1,3-Dichloropropene
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Names | |||
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Preferred IUPAC name
1,3-Dichloroprop-1-ene | |||
Other names
AQL Agrocelhone, DD92, 1,3-D, Dorlone, Nematox, Telone,[1][2] Nemex, cis-Dichloropropene, Di-Trapex CP, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 1,3-dichloropropylene, 3-D, DCP, 3-Chloroallyl chloride
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Identifiers | |||
3D model (
JSmol ) |
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.008.024 | ||
EC Number |
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KEGG | |||
MeSH | 1,3-dichloro-1-propene | ||
PubChem CID
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RTECS number
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UNII | |||
UN number | 2047 | ||
CompTox Dashboard (EPA)
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Properties | |||
C3H4Cl2 | |||
Molar mass | 110.97 g/mol | ||
Appearance | Colorless to straw-colored liquid | ||
Odor | sweet, chloroform-like | ||
Density | 1.217 g/mL (cis); 1.224 g/mL (trans) | ||
Melting point | −84.5 °C (−120.1 °F; 188.7 K) | ||
Boiling point | 104 °C (219 °F; 377 K) (cis); 112 °C (trans) | ||
2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C | |||
log P | 1.82 | ||
Vapor pressure | 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans) | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H226, H301, H302, H305, H311, H315, H317, H319, H331, H332, H335, H410 | |||
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P331, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 28 °C (82 °F; 301 K) | ||
> 500 °C (932 °F; 773 K) | |||
Explosive limits
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5.3% – 14.5% (80 °C) | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[3] | ||
REL (Recommended)
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Ca TWA 1 ppm (5 mg/m3) [skin][3] | ||
IDLH (Immediate danger) |
Ca [N.D.][3] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Dichloropropene, sold under diverse trade names, is an
Production, chemical properties, biodegradation
It is a byproduct in the
It is usually obtained as a mixture of the
Safety
The
Carcinogenicity
Evidence for the carcinogenicity 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 (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.[9] The International Agency for Research on Cancer (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.[8]
Use
1,3-Dichloropropene is used as a pesticide in the following crops:[10]
Crop | Pounds (lb) | Primary Pesticide? |
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Tobacco | 12,114,887 | Yes |
Potatoes | 12,044,736 | Yes |
Sugar Beets | 5,799,613 | Yes |
Cotton | 3,735,543 | Yes |
Peanuts | 3,463,003 | Yes |
Sweet Potatoes | 1,210,872 | Yes |
Onions | 674,183 | Yes |
Carrots | 531,752 | Yes |
Watermelons | 133,801 | No |
Cantaloups | 121,395 | No |
Cucumbers | 76,735 | No |
Strawberries | 71,753 | No |
Sweet Peppers | 28,247 | No |
Melons | 12,471 | No |
Blueberries | 3,090 | No |
Asparagus | 1,105 | No |
Contamination
The ATSDR has extensive contamination information available.[11]
Market history
Under the brand name Telone, 1,3-D was one of
References
- ^ PMID 14527332.
- ^ a b "Telone soil fumigant to be distributed by Telos Ag Solutions". Vegetable Growers News. 17 November 2020. Retrieved 6 July 2021.
- ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0199". National Institute for Occupational Safety and Health (NIOSH).
- ^ COMMISSION DECISION of 13 May 2022 concerning the non-approval of the active substance 1,3-dichloropropene, Official Journal of the European Union, 13 May 2022.
- ISBN 3527306730, retrieved 18 March 2022
- PMID 15381403.
- ^ a b "ToxFAQs – Letter A | Toxic Substance Portal | ATSDR".
- ^ "Proposition 65: No Significant Risk Level for 1,3-Dichloropropene (1,3-D)". oehha.ca.gov. 21 June 2022. Retrieved 26 October 2022.
- ^ "National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound". United States Geological Survey. Archived from the original on 10 April 2007.
- ^ "TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES" (PDF). Agency for Toxic Substances and Disease Registry. September 2008.