1,3-Dichloropropene Family Pathway Map

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This pathway was contributed by Yichiou Wan, University of Minnesota.

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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Page Author(s): Yichiou Wan

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