1,3 Dichloropropene

Synonyms 1,3-DCP a-chloroallyl chloride 1,3-dichloropropylene Telone Telone II DD fumigants 

Physical Form. Clear to amber-colored liquid 

Widely used as a preplanting soil fumigant for the control of nematodes 

Toxicology. 1,3-Dichloropropene (1 3-DCP) is an irritant of the eyes, mucous membranes, and skin exposures in animals have been associated with contact hypersensitivity and damage to the nasal tissues, lungs, liver, kidneys, and urinary bladder. It is considered to be carcinogenic to experimental animals. 

A truck spill in 1985 resulted in exposure of an estimated 80 people. Signs and symptoms were headache in six persons, mucous membrane irritation in five, dizziness in five, and chest discomfort in four. Eleven of 41 persons tested had slightly elevated SCOT and/or SGPT values. In 28 persons interviewed 12 weeks after exposure, complaints were headache in 12, abdominal discomfort in 6, chest discomfort in 5, and malaise in 5. In one case the diagnosis was pneumonia, based on persistent dyspnea and cough. 

---

The dkect high temperature chlorination of propylene continues to be the primary route for the commercial production of aHyl chloride. The reaction results in aHyl chloride selectivities of 75—80% from propylene and about 75% from chlorine. Additionally, a significant by-product of this reaction, 1,3-dichloropropene, finds commercial use as an effective nematocide when used in soil fumigation. Overall efficiency of propylene and chlorine use thus is significantly increased. Remaining by-products include 1,2-dichloropropane, 2-chloropropene, and 2-chloropropane. 

Chemical Designations - Synonyms 1,3-Dichloropropene Telone Chemical Formula ... 

TELONE , 1,3-dichloropropene + chloropicrin, 125 TELURA , naphthas, 125 Teniephos, 125 TEMIK , aldicarb, 125 TEMPERA , fuel oils, 125 Temiessee Depailnient of Agriculture, 298 Temiessee Depailnient of Environment and Consei vation, 298 Temiessee Depailnient of Labor and Workforce Development, 298... 

The major by-products are cis- and trans- 1,3-dichloropropene, which are used as soil fumigants. 

Prepn of the cis isomer is by boiling cis-1,3-dichloropropene-(l) with LiAlH4 in diisopropyl ether. The trans isomer is similarly prepd using trans-1,3-dichioropropene-(l). Expl limits in air are 4.5 to 16%, and the flash pt is —6° for both isomers... 

Maddy KT, Fong HR, Lowe JA, et al. 1982. A study of well water in selected California communities for residues of 1,3-dichloropropene, chloroallyl alcohol and 49 organophosphate or chlorinated hydrocarbon pesticides. Bull Environ Contam Toxicol 29 354-359. 

The degradation of 2- and 3-chloroacrylate displays novel features. The degradation of 2-chloro-acrylate by Burkholderia sp. strain WS is initiated by a 2-haloacrylate reductase with the formation of (5)-2-chloropropionate that undergoes dehalogenation to (J )-lactate (Kurata et al. 2005). The degradation of 1,3-dichloropropene by Pseudomonas pavonaceae (cichorii) strain 170 involves a series of steps by which tra 5 -3-chloroacrylate is formed (Poelarends et al. 1998). This was degraded... 

Poelarends GJ, M Wilkens, MJ Larkin, JD van Elsas, DB Janssen (1998) Degradation of 1,3-dichloropropene by Pseudomonas cichorii 170. Appl Environ Microbiol 64 2931-2936. 

Chan and Li reported that conjugated 1,3-butadienes were produced in moderate yields when carbonyl compounds reacted with 1,3-dichloropropene and zinc in water (Eq. 8.29).61 The use of 3-iodo-1-chloropropene instead of 1,3-dichloropropene greatly improved the yields. When the reactions were interrupted after their initial allyla-tions, subsequent base treatment of the intermediate compounds produced vinyloxiranes in high yields. Similarly, reactions of carbonyl compounds with 3-iodo-2-chloromethyl-l-propene followed by base treatment produced 2-methylenetetrahydrofurans (Eq. 8.30).62 Thus, the 3-iodo-2-chloromethyl-l-propene served as a novel trimethylene-methane equivalent.63... 

In cis and trans -1, 3 dichloropropenes, the skew form is again more stable (hi the Newman formula for this compound, the CHC1 group would be in place of CH2 group). 

---