Use of gossypol and related terpenes for control of urban...

Drug – bio-affecting and body treating compositions – Plant material or plant extract of undetermined constitution...

Reexamination Certificate

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C424S093500, C424S773000, C424S774000, C424S776000, C424S778000, C424S779000, C424SDIG001, C514S027000, C514S451000, C514S452000, C514S453000, C514S456000, C514S457000, C514S458000, C514S464000, C514S465000, C514S468000, C514S474000, C514S475000, C514S680000, C514S681000, C514S700000, C514S715000, C514S724000, C514S729000, C514S739000, C514S762000, C514S763000, C514S766000, C043S121000, C043S132100

Reexamination Certificate

active

06773727

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to compositions and methods effective for control of social insects such as termites, fire ants, and cockroaches.
2. Description of the Prior Art
Cotton plants, especially the seed, are a rich source of gossypol and related terpenes. Cotton is a major cash crop of the Southern states of the U.S. Cotton seed (a by-product) with an annual production of 7 million tons in the U.S. and 36 million tons worldwide, has long been processed into edible oil and protein feed meals. Due to the presence of gossypol, a known antinutritional factor to nonruminant animals, the protein meals are primarily used as feed to ruminants. Processing technologies (Gardner, H. K., et al., “Advanced liquid cyclone process for edible cotton seed flour production,” [1973
]E. Oil Mill Gaz
. 78:12-17; Freeman et al., “Advanced air classification of defatted, glanded cotton seed flours to produce edible protein product,” [1979
]J. Food Sci
. 44:1522-1524) have been developed at the U.S. Department of Agriculture to reduce the concentration of gossypol in the finished meal. A cotton seed meal produced by these processes can be used as a food ingredient as long as it contains no more than 450 ppm free gossypol, a limit established by the research effort of the Southern Regional Research Center, ARS-USDA, New Orleans, La. (Code of Federal Regulations 21.172.894).
Glandless cultivars, through conventional breeding, are subject to attack by beet armyworm (
Spodoptera exigua
[Hubner]), bollworm (
Heliothis zea
[Boddie]), grape colaspis (
Maecolaspis flavida
[Say]), cutworms (undetermined species), and pill bugs (Porcellio spp.). Rodents also attacked glandless bolls and ate glandless cotton seed more aggressively than the glanded seed as (Bottger et al., “Relation of gossypol content of cotton plants to insect resistance,” [1964
] J. Econ. Entomol
. 57:283-285). Gossypol is also toxic to cotton aphids (
Aphis gossypii
Glover), lygus bugs (
Lygus hesperas
Knight), salt-marsh caterpillars (
Estigmene acrea
[Drury]), thurberia weevils (
Anthonomus grandis thurberiae
Pierce), and bollworms (Bottger et al., 1964, supra). Jenkins et al. (“The comparative preference of insects for glanded and glandless cottons,” [1966
] J. Econ. Entomol
. 59:352-356), showed that grape colaspis and leaf beetle (
Gastrophysa cyanea
Melsheimeriae) preferred feeding on glandless compared to glanded cotton cultivars, and cotton leafworm moths (
Alabama argillacea
[Hubner]) preferred to oviposit on glandless lines.
In addition to gossypol, several other toxic terpenoids (generally referred to as terpenoid aldehydes) are found in the glands in foliar tissue of cotton plants, including p-hemigossypolone, p-hemigossypolone-6-methyl ether, heliocide H
1
, heliocide H
2
, heliocide H
3
, heliocide H
4
, heliocide B
1
, heliocide B
2
, heliocide
3
, and heliocide B
4
.
The effective dosage (&mgr;moles/g diet) of toxic terpenoids required to reduce by 50% the growth of the tobacco budworm (
Heliothis virescens
[F.]) larvae fed an artificial diet have been determined for several of these compounds as follows: heliocide H
1
, 2.5; heliocide H
2
, 11.2; heliocide H
3
, 3.9; heliocide B
1
, 4.6; hemigossypolone, 10.5; and gossypol, 0.8 (Stipanovic et al., “Natural insecticides from cotton (Gossypium)”, [1977
] ACS Symposium Series, No
. 62
, Host Plant Resistance to Pests
, 197-214). Hemigossypolone-6-methyl ether and heliocides B
2
and B
3
had no effect on growth at 2.5 &mgr;moles/g diet. In this study, gossypol was the most toxic compound with heliocides H
1
and H
3
a close second and third. Conversion to the 6-methyl ether derivative consistently reduced toxicity. In contrast, field studies have shown that the levels of heliocides and hemigossypolone correlate better with resistance than the gossypol levels (Hedin, P. A. et al., “Relationship of glands, so cotton square terpenoid aldehydes and other allelochemicals to larval growth of
Heliothis virescens
[Lepidoptera: Noctuidae],” [1992
] J. Econ. Entomol
. 85:359-364; Jenkins, J. N., “Host resistance to insects in cotton,” [1995
] in Proceedings of the World Cotton Research Conference
-1, edited by G. A. Constable and N. W. Forrester, Melbourne, Australia, pp. 359-372).
In addition to the terpenoid aldehydes, the volatile mono- and sesquiterpenes also occur exclusively in the foliar glands. Damaged glandless plants can also produce terpenes, but in much smaller amounts. The volatile terpene caryophyllene oxide interacts synergistically with gossypol to retard tobacco budworm larval growth (Gunasena et al., “Effects of caryophyllene, caryophyllene oxide, and their interaction with gossypol on the growth and development of
Heliothis virescens
[F.][Lepidoptera: Noctuidae],” [1988
] J. Econ. Entomol
. 81:93-97; Williams et al., “Effects of gossypol and other cotton terpenoids on
Heliothis virescens
development,” [1987
]Rev. Latinoamer. Quim
. 18:119-131), but the related sesquiterpene caryophyllene does not act synergistically. When glands are eaten, insects consume the terpenoid aldehydes along with a diverse mixture of monoterpenoids.
Several other low molecular weight compounds and condensed tannins have been implicated as possible factors in insect resistance. Hedin et al. (“Cyanidin-3 &bgr;-Glucoside, a newly recognized basis for resistance in cotton to the tobacco budworm
Heliothis virescens
(Fab.),” [1983
]Experientia
39:799-801), have identified cyanidin-3&bgr;-glucoside in the glands. This and various other allelochemicals (i.e., condensed tannins, flavonoids, and cyclopropene fatty acids) have been evaluated for their effect on bollworms and budworms (Shaver, T. N. and Lukefahr, M. J., “Effects of flavonoids pigments and gossypol on growth and development of the bollworm, tobacco budworm, and pink bollworm,” [1969
] J. Econ. Entomol
. 62:643-646; Elliger et al., “Relative toxicity of minor cotton terpenoids compared to gossypol, ” [1978
] J. Econ. Entomol
. 71:161-164; Chan et al., “Inhibition of lepidopterous larval growth by cotton constituents,” [1978
] Entomol. Exp. Appl
. 24:94-100; Chan et al., “Condensed tannin, an antibiotic chemical from
Gossypium hirsutum
,” [1978
] J. Insect Physiol
. 24:113-118; Chan et,al., “A rapid diet preparation method for antibiotic phytochemical bioassay,” [1978
] J. Econ. Entomol
. 71:366-368; Hedin et al., “The chemical basis for resistance in cotton to
Heliothis insects
,” [1981] In
Regulation of Insect Development and Behavior
, M. Kloza, Ed., Wroclaw Univ. Press, pp. 1071-1086; Hedin et al., “Effects of cotton plant allelochemicals and nutrients on behavior and development of tobacco budworm,” [1991
] J. Chem. Ecol
. 17:11-7-1121; Jenkins et al., “Cotton allelochemicals and growth of tobacco budworm larvae,” [1983
] Crop Sci
. 23:1195-1198). These compounds also can play a role in insect resistance. Reports in the literature comparing glandless and glanded plants may refer to the gossypol content of the latter, but actually refer to all of the terpenoid aldehydes in the gland. Cotyledonary leaves are an exception, since the terpenoid aldehyde present in this tissue is almost exclusively gossypol.
Bollworms and tobacco budworms grow better on glandless than on glanded cottons. However, differences in infestations of cotton fleahoppers (
Psallus seriatus
[Reuter]) and the boll weevil (
Anthonomus grandie
Boheman) between glanded and glandless plants were small or non-existent. Lukefahr and Martin (1966), supra, found that gossypol was equally toxic to bollworm and tobacco budworm larvae. Bottger, G. T. and Patana, R. (“Growth, development, and survival of certain lepidoptera fed gossypol in the diet,” [1966
] J. Econ. Entomol.
59:1166-1168), found the beet armyworm,

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