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
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haloalkane | | haloalkane
dehalogenase | | dehalogenase
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v v
trans-3-Chloro-2-propene-1-ol cis-3-Chloro-2-propene-1-ol
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alcohol | | alcohol
dehydrogenase | | dehydrogenase
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trans-3-Chloroallyl aldehyde cis-3-Chloroallyl aldehyde
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aldehyde | | aldehyde
dehydrogenase | | dehydrogenase
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trans-3-Chloroacrylic acid cis-3-Chloroacrylic acid
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v v
to the to the
trans-3-Chloroacrylic cis-3-Chloroacrylic
acid Pathway acid Pathway
Page Author(s): Yichiou Wan
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