2-Chloro-N-isopropylacetanilide Pathway Map

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This pathway was contributed by Valerie Anne Edwards, University of Minnesota BioC/MicE 5309.

2-Chloro-N-isopropylacetanilide (Propachlor) is an acetamide herbicide widely used to protect corn, onion, cabbage, rose bushes, and ornamental plants. This chemical dissipates primarily by biodegradation in the soil (Martin et al., 1999), or in water (Steen and Colette, 1989).

Two of the pathways share the same first step (Martin et al., 1999), and are intiated by Pseudomonas sp. PEM1, Acinetobacter sp. BEM2, and Pseudomonas sp. GH1 (Martin et al., 2000). The other pathway is begun by Moraxella sp. DAK3 and continued by Xanthobacter sp. MAB2, ATCC 49876 (Villarreal et al. 1991).

The following is a text-format 2-Chloro-N-isopropylacetanilide pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic (14k) format.

      2-Chloro-N-isopropylacetanilide                                    2-Chloro-N-isopropylacetanilide
           Pseudomonas sp. GCH1                                                 Moraxella sp. DAK3
           Pseudomonas sp. PEM1                                                         |
          Acinetobacter sp. BEM2                                                        | 2-chloro-N-isopropyl-
                     |                                                                  | acetanilide
                     |                                                                  | 1,2-dioxygenase
                     | 2-chloro-N-isopropylacetanilide                                  |
                     | reductive dehalogenase                                           v
                     |                                              2-Chloro-N-isopropylacetamide + Catechol
                     v                                                  Xanthobacter sp. MAB2          |
          N-Isopropylacetanilide --------------------------+                      |                    |
                     |                                     |                      |                    |
                     | N-isopropyl-                        | N-isopropyl-         v C                  |
                     | acetanilide                         | acetaniline          |                    |
                     | amidohydrolase                      | monooxygenase        v                    |
                     |                                     |                Carbon dioxide             v
                     v                                     v                                         to the
            N-Isopropylaniline    +   Acetate         Acetanilide                                 Nitrobenzene
                     |                   |                 |                                        Pathway
                     | N-isopropyl-      |                 | 
                     | aniline           |                 | acetanilide
                     | 1,2-dioxygenase   |                 | 1,2-dioxygenase
                     |                   |                 |
                     v                   |                 v
        Isopropylamine + Catechol        v       Acetamide + Catechol
              |             |            to         |           |
              |             |       Intermediary    |           |
        amine |             |        Metabolism     |           |
dehydrogenase |             |          (KEGG)       |           |
              v             v                       |           v
         Acetaldehyde     to the                    |         to the
              |        Nitrobenzene                 |      Nitrobenzene
              |          Pathway                    v        Pathway
              |                                   to the
              v                               Thioacetamide
              to                                 Pathway
         Intermediary
          Metabolism
            (KEGG)


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Page Author(s): Valerie Anne Edwards

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