Description
Cycloate is a herbicide used to control grasses and some broadleaved weeds. It is moderately soluble in water but insoluble in many organic solvents. It is a highly volatile substance. Cycloate may be moderately persistent in soil and water systems depending on environmental conditions. It is moderately toxic to mammals, an acetylcholinesterase inhibitor and neurotoxin. It is also moderately toxic to most fauna and flora.
Chemical Properties
Cycolate is an oily, clear, or amber to yellow
liquid. Aromatic odor;
Uses
Herbicide used to control several broad-leaved weeds and many annual grasses in
sugar beets, table beets and spinach
Production Methods
Cycloate is commercially produced through the synthesis of S-ethyl-N-cyclohexylthiocarbamate. The process typically involves reacting cyclohexylamine with carbon disulfide to form cyclohexyl dithiocarbamate, which is then alkylated with ethyl chloride or a similar ethylating agent under controlled conditions to yield cycloate. This reaction is carried out in an organic solvent with a base to neutralise the byproducts.
Definition
ChEBI: Cycloate is a primary aliphatic amine.
General Description
Colorless liquid with an aromatic odor. Used as a selective systemic herbicide.
Air & Water Reactions
Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids or alkalis.
Reactivity Profile
CYCLOATE is a thiocarbamate ester. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Flammability and Explosibility
Non flammable
Agricultural Uses
Herbicide: Used to control broadleaf weeds, annual and perennial grasses and nutgrass in spinach, beets, and sugar
beets. Not approved for use in EU countries. Actively
registered in the U.S.
Trade name
ETSAN®; EUREX®; R-2063®; RO-
NEET®; RO-NEET®-6E; RO-NEET® 10G; RONIT®;
SABET®
Mechanism of action
Selective, systemic absorbed by roots and coleoptiles. Lipid synthesis inhibitor.
Potential Exposure
Cycolate is a thiocarbamate herbicide
used to control broad leaf weeds, annual and perennial
grasses and nutgrass in spinach, beets, and sugar beets.
Environmental Fate
Soil. The reported half-life in soil is approximately 4–8 weeks (Hartley and Kidd,
1987)
Groundwater. According to the U.S. EPA (1986) cycloate has a high potential to leach
to groundwater
Plant. Cycloate is rapidly metabolized in sugarbeets to carbon dioxide, ethylcyclohexylamine, sugars, amino acids and other natural constituents (Humburg et al., 1989)
Chemical/Physical. In the gas phase, cycloate reacts with hydroxyl and NO3 radicals
but not with ozone. With hydroxy radicals, cleavage of the cyclohexyl ring was suggested
leading to the formation of a compound tentatively identified as C2H5(CHO)NC(O)SC2H5.
The calculated photolysis lifetimes of cycloate in the troposphere with hydroxyl and NO3
radicals are 5.2 hours and 1.4 days, respectively (Kwok et al., 1992).
Shipping
UN3082 Environmentally Hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz-
ardous material, Technical Name Required
Incompatibilities
Cycolate reacts violently with powerful
oxidizers such as calcium hypochlorite. Thiocarbamate
esters are combustible. Poisonous gases are generated by
the thermal decomposition of thiocarbamate compounds,
including carbon disulfide, oxides of sulfur, oxides of nitro-
gen, hydrogen sulfide, ammonia, and methylamine. Thio
and dithiocarbamates slowly decompose in aqueous solu-
tion to form carbon disulfide and methylamine or other
amines. Such decompositions are accelerated by acids.
Flammable gases are generated by the combination of thio-
carbamates with aldehydes, nitrides, and hydrides.
Thiocarbamates are incompatible with acids, peroxides, and
acid halides.
Waste Disposal
Do not discharge into drains
or sewers. Dispose of waste material as hazardous waste
using a licensed disposal contractor to an approved landfill.
Consult with environmental regulatory agencies for guid-
ance on acceptable disposal practices. Incineration with
effluent gas scrubbing is recommended. Containers must be
disposed of properly by following package label directions
or by contacting your local or federal environmental control
agency, or by contacting your regional EPA office.
