Tricyclohexyltin hydroxide

Tricliloro-l, 2,2-trifluoroethane, 132 Tricresyl phosphates, 132 Tricyclohexyltin hydroxide, 132 Triethyl aluminum, 132 Triethylamine, 132 Triethyl phosphite, 132 Trifluorobromomethane, 132 Trifluoroethane, 132 Trifluoromethane, 132 Trifluralin, 132 Triisobutyl aluminum, 133 Trikem SA, 146... 

Tricyclohexyltin hydroxide is metabolized in vivo to inorganic tin via di- and monocyclohexyltin derivatives (502), and in vitro studies suggested that the major, metabolic reaction is carbon-hydroxylation of the cyclohexyl group (503). Studies in vivo using either tri-phenyl[ Sn]tin acetate (467) or triphenyl[" Sn]tin chloride (504) in rats showed that these compounds are metabolized to yield substantial amounts of di- and monophenyltin derivatives, although no significant quantities of hydroxylated metabolites have been identified (503) in this case. 

It has been well established that triphenyltin compounds are broken down photochemically to inorganic tin via the di- and monophenyltin derivatives both under laboratory (505, 506) and natural (507) conditions. In soil, triphenyltin acetate is converted microbiologically (505) into inorganic tin, as is tricyclohexyltin hydroxide (502). The latter compound is also photochemically broken down to inorganic tin (502, 508). 

Feeding of 160 mg triethyltin hydroxide/kg diet for 15 weeks was not fatal, but caused muscular weakness and some diet avoidance (Stoner etal. 1955) Acute oral LD50 of tricyclohexyltin hydroxide varies between 255 and 390 mg/kg BW dietary levels of 20 mg/kg had no measurable effect on growth, survival, or reproduction (Zuckerman etal. 1978)... 

Acute oral LD50 of 654 mg of tricyclohexyltin hydroxide (Smith 1978a)... 

Tin-containing compounds have been used in agriculture for many years as both fungicides (Chapter 4) and as acaricides. Tricyclohexyltin hydroxide and several related compounds (Figure 3.20), are very active against adult spider mites and are believed to act through an inhibition of oxidative phosphorylation. 

On the other hand, triphenyltin acetate and triphenyltin hydroxide were the first commercial products introduced during the early 1960s followed by triphenyltin chloride, tricyclohexyltin hydroxide, bis(trineophenyltin) oxide, and tricyclohexatin-1,2,4-triazole, respectively. Triphenyltin hydroxide was one of the recommended pesticides for rice and necessary for countries like Thailand where rice is a major component of both domestic and export markets (Visoottiviseth, 2001). 

Trialkyltin compounds have been shown to be effective agriculturally. Tributyltin oxide (III) has insecticidal and fungicidal activity, but generally has not been useful for plant protection due to phytotoxicity and volatility problems. Tricyclohexyltin hydroxide (TCTH, IV) has been an extremely effective acaricide.(3) Developed under the trade name Plictran, this compound was one of the first commercial acaricides. Another trialkyltin compound under development is hexakis (jS > j3 -dimethylphenylethyl)distannoxane (Vendex, V), which is also an effective acaricide. 

Examples of organotin compounds to have found applications as agrochemicals are PhsSiiX (OH or OCOMe) (antifungicide for crops) and tricyclohexyltin hydroxide, [(PhCMe2CH2)3Sn]20, and tricyclohexylstannyl-1,2,4-triazole (acaricides). 

SYNS DOWCO-213 EXT 27,395-X M 3180 PLICTRAN PLYCTRAN TCTH TRICYCLOHEXYLHYDROXYSTANNANE TRICYCLOHEXYLHYDROXTTIN TRICYCLOHEXYLTIN HYDROXIDE TRICYCLO-HEXYLZINNHYDROXID (GERMAN)... 

TRICYCLOHEXYLHYDROXYTIN see CQH650 TRICYCLOHEXYLTIN HYDROXIDE see CQH650 TRICYCLOHEXYLZINNHYDROXID (GERMAN) see CQH650... 

Branching at the a-carbon atom appears to confer enough steric hindrance to inhibit dehydration of the hydroxide. Tricyclohexyltin hydroxide, which is used as an acaricide under the name of Plictran, is stable up to about 125 °C when it loses water to give the oxide.3 Tri-t-butyltin hydroxide can be prepared from tris(di-t-butyltin oxide) as shown in Scheme 12-1, and loses water to give bis(tri-t-butyltin) oxide only when it is heated for several horns under vacuum at 200 °C. The properties of some triorganotin hydroxides and oxides are given in Table 12-1.15... 

While triphenyltin hydroxide (fentin hydroxide) in used as a potent fungicide, its saturated analogue, tricyclohexyltin hydroxide (34), is highly active against motile forms of plant-feeding mites (Kenaga, 1966 Allison el al., 1968). 

Tricyclohexyltin hydroxide can be prepared via the Grignard reaction, by reaction of cyclohexyl magnesium halide with stannic chloride. 

Triorganotins, Rj Sn X, have in-vitro fungicidal and antibacterial properties which may be used for crop protection. Trialkyltin compounds are phytotoxic, but triphenyltins are well tolerated by plants and maintain a high biocidal activity. Triphenyltin acetate or hydroxide and tricyclohexyltin hydroxide are now registered in the United States and in many European and Asian countries as pesticides, but are also used as chemo-sterilants and antifeedants in insect control. 

---