1,3-Dichloropropene, sold under diverse trade names, is an

organochlorine compound Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...

with the formula . It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It acts non-specifically and is in IRAC class 8A. It is widely used in the US and other countries, but is banned in 34 countries (including the

European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

Production, chemical properties, biodegradation

It is a byproduct in the chlorination of

propene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like od ...

to make

allyl chloride Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a c ...

. It is usually obtained as a mixture of the geometric isomers, called (''Z'')-1,3-dichloropropene, and (''E'')-1,3-dichloropropene. Although it was first applied in agriculture in the 1950s, at least two biodegradation pathways have evolved. One pathway degrades the chlorocarbon to

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

via chloroacrylic acid.

Safety

The TLV- TWA for 1,3-dichloropropene (DCP) is 1 ppm.Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. It is a contact irritant. A wide range of complications have been reported.

Carcinogenicity

Evidence for the

carcinogen A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...

icity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. In the US, the

Department of Health and Human Services The United States Department of Health and Human Services (HHS) is a cabinet-level executive branch department of the US federal government created to protect the health of the US people and providing essential human services. Its motto is ...

(DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. In California, the Office of Environmental Health Hazard Assessment has determined that 1,3-dichloropropene is a carcinogen, and in 2022 established a No Significant Risk Level (NSRL) of 3.7 micrograms/day. The

International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; ) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and coordinate research into the causes of cancer. It also cance ...

(IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.

Use

1,3-Dichloropropene is used as a pesticide in the following crops:

Contamination

The

ATSDR The Agency for Toxic Substances and Disease Registry (ATSDR) is a federal public health agency within the U.S. Department of Health and Human Services (HHS). The agency focuses on minimizing human health risks associated with exposure to hazar ...

has extensive contamination information available.

Market history

Under the brand name Telone, 1,3-D was one of

Dow AgroSciences Dow AgroSciences Limited liability company, LLC was a wholly owned subsidiary of the Dow Chemical Company specializing in not only agricultural chemicals such as pesticides, but also seeds and biotechnology solutions. The company was based in ...

's products until the merger into DowDuPont. Then it was spun off with

Corteva Corteva, Inc. (also known as Corteva Agriscience), headquartered in Indianapolis, Indiana, is a producer of products for seed and crop protection. The company produces herbicides, insecticides, fungicides, and biologicals (natural herbicides) tha ...

, and has been licensed to Telos Ag Solutions and is no longer a Corteva product.

References

ATSDR ToxFAQs: DichloropropenesUSGS Pesticide National Synthesis Project – Crop & Compound