Substituted benzisoxazole compounds, methods for their preparation, insecticidal compositions and uses thereof

Abstract

The application belongs to the technical field of pesticides, and particularly relates to a substituted benzisoxazole compound and a composition and application thereof. The compound is shown in the general formula I: wherein any one of X1, X2, X3 and X4 is N, and the other three are independently CR1; R1 is independently hydrogen, halogen, alkyl, alkenyl or the like; X is alkyl, haloalkyl or alkenyl or the like; and Y is alkyl. The compound has excellent control effects on pests such as Spodoptera frugiperda, Mythimna separata, Helicoverpa armigera and Plutella xylostella.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a substituted benzisoxazole compound, its preparation method, insecticidal composition, and application. Background Technology

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term persistence. Therefore, despite the large number of known pesticides, there is a need to develop new pest control agents with low toxicity and low residue. Summary of the Invention

[0003] To address the aforementioned problems in the prior art, this invention provides a substituted benzisoxazole compound, its preparation method, an insecticidal composition, and its application. The compound exhibits excellent control effects against pests such as fall armyworm, armyworm, beet armyworm, and diamondback moth.

[0004] The technical solution adopted in this invention is as follows:

[0005] A substituted benzisoxazole compound, as shown in general formula I:

[0006]

[0007] In this context, any one of X1, X2, X3, and X4 is N, and the other three independently represent CR1.

[0008] R1 independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR 10 S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 , cycloalkyl, aryl or heterocyclic; wherein the alkyl, alkenyl or ynyl group is optionally selected from halogen, trialkylsilyl, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from cycloalkyl, heterocyclic or aryl groups;

[0009] X represents alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, -N(R) 10 2. Cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl;

[0010] Y represents alkyl;

[0011] R 10 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclic, heterocyclic alkyl, aryl, or arylalkyl.

[0012] m represents 0, 1, or 2;

[0013] The aforementioned "cycloalkyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure.

[0014] R 11 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0015] In one specific embodiment, R1 independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -OR 10 -S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 C3-C8 cycloalkyl, aryl, or heterocyclic groups; wherein, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is optionally selected from halogens, tri-C1-C8 alkylsilyl groups, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from C3-C8 cycloalkyl, heterocyclic or aryl groups;

[0016] X represents C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 ynyl, halogenated C2-C8 ynyl, -N(R) 10 2. C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, aryl, heterocyclic, aryl C1-C8 alkyl or heterocyclic C1-C8 alkyl;

[0017] Y represents C1-C8 alkyl;

[0018] R 10 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, heterocyclic, heterocyclic-C1-C8 alkyl, aryl or aryl-C1-C8 alkyl;

[0019] m represents 0, 1, or 2;

[0020] The aforementioned “C3-C8 cycloalkyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure.

[0021] R 11 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

[0022] In another specific embodiment, R1 independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, -OR 10 -S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 C3-C6 cycloalkyl, aryl, or heterocyclic groups; wherein, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally selected from halogens, tri-C1-C6 alkylsilyl groups, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from C3-C6 cycloalkyl, heterocyclic or aryl groups;

[0023] X represents C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 ynyl, halogenated C2-C6 ynyl, -N(R) 10 2. C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, heterocyclic, aryl C1-C6 alkyl or heterocyclic C1-C6 alkyl;

[0024] Y represents C1-C6 alkyl;

[0025] R 10 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, heterocyclic, heterocyclic-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl.

[0026] m represents 0, 1, or 2;

[0027] The aforementioned “C3-C6 cycloalkyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure.

[0028] R 11 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

[0029] In another specific implementation, X1 is N, and X2, X3, and X4 each independently represent CR1;

[0030] X2 is N, and X1, X3, and X4 each independently represent CR1;

[0031] X3 is N, and X1, X2, and X4 independently represent CR1; or,

[0032] X4 represents N, and X1, X2, and X3 each independently represent CR1.

[0033] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "cycloalkylalkyl," the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0034] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups.

[0035] And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0036] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0037] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0038] Another embodiment of this application is a method for preparing the substituted benzisoxazole compound, comprising the following steps:

[0039] The compound represented by general formula II reacts with the compound represented by general formula III to produce the compound represented by general formula I, and the reaction equation is as follows:

[0040]

[0041] In this case, either Q1 or Q2 is halogen, and the other is... The definitions of X, Y, X1, X2, X3, and X4 are as shown above.

[0042] In one specific embodiment, the reaction is carried out in the presence of a base, a catalyst, and a solvent;

[0043] In another specific embodiment, the base is selected from at least one of inorganic bases (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, etc.) or organic bases (such as DMAP, pyrazole, triethylamine, DIEA, etc.);

[0044] In another specific embodiment, the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(OAc)2, PdCl2 or 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex;

[0045] In another specific embodiment, the solvent is an organic solvent / water, wherein the organic solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0046] The preparation method of the compound described in this invention can be found in CN118355004A, etc.

[0047] The present invention also relates to an intermediate, as shown in Formula II above.

[0048] The present invention also relates to the use of compounds of formula I (including all stereoisomers), their N-oxides and salts, and compositions comprising them in the control of pests.

[0049] The present invention also provides an insecticidal composition comprising at least one of a compound of formula I, its N-oxide, or a salt thereof.

[0050] In one specific embodiment, it also includes a formulation adjuvant.

[0051] In one specific embodiment, other active ingredients are also included.

[0052] The present invention provides a method for controlling pests, the method comprising exposing the pest or its environment to a biologically effective amount of a compound of formula I, its N-oxide or its salt, or a combination thereof.

[0053] The pest environment described above refers to plants, animals, or seeds.

[0054] The present invention also provides a method for protecting seeds from invertebrate pests, the method comprising contacting the seeds with a biologically effective amount of a compound of formula I, its N-oxide, or a salt thereof. The present invention also relates to treated seeds.

[0055] The present invention also provides compositions for protecting animals from invertebrate parasitic pests, the compositions comprising an effective amount of a compound of formula I, its N-oxide or a salt thereof, and at least one carrier.

[0056] The present invention also provides methods for treating, preventing, inhibiting, and / or killing external and / or internal parasites, said methods comprising applying to and / or onto an animal an effective amount of a compound of formula I, its N-oxide, or a salt thereof. The present invention also relates to such methods, wherein an effective amount of a compound of formula I, its N-oxide, or a salt thereof is applied to the environment in which the animal inhabits (e.g., a pen or blanket).

[0057] As used in this disclosure, the term "invertebrate pest" includes arthropods, gastropods, and nematodes that are economically important pests. The term "arthropods" includes insects, mites, spiders, scorpions, centipedes, millipedes, pill bugs, and animals of the class Symphylans. The term "gastropods" includes snails, slugs, and other animals of the order Stylommatophora. The term "nematodes" refers to organisms belonging to the phylum Nematoda. The term "worms" includes ascarids, canine filariasis, herbivorous nematodes (Nematoda), trematodes (trematodes), acanthocephalans, and tapeworms (taenia).

[0058] In the context of this invention, "controlling invertebrate pests" refers to inhibiting the growth of invertebrate pests (including death, decreased food intake, and / or mating interference), and similar related expressions may be defined.

[0059] The term "agronomy" refers to the growth of field crop products, such as food and fiber, and includes corn, soybeans and other legumes, rice, cereal foods (such as wheat, oats, barley, rye, rice, and corn), leafy vegetables (such as lettuce, cabbage, and other pod crops), fruit vegetables (such as tomatoes, peppers, eggplants, cruciferous plants, and cucurbitaceous plants), potatoes, sweet potatoes, grapes, cotton, woody fruits (such as pome, hard-seed, and citrus), small fruits (berries, cherries), and other specialty crops (such as low-erucic acid rapeseed, sunflowers, and olives).

[0060] The term "non-agricultural" refers to applications that are not field crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, or ornamental plants that are not grown in fields), residential structures, agronomic structures, commercial and industrial structures, turf (e.g., grasslands, pastures, golf courses, lawns, sports fields, etc.), wood products, stored products, agroforestry and vegetation management, and public health (i.e., human and animal health) applications (e.g., domesticated animals such as pets, livestock and poultry, and undomesticated animals such as wild animals).

[0061] Non-agricultural applications include protecting animals from invertebrate parasitic pests by administering to them an effective (i.e., bioeffective) amount of the compounds of the present invention (typically in the form of compositions formulated for veterinary use). As used in this disclosure and claims, the terms "parasitic" and "parasitic" refer to observed effects on invertebrate parasitic pests that provide protection to animals against the pests. Parasitic effects generally involve reducing the presence or activity of the target invertebrate parasitic pest. Such effects on pests include necrosis, lethality, growth retardation, reduced mobility or decreased ability to remain on or in a host animal, decreased food intake, and inhibition of reproduction. These effects on invertebrate parasitic pests provide control (including prevention, reduction, or elimination) of parasitic infestation or infection in animals.

[0062] The compounds of the present invention can exist in the form of one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, transisomers, and geometric isomers. Those skilled in the art will recognize that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to other stereoisomers or when isolated from other stereoisomers. Furthermore, those skilled in the art know how to isolate, enrich, and / or selectively prepare said stereoisomers. The compounds of the present invention can exist as mixtures of stereoisomers, individual stereoisomers, or as optically active forms.

[0063] Because bond rotation is restricted due to steric hindrance, the compounds of this invention can exist in one or more conformational isomers. This invention includes mixtures of conformational isomers. Furthermore, this invention includes compounds enriched in one conformational isomer relative to other conformational isomers.

[0064] Compounds selected from Formula I (including all its stereoisomers, its N-oxides, and its salts) generally exist in more than one form, thus Formula I includes all compounds in crystalline and amorphous forms represented by Formula I. Amorphous forms include embodiments that are solids such as waxes and gums, and embodiments that are liquids such as solutions and melts. Crystalline forms include embodiments representing substantially a single crystal form, and embodiments representing mixtures of polymorphs (i.e., different crystal forms). The term "polymorph" refers to a specific crystal form of a chemical compound that can crystallize in different crystal forms, which have different molecular arrangements and / or conformations in the crystal lattice. While polymorphs may have the same chemical composition, they may also have different compositions, which should be attributed to the presence of water or other molecules that are weakly or strongly bonded to the crystal lattice for co-crystallization. Polymorphs may have different chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, solubility, and bioavailability. Those skilled in the art will recognize that, relative to another polymorph or mixture of polymorphs of the same compound represented by Formula I, the polymorph of the compound may exhibit beneficial effects (e.g., suitability for preparation of usable formulations, improved biological properties). The preparation and separation of specific polymorphs of the compound represented by Formula I can be achieved by methods known to those skilled in the art, including, for example, crystallization using a selected solvent and temperature.

[0065] Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides, because nitrogen requires available lone pairs of electrons to be oxidized to oxides; those skilled in the art will identify those nitrogen-containing heterocycles that can form N-oxides. Those skilled in the art will also know that tertiary amines can form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are well known to those skilled in the art, including the use of peroxy acids (such as peracetic acid and 3-m-chloroperoxybenzoic acid (MCPBA)), hydrogen peroxide, alkyl hydroperoxides (such as tert-butyl hydroperoxide), sodium perborate, and diethylene oxides (such as dimethyldiethylene oxide) to oxidize heterocycles and tertiary amines.

[0066] Those skilled in the art recognize that salts and their corresponding non-salt forms of chemical compounds share common biological uses because they are in equilibrium under environmental and physiological conditions. Therefore, a wide variety of salts of Formula I compounds can be used to control invertebrate pests and animal parasites (i.e., for animal health purposes). Salts of Formula I compounds include acid addition salts formed with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When a Formula I compound contains an acidic moiety such as a carboxylic acid or phenol, the salt also includes those formed with an organic or inorganic base such as pyridine, triethylamine, or ammonia, or an ammonium, hydride, hydroxide, or carbonate of sodium, potassium, lithium, calcium, magnesium, or barium. Therefore, the present invention includes compounds selected from Formula I compounds, their N-oxides, and salts.

[0067] The embodiments of the invention described in the summary of the invention include those listed below. In the following embodiments, Formula I includes its stereoisomers, its N-oxides, and its salts, and unless otherwise defined in the embodiments, the description of “compound of Formula I” includes the definition of the specified substituents in the summary of the invention.

[0068] It is worth noting that the compounds of the present invention are characterized by favorable metabolic and / or soil residue patterns and exhibit broad-spectrum control activity against agronomic and non-agronomic invertebrate pests.

[0069] Of particular note is that, due to its broad-spectrum control of invertebrate pests and its economic importance, protecting crops from damage or injury caused by invertebrate pests is an embodiment of the present invention. Because of the advantageous transfer properties or systemic nature of the compounds of the present invention within the plant, they also protect leaves or other plant parts that are not in direct contact with the compound of Formula I or a composition containing said compound.

[0070] As an embodiment of the present invention, it is also worth noting the composition comprising any of the compounds in the foregoing embodiments and any other embodiments described herein, and any combination thereof, and at least one additional component and / or formulation adjuvant and / or at least one active ingredient (i.e., a biologically active compound or reagent), said additional component being selected from surfactants, solid diluents and liquid diluents.

[0071] Embodiments of the present invention also include compositions for protecting animals, said compositions comprising any of the compounds in the foregoing embodiments (i.e., an effective amount for killing parasites) and a carrier.

[0072] Embodiments of the present invention also include methods for controlling invertebrate pests, the methods comprising exposing invertebrate pests or their environment to a biologically effective amount of any of the compounds in the foregoing embodiments (e.g., the compositions described herein). Particularly noteworthy are methods for protecting animals, the methods comprising administering to animals a parasite-killing effective amount of any of the compounds in the foregoing embodiments (e.g., the compositions described herein).

[0073] Embodiments of the invention also include compositions comprising any of the compounds described in the foregoing embodiments, in the form of a soil soaking liquid formulation. Embodiments of the invention also include a method for controlling invertebrate pests, the method comprising contacting soil with a liquid composition comprising a bioavailable amount of any of the compounds described in the foregoing embodiments as a soil soaking solution.

[0074] Embodiments of the invention also include a spray composition for controlling invertebrate pests, the composition comprising any of the compounds in the foregoing embodiments (i.e., a bioeffective amount) and a propellant. Embodiments of the invention also include a bait composition for controlling invertebrate pests, the composition comprising any of the compounds in the foregoing embodiments (i.e., a bioeffective amount), one or more food materials, optional attractants, and optional wetting agents. Embodiments of the invention also include a device for controlling invertebrate pests, the device comprising the bait composition and an outer cover adapted to contain the bait composition, wherein the outer cover has at least one opening sized to allow invertebrate pests to pass through, enabling invertebrate pests to access the bait composition from a location outside the outer cover, and wherein the outer cover is also adapted to be placed in or near potential or known invertebrate pest activity areas.

[0075] Embodiments of the present invention also include a method for controlling invertebrate pests, the method comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of formula I, its N-oxide or a salt thereof (e.g., the composition described herein), provided that the method is not a method of treating a human or animal body with a drug.

[0076] The present invention also relates to methods in which the invertebrate parasitic pest or its environment is exposed to a composition comprising a biologically effective amount of a compound of formula I, its N-oxide or a salt thereof, and may further comprise additional components selected from surfactants, solid diluents and liquid diluents. The composition may also optionally comprise a biologically effective amount of at least one active ingredient (i.e., a biologically active compound or reagent), provided that the method is not a method of treating a human or animal body with a drug.

[0077] The compounds of this invention are generally used as active ingredients for controlling invertebrate pests in compositions, i.e., formulations, having at least one additional component serving as a carrier, the additional component being selected from surfactants, solid diluents, and liquid diluents. The formulation or composition components are selected to be consistent with the physical properties, application method, and environmental factors (such as soil type, humidity, and temperature) of the active ingredient.

[0078] Useful formulations include liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspensions), etc., which can optionally be thickened into gels. Aqueous liquid compositions are generally categorized as soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, and suspensions. Non-aqueous liquid compositions are generally categorized as emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.

[0079] Solid compositions are generally available in the form of powders, granules, pellets, pellets, tablets, lozenges, tablets, and filled films (including seed coatings), and can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredients can be encapsulated (micro)capsules and further formed into suspensions or solid formulations; alternatively, the entire active ingredient formulation can be encapsulated (or “coated”). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrates and dry granule formulations. High-concentration compositions are primarily used as intermediates for other formulations.

[0080] Sprayable formulations are typically dispersed in a suitable medium before spraying. These liquid and solid formulations are formulated to be easily diluted in the spraying medium (usually water). Spray volumes can range from about one liter to several thousand liters per hectare, but are more typically about ten to several hundred liters per hectare. Sprayable formulations can be mixed in a trough with water or another suitable medium for foliar treatment via air or ground spraying, or applied to the plant's growing medium. Liquid and dry formulations can be directly metered into drip irrigation systems or metered into furrows during planting. Liquid and solid formulations can be applied to the seeds of crops and other desired plants as part of pre-planting seed treatment to protect developing roots and other underground plant parts and / or leaves through systemic absorption.

[0081] The formulation will typically contain effective amounts of active ingredient, diluent, and surfactant, which, in the approximate range below, total 100% by weight.

[0082] Solid diluents include, for example, clays such as bentonite, montmorillonite, palygorskite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g. lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate.

[0083] Liquid diluents include, for example, water, N,N-dimethylalkanamide (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidone (e.g., N-methylpyrrolidone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butyl carbonate, paraffin (e.g., white mineral oil, n-alkanes, isoalkanes), alkylbenzenes, alkylnaphthalenes, glycerol, triacetylglycerol, sorbitol, aromatics, dearomatized aliphatic compounds, alkylbenzenes, alkylnaphthalenes, ketones (e.g., cyclohexanone, 2-heptanone, isophorone, and 4-hydroxybenzene), etc. The diluent may contain 4-methyl-2-pentanone, acetates (such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate), other esters (such as alkyl lactates, diesters, and γ-butyrolactone), and may be straight-chain, branched, saturated, or unsaturated alcohols (such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecanol, isoctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, and benzyl alcohol). Liquid diluents may also include saturated and unsaturated fatty acids (typically C6-C). 22 Glycerides of plant seeds and fruits (e.g., olive oil, castor oil, flaxseed oil, sesame oil, corn oil, peanut oil, sunflower oil, grapeseed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, coconut oil, and palm kernel oil), animal fats (e.g., beef tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated (e.g., methylated, ethylated, butylated) fatty acids, wherein the fatty acids can be obtained by hydrolysis of glycerides derived from plants and animals and can be purified by distillation.

[0084] The solid and liquid compositions of the present invention typically contain one or more surfactants. When added to a liquid, the surfactant (also referred to as a "surface-active agent") typically alters, most commonly by reducing the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, the surfactant can be used as a wetting agent, dispersant, emulsifier, or defoamer.

[0085] Surfactants can be classified as nonionic, anionic, or cationic surfactants. Nonionic surfactants that can be used in this composition include, but are not limited to: alcohol alkoxylates, such as those based on natural and synthetic alcohols (which are branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butane oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkylphenol alkoxylates, such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonylphenol ethoxylates, and dodecylphenol ethoxylates (prepared from phenol and ethylene oxide, propylene oxide, butane oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers wherein the terminal blocks are prepared from propylene oxide; ethoxylated... Ethoxylated fatty acids; ethoxylated aliphatic esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butane oxide, or mixtures thereof); fatty acid esters, glycerides, lanolin-based derivatives, polyethoxylated esters, such as polyethoxylated sorbitol fatty acid esters, polyethoxylated sorbitan fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitol derivatives, such as sorbitol esters; polymeric surfactants, such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, grafted or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives, such as sucrose esters, alkyl polyglucosides, and alkyl polysaccharides.

[0086] Available anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohols or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives, such as lignin sulfonates; maleic acid or succinic acid or their anhydrides; olefin sulfonates; phosphate esters, such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfates; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides, such as N,N-alkyl taurine; sulfonates of benzene, isopropylbenzene, toluene, xylene, and dodecylbenzene and tridecylbenzene; sulfonates of condensed naphthalene; sulfonates of naphthalene and alkylnaphthalene; sulfonates of petroleum fractions; sulfosuccinates; and sulfosuccinates and their derivatives, such as dialkylsulfosuccinates.

[0087] Available cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines, such as N-alkylpropylenediamine, tripropylenetriamine and dipropylenetetraamine, as well as ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butyl oxide or mixtures thereof); amine salts, such as amine acetates and diamine salts; quaternary ammonium salts, such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides, such as alkyldimethylamine oxides and di-(2-hydroxyethyl)-alkylamine oxides.

[0088] The compositions that can also be used in this invention are mixtures of nonionic surfactants and anionic surfactants, or mixtures of nonionic surfactants and cationic surfactants.

[0089] The compositions of the present invention may also contain formulation adjuvants and additives known to those skilled in the art as auxiliary formulations (some of which may also be considered as solid diluents, liquid diluents, or surfactants). Such formulation adjuvants and additives can control: pH (buffers), foaming during processing (defoamers, such as polysiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), microbial growth within the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), elution (film-forming agents or binders), evaporation (anti-evaporation agents), and other formulation properties. Film-forming agents include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes.

[0090] Compounds of Formula I and any other active ingredients are typically incorporated into the compositions of the present invention by dissolving the active ingredient in a solvent or by milling the active ingredient in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of the liquid composition used as an emulsifiable concentrate is immiscible with water, an emulsifier is typically added to emulsify the solvent containing the active ingredient when diluted with water. A media mill can be used to wet-mill slurries of active ingredients with a particle size of up to 2,000 μm to obtain particles with an average diameter of less than 3 μm. Aqueous slurries can be prepared as finished suspension concentrates (see, for example, US 3,060,084) or further processed into particles that are dispersible in water by spray drying. Dry formulations typically require a dry milling step, which produces an average particle size in the range of 2 to 10 μm. Powders and granules can be prepared by mixing, typically by milling (e.g., with a hammer mill or hydrodynamic mill). Particles and granules can be prepared by spraying the active material onto a pre-formed particle carrier or by agglomeration techniques.

[0091] The compounds of this invention exhibit broad-spectrum activity against invertebrate pests. These pests include invertebrates inhabiting a variety of environments such as plant leaves, roots, soil, harvested crops or other food, buildings, or animal fur. These pests include, for example, invertebrates that feed on leaves (including leaf blades, stems, flowers, and fruits), seeds, wood, textile fibers, or animal blood or tissues, and that cause damage or harm to, for example, growing or stored crops, forest crops, greenhouse crops, ornamental plants, nursery crops, stored food or fiber products, or housing or other structures or their contents, or are harmful to animal or public health. Those skilled in the art will appreciate that not all compounds have the same effect on all pests throughout their entire growth stage.

[0092] Therefore, these compounds and compositions of the present invention can be used agronomically to protect field crops from phytophagous invertebrate pests, and also non-agronomically to protect other horticultural crops and plants from phytophagous invertebrate pests. This use includes protecting crops and other plants (i.e., agronomical and non-agronomical) from genetic material introduced through genetic engineering (i.e., transgenics) or mutagenesis to provide advantageous traits. Examples of such traits include herbicide tolerance, tolerance to phytophagous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant pathogenic fungi, bacteria, and viruses), improved plant growth, enhanced tolerance to adverse growing conditions (such as high or low temperatures, low or high soil moisture, and high salinity), increased flowering or fruiting, increased yield, faster maturity, higher quality and / or nutritional value of the harvested product, or improved storage or processing properties of the harvested product. Transgenic plants can be modified to express a variety of traits. Examples of plants containing characteristics provided by genetic engineering or mutagenesis include various maize, cotton, soybean, and potato plants that express insecticidal Bacillus thuringiensis toxins, such as YIELD. and And various herbicide-resistant corn, cotton, soybeans, and rapeseed, such as ROUNDUP LIBERTY

[0093] and This includes crops expressing N-acetyltransferase (GAT) to provide resistance to glyphosate herbicides, or crops containing the HRA gene to provide resistance to herbicides, and crops that inhibit acetyllactate synthase (ALS). The compounds and compositions of the present invention can synergistically interact with traits introduced by genetic engineering or mutagenesis to enhance the phenotypic expression or effect of the traits, or to enhance the invertebrate pest control efficacy of the compounds and compositions of the present invention. Specifically, the compounds and compositions of the present invention can synergistically interact with the phenotypic expression of proteins or other natural products toxic to invertebrate pests to provide a greater than additive control effect against these pests.

[0094] The compositions of the present invention may optionally contain phytonutrients, such as fertilizer compositions containing at least one phytonutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum. It is noteworthy that compositions containing at least one fertilizer composition contain at least one phytonutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, and magnesium. Compositions of the present invention that also contain at least one phytonutrient may be in liquid or solid form. Solid formulations in granule, stick, or tablet form are noteworthy. Solid formulations containing fertilizer compositions are prepared by mixing the compounds or compositions of the present invention with fertilizer compositions and formulation ingredients, and then preparing the formulation by methods such as granulation or extrusion. Alternatively, solid formulations are prepared by spraying a solution or suspension of the compounds or compositions of the present invention in a volatile solvent onto a previously prepared, size-stable mixture of fertilizer compositions (e.g., granules, sticks, or tablets), and then evaporating the solvent.

[0095] Examples of agronomical or non-agronomical invertebrate pests include the eggs, larvae, and adults of lepidopteran pests, such as armyworms, caterpillars, inchworms, and bollworms (e.g., the corn borer (Sesamia inferens Walker)).

[0096] (Sesamia nonagrioides Lefebvre), Southern Grey-winged Armyworm (Spodoptera eridania Cramer), Fall Armyworm (Spodoptera frugiperda JESmith), Beetworm (Spodoptera exigua Hübner), Cotton Leafworm

[0097] (Spodoptera littoralis Boisduval), Yellow-banded armyworm (Spodoptera ornithogalli Guenée), Small cutworm

[0098] (Agrotis ipsilon Hufnagel), Bean-earworm (Anticarsia gemmatalis Hübner), Green-fruited moth

[0099] (Lithophane antennata Walker), Cabbage looper (Barathra brassicae Linnaeus), Soybean looper

[0100] (Pseudoplusiaincludens Walker), cabbage looper (Trichoplusia ni Hübner), tobacco aphid (Heliothis virescens Fabricius)); borers, sheath moths, web-forming caterpillars, pine cone leafminer, cabbage caterpillar, and leaf-carving insects from the Pyralidae family (such as European corn borer (Ostrinia nubilalis Hübner), navel orange borer (Amyeloistransitella Walker), corn root borer (Crambus caliginosellus Clemens), and grass moths (Pyralidae: Pyralinae), such as rice leaf cutter moth (Herpetogramma licarsisalis Walker), sugarcane two-spotted borer (Chiloinfuscatellus Snellen), tomato small borer (Neoleucinodes elegantalis Guenée), and rice leaf roller (Cnaphalocrocis) medinalis, grape leaf borer (Desmia funeralis Hübner), melon moth

[0101] (Diaphania nitidalis Stoll), cabbage core grub (Hellula hydralis Guenée), rice stem borer (Scirpophaga incertulas Walker), seedling borer (Scirpophaga infuscatellus Snellen), white borer (Scirpophaga innotata Walker), top seedling borer (Scirpophaganivella Fabricius), rice leaf borer (Chilo polychrysus Meyrick), cabbage tuft caterpillar (Crocidolomia binotalis zeller); leafrollers, aphids, seed worms, and fruit moths of the leafroller family (such as apple leafroller (Cydia pomonella Linnaeus), grape berry moth).

[0102] (Endopiza viteana Clemens), Pear Fruit Moth (Grapholita molesta Busck), Apple Leaf Roller (Cryptophlebia leucotreta Meyrick), Citrus Borer (Ecdytolophaaurantiana Lima), Red-banded Leaf Roller (Argyrotaenia velutinana Walker), Rose-banded Leaf Roller (Choristoneura rosaceana Harris), Apple Light Brown Leaf Roller (Epiphyas postvittana Walker), Privet Leaf Roller (Eupoecilia ambiguella Hübner), Apple Terminal Leaf Roller (Pandemis pyrusana Kearfott), Omnivorous Leaf Roller (Platynota stultana Walsingham), Striped Fruit Tree Leaf Roller (Pandemiscerasana Hübner), Apple Brown Leaf Roller

[0103] (Pandemis heparana Denis et Schiffermüller)); and many other economically important Lepidoptera (such as the diamondback moth (Plutella xylostella Linnaeus), the cotton bollworm (Pectinophora gossypiella Saunders), and the gypsy moth).

[0104] (Lymantria dispar Linnaeus), peach fruit moth (Carposina niponensis Walsingham), peach stripe moth (Anarsia lineatella Zeller), potato tuber moth (Phthorimaea operculella Zeller), spotted leaf miner (Lithocolletis blancardella Fabricius), apple golden leafminer (Lithocolletis ringoniella Matsumura), rice leaf roller (Lerodea eufala Edwards), spiral leafminer (Leucoptera scitella Zeller)); eggs, pupae, and adults of Blattodea, including cockroaches from Blattidae and Blattodea families (such as Oriental cockroach (Blatta orientalis Linnaeus), Asian cockroach (Blatella asahinai Mizukubo), German cockroach (Blattella germanica Linnaeus), and brown-banded cockroach).

[0105] *Supella longipalpa Fabricius*, *Periplaneta americana* Linnaeus, *Periplaneta brunnea* Burmeister, *Leucophae amadeera* Fabricius; *Periplaneta fuliginosa* Service, *Periplaneta australasiae* Fabr., *Nauphoeta cinerea* Olivier, and *Symploce pallens* Stephens; larvae and adults of Coleoptera raised on eggs, leaves, fruits, roots, seeds, and vesicles, including weevils from the families Longhorn weevils, Bean weevils, and Cressidae (such as the cottonseed weevil *Anthonomus grandis* Boheman and the rice water weevil).

[0106] (Lissorhoptrus oryzophilus Kuschel), Sitophilus granariusLinnaeus, rice elephant

[0107] (Sitophilus oryzae Linnaeus)); *Listronotus maculicollis Dietz*, *Sphenophorus parvulus Gyllenhal*, *Sphenophorus venatus vestitus*, *Sphenophorus cicatristriatus Fahraeus*; flea beetles, melon beetles, root beetles, leaf beetles, potato beetles, and leaf miners (such as the Colorado potato beetle (Leptinotarsadecemlineata Say) and the western corn root beetle (Diabrotica virgifera virgifera LeConte)); scarab beetles and other beetles from the Scarabaeidae family (such as the Japanese scarab beetle (Popillia japonica Newman), the Oriental scarab beetle (Anomala orientalis Waterhouse, Exomala orientalis (Waterhouse) Baraud), and the northern rhinoceros beetle (Cyclocephala borealis). Arrow, Southern rhinoceros beetle (Cyclocephala immaculata Olivier or C. Lurida Bland), dung beetle and grub (Aphodius), black scarab beetle (Ataenius spretulus Haldeman), green scarab beetle (Cotinis nitida Linnaeus), chestnut velvet scarab beetle

[0108] (Maladera castanea Arrow), May / June scarab beetle (Phyllophaga genus) and European scarab beetle (Rhizotrogus majalis Razoumowsky)); Dermestididae dermestid beetles; Click beetles nematodes; Bark beetles of the Bark Beetle family and Tenebrionid beetles.

[0109] In addition, agricultural and non-agricultural pests include: eggs, adults, and larvae of Dermaptera, including earwigs of the family Earwigidae (such as the European ball earwig (Forficula auricularia Linnaeus) and the black earwig (Chelisoches morio Fabricius)); eggs, immature bodies, adults, and pupae of Hemiptera and Homoptera, such as mirid bugs of the family Mirididae, cicadas of the family Cicadidae, leafhoppers (such as those of the genus Empoasca), and bedbugs of the family Cimex (such as Cimex lectularius). Linnaeus, planthoppers (Fishhoppers and rice planthoppers), treehoppers (Cestridae), psyllids (Psyllidae), whiteflies (Whiteflies), aphids (Aphididae), root aphids (Root aphids), mealybugs (Mealybugs), scale insects (Scale insects), scaly scale insects (Scale insects), lace bugs (Lycticephalopods), stink bugs (Stink bugs), long bugs (Sorghum long bugs, such as hairy long bugs (Blissus leucopterus hirtus Montandon) and southern wheat bugs (Blissus insularis Barber)) and other long bugs (Lycticephalopods), grasshoppers (Lycticephalopods), cucurbit grasshoppers (Cucurbit grasshoppers), and red bugs (Red bugs and cotton bollworms).

[0110] Agricultural and non-agricultural pests also include: eggs, larvae, pupae, and adults of mites (such as spider mites and red spider mites in the family Tetranychus (e.g., apple red spider mite (Panonychus ulmi Koch), two-spotted spider mite (Tetranychus urticae Koch), and McDanieli spider mite (Tetranychus mcdanieli McGregor)); grape mites in the family Aphididae (e.g., citrus red spider mite (Brevipalpus lewisi McGregor)); rust ticks and bud ticks in the family Eriophyridae, as well as other leaf-feeding mites and mites important to human and animal health, namely dust mites in the family Epidermophyridae, Demodex mites in the family Demodex, and grain mites in the family Aphididae; and ticks commonly known as hard ticks in the family Ixodidae (e.g., deer tick (Ixodes scapularis Say) and Australian paralyzed tick).

[0111] (Ixodes holocyclus Neumann), American dog tick (Dermacentor variabilis Say), Lone Star tick

[0112] (Amblyomma americanum Linnaeus) and ticks of the family Cryptorchididae, commonly known as soft ticks (e.g., relapsing fever tick (Ornithodoros turicata), common chicken tick (Argas radiatus)); itch mites and scabies mites of the families Ophiopogonidae, Pyratidae, and Sarcoptera; eggs, adults, and immature bodies of Orthoptera, including grasshoppers, locusts, and crickets (e.g., migratory grasshoppers (e.g., blood locust, special locust Thomas), American grasshoppers (e.g., Schistocerca americana Drury), desert locusts (Schistocerca gregaria Forskal), migratory locusts (Locusta migratoria Linnaeus), dwarf tree locusts (Zonocerus), house crickets (Acheta domesticus Linnaeus), mole crickets (e.g., yellow mole cricket (Scapteriscus vicinus Scudder) and South American mole crickets (Scapteriscus borellii)). Giglio-Tos); eggs, adults, and immature bodies of Diptera, including leaf miners (such as leaf miners of the genus *Liriomyza sativae* Blanchard); midges, fruit flies (Fungidae), bleat flies (such as rye straw flies), dung beetles, common houseflies (such as house flies), and summer toilet flies (such as summer toilet flies, *F. femoralis*). Stein, stable flies (such as stable stinging flies), cow flies, horn flies, blowflies (such as golden fly and black fly) and other housefly pests, horseflies (such as horseflies), strychnine flies (such as stomach flies and mad flies), cow flies (such as cow flies), deer flies (such as spotted flies), sheep tick flies (such as sheep lice flies) and other short-horned flies; mosquitoes (such as Aedes, Anopheles, and Culex), black flies (such as black flies), midges, sandflies, fungus gnats and other longhorned flies; eggs, adults, and immature bodies of Thysanoptera, including onion thrips (Thrips tabaci Lindeman), flower thrips (Thrips genus) and other leaf-feeding thrips; insect pests of Hymenoptera, including ants of the Formicidae family, including Camponotus floridanus Buckley and Camponotus ferrugineus. Fabricius, Black Wood Worker Ant (Camponotus pennsylvanicus DeGeer), White-footed Stink Ant

[0113] *Technomyrmex albipes fr. Smith*, large-headed ant (*Pheidole* genus), black-headed sour ant (*Tapinoma melanocephalum Fabricius*); Pharaoh ant (*Monomorium pharaonis Linnaeus*), small fire ant (*Wasmannia auropunctata Roger*), fire ant (*Solenopsis geminata Fabricius*), invasive red imported fire ant (*Solenopsis invicta Buren*), Argentine ant (*Iridomyrmex humilis Mayr*), crazy ant

[0114] (Paratrechina longicornis Latreille), pavement ant (Tetramorium caespitumLinnaeus), corn ant (Lasius alienus) ) and stink bug (Tapinoma sessile Say). Other hymenoptera include bees (including carpenter bees), giant hornets, wasps, and sawflies (Neodiprion; Cephus); isoptera insect pests include termites (such as the genus *Odontotermes obesus* Rambur), wood termites (such as the genus *Coprinus*), and rhinoceros termites (such as the genera *Reticulitermes*, *Reticulitermes*, *Reticulitermes dabieshanensis*), *Reticulitermes kollar*, *Reticulitermes banksiae*, *Coptotermes formosanus* Shiraki, and *Coptotermes formosanus*.

[0115] (Incisitermes immigrans Snyder), powdery termite (Cryptotermes brevis Walker), drywood termite

[0116] (Incisitermes snyderi Light), southeastern subterranean termites (Reticulitermes virginicus Banks), drywood termites (Incisitermes minor Hagen), arboreal termites such as *Incisitermes* and other economically important termites; insect pests of the order Thysanura, such as silverfish (Lepisma saccharina Linnaeus) and house silverfish.

[0117] (Thermobia domestica Packard); insect pests of the order Trichophyton, including head lice.

[0118] (Pediculus humanus capitis De Geer), body lice (Pediculus humanus Linnaeus), chick feather lice

[0119] (Menacanthus stramineus Nitszch), dog lice (Trichodectes canis De Geer), hairy lice

[0120] (Goniocotes gallinae De Geer), sheep lice (Bovicola ovis Schrank), cattle blind lice (Haematopinus eurysternus Nitzsch), long-nosed livestock lice (Linognathus vituli Linnaeus), and other sucking and chewing lice that attack humans and animals; flea insect pests, including the Oriental mouse flea.

[0121] (Xenopsylla cheopis Rothschild), cat flea (Ctenocephalides felis Bouche), dog flea

[0122] (Ctenocephalides canis Curtis), chicken flea (Ceratophyllus gallinae Schrank), sucker flea (Echidnophaga gallinacea Westwood), human flea (Pulex irritans Linnaeus), and other fleas that cause suffering to mammals and birds. Additional arthropod pests include: spiders such as the brown hermit spider (Loxosceles reclusa Gertsch & Mulaik) and the black widow spider (Latrodectus mactans Fabricius), and centipedes such as the house centipede (Scutigera coleoptrata Linnaeus).

[0123] Examples of invertebrate pests affecting stored grains include the large grain beetle (Prostephanus truncatus), the small grain beetle (Rhyzopertha dominica), the rice weevil (Sitophilus oryzae), the corn weevil (Sitophilus zeamais), the cowpea weevil (Callosobruchus maculatus), the red flour beetle (Tribolium castaneum), the grain weevil (Sitophilus granarius), the Indian meal borer (Plodia interpunctella), the Mediterranean face weevil (Ephestia kuhniella), and the long-horned flat flour beetle or the rusty red flat flour beetle (Cryptolestes ferrugineus).

[0124] The compounds of this invention exhibit particularly high activity against the following lepidopteran pests (e.g.

[0125] *Alabama argillacea* Hübner (clothes moth), *Archips argyrospila* Walker (fruit tree leaf roller), *A. rosana* Linnaeus (European leaf roller), and other species of the genus *Alabama*, *Chilo suppressalis* Walker (rice stem borer), *Cnaphalocrocis medinalis* Guenée (rice leaf roller), *Crambus caliginosellus* Clemens (corn root webbing caterpillar), *Crambus teterrellus* Zincken (blue grass moth), *Cydia pomonella* Linnaeus (apple leaf roller), *Earias insulana* Boisduval (diamond borer), *Earias vittella* Fabricius (green bollworm), *Helicoverpa armigera* Hübner (American bollworm), *Helicoverpa zea* Boddie (cotton bollworm), *Heliothis virescens* Fabricius (tobacco aphid), *Herpetogramma licarsisalis* Walker (grass moth), Lobesia botrana Denis & Schiffermüller (grape berry moth)

[0126] Pectinophora gossypiella Saunders (cotton bollworm), Phyllocnistis citrella Stainton (citrus leaf miner), Pieris brassicae Linnaeus (cabbage white butterfly), Pieris rapae Linnaeus (cabbage white moth), Plutella xylostella Linnaeus (diamond moth), Spodoptera exigua Hübner (beet armyworm), Spodoptera litura Fabricius (striped beet armyworm), Spodopterafrugiperda JESmith (early fall armyworm), Trichoplusia ni Hübner (cabbage silver striped armyworm), and Tutaabsoluta Meyrick (tomato leafminer).

[0127] The compounds of this invention also exhibit significant activity in members of the order Hemiptera, including: *Acyrthosiphon pisum Harris* (bean aphid), *Aphis craccivora Koch* (black bean aphid), *Aphisfabae Scopoli* (broad bean aphid), *Aphis gossypii Glover* (cotton aphid, melon aphid), *Aphis pomi De Geer* (apple aphid), *Aphis spiraecola Patch* (leaf-rolling aphid), *Aulacorthum solani Kaltenbach* (eggplant aphid), *Chaetosiphon fragaefolii Cockerell* (strawberry aphid), *Diuraphis noxia Kurdjumov / Mordvilko* (Russian wheat aphid), *Dysaphis plantaginea Paaserini* (red apple aphid), *Eriosomalanigerum Hausmann* (cotton apple aphid), *Hyalopterus pruni Geoffroy* (peach aphid), *Lipaphiserysimi Kaltenbach* (radish aphid), and *Metopolophium dirhodum*. Walker (wheat aphid), Macrosiphumeuphorbiae Thomas (potato aphid), Myzus persicae Sulzer (peach aphid), Nasonoviaribisnigri Mosley (lettuce aphid), Pemphigus (root aphids and thrips aphids), Rhopalosiphum maidis Fitch (corn leaf aphid), Rhopalosiphum padi Linnaeus (grain overflow aphid), Schizaphis graminum Rondani (wheat two-forked aphid), Sitobion avenae Fabricius (wheat long-tube aphid), Therioaphis maculata Buckton (alfalfa spotted aphid), Toxoptera aurantii Boyer de Fonscolombe (orange two-forked aphid) and Toxoptera citricida Kirkaldy (brown orange aphid); Adelges (ball aphid);

[0128] Phylloxera devastatrix Pergande (Pecan phylloxera); Bemisia tabaci Gennadius (Tobacco whitefly, sweet potato whitefly), Bemisia argentifolii Bellows & Perring (Silver leaf whitefly), Dialeurodes citri Ashmead (Citrus whitefly), and Trialeurodes vaporariorum Westwood (Greenhouse whitefly); Empoasca fabae Harris (Potato green leafhopper), Laodelphax striatellus Fallen (Grey planthopper)

[0129] Macrosteles quadrilineatus Forbes (two-spotted leafhopper), Nephotettix cincticepsUhler (green leafhopper), Nephotettix nigropictus (Black-tailed Leafhopper), Nilaparvata lugens (Brown planthopper), Peregrinus maidis Ashmead (corn planthopper), Sogatella furcifera Horvath (white-backed planthopper), Sogatodes orizicola Muir (rice planthopper), Typhlocyba pomaria McAtee, white appleleafhopper, Erythroneura (grape leafhopper); Magicicada septendecim Linnaeus (periodic planthopper);

[0130] Icerya purchasi Maskell (cotyledonous scale insect), Quadraspidiotus perniciosus Comstock (Saint Joseph's insect); Planococcus citri Risso (citrus mealybug); Pseudococcus (other mealybug complexes);

[0131] Cacopsylla pyricola Foerster (pear psyllid), Trioza diospyri Ashmead (persimmon psyllid).

[0132] The compounds of the present invention are also active in members derived from the order Hemiptera, which includes:

[0133] Acrosternum hilare Say (rice green bug), Anasa tristis De Geer (pumpkin bug), Blissus leucopterus leucopterus Say (sorghum bug), Cimex lectularius Linnaeus (bed bug), Corythucha gossypii Fabricius (cotton web bug), Cyrtopeltis modesta Distant (tomato bug), Dysdercus suturellus Herrich-

[0134] (Soil weevil), Euchis servus Say (brown stink bug), Euchis variolarius Palisot de Beauvois (spotted stink bug), Graptostethus (long bug synod), Leptoglossuscorculus Say (leaf root pine nut bug), Lygus lineolaris Palisot de Beauvois (pasture mirid bug), Nezara viridula Linnaeus (southern green rice bug), Oebalus pugnax Fabricius (rice brown bug), Oncopeltus fasciatus Dallas (large milkweed long bug), Pseudatomoscelis seriatus Reuter (cotton mirid bug). Other insect orders controlled by the compounds of this invention include Thysanoptera (such as Frankliniella occidentalis Pergande, Scirthothrips citri Moulton, Sericothripsvariabilis Beach, and Thrips tabaci Lindeman); and Coleoptera (such as Leptinotarsa ​​decemlineata Say, Epilachna varivestis Mulsant, and Agriotes, Athos, or Limonius (nematodes)).

[0135] The compounds of this invention are also active against members of the classes Nematodes, Cesium, Trematodes, and Acanthocephalans, including members of the orders Strongyloides, Ascarids, Acromura, Micrococcus, Spiralura, and Spurula, which are of economic importance. These include, but are not limited to, economically important agricultural pests (i.e., root-knot nematodes, root-rot nematodes, and stump nematodes, etc.) and pests that harm animal and human health (i.e., all economically important trematodes, tapeworms, and ascarids, such as *Strongyloides vulgaris* in horses, *Toxocara canis* in dogs, *Haemaphysalis contortus* in sheep, *Filaria canis* in dogs, *Naja lobata* in horses, and *Fasciola hepatica* in ruminants).

[0136] It should be noted that some modern classification systems categorize Homoptera as a suborder of Hemiptera.

[0137] It is noteworthy that the compounds of the present invention are useful in controlling the potato green leafhopper (Empoasca fabae). It is noteworthy that the compounds of the present invention are useful in controlling the corn lanternfly (Peregrinus maidis). It is noteworthy that the compounds of the present invention are useful in controlling the cotton aphid (Aphis gossypii). It is noteworthy that the compounds of the present invention are useful in controlling the peach aphid (Myzus persicae). It is noteworthy that the compounds of the present invention are useful in controlling the diamondback moth (Plutella xylostella). It is noteworthy that the compounds of the present invention are useful in controlling the fall armyworm (Spodoptera frugiperda).

[0138] It is worth noting the use of the compounds of the present invention in controlling the southern green rice bug (Nezara viridula), the bean pod mirid bug (Lygus hesperus), the rice water weevil (Lissorhoptrus oryzophilus), the brown planthopper (Nilaparvatalugens), the two-spotted black-tailed leafhopper (Nephotettix virescens), and the rice stem borer (Chilo suppressalis).

[0139] The compounds of the present invention can be mixed with one or more other active ingredients to form multi-component insecticides, providing even broader agronomic and non-agronomic uses. These active ingredients (i.e., biologically active components or reagents) include insecticides, fungicides, nematicides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulants, chemical sterilizers, chemical pheromones, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds, or insect-pathogenic bacteria, viruses, or fungi. Therefore, the present invention also relates to compositions consisting of a biologically effective amount of a compound of formula I, its N-oxide or a salt thereof, at least one formulation adjuvant, and at least one other active ingredient or reagent, said formulation adjuvant being selected from surfactants, solid diluents, and liquid diluents. With regard to the mixtures of the present invention, other active ingredients or reagents may be formulated together with the compounds of the present invention (including compounds of formula I) to form a premix, or other biologically active compounds or reagents may be formulated separately with the compounds of the present invention (including compounds of formula I) and the two formulations may be mixed together before application (e.g., in a spray can), or the two formulations may be applied sequentially.

[0140] Examples of such biologically active compounds or reagents that can be formulated from the compounds of the present invention are insecticides such as abamectin, chlorpyrifos, fenpropathrin, acetamiprid, flufenoxuron, sulfadiazine, amitraz, avermectin, azadirachtin, methyl glutathione, chlorfenapyr, bifenthrin, bifenazate, diflubenzuron, borate, pymetrozine, thion, carbaryl, carbofuran, fenitrothion, chlorantraniliprole, brofenoxuron, difenoconazole, chlorpyrifos, methyl chlorpyrifos, fenpropathrin, chlorfenapyr, chlorfenapyr, chlorpyrifos, chlorfenapyr ... Cypermethrin, γ-trifluorocypermethrin, λ-trifluorocypermethrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cypermethrin, deltamethrin, difenoconazole, dichlorvos, dichlorvos, tetrafluoromethrin, cartap, dimethoate, fipronil, diphenylpropyl ether, emamectin benzoate, endosulfan, cis-cypermethrin, acetamiprid, permethrin, etoxazole, fenbutatin, fenthiocarb, fenoxycarb, cypermethrin, fenvalerate, fipronil, flupyradifurone, flufenoxuron, flufenoxuron, pyrimethanil, flufenoxuron, lambda-cyhalothrin, t-flufenoxuron, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil Thiazophos, chlorfenapyr, flufenoxuron, thiamethoxam, flufenoxuron, imidacloprid, indoxacarb, insecticidal soap, isofenphos, lufenuron, malathion, chlorfluazuron, cyfluthrin, snailicide, methamidophos, chlorpyrifos, methomyl, acetamiprid, methoxyprofen, methoxydichlorophenoxyacetic acid, methoxyfenozide, acetamiprid, nitrazepam, diphenylfluorourethane, polyflufenocyanurate, glufosinate, parathion, methyl parathion, phorate, phorate, phosmet, phosmet, phosphamidon, pyrethroid insecticides, pyrethroids, pymetrozine Ketones, pyrethroids, flufenoxuron, pyrethroids, pyridaben, acetamiprid, neoquinazoline insecticides, pyridaben, fenpropathrin, rotenone, leonine, carbendazim, spinosad, tebufenozide, spirotetramat, thiophanate-methyl, flufenoxuron, tebufenozide, pyridaben, fenpropathrin, fenpropathrin, terbufenozide, chlorpyrifos, pyrethroids, pyrethroids, pyrethroids, tetrafluoroethylene, thiamethoxam, thiamethoxam, methomyl, chlorpyrifos, fenpropathrin, pyrethroids, trichlorfon, chlorfenapyr, Bacillus thuringiensis δ-endotoxin, insect pathogenic bacteria, insect pathogenic viruses, and insect pathogenic fungi.

[0141] It is worth noting insecticides such as abamectin, acetamiprid, flufenoxuron, amitraz, avermectin, azadirachtin, chlorfenapyr, bifenthrin, pymetrozine, thion, carbaryl, fenitrothion, chlorantraniliprole, brofenoxuron, chlorpyrifos, chlorfenapyr, fenpropathrin, chlorfenapyr, cypermethrin, β-cypermethrin, deltamethrin, γ-cypermethrin, λ-cypermethrin, cypermethrin, α-cypermethrin, ζ-cypermethrin, cypermethrin, deltamethrin, dichlorvos, diphenylpropyl ether, emamectin benzoate, endosulfan, cis-cypermethrin, acetamiprid, ethoxyfenozide, etoxazole, fenthiocarb, fenoxycarb, cypermethrin, fipronil, and flufenoxuron. The following are included: chlorfenapyr, flufenoxuron, flufenoxuron, lambda-cyhalothrin, thiamethoxam, flufenoxuron, flufenoxuron, imidacloprid, indoxacarb, lufenuron, cyfluthrin, methomyl, ethoxyfenozide, methoxyfenozide, acetamiprid, nifedipine, diphenylfluorouracil, glufosinate, pymetrozine, pyridaben, acetamiprid, fenpyroximate, carbendazim, spinosad, tebufenozide, spirodiclofen, tebufenozide, pyrethroids, thiamethoxam, methomyl, chlorpyrifos, tetrabromopyrethrin, pyrethroids, all strains of Bacillus thuringiensis δ-endotoxin, all strains of Bacillus thuringiensis, and all strains of nucleopolyhedrovirus.

[0142] One embodiment of a biological agent for mixing with the compounds of the present invention includes insect pathogenic bacteria such as Bacillus thuringiensis, and capsule-encapsulated Bacillus thuringiensis δ-endotoxin such as that derived from... Prepared by method and Biological pesticides ( and (This is a trademark of Mycogen Corporation (Indianapolis, Indiana, USA)); entomopathogenic fungi such as Metarhizium anisopliae; and entomopathogenic (natural and genetically modified) viruses, including baculoviruses, nucleopolyhedroviruses (NPVs) such as the cornworm nucleopolyhedrovirus (HzNPV) and the celery worm nucleopolyhedrovirus (AfNPV); and granuloviruses (GVs) such as the codling moth granulovirus (CpGV).

[0143] Of particular note is that other invertebrate pest control active ingredients belong to a different chemical class or have a different site of action than the compound of Formula I. In some cases, combination with at least one other invertebrate pest control active ingredient having a similar range of control but a different site of action is particularly advantageous for resistance management. Therefore, the compositions of the present invention may further comprise a biologically effective amount of at least one additional invertebrate pest control active ingredient having a similar range of control but belonging to a different chemical class or having a different site of action. These additional biologically active compounds or agents include, but are not limited to, sodium channel modulators such as bifenthrin, cypermethrin, deltamethrin, lambda-cyhalothrin, λ-cypermethrin, deltamethrin, β-cypermethrin, deltamethrin, tetramethrin, cis-cypermethrin, cypermethrin, indoxacarb, methoxyfenozide, propofol, pyrethroids, and tetrabromofenozide; cholinesterase inhibitors such as chlorpyrifos, ethoxyphos, glufosinate, and thiophanate-methyl. Methomyl and azoxystrobin; neonicotinoids, such as acetamiprid, conidine, dinotefuran, imidacloprid, nitrazepam, thiamethoxam, and thiamethoxam; insecticidal macrolides, such as carbendazim, spinosad, abamectin, avermectin, and emamectin benzoate; GABA (γ-aminobutyric acid) regulated chlorine channel antagonists such as avermectin, or blockers such as acetamiprid and fipronil; chitin synthesis inhibitors such as pymetrozine, cypermethrin, and fipronil. Urea, flufenoxuron, lufenuron, diphenylfluorourea, polyflufenoxuron, and chlorfenapyr; juvenile hormone analogs such as diphenylpropyl ether, phenoxycarb, methoxyprotein, and fenfluridine; octopamine receptor ligands such as amitraz; ecdysone inhibitors and ecdysone agonists such as azadirachtin, methoxyfenozide, and tebufenozide; ryanodine receptor ligands such as leanodine, and aminosanthin diamides such as chlorantraniliprole, cyantraniliprole, and flufenoxuron; nereistoxin analogs such as fenitrothion; mitochondria Electron transport inhibitors such as bromfenac, flufenoxuron, and pyridaben; lipid biosynthesis inhibitors such as tebufenozide and spirodiclofen; cyclodiene insecticides such as diethyldimethoxam or endosulfan; pyrethroids; carbamates; urea fungicides; and biological agents, including nucleopolyhedroviruses (NPVs), Bacillus thuringiensis members, encapsulated Bacillus thuringiensis delta-endotoxin, and other naturally occurring or genetically modified insecticidal viruses.

[0144] Further examples of biologically active compounds or reagents that can be formulated from the compounds of the present invention include: fungicides, such as 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] acetone, benzothiadiazole, and fenitrothion.Indazole, pendimethalin, azoxystrobin, benomyl, benomyl, benomyl, isopropyl benomyl, biphenyl, bispyrimethanil, blast fungicide-S, Bordeaux mixture (copper sulfate), boscalid / nicobifen, furazolidone, ethirimol sulfonate, dicofol, carbendazim, cymoxanil, captan, carbendazim, dimethomorph, chlorothalonil, ethoxysulfuron, clotrimazole, copper oxychloride, copper salts such as copper sulfate and copper hydroxide, cymoxanil, cycloflufenicol, cymoxanil, cyclopyridamole, pyrimethanil, cymoxanil, cymoxanil, cymoxanil, cymoxanil, cymoxanil, pyraclostrobin, pyridaben, pyridaben, chlorpyrifos, ethoxysulfuron, oxadixyl, dimethomorph, ethoxysulfuron, tebuconazole, tebuconazole-M, difenoconazole, discostrobin, dithiazoline, dodecyl ring Morpholine, styrax, econazole, eticonazole, difenoconazole, flutriafol, thiamethoxam, ethirimol, chlorpyrifos, oxadiazon, imidacloprid, chlorpyrifos, cyproconazole, valvacarb, methamidophos, cyclophosphamide, cyproconazole, seed dressing agent, benzyl benzoate, butyl morpholine, triphenyltin acetate, triphenyltin hydroxide, ferram, pyraclostrobin, fluazinam, fluazinam, fluazinam, flupyraclostrobin, fluquinazole, flusilazole, sulfadiazine, fluamide, fenazate, fluxapyroxad, captan, aluminum tris(ethyl phosphonate), tetrachlorophthalide, fenvalerate, furazolidone, forlabi, hexaconazole, hymexazol, chlorpyrifos, imazalil, methyl methazine, octyl methazine, iodocarb, succinyl methazine, isoprothiolane Net, iprodione, propineb, isoconazole, isoprothiolane, isothiazine, kasugamycin, cymoxanil, mancozeb, dimethomorph, mancozeb, pyraclostrobin, metalaxyl, cymoxanil, metalaxyl, fenaminostrobin, mancozeb, metominostrobin / fenaminostrobin, mefenoxam, benomyl, miconazole, cyproconazole, ferric ammonium methylarsine, flufenoxuron, octothiazolinone, furazolidone, oxadiazon, oxazolidinone, oxaflutole, oxaflutole, oxaflutole, oxychloride, paclobutrazol, tebuconazole, pendimethalin, pendimethalin, pyraclostrobin, isoprothiolane, phosphonic acid, phthalide, fluazinam, azoxystrobin, polyoxin, allylisothiazide, imazalil, procymidone, cymoxanil, cymoxanil Azoxystrobin hydrochloride, propiconazole, propineb, propoxyquin, prothioconazole, azoxystrobin, azoxystrobin, pyrimethanil, pyrimethanil, methomyl, nitropyrrolizin, quinolones, quinazole, fenofosmium, pentachloronitrobenzene, silthiamethoxam, siloxyfluorazole, spirocycline, streptomycin, sulfur, tebuconazole, isobutylethoxyquin, chlorpyrifos, tetrachloronitrobenzene, flufenoxuron, thiamethoxam, thiamethoxam, thiophanate-methyl, thiamethoxam, methyl thiophanate, toluenesulfonamide, triadimefon, triadimefon, pyrimethanil, azoxystrobin, tridemorph, cymoxanil, tricyclazole, azoxystrobin, cymoxanil, fenpyroxen, cymoxanil, jinggangmycin, cymoxanil, vinclozolinium, zineb, thiram, and oxadixyl; nematicides.Examples of acaricides include aldicarb, fenvalerate, glufosinate, and fenpropathrin; fungicides such as streptomycin; and acaricides such as amitraz, chlorfenapyr, chlorfenapyr, tricyclic tin, trichlorfon, chlorpyrifos, etoxazole, quinclorac, fenbutatin, cypermethrin, azoxystrobin, thiamethoxam, propargite, pyridaben, and pyridaben.

[0145] It is worth noting fungicides and compositions containing fungicides such as 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl] acetone, azoxystrobin, copper hydroxide, cymoxanil, cyclophosphamide, oxadiazon, oxadiazon, cyazofamid, azoxystrobin, flusilazole, fluamide, tetrachlorophthalide, formazan, hexaconazole, isoprothiolane, isothiazine, kasugamycin, mancozeb, fenoxystrobin, oxadiazon, pendimethalin, pyrimethanil, azoxystrobin, allylisothiazide, propiconazole, propoxyquin, quinolones, siloxystrobin, thiamethoxam, tricyclazole, azoxystrobin, and jinggangmycin.

[0146] In certain circumstances, combinations of the compounds of this invention with other bioactive compounds or agents (i.e., active ingredients), particularly those for invertebrate pest control, can yield effects greater than the sum of their parts (i.e., synergistic effects). Reducing the amount of active ingredient released into the environment while ensuring effective pest control has always been desirable. When synergistic effects of invertebrate pest-controlling active ingredients occur at application rates, conferring agronomically acceptable levels of invertebrate pest control, such combinations can be advantageously used to reduce crop product costs and environmental impact.

[0147] The compounds and compositions thereof of the present invention can be applied to plants that have been genetically modified to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis δ-endotoxin). Such application can provide broader-spectrum plant protection and can be advantageously used for resistance management. The effects of the compounds of the present invention in external application for the control of invertebrate pests can be synergistic with the expressed toxic proteins.

[0148] General references for these agronomic protectants (i.e., insecticides, fungicides, nematicides, acaricides, herbicides, and biopesticides) include “The Pesticide Manual”, 13th edition (edited by CDSTomlin, British Crop Protection Council, Farnham, Surrey, UK, 2003) and “The BioPesticide Manual”, 2nd edition (edited by LGCopping, British Crop Protection Council, Farnham, Surrey, UK, 2001).

[0149] For embodiments in which one or more of these different mixed components are used, the weight ratio of these different mixed components (total) to the compound of Formula I, its N-oxide, or a salt thereof is typically between about 1:3000 and about 3000:1. It is noteworthy that weight ratios between about 1:300 and about 300:1 are important (e.g., ratios between about 1:200 and about 200:1, between about 1:100 and about 100:1, between about 1:50 and about 50:1, between about 1:30 and about 30:1, or between about 1:5 and about 5:1). Those skilled in the art can readily determine, through simple experiments, the bioactive amount of the active ingredient required to obtain the desired range of bioactivity. Clearly, including these additional components allows for the control of invertebrate pests beyond the control range of the compound of Formula I itself.

[0150] In agricultural and non-agricultural applications, invertebrate pests are controlled by applying a biologically effective amount of one or more of the compounds of the invention, usually in the form of a composition, to pest environments, including infested agricultural and / or non-agricultural sites, to areas to be protected, or directly to pests to be controlled.

[0151] Therefore, the present invention includes a method for controlling invertebrate pests in agronomic and / or non-agronomic applications, the method comprising exposing invertebrate pests or their environment to a biologically effective amount of one or more compounds of the present invention, or to a composition comprising at least one such compound, or to a composition comprising at least one such compound and a biologically effective amount of at least one additional biologically active compound or reagent. Examples of suitable compositions comprising compounds of the present invention and a biologically effective amount of at least one additional biologically active compound or reagent include particulate compositions, wherein the additional active compound is present on particles identical to those of the compounds of the present invention, or on particles different from those of the compounds of the present invention.

[0152] An embodiment of the method of the present invention includes contacting the environment. It is noteworthy that the method in which the environment is a plant. It is also noteworthy that the method in which the environment is an animal. Furthermore, it is noteworthy that the method in which the environment is a seed.

[0153] To achieve contact with the compounds or compositions of the present invention to protect field crops from invertebrate pests, the compounds or compositions are typically applied to crop seeds before planting, to the leaves of crop plants (e.g., leaves, stems, flowers, fruits), or to the soil or other growing media before or after crop planting.

[0154] One embodiment of the contact method is by spraying. Alternatively, granular compositions containing the compounds of the present invention can be applied to plant leaves or soil. The compounds of the present invention can also be effectively delivered via plant uptake by contacting the plants with compositions containing the compounds of the present invention applied in the form of a soil soaking liquid, a granular formulation applied to the soil, a seedling tray treatment, or a transplant soak. The compositions of the present invention in the form of a soil soaking liquid are noteworthy. Methods for controlling invertebrate pests that involve contacting the invertebrate pests or their environment with a biologically effective amount of the compounds of the present invention, or with a composition containing a biologically effective amount of the compounds of the present invention, are also noteworthy. Methods in which the environment is soil and the composition is applied to the soil as a soil soaking formulation are also noteworthy. It is also noteworthy that the compounds of the present invention can also be made effective by topical application to the site of infection. Other contact methods include applying the compounds or compositions of the present invention by direct spraying and residual spraying, aerial spraying, gels, seed coating, microencapsulation, systemic absorption, bait, ear tags, pellets, sprayers, fumigants, aerosols, powders, and many other methods. One embodiment of the contact method is a size-stable fertilizer granule, stick, or tablet comprising the compounds or compositions of the present invention. The compounds of the present invention can also be impregnated into materials used for assembling invertebrate control devices (e.g., insect nets).

[0155] The compositions of the present invention can also be used in providing seed treatments that protect seeds from invertebrate pests. In the context of this disclosure and the claims, seed treatment means bringing seeds into contact with a biologically effective amount of the compounds of the present invention, typically formulated into the compositions of the present invention. Such seed treatments protect seeds from invertebrate soil pests and generally also protect the roots and other plant parts in contact with the soil of seedlings developing from germinating seeds. The seed treatments also provide protection to the leaves by allowing the compounds of the present invention, or a second active ingredient, to move within the developing plant. Seed treatments can be applied to various types of seeds, including those that can germinate to form transgenic plants expressing specific characteristics. Representative examples include those expressing proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxin, or those expressing herbicide resistance, such as glyphosate acetyltransferases providing glyphosate resistance.

[0156] One method of seed treatment is to spray or dust the seeds with the compounds of the present invention (i.e., as a prepared composition) before sowing. Compositions formulated for seed treatment generally contain a film-forming agent or binder. Therefore, the seed coating compositions of the present invention typically contain a biologically effective amount of a compound of formula I, an N-oxide or a salt thereof, and a film-forming agent or binder. Seed coating is achieved by spraying a flowable suspension concentrate directly into a seed rolling bed, followed by seed drying. Alternatively, other formulation types such as wet powders, solutions, suspensions, emulsions, and aqueous solutions of emulsions can be sprayed onto the seeds. This method is particularly suitable for applying film coatings to seeds. Various coating devices and methods are available to those skilled in the art.

[0157] The treated seeds typically contain the compounds of the present invention in an amount of about 0.1 g to 1 kg per 100 kg of seeds (i.e., about 0.0001 to 1% by weight of the seeds before treatment). The flowable suspension formulation for seed treatment typically contains about 0.5 to about 70% of the active ingredient, about 0.5 to about 30% of a film-forming binder, about 0.5 to about 20% of a dispersant, 0 to about 5% of a thickener, 0 to about 5% of a pigment and / or dye, 0 to about 2% of an antifoaming agent, 0 to about 1% of a preservative, and 0 to about 75% of a volatile liquid diluent.

[0158] The compounds of the present invention can be incorporated into bait compositions that are consumed by invertebrate pests or used in devices such as traps, bait stations, etc. Such bait compositions may be in granular form and comprise (a) an active ingredient in a biologically effective amount of a compound of formula I, its N-oxide, or a salt thereof; (b) one or more food materials; optionally (c) an insect attractant; and optionally (d) one or more wetting agents. Notably, granular or bait compositions comprising about 0.001-5% of the active ingredient, about 40-99% of the food material and / or insect attractant; and optionally about 0.05-10% of a wetting agent, can effectively control soil invertebrate pests at very low application rates, especially at doses of the active ingredient that are lethal when ingested rather than directly contacted. Some food materials can be used as both a food source and an insect attractant. Food materials include carbohydrates, proteins, and lipids. Examples of food materials are vegetable powders, sugars, starches, animal fats, vegetable oils, yeast extracts, and milk solids. Examples of insect attractants are flavorings and seasonings, such as fruit or plant extracts, spices, or other animal or plant components, pheromones, or other agents known to attract target invertebrate pests. Examples of humectants, or water-retaining agents, are ethylene glycol and other polyols, glycerin, and sorbitol. Of particular note are bait compositions (and methods of using such bait compositions) for controlling at least one invertebrate pest selected from ants, termites, and cockroaches. Devices for controlling invertebrate pests include the bait composition of the present invention and an outer cover adapted to contain the bait composition, wherein the outer cover has at least one opening sized to allow invertebrate pests to pass through, enabling them to access the bait composition from a location outside the outer cover, and wherein the outer cover is also adapted to be placed in or near potential or known locations of invertebrate pest activity.

[0159] The compounds of the present invention can be applied without other adjuvants, but the most common application is in the form of formulations containing one or more active ingredients having a suitable carrier, diluent, and surfactant, and potentially in combination with food depending on the intended end use. One method of application involves spraying an aqueous dispersion or refined oil solution of the compounds of the present invention. Combinations with spray oil, spray oil concentrate, thickeners, adjuvants, other solvents, and synergists such as piperonyl butyl ether generally enhance the effect of the compounds. For non-agricultural applications, such sprays can be applied from spray containers such as canisters, bottles, or other containers, via a pump or by releasing them from a pressurized container such as a pressurized aerosol spray can. Such spray compositions can take various forms, such as spray, mist, foam, smoke, or dust. Therefore, such spray compositions may also contain propellants, foaming agents, etc., depending on the application requirements. It is noteworthy that spray compositions contain a biologically effective amount of the compounds or compositions of the present invention, and a carrier. One embodiment of such a spray composition contains a biologically effective amount of the compounds or compositions of the present invention, and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, chlorofluorocarbons, dimethyl ethers, and mixtures thereof. Of particular interest are spray compositions (and methods of using such spray compositions dispensed from a spray container) for controlling at least one invertebrate pest, said invertebrate pest being selected from mosquitoes, black flies, stable flies, deer flies, horse flies, wasps, hornets, giant hornets, ticks, spiders, ants, black flies, etc., including various of the above-mentioned pests or combinations thereof.

[0160] Non-agricultural uses refer to the control of invertebrate pests in areas not used for agricultural purposes. The non-agricultural uses of the compounds and compositions of this invention include controlling invertebrate pests in stored grains, beans, and other food products, as well as in textiles such as clothing and carpets. The non-agricultural uses of the compounds and compositions of this invention also include controlling invertebrate pests on ornamental plants, forest crops, yards, utility land along roadsides and railways, and turf such as lawns, golf courses, and pastures. The non-agricultural uses of the compounds and compositions of this invention also include controlling invertebrate pests in dwellings and other buildings inhabited by humans and / or companion animals, livestock, farm animals, zoo animals, or other animals. The non-agricultural uses of the compounds and compositions of this invention also include controlling pests such as termites that damage wood or other building materials used in construction.

[0161] The non-agricultural uses of the compounds and compositions of the present invention also include protecting human and animal health by controlling invertebrate pests that parasitize or transmit infectious diseases. Controlling animal parasites includes controlling ectoparasites that live on the surface of the host animal's body (e.g., shoulders, armpits, abdomen, inner thighs) and endoparasites that live inside the host animal's body (e.g., stomach, intestines, lungs, veins, subcutaneous tissue, lymphatic tissue). Ectoparasitic or disease-transmitting pests include, for example, chiggers, ticks, lice, mosquitoes, flies, mites, and fleas. Endoparasites include canine filarial worms, hookworms, and worms. The compounds and compositions of the present invention are particularly suitable for combating ectoparasitic or disease-transmitting pests. The compounds and compositions of the present invention are suitable for systemic and / or non-systemic control of infections or lesions caused by parasites in animals.

[0162] The compounds and compositions of the present invention are suitable for combating parasites that infest animals, including wild animals, livestock, and agricultural and working animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, bison, buffalo, rabbits, hens, turkeys, ducks, and geese (e.g., raised for meat, milk, butter, eggs, fur, leather, feathers, and / or wool). By combating parasites, mortality rates are reduced and reduced yields (in meat, milk, wool, fur, eggs, honey, etc.) are mitigated, making the application of compositions containing the compounds of the present invention more economical and simplifying animal husbandry.

[0163] The compounds and compositions of the present invention are particularly suitable for combating parasites that infest companion animals and pets (e.g., dogs, cats, pet birds and ornamental fish), research and laboratory animals (e.g., hamsters, guinea pigs, rats and mice), and animals kept in zoos, wild habitats and / or circuses.

[0164] In embodiments of the invention, the animal is preferably a vertebrate, and more preferably a mammal, bird, or fish. In a particular embodiment, the animal is a mammal (including great apes, such as humans). Other mammals include primates (e.g., monkeys), bovids (e.g., cattle or dairy cows), suidae (e.g., domestic pigs or wild boars), sheep (e.g., goats or sheep), equines (e.g., horses), canids (e.g., dogs), felines (e.g., domestic cats), camels, deer, donkeys, bison, buffalo, antelopes, rabbits, and rodents (e.g., guinea pigs, squirrels, rats, mice, gerbils, and hamsters). Birds include anatidae (swans, ducks, and geese), columbidae (e.g., doves and pigeons), pheasants (e.g., partridges, grouse, and turkeys), gallinae (e.g., chickens), parrots (e.g., parrots, macaws, and parrots), birds of prey, and ostriches.

[0165] Birds treated or protected by the compounds of this invention are related to commercial or non-commercial bird husbandry. These include ducks such as swans, geese, and ducks; doves such as doves and pigeons; pheasants such as partridges, grouse, and turkeys; chickens such as chickens; and parrots such as parrots, macaws, and parrots kept as pets or in the collecting market, etc.

[0166] For the purposes of this invention, the term "fish" should be understood to include, without limitation, bony fish, specifically teleost fish. The orders Salmoniformes (including Salmonidae) and Perciformes (including Acanthodianidae) are both included in teleost fish. Possible examples of fish include Salmonidae, Pleuronectiidae, Sebastiidae, Cichlididae, and Acanthodianidae, among others.

[0167] Other animals that could benefit from the methods of the present invention are also envisioned, including marsupial mammals (such as kangaroos), reptiles (such as farmed turtles), and other economically important livestock for which the methods of the present invention can safely and effectively treat or prevent parasitic infections or infestations.

[0168] Examples of invertebrate parasitic pests controlled by applying an effective amount of the compound of the present invention to the protected animal include ectoparasites (arthropods, mites, etc.) and endoparasites (worms, such as nematodes, flukes, tapeworms, acanthocephalans, etc.).

[0169] Helminthiasis is generally described as a disease or class of diseases caused by infection with parasites called worms that affect an animal host. The term "worm" is intended to include nematodes, flukes, tapeworms, and acanthocephalans. Helminthiasis is a common and serious economic problem associated with domesticated animals such as pigs, sheep, horses, cattle, goats, dogs, cats, and poultry.

[0170] Among worms, a class of worms described as nematodes can cause widespread and sometimes serious infections in a variety of animal types. Contemplated nematode animals that can be treated with the compositions and methods of the present invention include, but are not limited to, the following genera: *Echinopsula*, *Strongyloides felis*, *Ahrodontia*, *Angiostrongylus*, *Ascaris*, *Ascaris*, *Brugia*, *Odontostomum*, *Capillaria*, *Chaetomium*, *C. cubitus*, *C. annuli*, *Dictyophora*, *Bulbus*, *Taenia*, *Dendrocalamus ... The genera include *Heterostigma*, *Ascaris*, *Loa*, *Mansonia*, *Müller*, *Ceratophyllum ... and *Ceratophyllum*.

[0171] Among the nematode genera mentioned above that can infect the aforementioned animals, the most common genera are *Haemaphysalis*, *Trichophyton*, *Gastroceras*, *Nematoda*, *Cuppella*, *Ascaris*, *Odontospira*, *Nodularia*, *Chaetomium*, *Strongyloides*, *Trichuris*, *Trichophyton*, *Trichophyton*, *Trichophyton*, *Trichophyton*, *Dictamnus*, *Capillaria*, *Heterochnella*, *Toxocara*, *Chicken Ascaris*, *Caulis Ascaris*, *Caulis Ascaris*, *Caulis Ascaris*, *Hookworm*, *Toxocara*, and *Parascaris*. Some of these, such as *Trichophyton*, *Cuppella*, and *Nodularia*, primarily attack the intestines, while others, such as *Haemaphysalis* and *Gastroceras*, are more prevalent in the stomach, and still others, such as *Dictamnus*, are found in the lungs. Other parasites also reside in other tissues, such as the heart and blood vessels, subcutaneous tissue, and lymphatic tissue.

[0172] Trematodes that can be treated with the compositions and methods of the present invention include, but are not limited to, the following genera: *Schistosome*, *Fasciola*, *Dwarf Trematode*, *Opisthodon*, *Paragonimus*, and *Schistosome*.

[0173] The tapeworms that can be treated with the compositions and methods of the present invention include, but are not limited to, the following genera: *Sparganum*, *Diploporum*, *Spirometra*, and *Taenia*.

[0174] The most common genera of parasites in the human gastrointestinal tract are *Ahrodonta*, *Isodonta*, *Ascaris*, *Strongyloides*, *Trichodina*, *Capillaria*, *Trichuris*, and *Pinus*. Other medically important genera of parasites found in the blood or in other tissues and organs outside the gastrointestinal tract include filarial worms such as *Wuceta*, *Brugia*, *Spirocera*, and *Loa*, as well as *Draconis*, and other intestinal roundworms such as *Strongyloides* and *Capillaria*.

[0175] Numerous other genera and species of worms are known in the art and can also be conceived for treatment with the compounds of the present invention.

[0176] It is also envisioned that the compounds of the present invention can effectively resist a variety of animal ectoparasites, such as arthropod ectoparasites of mammals and birds; however, it is also envisioned that some arthropods may also be endoparasites.

[0177] Therefore, insect and tick pests include, for example, biting insects such as flies and mosquitoes, mites, ticks, lice, fleas, stink bugs, parasitic maggots, etc.

[0178] Adult flies include, for example, hornflies or bloodflies, horseflies or horse flies, stable flies or stable stinging flies, black flies or black flies, deer flies or spotted flies, lice flies or planthoppers, tsetse flies or tsetse flies. Parasitic fly larvae include, for example, skin flies (stomach flies and mad flies), green bottle flies or blowflies, whorled fly larvae or whorled fly larvae, cow flies or footflies, wool fly larvae, and horse stomach fly larvae. Mosquitoes include, for example, Culex, Anopheles, and Aedes.

[0179] Mites include genera such as Mesosphaeria, such as *Gastropoda sinensis*, including chicken mites and chicken skin mites; scabies mites or itch mites, such as genus *Scabiei*, including scabies mites; animal scabies mites, such as genus *Ophiopogon*, including cattle scabies mites and sheep itch mites; and chiggers, such as genus *Tsutoma*, including North American chiggers and *Tsutoma albopictus*.

[0180] Ticks include soft ticks, such as those in the family Cryptorchididae, including genera such as *Ixodes scabra* and *Ixodes scabra*; hard ticks include those in the family Ixodes, such as *Ixodes rubrum*, *Ixodes mutabilis*, *Ixodes angustifolia*, *Ixodes natans ... and *Ixodes natans*.

[0181] Lice include, for example, sucking lice, such as those in the genera *Avianus* and *Cattle Lobelia*; and hairy lice, such as those in the genera *Hymenopterus*, *Gnaphalium*, and *Vibrio*.

[0182] Fleas include, for example, species of the genus *Ctenocephalides* such as canine fleas (*Ctenocephalides canis*) and cat fleas (*Ctenocephalides felis*); species of the genus *Xenopsylla cheopis*; and species of the genus *Pulex irritans*.

[0183] Stink bugs include, for example, the genus *Cimex lectularius* or the common stink bug; subfamily *Cimexinae*, including assassin bugs also known as assassin bugs; for example, the genus *Cimex* and the genus *Cimex*.

[0184] Generally speaking, flies, fleas, lice, mosquitoes, midges, mites, ticks, and worms cause enormous damage to livestock and companion animals. Arthropod parasites also cause problems for humans and can be carriers of pathogenic organisms in humans and animals.

[0185] Numerous other arthropod pests and ectoparasites are known in the art and can also be conceived to be treated with the compounds of the present invention.

[0186] Specifically, the compounds of the present invention are effective against ectoparasites, including fleas, etc.

[0187] Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea).

[0188] The compounds of this invention are also effective against other ectoparasites, including flying insects such as *Haematobiairritans*, *Stomoxys calcitrans*, *Simulium*, *Glossina*, *Hydrotaea irritans*, *Musca autumnalis*, *Musca domestica*, *Morllia simplex*, *Tabanus*, *Botrytis cinerea*, *Betweenia spp.*, *Betweenia spp.*, *Greenbottle Fly*, *Calliphora*, *Culex*, and *Oestrus*. ovis (sheep nasal fly), Culicoides (midges), horseflies, horse stomach flies, red horse stomach flies, and horse nasal stomach flies; lice, such as cattle lice (livestock lice), horse hair lice, donkey blood lice, cat bird lice, dog lice, spiny-toothed lice, and dog-biting hair lice; sheep ticks, such as sheep ticks; mites, such as itch mites, scabies mites, cattle foot mites, horse worm mites, chelicerate mites, cat ear mites, chigger mites, and ear mites; and flat lice, such as hard ticks, cattle ticks, fan-shaped ticks, blunt-eyed ticks, leather ticks, glass-eyed ticks, and haematomalacia ticks.

[0189] Biologically active compounds or reagents that can be used in the compositions of the present invention include organophosphate insecticides. These insecticides have a very broad range of activity as insecticides and, in some cases, insecticidal activity. Organophosphate insecticides include, for example, phosmet, terbufos, dimethoate, dichlorvos, ethion, trichlorfon, methyl parathion, chlorpyrifos, malathion, acephate, methamidophos, ethyl parathion, methyl parathion, methamidophos, phorate, trichlorfon, and fenpropathrin. Combinations of the methods and compositions of the present invention with carbamate-type insecticides, and with organochlorine-type insecticides, including, for example, carbaryl, aldicarb, quizalofop-p-ethyl, ethoxysulfuron, carbofuran, etc., are also contemplated. Combinations with biological insecticides, including repellents, pyrethroids (and their synthetic variants, such as allethrin, pyrethrum, pyrethroid, tetrabromopyrethrin), and nicotine, which is commonly used as an acaricide. Other envisioned combinations are mixed insecticides, including: Bacillus, chlorobenzene, formamidin (such as amitraz), copper compounds (such as copper hydroxide and copper oxychloride), cypermethrin, deltamethrin, trichlorfon, endosulfan, cypermethrin, lambda-cyhalothrin, methoxydimethyldimethalin, and sulfur.

[0190] It is noteworthy that the additional biologically active compounds or reagents are selected from anthelmintics known in the art, such as avermectin (e.g., ivermectin, moxibustion, milbemycin), benzimidazole (e.g., albendazole, triclofenazole), N-salicylic acid aniline (e.g., chlorsenoyl, hydroxychlorozadamide), substituted phenols (e.g., nitrohydroxyiodine), pyrimidines (e.g., pyrimidine), imidazoles (e.g., levamisole), and praziquantel.

[0191] Other biologically active compounds or reagents that can be used in the compositions of the present invention may be selected from insect growth regulators (IGRs) and juvenile hormone analogs (JHAs), such as diflubenzuron, chlorfenapyr, fluzoflubenzuron, cyprodinil, and methoxyprotein, thereby providing initial and sustained control of parasites to the animal and its environment (at all stages of insect growth, including eggs).

[0192] It is noteworthy that the biologically active compounds or reagents that can be used in the compositions of this invention are selected from antiparasitic avermectin compounds. As mentioned above, avermectin compounds are a series of potent antiparasitic agents known to be effective against a broad spectrum of mammalian endoparasites and ectoparasites.

[0193] The compositions of the present invention may also contain trematodes. Suitable trematodes include, for example, triclofenac, fenbendazole, albendazole, closulon, and ocbendazole. It should be understood that the above combinations may also include combinations of antibiotics, antiparasitic and antitrematode active compounds.

[0194] In addition to the combinations described above, it is also envisioned to provide combinations of the methods and compounds of the present invention as described herein with other animal health agents such as trace elements, anti-inflammatory agents, anti-infective agents, hormones, dermatological preparations (including preservatives and disinfectants), and immunomodulatory agents such as vaccines and antiserums for disease prevention.

[0195] For example, such anti-infective agents include one or more antibiotics that may be administered simultaneously, optionally in combination and / or in separate dosage forms, during treatment with the compounds or methods of the present invention.

[0196] Non-agricultural applications in the veterinary sector include administration via conventional methods, such as enteral administration in the form of tablets, capsules, beverages, infusions, granules, pastes, pellets, feeding procedures, or suppositories; or non-enteric administration via injection (including intramuscular, subcutaneous, intravenous, and intraperitoneal injections) or implantation; nasal administration; administration via, for example, by immersion or soaking, spraying, washing, coating with powder, or application to a small area of ​​the animal; and local administration via articles containing the compositions of the present invention, such as collars, ear tags, tail straps, limb straps, or bridles.

[0197] Any compound of the present invention, or a suitable combination of such compounds, may be applied directly to an animal subject, and / or indirectly by applying it to the local environment in which the animal inhabits (such as bedding, enclosures, etc.). Direct application includes bringing the compound into contact with the skin, fur, or feathers of the animal subject, or feeding or injecting the compound into the animal.

[0198] The compounds of the present invention can be administered in a controlled-release form, such as a subcutaneous slow-release formulation, or in the form of a controlled-release device attached to an animal, such as a flea collar. Collars for controlled-release insecticides to provide long-term protection of companion animals from flea infestations are known in the art.

[0199] Typically, the antiparasitic compositions according to the invention comprise a compound of formula I, its N-oxide, or a salt thereof, and a mixture of one or more pharmaceutically or veterinarily acceptable carriers, said carriers comprising excipients and adjuvants selected according to the intended route of administration (e.g., oral, topical, or parenteral administration such as injection) and according to standard operating procedures. Furthermore, a suitable carrier is selected based on its compatibility with one or more active ingredients in the composition, including the presence of relative stability to pH and water content. Therefore, compositions for protecting animals from invertebrate parasitic pests, comprising at least one carrier and an effective amount of the compound of the invention for antiparasitic purposes, are of particular interest.

[0200] For administration outside the body (including intravenous, intramuscular, and subcutaneous injection), the compounds of the present invention can be formulated into suspensions, solutions, or emulsions in oily or aqueous carriers and may contain excipients such as suspending agents, stabilizers, and / or dispersants. The compounds of the present invention can also be formulated for rapid concentration or continuous infusion. Injectable pharmaceutical compositions comprise an aqueous solution of the active ingredient (e.g., a salt of the active compound), preferably in a physiologically compatible buffer containing other excipients or excipients as known in the field of pharmaceutical formulations. Furthermore, suspensions of the active compound can be prepared in lipophilic carriers. Suitable lipophilic carriers include fatty oils such as sesame oil, synthetic fatty acid esters such as ethyl oleate and triglycerides, or substances such as liposomes. Injectable aqueous suspensions may contain substances that increase the viscosity of the suspension, such as sodium carboxymethyl cellulose, sorbitol, or dextran. Formulations for injection may be available in unit dosage forms, such as in ampoule containers or multi-dose containers. Alternatively, the active ingredient may be in powder form and combined with a suitable carrier, such as pyrogen-free sterile water, before use.

[0201] In addition to the formulations described above, the compounds of the present invention can also be formulated into long-acting formulations. Such long-acting formulations can be administered via implantation (e.g., subcutaneous or intramuscular) or via intramuscular or subcutaneous injection. For this route of administration, the compounds of the present invention can be formulated with a suitable polymeric or hydrophobic material (e.g., in an emulsion containing a pharmaceutically acceptable oil), with an ion exchange resin, or the compounds can be formulated into slightly soluble derivatives, such as, but not limited to, slightly soluble salts.

[0202] For administration by inhalation, the compositions of the invention can be delivered in aerosol spray form using pressurized packaging or nebulizers and suitable propellants, such as, but not limited to, dichlorodifluoromethane, trichlorofluoromethane, dichlorotetrafluoroethane, or carbon dioxide. In the case of pressurized aerosols, the dosage unit can be controlled by providing a valve to deliver a measured amount. Gelatin capsules and cartridges for inhalers or nebulizers can be formulated to contain a powder mixture of the compounds and a suitable powder base such as lactose or starch.

[0203] It has been found that the compounds of the present invention possess favorable pharmacokinetic and pharmacodynamic properties, providing systemic availability through oral administration and ingestion. Therefore, after ingestion by the animal to be protected, the effective antiparasitic concentration of the compounds of the present invention in the blood can protect the treated animal from blood-sucking pests such as fleas, ticks, and lice. It is therefore noteworthy that the oral formulation of the composition (i.e., in addition to an effective antiparasitic amount of the compounds of the present invention, it also comprises one or more carriers selected from binders and fillers suitable for oral administration, as well as concentrated feed carriers) is intended to protect animals from invertebrate parasitic pests.

[0204] For oral administration in the form of solutions (the most readily available absorbed form), emulsions, suspensions, pastes, gels, capsules, tablets, pellets, powders, granules, rumen reserves, and feed / water / lick bricks, the compounds of the present invention can be formulated using binders / fillers known in the art suitable for oral compositions, such as sugars and sugar derivatives (e.g., lactose, sucrose, mannitol, sorbitol), starches (e.g., corn starch, wheat starch, rice starch, potato starch), cellulose and derivatives (e.g., methylcellulose, carboxymethylcellulose, ethyl hydroxycellulose), protein derivatives (e.g., corn gluten, gels), and synthetic polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone). Lubricants (e.g., magnesium stearate), disintegrants (e.g., croscarmellose, agar, alginate), and dyes or pigments may be added if desired. Pastes and gels typically also contain binders (e.g., acacia, alginate, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to help maintain the composition in contact with the oral cavity and prevent it from being expelled.

[0205] If the antiparasitic composition is in the form of a concentrated feed, the carrier is typically selected from high-performance feeds, feed cereals, or concentrated protein. In addition to the antiparasitic active ingredient, such compositions containing concentrated feed also contain additives that promote animal health or growth, improve the meat quality from slaughtered animals, or are suitable for livestock farming. These additives include, for example, vitamins, antibiotics, chemotherapeutic agents, antibacterial agents, antifungal agents, anticoccidial drugs, and hormones.

[0206] Compounds of Formula I can also be formulated into rectal administration compositions, such as suppositories or retention enemas, using conventional suppository bases such as cocoa butter or other glycerides.

[0207] Formulations for topical administration are typically in the form of powders, creams, suspensions, sprays, emulsions, foams, pastes, aerosols, ointments, or gels. Topical formulations are more typically water-soluble solutions, which may be in the form of a concentrate diluted before use. Parasitic compositions suitable for topical administration generally comprise the compounds of the present invention and one or more suitable topical carriers. When the parasitic composition is applied topically to the exterior of an animal in a line or spot (i.e., precise therapy), the active ingredient migrates across the animal's surface to cover most or all of its external surface area. Therefore, the treated animal is protected from invertebrate pests, particularly those that feed on the animal's epidermis, such as ticks, fleas, and lice. Therefore, formulations for targeted topical administration typically contain at least one organic solvent to facilitate the delivery of the active ingredient to the animal's skin and / or penetration into the animal's epidermis. Carriers in such formulations include propylene glycol, paraffin, aromatic compounds, esters (such as isopropyl myristate), ethylene glycol ethers, alcohols (such as ethanol, n-propanol, 2-octyldodecanool, or oleyl alcohol); solutions of monocarboxylic acid esters, such as isopropyl myristate, isopropyl palmitate, oxalate laurylate, oleyl oleate, decyl oleate, hexyl laurylate, and chain length C. 12 -C 18 Hexanoates of saturated fatty alcohols; solutions of dicarboxylic acid esters, such as dibutyl phthalate, diisopropyl isophthalate, diisopropyl adipate, di-n-butyl adipate, or esters of aliphatic acids (e.g., ethylene glycol). The presence of crystallization inhibitors or dispersants known in the pharmaceutical or cosmetic industries may also be advantageous.

[0208] Drenching formulations can also be formulated to control parasites in agronomically valuable animals. The drenching formulations of this invention can be in the form of liquid, powder, emulsion, foam, paste, aerosol, ointment, cream, or gel. Drenching formulations are typically liquid. These drenching formulations are effective on sheep, cattle, goats, other ruminants, camelids, pigs, and horses. The drenching formulation is typically applied by pouring it in one or more thin lines, or precisely onto the midline of the animal's back (back) or shoulders. More typically, it is applied by pouring the formulation along the animal's back, down the spine. The formulation can also be applied by other conventional methods, including wiping it onto at least a small area of ​​the animal with an impregnated substance, or by using commercially available application devices, such as via syringe, spray, or through a spray grate. The drenching formulation includes a carrier and may also contain one or more additional ingredients. Examples of suitable additives include stabilizers such as antioxidants, spreading agents, preservatives, adhesion promoters, active solubilizers such as oleic acid, viscosity modifiers, UV blockers or absorbers, and colorants. Surfactants may also be included in these formulations, including anionic, cationic, nonionic, and amphoteric surfactants.

[0209] The formulations of this invention typically contain antioxidants, such as BHT (butylated hydroxytoluene). The antioxidants are generally present at a concentration of 0.1% to 5% (by weight / volume). Some formulations require solubilizers, such as oleic acid, to dissolve the active agent, especially when using spinosad. Common spreading agents used in these pouring formulations are: IPM, IPP, saturated C... 12 -C 18 Fatty alcohols, including caprylic / capric esters, oleic acid, oleyl alcohol esters, ethyl oleate, triglycerides, silicone oils, and DPM. The spray formulations of this invention can be prepared according to known techniques. When the spray is a solution, the insect repellent / insecticide is mixed with a carrier or medium by heating and stirring, if desired. Additives or supplementary ingredients can be added to the mixture of the active agent and the carrier, or they can be mixed with the active agent before adding the carrier. If the spray is an emulsion or suspension, these formulations can be prepared similarly using known techniques.

[0210] Other delivery systems for more hydrophobic drug compounds can be used. Liposomes and emulsions are well-known examples of delivery media or carriers for hydrophobic drugs. Additionally, organic solvents such as dimethyl sulfoxide can be used if desired.

[0211] For agronomic applications, the amount required for effective control (i.e., the "biologically effective dose") will depend on factors such as the species of invertebrate pest to be controlled, the pest's life cycle, life stage, size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, etc. Under normal circumstances, an application rate of approximately 0.01 to 2 kg of active ingredient per hectare is sufficient to control pests within an agronomic ecosystem; however, application rates as low as 0.0001 kg per hectare may be sufficient, or as high as 8 kg per hectare may be necessary. For non-agronomic applications, the effective dose will range from approximately 1.0 to 50 mg per square meter; however, application rates as low as 0.1 mg per square meter may be sufficient, or as high as 150 mg per square meter may be necessary. Those skilled in the art can readily determine the biologically effective dose required to achieve the desired level of invertebrate pest control.

[0212] Generally, in veterinary use, a compound of formula I, its N-oxide, or a salt thereof is applied to animals at an effective parasitic dose to protect them from invertebrate parasitic pests. An effective parasitic dose is the amount of active ingredient required to achieve the observed reduction in the incidence or activity of the target invertebrate parasitic pest. Those skilled in the art will recognize that the effective parasitic dose can vary depending on the compound and composition according to the invention, the desired parasitic effect and duration, the target invertebrate species, the animal to be protected, the mode of application, etc., and the amount required to achieve a specific effect can be determined through simple experiments.

[0213] For oral administration to homeothermic animals, the daily dose of the compounds of the present invention is typically in the range of about 0.01 mg / kg animal body weight to about 100 mg / kg animal body weight, more typically about 0.5 mg / kg animal body weight to about 100 mg / kg animal body weight. For topical (e.g., skin) administration, dips and sprays typically contain about 0.5 ppm to about 5000 ppm, more typically about 1 ppm to about 3000 ppm of the compounds of the present invention. Detailed Implementation

[0214] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0215] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0216] Table 1. Compound structures and their properties 1 H NMR data

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0225] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the table below are either commercially available or can be easily prepared by those skilled in the art.

[0226] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0227] 1. Synthesis of Compound 3

[0228] (1) In a 50 mL single-necked flask, compound 3-1 (300 mg, 0.55 mmol) was dissolved in 10 mL of 1,4-dioxane and 1 mL of water. Cesium fluoride (250.38 mg, 1.65 mmol) and compound 3-2 (158.32 mg, 0.83 mmol) were added, and the mixture was purged with nitrogen once. Pd(dppf)Cl2 (40 mg, 0.05 mmol) was added, and the mixture was purged with nitrogen three times. The mixture was stirred at 100 °C for 12 h. The reaction was monitored by LCMS until complete. The reaction solution was quenched with water, extracted with ethyl acetate, and the organic phase was washed with water and saturated brine. The mixture was dried and concentrated, and the residue was purified by column chromatography to give compound 3 (56 mg, yield 19.14%, pale yellow solid).

[0229]

[0230] 2. Synthesis of Compound 9

[0231] In a 50 mL single-necked flask, compound 3-1 (300 mg, 0.55 mmol) was dissolved in 10 mL of 1,4-dioxane and 1 mL of water. Cesium fluoride (250.38 mg, 1.65 mmol) and compound 9-1 (142.73 mg, 0.83 mmol) were added, and the mixture was purged with nitrogen once. Pd(dppf)Cl2 (40 mg, 0.05 mmol) was added, and the mixture was purged with nitrogen three times. The mixture was stirred at 100 °C for 12 h. The reaction was monitored by LC-MS until complete. The reaction solution was quenched with water, extracted with ethyl acetate, and the organic phase was washed with water and saturated brine. The solution was dried and concentrated, and the residue was purified by column chromatography to give compound 9 (89 mg, yield 31.60%, pale yellow solid).

[0232]

[0233] Bioactivity evaluation (spray method):

[0234] Compound insecticidal activity test:

[0235] The compound of the present invention was dissolved in acetone and then diluted with water to prepare solutions of different concentrations (ppm).

[0236] Fall armyworm, armyworm, diamondback moth, and beet armyworm: Insects with consistent physiological states, continuously reared indoors, were placed in disposable petri dishes. Ten 2nd-3rd instar larvae were inoculated into each dish, along with four corn leaves. Spraying was then performed using a spray tower, with each dosage repeated three times. Acetone at the same concentration served as a control. After treatment, the insects were transferred to their original rearing conditions. The number of dead insects was checked after 48 hours, and the mortality rate was calculated using the formula: Mortality rate (%) = (Number of dead insects / Number of test insects) * 100. Representative experimental results are shown in Table 2.

[0237] Table 2 Insecticide Test Results

[0238]

[0239] Note: N represents no data; reference compound A:

[0240] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent control activity against many agricultural pests, including Lepidoptera (such as corn borers, rice stem borers, diamondback moths, beet armyworms, cotton bollworms, fall armyworms, and armyworms), Homoptera (such as cotton aphids, turnip aphids, pea aphids, peanut aphids, and green mirid bugs), Acari (such as two-spotted spider mites, truncated spider mites, and Turkestan spider mites), Diptera (such as leek leeks), Coleoptera (such as yellow flea beetles and small ape leaf beetles), and thrips (such as palm thrips, onion thrips, and tobacco thrips), as well as sanitary pests such as cockroaches (such as termites and cockroaches) and flies (such as flies and mosquitoes). These compounds not only possess broad-spectrum, high-efficiency, and systemic characteristics, but also effectively control resistant pests and have considerable commercial value.

Claims

1. A substituted benzisoxazole compound, as shown in general formula I: in, Any one of X1, X2, X3, and X4 is N, and the other three independently represent CR1; R1 independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, -OR 10 S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 , cycloalkyl, aryl or heterocyclic; wherein the alkyl, alkenyl or ynyl group is optionally selected from halogen, trialkylsilyl, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from cycloalkyl, heterocyclic or aryl groups; X represents alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, -N(R) 10 2. Cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; Y represents alkyl; R 10 Each of these can independently represent hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, heterocyclic, heterocyclic alkyl, aryl, or arylalkyl. m represents 0, 1, or 2; The aforementioned "cycloalkyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure. R 11 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

2. The substituted benzisoxazole compound according to claim 1, characterized in that, R1 independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, -OR 10 -S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 C3-C8 cycloalkyl, aryl, or heterocyclic groups; wherein, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl is optionally selected from halogens, tri-C1-C8 alkylsilyl groups, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from C3-C8 cycloalkyl, heterocyclic or aryl groups; X represents C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 ynyl, halogenated C2-C8 ynyl, -N(R) 10 2. C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, aryl, heterocyclic, aryl C1-C8 alkyl or heterocyclic C1-C8 alkyl; Y represents C1-C8 alkyl; R 10 Each of these can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, heterocyclic, heterocyclic-C1-C8 alkyl, aryl or aryl-C1-C8 alkyl; m represents 0, 1, or 2; The aforementioned "C3-C8 cycloalkyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure. R 11 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo-C1-C8 alkoxy.

3. A substituted benzisoxazole compound according to claim 1 or 2, characterized in that, R1 independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, -OR 10 -S(O) m R 10 -N(R) 10 )2、-(CO)R 10 -(CO)OR 10 C3-C6 cycloalkyl, aryl, or heterocyclic groups; wherein, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl is optionally selected from halogens, tri-C1-C6 alkylsilyl groups, -OR 10 -S(O) m R 10 It is substituted by at least one group selected from C3-C6 cycloalkyl, heterocyclic or aryl groups; X represents C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 ynyl, halogenated C2-C6 ynyl, -N(R) 10 2. C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, heterocyclic, aryl C1-C6 alkyl or heterocyclic C1-C6 alkyl; Y represents C1-C6 alkyl; R 10 Each of these can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, heterocyclic, heterocyclic-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl. m represents 0, 1, or 2; The aforementioned "C3-C6 cycloalkyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -(CO)N(R) 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in the ring is replaced; or two adjacent carbon atoms on the ring form a fused ring with unsubstituted or halogen-substituted -OCH2O-, -CH2CH2CH2O- or -CH=CHCH=CH-; or a saturated carbon atom on the ring is connected to both ends of an unsubstituted or halogen-substituted -OCH2CH2O- to form a ring structure. R 11 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy.

4. A substituted benzisoxazole compound according to any one of claims 1-3, characterized in that, X1 is N, and X2, X3, and X4 each independently represent CR1; X2 is N, and X1, X3, and X4 each independently represent CR1; X3 is N, and X1, X2, and X4 independently represent CR1; or, X4 represents N, and X1, X2, and X3 each independently represent CR1; Preferably, the compound is selected from any one of the compounds in Table 1.

5. A method for preparing a substituted benzisoxazole compound as described in any one of claims 1-4, characterized in that, Includes the following steps: The compound represented by general formula II reacts with the compound represented by general formula III to produce the compound represented by general formula I, and the reaction equation is as follows: In this case, either Q1 or Q2 is a halogen, and the other is a... The definitions of X, Y, X1, X2, X3, and X4 are as described in any one of claims 1-4; Preferably, the reaction is carried out in the presence of a base, a catalyst, and a solvent; more preferably, the base is selected from at least one inorganic or organic base; the catalyst is selected from at least one of Pd(dppf)Cl2, Pd(OAc)2, PdCl2, or 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex; and / or the solvent is an organic solvent / water, wherein the organic solvent is selected from at least one of aromatic hydrocarbons, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

6. An insecticide composition, characterized in that, It includes at least one of the substituted benzisoxazole compounds according to any one of claims 1-4 in an insecticidal effective amount; preferably, it also includes a formulation adjuvant; more preferably, it also includes other active ingredients.

7. A method for controlling pests, characterized in that, Includes a biologically effective amount of the substituted benzisoxazole compound of any one of claims 1-4 or the composition of claim 6, which exposes the pest or its environment to biologically effective amounts.

8. Use of the substituted benzisoxazole compound as described in any one of claims 1-4 or the composition as described in claim 6 in the control of pests.

9. An intermediate as described in Formula II of claim 5.

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