Description
Diallate is a brown liquid. Molecularweight = 270.21; Boiling point =150℃ at 9 mmHg;Freezing/Melting point = 25-30℃. Hazard Identification(based on NFPA-704 M Rating System): Health 2,Flammability 0, Reactivity 0. Slightly soluble in water;solubility = 14 mg/L at 25℃.
Chemical Properties
Diallate is a brown liquid.
Uses
Preemergent, selective herbicide used to control wild oats and blackgrass in barley,
corn, flax, lentils, peas, potatoes, soybeans and sugar beets.
Uses
Diallate is a pesticide used to treat fruits and vegetables. Environmental wastewater pollutant.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.
Definition
ChEBI: Diallat is a tertiary amine.
Production Methods
Di-allate is commercially produced through a synthesis process that centres on the use of 1,2,3-trichloropropene as a key intermediate. This compound, valued for its high reactivity and purity, undergoes a reaction with diisopropylthiocarbamate to form the active herbicidal ingredient. The process involves precise control of temperature and solvent conditions to ensure the correct formation of the di-allate structure.
General Description
Used as an 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.
Reactivity Profile
DIALLATE 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.
Mechanism of action
Selective, inhibits lipid metabolism and thus the development of seedling shoots and roots
Safety Profile
Poison by ingestion.
Moderately toxic by skin contact.
Questionable carcinogen with experimental
carcinogenic and tumorigenic data. Mutation
data reported. When heated to
decomposition it emits very toxic fumes of
Cl-, NOx, and SOx. See also
CARBAMATES and ALLYL
COMPOUNDS.
Potential Exposure
A thiocarbamate herbicide. The slow
release of poisonous gases from hydrolysis of many thio
and dithiocarbamates requires the use of respirators during
handling. Poisoning can also occur by ingestion and
absorption through the skin. Diallate is potential danger to
those involved in the manufacture, formulation and applica-
tion of this re-emergence herbicide.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove fromexposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing hasstopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Environmental Fate
Soil. Soil metabolites include 2,3-dichloroallyl alcohol, 2,3-dichloroallyl mercaptan
(Hartley and Kidd, 1987) and carbon dioxide (Smith, 1988). The formation of the alcohol
occurs via hydrolysis of the ester linkage and transthiolation of the allylic group (Kaufman,
1967). In an agricultural soil, 14CO2 was the only biodegradation identified; however, bound
residue and traces of benzene and water-soluble radioactivity were also detected in large
amounts (Anderson and Domsch, 1980). The reported half-lives in soil range from 2 to 4
weeks to (Smith and Fitzpatrick, 1970) to approximately 30 days (Hartley and Kidd, 1987).
Diallate did not migrate deeper than 5 cm on test field plots (Smith, 1970). In four
microbially-active agricultural soils, the half-life was 4 weeks but in sterilized soil the
half-life was 20 weeks (Anderson and Domsch, 1976).
Plant. In plants, diallate is metabolized and carbon dioxide is released (Hartley and
Kidd, 1987). Diallate undergoes cis/trans isomerization and oxidative cleavage when
irradiated at 300 nm forming 2,3-dichloroacrolein and 2-chloroacrolein as products (Ruzo
and Casida, 1985).
Photolytic. Irradiation of diallate was also conducted in oxygenated chloroform or
water until a 10% conversion was obtained. Products formed included acetaldehyde, 2,3-
dichloroacrolein and trace amounts of 2-chloroacrolein (Ruzo and Casida, 1985).
Chemical/Physical. Emits toxic fumes of chlorine, nitrogen and sulfur oxides when
heated to decomposition (Sax and Lewis, 1987). Though no products were reported, the
calculated hydrolysis half-life at 25°C and pH 7 is 6.6 years (Ellington et al., 1988).
storage
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with diallateyou should be trained on its proper handling and storage.Store in tightly closed containers in a cool, well-ventilatedarea away from alkalies. Where possible, automaticallypump liquid from drums or other storage containers to process containers. A regulated, marked area should be established where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045.
Shipping
UN2992 Carbamate pesticides, liquid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
hiocarbamate esters are combustible.
They react violently with powerful oxidizers such as
calcium hypochlorite. 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. Many
materials in this group 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
thiocarbamates with aldehydes, nitrides, and hydrides.
Thiocarbamates are incompatible with acids, peroxides, and
acid halides.
Waste Disposal
Land burial is acceptable for
small quantities. Larger quantities can be incinerated
.
In accordance with 40CFR165, follow recommendations
for the disposal of pesticides and pesticide containers. Must
be disposed properly by following package label directions
or by contacting your local or federal environmental control
agency, or by contacting your regional EPA office. Consult
with environmental regulatory agencies for guidance
on acceptable disposal practices. Generators of waste
containing this contaminant (≥100 kg/mo) must conform
with EPA regulations governing storage, transportation,
treatment, and waste disposal.
