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WO1986001724A1 - Pesticides derives de la xanthine - Google Patents

Pesticides derives de la xanthine Download PDF

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Publication number
WO1986001724A1
WO1986001724A1 PCT/US1985/001708 US8501708W WO8601724A1 WO 1986001724 A1 WO1986001724 A1 WO 1986001724A1 US 8501708 W US8501708 W US 8501708W WO 8601724 A1 WO8601724 A1 WO 8601724A1
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WO
WIPO (PCT)
Prior art keywords
xanthine
pest
substituted
dimethyl
hydrogen
Prior art date
Application number
PCT/US1985/001708
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English (en)
Inventor
James Nathanson
Original Assignee
The General Hospital Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Publication of WO1986001724A1 publication Critical patent/WO1986001724A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention is directed to a method for controlling a pest comprising bringing into contact with the pest a pest-controlling amount of a compound from the group comprising derivatives of xanthine.
  • DCDM which is the probable in vivo metabolite of CDM is about six-fold more potent than octopamine itself as a partial agonist of light organ octopamine-stimulated adenylate cyclase. Stimulation by the formamidines resulted in increased formation of the intracellular messenger, cyclic AMP (cAMP).
  • cAMP cyclic AMP
  • cyclic AMP as a "second messenger" has led to the accepted model that a hormone or neuro transmitter binds at a cell-membrane bound receptor, which activates adenylate cyclase to a form capable of converting ATP in the cytoplasm of the cell into cAMP. cAMP then relays the signal brought by the hormone or neuro transmitter from the membrane to the interior of the cell. Agonists of the hormone or neuro transmitter are, by definition, capable of eliciting the same response (see, for example, Nathanson and Greengard, Scientific American, 237: 108-119 (1977)).
  • cAMP stimulates the conversion of inactive phosphorylase b into phosphorylase a, a reaction catalysed by phosphorylase kinase.
  • This reaction is, in turn, catalysed by an enzyme, now called protein kinase, which occurs in an inactive and active form.
  • protein kinase catalysed by an enzyme, now called protein kinase, which occurs in an inactive and active form.
  • active form catalyses the phosphorylation of inactive phosphorylase kinase by ATP to yield the active phosphorylated form by a reaction in which ATP is the phosphate-group donor.
  • Protein kinase the key enzyme in linking cAMP to the phosphorylase system and to other cyclic AMPregulated processes, is an allosteric enzyme, that is, an enzyme whose reactivity with another molecule is altered by combination with a third molecule that is not a substrate. Its inactive form contains two types of subunits, a catalytic (C) subunit and a regulatory (R) subunit which inhibits the catalytic subunit.
  • C catalytic
  • R regulatory
  • cAMP is the allosteric modulator of protein kinase, binding to a specific site on the regulatory subunit and causing the inactive CR complex to dissociate, yielding R-cAMP complex, and the free C subunit, which is now catalytically active.
  • cAMP removes the inhibition of enzyme activity that is imposed by the binding of the regulatory subunit (Lehninger, Biochemistry, Second Edition, pages 812-813).
  • the enzyme responsible for the destruction of cAMP is phosphodiesterase, which catalyzes the hydrolytic reaction as follows:
  • Calva United States Patent 2,362,614, describes fluorine-containing insecticides. Disclosed are the hydrofluoric acid addition compounds of ammonia-substituted compounds giving rise to primary, secondary or tertiary amines and polyamines. Insecticidal activity is described as derived from the direct combination of the fluorine-nitrogen link. Caffeine is included in the patent disclosure among the "alkylamines with or without substituent groups.”
  • French Patent 2,138,186 to Aries discloses insecticidal compositions of urinylphosphate esters which are stabilized by purine derivatives. Included among the purine derivatives are purines substituted in the 2, 4 and 8 positions. No insecticidal activity, however, is attributed to the purine compounds, the compounds performing the function of stabilizing the active phosphorus compounds.
  • xanthine derivatives including caffeine and theophylline
  • caffeine and theophylline are found in berries, seeds, and leaves of a number of species, including tea, coffee, cocoa and cola.
  • methylxanthines are one of the most frequently used stimulants employed by the human population, their natural function in plants was not known up to the present. It is known, however, that to discourage insect feeding, many plants have evolved endogenous chemical defenses, ranging from specific toxins and substances with pheromone-like activity to less specific bitter-tasting aversive substances.
  • this invention comprises a method of pest control comprising bringing into contact with said pest a pest-controlling amount of an agent consisting essentially of a compound having the general formula (I) or (II):
  • X is oxygen or sulfur;
  • R 1 , R 2 , R 3 , R 4 and R 5 are selected from hydrogen; aliphatic and cycloaliphatic hydrocarbons having 1-8 carbon atoms; substituted aliphatic and cycloaliphatic hydrocarbons substituted with 1-3 halogen atoms, lower alkyl (C 1 -C 4 ), or hydroxy; alkoxy having 1-6 carbon atoms; aromatic; halo, hydroxy, or lower alkyl-substituted aromatic; phenoxy; substituted phenoxy; and the like, and acid addition salts of the above, where at least one of R 1 , R 2 , R 3 , or R 5 is other than hydrogen.
  • said agent is further defined by having a V max of more than 50%, where V max is expressed as the inhibition of feeding at the highest dose used, usually a 3% spray solution, and an EC 50 of less than 3% (gm/100 ml), EC 50 being the spray concentration required to cause 50% inhibition of feeding, as calculated from dose-response curves.
  • the most preferred compounds have a K i of not more than 0.1, where K i is defined as the concentration in millimoles/liter of the xanthine derivative required to produce a 50% in vitro inhibition of the phosphodiesterase activity in tobacco hornworm nerve cord, using the conditions described.
  • Figure 1A shows the effect on tobacco hornworm body weight of powdered coffee beans or caffeine incorporated into artificial media.
  • Figure 1B shows the dose-dependent antifeeding effect of caffeine.
  • Figure 1C is a graph quantitating the antifeeding effect of caffeine and other xanthine derivatives applied as a spray to tomato leaves subsequently exposed to tobacco hornworm larvae for 4 days.
  • Figure 1D is a graph showing the effect of the same xanthine derivatives on inhibiting cyclic AMP phosphodiesterase activity in homogenates of tobacco hornworm nerve cord.
  • Figure 2 is a graph showing the phosphodiesterase inhibiting activity of various xanthine derivatives in tobacco hornworm nerve cord.
  • pest-controlling or “pest-controlling activity,” used throughout the specification andclaims, are meant to include any pesticidal (killing) or pestistatic (inhibiting, maiming or generally interfering) activities of a composition against a given pest.
  • these terms not only include killing, but also include such activities as those of chemisterilants which produce sterility in insects by preventing the production of ova or sperm, by causing death of sperm or ova, or by producing severe injury to the genetic material of sperm or ova, so that tha larvae that are produced do not develop into mature progeny.
  • inhibiting the feeding is meant to include both pesticidal activity wherein the pest is killed by the compound, as well as the situation wherein the feeding activity of the larvae is substantially affected and limited.
  • pest is meant any phosphodiesterase-containing invertebrate.
  • These pests include, but are not limited to, round worms (for example, hookworms, trichina, and ascaris); flat worms (for example, liver flukes and tapeworms); jointed worms (for example, leeches); molluscs (for example, parasitic snails); and arthropods (insects, spiders, centipedes, millipedes, crustaceans (for example, barnacles)).
  • arthropods included among the arthropods are ticks, mites (both plant and animal), lepidoptera (butterflies and moths and their larvae), hemiptera (bugs), homoptera (aphids, scales), and coleoptera (beetles).
  • spiders anoplura (lice), diptera (flies and mosquitos), tricoptera, orthoptera (for example, roaches), odonta, thysanura (for example, silverfish), collembola (for example, fleas), dermaptera (earwigs), isoptera (termites), ephemerids (mayflies), plecoptera, malophaga (biting lice), thysanoptera, and siphonaptera (dictyoptera, psocoptera, and certain hymenoptera (for example, those whose larvae feed on leaves)).
  • anoplura lice
  • diptera flies and mosquitos
  • tricoptera for example, roaches
  • odonta for example, silverfish
  • collembola for example, fleas
  • dermaptera earwigs
  • isoptera termites
  • ephemerids mayflies
  • plecoptera malophaga
  • xanthine derivative or “methyl xanthine derivatives” are meant compounds having the general formula (I) or (II):
  • X is oxygen or sulfur
  • R 1 , R 2 , R 3 , R 4 and R 5 are selected from hydrogen; aliphatic and cycloaliphatic hydrocarbons having 1-8 carbon atoms; aliphatic and cycloaliphatic hydrocarbons substituted with 1-3 halogen atoms, lower alkyl (C 1 -C 4 ), or hydroxy; alkoxy having 1-6 carbon atoms; aromatic; halo, hydroxy, or lower alkyl-substituted aromatic; phenoxy; substituted phenoxy; and the like, and further wherein at least one of R 1 , R 2 , R 3 or R 5 is other than hydrogen.
  • Suitable aliphatic hydrocarbon compounds include alkyl, alkenyl, alkynyl and the like.
  • alkyl hydrocarbons include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, tert-pentyl, hexyl, heptyl, octyl, and the like.
  • Suitable alkenyl hydrocarbons are those having 2-8 carbon atoms and may include vinyl, allyl, isopropenyl, 1-propenyl, 2-butenyl, 3-pentenyl, 2-, 3-, or 4-hexenyl, and the like.
  • Suitable alkynyl hydrocarbons are those having 2-8 carbon atoms and may include ethynyl, 2-propynyl, 2-butynyl, 3-pentynyl, 3-hexynyl, 2-, 3-, or 4-heptynyl, and the like.
  • Suitable cylcoaliphatic groups include those having 3-8 carbon atoms, for example, cyclopentyl, cycloheptanyl, cyclohexanyl, cyclopentenyl, cyclohexynyl, and the like, as well as lower alkyl, halo or hydroxy substituted alkoxy groups.
  • Suitable alkoxy groups include methoxy, ethoxy, butoxy, pentoxy, and the like.
  • Suitable aromatic groups include phenyl or naphthyl.
  • substituted aromatic groups are phenyl substituted in the ortho, meta, and/or para positions with lower alkyl groups having 1-4 carbon atoms, halogens, and hydroxy.
  • the fluoride salts are generally excluded; where the compounds are intended as pestistats, caffeine is excluded.
  • R 2 increases activity substantially, with 3-isobutyl xanthine derivatives demonstrating superior effectiveness among the preferred compounds.
  • substitution of small to medium (methyl, ethyl, propyl, i-propyl) groups in the 1-position ( R 1 ) increases activity.
  • Small to medium group substitution on the 7-position ( R 3 ) also will enhance activity, as will certain small to medium group in the 8-pos ⁇ tion (R 4 ).
  • chloro or bulky substituent in the 8-position decreases activity as do certain substitutions in the 9-position ( R 5 ).
  • the preferred compounds of the present invention are further defined as those compounds having a V max of more than 50% inhibition of feeding and an EC 50 of less than a 3% (gm/100 ml) concentration of spray.
  • V max is expressed as the percent inhibition of feeding at the highest dose used (usually a 3% spray solution).
  • EC 50 is the spray concentration (as calculated from dose-response curves) required to cause 50% inhibition of feeding. Inhibition of feeding is determined at a time when untreated leaves show 20% of leaf area remaining. Calculation is then made by determining the percent leaf area remaining on leaves sprayed with drugs minus 20 divided by 80 (the maximal inhibition of feeding possible). The inhibition of feeding determination will be described in detail below. Basically, leaves are eaten by first-instar Manduca sexta which are placed at 6 per leaf.
  • methylxanthines are known to inhibit phosphodiesterase (PDE), enzymes which hydrolyze cAMP.
  • Rail, T. W. Pharmacological Bases of Therapeutics, A. G. Gillman, L. Goodman, A. Gillman, Editors (MacMillan, New York, 1980), p. 592; Sutherland, E. W., et al., Journal of Biological Chemistry, 232: 1077 (1958); and Butcher, R. W., et al., Journal of Biological Chemistry, 237: 1244 (1962).
  • the similarity of the graphs in Figures 1C and ID demonstrates a strong correlation between PDE inhibition and pesticidal and pestistatic activity. This correlation is further evaluated in Examples 15 through 42 below.
  • the most preferred compounds according to the present invention are those xanthine derivatives according to structural formulas (I) and (II) which also demonstrate a K i of 0.1 mM or less, wherein K- is defined as the concentration of xanthine derivative necessary to produce a 50% inhibition of enzyme activity for hornworm nerve cord PDE. Inhibition of phosphodiesterase activity for hornworm nerve cord for the purposes of determining K i within the meaning of this invention is determined in accordance with the methodology set out in Examples 8-11.
  • the pest-controlling agents of the present invention may be formulated as dusts, water dispersions, emulsions and solutions. They may comprise accessory agents such as dust carriers, solvents, emulsifiers, wetting and dispersing agents, stickers, deodorants, and masking agents (see, for example. Encyclopedia of Chemical Technology, Volume 13, pages 416 et seq.).
  • Dusts generally will contain low concentrations, 0.1-20%, of the compounds, although ground preparations may be used and diluted.
  • Carriers commonly include organic flowers, sulfur, silicon oxides, lime, gypsum, talc, pyrophyllite, bentonite, kaolins, attapulgite, and volcanic ash. Selection of the carrier may be made on the basis of compatibility with the desired pest control composition (including pH, moisture content, and stability), particle size, abrasiveness, absorbability, density, wettability and cost.
  • the agent of the invention, alone or in combination, and eluent is made by a variety of simple operations such as milling, solvent impregnations, fusing and grinding. Particle sizes usually range from 0.5-4.0 microns in diameter.
  • Wettable powders may be prepared by blending the agents of the invention in high concentrations, usually from 15-95%, with a dust carrier such as bentonite which wets and suspends properly in water. Twenty-two percent of a surface-active agent is usually added to improve the wetting and suspendability of the powder.
  • the pest-controlling agents may also be used in granules, which are pelleted mixtures of the agents, usually at 2.5-10%, and a dust carrier, for example, adsorptive clay, bentonite or diatomaceous earth, and commonly within particle sizes of 250-590 microns.
  • Granules may be prepared by impregnations of the carrier with a solution or slurry of the agents and may be used principally for mosquito larvae treatment or soil applications.
  • the agent may also be applied in the form of an emulsion, which comprises a solution of the agents in water-immiscible organic solvents, commonly at 15-50%, with a few percent of surface active agent to promote emulsification, wetting, and spreading.
  • emulsion comprises a solution of the agents in water-immiscible organic solvents, commonly at 15-50%, with a few percent of surface active agent to promote emulsification, wetting, and spreading.
  • the choice of solvent is predicated upon solubility, safety to plants and animals, volatility, flammability, compatibility, odor and cost.
  • the most commonly used solvents are kerosene, xylenes, and related petroleum fractions, methylisobutyIketone, and amyl acetate. Water emulsion sprays from such emulsive concentrates may be used for plant protection and for household insect control.
  • the agents may also be mixed with baits, usually comprising 1-5% of agents with a carrier especially attractive to insects.
  • Carriers include sugar for houseflies, protein hydrolysate for fruit flies, bran for grasshoppers, and honey, chocolate, or peanut butter for ants.
  • the agents may be included in slow release formulations which incorporate non-persistent compounds, insect growth regulators and sex pheromones in a variety of granular microencapsulated and hollow fiber preparations.
  • the pest-controlling agents of the present invention may be applied depending on the properties of the particular pest-controlling compound, the habits of the pest to be controlled, and the site of the application to be made. It may be applied by spraying, dusting or fumigation.
  • Doses of the weight of the ingredients may typically vary between 0.001 and 100 pounds/acre, preferably between 0.001-5 pounds/acre.
  • Sprays are the most common means of application and generally will involve the use of water as the principal carrier, although volatile oils may also be used.
  • the pest-controlling agents of the invention may be used in dilute sprays (for example, 0.001-10%) or in concentrate sprays in which the composition is contained at 10-98%, and the amount of carrier to be applied is quite reduced.
  • the use of concentrate and ultra-low volume sprays will allow the use of atomizing nozzles producing droplets of 30-80 microns in diameter. Spraying may be carried out by airplane or helicopter.
  • Aerosols may also be used to apply the pest-controlling agents. These are particularly preferred as space sprays for application to enclosures, particularly against flying insects. Aerosols are applied by atomizing amounts of liquified gas dispersion or bomb, but can be generated on a larger scale by rotary atomizers or twin-fluid atomizers.
  • a simple means of pest-controlling agent dispersal is by dusting.
  • the pest-controlling agent is applied by introducing a finely divided carrier with particles typically of 0.5-3 microns in diameter into a moving air stream.
  • xanthine derivatives were tested on natural feeding substrates, such as tomato leaves, the xanthine derivatives bein ⁇ those compounds wherein at least one of R 1 , R 2 , R 3 , and R 5 are other than hydrogen.
  • Figure 1B shows a typical result for caffeine.
  • Fi ⁇ ure 1C (which guantitates the amount of leaf remaining) summarizes the dose-response curves for caffeine (Example 4), theophylline (Example 5), and the svnthetic compound.
  • IBMX 1-methyl-3-i sobutylxa nth i ne (IBMX) (Example 6).
  • IBMX 1-methyl-3-i sobutylxa nth i ne
  • Nerve cord was dissected from 40-60 mm long M. sexta larvae, cleaned, and homogenized (2 mg/ml) in 6 Mm Tris-maleate, pH 7.4. PDE activity was measured (4 min. incubation at 30°C) in an assay system (0.1 ml) containing 80 mM Tris-maleate, pH 7.4; 6 mM Mg-SO 4 ; 10 -7 M 3 H-cyclic AMP; and tissue homogenate (0.02 ml).
  • Nerve cord was evaluated in the presence and the absence of the xanthine derivative.
  • the rate of formation of 3 H-5' AMP was measured using the technique described in Filburn,
  • Larvae feeding on leaves treated with a 1% spray were found to contain an internal theophylline concentration of 4.1 ⁇ 1.1 mM (mean ⁇ deviation for two groups of six pooled animals). This concentration was sufficient to cause more than an 80% inhibition of hornworm nerve cord PDE activity in vitro. This observation tends to rule out the hypothesis wherein adenosine receptors are involved as a mechanism for the antifeeding effects of the xanthine derivatives, since, in vertebrates, xanthine derivatives such as theophylline are competitive adenosine receptor antagonists, but exert such antagonism at much lower concentrations, typically 1-25 micromoles. See Bruns, R., et al., Proceedings of the National Academy of Sciences, USA, 77: 5547 (1980); Williams, M., et al., Proceedings of the National Academy of Sciences, USA, 77: 6892 (1980).
  • Xanthine derivatives have been reported to have calcium mobilizing effects (Links, J. R., et al., Circulation Research, 30: 367 (1972)). Xanthine derivatives are known to mobilize calcium from sarcoplasmic reticulum, an effect which is blocked by diltiazem or procaine. IBMX was evaluated with regard to antifeeding effects in the presence of both diltiazem and procaine, neither reversing the observed antifeeding effects.
  • Xanthine derivatives have also been reported to affect calcium movement across the plasma membrane (Links, J. R., et al., supra; Saeki, K., et al., Life Sciences, 32: 2973 (1983)).
  • the pestistatic and pesticidal effects of IBMX were evaluated in the presence of D600, verapamil, and nimodipine, compounds which are known to block plasma membrane calcium channels.
  • the pestistatic and pesticidal effects of IBMX appeared unaffected by these compounds.
  • caffeine has been reported to be 10-fold weaker than theophylline as an adenosine antagonist (Bruns, R., et al., supra), as demonstrated by the above Examples, caffeine was somewhat more potent than theophylline in preventing leaf eating and about equally potent as a PDE inhibitor. See Figures 1C and 1D. Also, whereas IBMX and theophylline are roughly equally potent in blocking adenosine receptors (Bruns, R., et al., supra) IBMX was about 10-fold more potent both in disruption of feeding and in PDE inhibition. See Figure 1D.
  • the very potent adenosine antagonist, 8-phenyltheophylline (K ⁇ for adenosine receptor (0.12-1.0 micromoles) (Daly, J. W., Journal of Medicinal Chemistry, 25: 197 (1982); Bruns, R., et al., supra ) exerted little antifeeding effect and was a very weak PDE inhibitor (see Figures 1C and 1D).
  • papavarine is an inhibitor of adenosine uptake, and it potentiates, rather than blocks physiological effects on adenosine receptors (Huang, M., et al., Life Sciences, 14: 489 (1974)). Taken together, these data are more consistent with a mechanism of action related to PDE inhibition than to adenosine blockade.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Utilisation des dérivés de la xanthine ayant la formule générale (I) ou (II) en tant que pesticides ou agents pestistatiques; sont également décrites des compositions pesticides et pestistatiques les contenant.
PCT/US1985/001708 1984-09-07 1985-09-06 Pesticides derives de la xanthine WO1986001724A1 (fr)

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US64808684A 1984-09-07 1984-09-07
US648,086 1984-09-07

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5336769A (en) * 1992-02-17 1994-08-09 Kyowa Hakko Kogyo Co., Ltd. Xanthine derivatives
US5447933A (en) * 1991-11-08 1995-09-05 Kyowa Hakko Kogyo Co., Ltd. Xanthine derivatives
WO1996036638A1 (fr) * 1995-05-19 1996-11-21 Chiroscience Limited Xanthines et leur utilisation therapeutique
US6090816A (en) * 1994-12-13 2000-07-18 Euro-Celtique S.A. Aryl thioxanthines
US6239166B1 (en) * 1997-04-24 2001-05-29 Robert H. Black Compositions for killing dust mites and methods of using same

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US1653710A (en) * 1925-10-27 1927-12-27 Kitchin John Colby Antirodent preparation
US2362614A (en) * 1940-03-11 1944-11-14 Jose B Calva Insecticides
US3663692A (en) * 1969-12-29 1972-05-16 Morley R Kare Methods of bird control

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US1653710A (en) * 1925-10-27 1927-12-27 Kitchin John Colby Antirodent preparation
US2362614A (en) * 1940-03-11 1944-11-14 Jose B Calva Insecticides
US3663692A (en) * 1969-12-29 1972-05-16 Morley R Kare Methods of bird control

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CLARK, Ent. Exp. and Appl., Vol. 29, pp. 189-197 (1981) *
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5447933A (en) * 1991-11-08 1995-09-05 Kyowa Hakko Kogyo Co., Ltd. Xanthine derivatives
US5336769A (en) * 1992-02-17 1994-08-09 Kyowa Hakko Kogyo Co., Ltd. Xanthine derivatives
US6090816A (en) * 1994-12-13 2000-07-18 Euro-Celtique S.A. Aryl thioxanthines
WO1996036638A1 (fr) * 1995-05-19 1996-11-21 Chiroscience Limited Xanthines et leur utilisation therapeutique
AU692104B2 (en) * 1995-05-19 1998-05-28 Darwin Discovery Limited Xanthines and their therapeutic use
US5821366A (en) * 1995-05-19 1998-10-13 Chiroscience Limited Xanthines and their therapeutic use
US6124288A (en) * 1995-05-19 2000-09-26 Darwin Discovery, Ltd. Xanthines and their therapeutic use
US6239166B1 (en) * 1997-04-24 2001-05-29 Robert H. Black Compositions for killing dust mites and methods of using same

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