroxy-1,1,3,3-tetrakis(2-methyl-2-phenylpropyl) distannoxane and 2-methyl-2-phenylpropyl stannonic acid(1). These long half-lives caused residue levels to increase with successive applications(1).|AQUATIC FATE: Based on mobility studies in soil columns(1), fenbutatin oxide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.8X10-11 mm Hg(1), and water solubility, 0.0127 mg/l(1). Fenbutatin oxide photodegraded in sterile water at pH 7 with a half-life of 55 days under continuous irradiation(1). This half-life would translate to a half-life of over 100 days if fenbutatin oxide were exposed to 12 hours of irradiation alternated with 12 hours of darkness(1). According to a classification scheme(3), BCF values ranging from 340 to 500(1), suggest the potential for bioconcentration in aquatic organisms is high(SRC). Fenbutatin oxide was relative stable in three soils under both aerobic and anaerobic conditions and is expect to be stable to degradation water(1). Fenbutatin oxide is stable to hydrolysis at pH's 5, 7, and 9 in sterile aqueous solutions(1).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fenbutatin oxide, which has a vapor pressure of 1.8X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere(SRC). Particulate-phase fenbutatin oxide may be removed from the air by wet and dry deposition(SRC).

Fenbutatin oxide was stable to hydrolysis at pH's 5, 7, and 9 in sterilized buffered aqueous solutions kept in darkness at approximately 25 °C(1). After 30 days of incubation in each test solution, fenbutatin oxide comprised more than 90% of the originally applied radioactivity(1). Fenbutatin oxide photodegraded in sterile water at pH 7 with a half-life of 55 days under continuous irradiation(1). This half-life would translate to a half-life of over 100 days if fenbutatin oxide were exposed to 12 hours of irradiation alternated with 12 hours of darkness(1). The only major photolytic degradation product was 1,3-dihydroxy-1,1,3,3-tetrakis(2-methyl-2-pheylpropyl) distannoxane(1). The degradation product comprised 22.8% of total radioactivity by day 15 of continuous exposure to radiation >290nm. Fenbutatin oxide is realtively stable towards potodegradation on soil(1). The half-life of fenbutatin oxide was 128 days on sandy loam soil irradiated on a 12-hour photoperiod with a xenon arc lamp for 31 days(1). The major degradate was 1,3-dihydroxy-1,1,3,3-tetrakis(2-methyl-2-phenylpropyl)distannoxane, comprising a maximum of 3.4% of the applied radioactivity at 31 days posttreatment. Fenbutatin oxide did not degrade in dark controls(1).

Fenbutatin oxide does accumulate in fish tissues, as expected from its Kow (ie, 1.4X10+5)(1). Bioconcentration factors of 340 to 500 for muscle tissue, 1,110 to 1,600 for visceral tissue, 450 to 640 for the remaining carcass and 490 to 730 for whole fish were determined for bluegill sunfish exposed to fenbutatin oxide at 0.00013 mg/l or 0.00068 mg/l(1). However, the lack of a plateau in the concn of fenbutatin oxide in the various tissues could indicate that the actual BCF's are higher(1). Depuration of the accumulated residues was somewhat limited, with only 51-75% of the accumulated residues being eliminated by day 14 of the depuration period(1). According to a classification scheme(2), BCF values of 490 to 730(1) suggest bioconcentration in aquatic organisms is high(SRC).

Unaged fenbutatin oxide was immobile in columns of two loamy sand soils, a silty clay soil, and a sandy clay soil(1). More than 90% of the Sn-119 residues did not move out of the treated layer(1). Fenbutatin oxide residues aged for 30 days were slightly mobile in a column of loamy sand soil. SN-119 residues were distributed throughout the column (92% in the upper 6 cm) and 1% were recovered in the leachate(1). Sn-119 in fenbutatin oxide comprised 98% of the recovered extractable radioactivity in the soil(1). Fenbutatin oxide with a 0.2% surfactant at 0.1, 1.0, and 10 ug/ml, was slightly mobile to immobile (Kads: 6.9 to 3,587) in two loamy sand soils, a silty clay soil and a sandy clay loam soil(1). Less than 5% of the adsorbed pesticide desorbed from the soil(1). Fenbutatin oxide with a 1% acetone co-solvent at 5, 1 ,0.2 and 0.04 mg/ml was immobile (Kd: 1,282 to 2,333) in a loamy sand, sandy loam, and silty loam soil(1). Less than 0.5% of the adsorbed pesticide desorbed from the soil(1).

The Henry's Law constant for fenbutatin oxide is estimated as 2.0X10-9 atm-cu m/mole(SRC) based upon its vapor pressure, 1.8X10-11 mm Hg(1), and water solubility, 0.0127 mg/l(1). This Henry's Law constant indicates that fenbutatin oxide is expected to be essentially nonvolatile from water surfaces(2). Fenbutatin oxide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Fenbutatin oxide was detected as a residue in regulatory monitoring of foods by the Food and Drug Administration during the period 1983-1986, but the levels in specific foods were not reported(1). In a 1989 pesticide in food monitoring program by the California Department of Food, fenbutatin oxide was detected in 100% of oranges, 100% of pears and 23% of strawberries(2).

Occupational exposure to fenbutatin oxide may occur through inhalation and dermal contact with this compound at workplaces where fenbutatin oxide is produced or used. Monitoring data indicate that the general population may be exposed to fenbutatin oxide via ingestion of food. (SRC)

Drug Information

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)

fenbutatin oxide

Fenbutatin oxide Use and Manufacturing

Methods of Manufacturing

First, Grignard reagent is prepared by reacting 1-chloro-2-methyl-2-phenylpropane with magnesium, and then reacting with tin tetraoxide to produce tri(2-methyl-2-phenylpropyl) tin chloride, Furthermore, tincide is produced under the action of sodium hydroxide. Raw material consumption quota: methallyl chloride 1700kg/t, benzene 1800kg/t, metal magnesium 300kg/t, metal tin 300kg/t, tetrahydrofuran 400kg/t, xylene 300kg/t.

Uses

Acaricide.

361,000 to 522,000 lbs annually from 1989-1991.

USEPA/OPP Pesticide Code 104601; Trade Names: Neostanox, Vendex, Torque, SD 14114.|Wettable powder (500 g active ingredient/kg); suspension concentrate (500 g/l)|Liquid concentrate, suspension concentrate, wettable powder.

Distannoxane, 1,1,1,3,3,3-hexakis(2-methyl-2-phenylpropyl)-: ACTIVE

Agrochemicals -> Acaricides|Acaricides, Insecticides|ACARICIDES

Computed Properties

Molecular Weight:1052.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:20
Exact Mass:1052.40908
Monoisotopic Mass:1054.40967
Topological Polar Surface Area:9.2
Heavy Atom Count:63
Complexity:1070
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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