Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Halogenated hydrocarbon doai
Patent
1991-05-03
1993-12-14
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Halogenated hydrocarbon doai
514519, 514715, 514729, 514755, A01N 2904, A01N 3100, A01N 3114, A01N 3734
Patent
active
052703452
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Polychlorinated cyclic hydrocarbons have been known for many years as good insectcides and many of them have been widely used in the past. Such insecticides as DDT, dieldrin, endrin, chlordane, lindane, heptaclor, aldrin, and toxaphene are examples. As the use of these compounds became more widespread and continued for several years, evidence mounted that these compounds were extremely stable to biodegradation and were found to be accumulating in the tissues of animals, birds and fishes, and therefore presumably in man, with toxic effects. As a result, the use of these obviously good insecticides has fallen into disfavor and actually has been banned in many instances. The need for strong pesticides which are not toxic to animals and do not bioaccumulate in the fat and tissues of animals is quite evident and has attracted much attention among researchers, but with very little success.
THE PRIOR ART
As noted above the class of polychlorinated cyclic hydrocarbons is well known in the art and the effect of such compounds on pests is well documented in the literature. It is also known in the art to dechlorinate a polychlorinated hydrocarbon by subjecting it to strong ultraviolet light. Such a process is inefficient because of the large volume of solvents required and the high energy necessary for the generation of a useful ultraviolet light. Yields were low and the cost of the dehalogenated compounds often ran as much as ten times that of the corresponding parent compound.
SUMMARY OF THE INVENTION
This invention relates to a class of novel compositions containing polychlorinated cyclic hydrocarbons having an endomethylene bridged structure, to novel compounds within this group, and to methods of making such compounds. The compounds are characterized generally as being strong or effective pesticides which do not accumulate, or accumulate slowly and not above acceptable limits in the tissues of animals, including man, fishes and fowl. Thus they avoid the environmental problem of bioaccumulation which has eliminated or restricted the use of most polychlorinated pesticides, e.g. Toxaphene, DDT, Dieldrin, Heptaclor, Aldrin and the like.
Bioaccumulation appears to be the ultimate reason for restricting use of highly toxic pesticides, which is caused at least in part by the stability of the compounds, i.e., their resistance to breakdown into less toxic or non-toxic degredation products. Thus, faster biodegredation should result in lower bioaccumulation of the toxic chemicals in cells and tissue of the hosts.
We have found that the relatively non-bioaccumulative compounds of this invention can be made by replacing one or more halogen (chlorine) atoms with a hydrogen on a polyhalogenated cyclic hydrocarbon to make a less halogenated compound which we have found to possess excellent pesticide or repellent activity, usually at least equal to the parent compound in such activity and sometimes even better, but at the same time being less stable to biodegredation and consequently more easily converted into degredation products which are not so environmentally undesirable. The result is an effective pesticide, especially insecticide, which does not bioaccumulate to toxic levels in the host cells or tissue of mammalian species, fowl or fish.
Generally speaking, proton exchange under the influence of ultraviolet light is known as a means of replacing a halogen atom with a hydrogen atom in an organic molecule but the efficiency is known to be low and the product yield is unsatisfactory considering the large amount of energy consumed in the process. We have found a method of increasing the efficiency to acceptable levels, as described in greater detail herein. We have also found other syntheses for making the desired compound which result in good yields, as further described herein.
Certain of the cyclodiene pesticides of this invention may be called dehalogenated (dechlorinated) derivatives of substituted polyhalogenated (polychlorinated) norbornanes, norbornenes or norbornadienes. We prefer ho
REFERENCES:
patent: 3062709 (1962-11-01), Ordas
patent: 3110648 (1963-11-01), Feichtinger et al.
patent: 3222249 (1965-12-01), Koremura et al.
Coulston International Corporation
Robinson Allen J.
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