2,3-Dichloropropene
[CAS# 78-88-6]

Identification

• Classification: Chemical pesticide >> Herbicide >> Carbamate herbicide
• Name: 2,3-Dichloropropene
• Synonyms: 2,3-Dichloro-1-propene
• Molecular Formula: C₃H₄Cl₂
• Molecular Weight: 110.97
• CAS Registry Number: 78-88-6
• EC Number: 201-153-8
• SMILES: C=C(CCl)Cl

Properties

• Density: 1.204
• Melting point: 10 °C
• Boiling point: 94 °C
• Refractive index: 1.4601-1.4621
• Flash point: 10 °C
• Water solubility: <0.1 g/100 mL at 22 °C

Safety Data

• Hazard Symbols: GHS02;GHS08;GHS05;GHS07 Danger
• Risk Statements: H225-H341-H332-H312-H302-H335-H315-H318-H412
• Safety Statements: S16;S23;S26;S36/37/39;S61;S9

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Flammable liquids	Flam. Liq.	2	H225
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	4	H332
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 2047

Discovery and Applications

2,3-Dichloropropene is a chlorinated hydrocarbon that is commonly used in agriculture as a soil fumigant and insecticide. The discovery of 2,3-Dichloropropene dates back to the early 20th century when researchers were exploring the synthesis of chlorinated hydrocarbons for use in agriculture. It was first introduced as a commercial product in the 1940s, when demand for effective soil fumigants and pest control agents was increasing. 2,3-Dichloropropene:** Its development was driven by the need to increase crop yields and manage soil health more effectively. 2,3-Dichloropropene has two chlorine atoms on its backbone, making 2,3-Dichloropropene a highly reactive and effective pest control compound. It is a colorless to amber liquid with a characteristic pungent odor that can be used as a soil fumigant.

2,3-Dichloropropene is primarily used as a pre-planting soil fumigant. Its application involves injecting the liquid into the soil where it volatilizes and diffuses through the soil profile to kill nematodes, fungi, and other soil pests. This process helps create a sterile environment, reducing pest populations and preventing crop damage. It is particularly effective against nematodes, microscopic roundworms that attack plant roots, causing reduced crop yield and quality. By controlling nematode populations, 2,3-dichloropropene can improve soil conditions and promote healthier plant growth.

2,3-dichloropropene is injected into the soil using specialized equipment at a depth that ensures effective dispersion and minimal surface exposure. This approach helps to contain the fumigant in the soil, reducing environmental impact and human exposure. 2,3-dichloropropene can be combined with other soil fumigants, such as chloropicrin, to enhance its effectiveness against a wider variety of soil pests. These combination products offer a comprehensive solution for controlling soil pests, addressing multiple pest problems with just one treatment.

Due to its volatility, 2,3-dichloropropene can migrate through the soil and potentially contaminate groundwater if not managed properly. It is critical to follow application depth and control guidelines to minimize environmental impact. In many countries, including the United States, 2,3-dichloropropene is classified as a restricted-use pesticide, requiring certification and adherence to specific application procedures to ensure safe and effective use. These regulations are intended to protect applicators, bystanders, and the environment from potential adverse effects.

References

2022. Improved Synthesis of 5-(Chloromethyl)isoxazoles from Aldoximes and 2,3-Dichloropropene. Russian Journal of Organic Chemistry, 58(10).
DOI: 10.1134/s1070428022100268

2015. Reaction of 1,3- and 2,3-dichloroprop-1-enes with dipotassium propane-1,3-ditellurolate in the system hydrazine hydrate-KOH. Russian Journal of Organic Chemistry, 51(12).
DOI: 10.1134/s1070428015120234

2020. Effective Synthesis of Hard-To-Reach 3,4-Disubstituted Thiophene Derivatives Based on bis(2-chloropropenyl) Sulfide. Chemistry of Heterocyclic Compounds, 56(10).
DOI: 10.1007/s10593-020-02813-2