2-chlorotoluene, degradation

Pierce et al. [124,125] reported that P. cepacia and several other Pseudomonas species were capable of utilizing mono- and dichlorinated toluenes as the sole source of carbon and energy. These strains contained plasmids of about 45 kilobase, which coded for chlorotoluene degradation. Restriction analysis showed that these plasmids, although of similar size, were not identical. 

Additional limitations. Other limitations have been enconntered (a) the formation of the inhibitory protoanemonin from 4-chlorocatechols (Blasco et al. 1995) and (b) the ineffectiveness of cycloisomerases reqnired for effective degradation of 2-chlorotoluene (Polhnann et al. 2005). An example of this limitation is given later, and in the degradation of 3-flnorobenzoate in Part 3 of this chapter. 

Pollmann K, V Wray, DH Pieper (2005) Chloromethybnuconolactones as critical metabolites in the degradation of chloromethylcatechols recalcitrance of 2-chlorotoluene. J Bacteriol 187 2332-2340. 

Chlorinated aromatic compounds are mi or environmental pollutants, because they are often released in substantial quantities. They are toxic and resistant to degradation, and accumulate in sediment and biota. Although some compovmds are degraded only slowly b7 soil and aquatic microorganisms, others are metabolized relatively quickly. There have been many studies on the ability of soil and aquatic microorganisms to dissimilate chlorinated aromatic hydrocarbons, such as chlorotoluenes [35,36], chlorobenzenes [37-42], chlorobenzoates [43-50], chlorophenols [51-66], chloroacetamide [67], 4-chlorophenylacetate [33,68], and chlorophenoxyacetates [69-83]. 

Also obtained by degradation of 6-chloro-2,3-diphenylbenzofuran with chro-minm trioxide in boiling acetic acid during 40 min or 2 h, followed by saponification of the 2-benzoyloxy-4-chloro-benzophenone so formed with 2 N or 4 N sodium hydroxide in refluxing aqueous ethanol for 1 h or 15 min [44,515]. Preparation by reaction of 4-chloro-2-methoxybenzoyl chloride (SM) with benzene in the presence of aluminium chloride at r.t. [6] according to [14]. SM was obtained from 2-amino-4-chlorotoluene by a four-step synthesis. 

---