cis- and trans- 1,3-Dichloropropene (gamma-Chloroallylchloride or 1,3-Dichloropropylene) are major active ingredients of Shell D-D and Tolone II, commercial products for control of plant-parasitic nematodes. 1,3-Dichloropropenes which evaporate from soil go into the atmosphere and have a significant effect on the total air pollution caused by chlorinated hydrocarbons in The Netherlands (Van Rijn et al., 1995. Handbook Bestrijdingsmiddelen: gebruik & milieu-effecten, p.629-632). Shell D-D and Tolone II also represent an important class of carcinogenic water pollutants.
Both the cis- and trans- isomers of 1,3-Dichloropropene can be converted to the corresponding 3-Chloro-2-propene-1-ols and 3-Chloroacrylic acids (Roberts et al., 1976. Pestic. Sci. 7:325-335). These pathways are found in Pseudomonas cichorii strain 170 (Poelarends et al., 1998). The first step of these pathways, hydrolysis of 1,3-Dichloropropenes to 3-Chloro-2-propene-1-ols, can also take place abiotically in soils (Castro et al., 1966. J. Agric. Food Chem. 14:69-70) (Van Dijk, 1974. Agro-Ecosystems 1:193-204).
The following is a text-format of 1,3-Dichloropropene pathway maps. Follow the links for more information on compounds or reactions. This map is also available in graphic (7k) format.
trans-1,3-Dichloropropene cis-1,3-Dichloropropene Pseudomonas cichorii strain 170 Pseudomonas cichorii strain 170 | | | | haloalkane | | haloalkane dehalogenase | | dehalogenase | | v v trans-3-Chloro-2-propene-1-ol cis-3-Chloro-2-propene-1-ol | | | | alcohol | | alcohol dehydrogenase | | dehydrogenase | | | | trans-3-Chloroallyl aldehyde cis-3-Chloroallyl aldehyde | | | | aldehyde | | aldehyde dehydrogenase | | dehydrogenase | | | | trans-3-Chloroacrylic acid cis-3-Chloroacrylic acid | | | | | | | | | | v v to the to the trans-3-Chloroacrylic cis-3-Chloroacrylic acid Pathway acid Pathway
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