Control of resistant pests

Abstract

The present invention relates to a method for controlling pesticide-resistant pests comprising exposing the pesticide-resistant pests to a pesticide-controlling amount of a triketone compound.

Description

[Technical Field]

[0001] The present invention relates to a method for controlling pesticide-resistant pests comprising exposing the pesticide-resistant pests to a pesticide-controlling amount of a triketone compound of formula (I). [Background technology]

[0002] Pesticide resistance is a significant agricultural problem, and the incidence of pesticide resistance is increasing. In the 1940s, farmers in the United States lost about 7% of their crops to pests, and this increased to 13% in the 1980s and 1990s, even though more pesticides were available. It is estimated that up to 1,000 pest species have developed resistance to one or more pesticides since 1945.

[0003] One example is grain protectants, which are pesticides applied to stored grain to prevent damage from pest species such as the mealybug (Rhyzopertha dominica (F.)), rice weevil (Sitophilus oryzae (L.)), red flour beetle (Tribolium castaneum (Herbst)), sawtoothed beetle (Oryzaephilus suranamensis (L.)), and rust beetle (Cryptolestes ferrugineus (Stephens)). Grain protectants have been used for decades, and resistance is now an issue. (Daglish, 2008, J Stored Products Research, 44:71-76). For example, in many states in Australia, the mealybug cannot be controlled with any organophosphates or synthetic pyrethroids, and resistance to the insect growth regulator methoprene is common (Daglish, et al. 2013, J Stored Products Research, 54:71-76). Organophosphate resistance is also common in the sawtooth aphid.

[0004] Pesticide resistance is a major threat to agriculturally useful animals such as cattle. Niyo For example, the cattle tick is a serious pest of cattle throughout the tropics and subtropics of the world. . Visit Raw feeding causes high production losses through weight loss, reduced milk yield and hide damage. Cattle ticks can also transmit tick fever organisms such as Babesia and Anaplasma which can cause high morbidity in susceptible animals.

[0005] Tick ​​control is typically achieved using integrated pest management systems that involve treatment with more than one pesticide. However, to reduce the development of resistance, more options for pesticides are needed, especially those with different modes of action. DISCLOSURE OF THE INVENTION

[0006] The present invention is based, at least in part, on the discovery that flavesone, a potassium channel activator, is effective in controlling pesticide-resistant pests, particularly agriculturally important pests that have developed resistance to commonly used pesticides, such as stored grain pests and cattle ticks and flies.

[0007] Summary of the Invention In one embodiment of the present invention, there is provided a method for controlling pesticide-resistant pests by treating the pesticide-resistant pest with a compound of formula (I).

[0008] [ka] (Wherein, R1 is -C(=O)R7, -OR8, -SR8, -C 1~10 Hydroxyalkyl, -NR9R 10 , —C(═N-R9)R7, —C(═N-OH)R7, —NO, —NO2, —N(OR8)R7, and —OSO3R8; R2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl, and heteroaryl; R3, R4, R5 and R6 are hydrogen, -C 1~10 Alkyl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR8, -SR8, -NR9R 10 , -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C 1~10each independently selected from alkylaryl and —C(═O)R7; R7 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C 1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3 Trihaloalkyl, -OR8, -SR8 and -NR9R 10 Selected from; R8 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or a tautomer thereof.

[0009] In another aspect of the present invention, a method for treating pests in livestock or companion animals is provided. Shopkeeper 1. A method for treating or preventing infection in an animal comprising administering to an animal a compound of formula (I)

[0010] [ka] (Wherein, R1 is -C(=O)R7, -OR8, -SR8, -C 1~10 Hydroxyalkyl, -NR9R 10 , —C(═N-R9)R7, —C(═N-OH)R7, —NO, —NO2, —N(OR8)R7, and —OSO3R8; R2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl, and heteroaryl; R3, R4, R5 and R6 are hydrogen, -C 1~10 Alkyl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR8, -SR8, -NR9R 10 , -(C=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C 1~10 each independently selected from alkylaryl and —C(═O)R7; R7 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C 1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3 Trihaloalkyl, -OR8, -SR8 and -NR9R 10 Selected from; R8 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or a tautomer thereof; harmful plant Shopkeeper Methods are provided wherein the disease is caused by a population of pests, including pesticide-resistant pests.

[0011] In yet another embodiment of the present invention, there is provided a method for controlling pest populations, comprising administering to a subject a compound of formula (I)

[0012] [ka] (Wherein, R1 is -C(=O)R7, -OR8, -SR8, -C 1~10 Hydroxyalkyl, -NR9R 10 , —C(═N-R9)R7, —C(═N-OH)R7, —NO, —NO2, —N(OR8)R7, and —OSO3R8; R2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl, and heteroaryl; R3, R4, R5 and R6 are hydrogen, -C 1~10 Alkyl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR8, -SR8, -NR9R 10 , -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C 1~10 each independently selected from alkylaryl and —C(═O)R7; R7 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3 Trihaloalkyl, -OR8, -SR8 and -NR9R 10 Selected from; R8 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or its tautomers, when pest populations parasitic or infested Also is parasitic or infesting including application to potential environments; Methods are provided wherein the pest population comprises pesticide-resistant pests.

[0013] In a further embodiment of the present invention, the stored plant parts are treated with a pesticide. Parasitic 1. A method for protecting a plant part from a compound of formula (I), comprising:

[0014] [ka] (Wherein, R1 is -C(=O)R7, -OR8, -SR8, -C 1~10 Hydroxyalkyl, -NR9R 10 , —C(═N-R9)R7, —C(═N-OH)R7, —NO, —NO2, —N(OR8)R7, and —OSO3R8; R2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl, and heteroaryl; R3, R4, R5 and R6 are hydrogen, -C 1~10 Alkyl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR8, -SR8, -NR9R 10 , -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C 1~10 each independently selected from alkylaryl and —C(═O)R7; R7 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C 1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3Trihaloalkyl, -OR8, -SR8 and -NR9R 10 Selected from; R8 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or a tautomer thereof, pest Parasitic is caused by populations of pests, including pesticide-resistant pests.

[0015] Detailed Description of the Invention Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which this invention belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, preferred methods and materials are described. For purposes of the present invention, the following terms are defined below.

[0016] The articles "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 a part of speech. By way of example, "an element" means one element or more than one element.

[0017] As used herein, the term "about" refers to an amount, level, value, dimension, size or amount that varies by as much as 30%, 25%, 20%, 15% or 10% from a reference amount, level, value, dimension, size or amount.

[0018] Unless the context requires otherwise by clear words or necessary implication, the word "comprise" or variations such as "comprises" or "comprising" are used in an inclusive sense, i.e., to specify the presence of stated features and not to exclude the presence or addition of further features in various embodiments of the invention.

[0019] Where any prior art publication is referred to herein, it should be understood that such reference does not constitute an acknowledgement that the publication forms part of the common general knowledge in the art in Australia or any other country.

[0020] The term "combination," as used herein, refers to a compound of formula (I) and at least one second pesticide used simultaneously in a single composition or in separate compositions, or sequentially in separate compositions, such that the biological activity of each of the compounds overlaps or manifests simultaneously in the insect.

[0021] The term "control" as used herein means to Noyori raw or spread "Pest control" refers to the control, eradication or destruction of pests, including by preventing the growth and / or development of pests, repelling pests from the environment, increasing pest mortality or inhibiting the growth and / or development of pests, or preventing the reproduction of pests.

[0022] As used herein, the term "environment" refers to an environment in which a compound of formula (I) may be applied to ensure that pesticide-resistant pests are exposed to the compound, or an environment in which a pesticide-resistant pest may be exposed to the compound. Infestation or infestation The term "pesticide-resistant" refers to an environment in which a compound of formula (I) may be applied because of the potential for pesticide resistance. The environment may be an agricultural environment, a domestic environment, an industrial environment, or another environment that is or potentially is a harborage for pesticide-resistant pests. Agricultural environments include those that are resistant to pesticides. Infestation or infestation Examples of agricultural environments include environments for growing commercially important crops, trees, or other plants that may be susceptible to the fungus. Agricultural environments include not only the plants themselves, but also the soil and areas around the plants as they grow, as well as areas where plants or plant parts, such as seeds, grains, leaves, roots, or fruits, may be stored. Agricultural environments may also be environments where commercially important livestock animals are maintained, such as pastures, barns, holding pens, or dairy barns. Domestic environments include environments inhabited by humans or animals, such as companion animals, and may include indoor environments such as carpets, curtains, cupboards, bunks and bedding, animal bedding or blankets, or indoor air. Domestic environments may also include outdoor environments such as home gardens or animal shelters, such as rabbit hutches or kennels. Industrial environments include environments used for industrial purposes, such as the manufacture, storage, or sale of products. Industrial environments include warehouses, manufacturing facilities, stores, storage facilities, and the like, including pet shops, plant nurseries, and grain storage facilities. Other environments may include leisure areas, such as parks, stadiums, exhibition areas, or bodies of water, such as rivers, lakes, ponds, or other places where water collects or may be slowly moving or stagnant.

[0023] As used herein, the term "alkyl" refers to a straight or branched chain saturated hydrocarbon group having from 1 to 10 carbon atoms. Where appropriate, the alkyl group can have a specific number of carbon atoms, including, for example, C, including alkyl groups having 1, 2, 3, 4, 5, or 6 carbon atoms in a linear or branched arrangement. 1~6 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.

[0024] As used herein, the term "alkenyl" refers to a straight-chain or branched hydrocarbon group having from 2 to 10 carbon atoms and one or more double bonds between carbon atoms. Where appropriate, an alkenyl group can have a specific number of carbon atoms. For example, C2-C6, as in "C2-C6 alkenyl," includes 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.

[0025] As used herein, the term "cycloalkyl" refers to a saturated cyclic hydrocarbon. The cycloalkyl ring can contain a specific number of carbon atoms. For example, a 3- to 6-membered cycloalkyl group contains 3, 4, 5, or 6 carbon atoms. Examples of suitable cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0026] As used herein, the term "aryl" is intended to mean any stable monocyclic, bicyclic, or tricyclic carbocyclic ring system of up to seven atoms in each ring, where 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.

[0027] The term "heteroaryl," as used herein, refers to a stable monocyclic, bicyclic, or tricyclic ring of up to seven 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. Heteroaryl groups within this definition 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, oxazoline, benzotriazolyl ... Examples of aryl include aryl, 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.

[0028] The term "haloalkyl," as used herein, refers to an alkyl group in which one or more hydrogen atoms of the alkyl group have been replaced with a halo atom. Where appropriate, the alkyl group can have a specific number of carbon atoms, including, for example, C 1 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 , C 30 , C 31 , C 32 , C 33 , C 34 , C 35 , C 36 , C 37 , C 38 , C 39 , C 40 , C 41 , C 42 , C 43 , C 44 , C 45 , C 46 , C 47 , C 48 , C 49 , C 50 , C 51 , C 52 , C 53 , C 54 , C 55 , C 56 , C 57 , C 58 , C 59 , C 60 , C 61 , C 62 , C 63 , C 64 , C 65 , C 66 , C 67 , C 68 , C 69 , C 70 , C 71 , C 72 , C 73 , C 74 , C 75 , C 76 , C 77 , C 1~6 Examples of haloalkyl groups include 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-dichloroethyl ... propyl, 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 bromoethyl, 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, and 6,6,6-tribromohexyl.

[0029] "Halo," as used herein, refers to fluoro, chloro, bromo, and iodo.

[0030] The terms "hydroxyalkyl," "thioalkyl," and "nitroalkyl" each refer to an alkyl group, as defined above, in which one hydrogen atom has been replaced by a hydroxyl group, a thiol group, or a nitro group, respectively.

[0031] The term "alkoxy," as used herein, refers to an oxygen substituent substituted with an alkyl group, as defined above. Examples of suitable alkoxy groups include, but are not limited to, -OCH, -OCHCH, -O(CH), -OCH(CH), -O(CH), -OCHCH(CH), -OC(CH), -O(CH), -O(CH), -O(CH), and -O(CH).

[0032] Compounds of formula (I) can exist in a number of tautomeric forms. For example, tautomers are shown in the following scheme:

[0033] [ka]

[0034] All such tautomeric structures are intended to be included within the scope of formula (I).

[0035] It is also possible that compounds according to formula (I) can exist in stereoisomeric forms. The compounds may be enantiomers or diastereomers and can exist as individual isomers or in mixtures, including racemic mixtures.

[0036] By "pesticide-resistant pests" is meant pests, such as insects or spiders, that have developed resistance to one or more pesticides previously used to control them. Pesticide-resistant pests can exist in pest populations. For example, the Tiaro strain of the bull tick (R. microplus) has a resistance profile of approximately 30% fluazuron, 60.6% cypermethrin, 57.6% flumetholon, 16.2% amitraz (amidine), 11.3% DDT, 9.3% chlorpyrifos, and 2.4% dieldrin.

[0037] Methods of the Invention In one aspect, the present invention provides a method for controlling pesticide-resistant pests, comprising treating the pesticide-resistant pest with a compound of formula (I):

[0038] [ka] (Wherein, R1 is -C(=O)R7, -OR8, -SR8, -C 1~10 Hydroxyalkyl, -NR9R 10 , —C(═N-R9)R7, —C(═N-OH)R7, —NO, —NO2, —N(OR8)R7, and —OSO3R8; R2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl, and heteroaryl; R3, R4, R5 and R6 are hydrogen, -C 1~10 Alkyl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR8, -SR8, -NR9R 10 , -C(=N-R9)R7, -NO, -NO2, -NR9OR8, -OSO3R8, -C 1~10 each independently selected from alkylaryl and —C(═O)R7; R7 is hydrogen, -C 1~10Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C 1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3 Trihaloalkyl, -OR8, -SR8 and -NR9R 10 Selected from; R8 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or a tautomer thereof.

[0039] In some embodiments, the compound of formula (I) has formula (II):

[0040] [ka] (In the formula, R 11 -CR 12 R 13 R 14 or -NR 15 R 16 Selected from; R 12 and R 13 One of the groups is hydrogen and the other is hydroxyl or -OCR 17 R 18 R 19 or R 12 and R 13 together form an oxo group (=O) or an =N-OH group; R 14 is -CH(CH3)CR 20 R 21 R 22 , -CH2CH(CH3)CR 20 R 21 R 22 or -CH(CH3)CH2CR 20 R 21 R 22 and; R 15 and R 16 is hydrogen and C 1~10 independently selected from alkyl; R 17 , R 18 and R 19 are independently selected from hydrogen or halo; R 20 , R 21 and R 22 is hydrogen, hydroxyl, halo, NO2 and --OCR 17 R 18 R 19 (independently selected from or a tautomer thereof.

[0041] In some embodiments, the compound of formula (I) has formula (III):

[0042] [ka] (In the formula, R 23 and R 24 One of the groups is hydrogen and the other is hydroxyl or -OCR 27 R 28 R 29 or R 23 and R 24 together form an oxo group (=O); R 25 -CR 30 R 31 R 32 , -CH2CR 30 R 31 R 32 or -CH(CH3)CR 30 R 31 R 32 and; R 26 is H or -CH3; where R 26 If is H, then R 25 -CH(CH3)CR 30 R 31 R 32 and; R 27 , R 28 and R 29 are independently selected from hydrogen or halo; R 30 , R 31 and R 32 are independently selected from hydrogen, hydroxyl, halo, NO2 and -OCR5R6R7 or a tautomer thereof.

[0043] In some embodiments, the compound of formula (I) is:

[0044] [ka]

[0045] [ka]

[0046] [ka] or a tautomer thereof.

[0047] In certain embodiments, the compound of formula (I) is flavesone (1-isobutyroyl-3,3,5,5-tetramethylcyclohexane-2,4,6-trione):

[0048] [ka] Leptospermone (1-valeroyl-3,3,5,5-tetramethylcyclohexane-2,4,6-trione):

[0049] [ka] or isoleptospermone (1-isovaleroyl-3,3,5,5-tetramethylcyclohexane-2,4,6-trione):

[0050] [ka] In particular, it is selected from the flavesones.

[0051] The compounds of formula (I) can be isolated from oil-producing trees, for example trees from the Myrtaceae family, such as Leptospermum scoparium or Eucalyptus grandis or Eucalyptus cloeziana, in particular Leptospermum scoparium.

[0052] In other embodiments, compounds of formula (I) can be prepared synthetically, for example, as described in WO 2002 / 089587. In one method, 1,3,5-trihydroxybenzene can be prepared according to Scheme 1:

[0053] [ka] It can be reacted with RCN in the presence of zinc chloride as shown in (Blatt, Org. Synth. Col 11, 1943, 522-523).

[0054] Anhydrous methyl iodide (6 equivalents) is added slowly to 1-acyl-2,4,6-trihydroxybenzene (1 equivalent) and sodium ethoxide (6 equivalents) in anhydrous methanol to give 1-acyl-3,3,5,5-tetramethyl-2,4,6-cyclohexatrione, as shown in Scheme 2 (U.S. Pat. No. 4,202,840).

[0055] [ka]

[0056] The effective amount of the compound of formula (I) depends on whether the compound is applied to the pest itself, or to the environment, or to livestock or companion animals or plant parts, and also depends on the identity of the pesticide-resistant pest.Typically, the effective amount is within the range of 0.1 ppm to about 500,000 ppm, particularly 1 ppm to 200,000 ppm or 1 ppm to 100,000 ppm.In some embodiments in which the pest is directly exposed to the compound of formula (I), the effective amount can be in the range of 10 ppm to 10,000 ppm, or 100 ppm to 10,000 ppm, or 100 ppm to 5000 ppm, particularly 300 ppm to 5000 ppm, or 500 ppm to 5000 ppm, more particularly 800 ppm to 2,500 ppm, or 900 ppm to 2,000 ppm. In some embodiments, an effective amount may be between 100 ppm and 1000 ppm, e.g., 200 ppm and 800 ppm, or 300 ppm and 600 ppm. In other embodiments, an effective amount may be between 600 ppm and 5000 ppm, particularly between 1000 ppm and 2500 ppm. In some embodiments, an effective amount is between 20 ppm and 100 ppm, particularly between 25 ppm and 80 ppm. Effective amounts applied to environments such as grain in grain silos may range from 20 ppm to 100 ppm, particularly 50 ppm to 100 ppm.

[0057] In some embodiments, the pest is an insect that is resistant to one or more insecticides. In other embodiments, the pest is a spider that is resistant to one or more arachnids. In some embodiments, the pest is an insect population that includes insects that are resistant to one or more insecticides, or a spider population that includes spiders that are resistant to one or more arachnids.

[0058] Insects or populations of insects that include insects that are resistant to one or more insecticides include insects such as: (a) From the order of Lepidoptera (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, rice leaf borer (Cnaphalocrocis medinalis), woolly corn moth (Crocidolomia binotalis), codling moth (Cydia pomonella), Dendrolimus pini, American cucumber moth (Diaphania nitidalis), Southwestern corn borer (Diatraea grandiosella), Missing ear moth (Earias insulana), Corn moth (Elasmopalpus lignosellus), Grape leaf moth (Eupoecilia ambiguella), Feltia subterranea, Grapholitha funebrana, Japanese pear fruit moth (Grapholitha molesta), Heliocoverpa armigera, Heliocoverpa virescens virescens, Heliocoverpa zea, Hellula undalis, Hibernia defoliaria, Hypliantriacunea, 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, Pine borer moth, Pectinophora gossypiella, Tobacco leafminer, Phthorimaea operculella, Citrus leafminer, Pieris brassicae, Green cloverworm, Plathypena scabra, Platynota stultana, Diamondback moth, Plutella xylostella, Prays citri, Prays oleae, Prodenia sunia, Prodenia ornithogalli, Pseudoplusia includens, Rhyacionia flustranafrustrana, 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, as well as Galleria mellonella, Sitotroga cerealella, Ephestia cautella and Tineola bisselliella; (b) From the order of the beetles (Coleoptera), for example, 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, Colorado potato beetle (Leptinotarsa ​​decemlineata), Limonius californicus, rice water weevil (Lissorhoptrus oryzophilus), MelanotusMelanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorhynchus sulcatus, Otiorhynchus ovatus, Phaedon cochleariae, Phyllopertha horticola, Phyllophaga species, Phyllotreta chrysocephala, Phyllotreta nemorum nemorum, Phyllotreta striolata, Japanese beetle (Popillia japonica), Psylliodes napi, Scolytus intricatus and Sitona lineatus, as well as Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Sitophilus granarius, Lasioderma serricorne, Oryzaephilus surinamensis, Rhyzopertha dominica, Rice weevil (Sitophilus oryzae), red flour beetle (Tribolium castaneum), small red beetle (Trogoderma granarium) and Brazilian bean weevil (Zabrotes subfasciatus); (c) From the order of the Diptera (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 trifoliata, trifolii, Mayetiola destructor, Orseolia oryzae, Oscinella frit, Pegomya hyoscyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi and Rhagoletis pomonella, as well as Aedes aegypti, Aedes vexans, Aedes albopictus, Anopheles maculipennis, Chrysomya bezziana), Cochliomyia hominivorax, Chrysomya macellaria, Cordylobia anthropophaga, Culex pipiens, Fannia canicularis, Gasterophilus intestinalis, Glossina molsitansmorsitans, horn fly (Haematobia irritans), Haplodiplosis equestris, Hypoderma lineata, sheep blowfly (Lucilia cuprina), broad-legged blowfly (Lucilia sericata), house fly (Musca domestica), big house fly (Muscina stabulans), sheep fly (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, Heliothirips haemorrhoidalis, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci; (e) From the order of the Hymenoptera (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 licteri, richteri) and the Japanese ant (Technomyrmex albipes); (f) From the order of Heteroptera (suborder Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus ictericus, Leptoglossus phyllopus, Lygus hesperus, Lygus lineolaris, Lygus platensis pratensis, Mormidea pictiventris, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor;(g) From the order of the Homoptera (suborder 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, radish aphid (Brevicoryne brassicae), Dalbulus maidis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Empoasca fabae, Eriosorna lanigerum, small brown planthopper (Laodelphax striatella), Macrosiphum avenae, Macrosiphun euphorbiae, Macrosiphon rosae, Megoura visiae viciae, Metopolophium dirhodum, Myzus persicae, Myzus cerasi, Nephotettix cincticeps, Nilaparvata lugens, Perkinsiella saccharicida, Phorodon humuli, Psyllamali), Psylla pyri, Pear psylla (Psylla pyricola), Corn aphid (Rhopalosiphum maidis), Green wheat aphid (Schizaphis graminum), Long-horned wheat aphid (Sitobion avenae), White-backed planthopper (Sogatella furcifera), Citrus aphid (Toxoptera citricida), White-winged whitefly (Trialeurodes abutilonea), Greenhouse whitefly (Trialeurodes vaporariorum) and Viteus vitifoliae; (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 Orthoptera (Orthoptera), for example, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca peregrina peregrina, Stauronotus maroccanus and Schistocerca gregaria, as well as the European house cricket (Acheta domesticus), the Asian cockroach (Blatta orientalis), the German cockroach (Blattella germanica) and the American cockroach (Periplaneta americana); (j) from the order of the lice (Phthiraptera), for example, the order Mallophaga, for example, the genus Damalina, and the suborder Anoplura, for example, the genera Linognathus and Haematopinus; (k) From the order of the Hemnipterans (Hemiptera), for example, the genera Aphis, Bennisia, Phorodon, Aeneolamia, Empoasca, Perkinsiella, Pyrilla, Aonidiella, Coccus, Pseudococcus, Helopeltis. , Lygus, Dysdercus, Oxycarenus, Nezara, Aleyrodes, Triatoma, Psylla, Myzus, Megoura, Phylloxera, Adelges, Nilaparvata, Nephotettix or Cimex; (l) From the order of the fleas (Siphonaptera), for example, the genus Ctenocephalides or Pulex; (m) From the order Thysanura, e.g., Lepisina; (n) From the order of earwigs (Dermaptera), e.g., the genus Forficula; and (o) From the order of the psocots (Psocoptera), for example, the genus Peripsocus.

[0059] The insect may be resistant to one or more insecticides that are commonly used to control the insect before resistance developed. For example, the insect may be resistant to one or more insecticides selected from the following: (i) Sodium channel modulators, such as pyrethroids, DDT, and methoxychlor. Suitable pyrethroids include acrinathrin, allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, γ-cyhalothrin, λ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin, deltamethrin, dimefluthrin, empenthrin, esfenvalerate, and the like. Late, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate, tau-fluvalinate, halfenprox, imiprothrin, metofluthrin, permethrin, fenothrin, prallethrin, profluthrin, pyrethrins (pyrethrum), resmethrin, RU15525, silafluofen, tefluthrin, tetramethrin, tralomethrin, transfluthrin, and ZX18901. (ii) Acetylcholinesterase (AChE) inhibitors, such as carbamates or organophosphates. Suitable carbamates include alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxar, thiodicarb, thiofanox, triazameate, trimethacarb, and xylylcarb. Suitable organic phosphates include acephate, azamethiphos, azinphos, azinphos-methyl, azinphos-ethyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, disulfoton, ethion, ethoprophos, fenflur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, isofenphos, isoxathion, mafenphos, methylvin ... These include rathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos, pirimiphos-methyl, profenphos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion. (iii) GABA-gated chloride channel antagonists, such as organic chlorides or fiprol. Suitable organic chlorides include chlordane, endosulfan, and α-enosulfan. Suitable fiprols include ethiprole, fipronil, pyrafluprole, and pyriprole. (iv) Nicotinic acetylcholine receptor agonists, such as nicotine or chloronicotinyl compounds. Suitable chloronicotinyl compounds include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiocloprid, and thiamethoxam. (v) allosteric acetylcholine receptor modulators, such as spinetoram or spinosad. (vi) Chloride channel actuators, such as abamectin, emamectin benzoate, lepimectin, or milbemectin. (vii) a juvenile hormone mimetic selected from hydroprene, kinoprene, methoprene, S-methoprene, fenoxycarb, or pyriproxyfen. (viii) Homoptera antifeedants, such as pymetrozine or flanicamid. (ix) Mitochondrial ATP synthase inhibitors, such as diafenthiuron or tetradifan. (x) Uncouplers of oxidative phosphorylation, such as chlorfenapyr or DNOC. (xi) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam or thiosultap-sodium. (xii) Inhibitors of chitin biosynthesis, such as benzoylureas or buprofezin. Suitable benzoylureas include bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, or triflumuron. (xiii) Molting disruptors, such as cyromazine. (xiv) Ecdysone receptor agonists or disruptors, such as diacylhydrazines. Suitable diacylhydrazines include chromafenozide, halofenozide, methoxyfenozide, or tebufenozide. (xv) Octopamine receptor agonists, such as amitraz. (xvi) Mitochondrial complex I electron transport inhibitors, such as hydramethylnon, acequinocyl, and fluacrypryrim. (xvii) Acetyl-CoA carboxylase inhibitors, such as tetronic acid derivatives or tetramic acid derivatives. Suitable tetronic acid derivatives include spirodiclofen and spiromesfen, and a suitable tetramic acid derivative is spirotetramat. (xviii) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone. (xix) Mitochondrial complex IV electron inhibitors, such as phosphines or cyanides. Suitable phosphines include zinc phosphide, aluminum phosphide, calcium phosphide, or phosphine. (xx) Mitochondrial complex IV electron transport inhibitors, such as cyenopyrafen. (xxi) Ryanodine receptor modulators, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[0060] The spider group includes spiders, harvestmen, scorpions, crabs, microscopions, mites and ticks, especially mites and ticks (order Acarina). Suitable spiders include: (i) Mites, such as Aculops lycopersicae, Aculops pelekassi, Aculus Schlechtendali, Balustium medicagoense, Brevipalpus phoenicis, Brevipalpus californicus, Bryobia praetiosa, Bryobia rubrioculus, Bryobia species, such as clover mites, Dermanyssus gallinae, Eotetranychus carpini, Eotetranichus lewisi, Eutetranychus banksia banksia, Eutetranychus orientalis, Eriophyes sheldoni, Eriophyes tiliae, Eriophyes inangulis, Eriophyes vitis, Halotydeus destructor (red-legged earth mite), Oligonychus pratensis, Oligonychus coffeae, Oligonychus oryzae, Oligonychus milleri, Panonychus ulmi, Panonychus citri citri, Penthaleus, such as blue oat mite, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Sarcoptesscabiei, Tarsonemus pallidus, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus and Tetranychus urticae. (ii) 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, megnini, Rhipicephalus apendiculatus, Rhipicephalus evertsi and Rhipicephalus microplus.

[0061] Spiders may be resistant to one or more arachnicides commonly used to control spiders, particularly mites or ticks, before resistance develops. For example, spiders may be resistant to abamectin, acequinocyl, acrinathrin, aldicarb, alpha-cypermethrin, amidithione, amiton, amitraz, alamite, arsenic trioxide, azinphos-ethyl, azinphos-methyl, azobenzene, azocyclotine, azotoate, benomyl, benzoximate, benzyl benzoate, bifenazate, bifenthrin, binapacryl, bromocyclen, bromophos, bromophos-ethyl, bromopropylate, butocarboxim, camphechlor, carbanolate, carbapenem, carbazinol ... methylpropanol, carbofuran, carbophenothion, carvacrol, chinomethionate, chlorbenesid, chlordimeform, chlorfenapyr, chlorphenetole, chlorfenson, chlorphenesulfide, chlorfenvinphos, chlorobenzilate, chlormebuform, chloromethiron, chloropropylate, chlorpyrifos, chlorthiophos, clofentezine, closantel, coumaphos, crotamiton, crotoxyphos, cyanthoate, cyclopropanol, cyenopyrafren ), cyflumetofen, cyhalothrin, cyhexatin, cypermethrin, cyromazine, DDT, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, diafenthiuron, dialifos, diazinon, dichlofluanid, dichlorvos, dicofol, dieldrin, dienochlor, diflobidazine, dimefox, dimethoate, ginex, dinobuton, dinocap, dinocton, dinopenton, dinosulfone, dinotervon, dioxathion, diphenylsulfon Fen, disulfoton, DNOC, endosulfan, endothion, ethion, etheoate-methyl, etoxazole, fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpropathrin, fenpyroximate, fenthone, fentrifanil, fenvalerate, fipronil, fluacrypyrim, fluazuron, flubenzimine, flucycloxuron, flucythrinate, fluenethyl, flufenoxuron, flumethrin, fluorbenside, fluvalinate, formetanate,Formothion, formoparanate, genita (genit), halfenprox, heptenophos, hexachlorophene, hexythiazox, isocarbophos, lindane, malathion, mecarbam, methacrifos, methamidophos, methiocarb, metolcarb, mevinphos, milbemectin, mipafox, monocrotophos, naled, nifluridide, omethoate, oxamyl, oxydeprophos, oxydisulfoton, parathion, permethrin, fencapton, phorate, phosalone, phosmet, phoxim, pirimiphos-methyl, propargite, The insecticides may be resistant to one or more arachnicides or acaricides selected from propetamphos, propoxar, protidathion, prothoate, pyridaben, pyrimidifen, quinalphos, quinthiofos, sucladan, sofamid, spirodiclofen, sulfluramide, sulfotep, sulfur, tau-fluvalinate, tebufenpyrad, TEPP, tetrachlorvinphos, tetradifon, tetrasulf, thiocarboxim, thiofanox, thiometon, thioquinox, thuringiensin, triatene, triazophos, trichlorfon, and vamidothion.

[0062] The pest may be in any part of its life cycle, for example, egg, larva, pupa, adult or nymph, hi some embodiments, the pest may be in the larval form.

[0063] In a particular embodiment, the pest is a tick or mite, particularly a tick or mite in its larval form, particularly a bovine tick in its larval form.

[0064] In some embodiments, the methods of the present invention are directed to the prevention and treatment of pests in livestock or companion animals. parasitism A method for treating or preventing a pest, comprising: parasitism is a method for combating pest populations, including pesticide-resistant pests, which method involves applying a compound of formula (I) as defined above to livestock or companion animals.

[0065] In some embodiments, the livestock animal is selected from cows, sheep, goats, deer, pigs, camels, llamas, alpacas, chickens, etc. In other embodiments, the companion animal is selected from dogs, cats, rabbits, guinea pigs, hamsters, mice, horses, etc.

[0066] In some embodiments, the compound of formula (I) can be applied topically, for example, by dipping, spraying, pouring on, washing, fogging or misting, irrigating, or applying drops. In other embodiments, the compound of formula (I) is applied systemically, for example, in a tablet, capsule, chewable tablet, or liquid irrigation formulation.

[0067] In some embodiments, the method comprises: Infestation or infestation pesticide-resistant pests in the environment caused by populations of pests, including pesticide-resistant pests Infestation or infestation or potential pests Infestation or infestation The method comprises administering a compound of formula (I) as defined above to a pest Infestation or infestation Inhabitants or pests Infestation or infestation This involves application to an environment where there is a risk of the pest harboring the pest. Infestation or infestation The environment may be any environment in which the subject may reside, for example, an agricultural environment, a domestic environment, an industrial environment or a leisure environment. In certain embodiments, the environment is an agricultural environment.

[0068] In some embodiments, the method comprises storing the plant product. Niyo The method is used to control pests that infest the plant product, which method involves contacting the plant product with a compound of formula (I).

[0069] Suitably, the plant parts to be protected are contacted by dipping, spraying, fogging or misting. Contacting can be achieved before or during storage, especially before storage.

[0070] In some embodiments, plant part is the grain that will be stored in silo before use.This method can be particularly useful for controlling the pests that damage grain in storage, where the population of pests comprises the population of Rhyzopertha dominica, rice weevil (Sitophilus oryzae), red flour beetle (Tribolium castaneum), saw-toothed flatworm (Oryzaephilus surinamensis) or rust beetle (Cryptolestes ferrugineous), including pesticide-resistant pests, such as organophosphates (e.g., fenitrothion, malathion, chlorpyrifos-methyl and pirimiphos-methyl); and / or synthetic pyrethroids (e.g., deltamethrin or bioresmethrin); and / or insect growth regulators (e.g., methoprene).

[0071] In some embodiments, the method comprises: Niyo The compound of formula (I) is used to control pests that grow on and cause damage to cereal crops, particularly cereal crops such as rice, wheat, durum wheat, corn, maize, barley, millet, sorghum, oats, rye, triticale, teff, fenio, wild rice, and spelt. The method involves contacting the pest with a compound of formula (I) in an agricultural environment. The contacting can be carried out by applying the compound or a composition containing the compound of formula (I) to the crop and / or the soil surrounding the crop, wherein the crop is protected from the pest. Niyo populations of pests, especially pesticide-resistant pests NiyoExamples of pesticide-resistant pests include populations of H. destructor (red-legged earth mite), Balustium medicagoense, Penthaleus species such as the blue oat mite, and Bryobia species such as clover mite that are resistant to organophosphates such as chlorpyrifos and / or pyrethroids such as bifenthrin.

[0072] In some embodiments, the compound of formula (I) can be applied solvent-free, while in certain embodiments, the compound of formula (I) is applied in the form of a composition together with an acceptable carrier, diluent and / or excipient, which also applies to the exposure of pests to the compound of formula (I).

[0073] The composition can be formulated into any suitable composition, such as spray, aerosol, oil, emulsifiable concentrate, wettable powder, flowable formulation, granulated formulation, powder, dust, solution, suspension, emulsion or controlled release formulation, tablet, capsule, oral liquid, shampoo, conditioner, spot-on formulation, drench or dip.The composition can be formulated with solid or liquid carrier where appropriate.The choice of formulation and application mode depend on the pest to be controlled, the environment to be controlled, or the animal that is plagued by the pest, and the appropriate choice is made taking into account the pest, the target and the environment.

[0074] In some embodiments, the formulation may contain natural additives such as antioxidants and stabilizers. For example, antioxidants may include α-tocopherol, and suitable stabilizers may include gum arabic, guar gum, locust bean gum, xanthan gum, kelgum, polyvinyl alcohol, sodium caseinate, and mixtures thereof.

[0075] Examples of solid carriers useful in preparing formulations are clays, including kaolin clay, diatomaceous earth, hydrous synthetic silicon oxide, bentonite, fubasami clay, and acid clay; talc; ceramics; inorganic minerals, such as Celite™, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica; these solid carriers may be finely divided or granular. Examples of useful liquid carriers include water, alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene, aliphatic hydrocarbons such as hexane, cyclohexane, kerosene and diesel, esters such as ethyl acetate and butyl acetate, nitriles such as acetonitrile and isobutyronitrile, ethers such as diisopropyl ether and dioxane, acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide, halogenated hydrocarbons such as dichloromethane, trichloroethane and carbon tetrachloride, dimethyl sulfoxide, and fish oil, mineral oil, plant-derived oils such as olive oil, rapeseed oil, cottonseed oil, soybean oil and sesame oil, as well as essential oils such as lavender oil, eucalyptus oil, tea tree oil, citrus oil, etc. Solid or liquid carriers can be used alone or in combination. Examples of gas carriers, propellants, are butane gas, isobutene, pentane, LPG (liquefied petroleum gas), dimethyl ether, fluorocarbons and carbon dioxide gas.

[0076] Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers and their polyoxyethylene adducts, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives, sorbitan monolaurate, alkylarylsorbitan monolaurate, alkylbenzenesulfonates, alkylnaphthalenesulfonates, ligninsulfonates, and sulfate salts of higher alcohols. These surfactants can be used alone or in combination.

[0077] Examples of adjuvants for formulations, such as binders and dispersants, include casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives and alginic acid, lignin derivatives, bentonite, sugars, and water-soluble synthetic polymers such as polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acid. Examples of stabilizers include PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), synergists such as piperonyl butoxide, vegetable oils, mineral oils, fish oils, surfactants, and fatty acids or their esters.

[0078] The emulsifier that can be used is suitably one or more selected from nonionic or anionic emulsifiers. Examples of nonionic emulsifiers include, but are not limited to, polyoxyethylene alkyl phenyl ethers, polyoxyethylene alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, and polyoxyethylene polyoxypropylene alkyl ethers. Examples of anionic emulsifiers include alkyl sulfates, polyoxyethylene alkyl ether sulfates, sulfosuccinates, taurine derivatives, sarcosine derivatives, phosphate esters, alkylbenzene sulfonates, etc. A mixture of polyoxyethylene styryl phenyl ether and calcium allylbenzene sulfonate is preferred. These emulsifiers can be used in an amount of 1 to 20 parts by weight per 100 parts by weight of the composition of the present invention.

[0079] In some embodiments, the compound of formula (I) is formulated as a spray.The spray can be formulated as a liquid for use in an atomizer or aerosol.In some embodiments, the liquid solubilizes the compound of formula (I), for example, where the liquid or solvent is oil or hydrocarbon solvent.In other embodiments, the liquid is an aqueous liquid, and the formulation is in the form of a suspension or emulsion.

[0080] In some embodiments, the composition can include a propellant, such as butane, isobutene, pentane, carbon dioxide, or nitrogen.

[0081] In some embodiments, the spray can be placed topically in the environment or on the animal, or can be applied directly to the resistant pest. In other embodiments, the compound of formula (I) is impregnated into a carrier, such as filter paper or fabric, and applied to the pest for contact with the pest. Shopkeeper It can be formulated in a viscous preparation that is left at the site of injury. In some embodiments, the compound of formula (I) can be formulated in a slow release preparation.

[0082] The method of the present invention can be deployed as part of an integrated pest management system, wherein the compound of formula (I) is used in combination with other pesticides, either simultaneously or sequentially. The compound of formula (I) is a potassium channel activator. In some embodiments, the compound of formula (I) has a different action. mechanism In certain embodiments, the pesticide-resistant pest is not resistant to the effects of any of the compounds used in the combination. In some embodiments, the combination of the compound of formula (I) and the second pesticide is in a single composition. In other embodiments, the compound of formula (I) and the second pesticide are in separate compositions. The second pesticide is a compound of formula (I) or a pesticide-resistant pest. 0059 , i) to xxi) or paragraphs 0061 It can be selected from any of those listed in

[0083] In order that the invention may be readily understood and put into practice, certain preferred embodiments are described by way of the following non-limiting examples. [Brief explanation of the drawings]

[0084] [Figure 1] FIG. 1 shows a graph of a dose response curve for a susceptible population of H. destructor when exposed to flavesone at concentrations of 0 mg, 3 mg, 10 mg, 30 mg, 100 mg, 300 mg, 1000 mg, 3000 mg and 10000 mg ai / L (ppm) for 4 hours, 6 hours, 8 hours and 24 hours. [Figure 2] FIG. 1 shows a graph of dose response curves for sensitive and resistant populations of H. destructor when exposed to flavesone at concentrations of 0 mg, 3 mg, 10 mg, 30 mg, 100 mg, 300 mg, 1000 mg, 3000 mg and 10000 mg ai / L (ppm) for 24 hours. [Figure 3] FIG. 1 shows a graph of dose response curves for susceptible and resistant populations of H. destructor when exposed to bifenthrin concentrations of 0 mg, 0.00001 mg, 0.0001 mg, 0.001 mg, 0.01 mg, 0.1 mg, 1.0 mg, 10 mg, 100 mg, 1000 mg, and 10000 mg ai / L (ppm) for 24 hours. [Figure 4] FIG. 1 is a graph of dose response curves for susceptible and resistant populations of H. destructor when exposed to chlorpyrifos concentrations of 0 mg, 0.7 mg, 7.0 mg, 70 mg, and 700 mg ai / L (ppm) for 24 hours. [Figure 5]FIG. 1 shows a graph of dose response curves for susceptible and resistant populations of green peach aphid exposed to flavesone at concentrations of 0 mg, 10 mg, 100 mg, 300 mg, 1000 mg, 2000 mg, 5000 mg, 10000 mg, 30000 mg and 100000 mg ai / L and for 48 hours of exposure. [Figure 6] FIG. 1 shows a graph of dose response curves for susceptible and resistant populations of green peach aphid exposed to flavesone at concentrations of 0 mg, 10 mg, 100 mg, 300 mg, 1000 mg, 2000 mg, 5000 mg, 10000 mg, 30000 mg and 100000 mg ai / L and 96 hours of exposure. [Figure 7] FIG. 1 shows a graph of dose response curves for susceptible and resistant populations of green peach aphid exposed to pirimicarb at concentrations of 0.025 mg, 0.25 mg, 2.50 mg, 25.0 mg, 250.0 mg, and 2500.0 mg ai / L and 48 hours of exposure. [Figure 8] FIG. 1 shows a graph of dose response curves for susceptible and resistant populations of green peach aphid exposed to pirimicarb at concentrations of 0.025 mg, 0.25 mg, 2.50 mg, 25.0 mg, 250.0 mg, and 2500.0 mg ai / L and 96 hours of exposure. [Example]

[0085] [Example 1] Larval Packet Test - Bovine Tick The larval packet test (LPT) is a modification of that originally described by Stone and Haydock (1962, Bull. Entomol. Res., 563-578, http: / / dx.doi.org / 10.1017 / S000748530004832X) for the assessment of field resistance in cattle tick (Rhipicephalus microplus) larvae.

[0086] The first LPT assay was performed to identify the potential range of flavesone acaricidal activity against larvae of a susceptible non-resistant field strain (NRFS) of R. microplus as a reference strain, using a wide range of concentrations (ten-fold series).

[0087] The test compound, flavesone, 6-isobutyryl-2,2,4,4-tetramethylcyclohexane-1,3,5-trione, 96.7%, was used. Because its volatility / evaporation properties were unknown, the LPT method was modified to incorporate the use of appropriately sized polyethylene plastic sheets to encase the larval packets, minimizing exposure of the active test article to the atmosphere.

[0088] Additionally, the use of the solvent trichloroethylene (TCE) was eliminated, avoiding the time required for evaporation in the preparation of the test strips. Evaporation was minimized by preparing the test solution in olive oil alone as the diluent, and immediately wrapping the strip in a plastic sheet and sealing it with a bulldog clip.

[0089] A stock solution with a concentration of 100,000 ppm (10%) flavesone was prepared in olive oil as the dilution medium (1.035 mL of flavesone (96.7%) to 8.965 mL of olive oil) and then further diluted in a 1:10 series to obtain concentrations of 10,000 ppm, 1,000 ppm, 100 ppm, 10 ppm, and 1 ppm. The negative control was olive oil only. No positive control was included in this experiment. Due to the viscosity of olive oil, all solutions were prepared using the reverse pipette technique.

[0090] Filter paper (75 mm x 85 mm Whatman® 541) was impregnated in a grid pattern with 225 μL of each solution using a micropipette onto one half of the paper, which was immediately folded in half, wrapped in polyethylene plastic, and sealed with three bulldog clips. The impregnated paper was kept at room temperature on an aluminum tray for a minimum of 60 minutes to allow for dispersion across the grid pattern of the paper before aliquoting the larvae. Packets were prepared in duplicate for each concentration, including a negative control.

[0091] An 8-dram vial containing approximately 20,000 hatched 7- to 21-day-old NRFS larvae (approximately 1 g of eggs) was opened and placed on a moated tray containing a small amount of detergent water approximately 15 to 30 minutes before use. Only larvae that migrated to the top of the vial were used in the assay.

[0092] Using plastic disposable forceps, an aliquot of approximately 100 larvae was placed into each packet, and the packets were resealed and incubated at 27°C and 85% relative humidity (RH).

[0093] After 24 hours, the larval packets were opened and the number of dead and live larvae was counted under a magnifying lamp. Percent mortality was calculated and, where applicable, calculated using Abbott's formula (Abbott, 1925, J. Economic Entomology, 18:256-257):

[0094]

number

[0095] LC 50 Value and LC 99 Values ​​were determined by probit mortality versus log concentration analysis. Probit values ​​were derived from "Transformation of Percentages to Probit's Tables" published by Fisher RA and Yates F. (1938).

[0096] The results are shown in Tables 1 and 2.

[0097] [Table 1]

[0098] LC 50 Value and LC 99 The values ​​were determined and are shown in Table 2.

[0099] [Table 2]

[0100] [Example 2] LPT assay using resistant larvae The LPT assay of Example 1 was repeated using a narrower range of flavesone concentrations, a half-series, to determine the LC for susceptible NRFS and the multiresistant tiaro reference strain. 50 Value and LC 99 value was determined.

[0101] The Tiaro strain of R. microplus contains approximately 30% resistance to fluazuron, 60.6% to cypermethrin (SP), 57.6% to flumethrin (SP), 16.2% to amitraz (amidine), 11.3% to DDT, 9.3% to chlorpyrifos (OP) and 2.4% to dieldrin [2014 Acaricide Resistance Profiling].

[0102] The synthetic pyrethroid (SP) cypermethrin was included in the assay as a positive control.

[0103] A stock solution of flavesone (100,000 ppm) was diluted 1 in 10 with olive oil (1 mL to 9 mL dilution) to give 10,000 ppm, which was then further diluted in a 2 in 1 series (5 mL to 5 mL dilution) to give concentrations of 5,000 ppm, 2,500 ppm, 1,250 ppm, 625 ppm, 312.5 ppm, and 156.25 ppm.

[0104] For preparation of the positive control, cypermethrin, a stock solution at a concentration of 10,000 ppm was prepared in 2:1 trichloroethylene (TCE) / olive oil as solvent (0.0352 g cypermethrin, 94.8% purity, to 10 mL solvent) and then further diluted in a 1 / 2 series (5 mL to 5 mL solvent) to obtain concentrations of 5,000 ppm, 2,500 ppm, 1,250 ppm, 625 ppm, 312.5 ppm, and 156.25 ppm.

[0105] Flaveson paper was prepared as in Example 1.

[0106] Using a micropipette, cypermethrin paper was impregnated with 670 μL of each solution and allowed to dry (TCE evaporation) for a minimum of 60 minutes by hanging it on a rack in a fume hood. The paper was then folded in half, sealed with three bulldog clips, and placed on an aluminum tray before aliquoting the larvae. All packets were prepared in duplicate.

[0107] Negative control papers were prepared for both flavesone (olive oil only) and the positive control, cypermethrin (2:1 TCE / olive oil).

[0108] Mortality was assessed at 24 hours and LC 50 Value and LC 99 Values ​​were determined by probit mortality versus log concentration analysis. Dose-response relationships were determined for 24-hour contact exposures. Results are shown in Table 3.

[0109] [Table 3]

[0110] At 1,250 ppm flavesone for both strains, some larvae still waved their legs in the air; however, they took no steps (flaccid paralysis), which indicates survival. At 2,500 ppm flavesone for both strains, no movement was observed and 100% mortality was observed.

[0111] LC between NRFS and Tiaro strains 50 Data and LC 99 When the data were compared, there was no evidence of cross-resistance to flavesone.

[0112] Negative control mortality ranged from 0% to 0.51% and was corrected using the Abbott formula where applicable.

[0113] Using probit mortality versus log concentration analysis, LC 50 Value and LC 99 The values ​​were determined and are shown in Table 4.

[0114] [Table 4]

[0115] [Example 3] The experiment in Example 2 was repeated for the NRFS strain only, with a 1:2 serial dilution and cypermethrin as a positive control. The concentrations of flavesone were 5,000 ppm, 2,500 ppm, 1,250 ppm, 625 ppm, and 312.5 ppm. The concentrations of cypermethrin were 1,250 ppm, 652 ppm, 312.5 ppm, 156.25 ppm, 78.125 ppm, and 36.0625 ppm.

[0116] Mortality was assessed at 24 hours and LC 50 Value and LC 99 Values ​​were determined by probit mortality versus log concentration analysis.

[0117] At 1,250 ppm flavesone, as in Example 2, some larvae still waved their legs in the air; however, they took no steps (flaccid paralysis), which indicates survival. At 2,500 ppm flavesone, no movement was observed and 100% mortality was observed.

[0118] Negative control mortality ranged between 0% and 1.02% and was corrected using the Abbott formula, where applicable.

[0119] The results are shown in Table 5:

[0120] [Table 5]

[0121] LC 50 Value and LC 99 The values ​​are shown in Table 6:

[0122] [Table 6]

[0123] [Example 4] In Examples 2 and 3, 100% mortality was recorded after 24 hours of contact exposure at a flavesone concentration of 1,250 ppm, but it was noted that at this concentration for both the NRFS and Tiaro strains, some larvae were still waving their legs in the air but were not taking steps indicating survival (flaccid paralysis) and were therefore moribund. This experiment was conducted to determine whether these larvae would die within a further 24 hours of contact exposure and whether mortality could be determined at 48 hours.

[0124] The concentrations of 1,250 ppm, 625 ppm, and 312.5 ppm flavesone prepared for Example 3 were used on the same day they were prepared. Duplicate papers were prepared for both the NRFS and Tiaro strains (including a negative control) as described in Example 2.

[0125] Mortality was assessed at 48 hours and LC 50 Value and LC 99 Values ​​were determined by probit mortality versus log concentration analysis. The results are shown in Tables 7 and 8.

[0126] Negative control mortality ranged between 0.79% and 3.91% and was corrected by using the Abbott formula.

[0127] [Table 7]

[0128] [Table 8]

[0129] [Example 5] Evaluation of flavesone as a grain protectant. The laboratory established an insect population of the grain boston beetle (Rhyzopertha dominica) (QRD1440) with a history of resistance to organophosphates and pyrethroids was used in this study.

[0130] Residue-free organically produced wheat grain was used in the study. The moisture content of the wheat was kept at 11%.

[0131] Test solutions of flavesone (25 ppm), deltamethrin (K-Obiol®, 1 ppm), and chlorpyrifos (Reldan®, 5 ppm and 10 ppm) in water were prepared. Water was used as a control. Five lots of 240 g of wheat were weighed into 1 L glass jars, one jar per treatment and one control.

[0132] Test and control solutions were pipetted into the inside of one of the jars (one jar per sample) just above the grain surface at a rate equivalent to 10 mL of solution per kg of wheat. The jars were sealed, briefly shaken and rolled by hand, and then mechanically rolled for 10 minutes. The moisture content was 12%, reflecting the upper limit allowed by bulk handling companies in Australia. The day after treatment, each 240 g wheat sample was divided into three 80 g replicates and placed into 250 mL glass jars.

[0133] Fifty adult R. dominica QRD1440 beetles (1 to 3 weeks post-emergence) were added to each jar of treated or control wheat. Each jar was covered with filter paper as a lid and stored at 25°C and 55% relative humidity for 14 days, after which the adult insects were recovered by sieving the wheat samples. Mortality was recorded. All dead and surviving adults were discarded. The wheat jars were incubated for an additional 6 weeks and the number of progeny was recorded. The results are shown in Table 9:

[0134] [Table 9]

[0135] At 25 ppm flavesone, the QDR1140 R. dominica resistant line had higher mortality than the control and the other pesticides used. Flavesone treatment also resulted in the production of fewer F1 progeny.

[0136] [Example 6] Flavesone concentration The experiment of Example 5 was repeated using flavesone at concentrations of 25 ppm, 50 ppm and 75 ppm. The control was water.

[0137] The results are shown in Table 10:

[0138] [Table 10]

[0139] [Example 7] Control of resistant strains of the rice boston moth QRD1440 (R. dominica) The experiment of Example 5 was repeated using flavesone at a concentration of 60 ppm. Water was used as a control.

[0140] The results are shown in Table 11.

[0141] [Table 11]

[0142] [Example 8] R. dominica QRD14 Comparative study using a susceptible strain of R. dominica. The experiment of Example 5 was repeated using a laboratory-grown susceptible strain of R. dominica, QQRD14, and different concentrations of flavesone to determine efficacy.

[0143] The results are shown in Table 12.

[0144] [Table 12]

[0145] [Example 9] Control of Halotydeus destructor (red-legged earth mite) - dose response in susceptible populations The efficacy of flavesone against H. destructor was determined using the glass vial technique developed by Hoffmann et al. (1997, Exp. Appl. Acarol., 21:151-162), adapted to plastic vials. Susceptible mite populations were collected from capeweed (Arctotheca calendula) at a field in Victoria (37°40'33"S, 145°07'45"E) with no known history of insecticide application. Following collection, samples were stored in small plastic containers with leaf material and paper towels to absorb excess moisture. Containers were kept at 4°C before testing.

[0146] Serial dilutions of each pesticide were prepared from the compositions shown in Table 13:

[0147] [Table 13]

[0148] The test compositions contained 0.1% Tween 20 nonionic surfactant to aid in the diffusion of the insecticide when coating the plastic vials. This concentration of Tween 20 has previously been shown to have no toxic effects on H. destructor. For each insecticide concentration tested: 3 mg, 10 mg, 30 mg, 100 mg, 300 mg, 1000 mg, 3000 mg, and 10,000 mg ai / L (ppm), approximately 10 mL of solution was poured into a 15 mL plastic vial and swirled to ensure complete coating and remove excess liquid. Eight vials per concentration were coated and allowed to dry overnight. Control vials were treated in the same manner, except that water was used instead of the test composition.

[0149] Eight susceptible H. destructor mites were then placed in each vial along with a vetch (Vicia sativa) leaf. The leaf was added to provide food and increase humidity. The vials were then sealed with lids and placed at 18°C. After 4, 6, 8, and 24 hours of exposure, the mites were scored as alive (freely moving), immobile (inhibited movement), or dead (no movement for a 5-second period). Immobile individuals were pooled with dead individuals for analysis, as they necessarily died and therefore did not contribute to the next generation.

[0150] Results for flavesone are shown in Figure 1. Mortality of H. destructor increased dramatically between 100 and 300 mg ai / L, with mortality increasing with the duration of exposure. At a 4-hour exposure, flavesone caused an average of 55% mortality at 300 mg ai / L, while less mortality was observed at application rates below this. All application rates above 300 mg ai / L resulted in 100% mortality by 4 hours of exposure. By 8 hours of exposure, mortality at 300 mg ai / L had risen to 100%. At lower application rates, increased mortality was observed at 24 hours.

[0151] [Example 10] Control of Halotydeus destructor (red-legged earth mite) - dose response in susceptible and resistant populations The experiment described in Example 9 was repeated using susceptible and resistant populations of H. destructor, with the exception that mites were observed at 6 and 24 hours. The resistant population of H. destructor was collected from lucerne pasture in the Upper South-East region of South Australia, where resistance to synthetic pyrethroids was confirmed in late 2016.

[0152] Data generated in the assays were determined for concentrations that caused 50%, 90%, and 99% mortality (lethal concentrations, LC), along with 95% confidence intervals (CI), and were estimated from observed mortality rates after 24 hours of exposure using binomial logistic regression (Robertson & Preisler, 1992, Pesticide Bioassays with Arthropods. CRC: Boca Raton; Venables & Ripley, 2002, Modern Applied Statistics with S. Springer: New York). Population differences were tested by comparing the change in model deviance in the presence or absence of a population factor (different regression intercept for each population). Differences in regression slopes between populations were tested by comparing the change in model deviance in the presence or absence of a population × dose interaction term. The resistance ratio of an insecticide-resistant population was calculated based on its LC 50 LC in susceptible populations 50 All analyses were performed using R3.3 (R Core Team 2017, R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria. http: / / www.R-project.org).

[0153] Dose-response curves showing the effect of flavesone on susceptible and resistant H. destructor populations after 24 hours of exposure are shown in Figure 2. Flavesone was equally effective against both insecticide-resistant and susceptible populations, as evidenced by the closely aligned dose-response curves for both populations (χ 2 =1.40, df=1, p=0.24). LC 50Values ​​(and 95% CIs) were calculated for flavesone as 40.6 (33.3-49.6) mg ai / L and 34.2 (27.9-41.9) mg ai / L for the susceptible and resistant populations, respectively, as shown in Table 14. There was no evidence that the regression slopes for concentrations were significantly different between populations (χ 2 =0.01, df=1, p0.91).

[0154] As shown in Figure 3 , a significant difference in susceptibility to bifenthrin was observed between the susceptible and resistant populations (χ 2 = 167.57, df = 1, p = 0.0001). Comparing LC50 values ​​between populations indicated that the resistant population required approximately 3,500 times the dose of bifenthrin compared to the susceptible population to achieve 50% mortality after 24 hours. This population likely contained a mixture of resistant and susceptible individuals. The LC50 value for the susceptible population of 0.04 (0.03-0.08) mg ai / L is consistent with previous studies using H. destructor collected from this location. The regression coefficients also differed significantly between populations (χ 2 =28.76, df=1, p=0.0001).

[0155] For chlorpyrifos, the dose response also differed significantly between insecticide-resistant and susceptible populations (χ 2 = 44.13, df = 1, p = 0.0001). The resistant populations were 6.5 times more resistant to chlorpyrifos than the sensitive populations. This is comparable to the organophosphate resistance seen in South Australia. There was no evidence that the regression slopes for concentration differed between populations. (χ 2 =1.77, df=1, p=0.18).

[0156] LD for 24-hour exposure 50 Value, LD 90 Value and LD 99 Values ​​and confidence intervals are shown in Table 14.

[0157] [Table 14]

[0158] These results indicate that flavesone is effective against H. destructor in both susceptible and insecticide-resistant populations, causing 50% mortality in 24 hours at concentrations between 34 and 40 mg ai / L.

[0159] [Example 11] Efficacy of flavesone against susceptible and resistant populations of Myzus persicae. Colonies of the green peach aphid (M. persicae) were established from long-term laboratory cultures of known insecticide-susceptible populations and populations previously shown to be resistant to carbamates and synthetic pyrethroids. Each colony was maintained separately on bok choy plants (Brassica napus chinensis) in exclusion cages in a constant-temperature room at 24°C with a 16:8 LD photoperiod.

[0160] A laboratory bioassay was used to determine the efficacy of flavesone against M. persicae according to the leaf-dip method described by Moores et al. (1994, Pesticide Biochemistry and Physiology, 49, 114-120). A pilot study was first conducted to confirm that the leaf-dip method was suitable for deriving a clear dose-response for flavoside 500 EW against M. persicae and to determine the appropriate percentage range and timing of mortality assessment (scored at 24, 48, 72, and 96 hours) (data not shown).

[0161] Bioassays were then conducted to determine the efficacy of flavesone against susceptible and resistant populations of green peach aphid (M. persicae) and to calculate LC values. The efficacy of a conventional insecticide, pirimicarb, was tested for comparison. At the proposed field rate of 1 x 10-3 Nine concentrations of flavesone ranging from 0.1 to 10-fold (Table 15) and six concentrations of pirimicarb were serially diluted and tested against susceptible and resistant aphid populations, along with a water control. Leaf discs (25 mm diameter) excised from bok choy leaves were submerged in the insecticide solution or water control for 1 second and placed adaxial side up on 10 g / L agar in 35 mm Petri dishes. Six replicate leaf discs were prepared per treatment. Once the leaves were air-dried, a fine-bristled paintbrush was used to transfer eight green peach aphid (M. persicae) nymphs to each insecticide-soaked leaf disc.

[0162] After aphid introduction, each Petri dish was inverted onto a lid containing 25 mm diameter filter paper to control humidity. All Petri dishes were then placed in an incubator maintained at 18°C ​​± 2°C with a 16:8 LD cycle photoperiod. At 48 and 96 hours, aphids were scored as alive (vital and freely moving), dead (not moving for a 5 second period), or immobile (inhibited movement). Immobile individuals were pooled with dead individuals for analysis, as they necessarily died and therefore did not contribute to the next generation.

[0163] [Table 15]

[0164] Data analysis Dose-response curves were generated by plotting the percentage mortality against the log concentration. Mortality data were analyzed using a logistic regression model with random effects. Logistic regression is appropriate for analyzing binary response data (i.e., death / survival) with a random effects component in the model that controls for non-independence of mortality scores within replicates. Concentrations resulting in 50%, 90%, and 99% mortality (lethal concentrations, LC) (with 95% confidence intervals, CI) were calculated using binomial logistic regression (Robertson & Preisler 1992, Pesticide Bioassays with Arthropods, CRC: Boca Ratan; Venables & Ripley 2002, Modern Applied Statistics with S, Springer, New York, http: / / www.stats.ox.ac.uk / pub / MASS4). Population differences were tested by comparing the change in model deviance in the presence or absence of population factors (different regression intercepts for each population). Differences in regression slopes between populations were tested by comparing the change in model deviance with and without the population × dose interaction term.

[0165] Analyses were performed using R version 3.3.1 (R Development Core Team 2017. R: A language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, Austria, http: / / R-project.org).

[0166] result While the dose-response curves for susceptible and resistant populations exposed to flavesone appeared similar at 48 h (Figure 5), significant differences between populations were detected (c2 = 8.09, df = 1, p < 0.01). However, by 96 h, the dose-response curves for susceptible and resistant M. persicae populations exposed to flavesone were more closely aligned and not significantly different (c2 = 0.78, df = 1, p = 0.38) (Figure 6). LC50 values ​​(and 95% CI) after 96 h of exposure were estimated as 2,731 (2,259–3,303) mg ai / L for the susceptible population and 3,151 (2,568–3,865) mg ai / L for the resistant population (Table 16). The regression slopes between groups were not significantly different at 48 hours (c2 = 0.49, df = 1, p = 0.48) or 96 hours (c2 = 0.72, df = 1, p = 0.40).

[0167] [Table 16]

[0168] At 48 and 96 hours, there were no clear differences in the dose-response curves between susceptible and resistant populations after exposure to pirimicarb (48 hours: c2 = 269.9, df = 1, p < 0.0001; 96 hours: c2 = 257.5, df = 1, p < 0.0001) (Figures 7 & 8). The regression slopes were also significantly different between populations (48 hours: c2 = 66.6, df = 1, p < 0.0001; 96 hours: c2 = 107.2, df = 1, p < 0.0001). The estimated LC50 for the susceptible population after 96 hours of 18.5 mg ai / L is consistent with previous laboratory studies using the green peach aphid (M. persicae) (Umina et al. 2014, Journal of Economic Entomology, 107(4), 1626 1638). The very low mortality observed for the resistant population when exposed to pirimicarb prevented the calculation of meaningful LC values ​​(Table 16).

[0169] This study demonstrates that flavesone is effective against the green peach aphid (M. persicae). The LC50 for flavesone after 96 hours of exposure was between 2,731 and 3,151 mg ai / L. Pirimicarb efficacy was very high against susceptible populations and closely aligned with previously published bioassay data. We confirmed resistance to pirimicarb in insecticide-resistant populations. This population is also resistant to synthetic pyrethroids, as demonstrated by pesticide bioassay results and genetic screening (see Umina et al., 2014).

[0170] The dose-response curves for flavesone for sensitive and resistant populations were closely aligned at 96 hours after exposure, demonstrating that flavesone is effective against populations of M. persicae that are resistant to carbamates and that flavesone acts differently from this class of insecticides. mechanism There is some evidence for population differences in response after 48 hours. The reason(s) for this remain unclear but may reflect natural differences between populations, such as colony health, general cold tolerance, or bacterial endosymbionts.

[0171] [Example 12] Toxicity of flavesone to Aedes aegypti LVP (insecticide-susceptible and PRS insecticide-resistant strain L3 larvae). Mosquito larvae topical assay technique was performed.

[0172] Lethal concentration (LC) 50 To determine ) values, a dose-response assay was used, performed with a minimum of four technical replicates per dose (five mosquitoes per replicate) and a minimum of five doses of flavesone diluted in sterile ddH2O.

[0173] Two species of mosquitoes were used: Aedes aegypti (yellow fever mosquito) Liverpool strain (insecticide susceptible, LVP) and PRS Puerto Rico strain (synthetic pyrethroid resistant) at the L3 larval stage. Negative control: vehicle Positive controls: technical grade synthetic pyrethroids (SP) and organophosphates (OP): deltamethrin (SP), permethrin (SP) and malathion (OP). Phenotypic endpoints: Death / paralysis scored at 24, 48 and 72 hours. Dose points (selected from pilot assays not shown): Flavesone: 6.25 μg / mL, 25.0 μg / mL, 50 μg / mL, 75 μg / mL & 100 μg / mL; H2O control Deltamethrin: 1.56ng / mL, 6.25ng / mL, 12.5ng / mL, 25ng / mL, 50ng / mL; 0.625% DMSO negative control Permethrin: 6.25ng / mL, 12.5ng / mL, 25ng / mL, 50ng / mL, 100ng / mL; 0.625% DMSO negative control Malathion: 0.0156 μg / mL, 0.0625 μg / mL, 0.125 μg / mL, 0.25 μg / mL, 1 μg / mL; 0.5% EtOH negative control

[0174] Larvae were transferred to 24-well tissue plates at five larvae per well using a wide-bore plastic transfer pipette. Water was gently removed from the wells with a 1 mL pipette, and an equal volume of ddH2O was added. An appropriate volume of test compound was added to each of four replicate wells per treatment, and the plate was gently swirled to ensure uniform mixing. Plates were placed in a test or growth chamber under constant conditions of 22-25°C and approximately 75-85% relative humidity on a 12-hour light / 12-hour dark cycle. Mortality and non-responsive larvae were assessed at 24, 48, and 72 hours.

[0175] The results are shown in Table 17.

[0176] [Table 17]

[0177] [Example 12] Evaluation of flavesone as a grain protectant against major stored grain pests resistant to commonly used pesticides. insect Five laboratory-established strains (both susceptible and resistant) of the species were considered for this stage of the experiment. The resistant strains listed below represent grain protectant-resistant genotypes commonly encountered in grain storage in Australia, particularly in the eastern grain belt: The R. dominica strain QRD1440 is resistant to OP protectants and pyrethroids. The red flour beetle (T. castaneum) strain QTC279 is resistant to malathion and bioresmethrin The rust beetle C. ferrugineus strain QCF73 is resistant to phosphine The sawtoothed aphid (O. surinamensis) strain QOS302 is resistant to fenitrothion and chlorpyrifos-methyl The rice weevil (S. oryzae) strain QSO393 is resistant to fenitrothion

[0178] Testing Program Grain Treatments and Bioassays Organically produced, residue- and insect-free wheat was used for this study. The moisture content of the wheat before treatment was maintained at 11%. Chemicals for use in these experiments: Flavesone, K-Obiol EC Combi (50 g / L deltamethrin, 400 g / L PBO), and Reldan (500 g / L chlorpyrifos-methyl) were obtained from Bio-Gene Technology, Bayer Crop Science, and Dow AgroSciences, respectively. For the stand-alone Flavesone experiments, two rates (25 ppm and 60 ppm) were considered.

[0179] For each strain of borer (internal feeder), rice boston beetle (R. dominica), and rice weevil (S. oryzae), three 160g lots of wheat were weighed into glass jars (500mL capacity): one jar per treatment and another for the control (distilled water only). Each treatment solution (prepared at the prescribed dilution rate as an individual and combination) was separately pipetted onto the inside of the glass jar just above the grain surface at a rate equivalent to 10mL of solution per kilogram of wheat. Distilled water was applied to the control grain at the same rate as the treatment. All jars were sealed, briefly shaken and rolled by hand, and then mechanically rolled for 1 hour. The moisture content after treatment was 12%, reflecting the upper limit allowed by Australian bulk handling companies. One day after treatment, each 240 g lot of wheat was divided into three 80 g replicates, which were placed in separate glass jars (250 mL volume). The procedure for T. castaneum, C. ferrugineus, and O. surinamensis was kept the same, except that three 600 g lots of wheat per plant were treated. One day after treatment, each 600 g lot of wheat was divided into three 190 g replicates, which were then placed in glass jars (500 mL volume). The remaining 30 g of wheat was ground into flour, divided into three 10 g replicates, and added to the associated replicate of whole wheat, so that each replicate weighed a total of 200 g. The aim of grinding 5% of each replicate into flour was to improve the reproduction of these three external feeder pest species. The above activity was repeated twice over the next two days to create a total of three replicates for each treatment.

[0180] Bioassays were initiated by adding 50 adult beetles (1–3 weeks post-emergence) to each jar of treated or control wheat. Each jar was covered with a filter paper lid and stored in a constant-environment room at 25°C and 55% relative humidity for 2 weeks, after which the adults were sieved from the wheat and mortality recorded. All adults (dead and alive) were then discarded, and the wheat jars were incubated for an additional 6 weeks, at which time the number of adult progeny was recorded. To synchronize progeny emergence, jars containing S. oryzae and O. surinamensis were incubated at 25°C and 55% relative humidity, while jars containing other species were incubated at 30°C and 55% relative humidity.

[0181] Data analysis Each data set is presented in a simple table, along with the percentage adult mortality and number of surviving adult F1 progeny for each species (mean ± standard error of three replicates), as well as the percentage progeny reduction calculated from the mean number of F1 progeny in treated wheat and untreated controls.

[0182] result The effectiveness of Flavesone Control mortality in both susceptible and resistant strains of all five species was negligible (0-1.3%) (Tables 18-22). The number of adult progeny produced in the R. dominica controls was 234 and 211 for the susceptible (QRD14) and resistant (QRD1440) strains, respectively (Table 18); 118 (QTC4) and 321 (QTC279) for T. castaneum (Table 19); 360 (QCF31) and 344 (QCF73) for C. ferrugineus (Table 20); 348 (VOS48) and 412 (QOS302) for O. surinamensis (Table 21); and 716 (LS2) and 610 (QSO393) for the susceptible and resistant S. oryzae strains, respectively (Table 22).

[0183] As expected, 25 ppm flavesone failed to achieve complete adult mortality in both susceptible (QRD14) and resistant (QRD1440) strains of R. dominica, but achieved 100% and 88% progeny reduction in the respective strains (Table 18). However, when Phase I results were examined, a higher rate of 60 ppm flavesone achieved complete adult and progeny control in both strains (Table 1).

[0184] For strains of the other four species, however, both of the proposed rates (25 ppm and 60 ppm) of flavesone failed to achieve complete adult mortality (Tables 19-22); complete progeny reduction was achieved at 60 ppm in C. ferrugineus and O. surinamensis (Tables 20 and 22). Both rates of flavesone were not successful for susceptible (QTC4) and resistant (QTC279) strains of T. castaneum; adult mortality was not achieved, with progeny reductions of up to 45% for the former and 36% for the latter at the higher rate of 60 ppm (Table 19). For C. ferrugineus, adult mortality reached 90% and 62% in susceptible (QCF31) and resistant (QCF73) strains, respectively, at the highest dose of 60 ppm (Table 20). At the lower dose of 25 ppm, progeny reduction in this species was recorded at similar levels of 75% for both strains, with 100% progeny reduction recorded at the 60 ppm level (Table 20). In the case of O. surinamensis, flavesone achieved adult mortality of 22% and 0.7% in susceptible (VOS48) and resistant (QOS302) strains, respectively, at 25 ppm; and up to 91% in the former and 14% in the latter at the higher dose of 60 ppm (Table 21). Both rates of flavesone, however, produced very high percentage progeny reduction (61-99%) at 25 ppm and complete progeny reduction (100%) at 60 ppm in both strains of this species (Table 21). The effectiveness of flavesone against S. oryzae was similar to that observed against T. castaneum (Tables 18 and 22). Both rates failed to achieve any significant mortality against adults of either strain (Table 22). At 60 ppm, however, flavesone achieved 29% and 50% progeny reduction in the resistant (QSO393) and susceptible (LS2) strains, respectively (Table 22).

[0185] [Table 18]

[0186] [Table 19]

[0187] [Table 20]

[0188] [Table 21]

[0189] [Table 22]

[0190] [Example 13] Evaluation of the combination of flavesone and chlorpyrifos-methyl (Reldan) against major stored grain pests resistant to commonly used pesticides. The experiment of Example 12 was repeated using a combination of flavesone and chlorpyrifos-methyl.

[0191] Across all combination treatment experiments, control mortality in both susceptible and resistant strains of all five species was negligible (0-3%) (Tables 23-27). The number of adult progeny produced in the R. dominica controls was 186 for the susceptible (QRD14) and resistant (QRD1440) strains (Table 23), 59 (QTC4) and 480 (QTC279) for T. castaneum (Table 24), 467 (QCF31) and 188 (QCF73) for C. ferrugineus (Table 25), 526 (VOS48) and 429 (QOS302) for O. surinamensis (Table 26), and 720 (LS2) and 565 (QSO393) for the susceptible and resistant S. oryzae strains, respectively (Table 27).

[0192] All experimental combinations of flavesone and chlorpyrifos-methyl, applied at both higher and lower rates, were highly successful against susceptible strains of all five test species, with 100% adult mortality and progeny reduction (Tables 23-27). The efficacy of all these combinations was greatest against resistant strains of C. ferrugineus, where complete control of adults and progeny was achieved (Table 26). Furthermore, with the exception of a 99% progeny reduction in the pairwise combination, all these treatments achieved 100% progeny control in resistant strains of T. castaneum (QTC279), O. surinamensis (QOS302), and S. oryzae (QSO393) (Tables 24, 26, and 27). For a resistant strain of R. dominica (QRD1440), however, complete adult mortality was achieved only with the combination of flavesone 60 + chlorpyrifos-methyl 5, and complete progeny reduction was achieved in grain treated with the combinations of flavesone 30 + chlorpyrifos-methyl 10, flavesone 60 + chlorpyrifos-methyl 5, and flavesone 60 + chlorpyrifos-methyl 10 (Table 23).

[0193] [Table 23]

[0194] [Table 24]

[0195] [Table 25]

[0196] [Table 26]

[0197] [Table 27]

[0198] Table 28 summarizes the efficacy of the combination of chlorpyrifos-methyl and flavesone.

[0199] [Table 28]

[0200] [Example 14] Evaluation of the combination of flavesone and deltamethrin (K-Obiol) against susceptible and resistant strains of the diamondback moth (R. dominica). The experiment of Example 12 was repeated using a combination of flavesone and deltamethrin with the susceptible and resistant R. dominica strains QRD14 and QRD1440.

[0201] In these experiments, control mortality remained below 1% for both susceptible and resistant strains of this species, and similar numbers of surviving adult progeny (126 and 125) emerged (Table 29). In all combinations, complete control of both adults and progeny was achieved against the susceptible strain (QRD14), and high levels of control were achieved against the resistant strain (QRD1440) (Table 29). Against resistant adults, all combinations resulted in a mortality percentage of 93-100%. Similarly, all combinations resulted in a 99-100% reduction in progeny of the resistant strain QRD1440 (Table 29).

[0202] The results are shown in Table 29.

[0203] [Table 29] The present invention includes the following aspects. [1] A method for controlling pesticide-resistant pests, comprising treating the pesticide-resistant pests with a compound of formula (I): [ka] (In the formula, R 1 is -C(=O)R 7 , -OR 8 , -SR 8 、-C 1~10 Hydroxyalkyl, -NR 9 R 10 , -C(=NR 9 )R 7 , -C(=N-OH)R 7 , -NO, -NO 2 , -N(OR 8 )R 7 and -OSO 3 R 8 is selected from R 2 is hydrogen, -C 1~10 Alkyl, -C 2~10 selected from alkenyl, aryl and heteroaryl; R 3 、R 4 、R 5 and R 6 is hydrogen, -C 1~10 Alkyl, -C3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -OR 8 , -SR 8 , -NR 9 R 10 , -C(=NR 9 )R 7 , -NO, -NO 2 , -NR 9 OR 8 , -OSO 3 R 8 、-C 1~10 Alkylaryl and -C(=O)R 7 are each independently selected from R 7 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl, -C 1~10 Nitroalkyl, -C 1~3 Alkyl OC 1~3 Alkyl, -C 1~3 Alkyl OC 1~3 Haloalkyl, -C 1~3 Alkyl OC 1~3 Dihaloalkyl, -C 1~3 Alkyl OC 1~3 Trihaloalkyl, -OR 8 , -SR 8 and -NR 9 R 10 is selected from R 8 is hydrogen, -C1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 Trihaloalkyl, -C 1~10 Haloalkoxy, -C 1~10 Hydroxyalkyl, -C 1~10 Thioalkyl and -C 1~10 nitroalkyl; R 9 and R 10 is hydrogen, -C 1~10 Alkyl, -C 2~10 Alkylaryl, -C 3~6 Cycloalkyl, -C 2~10 Alkenyl, -C 1~10 Alkylheteroaryl, -C 1~10 Haloalkyl, -C 1~10 Dihaloalkyl, -C 1~10 trihaloalkyl) or a tautomer thereof. [2] The compound of formula (I) is represented by formula (II):

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[10] The method according to [9], wherein the cattle tick is a larva.

[11] The method of any of [1] to

[10] , wherein the pesticide-resistant pest is exposed to the compound of formula (I) in an amount ranging from about 200 ppm to about 800 ppm, or from about 800 ppm to about 2,500 ppm.

[12]

[11] The method according to

[11] , wherein the amount of the compound of formula (I) is in the range of about 300 ppm to about 600 ppm.

[13] The method according to

[11] , wherein the amount of the compound of formula (I) is in the range of 900 ppm to 2000 ppm.

[14] [7] The method according to [7], wherein the insect is selected from the group consisting of the mealybug (Rhyzopertha dominica), the rice weevil (Sitophilus oryzae), the red flour beetle (Triobolium castaneum), the sawtoothed flathead beetle (Oryzaephilus surinamensis), and the rust-headed flathead beetle (Cryptolestes ferrugineus).

[15] The method according to

[14] , wherein the insect is an adult.

[16] The method of [7], wherein the spider is selected from Halotydeus destructor, Penthaleus, Balaustium medicagoense and Bryobia mites.

[17] The method according to

[16] , wherein the spider is infesting a crop.

[18] The method according to any one of [1] to

[17] , wherein the compound of formula (I) is used as part of an integrated pest management system.

[19] The method of any of [1] to

[18] , wherein the pesticide-resistant pest is exposed to a compound of formula (I) in combination with a second pesticide.

[20] The method of

[19] , wherein the second pesticide has a different mode of action than the compound of formula (I).

[21] The method of

[19] or

[20] , wherein the second pesticide is selected from at least one of a sodium channel modulator, an acetylcholinesterase (AChE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a chloride channel actuator, a juvenile hormone mimetic, 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 molting disruptor, an ecdysone receptor agonist or disruptor, an octapamine receptor agonist, 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, or a ryanodine receptor modulator.

[22] A method for controlling pesticide-resistant mites, comprising exposing the pesticide-resistant mites to a compound of formula (I) described in any one of [1] to [6].

[23] 1. A method for treating or preventing pest infestation in livestock or companion animals, comprising administering to said animal a compound of formula (I):

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[24] 1. A method for controlling pest populations, comprising administering to a subject a compound of formula (I)

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[25] 1. A method for protecting stored plant parts from pest infestation, comprising:

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[26]

[24] The method according to

[24] , wherein the plant part is a grain.

[27]

[24] The method according to

[25] , wherein the pest population including pesticide-resistant pests is selected from the group consisting of Rhyzopertha dominica, Sitophilus oryzae, Triobolium castaneum, Oryzaephilus surinamensis, and Cryptolestes ferrugineus.

Claims

1. A method for controlling pesticide-resistant pests, wherein the pesticide-resistant pests are insect or arachnid pests that infest or infest an agricultural environment selected from crops, trees, and the soil and areas around plants as they grow, and the pesticide-resistant pests are insects that are resistant to one or more insecticides that have previously been used to control insects, or spiders that are resistant to one or more arachnids that have previously been used to control spiders, the method comprising exposing the pesticide-resistant pests to a compound selected from flavesone, leptospermone, and isoleptospermone.

2. 10. The method of claim 1, wherein the pesticide-resistant pest is exposed to the compound in an amount ranging from 200 ppm to 800 ppm, or from 800 ppm to 2,500 ppm.

3. The amount of the compound i) in the range of 300 ppm to 600 ppm; or ii) in the range of 900 ppm to 2000 ppm The method according to claim 2, wherein the method is either one of

4. 2. The method of claim 1, wherein the insect is selected from the group consisting of the mealybug (Rhyzopertha dominica), the rice weevil (Sitophilus oryzae), the red flour beetle (Triobolium castaneum), the sawtoothed flathead beetle (Oryzaephilus surinamensis), and the rust beetle (Cryptolestes ferrugineus).

5. The method of claim 4, wherein the insect is an adult.

6. 2. The method of claim 1, wherein the spider is selected from Halotydeus destructor, Penthaleus, Balaustium medicagoense, and Bryobia mites.

7. The method of claim 6, wherein the spider is infesting a crop.

8. 8. The method of any one of claims 1 to 7, wherein the compound is used as part of an integrated pest management system.

9. 9. The method of any one of claims 1 to 8, wherein a pesticide-resistant pest is exposed to the compound in combination with a second pesticide.

10. 10. The method of claim 9, wherein the second pesticide has a different mechanism of action than the compound.

11. 11. The method of claim 9 or 10, wherein the second pesticide is selected from at least one of a sodium channel modulator, an acetylcholinesterase (AChE) inhibitor, a GABA-gated chloride channel antagonist, a nicotinic acetylcholine receptor agonist, an allosteric acetylcholine receptor modulator, a chloride channel actuator, a juvenile hormone mimetic, 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 molting disruptor, an ecdysone receptor agonist or disruptor, an octapamine receptor agonist, 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, or a ryanodine receptor modulator.

12. 1. A method for controlling populations of pests, comprising applying a compound selected from flavesone, leptospermone and isoleptospermone to an agricultural environment selected from crops, trees, and the soil and area around plants as they grow, which is infested or infested with said populations of pests; The method wherein the population of pests comprises insects resistant to one or more insecticides previously used to control insects or spiders resistant to one or more arachnides previously used to control spiders.

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