两种主要毒杀芬成分的合成及其光稳定性。,Journal of Agricultural and Food Chemistry

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两种主要毒杀芬成分的合成及其光稳定性。
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2005 Dec 28 , DOI: 10.1021/jf051451b
Mehmet Coelhan ₁ , Martin Maurer ₁

Affiliation

2-endo，3-exo，5-endo，6-exo，8,9,10-七氯硼烷（B7-1001，Hp-Sed）和2-endo，3-exo，5-endo，6-的合成描述了exo，8,9,9,10-八氯硼烷（B8-1412）。这两种化合物都是毒杀芬的一种成分，毒杀芬是一种过去已被广泛使用的杀虫剂。B7-1001是重要的毒杀芬同源物，占处理过的湖泊鱼类和沉积物样品中总毒杀芬浓度的99％。B8-1412也是生物区系样品中毒杀芬污染的重要组成部分。合成化合物时，通过还原著名的毒杀芬组分P 32（B7-515，2,2），可以得到2-exo，3-endo，6-endo，8,9,10-六氯硼烷（B6-913）。（5-内，6-外，8、9、10-七氯硼烷），其本身是从（+）-樟脑的氯化产物中分离出来的。对B6-913进行氯化处理可得到B7-1001，产率为49.5％，在反应混合物中也检测到了P 32和其他四种七氯硼烷。通过MS和NMR阐明了两个七氯硼烷的结构为2-exo，3-endo，6-endo，8,9,9,10-七氯硼烷（B7-1461）和2-exo，3,3,6- end，8,9,10-七氯硼烷（B7-1303）。从2-exo，3-endo，6-endo，8，9，9，10-七氯硼烷的氯化获得的产物混合物中分离出B8-1412。在λ= 254 nm处的光解实验表明，B6-913是光化学上研究的七种毒杀芬化合物中最稳定的化合物，在（1/2）时为213 h。B7-1001的at（1/2）为82 h，是第二稳定的化合物。B8-1412的降解速度比B7-1001更快，为（1/2）28.8h，但仍比P 50稳定得多（B9-1679、2-endo，3-exo，5-endo， 6-exo，8,8,9,10,10-九氯硼烷）的（1/2）为9.4 h，尽管它是非常持久的化合物而享有盛誉。在相同的实验条件下，六氯苯（HLB）和八氯二苯并二恶英（OCDD）的消耗非常迅速，t（1/2）= 0.0025和0.0015 h。

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Synthesis of two major toxaphene components and their photostabilities.

The synthesis of 2-endo,3-exo,5-endo,6-exo,8,9,10-heptachlorobornane (B7-1001, Hp-Sed) and 2-endo,3-exo,5-endo,6-exo,8,9,9,10-octachlorobornane (B8-1412) is described. Both compounds are components of toxaphene, an insecticide that has been widely used in the past. B7-1001 is an important toxaphene congener, comprising up to 99% of total toxaphene concentrations found in fish and sediment samples from treated lakes. B8-1412 is also a significant component of toxaphene contamination in samples from biota. In synthesizing the compounds, 2-exo,3-endo,6-endo,8,9,10-hexachlorobornane (B6-913) was obtained by reduction of the well-known toxaphene component P 32 (B7-515, 2,2,5-endo,6-exo,8,9,10-heptachlorobornane), which was itself isolated from the chlorination products of (+)-camphene. Chlorination of B6-913 provided B7-1001 in 49.5% yield, and P 32 and four other heptachlorobornanes were also detected in the reaction mixture. Structures of two of the heptachlorobornanes were elucidated by MS and NMR as 2-exo,3-endo,6-endo,8,9,9,10-heptachlorobornane (B7-1461) and 2-exo,3,3,6-endo,8,9,10-heptachlorobornane (B7-1303). B8-1412 was isolated from the product mixture obtained by chlorination of 2-exo,3-endo,6-endo,8,9,9,10-heptachlorobornane. Photolysis experiments at lambda = 254 nm revealed that B6-913 is photochemicaly the most stable compound of the seven toxaphene compounds studied, with a t(1/2) of 213 h. B7-1001, having a t(1/2) of 82 h, was the second most stable compound. B8-1412 was degraded more rapidly, with a t(1/2) of 28.8 h, than B7-1001, but was still much more stable than P 50 (B9-1679, 2-endo,3-exo,5-endo,6-exo,8,8,9,10,10-nonachlorobornane), which had a t(1/2) of 9.4 h, despite its reputation as a very persistant compound. Under the same experimental conditions hexachlorobenzene (HLB) and octachlorodibenzodioxine (OCDD) were consumed very quickly with t(1/2) = 0.0025 and 0.0015 h, respectively.

更新日期：2017-01-31

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