Description
This nematocide is used as a sol fumigant prior to crop
cultivation. Mainly farmers and process operators
employed at pesticide plants are exposed.
Chemical Properties
clear yellowish to brownish liquid
Chemical Properties
1,3-Dichloropropene is a colorless to strawcolored liquid. Sharp, sweet, irritating, chloroform-like odor.
Uses
Widely used as a preplanting soil fumigant
for the control of nematodes
Uses
1,3-Dichloropropene is a soil fumigant /nematicide used mainly
for the pre-plant control of most species of nematodes and soil insect
pests in citrus, pineapples, deciduous fruits and nuts, grapes, berries and
field and nursery crops. The product contains equal amounts of E- and
Z-isomer. The Z-isomer is more biologically active than the E-isomer.
Uses
1,3-Dichloropropene (a technical-grade mixture of the cis-and transisomers) is used as a preplanting fumigant, mainly for the control of nematodes affecting the roots of plants, selected plant diseases, garden centipedes, wireworms, and weeds; as a solvent; and as an intermediate in the manufacture of 3,3-dichloro-1-propene and other pesticides. It is registered for use on all vegetable, fruit, and nut crops, all forage crops, tobacco, all fiber crops, and all nursery crops (EPA 1998). In Hawaii, 1,3-dichloropropene is used to control nematodes on pineapples at planting (Albrecht 1987). In 2009, three products containing 1,3-dichloropropene as an active ingredient were registered for restricted, non-residential use in the United States (EPA 2009). No products containing 1,3-dichloropropene are registered for use by homeowners (EPA 1998).
Production Methods
1,3-DCP is produced either by high-temperature chlorination
of propylene or from 1,3-dichloro-2-propanol by dehydration
with phosphoryl chloride or phosphorus pentoxide in
benzene. All commercial preparations of 1,3-DCP are mixtures
of the cis- and trans-isomers.
According to SRI Consulting, Dow AgroSciences LLC
(Freeport, Texas) is the only current manufacturer of 1,3-
DCP. Active registrants of 1,3-DCP pesticide formulations
include Dow AgroSciences LLC (Indianapolis, Indiana),Soil Chemicals Corporation (Hollister, California), and
Trical (Hollister, California).
General Description
A clear colorless liquid. Flash point 95°F. Denser (at 10.2 lb / gal) than water and insoluble in water. Vapors are heavier than air. Used to make other chemicals and as soil fumigant.
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
1,3-Dichloropropene reacts vigorously with oxidizing materials. Reacts with aluminum, active metals, and halogenated compounds. Also reacts with acids and thiocyanates. Corrosive to magnesium, magnesium alloys and aluminum alloys. Incompatible with some metal salts .
Health Hazard
VAPOR: Irritating to eyes, nose and throat. LIQUID: Will burn skin and eyes. Harmful if swallowed.
Fire Hazard
FLAMMABLE. POISONOUS GASES ARE PRODUCED IN FIRE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Toxic and irritating gases may be generated.
Agricultural Uses
Soil fumigant, Nematicide: This chemical is also used in combinations with
dichloropropanes as a soil fumigant to kill nematodes,
insects and fungus on cotton, potatoes, tobacco, sugar
beets, vegetables, grain, citrus planting sites, deciduous
fruit and nut-tree planting sites, and ornamental trees and
floral sites. Top four applications in California are on
sweet potatoes, carrots, wine grapes and outdoor propagation
nurseries. It is used on a wide variety of crops. Not
approved for use in EU countries. Actively registered
in the U.S.
Trade name
DURHAM NEMATOCIDE®[C];
FUMAZONE®[C]; NEMAGON®[C]; NEMEX®; PROKILL
NEMATOCIDE®[C]; TELONE®; TELONE II®;
TELONE II-B®; TELONE® EC DRIP; VIDDEN D®;
VORLEX®
Contact allergens
This nematocide is used as a soil fumigant prior to
crop cultivation. Farmers and process operators
employed at pesticide plants are mainly exposed
Mechanism of action
Soil fumigant that penetrates into the nematodes via mouth and cuticle. A non-specific inhibitor that affects multiple biological sites within the target pest.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic data. Poison
by ingestion and intraperitoneal routes.
Moderately toxic by skin contact. Mildly
toxic by inhalation. A strong irritant.
Mutation data reported. A pesticide. A
flammable liquid and dangerous fire hazard
when exposed to heat, flame, or oxidzers.
Reacts vigorously with oxidizing materials.
To fight fire, use water, foam, CO2, dry
chemical. When heated to decomposition it
emits toxic fumes of Cl-. See also ALLYL
COMPOUNDS and CHLORIDES.
Potential Exposure
Used as a soil fumigant prior to
planting crops, such as cotton, sugar beet, potatoes; used in
combinations with dichloropropanes as a soil fumigant.
Workers engaged in manufacture, formulation and application of this soil fumigant and nematocide.
Carcinogenicity
Technical-grade 1,3-dichloropropene (co
ntaining 1.0% epichlorohydrin as a stabilizer) is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. The technical-grade 1,3-dichloropropene used in the cancer studies in experimental animals was a mixture of cis- and trans-isomers and varied in purity and the stabilizer used (see Properties).
Metabolic pathway
Degradation of 14C-1,3-dichloropropene in aerobic
soils in the dark at 25℃ at concentration of
approximately 100 μg g
-1 results in the formation of 3-chloroallyl alchohol, 3-chloroacrylic acid, numerous
minor carboxylic acid metabolites, and carbon dioxide.
In addition, there is extensive incorporation of 14C
labeled material into the soil organic matter in the
soils. By a specific bacterium (Pseudomonas cichorii
170) which is isolated from soil, 1,3-dichloropropene is
degraded in different pathways from those of soil
degradation. The terminal degradate by this bacterium
is acetoaldehye which undergoes mineralization.
Shipping
UN2047 Dichloropropene, Hazard Class: 3;
Labels: 3-Flammable liquid.
Degradation
E-1,3-Dichloropropene (1) and Z-1,3-dichloropropene (2) degraded
rapidly in aqueous solution (independent of pH) under both dark and
light exposed conditions (25 °C), with DTW values of ca. 1-6 days. Hydrolytic
dechlorination reactions yielded E- and Z-3-chloroallyl alcohol (3,4)
and hydrochloric acid (5) as the major products. Further oxidation of
3 and 4 yielded E- and Z-3-chloroacrylic acid (6, 7) as minor products
(McCall, 1987; Milano et al., 1988; Batzer and Yoder, 1995).
1,3-Dichloropropene degraded in the vapour phase (with ozone and
hydroxyl radicals) to yield chloroacetaldehyde (8), formyl chloride (9) and
chloroacetic acid (10 (Tuazon et al., 1984). The estimated air photolysis
DT
50 was ca. 7-12 hours (Roby and Melichar, 1997).
Toxicity evaluation
In water hydrolyzes to
3-chloropropenol and chloride ion. Both isomers of
3-chloropropenol are toxic but less so than the parent
compound.
Incompatibilities
Vapor may form explosive mixture
with air. Incompatible with oxidizers (chlorates, nitrates,
peroxides, permanganates, perchlorates, chlorine, bromine,
fluorine, etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, and epoxides. May accumulate static electrical
charges, and may cause ignition of its vapors. Incompatible
with strong acids; oxidizers, aluminum or magnesium compounds; aliphatic amines; alkanolamines, alkaline materials;
halogens, or corrosives. Note: Epichlorohydrin may be
added as a stabilizer.
Toxics Screening Level
The initial threshold screening level (ITSL) for 1,3-dichloropropene is 20 μg/m3 with annual averaging time.
Waste Disposal
Incineration, preferably
after mixing with another combustible fuel. Care must be
exercised to assure complete combustion to prevent the
formation of phosgene. An acid scrubber is necessary to
remove the halo acids produced. 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.
Pesticide Type
Nematicide; Insecticide
