Cyhexatin

Metals -> Tin Compounds, Organic

Teratogens

Acaricides

Active substance -> EU Pesticides database: Not approved

Transformation products, Acaricides, Insecticides

Insoluble (NIOSH, 2024)

In water <1 mg/l (25 °C)

In acetone 1.3 g/kg at 25 °C; in chloroform 216 g/kg at 25 °C; in methanol 37 g/kg at 25 °C; in toluene 10 g/kg at 25 °C; in dichloromethane 34 g/kg at 25 °C; in carbon tetrachloride 28 g/kg at 25 °C; in benzene 16 g/kg at 25 °C; in xylene 3.6 g/kg at 25 °C

Insoluble

442 °F at 760 mmHg (Decomposes) (NIOSH, 2024)

442 °F (decomposes)

442 °F (Decomposes)

When heated to decomp ... emits acrid smoke and irritating fumes.

Degraded by u.v. light.

383 °F (NIOSH, 2024)

196 °C

383 °F

383 °F

0 mmHg (approx) (NIOSH, 2024)

Negligible (25 °C)

0 mmHg (approx)

0 mmHg (approx)

Technical cyhexatin is a nearly odorless white crystalline powder that has no true melting point but degrades to bis(tricyclohexyl)tin oxide at 121 to 131 °C which decomposes at 228 °C; a melting point of 195-198 °C is also reported. Very insoluble in water (less than 1 mg/L at 25 °C), but wettable by water. Soluble in some organic solvents (acetone 1.3 g/L; xylenes 3.6 g/L; carbon tetrachloride 28 g/L; dichloromethane 34 g/L). Used as an acaricide (an agent to kill plant-feeding mites) in almonds, walnuts, hops and some fruits.

Colorless to white, nearly odorless, crystalline powder; (insecticide); [NIOSH]

Colorless to white, nearly odorless, crystalline powder.

Colorless to white, nearly odorless, crystalline powder. [insecticide]

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Danger

H301 (24.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Developmental Toxicity

Regulation (EC) No 1107/2009 (amended)

Cyhexatin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2008/296

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

May cause skin burns; May cause liver and kidney damage in animals; [NIOSH] In 2 year feeding studies of dogs, the no-effect-level was 0.75 mg/kg daily; Dogs showed dose-dependent focal bile duct hyperplasia; In sheep, an injection of 50 mg/kg caused anorexia, CNS depression, and diarrhea; [HSDB] For purposes of the TLV, Cyhexatin is considered separately and not with Tin, organic compounds. Oral LD50 (rat) = 540 mg/kg; Intraperitoneal LD50 (rat) = 13 mg/kg; Rats fed 12 mg/kg/day were smaller than controls; Rats fed 25mg/kg/day (gavage) for 2 weeks had changes in their liver, kidneys, and adrenal glands; See Tin, organic compounds.

Tolerances are established for combined residues of the pesticide cyhexatin (tricyclohexylhydroxystannane; CAS Reg No 13121-70-5) and its organotin metabolites (calculated as cyhexatin) in or on the following food commodities: almonds; almond, hulls; apples; cattle, fat; cattle, kidney; cattle, liver; cattle, mbyp (excluding kidney, liver); cattle, meat; citrus fruits; citrus pulp, dried; goats, fat; goats, kidney; goats, liver; goats, mbyp (excluding kidney, liver); goats, meat; hogs, fat; hogs, kidney; hogs, liver; hogs, mbyp (excluding kidney, liver); hogs, meat; hops; hops, dried; horses, fat; horses, kidney; horses, liver; horses, mbyp (excluding kidney, liver); horses, meat; macadamia nuts; milk, fat (=N in whole milk); nectarines; peaches; pears; plums (fresh prunes); prunes, dried; sheep, fat; sheep, kidney; sheep, liver; sheep, mbyp (excluding kidney, liver); sheep, meat; strawberries; and walnuts.

CYHEXATIN is incompatible with strong oxidizing agents. Soluble in some organic solvents (acetone 1.3 g/L; xylenes 3.6 g/L; carbon tetrachloride 28 g/L; dichloromethane 34 g/L). Stable in aqueous suspensions in neutral and alkaline pH (above pH 6), but reacts exothermically as a base in the presence of strong acids to form salts. Converts to dicyclohexyltin oxide and further to cyclohexylstannoic acid upon exposure to ultraviolet radiation.

Cyhexatin

Severe marine pollutant

Excerpt from NIOSH Pocket Guide for Cyhexatin:

(General first aid procedures)

Keep in cool place. Keep contents under ... (appropriate liquid to be specified by the manufacturer). Keep under ... (inert gas to be specified by the manufacturer). Keep container tightly closed. Keep container dry. Keep container in well-ventilated place. Do not keep the container sealed.

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.

Keep out of reach of children. Keep away from living quarters. Keep away from food, drink & animal feeding stuffs.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed or replaced.

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.

Tolerances are established for combined residues of the pesticide cyhexatin (tricyclohexylhydroxystannane; CAS Reg No 13121-70-5) and its organotin metabolites (calculated as cyhexatin) in or on the following food commodities: almonds, 0.5 ppm; almond, hulls, 60 ppm; apples, 2 ppm; cattle, fat, 0.2 ppm; cattle, kidney, 0.5 ppm; cattle, liver, 0.5 ppm; cattle, mbyp (excluding kidney, liver), 0.2 ppm; cattle, meat, 0.2 ppm; citrus fruits, 2 ppm; citrus pulp, dried, 8 ppm; goats, fat, 0.2 ppm; goats, kidney, 0.5 ppm; goats, liver, 0.5 ppm; goats, mbyp (excluding kidney, liver), 0.2 ppm; goats, meat, 0.2 ppm; hogs, fat, 0.2 ppm; hogs, kidney, 0.5 ppm; hogs, liver, 0.5 ppm; hogs, mbyp (excluding kidney, liver), 0.2 ppm; hogs, meat, 0.2 ppm; hops, 30 ppm; hops, dried, 90 ppm; horses, fat, 0.2 ppm; horses, kidney, 0.5 ppm; horses, liver, 0.5 ppm; horses, mbyp (excluding kidney, liver), 0.2 ppm; horses, meat, 0.2 ppm; macadamia nuts, 0.5 ppm; milk, fat (=N in whole milk), 0.05 ppm; nectarines, 4 ppm; peaches, 4 ppm; pears, 2 ppm; plums (fresh prunes), 1 ppm; prunes, dried, 4 ppm; sheep, fat, 0.2 ppm; sheep, kidney, 0.5 ppm; sheep, liver, 0.5 ppm; sheep, mbyp (excluding kidney, liver), 0.2 ppm; sheep, meat, 0.2 ppm; strawberries, 3 ppm; and walnuts, 0.5 ppm.

5.0 [mg/m3]

8 hr Time Weighted Avg (TWA): 5 mg/cu m.

Excursion Limit Recommendation: Excursions in worker exposure levels may exceed three times the TLV-TWA for no more than a total of 30 min during a work day and under no circumstances should they exceed five times the TLV-TWA, provided that the TLV-TWA is not exceeded.

A4; Not classifiable as a human carcinogen.

5 mg/m³ [1990]

0.1 [mg/m3], as Sn

0.1 mg/m³ (Tin, organic compounds)

TWA 0.32 mg/m3 [0.1 mg/m3 (as Sn)] See Appendix G

5 mg/m³

TWA 5 mg/m3

LC50 MICROPTERUS SALMOIDES (LARGEMOUTH BASS) 2.1 UG/L/96 HR AT 18 °C (95% CONFIDENCE LIMIT 1.9-2.3 UG/L), WT 0.8 G /STATIC BIOASSAY, TECHNICAL MATERIAL 95% IN HARD WATER/

LC50 GAMMARUS FASCIATUS (SCUD) 5 UG/L/96 HR AT 15 °C; MATURE, /STATIC BIOASSAY, TECHNICAL MATERIAL, 95%/

LC50 LEPOMIS MACROCHERIS (BLUEGILL) 6.7 UG/L/96 HR AT 18 °C (95% CONFIDENCE LIMIT 5.8-7.7 UG/L), WT 1.1 G, /STATIC BIOASSAY, TECHNICAL MATERIAL, 95%/

LD50 Bobwhite quail oral 520 mg/kg in 8 day diet

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of >4365(2), indicates that tricyclohexyltin hydroxide is expected to have slight mobility in soil(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process since tricyclohexyltin hydroxide will dissociate in water to the tricyclohexyltin cation and ions will not volatilize(SRC). Tricyclohexyltin hydroxide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2X10-9 mm Hg(SRC), determined from a fragment constant method(3). The field half-life for tricyclohexyltin hydroxide is reported to be 50 days(2). Biodegradation in soil is not expected to be an important environmental fate process as evidenced by the lack of dicyclohexyl and monocyclohexyl degradation products in soils under aerobic or anaerobic conditions(4).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of >4365(2), indicates that tricyclohexyltin hydroxide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water is not expected to be an important fate process since tricyclohexyltin hydroxide will dissociate in water to the tricyclohexyltin cation and ions will not volatilize(SRC). According to a classification scheme(3), a BCF range of 5-112(4,5), suggests the potential for bioconcentration in aquatic organisms is low-to-moderate(SRC). Biodegradation in water is not expected to be an important environmental fate process as evidenced by the lack of dicyclohexyl and monocyclohexyl degradation products in soils under aerobic or anaerobic conditions(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tricyclohexyltin hydroxide, which has an estimated vapor pressure of 2X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere(3). Particulate-phase tricyclohexyltin hydroxide may be removed from the air by wet and dry deposition(SRC). Tricyclohexyltin hydroxide may undergo direct photolysis. 65% and 96% photodegradation was observed after 8-10 and 30 hours of irradiation, respectively(4). The observed products of photodegradation included inorganic tin compounds, dicyclohexyltin oxide, cyclohexylstannoic acid, and unchanged tricyclohexyltin hydroxide(4).

After the multiple application of tricyclohexyltin hydroxide to apples and pears, the mean fruit concn of tin was 0.3 mg/kg, and a maximum below 2.0 mg/kg. The miticide decomposed with a half-time of 3 weeks, and most could be removed by washing and peeling.

Tricyclohexyltin hydroxide was detected in 142 of 19,851 samples of various foods and animal feeds analyzed from Oct 1981 to Sept 1986; the numbers of samples found at various concn ranges were as follows: 11 samples at >0.05 to 0.10 ppm; 49 samples at >0.10 to 0.50 ppm; 27 samples at >0.50 to 1.0 ppm; 26 samples at >2.0 ppm(1).

The concn of tricyclohexyltin hydroxide in produce like tomatoes, cucumbers and bell peppers grown in green houses were unlikely to exceed 0.5 mg/kg(1). Tricyclohexyltin hydroxide residues were found in raw agricultural commodities by the US FDA during regulator monitoring in 1978-1982(2) and 1983-1986(3). During each of these periods about 49,000 samples were analyzed. Similarly tricyclohexltin hydroxide residues were found in food samples collected and analyzed by 10 state food laboratories in 1988 and 1989 (27,000 samples)(4). The number of samples containing residues and the concn found in these studies were not reported.

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral (L308) ; inhalation (L308) ; dermal (L308)

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)

Apples and pears sprayed four times with tricyclohexyltin hydroxide had maximum organotin residues of 2 mg/kg of whole fruit on the day of final application; the concn was reduced to about half in 3-5 wks as a result of photodegradation(1). The residue consisted mostly of tricyclohexyltin hydroxide with very little degradation product; total tin concns were below 0.2 mg/kg.

irritation eyes, skin, respiratory system; headache, dizziness; sore throat, cough; abdominal pain, vomiting; skin burns, pruritus; In Animals: liver, kidney damage

Inorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (L308)

The Koc for tricyclohexyltin hydroxide is >4365(1). According to a classification scheme(2), this Koc value suggests that tricyclohexyltin hydroxide is expected to be immobile in soil. Tricyclohexyltin hydroxide appears to be strongly bound to soil based on a field experiment in which 90% of the cyclohexyltin compounds found in the soil of an orchard sprayed with a tricyclohexyltin hydroxide formulation was present in the uppermost 1 cm layer of the soil(3).

Tolerances are established for combined residues of the pesticide cyhexatin (tricyclohexylhydroxystannane; CAS Reg No 13121-70-5) and its organotin metabolites (calculated as cyhexatin) in or on the following food commodities: almonds; almond, hulls; apples; cattle, fat; cattle, kidney; cattle, liver; cattle, mbyp (excluding kidney, liver); cattle, meat; citrus fruits; citrus pulp, dried; goats, fat; goats, kidney; goats, liver; goats, mbyp (excluding kidney, liver); goats, meat; hogs, fat; hogs, kidney; hogs, liver; hogs, mbyp (excluding kidney, liver); hogs, meat; hops; hops, dried; horses, fat; horses, kidney; horses, liver; horses, mbyp (excluding kidney, liver); horses, meat; macadamia nuts; milk, fat (=N in whole milk); nectarines; peaches; pears; plums (fresh prunes); prunes, dried; sheep, fat; sheep, kidney; sheep, liver; sheep, mbyp (excluding kidney, liver); sheep, meat; strawberries; and walnuts.

ANALYSIS FOR METABOLITES IN TISSUE /RATS/ THAT HAD BEEN ON DIETARY LEVEL OF 3 MG/KG /TRICYCLOHEXYLTIN HYDROXIDE/ FOR 90 DAYS SHOWED 45% OF THE TOTAL TIN TO BE IN FORM OF THE ORIGINAL CMPD IN THE LIVER WITH ONLY SLIGHTLY GREATER AMT FOUND AS METABOLIZED PRODUCTS, DICYCLOHEXYL TIN OXIDE AND INORGANIC TIN.

PLICTRAN YIELDS PRODUCTS WITH THE ANTICIPATED CHROMATOGRAPHIC PROPERTIES FOR 2-, 3-, & 4-HYDROXYCYCLOHEXYLDICYCLOHEXYLTIN DERIVATIVES. THE 2-HYDROXY METABOLITE IS READILY DEGRADED TO CYCLOHEXANE & DICYCLOHEXYLTIN COMPOUNDS.

When (114)tin-tricyclohexyltin hydroxide was given as single oral doses to rats, dogs, cattle & sheep, the label was excreted almost entirely in feces. Only traces of residues occurred in tissues. Evidence indicated that such metabolism as did occur converted this compound by sequential removal of cyclohexyl groups to dicyclohexyltin oxide, cyclohexylstannoic acid, & to inorganic tin.

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)

IN METABOLIC STUDY IN RATS GIVEN 25 MG/KG (119)TIN LABELED TRICYCLOHEXYLHYDROXYTIN ORALLY, ALMOST ALL RADIOACTIVITY WAS RECOVERED IN THE URINE & FECES DURING A 9 DAY PERIOD WITH ABOUT 80% IN THE FIRST 4 DAYS, THE FECES CONTAINING 98%, & THE URINE 2%.

(119)TIN LABELED TRICYCLOHEXYLTIN HYDROXIDE ADMIN ORALLY TO RATS WAS 99.9% EXCRETED AFTER 9 DAYS, MOSTLY BY WAY OF THE FECES. AFTER ORAL ADMIN OF DIET CONTAINING 100 PPM TO RATS FOR APPROX 90 DAYS, THE LOWEST TIN LEVELS WERE IN THE BLOOD AND FAT AND THE HIGHEST IN THE KIDNEYS. TRICYCLOHEXYLTIN HYDROXIDE WAS THE PRIMARY TIN COMPOUND IN MUSCLE TISSUE 2 DAYS AFTER WITHDRAWAL OF PLICTRAN FROM THE DIET.

An acaricide (miticide); [Merck Index]

Not registered for current use in the U.S. [HSDB]

For Tricyclohexyltin (USEPA/OPP Pesticide Code: 101601) 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./

Non systemic acaricide with contact action. Used to control the motile phase of phytophagous mites on pome fruit, stone fruit, vines, hops, nuts, bush fruit, strawberries, vegetables, cucurbits and ornimentals. /Former use/

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

For the preparation of tricyclohexyltin chloride, the Kocheshkov redistribution reaction is not suitable. ... Two alternative routes are practiced for the manufacture of tricyclohexyltin chloride. The closely controlled reaction of cyclohexylmagnesium chloride and stannic chloride in a three-to-one molar ratio can be made to give the desired product in good yield. Another method involves 2 steps for the prepn. ... In the first step, butyltin trichloride reacts with 3 moles of cyclohexylmagnesium chloride forming butyltricyclohexyltin. This tetraorganotin then reacts with stannic chloride under mild conditions in an inert solvent, cleaving a butyl group and yielding tricyclohexyltin chloride and butyltin trichloride. The latter is recovered and recycled. ... Tricyclohexyltin chloride is converted to the hydroxide with sodium hydroxide.

GRIGNARD REAGENT IS REACTED WITH TIN TETRACHLORIDE.

Preprn: E.E. Kenaga U.S. Patent 3,264,177 (1966 to Dow)

USEPA/OPP Pesticide Code 101601; Trade Names: Plictran, Dowco 213.

'PLICTRAN 50 W', WETTABLE POWDER (500 G AI/KG); IN AFRICA, EUROPE AND THE MIDDLE EAST: 'PLICTRAN 25W', WETTABLE POWDER (250 G/KG); PLICTRAN 600F, SC (600 G/L). MIXTURES INCLUDE: DORVERT, SC (150 G CYHEXATIN + 50 G TETRADIFON/L).

Plictran 50W miticide; wettable powder, 50.0% cyhexatin (tricyclohexylhydroxystannane).

Ortho Plictran 50 Wettable Miticide; wettable powder, 50.0% cyhexatin (tricyclohexylhydroxystannane).

For more Formulations/Preparations (Complete) data for TRICYCLOHEXYLTIN HYDROXIDE (6 total), please visit the HSDB record page.

Transformation products, Acaricides, Insecticides

ACARICIDES

Developed from a joint project of Dow Chemical Co. and M&T Chemicals Inc. and introduced by Dow Chemical Co. (patents: US 3264177; US 3389048) development code: Dowco 213.

Plictran (cyhexatin) /is/ discontinued by Dow Chem Co.

Introduced into the U.S. market by Dow Chemical Company as Plictran.