Reducing the viability of un-emerged pests

Abstract

The present disclosure relates to methods for controlling pests. More particularly, the present disclosure relates to methods for reducing the viability of un-emerged pests by exposing un-emerged pests, e.g. eggs, to an effective amount of a compound of formula (I) as defined herein. The present disclosure also relates to methods for control of pests by exposing un-emerged pests to an effective amount of a compound of formula (I) as defined herein. Also described are pesticidal compositions.

Description

REDUCING THE VIABILITY OF UN-EMERGED PESTS RELATED APPLICATION

[0001] This application claims the benefit of Australian provisional patent application number 2023902520, filed 9 August 2023, the entire contents of which is incorporated herein by reference. FIELD OF THE DISCLOSURE

[0002] The present disclosure relates to methods for controlling pests. More particularly, the present disclosure relates to methods for reducing the viability of un- emerged pests by exposing un-emerged pests, e.g. eggs, to an effective amount of a compound of formula (I) as defined herein. The present disclosure also relates to methods for control of pests by exposing un-emerged pests to an effective amount of a compound of formula (I) as defined herein. Also described are pesticidal compositions. BACKGROUND

[0003] Effective pest control is essential across many industries, not least of all in agriculture in the production of food and livestock. For instance, ineffective insect control and insect infestation can result in the complete destruction of a crop, decimation of an animal population through insect feeding and the spread of disease and infection, and contamination of food production lines with the associated health concerns for animal and human consumers. Domestic and industrial insect control is similarly essential to mitigate the spread of insect-borne infection and diseases and for good hygiene practices.

[0004] The majority of pest control strategies are directed to the control of emerged pests. For instance, insects often reproduce through a lifecycle including emerged larvae, nymph and adult forms which the majority of insect control strategies target. There are good reasons for this, including that these forms, especially the adult form, are regarded as the most damaging and most dangerous, and most in need of controlling. These forms are also often regarded as the easiest to control because they are generally the longest- lived, present the most obvious infestations, are the largest, the most mobile (e.g. are most susceptible to physical and mechanical control methods), and the most susceptible to (or in many cases the only form that is susceptible to) chemical control methods.

[0005] There are comparatively few pest control methods that target un-emerged pests e.g. eggs. There are similarly good reasons for this, being generally the converse of the above; un-emerged pests are often less damaging and less dangerous, but shortest lived, smallest, immobile, less obvious, located in protected locations, and the most difficult to control, and often less susceptible to chemical control methods.

[0006] Susceptibility to chemical control methods is a key point of difference between un-emerged and emerged pests. Un-emerged pests contain a sheath (e.g. shell) that essentially provides a protective barrier for the contained un-emerged pest form, which can be impenetrable to many chemical control agents. Even when a chemical control agent can penetrate this barrier, in many instances the contained insect form – in the case of eggs being an embryo – does not have the same biological target site that makes a chemical agent effective against nymphs or adults, and / or not in the same abundance. Some un-emerged forms including embryos may also produce unique enzymes which break down chemical control agents. In a specific example, bed bug (Cimex lectularius) eggs have been shown to be less susceptible to pyrethroid insecticides than nymphs or adults through enhanced enzymatic breakdown, eggshell penetration resistance and a lower biological target site sensitively. In another example, eggs of the lesser grain borer, Rhyzopertha dominica, have been shown to be less susceptible to phosphine than nymphs and adults through similar mechanisms.

[0007] For the control of un-emerged pests, this tends to lead to the requirement for targeted chemical control agent application (e.g. fixed-point application rather than broadcasting) and higher application rates, which can make un-emerged pest control economically and environmentally unfeasible even for chemical agents that can penetrate protective sheaths. Ultimately, this leads to a focus on the control of the other lifecycle stages and pest forms, and particularly on nymphs and adults. There remains comparatively few pest control agents that are targeted at un-emerged pests.

[0008] It would be desirable to provide improved pest control methods to address at least some of the problems above and which may provide further pest management options for users.SUMMARY OF THE DISCLOSURE

[0009] In one aspect, the present disclosure provides a method for reducing the viability of an un-emerged pest, comprising exposing the un-emerged pest to an effective amount of a compound of formula (I):(I), wherein: X and Y are each independently selected from oxygen, sulfur and NR4, or one of C=X and C=Y is CH2; A is (C=O)R1, (C=S)R1, OR2, SR2, (CR3NR4R5), C(R3)2OR2, NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2or SO4R2; B is H, C1-C10alkyl, C2-C10alkenyl, aryl or heteroaryl; C, D, E and F are independently selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2 and SO4R2; R1 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C1-C10haloalkyl, C1-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10 haloalkoxy, C1-C10 hydroxyalkyl, C1-C10 thioalkyl, C1-C10 nitroalkyl, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7 and SO4R7; R2is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2 and NR4OR7; R3 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10 haloalkoxy, OR7, SR7, (CR8NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7 and SO4R7; R4and R5are independently selected from H, C1-C10alkyl, C2-C10arylalkyl, C3- C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10 trihaloalkyl, OR7 and SR7;R6 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR7, SR7, (CR8NR9R10), NR9R10, and NR9OR7; R7 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; R8 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR11, SR11and NR9OR10; R9and R10are independently selected from H, C1-C10alkyl, C2-C10arylalkyl, C3- C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR12 and SR12; R11is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; and R12is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl and C2-C10trihaloalkyl.

[0010] In another aspect, there is provided a method for controlling pests, comprising exposing an un-emerged pest to an effective amount of a compound of formula (I) as defined herein.

[0011] In another aspect there is provided the use of a compound of formula (I) as defined herein, for reducing the viability of an un-emerged pest or for controlling pests, wherein un-emerged pest(s) are exposed to an effective amount of the compound of formula (I).

[0012] In another aspect, there is provided a kit when used for reducing the viability of an un-emerged pest or for controlling pests, comprising a compound of formula (I) as defined herein.

[0013] In preferred embodiments of each aspect, the un-emerged pest is a pest egg.

[0014] In preferred embodiments of each aspect, the compound of formula (I) is a β- diketone compound of formula (I) as defined herein, preferably tasmanone.DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 is a photograph taken of a test of ovicidal activity against eggs of Cimex lectularius (Example 1), with the appearance of dead eggs, hatched eggs and dead nymphs indicated.

[0016] Figure 2 graphs the mean percentage ovicidal and nymph mortality of bed bugs, Cimex lectularius, at 14 days post treatment application (means ± standard errors, n=5) in a range-finder test of ovicidal activity against eggs of Cimex lectularius (Example 1).

[0017] Figure 3 graphs the mean percentage egg and nymph mortality of Two-spotted spider mites, Tetranychus urticae, at 5-day post treatment application (means ± standard errors, n=5) in a range-finder test of ovicidal activity against eggs of Tatranychus urticae (Example 3).

[0018] Figure 4 graphs the mean percentage ovicidal and nymph mortality of Two- spotted spider mites, Tetranychus urticae, at 5-day post treatment application (means ± standard errors, n=5) in a definitive range-finder test of ovicidal activity against eggs of Tetranychus urticae (Example 3). DETAILED DESCRIPTION

[0019] Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art of this disclosure. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing embodiments of the present disclosure, preferred methods and materials are described. For the purposes of the present disclosure, a number of terms are defined throughout.

[0020] As used herein, the terms “a” and “an” are used herein to refer to one or to more than one (i.e. to at least one) of the grammatical object of the article. By way of example, “an element” means one element or more than one element.

[0021] As used herein, the term “and / or”, e.g., “A and / or B” shall be understood to mean either “A and B” or “A or B” and shall be taken to provide explicit support for both meanings or for either meaning.

[0022] As used herein, the term “about”, unless stated to the contrary, refers to ±10% of the designated value.

[0023] Except where the context requires otherwise due to express language or necessary implication, as used herein the term “comprise” or variations such as “comprises” or “comprising” is used in an inclusive sense, i.e. to specify the presence of the stated features but not to preclude the presence or addition of further features in various embodiments disclosed.

[0024] It is to be understood that, if any prior art publication is referred to herein, such reference does not constitute an admission that the publication forms a part of the common general knowledge in any country. Compounds of Formula (I)

[0025] A compound of formula (I) is defined as follows:(I), wherein: X and Y are each independently selected from oxygen, sulfur and NR4, or one of C=X and C=Y is CH2; A is (C=O)R1, (C=S)R1, OR2, SR2, (CR3NR4R5), C(R3)2OR2, NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2 or SO4R2; B is H, C1-C10alkyl, C2-C10alkenyl, aryl or heteroaryl; C, D, E and F are independently selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2and SO4R2; R1 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C1-C10haloalkyl, C1-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, C1-C10hydroxyalkyl, C1-C10thioalkyl, C1-C10nitroalkyl, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7 and SO4R7; R2 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2 and NR4OR7;R3 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR7, SR7, (CR8NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7and SO4R7; R4 and R5 are independently selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3- C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10 trihaloalkyl, OR7 and SR7; R6 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR7, SR7, (CR8NR9R10), NR9R10, and NR9OR7; R7 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; R8is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR11, SR11and NR9OR10; R9and R10are independently selected from H, C1-C10alkyl, C2-C10arylalkyl, C3- C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR12 and SR12; R11is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; and R12is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl and C2-C10trihaloalkyl.

[0026] As used herein, “Cato Cb” or “Ca-b” in which “a”“b” are integers refer to the number of carbon atoms in the specified group. That is, the group can contain from “a” to “b”, inclusive, carbon atoms. Thus, for example, a “C1 to C4 alkyl” (which may be denoted “C1-C4 alkyl”) group includes alkyl groups having from 1 to 4 carbons, consisting of 1 carbon atom, 2 carbon atoms, 3 carbon atoms and 4 carbon atoms, e.g. CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2-, CH3CH2CH(CH3)- and (CH3)3C-.

[0027] As used herein, the term “alkyl” refers to straight chain or branched saturated hydrocarbon group. An alkyl group may have a specified number of carbon atoms, for example, C1-C6alkyl includes alkyl groups having 1, 2, 3, 4, 5 or 6 carbon atoms in a linear or branched arrangement. Examples of suitable alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, 2- methylbutyl, 3-methylbutyl, 4-methylbutyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 5-methylpentyl, 2-ethylbutyl, 3-ethylbutyl, heptyl, octyl, nonyl and decyl.

[0028] As used herein, the term “cycloalkyl” refers to a saturated cyclic hydrocarbon. A cycloalkyl group may have a specified number of carbon atoms, for example, C3-C6cycloalkyl includes cycloalkyl groups having 3, 4, 5 or 6 carbon atoms. Examples of suitable cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

[0029] As used herein, the term “alkenyl” refers to a straight-chain or branched hydrocarbon group having one or more double bonds between carbon atoms. An alkenyl group may have a specified number of carbon atoms, for example, C2-C6alkenyl includes alkenyl groups having 2, 3, 4, 5 or 6 carbon atoms in a linear or branched arrangement. Examples of suitable alkenyl groups include, but are not limited to, ethenyl, propenyl, isopropenyl, butenyl, butadienyl, pentenyl, pentadienyl, hexenyl, hexadienyl, heptenyl, octenyl, nonenyl and decenyl.

[0030] As used herein, the term “aryl” refers to a stable, monocyclic, bicyclic or tricyclic carbon ring system of up to 7 atoms in each ring, wherein at least one ring is aromatic. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl, phenanthrenyl, biphenyl and binaphthyl.

[0031] As used herein, the term “heteroaryl” refers to a stable monocyclic, bicyclic or tricyclic ring of up to 7 atoms in each ring, wherein at least one ring is aromatic, and at least one ring contains from 1 to 4 heteroatoms selected from the group consisting of O, N and S. Examples of suitable heteroaryl groups include, but are not limited to, acridinyl, carbazolyl, cinnolinyl, quinoxalinyl, quinazolinyl, pyrazolyl, indolyl, isoindolyl, 1H,3H-1-oxoisoindolyl, benzotriazolyl, furanyl, thienyl, thiophenyl, benzothienyl, benzofuranyl, benzodioxane, benzodioxin, quinolinyl, isoquinolinyl, oxazolyl, isoxazolyl, imidazolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, tetrahydroquinolinyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl and tetrazolyl. Particular heteroaryl groups have 5- or 6-membered rings, such as pyrazolyl, furanyl, thienyl, oxazolyl, indolyl, isoindolyl, 1H,3H-1-oxoisoindolyl, isoxazolyl, imidazolyl, pyrazinyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl and 1,2,4-oxadiazolyl and 1,2,4-thiadiazolyl.

[0032] As used herein, the term “haloalkyl” refers to an alkyl group in which one or more hydrogen atoms is substituted with a halo atom. A haloalkyl group may have a specified number of halo substitutions, for example, dihaloalkyl (two) and trihaloalkyl (three). Examples of suitable haloalkyl groups include, but are not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1,1- difluoroethyl, 2,2-fluoroethyl, 1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, 4-fluorobutyl, 4,4-difluorobutyl, 4,4,4- trifluorobutyl, 5-fluoropentyl, 5,5-difluoropentyl, 5,5,5-trifluoropentyl, 6-fluorohexyl, 6,6-difluorohexyl or 6,6,6-trifluorohexyl, chloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 2-chloroethyl, 1,1-dichloroethyl, 2,2-chloroethyl, 1,1,2- trichloroethyl, 2,2,2-trichloroethyl, 3-chloropropyl, 3,3-dichloropropyl, 3,3,3- trichloropropyl, 4-chlorobutyl, 4,4-dichlorobutyl, 4,4,4-trichlorobutyl, 5-chloropentyl, 5,5-dichloropentyl, 5,5,5-trichloropentyl, 6-chlorohexyl, 6,6-dichlorohexyl or 6,6,6- trichlorohexyl, bromomethyl, dibromomethyl, tribromomethyl, 1-bromoethyl, 2- bromoethyl, 1,1-dibromoethyl, 2,2-dibromoethyl, 1,1,2-tribromoethyl, 2,2,2- tribromoethyl, 3-bromopropyl, 3,3-dibromopropyl, 3,3,3-tribromopropyl, 4-bromobutyl, 4,4-dibromobutyl, 4,4,4-tribromobutyl, 5-bromopentyl, 5,5-dibromopentyl, 5,5,5- tribromopentyl, 6-bromohexyl, 6,6-dibromohexyl or 6,6,6-tribromohexyl and the like.

[0033] The term “halo” refers to fluorine, chlorine, bromine and / or iodine.

[0034] As used herein, the term “hydroxyalkyl”, “thioalkyl” and “nitroalkyl” each refer to an alkyl group in which one or more hydrogen atoms is substituted with a hydroxyl group, a thiol group or a nitro group, respectively.

[0035] As used herein, the term “alkoxy” refers to an oxygen substituent that is substituted with an alkyl group. Examples of suitable alkoxy groups include, but are not limited to, -OCH3, -OCH2CH3, -O(CH2)2CH3, -OCH(CH3)2, -O(CH2)3CH3, - OCH2CH(CH3)2, -OC(CH3)3, -O(CH2)4CH3 and -O(CH2)5(CH3).

[0036] Compounds of formula (I) may exist in tautomeric forms involving the core cyclohexene motif, and many are capable of existing in differing geometric isomers and diastereomers. The compounds of formula (I) as defined herein are taken to include all tautomers, individual isomers and mixtures of isomers. Separation of individual isomers or selective synthesis of individual isomers is accomplished by application of various methods which are known to practitioners in the art.

[0037] Compounds of formula (I) may exist as solvates, for example, hydrates, and / or as salts. Examples of suitable salts include, but are not limited to, monovalent metal salts such as sodium and potassium salts, divalent metal salts such as calcium, magnesium, iron and copper salts, and ammonium salts such as isopropyl ammonium, trialkyl and tetraalkylammonium salts. Examples of suitable salts also include agriculturally acceptable salts including salts of agriculturally acceptable inorganic acids such as hydrochloric, sulphuric, phosphoric, nitric, carbonic, boric, sulfamic, and hydrobromic acids, or salts of agriculturally acceptable organic acids such as acetic, propionic, butyric, tartaric, maleic, hydroxymaleic, fumaric, maleic, citric, lactic, mucic, gluconic, benzoic, succinic, oxalic, phenylacetic, methanesulphonic, toluenesulphonic, benezenesulphonic, salicyclic, sulphanilic, aspartic, glutamic, edetic, stearic, palmitic, oleic, lauric, pantothenic, tannic, ascorbic and valeric acids. The compounds of the present disclosure are taken to include all solvates and salts thereof.

[0038] It has been found that compounds of formula (I) are effective against un- emerged pests. It is believed that compounds of formula (I) are capable of penetrating protective sheaths of un-emerged pests.

[0039] In preferred embodiments, the compound of formula (I) is wherein: X and Y are each independently selected from oxygen and sulfur; A is (C=O)R1, (C=S)R1, (CR3NR4R5), NR4R5, (C=NR4)R1 or NR4OR2; B is H or C1-C10alkyl; C, D, E and F are independently selected from H, C1-C10 alkyl, OR2 and SR2; R1 is selected from H, C1-C10 alkyl, C2-C10 alkenyl, C1-C10 haloalkyl, C1-C10 dihaloalkyl, C2-C10trihaloalkyl, C1-C10hydroxyalkyl, C1-C10thioalkyl and C1-C10nitroalkyl; R2 is selected from H and C1-C10 alkyl;R3 is selected from H, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl; R4and R5are independently selected from H, C1-C10alkyl and OR7; and R7 is selected from H and C1-C10 alkyl.

[0040] When X and Y are each independently selected from oxygen and sulfur, a compound of formula (I) is classified as a β-diketone with reference to the core cyclohexen β-dione motif of the structural formula so-formed, which defines a compound of formula (I). The term β-diketone is taken to encompass thioketones when X and Y may be selected from sulfur. In preferred embodiments, the compound of formula (I) is a β-diketone and may be referred to as a “β-diketone compound of formula (I)”.

[0041] In more preferred embodiments, the β-diketone compound of formula (I) is wherein: X and Y are each independently selected from oxygen and sulfur; A is (C=O)R1, (C=S)R1, (CR3NR4R5), NR4R5, (C=NR4)R1 or NR4OR2; B is H; C, D, E and F are independently selected from C1-C10alkyl and OR2; R1 is selected from H, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 dihaloalkyl, C2-C10 trihaloalkyl, C1-C10 hydroxyalkyl, C1-C10 thioalkyl and C1-C10 nitroalkyl; R2is H; R3is selected from C1-C10alkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl; R4 and R5 are independently selected from C1-C10 alkyl and OR7; and R7is H.

[0042] Independently, each C1-C10 alkyl, C2-C10 alkenyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, C2-C10 haloalkoxy, C1-C10 hydroxyalkyl, C1-C10 thioalkyl and C1-C10nitroalkyl may preferably be a C1-C6alkyl, C2-C6alkenyl, C2-C6haloalkyl, C2-C6 dihaloalkyl, C2-C6 trihaloalkyl, C2-C6 haloalkoxy, C1-C6 hydroxyalkyl, C1-C6 thioalkyl and C1-C6 nitroalkyl, respectively.

[0043] In more preferred embodiments, the β-diketone compound of formula (I) is selected from the group consisting of:

[0044] In more preferred embodiments, the β-diketone compound of formula (I) is selected from the group consisting of: tasmanone (1-isobutroyl-4 methoxy-3,5,5- trimethylcyclohex-3-en-2,6-dione), agglomerone (1-isobutroyl-4-methoxy-5,5- dimethylcyclohex-3-en-2,6-dione), lateriticone (1-valeroyl-4-methoxy-3,5,5- trimethylcyclohex-3-en-2,6-dione), isolateriticone (1-isovaleroyl-4-methoxy-3,5,5- trimethylcyclohex-3-en-2,6-dione) and platyphyllol (6,6-dimethyl-2-acetyl-5- methoxycyclohex-4-ene-1,3-dione). Of the β-diketone compounds of formula (I), and in particular tasmanone, these compounds are believed to possess the greatest activity against un-emerged pests. In most preferred embodiments, the β-diketone compound of formula (I) is tasmanone.

[0045] The applicability of a compound of formula (I) to the methods of the present disclosure arises from its mode of action. The primary mode of action of compounds of formula (I) is believed to be by acting as a potassium channel activator to prevent the closure of potassium channels, often leading to un-emerged pest incapacitation and specifically death of the un-emerged pest form. It is further believed that the mode of action of compounds of formula (I) arises from the core cyclohexene motif of the structural formula which defines a compound of formula (I) as described herein. It is postulated that this core motif provides the scaffold for affinity binding with un-emerged pest potassium ion channels. It is further believed that the mode of action of compounds of formula (I) is most pronounced – provides greatest biological activity – when the compound of formula (I) is a β-diketone compound of formula (I). This is attributed to the postulated greater binding affinity with un-emerged pest potassium ion channels by virtue of the core cyclohexen β-dione motif of these compounds.

[0046] Compounds of the present disclosure may be prepared according to methods analogous to those known in the art. Exemplary methods are disclosed for example in EP-A-338992, EP-A-336898, U.S. Pat. No.4,202,840, U.S. Pat. No. 4,869,748, EP-A- 186118, EP-A-186119, EP-A-186120, U.S. Pat. No.4,695,673, U.S. Pat. No.4,780,127, U.S. Pat. No.4,921,526, U.S. Pat. No.5,006,150, U.S. Pat. No.5,545,607, U.S. Pat. No. 5,925,795, U.S. Pat. No. 5,990,046, U.S. Pat. No. 6,218,579, EP-A-249150, EP-A- 137963, EP-A-394889, EP-A-506907 and EP-B-135191. Exemplary synthetic methods are given in the Examples.

[0047] Compounds of formula (I), and especially β-diketone compounds of formula (I), may also be obtained from natural sources, and particularly from volatile oil-bearing plants, for example by extraction.

[0048] Compounds of formula (I) may be used as obtained, either directly in the methods disclosed herein or formulated into a composition for use in the methods disclosed herein, as substantially purified synthetic compound, substantially purified isolated compound, in crude or in extract form. By “substantially purified” is meant that the compound of formula (I) is present in an amount of at least about 97 wt%, preferably at least about 98 wt%, 99 wt%, 99.5 wt%, 99.8 wt% and preferably 99.9 wt%. A “crude” form may be taken to be that the compound of formula (I) is present in anything less than about 97 wt%.Plant Extracts

[0049] A “plant extract” is a substance that has been extracted from a plant. Often, plant extracts containing a compound of formula (I) will contain at least one other compound that has been extracted from the plant along with the compound of formula (I). A plant extract may be crude or a substantially purified form depending on the content of compound of formula (I).

[0050] Volatile oil-bearing plants which may produce a compound of formula (I) and from which a compound of formula (I), and especially a β-diketone compound of formula (I), may be extracted, may be from the family Myrtaceae and Hypericaceae, and particularly of the genus Eucalyptus, Baeckea and Melaleuca. Representative plant species include: (for tasmanone) Eucalyptus tenuiramis, Baeckea frutescens (also agglomerone), Eucalyptus risdonii and Eucalyptus cloeziana; (for lateriticone) Eucalyptus lateritica; and (for platyphyllol) Melaleuca cajuputi. Extraction methods are known to those of skill in the art and include for example steam distillation of plant biomass.

[0051] In preferred embodiments for producing extracts containing tasmanone, the plant is selected from one or more of the Eucalyptus cloeziana varieties denoted BGTECLD29, BGTECLD14 and BGTECLD30 the subject of Australian Plant Breeder Right Application Nos.2022 / 268 filed 29 November 2022, 2022 / 267 filed 29 November 2022 and 2022 / 266 filed 26 November 2022, respectively. Samples of BGTECLD29, BGTECLD14 and BGTECLD30 are held at James Cook University, Smithfield, Cairns QLD 4870, and at Plant Biotech, 41 Menary Road, Coes Creek QLD 4560.

[0052] Plant extracts may often contain other components and are extracted from the plant along with the compound of formula (I) and as such plant extracts are often compositions.

[0053] The plant extract may contain a compound of formula (I) in an amount of at least about 40 wt%, preferably at least about 45 wt%, 50 wt%, 55 wt% or 60 wt%. In some embodiments, a compound of formula (I) is extractable from a plant in an amount of at least about 65 wt%, 70 wt%, 75 wt%, 80 wt%, 85 wt%, 90 wt% and even 95 wt% of the plant extract.

[0054] Often the plant extract may be a liquid (often an oil) in which case the plant extract may contain a compound of formula (I) in an amount of at least about 50 vol% (500 g / L), preferably at least about 55 vol% (550 g / L), 60 vol% (600 g / L), 65 vol% (650 g / L), 70 vol% (700 g / L), 75 vol% (750 g / L) and preferably 80 vol% (800 g / L). In some embodiments, a compound of formula (I) is extractable from a plant in an amount of at least about 81 vol% (810 g / L), 82 vol% (820 g / L), 83 vol% (830 g / L), 84 vol% (840 g / L) and even 85 vol% (850 g / L).

[0055] In preferred embodiments, the plant extract is a phytochemical extract. By a “phytochemical extract” is meant that the plant extract is a composition containing at least one phytochemical compound that is other than, and in addition to, any one compound of formula (I), and that has been extracted from the plant along with the compound of formula (I). A phytochemical extract is preferred because, and without wishing to be limited by theory, it is believed that an additional phytochemical may assist in the control of un-emerged pests and reducing un-emerged pest viability, by enhancing the activity of the compound of formula (I), even if only marginally. As examples, the at least one other phytochemical compound may be one or more of α- / β-phellandrene, cis- / trans-menth-2-en-1-ol, 1,8-cineole, eudesmols, eucaluptol, α-pinene, p-cymene, terpineols, terpinenes, globulol, limonene, β-myrcene, citronellal and linalool. Pests

[0056] The pests to which the present disclosure relates are arthropods. The term “pest” refers to an arthropod and is not intended to encompass mammals, marsupials, plants or micro-organisms. Most arthropods are oviparous. Oviparous arthropods represent the preferred embodiments. In preferred embodiments, the pest is an insect (an oviparous insect). In other preferred embodiments, the pest is an arachnid (an oviparous arachnid).

[0057] As used herein, an “un-emerged” pest refers to a pest in a stage of its lifecycle that contains an un-emerged pest form that is within a protective sheath which is produced by the pest itself, whether that be produced by the un-emerged pest form itself, an ancestor, an emerged form of a previous lifecycle stage, or other. An “un-emerged pest form” refers to the pest itself which is within the protective sheath. An un-emerged pest is as distinct from an “emerged pest (form)” which refers to the pest in a stage of itslifecycle that is not within the protective sheath. An un-emerged pest form is generally a pest in a developmental stage of its lifecycle where it transitions to an emerged pest form. Many un-emerged pests lack independent mobility (i.e., are sessile)

[0058] Examples of un-emerged pests include pest eggs and sheathed pupae. Pest eggs contain an embryo encased within an eggshell. In these embodiments, the embryo is the un-emerged pest form and the eggshell is the protective sheath. Examples of un- emerged pupae include chrysalises, cocoons and those having a puparium. Cocoons and chrysalises contain a pupa within a casing, the casing often comprising silk. In these embodiments, the pupa is the un-emerged pest form and the casing is the protective sheath. Other pupa may be encased within a puparium. In these embodiments, the pupa is the un-emerged pest form and the puparium is the protective sheath. The sheathed pupa may be exarate, obtect or coarctated. In preferred embodiments, the un-emerged pest is a pest egg. It has been found that compounds of formula (I), and especially β-diketone compounds of formula (I), are particularly effective against pest eggs.

[0059] The insect pests may be selected from the following: a. from the order of the lepidopterans (Lepidoptera), for example, Adoxophyes orana, Agrotis ipsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Cacoecia murinana, Capua reticulana, Choristoneura fumiferana, Chilo partellus, Choristoneura occidentalis, Cirphis unipuncta, Cnaphalocrocis medinalis, Crocidolomia binotalis, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Feltia subterranea, Grapholitha funebrana, Grapholitha molesta, Heliocoverpa armigera, Heliocoverpa virescens, Heliocoverpa zea, Hellula undalis, Hibernia defoliaria, Hypliantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Manduca sexta, Malacosoma neustria, Mamestra brassicae, Mocis repanda, Operophthera brumata, Orgyia pseudotsugata, Ostrinia nubilalis, Pandemis heparana, Panolis flamnea, Pectinophora gossypiella, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scabra, Platynota stultana, Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodenia ornithogalli, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sesamia inferens, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Syllepta derogata, Synanthedon myopaeforinis, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni, Tryporyza incertulas and Zeiraphera canadensis, also Galleria mellonella, Sitotroga cerealella, Ephestia cautella and Tineola bisselliella; b. from the order of the beetles (Coleoptera), for example, Alphitobius diaperinus, Anthonomus grandis, Anthonomus pomorum, Apion vorax, Atomaria linearis, Blastophagus piniperda, Cassida nebulosa, Cerotoma trifurcata, Ceuthorhynchus assimilis, Ceuthorhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Cryptolestes ferrugineus. Dendroctonus rufipennis, Diabrotica longicornis, Diabrotica punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorhynchus sulcatus, Otiorhynchus ovatus, Phaedon cochleariae, Phyllopertha horticola, Phyllophaga sp., Phyllotreta chrysocephala, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Psylliodes napi, Scolytus intricatus and Sitona lineatus, also Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Sitophilus granarius, Lasioderma serricorne, Oryzaephilus surinamensis, Rhyzopertha dominica, Sitophilus oryzae, Tribolium castaneum, Trogoderma granarium and Zabrotes subfasciatus; c. from the order of the dipterans (Diptera), for example, Anastrepha ludens, Ceratitis capitata, Contarinia sorghicola, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia coarctata, Delia radicum, Hydrellia griseola, Hyleniyia platura, Liriomyza sativae, Liriomyza trifolii, Mayetiola destructor, Orseolia oryzae, Oscinella frit, Pegomya hyoscyami, Phorbia antiqua,Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi and Rhagoletis pomonella, also Aedes aegypti, Aedes vexans, Aedes albopictus, Anopheles maculipennis, Chrysomya bezziana, Cochliomyia hominivorax, Chrysomya macellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis, Gasterophilus intestinalis, Haernatobia irritans, Haplodiplosis equestris, Hypoderma lineata, Lucilia cuprina, Lucilia sericata, Musca domestica, Muscina stabulans, Oestrus ovis, Tabanus bovinus and Simulium damnosum; d. from the order of the thrips (Thysanoptera), for example, Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Haplothrips tritici, Heliothrips haemorrhoidalis, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci; e. from the order of the hymenopterans (Hymenoptera), for example, Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Iridomyrmex humilis, Iridomyrmex purpureus, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri and Technomyrmex albipes; f. from the order of the heteropteranis (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus ictericus, Leptoglossus phyllopus, Lygus hesperus, Lygus lineolaris, Lygus pratensis, Mormidea pictiventris, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor; g. from the order of the homopterarts (Homoptera), for example, Acyrthosiphon onobrychis, Acyrthosiphon pisum, Adelges laricis, Aonidiella aurantii, Aphidula nasturtii, Aphis fabae, Aphis gossypii, Aphis pomi, Aulacorthum solani, Bemisia tabaci, Brachycaudus cardui, Brevicoryne brassicae, Dalbulus maidis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosorna lanigerum, Laodelphax striatella, Macrosiphum avenae, Macrosiphun euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzus persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla pyri, Psylla pyricola, Rhopalosiphummaidis, Schizaphis graminum, Sitobion avenae, Sogatella furcifera, Toxoptera citricida, Trialeurodes abutilonea, Trialeurodes vaporariorum and Viteus vitifolaei; h. from the order of the termites (Isoptera), for example, Kalotermes flavicollis, Coptotermes spp, Leucotermes flavipes, Macrotermes subhyalinus, Macrotermes darwiniensis, Mastotermes spp. Microtermes spp., Nasutitermes spp such as Nasutitermes walkeri, Odontotermes formosanus, Reticulitermes lucifugus and Termes natalensis; i. from the order of the orthopterans (Orthoptera), for example, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Schistocerca gregaria, also Acheta domesticus, Blatta orientalis, Blattella germanica and Periplaneta americana; j. from the order of the phthirapterans (Phthiraptera), for example, Mallophaga, such as Damalina spp., and Anoplura such as Linognathus and Haematopinus spp., and Pediculus spp.; k. from the order of the hemnipterans (Hemiptera), for example, Aphis, Aleurocanthus, Bemisia, Phorodon, Aeneolamia, Empoasca, Perkinsiella, Pyrilla, Aonidiella, Coccus, Pseudococcus, Helopeltis, Lygus, Dysdercus, Oxycarenus, Nezara, Aleyrodes, Triatoma, Psylla, Myzus, Megoura, Phylloxera, Adelges, Nilaparvata, Nephotettix or Cimex spp.; l. from the order of the siphonapterans (Siphonaptera), for example, Ctenocephalides or Pulex spp.; m. from the order of the thysanurans (Thysanura), for example, Lepisina spp.; n. from the order of the dermapterans (Dermaptera), for example, Forficula spp.; and o. from the order of the psocopterans (Psocoptera), for example, Peripsocus spp.

[0060] The arachnid pest may for example be selected from a spider, pseudoscorpion, microscopion, mite and tick. Preferably the arachnid pest is selected from a mite, tick and spider, and preferably selected from the following:a. Mites such as Aculops lycopersicae, Aculops pelekassi, Aculus Schlechtendali, Brevipalpus phoenicis, Brevipalpus californicus, Bryobia praetiosa, Bryobia rubrioculus, Dermanyssus gallinae, Eotetranychus carpini, Eotetranichus lewisi, Eutetranychus banksia, Eutetranychus orientalis, Eriophyes sheldoni, Eryophyes tiliae, Eriophyes inangulis, Eriophyes vitis, Oligonychus pratensis, Oligonychus coffeae, Oligonitis oryzae, Oligonychus milleri, Panonychus ulmi, Panonychus citri, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Sarcoptes scabiei, Tarsonemus pallidus, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus and Tetranychus urticae. b. Ticks such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus miccroplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Rhipicephalus apendiculatus, Rhipicephalus evertsi and Rhipicephalus microplus. c. Spiders such as Lampona species (e.g. L. cylindrata, L. murina), Badumna species (e.g. B. insignis, B. longinqua), Steatoda grossa, Cheiracanthium species (e.g. C. punctorium, C. mildei, C. inclusum, C. lawrencei, C. japonicum, C. mildei), Parasteatoda tepidariorum, Kukulcania hibernalis, Eratigena species (e.g. E. agrestis, E. atrica), Tegenaria domestica, Pholcus phalangioides, Argiope keyserlingi, Hunstman spiders (of the family Sparassidae), Wolf spiders (of the family Lycosidae), Latrodectus species (e.g. L. hasselti, L. mactans, L. tredecimguttatus), Atrax robustus, Hadronyche species (e.g. H. formidabilis, H. cerberea, H. versuta, H. infensa, H. macquariensis), Loxosceles reclusa, Jumping spiders (of the family Salticidae) and Araneus diadematus.

[0061] Preferably the pest is a parasitic pest of a plant or animal. In preferred embodiments, the pest is selected from the order of the Siphonaptera and particularly Ctenocephalides or Pulex species, from the Hemiptera or Homoptera and particularly Cimex, Bemisia, Aleurocanthus, Trialeurodes or Aleyrodes species, from the order of the Phthiraptera and particularly Pediculus spp., from mites and particularly Tetranychus species, and from ticks and particularly Ixodes and Ornithodorus species.

[0062] The pest may be a pesticide-resistant pest or a pesticide-susceptible pest. As used herein, the term “pesticide-resistant pest” is meant that the pest has developed resistance to one or more pesticides previously used to control it. A “pesticide-susceptible pest” is a pest that has not developed resistance to one or more other pesticides.

[0063] A pesticide-resistant pest may be present in a population of pests. A pesticide- resistant pest may be resistant to any one or more pesticides selected from the group cosnsiting of a sodium channel modulator, an acetylcholinesterase (AchE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinergic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a juvenile hormone mimic, a homopteran feeding blocker, a mitochondrial ATP synthase inhibitor, an uncoupler of oxidative phosphorylation, a nicotinic acetylcholine receptor channel blocker, an inhibitor of chitin biosynthesis, a moulting disruptor, an ecdysone receptor agonist or disruptor, an octopamine receptor, a mitochondrial complex I electron transport inhibitor, an acetyl CoA carboxylase inhibitor, a voltage-dependent sodium channel blocker, a mitochondrial complex IV electron inhibitor, a mitochondrial complex IV electron transport inhibitor, a ryanodine receptor modulator and an insect growth regulator. Methods

[0064] The methods of the disclosure relate to reducing the viability of an un- emerged pest, and / or controlling un-emerged pests, by exposing an un-emerged pest to an effective amount of a compound of formula (I) as described herein.

[0065] As used herein, the term “reducing viability” refers to reducing an ability of an un-emerged pest to emerge at all, or to emerge with an uninhibited reproductive capacity. The reduced viability may be determined by comparison with a pest that has not been exposed to a compound of formula (I). A physical deformity which makes an emerged pest less attractive to mating partners is encompassed within what constitutes an inhibited reproductive capability. An emerged pest which is exposed to a compound of formula (I) when un-emerged and dies prior to reaching reproductive maturity, or is otherwise inhibited in reproductive capability, as a result of the exposure, is encompassed within what constitutes an inhibited reproductive capability.

[0066] As described above, the applicability of a compound of formula (I), and especially a β-diketone compound of formula (I), to the methods of the present disclosurearises from its mode of action as a potassium channel activator. It is thought that potassium ion channels play a particularly important role in the development of un- emerged pest forms and especially egg embryos, and it is postulated that there is a relative abundance of potassium ion channels in un-emerged pest forms and especially embryos, similar to the abundance found in their nymph and adult form counterparts.

[0067] It has furthermore surprisingly been found that compounds of formula (I), and especially β-diketone compounds of formula (I), are capable of penetrating protective sheaths of un-emerged pests and especially eggshells, in sufficient quantity to be effective against un-emerged pest forms. It is thought that un-emerged pest forms including embryos do not produce enzymes which are capable of break-down of compounds of formula (I).

[0068] Accordingly, compounds of formula (I) and especially β-diketone compounds of formula (I), are particularly effective in the control of pests when un-emerged pests are exposed thereto, and particularly effective in reducing the viability of un-emerged pest, especially pest eggs, when exposed thereto. This is to advantage. The majority of pest control strategies target emerged pest forms – larvae, nymphs and adults – as they are generally the easiest to control. This is in part because the emerged forms are susceptible to chemical control methods, while un-emerged forms may be minimally susceptible or not at all to certain chemical agents. The efficacy of compounds of formula (I) in the control of un-emerged pests provides another avenue of pest control.

[0069] In preferred embodiments, the un-emerged pest form is killed or otherwise caused to be in a moribund state, preferably killed.

[0070] An un-emerged pest with reduced viability may equally be referred to as an incapacitated un-emerged pest. Incapacitation may be by way of killing or otherwise causing the un-emerged pest to be in a moribund state or reducing an ability of an un- emerged pest to emerge with an uninhibited reproductive capacity. Accordingly, methods of reducing the viability of an un-emerged pest may equally be referred to as methods for incapacitating an un-emerged pest.

[0071] The un-emerged pests may be incapacitated or controlled by applying to the un-emerged pests or to an environment containing the un-emerged pests an effective amount of a compound of formula (I) or composition containing it, so as to expose the un-emerged pest to a compound of formula (I).

[0072] As used herein, the term “environment” refers to an environment that hosts or may be host to un-emerged pests, to which a compound of formula (I) may be applied to expose the un-emerged pests thereto. An environment may be a household or industrial environment, which environments are generally inhabited by humans and / or animals. A household environment is one generally used for leisure, such as a house, gymnasium, leisure centre, other buildings, rooms thereof and furniture therein, shed, cupboard or other storage space, tent, patio, verandah and the like, whereas an industrial environment is one generally used for industrial purposes such as manufacture, storage or vending of products, such as a warehouse, manufacturing plant, retail outlet, factory, other building, rooms thereof, furniture and equipment therein, and the like. An environment may be an agricultural environment, which is generally an industrial environment used for agricultural purposes and includes, for example, environments for crop cultivation, storage and / or cartage of agricultural goods, food processing, animal housing and the like such as a field, greenhouse, silo, shed, stable and the like.

[0073] Pests generally reproduce through a lifecycle involving a sequence of un- emerged and emerged pest forms – emerged pests (e.g. adults) give rise to un-emerged pests (e.g. by laying eggs), and un-emerged pest grows into emerged pest, and so-on.

[0074] As used herein, the term “controlling” in context of a pest refers to inhibiting the pest, in any form including adult forms, from participating in activities in an environment in population numbers causing it to be a pest in that environment. This is achieved by exposing the un-emerged pest to a compounds of formula (I) which reduced the viability of the un-emerged pest leading to a reduced ability, or an inability, to produce emerged pest forms in the next stage of the lifecycle or to reproduce to produce a subsequent generation of pest, ultimately leading to a reduced pest population. Compounds of formula (I) may also be active against emerged pest forms and so control may also in part be achieved by reducing emerged pest populations, but in the context of the present disclosure requires un-emerged pest incapacitation component. Control of pests does not necessarily require complete eradication of all pests of a population from an environment but may be achieved by limiting or reducing active population numbers to a level where the pest ceases to be pestilent in that environment. What constitutes control of a pest in terms of pest population numbers may differ between the particular pest, the population and the environment, and is determinable by one of skill in the art.

[0075] That said, often complete, near-complete or at least substantial elimination of a pest population from an environment is desirable.

[0076] Accordingly, in preferred embodiments, a pest is controlled by reducing pest population numbers in an environment by at least 50%, 55%, 60%, 65% or 70%, more preferably at least 75%, 80%, 85%, 90% or 95%, and more preferably as much as 98%, 99% or even 100%.

[0077] Often un-emerged pests are present in a population. For instance, a single female adult pest may be capable of laying multiple eggs at a time. Accordingly, in preferred embodiments, the viability of at least 50%, 55%, 60%, 65% or 70%, more preferably at least 75%, 80%, 85%, 90% or 95%, and more preferably as much as 98%, 99% or even 100%, of the un-emerged pest population is incapacitated. An incapacitated un-emerged pest may show physical signs of incapacitation such as off-colour, shape or size change, and so an incapacitated un-emerged pest may be identified by viewing the un-emerged pest for a physical change. An incapacitated un-emerged pest may also be identified as a pest that remains un-emerged after it would usually have emerged during its lifecycle timeframe.

[0078] The time after exposure to a compound of formula (I) at which the achieved control of pests is determined may be tied to the lifecycle timeframe of the pest being controlled, especially if eradication of emerged pests is desired. For instance, eggs of a given insect species may hatch, say, four days after being laid. Accordingly, if exposure occurs on day one, the time after exposure at which the control achieved may be determined may be after four days when the eggs are due to hatch.

[0079] Compounds of formula (I) and especially β-diketone compounds of formula (I), tend to be volatile and thus when applied to an environment remain active in that environment for generally only a short period of time after application. This may be referred to as the “active window”. The active window may depend on the particular compound of formula (I), components of a composition containing it, the environment, amount applied and susceptibility of the un-emerged pest, but in general terms may be for one to several hours after application, such as 2, 4, 6, 8, 10, 12, 14, 16, 18, 20 or 22 hours after application, but generally no more than about 1 day (24 hours) after application. Accordingly, an emerged pest which has been exposed to a compound of formula (I) when un-emerged, and which dies prior to reaching reproductive maturity oris otherwise inhibited in reproductive capability, especially outside of the active window, may be attributed to the exposure of the un-emerged pest to the compound of formula (I). Further, some other chemical control agents are not lethal but rather act as repellants and agents for temporary incapacitation – knockdown – from which at least some of a pest population may recover. It is to advantage that compounds of formula (I) are capable of lethality.

[0080] As used herein, the term “effective amount” in context of a compound of formula (I) is meant an amount that is sufficient to reduce un-emerged pest viability or control pests by exposure of the un-emerged pest thereto.

[0081] An effective amount may be represented by an LC (lethal concentration) or an LD (lethal dose) amount; that is a concentration or dosage, respectively, that is effective for incapacitating – preferably killing – a percentage of un-emerged pests in an un-emerged pest population or controlling pests by un-emerged pest exposure. They essentially come to an amount of compound to which an un-emerged pest should be exposed in order to be likely incapacitated, and are extrapolatable to amounts to be applied to an environment containing un-emerged pests to ensure that the un-emerged pests in that environment are exposed to that amount.

[0082] LC and LD amounts for any given pest may differ between pest species and is determinable by one of skill in the art through routine trials. That said, generally speaking, an effective amount may be at least an LC50amount, preferably at least an LC55, LC60, LC65, LC70, LC75, LC80 or LC85 amount (or equally an LD amount), being the concentration that incapacitates un-emerged pests or reduced pest population numbers by 50%, 55%, 60%, 65%, 70%, 75%, 80% or 85%, respectably. Often in pest control complete, near-complete or at least substantial elimination of a pest population from an environment is desirable. Accordingly, in preferred embodiments an effective amount may be at least an LC90amount, preferably an LC91, LC92, LC93or LC94amount, more preferably at least an LC95, LC96, LC97, LC98 or LC99 amount, or even an LC100 amount (or equally an LD amount).

[0083] The physical amount of the compound of formula (I) that constitutes an effective amount may be dependent on the particular pest, its susceptibility to the compound, level of infestation, and the type of control desired, and is determinable by one of skill in the art with the following guidance. Generally speaking, the compound offormula (I) may be applied to an environment at a lower limit, being in an amount of at least about 50 g / ha (0.005 g / m2), 100 g / ha (0.01 g / m2), 200 g / ha (0.02 g / m2), 300 g / ha (0.03 g / m2), 400 g / ha (0.04 g / m2), 500 g / ha (0.05 g / m2), 1,000 g / ha (0.1 g / m2), 2,000 g / ha (0.2 g / m2), 3,000 g / ha (0.3 g / m2) or 4,000 g / ha (0.4 g / m2). Preferably, the compound of formula (I) may be applied to an environment in an amount of at least about 50 g / ha (0.005 g / m2), 100 g / ha (0.01 g / m2), 200 g / ha (0.02 g / m2), 300 g / ha (0.03 g / m2) or 400 g / ha (0.04 g / m2). The compound of formula (I) may be applied to an environment in an amount of up to or at least about 11,000 g / ha (1.1 g / m2) or 12,000 g / ha (1.2 g / m2), including for example up to or at least about 15,000 g / ha (1.5 g / m2) or 20,000 g / ha (2.0 g / m2). The compound of formula (I) may be applied to an environment at an upper limit in an amount of up to about 40,000 g / ha (4.0 g / m2), 35,000 g / ha (3.5 g / m2), 30,000 g / ha (3.0 g / m2), 29,000 g / ha (2.9 g / m2), 28,000 g / ha (2.8 g / m2), 27,000 g / ha (2.7 g / m2), 26,000 g / ha (2.6 g / m2), 25,000 g / ha (2.6 g / m2) or 24,000 g / ha (2.4 g / m2). Any upper and lower limit may be combined without limitation. For example, the compound of formula (I) may be applied to an environment in an amount of from about 50 g / ha (0.005 g / m2) to about 30,000 g / ha (3.0 g / m2), or from about 6,000 g / ha (0.6 g / m2) to about 24,000 g / ha (2.4 g / m2) or from about 200 g / ha (0.02 g / m2) to about 24,000 g / ha (2.4 g / m2), or from about 100 g / ha (0.01 g / m2) to about 12,000 g / ha (1.2 g / m2) etc. These amounts and ranges are believed to be applicable to a broad range of pests. In preferred embodiments, the compound of formula (I) is applied to an environment in an amount of from about 50 g / ha (0.005 g / m2) to about 30,000 g / ha (3.0 g / m2), or about 100 g / ha (0.01 g / m2) to about 24,000 g / ha (2.4 g / m2), or about 200 g / ha (0.02 g / m2) to about 15,000 g / ha (1.5 g / m2), or about 300 g / ha (0.03 g / m2) to about 12,000 g / ha (1.2 g / m2). In some embodiments, for example in an agricultural environment, the compound of formula (I) is applied to an environment in an amount of from about 50 g / ha (0.005 g / m2) to about 4,000 g / ha (0.4 g / m2), or about 100 g / ha (0.01 g / m2) to about 3,000 g / ha (0.3 g / m2), or about 200 g / ha (0.02 g / m2) to about 2,000 g / ha (0.2 g / m2), or about 300 g / ha (0.03 g / m2) to about 1,000 g / ha (0.1 g / m2). Combinations

[0084] The compound of formula (I) may be applied alone (as the only pesticide) or in combination with a second pesticide. A “second pesticide” is taken to mean other thana pesticidal compound extracted from a plant along with a compound of formula (I). A “combination” means that the compound of formula (I) and the second pesticide are used together, whether in a single composition or separately or sequentially in separate compositions, such that the biological activity of the compound of formula (I) and the second pesticide occurs at the same time or overlaps.

[0085] When the compound of formula (I) is used with a second pesticide, one or both of the second pesticide and the compound of formula (I), preferably both, may be used in a sub-effective amount. As used herein, the term “sub-effective amount” in the context of a pesticide is meant an amount that is less than that which, when the pesticide is used alone, is effective for reducing the viability of an un-emerged pests or controlling pests by exposure of un-emerged pests thereto. That is, a sub-effective amount of a pesticide is less than an effective amount of that pesticide. For example, in the case of reducing the viability of an un-emerged pest, when the effective amount of a pesticide is an LC100 amount, a sub-effective amount is less than an LC100 amount (an LC<100 amount), which may be for example an LC99, LC95, LC90, LC85, LC80, LC75, LC70, LC65, LC60, LC55, LC50, LC45,LC40, LC35, LC30, LC25, LC20, LC15, LC10or LC5amount. Similarly, when the effective amount of a pesticide is an LC50 amount, a sub-effective amount is less than an LC50 amount (an LC<50 amount) which may be for example and LC45,LC40, LC35, LC30, LC25, LC20, LC15, LC10or LC5amount. The same principle is equally applicable to e.g. LD amounts.

[0086] When the compound of formula (I) is used with a second pesticide, one or both of the second pesticide and the compound of formula (I), preferably both, may be used in a sub-additive amount. As used herein, a “sub-additive amount” in the context of a pesticide is meant an amount that, when the effects of each pesticide when used alone are added together, would not be effective for controlling the pests. In other words, a combination effective for controlling pests that comprises a sub-additive amount of a compound of formula (I) and a second pesticide, is a synergistic combination; that is, super-additive. For example, in the case of reducing the viability of an un-emerged pest, and using the same example as above based on an LC amount, when the effective amount of a combination is an LC100amount, a sub-additive amount of each of the compound of formula (I) and the second pesticide is an amount that, when the effects of each of which when used alone are added together, is less than an LC100amount. In other words, andgenerally speaking, the percentage of a pest population that each of the compound of formula (I) and the second pesticide incapacitates, when used alone, does not amount to control of the pest, but when used together the pest is controlled. The same principle is equally applicable to LD amounts. For example, in a super-additive combination, the amount of the compound of formula (I) used in the combination may be an LC5, LC10, LC20, LC30, LC40, LC50, LC60, LC70, LC80, LC90or LC95amount, while the amount of the second pesticide may be less than an LC95, LC90, LC80, LC70, LC60, LC50, LC40, LC30, LC20, LC10 or LC5 amount, respectably. The same principle is equally applicable to LD amounts.

[0087] In preferred combinations, at least one second pesticide has a different mode of action from the compound of formula (I).

[0088] Many second pesticides are generally known in the art and may be obtained commercially. Examples fall into the mode of action categories of a sodium channel modulator, an acetylcholinesterase (AchE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinergic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a juvenile hormone mimic, a homopteran feeding blocker, a mitochondrial ATP synthase inhibitor, an uncoupler of oxidative phosphorylation, a nicotinic acetylcholine receptor channel blocker, an inhibitor of chitin biosynthesis, a moulting disruptor, an ecdysone receptor agonist or disruptor, an octopamine receptor, a mitochondrial complex I electron transport inhibitor, an acetyl CoA carboxylase inhibitor, a voltage-dependent sodium channel blocker, a mitochondrial complex IV electron inhibitor, a mitochondrial complex IV electron transport inhibitor, a ryanodine receptor modulator and an insect growth regulator.

[0089] Certain exemplary second pesticides which are particularly applicable include thiodicarb, emamectin, flubendiamide, indoxacarb, chlorantraniliprole, spinosad, novaluron, chlorfenapyr, lufenuron, cyantraniliprole, fenvalerate, diflubenzuron, triprene, methomyl, synthetic pyrethroids including permethrin and cypermethrin, and pyrethrins.

[0090] The amount of the second pesticide to be used may be determined based on its label including sub-effective and sub-additive amounts with guidance as provided herein. In some combinations, the amount of the compound of formula (I) used in the combination is the same or greater than the amount of the at least one second pesticideused in the combination, or in other words, the amount of the at least one second pesticide used in the combination is the same or less than the amount of the compound of formula (I) used in the combination. Compositions

[0091] The compound of formula (I) may be used neat or in a composition along with other components. A plant extract may constitute a composition, including a phytochemical extract, as described herein.

[0092] The compound of formula (I) or plant extract containing it may be formulated together with other components. As compounds of formula (I) and especially β-diketone compound of formula (I) tend to be liquid at atmospheric conditions, then a formulation may be formulated in any suitable way, preferably a liquid formulation. This may be by means of dissolving, emulsifying, suspending, or other. That said, impregnation to or capture within a release form is also contemplated, such as a gel, granules or micro- capsule.

[0093] A formulation may be formulated as a concentrate or a diluted ready-to-use formulation.

[0094] Other components include but are not limited to a second pesticide as described herein and adjuvants such as a solvent, carrier, surfactant, defoaming agent, deposition aid, stabiliser, thickener, emulsifier, wetting agent, synergist, humecant, dye and buffering agent. Many adjuvants are generally known in the art and may be obtained commercially. Natural ingredients are preferred.

[0095] When one or more second pesticides are used, it is preferred that the compound of formula (I) and the one or more second pesticides are formulated together in a single composition.

[0096] Appropriate formulation selection may be made with consideration of the pest and environment of application and any second pesticide included. Suitable formulations are determinable by one of skill in the art. Formulation methods and techniques are known to those of skill in the art.

[0097] In preferred embodiments, the compound of formula (I) is included as a plant extract and formulated with other components.

[0098] A liquid composition for broadcast application as a spray is preferred. As a compound of formula (I) and plant extracts containing it tend to be oils, the composition may be formulated as an emulsion in water.

[0099] The composition may be formulated with a concentration of the compound of formula (I) and one or more second pesticides, if present, appropriate for the method of application and pest to be controlled. In preferred embodiments, the composition is formulated with a concentration of compound of formula (I) in the range of about 10 g / L to 400 g / L, 30 g / L to 240 g / L or 60 g / L to 240 g / L. The concentration of compound of formula (I) may also be expressed as a volume %, in which case a composition may be formulated with a concentration of compound of formula (I) in the range of about 0.9 vol% to 50 vol%, 2.5 vol% to 30 vol% or 5 vol% to 30 vol%. Using these concentrations, the effective amount of the compound of formula (I) as described above may be achieved with an application rate of about 100-200 L / hectare (10-20 mL / m2). Kits

[0100] The compound of formula (I) may also be provided in a kit. The kit may include other components for formulating a composition including one or more second pesticide. The kit may include instructions for exposing un-emerged pests to a compound of formula (I) and optionally instructions for formulating a composition containing a compound of formula (I). The instructions may contain application rates and techniques suitable for specific pests, and optionally formulation instructions, preferably in accordance with the preferred embodiments herein described. Representative Embodiments

[0101] Preferred embodiments of the methods described herein are wherein the compound of formula (I) is a β-diketone compound of formula (I) and preferably is selected from tasmanone (1-isobutroyl-4 methoxy-3,5,5-trimethylcyclohex-3-en-2,6- dione), agglomerone (1-isobutroyl-4-methoxy-5,5-dimethylcyclohex-3-en-2,6-dione), lateriticone (1-valeroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), isolateriticone (1-isovaleroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione) and platyphyllol (6,6-dimethyl-2-acetyl-5-methoxycyclohex-4-ene-1,3-dione), preferably tasmanone, and one or more of:a. the compound of formula (I) is provided as a plant extract, preferably a phytochemical extract, preferably containing at least 80 wt% of a compound of formula (I); b. the un-emerged pest is a pest egg; c. the pest is a parastitic pest of a plant or animal, preferably selected from the order of the Siphonaptera and particularly Ctenocephalides or Pulex species, from the Hemiptera and particularly Cimex species, from the order of the Phthiraptera and particularly Pediculus spp., from mites and particularly Tetranychus species, and from ticks and particularly Ixodes and Ornithodorus species; d. reducing the viability of the un-emerged pest and controlling pests is by killing the un-emerged pest form or by killing an emerged pest form as a result of exposure of the un-emerged form to a compound of formula (I); e. the compound of formula (I) is applied to an environment in an amount of from about 50 g / ha (0.005 g / m2) to about 30,000 g / ha (3.0 g / m2), or about 100 g / ha (0.01 g / m2) to about 24,000 g / ha (2.4 g / m2), or about 200 g / ha (0.02 g / m2) to about 15,000 g / ha (1.5 g / m2), or about 300 g / ha (0.03 g / m2) to about 12,000 g / ha (1.2 g / m2). In some embodiments, the compound of formula (I) is applied to an environment in an amount of from about 50 g / ha (0.005 g / m2) to about 4,000 g / ha (0.4 g / m2), or about 100 g / ha (0.01 g / m2) to about 3,000 g / ha (0.3 g / m2), or about 200 g / ha (0.02 g / m2) to about 2,000 g / ha (0.2 g / m2), or about 300 g / ha (0.03 g / m2) to about 1,000 g / ha (0.1 g / m2).; f. the compound of formula (I) is used in a sub-effective or a sub-additive amount; and g. a composition is used containing a concentration of compound of formula (I) in the range of about 10 g / L to 400 g / L, 30 g / L to 240 g / L or 60 g / L to 240 g / L. EXAMPLES

[0102] A compound of formula (I) may be prepared synthetically. In a first representative procedure of Scheme 1, 3-methoxy-2,4,4-trimethylcyclohex-2-en-1,5- dione (1 mole eq), is dissolved in anhydrous diethylether and hexamethyl- phosphoramide(solvent ratio, 20:1) under an atmosphere of nitrogen. The mixture is cooled to 0° C and lithium hydride (1.1 mole eq) (60% in mineral oil) is added in portions. The mixture is stirred for 10 minutes before the addition of cyanide reagent R1-CO-CN, R1being as defined above (1.1 mole eq). The mixture is allowed to warm to room temperature over 12 hours at which time the reaction is quenched with water and partitioned. The ether layer is dried (Na2SO4) and evaporated affording crude compound which is purified by SiO2 column chromatography (hexane / ethyl acetate, gradient).Scheme 1

[0103] In a second representative procedure, 3-methoxy-2,4,4-trimethylcyclohex-2- en-l,5-dione (1 mole eq) (commercially available) and cyanide reagent R1-CO-CN, R1being as defined above, are dissolved in anhydrous dichloromethane and cooled to 0° C under an atmosphere of nitrogen. To the cooled solution is added anhydrous finely powdered zinc chloride (1.1 mole eq.) followed by slow addition of triethylamine (1.2 mole eq). The reaction mixture is stirred at room temperature for 5-6 hours and then poured into 2 M hydrochloric acid. The mixture is partitioned and the dichloromethane layer is washed with 5% sodium carbonate. The aqueous carbonate phase is then acidified with hydrochloric acid and extracted with methylene chloride and dried (Na2SO4). The solvent is removed and the residue subjected to SiO2column chromatography.

[0104] Metal salts may be prepared by the reaction of the prepared compounds with corresponding metal hydroxides suspended in methanol or ethanol. Trialkylammonium salts can be prepared by the reaction of the prepared compounds with trialkylamines in a chlorinated solvent such as dichloromethane. Tetraalkylammonium salts can be prepared by adding a halogenated tetraalkylammonium salt to a metal salt in dichloromethane.Example 1: Ovicidal Activity against Eggs of Cimex lectularius Summary

[0105] A series of laboratory bioassays were conducted to determine the ovicidal activity of a 540 g / L EW formulation of extract oil of Eucalyptus cloeziana containing 80.66 wt% tasmanone (Qcide 540 EW) against bed bugs, Cimex lectularius, in terms of egg hatch inhibition / mortality in the egg or nymph stage.

[0106] Adult bed bugs were placed on filter paper within a holding container and were left until a sufficient number of eggs were laid, after which the adults were removed. The filter papers containing the eggs were then placed into the test units which comprised of a transparent plastic container (12 cm in diameter). Treatments were applied as a topical spray, via a Potter tower, pre-calibrated to deliver a spray volume of 1 g solution per 100 cm2. The lids of the test units were left unsecured for 1-hour after the spray to allow any vapour to dissipate. Assessments were carried out at approximately 3, 7 and 14 days post treatment application. Five replicates were undertaken for each treatment and approximately 15 eggs were included per replicate.

[0107] Spray application of Qcide 540 EW resulted in high combined nymph and ovicidal activity at rates above 6000 mg ai / L. Mortality remained low in water control tests (0% mortality at 14 days). Methodology

[0108] Adult bed bugs, Cimex lectularius, insecticide-susceptible strain, were placed on filter papers within a holding container and left for approximately 2 days to lay eggs. After 2 days, the adults were removed and the number of eggs deposited on the filter papers were counted. The filter papers were split, using scissors, so that approximately 15 eggs were included per replicate. The filter paper containing the eggs were placed into individual test units which consisted of transparent plastic containers (12 cm in diameter) with pin holes added to the lid for ventilation. The number of eggs included was recorded on the lid of the test unit.

[0109] Two treatment schedules were undertaken: an initial range finder and a definitive range finder. Both used five replicates of a series of treatment amounts of Qcide 540 EW, the latter being refined based on the results of the former (Table 1). Treatment amounts were prepared by dilution in deionised water with no additional adjuvant / wetting agents. Test solutions were prepared in plastic beakers and hand mixed using a stirrer.Table 1. Treatment schedules. ates

[0110] The test units containing the eggs were sprayed individually using the Potter Tower (Burkard, United Kingdom), pre-calibrated to deliver spray volume of 1 g solution per 100 cm2. After treatment, the lids of the units remained unsecured for 1 hour, to allow any vapour from the units to dissipate. After 1 hour, the lids were returned. During the experimental period the temperature ranged from 25.0° C to 27.4° C for the initial range finder, and from 25.2° C to 29.3° C for the definitive range finder. Assessments were conducted at approximately 3, 7 and 14 days post treatment application. The proportion of live, dead eggs / nymphs present were assessed (Figure 2). Results

[0111] Results are presented in graphical and tabular format. Percentage mean values and standard error were calculated. A Probit analysis was conducted using ToxRat Professional version 3.3. Results from the tests are summarised in Table 2. The Probit analysis was conducted on the combined ovicidal and nymph mortality results to give a total mortality for the treatment rate.

[0112] In the initial range finder treatment schedule, a mortality effect was noted at rates 3000 mg ai / L and 30000 mg ai / L with 30% and 97.3% ovicidal mortality recorded, respectively, and 1.5% and 2.7% nymph mortality recorded, respectively (Table 2, Figure 2).

[0113] In the definitive range finder treatment schedule, rates of 1500mg ai / L, 3000mg ai / L, 6000mg ai / L, 12000mg ai / L and 24000mg ai / L resulted in 1.3%, 0%, 12.9%, 26.2%, and 32.5% ovicidal mortality at 14 days, respectively. Mortality of nymphs from emerged eggs at rates of 1500mg ai / L, 3000mg ai / L, 6000mg ai / L, 12000mg ai / L and 24000mg ai / L was observed as 1.3%, 11.3%, 52.8%, 72.2% and 67.5%, respectively, at 14 days post spray application (Table 3). Mortality remained low in water control tests. Exposure of the eggs to tasmanone was believed to have contributed to the nymph mortality at 14-days.±s± nsa n eaee eyayda-4d- 1 4 a1rearveo v obd bedbefb ofyotiy latitrlaotro mhmp hp my m n y dnn d a n laaldaicidivcio v e o geatg naec.t)n.)re5e=cr5= p ne,pn naesrn,osMrrae rorr.eMe2dr.3 d el ab delrab d anTatsanTatsExample 2: Ovicidal Activity against Eggs of Tetranychus kanzawai

[0114] Ten female adult mites of Tetranychus kanzawai were released on a separate kidney bean leaf disc and were allowed to lay eggs on it. Next day, the number of laid eggs was counted and 8 mL of diluted solution of a 200 g / L EC formulation of extract oil of Eucalyptus cloeziana containing at least 75 wt% tasmanone (Qcide 200 EC) of appropriate concentration (Table 4) was sprayed on a leaf disc. After spraying, treated leaf discs were incubated under condition of 25oC and 70% RH. The number of hatched eggs was counted 5 days after the treatment (Table 4). Table 4. Results of ovicidal activity study against eggs of Tetranychus kanzawai.Example 3: Ovicidal Activity against Eggs of Tetranychus urticae Summary

[0115] A series of laboratory bioassays were conducted to determine the ovicidal activity of a 540 g / L EW formulation of extract oil of Eucalyptus cloeziana containing 80.66 wt% tasmanone (Qcide 540 EW) against two-spotted spider mite (TSM), Tetranychus urticae, in terms of egg hatch inhibition / mortality in the egg or nymph stage.

[0116] Test units comprised transparent plastic sauce pots containing 1% pre-set agar onto which dwarf French bean leaf discs were placed. Approximately 15 adult TSM were introduced per test unit which were then left for 24-hours for the spider mites to lay eggs. After 24-hours the adult spider mites were removed, and the number of eggs counted. Approximately 15 eggs were included per test unit. Treatments were applied as a topical spray, via a Potter tower (Burkard, United Kingdom), pre-calibrated to deliver a spray volume equivalent to 500L / Ha (0.5 g solution per 100 cm2). The lids of the test units were left unsecured for 1-hour after the application of the spray to allow any vapour to dissipate. Assessments were carried out at 1 and 5-days post treatment application. Five replicates were undertaken for each treatment.

[0117] Spray application of Qcide 540 EW at rates 375 mg ai / L, 750 mg ai / L, 1500 mg ai / L, 2250 mg ai / L and 3000 mg ai / L against TSM eggs resulted in 3.2%, 33.2%, 74.6%, 86.8%, and 91.7% ovicidal mortality at 5-days respectively. Mortality remained low in water control tests (<2% ovicidal mortality at 5-days). Methodology

[0118] Treatments were diluted in deionised water with no additional adjuvant / wetting agents added. Test solutions were prepared in plastic beakers and hand mixed using a stirrer. A series of serial dilutions of Qcide 540 EW in deionised water were prepared. The five test rates selected were informed by an initial range finder, the results for which are shows in Figure 3 and Table 5.

[0119] The test units containing the eggs were sprayed individually using the Potter Tower (Burkard, United Kingdom), pre-calibrated to deliver spray volume and coverage equivalent to 500L / Ha (0.5 g solution per 100 cm2). After treatment, the lids of the units remained unsecured for 1 hour, to allow any vapour from the units to dissipate, at 1 hour the lids were returned and the test units were placed in a climate-controlled cabinet.

[0120] A dwarf French bean leaf disc of approximately 30 mm in diameter was placed on a 1% agar bed within a 55 mm diameter sauce pot, with the abaxial aspect of the leaf faced upwards.20x adult mixed sex mites were transferred manually from a stock culture, using an artist's paint brush. These units containing the adult mites were held within a climate-controlled cabinet.

[0121] After 24 hours, the number of eggs deposited on each leaf disc was counted (approximately 15 eggs per test unit) and the number of eggs was recorded on the lid of the test unit. If too many eggs were laid, excess eggs were removed from the test unit (using a paint brush or removing a section of leaf disc). Adult mites were removed from test units before treatment application, to prevent additional eggs being laid.

[0122] Assessments were conducted at 1 and 5-days post treatment application, using a binocular microscope. The proportion of live, dead eggs / larva present were assessed.5 replicates were conducted per treatment (6) giving a total of 30 tests.

[0123] During the experimental period the temperature ranged from 25.7°C – 27.1°C and relative humidity ranged from 45% - 58%.

[0124] For statistical analysis, percentage mean values and standard error were calculated. A Probit analysis was conducted using ToxRat Professional version 3.3. TheProbit analysis was conducted on the combined ovicidal and nymph mortality results to give a total mortality for the treatment rate. Results

[0125] Results are summarised in Tables 6 and 7, and Figure 4. Spray application of Qcide 540 EW at rates 375 mg ai / L, 750 mg ai / L, 1500 mg ai / L, 2250 mg ai / L and 3000 mg ai / L against TSM eggs resulted in 3.2%, 33.2%, 74.6%, 86.8%, and 91.7% ovicidal mortality at 5-days respectively. Mortality of nymphs from emerged eggs at rates 375 mg ai / L, 750 mg ai / L, 1500 mg ai / L, 2250 mg ai / L and 3000 mg ai / L was observed as 0%, 0%, 7.1%, 11% and 6% respectively at 5-days post spray application. Mortality remained low in water control tests, 2% ovicidal mortality and 1.9% nymph mortality. Exposure of the eggs to tasmanone was believed to have contributed to the nymph mortality.noitacilptpanetmt,ea a ,eciatrciu tr su u hmrep dispdsettdeo ttp os- p o s- w o T wfTof y otilyatitrlao trmo h m p h m.p y)5 mnd = y n n n da,srnlao ag.)dircrege5iv d e =n orad g,atserg n n oatatecrrne s± reecrsp drna en a dp aeen n aaem(Mt.sM no 5 ±s .6itelnelacbaaebilp Tm(a Tpa

[0126] A dosage dependent survival curve was also established for TSM eggs and nymphs, treated with Qcide 540 EW as a direct spray application. The full results of the Probit analysis are given in Table 7. Table 7. Toxicity metrics of Two spotted spider mite eggs and nymphs at 5-days post application, following direct spray of Qcide 540 EW.

Claims

THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS:

1. A method for reducing the viability of an un-emerged pest, comprising exposing the un-emerged pest to an effective amount of a compound of formula (I):(I), wherein: X and Y are each independently selected from oxygen, sulfur and NR4, or one of C=X and C=Y is CH2; A is (C=O)R1, (C=S)R1, OR2, SR2, (CR3NR4R5), C(R3)2OR2, NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2or SO4R2; B is H, C1-C10alkyl, C2-C10alkenyl, aryl or heteroaryl; C, D, E and F are independently selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10trihaloalkyl, C2-C10haloalkoxy, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R1, N=O, N(=O)2, NR4OR2 and SO4R2; R1 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C1-C10haloalkyl, C1-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10 haloalkoxy, C1-C10 hydroxyalkyl, C1-C10 thioalkyl, C1-C10 nitroalkyl, OR2, SR2, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7 and SO4R7; R2is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, (CR3NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2 and NR4OR7; R3 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl, C2-C10 haloalkoxy, OR7, SR7, (CR8NR4R5), NR4R5, (C=NR4)R6, N=O, N(=O)2, NR4OR7 and SO4R7; R4and R5are independently selected from H, C1-C10alkyl, C2-C10arylalkyl, C3- C6cycloalkyl, C2-C10alkenyl, C2-C10heteroarylalkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10 trihaloalkyl, OR7 and SR7;R6 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, C2-C10haloalkoxy, OR7, SR7, (CR8NR9R10), NR9R10, and NR9OR7; R7 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; R8 is selected from H, C1-C10 alkyl, C2-C10 arylalkyl, C3-C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR11, SR11and NR9OR10; R9and R10are independently selected from H, C1-C10alkyl, C2-C10arylalkyl, C3- C6 cycloalkyl, C2-C10 alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl, C2-C10 trihaloalkyl, OR12 and SR12; R11is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl; and R12is selected from H, C1-C10alkyl, C2-C10arylalkyl, C3-C6cycloalkyl, C2-C10alkenyl, C2-C10 heteroarylalkyl, C2-C10 haloalkyl, C2-C10 dihaloalkyl and C2-C10 trihaloalkyl.

2. The method according to claim 1, wherein: X and Y are each independently selected from oxygen and sulfur; A is (C=O)R1, (C=S)R1, (CR3NR4R5), NR4R5, (C=NR4)R1 or NR4OR2; B is H or C1-C10alkyl; C, D, E and F are independently selected from H, C1-C10 alkyl, OR2 and SR2; R1 is selected from H, C1-C10 alkyl, C2-C10 alkenyl, C1-C10 haloalkyl, C1-C10 dihaloalkyl, C2-C10trihaloalkyl, C1-C10hydroxyalkyl, C1-C10thioalkyl and C1-C10nitroalkyl; R2 is selected from H and C1-C10 alkyl; R3is selected from H, C1-C10alkyl, C2-C10alkenyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl; R4 and R5 are independently selected from H, C1-C10 alkyl and OR7; and R7is selected from H and C1-C10alkyl.

3. The method according to claim 1 or 2, wherein: X and Y are each independently selected from oxygen and sulfur; A is (C=O)R1, (C=S)R1, (CR3NR4R5), NR4R5, (C=NR4)R1 or NR4OR2; B is H; C, D, E and F are independently selected from C1-C10alkyl and OR2; R1 is selected from H, C1-C10 alkyl, C1-C10 haloalkyl, C1-C10 dihaloalkyl, C2-C10 trihaloalkyl, C1-C10 hydroxyalkyl, C1-C10 thioalkyl and C1-C10 nitroalkyl; R2is H; R3is selected from C1-C10alkyl, C2-C10haloalkyl, C2-C10dihaloalkyl, C2-C10trihaloalkyl; R4 and R5 are independently selected from C1-C10 alkyl and OR7; and R7is H.

4. The method according to any one of claims 1 to 3, wherein the compound of formula (I) is selected from the group consisting of:.

5. The method of any one of claims 1 to 4, wherein the compound of formula (I) is selected from tasmanone (1-isobutroyl-4 methoxy-3,5,5-trimethylcyclohex-3-en-2,6- dione), agglomerone (1-isobutroyl-4-methoxy-5,5-dimethylcyclohex-3-en-2,6-dione), lateriticone (1-valeroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione), isolateriticone (1-isovaleroyl-4-methoxy-3,5,5-trimethylcyclohex-3-en-2,6-dione) and platyphyllol (6,6-dimethyl-2-acetyl-5-methoxycyclohex-4-ene-1,3-dione).

6. The method according to any one of claims 1 to 5, wherein the compound of formula (I) is tasmanone.

7. The method according to any one of claims 1 to 6, wherein the un-emerged pest is a pest egg.

8. A method for controlling pests, comprising exposing un-emerged pests to an effective amount of a compound of formula (I) as defined in any one of claims 1 to 6.

9. The method according to any one of claim 1 to 8, wherein the compound of formula (I) is provided in a plant extract.

10. The method according to claim 9, wherein the plant extract is a phytochemical extract.

11. The method according to claim 9 or 10, wherein the extract is of a Eucalyptus species plant.

12. The method according to any one of claims 9 to 11, wherein the plant extract comprises the compound of formula (I) in an amount of from about 50 wt% to about 95 wt%.

13. The method according to any one of claims 1 to 12, wherein the pest is selected from the order of the Siphonaptera, from the Hemiptera, from the order of the Phthiraptera, from mites and from ticks.

14. The method according to any one of claims 1 to 13, wherein the pest is selected from the group consiting of Ctenocephalides, Pulex, Cimex, Bemisia, Aleurocanthus, Trialeurodes, Aleyrodes, Pediculus, Tetranychus, Ixodes and Ornithodorus species.

15. The method according to any one of claims 1 to 14, wherein the effective amount of the compound of formula (I) is an amount of from about 50 g / ha (0.005 g / m2) to about 40,000 g / ha (4.0 g / m2) applied to an environment containing the un-emerged pest.

16. The method according to any one of claims 1 to 15, wherein the compound of formula (I) is applied to the environment as a composition containing from about 10 g / L to 400 g / L.

17. The method according to any one of claims 1 to 16, wherein the compound of formula (I) is used in combination with at least one second pesticide.

18. The use of a compound of formula (I) as defined in any one of claims 1 to 6, for reducing the viability of an un-emerged pest or for controlling pests, wherein un-emerged pest(s) are exposed to an effective amount of the compound of formula (I).

19. A kit when used for reducing the viability of an un-emerged pest or for controlling pests, comprising a compound of formula (I) as defined in any one of claims 1 to 6, and optionally another component.

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