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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