Naturally Occurring Organohalogen Compounds - A by Gordon W. Gribble

By Gordon W. Gribble

Despite the lengthy organization of organohalogen compounds with human actions, nature is the manufacturer of approximately 5,000 halogen-containing chemical substances. as soon as brushed aside as injuries of nature or isolation artifacts, organohalogen compounds signify an enormous and ever becoming classification of common items, in lots of circumstances displaying unheard of organic job. because the final entire evaluation in 1996 (Vol. sixty eight, this series), there were stumbled on an extra 2,500 organochlorine, organobromine, and different organohalogen compounds. those average organohalogens are biosynthesized through micro organism, fungi, lichen, vegetation, marine organisms of every kind, bugs, and better animals together with people. those compounds also are shaped abiogenically, as in volcanoes, wooded area fires, and different geothermal events.In a few cases, common organohalogens are exactly the comparable chemical substances that guy synthesizes for commercial use, and a few of the amounts of those common chemical substances a long way exceed the amounts emitted by way of man.

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By Gordon W. Gribble

Despite the lengthy organization of organohalogen compounds with human actions, nature is the manufacturer of approximately 5,000 halogen-containing chemical substances. as soon as brushed aside as injuries of nature or isolation artifacts, organohalogen compounds signify an enormous and ever becoming classification of common items, in lots of circumstances displaying unheard of organic job. because the final entire evaluation in 1996 (Vol. sixty eight, this series), there were stumbled on an extra 2,500 organochlorine, organobromine, and different organohalogen compounds. those average organohalogens are biosynthesized through micro organism, fungi, lichen, vegetation, marine organisms of every kind, bugs, and better animals together with people. those compounds also are shaped abiogenically, as in volcanoes, wooded area fires, and different geothermal events.In a few cases, common organohalogens are exactly the comparable chemical substances that guy synthesizes for commercial use, and a few of the amounts of those common chemical substances a long way exceed the amounts emitted by way of man.

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1 (382). Both chloroethyne and vinyl chloride are emitted from three soil types (coastal salt marsh, peatland, and a deciduous forest). Cl 10 O OH OH Fe(III) 58 Cl O Fe(III) Cl– O2 CH3Cl CH3CH2Cl –CO2 CH3CH2CH2Cl CH3CH2CH2CH2Cl Abiotic formation of organochlorines from catechol (382). 2 23 Volcanic Emissions A study of Mt. Etna, Vulcano, Kuju, and Satsuma-Iwojima volcanoes reveals the presence of several halogenated alkynes 59–77 (217). 13 Cl 74, 75 73 Br Cl2 77 76 Simple Organofluorines Following the early reports of chlorofluorocarbons (CFCs) in volcanic and drill well emissions (1), more recent work confirms these studies (216, 217), although the emission rates of CFCl3 and CF2Cl2 are very small compared to the anthropogenic sources of these compounds (383).

4 Terpenes 35 Br Cl Cl Cl Cl Br Br Br Cl 199 Br 200 Cl Cl M (or isomer) Many polyhalogenated monoterpenes have potent biological activity (1). In addition to cytotoxic activity, several compounds display insect repellent and antifeedant activity, and selective insect cell toxicity (480). To acquire sufficient quantities of these and other target metabolites for biological evaluation, the laboratory cultivation of marine algae – “bioprocess engineering” – is under intense exploration (481–483). 2 Alicyclic Monoterpenes The halogenated acyclic marine monoterpenes are often considered to be the biogenetic precursors of the alicyclic monoterpenes that are presented in this section.

N-C12H25Cl n-C13H26Cl n-C14H29Cl n-C15H31Cl n-C16H33Cl n-C17H35Cl 82 83 84 85 86 87 n-C18H37Cl n-C19H39Cl n-C20H41Cl n-C21H43Cl n-C22H45Cl n-C23H47Cl 88 89 90 91 92 93 n-C24H49Cl n-C25H51CI n-C26H53Cl n-C27H55Cl n-C28H57Cl n-C29H59Cl 94 95 96 97 98 99 An examination of several marine worms (Marenzellaria viridis, Polydora socialis, Scolelepsis squamata, Spiophanes bombyx, and Streblospio benedicti) has tentatively identified alkyl and alkenyl halides 100–105 (390). 2 25 Simple Functionalized Acyclic Organohalogens Several simple functionalized natural organohalogens do not reasonably fit into categories such as terpenes, alkaloids, or fatty acids (1) and are therefore included here.

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