Cyhexatin, also known as tricyclohexyltin hydroxide is an

organometallic compound Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and ...

tin Tin is a chemical element; it has symbol Sn () and atomic number 50. A silvery-colored metal, tin is soft enough to be cut with little force, and a bar of tin can be bent by hand with little effort. When bent, a bar of tin makes a sound, the ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

Properties

Cyhexatin forms colorless crystals or white crystalline powder. It is practically insoluble in water. The powder is wettable by water.

Reactions

Cyhexatin is stable in aqueous suspensions in neutral and

alkaline In chemistry, an alkali (; from the Arabic word , ) is a basic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a soluble base has a pH greater than 7.0. The ...

conditions ( pH above 6), but reacts exothermically with

strong acids Acid strength is the tendency of an acid, symbolised by the chemical formula , to dissociate into a hydron (chemistry), proton, , and an anion, . The Dissociation (chemistry), dissociation or ionization of a strong acid in solution is effectivel ...

, acting as a base, to form salts. Reacts with strong oxidizers. Decomposes upon exposure to

ultraviolet light Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of th ...

to dicyclohexyltin oxide (which is not an analog of

ketones In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

because it exists as a polymer) and cyclohexylstannanoic acid . Contact with

metals A metal () is a material that, when polished or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. These properties are all associated with having electrons available at the Fermi level, as against no ...

may emit

flammable A combustible material is a material that can burn (i.e., sustain a flame) in air under certain conditions. A material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort ...

hydrogen Hydrogen is a chemical element; it has chemical symbol, symbol H and atomic number 1. It is the lightest and abundance of the chemical elements, most abundant chemical element in the universe, constituting about 75% of all baryon, normal matter ...

gas. Upon heating above it decomposes to bis(tricyclohexyltin) oxide , emitting irritating and toxic fumes and acrid smoke. :

Uses

Cyhexatin is used in paints. In

agriculture Agriculture encompasses crop and livestock production, aquaculture, and forestry for food and non-food products. Agriculture was a key factor in the rise of sedentary human civilization, whereby farming of domesticated species created ...

, cyhexatin is used as a

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

against insects, as well as parasitic

mites Mites are small arachnids (eight-legged arthropods) of two large orders, the Acariformes and the Parasitiformes, which were historically grouped together in the subclass Acari. However, most recent genetic analyses do not recover the two as eac ...

that attack plants, like

vegetables Vegetables are edible parts of plants that are consumed by humans or other animals as food. This original meaning is still commonly used, and is applied to plants collectively to refer to all edible plant matter, including flowers, fruits, ...

(e.g.

cucurbits The Cucurbitaceae (), also called cucurbits or the gourd family, are a plant family consisting of about 965 species in 101 genera.

), fruit trees (e.g. pome fruits,

stone fruits In botany, a drupe (or stone fruit) is a type of fruit in which an outer fleshy part (exocarp, or skin, and mesocarp, or flesh) surrounds a single shell (the ''pip'' (UK), ''pit'' (US), ''stone'', or ''pyrena'') of hardened endocarp with a seed ...

hops Hops are the flowers (also called seed cones or strobiles) of the hop plant ''Humulus lupulus'', a member of the Cannabaceae family of flowering plants. They are used primarily as a bittering, flavouring, and stability agent in beer, to whic ...

walnut A walnut is the edible seed of any tree of the genus '' Juglans'' (family Juglandaceae), particularly the Persian or English walnut, '' Juglans regia''. They are accessory fruit because the outer covering of the fruit is technically an i ...

strawberry The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown Hybrid (biology), hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit ...

vines A vine is any plant with a growth habit of trailing or wikt:scandent, scandent (that is, climbing) stems, lianas, or runners. The word ''vine'' can also refer to such stems or runners themselves, for instance, when used in wicker work.Jackson; ...

and

ornamentals Ornamental plants or ''garden plants'' are plants that are primarily grown for their beauty but also for qualities such as scent or how they shape physical space. Many flowering plants and garden varieties tend to be specially bred cultivars th ...

. It acts by inhibiting

mitochondrial A mitochondrion () is an organelle found in the cells of most eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is used ...

ATP synthase ATP synthase is an enzyme that catalyzes the formation of the energy storage molecule adenosine triphosphate (ATP) using adenosine diphosphate (ADP) and inorganic phosphate (Pi). ATP synthase is a molecular machine. The overall reaction catalyzed ...

, and is in

IRAC IRAC ( ) is an acronym that generally stands for: Issue, Rule, Application, and Conclusion. It functions as a methodology for legal analysis. The IRAC format is mostly used in hypothetical questions in law school and bar exams. Sections of an IR ...

group 12B). The chemical is not used in the United States.

Hazards and toxicity

Cyhexatin is not combustible, but decomposes upon heating to produce corrosive and toxic fumes. Some components of those fumes are oxidizers, thus, they can cause combustible materials to ignite, like wood, oil, some plastics, paper and clothes. Containers of cyhexatin may explode when heated. Cyhexatin is very toxic to aquatic life. Cyhexatin is not classified as a human carcinogen, but is classified as a teratogen. It is toxic by contact with skin, inhalation and ingestion. The compound and its fumes irritate and burn eyes. Contact with skin causes

pruritus An itch (also known as pruritus) is a sensation that causes a strong desire or reflex to scratch. Itches have resisted many attempts to be classified as any one type of sensory experience. Itches have many similarities to pain, and while both ...

and burns. Cyhexatin can be absorbed into the body through the skin, and skin should be washed immediately upon contact with this chemical. Inhalation of its fumes causes irritation of the

respiratory system The respiratory system (also respiratory apparatus, ventilatory system) is a biological system consisting of specific organs and structures used for gas exchange in animals and plants. The anatomy and physiology that make this happen varies grea ...

, coughing, headache, dizziness and sore throat. It can cause abdominal pain,

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...

, nausea and vomiting. It causes damage to

kidneys In humans, the kidneys are two reddish-brown bean-shaped blood-filtering organs that are a multilobar, multipapillary form of mammalian kidneys, usually without signs of external lobulation. They are located on the left and right in the retro ...

and

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

, as well as

nervous system In biology, the nervous system is the complex system, highly complex part of an animal that coordinates its behavior, actions and sense, sensory information by transmitting action potential, signals to and from different parts of its body. Th ...

. Cyhexatin is a

central nervous system depressant Depressants, also known as central nervous system depressants, or colloquially known as "downers", are drugs that lower neurotransmission levels, decrease the electrical activity of brain cells, or reduce arousal or stimulation in various are ...

References

{{reflist Organotin compounds Acaricides Cyclohexyl compounds