Chlorinated camphene toxicity

The purpose of this work was to determine the toxicity to mosquito larvae of insecticide spray residues. That certain insecticides are translocated in plants (4, 5) adds impetus to this study. Fresh orchard fruit sprayed or dusted with preparations containing parathion (0,0-diethyl O-p-nitrophenyl thiophosphate), tetraethyl pyrophosphate (TEPP, HEPP), DDD [2,2-bis(p-chlorophenyl)-l,l-dichloroethane], DDT [2,2-bis(p-chlorophenyl)-l,l,l-trichloroethane], chlorinated camphene, and basic lead arsenate were shipped from California to Yonkers, N. Y., by air express for bioassay. 

Different samples of chlorinated camphene containing from 62 to 72% of chlorine all give the same infrared spectra. However, the toxicity to flies reaches a maximum at a chlorine content of 67 to 69% and drops off rapidly below 60% and above 72%. From the results of both the infrared spectroscopic examination and the fly-toxicity tests given below, it is concluded that the organic-chlorine compound in the fat was essentially unchanged toxaphene. 

Tbxaphene is a mixture of at least 670 chlorinated camphenes differences in toxicity have been observed for various toxaphene fractions or components. ... 

A group of highly chlorinated polycyclic insecticides, exemplified by heptachlor (143) and aldrin (144), is prepared from hexachlorocyclopentadiene and cyclopentadiene. The y-isomer (lindane, 145) of hexachlorocyclohexane (HCH) is the toxic component of HCH, first prepared by Michael Faraday. Toxaphene consists of a complex mixture of chlorinated camphenes, of which 146 represents a particularly toxic isomer. 

Since toxaphene is a mixture of 670 chlorinated camphenes, some have greater toxicity than technical grade toxaphene alone. Toxaphene components A and B have been shown to have 6 and 14 times greater toxicity than the technical mixture, respectively. Component A is a mixture of... 

DDT was first synthesized in 1874 and its insecticidal properties discovered in 1939. Technical DDT is a stable, white, amorphous powder composed of up to 14 analogs and isomers. In 1942, hexachlorocyclohexane (benzene hexachloride) was discovered to be an effective and simple insecticide. Of its isomers, y-HCH has the greatest insecticidal activity and is marketed as lindane, whereas a-HCH and )3-HCH are more toxic to mammals. Chlordane, a mixture of terpenoid compounds, was discovered in 1945 to be a highly effective residual insecticide. In 1948, the most active principle of chlordane, termed heptachlor, was developed, along with two other cyclodiene derivatives, aldrin and dieldrin. It has been subsequently shown that microbial conversion of heptachlor in the environment yields heptachlor epoxide, which exhibits toxicity equal to or greater than that of the parent compound whereas photochemical conversion yields the equally toxic photoheptachlor. Also during 1948, a product obtained by the chlorination of turpentine and containing a considerable number of chlorinated camphenes was sold as toxaphene. 

Toxaphene (CioHio(- 18) is a mixture of polychlorinated camphenes (bicyclic terpenes). Currently in restricted use as an insecticide, it is toxic to fish, birds and wildlife and may be fatal to shrimp, and crab, etc. (ref. 103, p. 26). Its toxicity and routes of entry in mammals are typical of the cyclic chlorinated hydrocarbons as a class ... 

Figure 4. Products (middle row) of camphene chlorination in the dark (15, 16) and toxic compounds (bottom row) recently isolated from toxaphene...

---