Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-08-29
2002-04-09
Chang, Ceila (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S317000, C546S184000, C546S248000
Reexamination Certificate
active
06369078
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to novel analogues of solenopsin and their use as inhibitors of the biosynthesis of the venom of fire ants, repellents and/or insecticides.
BACKGROUND OF THE INVENTION
The solenopsins are piperidine alkaloids derived from the venom of the red fire ant
Solenopsis invicta.
The venom of this insect consists of 95% alkaloids and the remainder contains solubilized proteins, amino acids and enzymes including hyaluronidase and phospholipase. Among the piperidine alkaloids, the two major components are Solenopsin A, a trans-2-methyl 6-n-undecylpiperidine and Solenopsin B, a 2,6-trans-dialkyl-piperidine. Additionally, Solenopsin A, the primary component and Solenopsin B can be produced synthetically.
The red imported fire ants
Solenopsis invicta
were accidentally introduced into the southeastern United States around 1929, and they currently infest more than 290 million acres of land in eleven states and Puerto Rico. They are considered to be pests because of their painful stings, to which some people are allergic, and because of their deleterious effects on biodiversity and agriculture.
Fire ants are native species of South America, found naturally in southern Brazil, northern Argentina, and throughout Uruguay. Buren, et al.,
Zoogeography of the importedfire ants. N.Y. Entomol. Soc.
1974, 82, 113-124. Their natural habitat is one of constant environmental upheaval resulting from the flooding of the Paraguay river. As a result, fire ants have evolved mechanisms over time to quickly recover from environmental turbulence and repopulate the disturbed environment of the flood plain. Mann, C. C.
Science,
1994, 18, 18-19. Upon introduction into North America, this adaptive ability of fire ants was instrumental in the spread of the species throughout the southeast. Jemal, A.; Jones, M. H.
Preventive Veterinary Medicine,
1993, 17, 19-32.
S. invicta
prefer open habitats such as pastures and lawns, but they have been shown to naturally occupy woodland areas also. Jemal, A.; Jones, M. H.
Preventive Veterinary Medicine,
1993, 17, 19-32. Tschinkel and coworkers coined the description “weed species” for red imported fire ants (RIFA), which refers to the ants ability to opportunistically invade disturbed environments. Tschinkel, W. R.
Fire ants and Leaf
-
cutting ants: Biology and Management.
Eds. Clifford Logren and Rober Vander Meer. 1986, Westview Press, 72-87. Not surprisingly, human progress has provided an abundance of disturbed environments as a result of general urbanization. There is considerable evidence that RIFA are susceptible to very dry and hot environmental conditions. Moreover, since
S. invicta
cannot survive temperatures below freezing, climate conditions have limited their northward expansion into North America.
A typical RIFA colony has a shallow but extensive network of tunnels. Although the tunnels range in depth from only 2-12 meters, they can radiate from the mound to a distance of over 25 feet. The mounds have been shown to maintain temperature and humidity, even in water saturated soil conditions. Shower, A. T.; Reagan, T. E.
J. Entomol. Sci. Suppl.
1987, 1, 52-64.
Fire ants typically sting their prey to defend their mounds from larger animals. Any disturbance sends hundreds of workers out to assault anything that moves. The fire ant grabs onto its victim with its jaws, and then inserts its stinger. Once the ant attaches in this manner, it can sting several times without letting go. Moreover, stinging releases chemical messengers which provokes other ants into the same process.
The venom fire ants secrete contains mostly alkaloids and a small amount of protein. Once stung, the victim experiences a sharp pain for a few minutes. The sting then starts to itch, and a welt appears. The alkaloid kills skin cells, and the proteins can elicit allergic responses such as nausea, vomiting, dizziness, and asthma which require medical attention. There have been cases of death where adults have extreme allergic reactions, and where toddlers have fallen on the fire ant mounds. Deshazo, R. D.; Butcher, B. T., Banks, W. A.
N. Engl. J. Med.
1990, 323, 462-466.
S. invicta
have been known to destroy other insect species, crops, and even farm machinery. MacKay, W. P.; Vinson, S. B.
Applied Myrmecology: A World Perspective.
Eds. Robert Vander Meer, Klaus Jaffe, Aragua Cedeno. 1990, Westview Press, Boulder, 614-619. Although they eat a wide variety of foods, fire ants primarily eat other invertebrates such as spiders, scorpions, mites, centipedes, and earthworms. Tschinkel, W. R.
Fire ants and Leaf
-
cutting ants: Biology and Management.
Eds. Clifford Logren and Rober Vander Meer. 1986, Westview Press, 72-87. Their presence can even reduce or eliminate ground-nesting mammals and birds. Jemal, A.; Jones, M. H.
Preventive Veterinary Medicine,
1993, 17, 19-32. Fire ants have had significant deleterious effects on crop yields of soybeans, corn, potatoes, okra, and berries by feeding on germinating seeds, buds, and developing fruit. Smith, B. J.; Lockley, T. C.
J. Entomol. Sci.
1993, 28, 236-239. To make matters worse, fire ants do not harm mealy bugs, which damage many types of crops. These problems are unfortunately worse in drought weather when the ants supplement their water intake with plant matter. Remarkably, fire ants have been known to destroy farm equipment because of their large numbers. For example, by crowding between parts, fire ants have removed insulation from wires and blocked the action of mechanical devices. MacKay, W. P.; Vinson, S. B.
Applied Myrmecology: A World Perspective.
Eds. Robert Vander Meer, Klaus Jaffe, Aragua Cedeno. 1990, Westview Press, Boulder, 614-619. Moreover, fire ants have been blamed for infrastructure damage; when they have built their nests under roads, the roads have been known to collapse. One of the biggest industrial problem is with electric power companies—approaching $1 million or more a year in Georgia alone.
Attempts of Fire Ant Suppression by Chemical Methods
Since the early 1950's, insecticides have been the primary method of choice to control fire ants. There are three broad classes of insecticides for fire ants: (1) the contact insecticides, which enter the ant through the skin; (2) the stomach insecticides, which are ingested; and (3) the fumigants, which are inhaled.
The contact insecticides typically destroy the imported fire ants within one week by way of their residues. Although they work quickly, their application is too difficult for use in large areas with numerous mounds. Consequently, they are only suited for small areas such as backyards. Banks, W. A.
Applied Myrmecology: A World Perspective.
Eds. Robert Vander Meer, Klaus Jaffe, Aragua Cedeno. 1990, Westview Press: Boulder, Colo., 596-603. As a whole, these insecticides are 80% effective, but if they do not kill all the ants after one application, the survivors will build new mounds, and reapplication will be necessary. There are two main groups of contact insecticides: (1) the chlorinated hydrocarbons and (2) the organophosphates.
The first methods of chemical control of
S. invicta
employed the use of chlorinated hydrocarbons, such as heptachlor and dieldrin. Lofgren, C. S.
Fire ants and Leaf
-
cutting ants: Biology and Management.
Eds. Clifford Logren and Rober Vander Meer. 1986, Westview Press: Boulder, Colo. 36-47. These synthetic pesticides were advantageous because they were inexpensive and very effective against a variety of insects. Furthermore, they were not easily broken down by enzymes, microorganisms, heat, or light, so they would work long after application. However, like DDT, a related chlorinated hydrocarbon, these pesticides were poisonous to a variety of diverse wildlife, and they accumulated in fat tissues so that they were distributed throughout the food chain. Consequently, these insecticides' use was subsequently halted.
The second class of contact pesticides used in the control of fire ants are the organophosphates, which are inhibitors of the enzyme acetylcholine esterase
Bowen J. Phillip
Furness M. Scott
Whitmire David
Chang Ceila
Coleman H.
Sapone W. J.
Sudol R. N.
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