A spiromesifen derivative or its as a pesticidally acceptable salt, compositions and use thereof

Abstract

This invention belongs to the field of pesticides, specifically relating to a spirodiclofen derivative or its pesticide-acceptable salts, compositions, and uses thereof. The compound has the structure of formula (I): where each group is defined as shown in the specification. The spirodiclofen derivative of this invention exhibits higher insecticidal or acaricidal activity than known compounds, particularly excellent bioactivity against insect or mite eggs.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a spirodiclofen derivative or its pesticide-acceptable salts or compositions, and to the use of these compounds or their pesticide-acceptable salts or compositions as insecticides or acaricides. Background Technology

[0002] Spirodiclofen derivatives with insecticidal activity are described in patents EP0528156A and CN1174676C, but their insecticidal or acaricidal activity is still insufficient in practical applications, and their activity against target organisms other than whiteflies is not very satisfactory. This invention provides a novel spirodiclofen derivative with insecticidal or acaricidal activity, a method for its preparation, and the uses of these compounds in insecticidal or acaricidal applications, particularly exhibiting excellent activity against insect or mite eggs, and good bioactivity against targets other than whiteflies.

[0003] Technical issues

[0004] To address the aforementioned problems in the prior art, this invention provides a spirodiclofen derivative or its pesticide-acceptable salt, composition, and uses. Surprisingly, the spirodiclofen derivative exhibits excellent biological activity, effectively killing pests and possessing sufficient safety for crops, with low susceptibility to resistance. Furthermore, it demonstrates good biological activity against targets other than whiteflies.

[0005] Technical solutions

[0006] The technical solution adopted by the present invention to achieve the above objectives is: a spirodiclofen derivative or its pesticide-acceptable salt, the structural formula of which is shown in formula (I):

[0007]

[0008] In formula (I),

[0009] R1 is selected from H, halogen, CN, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy or C3-C6 cycloalkyl;

[0010] R2 and R3 each independently represent H, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkylthio, halo-C1-C6 alkylthio, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0011] Alternatively, R2 and R3 together form the group -(CH2). t -, t represents an integer from 1 to 8;

[0012] R4 represents H, halogen, CN, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, halo-C1-C6 alkoxy, C1-C6 alkylthio, halo-C1-C6 alkylthio, C3-C8 cycloalkyl, C3-C8 cycloalkyloxy, nitro, aldehyde, carboxyl, -CO-NH2, -CH2-CO-NH2;

[0013] R5 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy, or C3-C6 cycloalkyl.

[0014] Furthermore, in equation (I),

[0015] R1 is selected from H, halogen, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, and C3-C6 cycloalkyl;

[0016] R2 and R3 each independently represent H, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxy, or halo-C1-C6 alkoxy;

[0017] Alternatively, R2 and R3 together form the group -(CH2). t -, t represents an integer from 2 to 6;

[0018] R4 represents H, halogen, CN, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C4 alkenyl, halo-C2-C4 alkenyl, C2-C6 alkynyl, C1-C4 alkoxy, halo-C1-C4 alkoxy, C3-C6 cycloalkyl, and C3-C6 cycloalkyloxy.

[0019] R5 is selected from C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, and C3-C6 cycloalkyl.

[0020] Furthermore, in equation (I),

[0021] R1 is selected from H, halogen, C1-C4 alkyl, C1-C4 alkoxy or C3-C6 cycloalkyl;

[0022] R2 and R3 together form the group -(CH2). t -, t represents an integer from 3 to 6;

[0023] R4 represents H, halogen, CN, C1-C4 alkyl, halo-C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, and C3-C6 cycloalkyl;

[0024] R5 is selected from C1-C4 alkyl, C1-C4 alkoxy, or C3-C6 cycloalkyl.

[0025] Furthermore, in equation (I),

[0026] R1 represents H, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OMe, OEt, n-PrO, i-PrO, or cyclopropane;

[0027] R2 and R3 together form the group -(CH2). t -, t represents an integer between 3 and 5;

[0028] R4 represents H, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl, CHCl2, CCl3, CH2F, CHF2, CF3, CH2Br, CHBr2, CBr3, CH2CF3, vinyl, OMe, OEt, n-PrO, i-PrO, cyclopropane;

[0029] R5 is selected from C1-C4 alkyl, C1-C4 alkoxy, or C3-C6 cycloalkyl.

[0030] Furthermore, in equation (I),

[0031] R1 represents H, Cl, Me, or Et;

[0032] R2 and R3 together form the group -(CH2). t -, t represents an integer between 3 and 5;

[0033] R4 represents H, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl, CHCl2, CCl3, CH2F, CHF2, CF3, CH2Br, CHBr2, CBr3, vinyl, OMe, OEt, n-PrO, i-PrO, cyclopropane;

[0034] R5 is selected from Me, Et, i-Pr, t-Bu, OMe, OEt, or cyclopropane.

[0035] Furthermore, in equation (I),

[0036] R1 represents H or Me;

[0037] R2 and R3 together form the group -(CH2). t -, t represents 3 or 4;

[0038] R4 represents H, F, Cl, Br, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CH2Cl, CHCl2, CCl3, CH2F, CHF2, CF3, CH2Br, CHBr2, CBr3, vinyl, OMe, OEt, n-PrO, i-PrO, cyclopropane;

[0039] R5 represents Me or Et.

[0040] Furthermore, the compounds with the structure of formula (I) are selected from:

[0041]

[0042]

[0043] The pesticide-acceptable salt can be a salt obtained by reacting the spirodiclofen derivative of the present invention with a chemically acceptable acid, wherein the chemically acceptable acid can be an inorganic acid (such as hydrochloric acid, sulfuric acid, phosphoric acid or hydrobromic acid, etc.) or an organic acid (such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid or benzoic acid, etc.); the pesticide-acceptable salt can also be a salt obtained by reacting the spirodiclofen derivative of the present invention with a chemically acceptable base, wherein the chemically acceptable base can be an inorganic base (such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate) or an organic base (such as trimethylamine, triethylamine, etc.).

[0044] Furthermore, the salts acceptable as pesticides can be potassium salts, sodium salts, ammonium salts, calcium salts, pyridine salts, choline salts, hydrochloride salts, phosphates, acetates, benzenesulfonates, or oxalates.

[0045] The present invention also discloses an insecticidal or acaricidal composition comprising an effective amount of an insecticidal or acaricidal amount of at least one of the spirodiclofen derivatives as described above or a salt thereof acceptable as a pesticide.

[0046] Furthermore, it also includes formulation carriers or formulation adjuvants.

[0047] The present invention also discloses a method for controlling pests or mites, comprising applying an insecticidal or acaricidal effective amount of at least one of the spirodiclofen derivatives as described above or a salt thereof acceptable as a pesticide, or an insecticidal or acaricidal composition as described above, to the pests or mites and / or their habitats.

[0048] The present invention also discloses the use of at least one of the spirodiclofen derivatives as described above or its pesticide-acceptable salts, or the insecticidal or acaricidal compositions as described above, in the control of pests or mites in agriculture and other fields.

[0049] In the definitions of the above compound structural formulas, the technical terms used all have the following meanings:

[0050] Halogens or halogens: refer to fluorine, chlorine, bromine, and iodine.

[0051] C1-C6 alkyl: Straight-chain or branched alkyl groups with 1-6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, or n-butyl, isobutyl, sec-butyl, tert-butyl, etc.

[0052] Halogenated C1-C6 alkyl groups: straight-chain or branched alkyl groups with 1-6 carbon atoms, in which hydrogen atoms may be partially or completely replaced by halogens, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.

[0053] C1-C6 alkoxy groups: straight-chain or branched alkyl groups with 1-6 carbon atoms, linked to the structure by oxygen atoms.

[0054] Halogenated C1-C6 alkoxy groups: straight-chain or branched alkoxy groups with 1-6 carbon atoms, in which hydrogen atoms may be partially or completely replaced by halogens, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.

[0055] The method for synthesizing the compound described in Formula I specifically involves reacting the compound of Formula II with the compound of Formula III (in the chemical formulas listed below, unless otherwise defined, the substituents and symbols have the same meaning as those defined in Formula I, where X is a leaving group, specifically Cl, OH, etc.) under conditions with or without a basic reagent to obtain the target product, the compound of Formula I. The compounds represented by Formulas II and III are both commercially available.

[0056]

[0057] Furthermore, the solvent is selected from one or more solvents selected from acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, tetrahydrofuran, dichloromethane, benzene, toluene, xylene, dichloroethane, and ethyl acetate;

[0058] Furthermore, the reaction can be carried out under normal or high pressure, preferably under atmospheric pressure, and post-processing can be performed according to conventional methods.

[0059] The active compounds of formula (I) of this invention are suitable for controlling pests or mites, i.e., pests or mites that are harmful or unwanted, particularly those encountered in agriculture, forestry, storage and material conservation, and sanitation. The compounds of this invention are active against both generally susceptible and resistant species and are effective at all stages of pest or mite development. This invention also relates to methods for inhibiting pests or mites, comprising applying a bioeffective amount of the compound of formula (I) to the insect's location, insect habitat, pest habitat, area under protection, or directly to the insect to be controlled. The compounds of this invention can also be used to control other invertebrate pests or organisms.

[0060] The aforementioned insect habitat, pest habitat, or mite habitat refers to the environment in which insects, pests, or mites live or where their eggs are present, including the surrounding air, the food they consume, or the objects they come into contact with. For example, by applying active compounds to the seeds of plants (before planting), to seedlings, or to planted cuttings, leaves, stems, fruits, grains, and / or roots, or to the soil or other growing media (before or after crop planting), it is possible to control insects or mites that consume, damage, or come into contact with edible agricultural products, ornamental plants, turf, forage plants, or other plants of economic value. It is also possible to protect these plants against diseases caused by viruses, fungi, or bacteria by controlling sap-feeding pests such as whiteflies, planthoppers, aphids, and other insects, or mites such as two-spotted spider mites and carmine spider mites. The plants mentioned include plants propagated through conventional methods, as well as plants genetically modified through modern biotechnology that possess insect or mite resistance, herbicide resistance, high yield, and / or other beneficial characteristics. These compounds are expected to be suitable for protecting fabrics, paper, stored grains, seeds and other foods, houses, buildings and / or places by applying the compounds of the present invention to or near these objects.

[0061] The terms "prevention and control of pests or mites," "control of pests or mites," and "inhibition of pests or mites" all refer to reducing the number of surviving insects, pests, or mites, or reducing the number of viable insect, pest, or mite eggs. The degree of reduction achieved by a compound depends on the application rate of the compound, the specific compound used, and the target insect, pest, or mite species; at least an effective amount must be used.

[0062] The term "mortality rate" refers to an amount sufficient to cause a measurable reduction in the number of treated insects, pests, or mites. Typically, 1 to 1000 ppm (by weight) of the active compound is used. For example, insects or other pests or mites that can be inhibited include, but are not limited to:

[0063] Lepidoptera: Cotton bollworm (Heliothis spp.), cotton bollworm (Helicoverpa spp.), noctuid moth (Spodoptera spp.), armyworm (Mythimna unipuncta), cutworm (Agrotis ipsilon), diamondback moth (Earias spp.), pink-striped noctuid moth (Trichoplusia ni), bean noctuid moth (Anticarsia gemmatalis), mint leafminer (Rachiplusia nu), diamondback moth (Plutella xylostella), rice stem borer (Chilo spp.), rice stem borer (Scirpophaga incertulas), Chinese stem borer (Sesamia inferens), rice leaf roller (Cnaphalocrocismedinalis), corn borer (Ostrinia nubilalis), codling moth (Cydia pomonella), peach fruit moth (Carposina niponensis), cotton brown-banded leafroller (Adoxophyes) Orana, fruit tree yellow leafroller (Archipsargyrospilus), apple brown leafroller (Pandemis heparana), night leafroller (Epinotia aporema), grape and apple leafroller (Eupoecilia ambiguella), grape flower leafroller (Lobesia botrana), Polychrosisbiteana, cotton bollworm (Pectinophora gossypiella), cabbage caterpillar (Pierisrapae), Phyllonorycterspp., spiral leafminer (Leucoptera malifoliella), citrus leafminer (Phyllocnisitis citrella), beet armyworm (Podoptera exigua Hübner);

[0064] Coleoptera: Leaf beetle (Diabrotica spp.), potato leaf beetle (Leptinotarsa ​​decemlineata), rice leaf beetle (Oulema oryzae), boll weevil (Anthonomus grandis), rice water weevil (Lissorhoptrus oryzophilus), wireworm click beetle (Agriotes spp.), Melanotus communis, Japanese beetle (Popillia japonica), genus Cyclocephala (Cyclocephala spp.), flour beetle (Tribolium spp.);

[0065] Hemiptera: Aphids (Aphis spp.), Tobacco Aphid (Myzus Persicae), Rhopalosiphum spp., Plantain Aphid (Dysaphis plantaginea), Citrus Aphid (Toxoptera spp.), Alfalfa Aphid (Aphis craccivora Koch), Euphorbia aphid (Macrosiphum euphorbiae), Eggplant Aphid (Aulacorthum solani), Wheat Aphid (Sitobion avenae), Wheat Aphid (Metopolophium dirhodum), Wheat Aphid (Schizaphis graminum), Wheat Aphid (Brachycolus noxius), Black-tailed Leafhopper (Nephotettix spp.), Brown Planthopper (Nilaparvata lugens), White-backed Planthopper (Sogatella furcifera), Gray Planthopper (Laodelphaxstriatellus), Tobacco Whitefly (Bemisiatabaci), Greenhouse Whitefly (Trialeurodes) Vaporariorum, Aleurodes proletella, Aleurothrixus floccosus, Quadraspidiotus perniciosus, Unaspis yanonenses, Ceroplastes rubens, Aonidiella aurantii;

[0066] Hemiptera: Mirid bug (Lygus spp.), Eurygaster maura, Green rice bug (Nezaraviridula), Piezodorus guildingi, Rice stink bug (Leptocorisa varicornis), Temperate bed bug (Cimexlectularius), Tropical bed bug (Cimex hemipterus);

[0067] Thysanoptera: Western flower thrips (Frankliniella occidentalis), thrips (Thrips spp.), and yellow thrips (Scirtothrips dorsalis);

[0068] Isoptera: *Reticulitermes flavipes*, *Coptotermes formosanus*, *Reticulitermes virginicus*, *Heterotermes aureus*, *Reticulitermes hesperus*, *Coptotermes frenchii*, *Shedorhinotermes spp.*, *Reticulitermes santonensis*, *Reticulitermes grassei*, *Reticulitermes banyulensis*, *Reticulitermes speratus*, *Reticulitermes hageni*, *Reticulitermes tibialis*, *Zootermopsis spp.*, *Incisitermes spp.*, *Marginitermes spp.*, *Macrotermes spp.*, *Microcerotermes* spp.), and savage termites (Microtermes spp.);

[0069] Diptera: Leafminer (Liriomyza spp.), Housefly (Musca domestica), Aedes spp., Culex spp., Anopheles spp., Toilet fly (Fannia spp.), Stomoxys spp.;

[0070] Hymenoptera: Red ants (Iridomyrmex humilis), fire ants (Solenopsis spp.), pharaoh ants (Monomorium pharaonis), Atta spp., harvester ants (Pogonomyrmex spp.), carpenter ants (Camponotus spp.), house ants (Monomorium spp.), stink ants (Tapinoma sessile), pavement ants (Tetramorium spp.), Xylocapa spp., wasps (Vespula spp.), long-legged wasps (Polistes spp.);

[0071] Chachophaga (chewing lice);

[0072] Lice (sucking lice): pubic lice (Pthirus pubis), lice (Pediculus spp.);

[0073] Orthoptera (locusts, crickets): Black locust (Melanoplus spp.), Oriental migratory locust (Locusta migratoria), Desert locust (Schistocerca gregaria), Mole cricket (Gryllotalpidae) (mole crickets);

[0074] Cockroaches (order Blattatus): Oriental cockroach (Blatta orientalis), German cockroach (Blattella germanica), American cockroach (Periplaneta americana), long-bearded cockroach (Supella longipalpa), Australian cockroach (Periplaneta australasiae), brown-spotted cockroach (Periplaneta brunnea), Pennsylvania wood cockroach (Parcoblatta pennsylvanica), black-breasted cockroach (Periplaneta fuliginosa), sugarcane cockroach (Pycnoscelus surinamensis);

[0075] Order Lepidodendron: Fleas (Ctenophalides spp.), Human Fleas (Pulex irritans);

[0076] The order Acari includes the families Tetranychidae, Eupodidae, Eriophyiade, Phytoseiidae, and Acaridae, specifically including but not limited to the following: Tetranychus spp., Panonychus spp., Tetranychus cinnabarinus, Eotetranychus carpini, Tetranychus urticae Koch., Phyllostachys oleivora, Aculus pelekassi, Brevipalpus phoenicis, Boophilus spp., Dermacentorvariabilis, Rhipicephalus sanguineus, Amblyomma americanum, and Ixodes. spp.), feline anal mite (Notoedres cati), scabies mite (Sarcoptes scabiei), dust mite (Dermatophagoides spp.);

[0077] Nematoda: *Dirofilaria immitis*, *Meloidogynes* pp., *Heterodera* spp., *Hoplolaimus columbus*, *Belonolaimus* spp., *Pratylenchus* spp., *Rotylenchus reniformis*, *Criconemella ornata*, *Ditylenchus* spp., *Aphelenchoides besseyi*, and *Hirschmanniella* spp. (rice paddy root nematode).

[0078] The compounds of Formula I of this invention exhibit excellent control effects against various pests and mites even at low concentrations. They possess insecticidal or acaricidal activity at every stage of the pest or mite life cycle (e.g., egg, larva (nymph), pupa, adult). The compounds of Formula I also exhibit excellent control activity against pests and mites that have developed resistance to conventional insecticides or acaricides. The compounds of Formula I can be formulated in various ways based on typical biological and / or chemical physical parameters. Suitable formulation examples include: wettable powders (WP), wettable liquids (SL), soluble powders (SP), dispersible liquids (DC), aqueous solutions (AS), microemulsions (ME), emulsifiable concentrates (EC), water-in-oil emulsions (EW), sprayable solutions, suspensions (SC), oil-dispersible suspensions (OD), powders (DP), microcapsule suspensions (CS), water-dispersible granules (WG), water-soluble granules (SG), large granules (GG), granules for broadcasting and soil application (GR), aerosols (AE), ultra-low volume formulations (ULV), and wax products. Necessary formulation adjuvants include inert substances, surfactants, solvents, and other additives.

[0079] In mixed formulations or tank-mixed formulations, suitable active substances that can be mixed with the active substances of the present invention are, for example, known substances in the Pesticide Handbook (Beijing: Chemical Industry Press, May 2015, 1st edition). For example, the insecticidal active substances mentioned below can be mixed with compounds of Formula I (Note: the name of the compound is either the common name according to the International Organization for Standardization (ISO) or the chemical name, with a code where appropriate): antibiotic insecticides (e.g., allosamidin and Bacillus thuringiensis); macrolide insecticides (e.g., spinosad, spintoram, and other spinosyns including 21-butylspinosadin and their derivatives); avermectin insecticides such as abamectin, doramectin, emamectin, epramectin, ivermectin, and selamectin; mitimectin insecticides such as lepimectin, mitimetris, acaricide oxime, and moxicillin); arsenic-containing insecticides such as calcium arsenate, copper acetylated arsenite, copper arsenate, lead arsenate, potassium arsenite, and sodium arsenite;Biological insecticides include Bacillus popilliae, B. sphaericus, B. thuringiensis subsp. aizawai, B. thuringiensis subsp. kurstaki, B. thuringiensis subsp. tenbrionis, Beauveria bassiana, Cydia pomomella granulosisvirus, Douglas fir tussock moth NPV, Gypsy moth NPV, Helicoverpa zea MPV, and Indiameal moth granulosis virus. Virus), Metarhizium anisopliae, Nosema locustae, Paecilomyces fumosoroseus, P. lilacinus, Photorhabdus luminescens, Spodopteraexigua NPV, trypsin modulating oostatic factor, Xenorhabdus *Nematophilus* and *Xbovienii*, plant-based protective insecticides such as Cry1Ab, Cry1Ac, Cry1F, Cry1A.105, Cry2Ab2, Cry3A, miCry3A, Cry3Bb1, Cry34, Cry35, and VIP3A; plant-based insecticides such as neonicotinoids, azadirachtin, d-limonene, nicotine, pyrethroids, pyrethroid I, pyrethroid II, and jasmine. Ketofenone I, jasminoide II, pyrethroid I, pyrethroid II, quassia, rotenone, ryania, and veratrine); carbamate insecticides such as cypermethrin and carbaryl; benzofuran methyl carbamate insecticides such as carbofuran, decarbofuran, decarbofuran, and furazolidone; dimethyl carbamate insecticides (e.g., dimitan, hyquincarb, and pirimicarb);Oxime carbamate insecticides (e.g., carbaryl, aldicarb, aldisulfiram, methyl ethyl ketone carbide, methyl ethyl ketone carbide, methomyl, cypermethrin, fenvalerate, thiamethoxam, thiamethoxam, thiamethoxam, and chlorpyrifos); phenyl methyl carbamate insecticides (e.g., chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, chlorpyrifos, dicresyl, dicarb, EMPC, ethylbenzyl, fenethacarb, sec-butylcarbide, isoprocarb, methyl thiocarb, chlorpyrifos, zicrolimus, chlorpyrifos, propoxur, chlorpyrifos, XMC, and chlorpyrifos); dinitrophenol insecticides (e.g., chlorpyrifos, propoxur, pentyl nitrate, and DNOC); fluorinated insecticides (e.g., barium hexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicate, and fipronil). Amitraz insecticides (e.g., amitraz, chlorfenapyr, chlorfenapyr, and formparanate); fumigant insecticides (e.g., acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform, chloropicrin, p-dichlorobenzene, 1,2-dichloropropane, ethyl formate, 1,2-dichloroethane, ethylene oxide, hydrogen cyanide, iodomethane, methyl bromide, methyl chloroform, dichloromethane, naphthalene, phosphine, sulfuryl fluoride, and tetrachloroethane); inorganic insecticides (e.g., borax, lime sulfur, copper oleate, mercurous chloride, potassium thiocyanate, and sodium thiocyanate); chitin synthesis inhibitors (e.g., bis(triflufenoxam), thiamethoxam, difenoconazole, cyromazine, diflubenzuron, flufenoxam, flufenoxam, flufenoxam, fenfluramide, novaluron, polyfluorouracil). Flumuron, flufenoxuron, flufenoxuron, and chlorfenapyr; juvenile hormones (e.g., epofenonane, phenoxycarb, tebufenozide, tebufenozide, pyriproxyfenozide, and tebufenozide); juvenile hormones (e.g., juvenile hormone I, juvenile hormone II, and juvenile hormone III); ecdysone agonists (e.g., cyclofenozide, flufenozide, methoxyfenozide, and tebufenozide); ecdysones (e.g., α-ecdysone and ecdysterol); ecdysone inhibitors (e.g., benzyl ether); precocenes (e.g., precocenes I, precocenes II, and precocenes III); insect growth regulators without insect class (e.g., dicyclanil); nereistoxin-like substances. Nereistoxin analogue insecticides (e.g., chlorpyrifos, fenitrothion, chlorpyrifos ring, and thiosultap); neonicotinoid insecticides (e.g., flonicamid); nitroguanidine insecticides (e.g., chlorfenapyr, dinotefuran, imidacloprid, and thiamethoxam); nitromethylene insecticides (e.g., nithiazine and pyridazine); pyridinium methylamine insecticides (e.g., acetamiprid, nitrin, and thiamethoxam); organochlorine insecticides (e.g., bromo-DDT, toxaphene, DDT, pp'-DDT, ethyl-DDT, HCH, γ-HCH, lindane, methoxydendron, pentachlorophenol, and TDE);Cyclodiene insecticides (e.g., aldrin, bromoxynil, borneol, chlordane, chlordecone, dieldrin, dilor, endosulfan, isodrin, HEOD, heptachlor, HHDN, carbapenem, isoamyl, clevafenib, and methamidophos); organophosphate insecticides (e.g., bromfenvinfos, chlorpyrifos, phosmet, dichlorvos, chlorpyrifos, methyl parathion, methyl chlorpyrifos, heptamethrin, methocrotophos, phosmet, dibromophos, naphthiophos, phosphamidon, tebufenozide, TEPP, and chlorpyrifos); organothiophosphate insecticides (e.g., phosmet, phosmet, and chlorpyrifos); aliphatic organothiophosphate insecticides (e.g., phosmet). Aminophosphorus, thion, oxychloride, methyl methamidophos, fenpropathrin, fenpropathrin-O, fenpropathrin-S, demeton-S-methylsulphon, phorate, ethion, phosmet, IPSP, isophorate, malathion, chlorfenapyr, sulfoxide, isosulfoxide, sulfone, phorate, methamidophos, terbufos, terbufos, and methyl phorate; aliphatic amide organothiophosphate insecticides (e.g., cypermethrin, phosmet, dimethoate, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, and phosmet); oxime organothiophosphate insecticides ( Examples include chlorpyrifos, phoxim, and methyl phoxim; heterocyclic organothiophosphate insecticides (e.g., methyl pyrazophos, phosmet, phosmet, dimethoate, phosmet, phosmet, phosmet, pyrazophos, pyrazophos, and quinothion); benzothiaran organothiophosphate insecticides (e.g., duthicrofos and thicrofos); benzotriazine organothiophosphate insecticides (e.g., ethyl glutathione and methyl glutathione); isoindole organothiophosphate insecticides (e.g., chlorimide and chlorpyrifos); isoxazole organothiophosphate insecticides (e.g., oxazolium and zolaprofos); and pyrazolopyrimidine organothiophosphate insecticides. Organothiophosphates (e.g., chlorprazophos and pyraclostrobin); pyridine organothiophosphates (e.g., chlorpyrifos and methyl chlorpyrifos); pyrimidine organothiophosphates (e.g., butathiofos, diazinon, ethiriphos, lirimfos, ethylpyrimidine, methylpyrimidine, primidophos, pyrimidine, and tebupirimfos); quinoxaline organothiophosphates (e.g., quinoxaline and methyl quinoxaline); thiadiazole organothiophosphates (e.g., athidathion, thiazophos, chlorpyrifos, and ethiazophos); triazole organothiophosphates (e.g., chlorpyrifos and triazole).Phenyl organothiophosphate insecticides (e.g., azophos, bromoxynil, ethyl bromoxynil, carbophenothion, chlorpyrifos, fenitrothion, chlorpyrifos, isochlorpyrifos, fenpropathrin, etaphos, valproate, fenitrothion, fenitrothion, fenpropathrin, ethyl fenpropathrin, phosmet, iodophos, nematicide, parathion, methyl parathion, fenpropathrin, parachlorpyrifos, profenofos, profenofos, dithion, trichlormetaphos-3 and trichlorfon); phosphonate insecticides (e.g., butylphosphonate and trichlorfon); phosphonothioate insecticides (e.g., tetramethylphosphonate); phenyl Ethyl thiophosphonate insecticides (e.g., terfenadine and phosphonothion); phenyl thiophosphonate insecticides (e.g., benzonitrile, EPN, and bromophenylphosphonate); phosphoramidate insecticides (e.g., phosphamidon, fenpropathrin, terfenadine, terfenadine, thiophanate-methyl, and pirimetaphos); phosphoramidothioate insecticides (e.g., acephate, methamidophos, isofenphos, methamidophos, and acephate); phosphorodiamide insecticides (e.g., methamidophos, azidophos, promethazine, and octamethrin); oxadiazine insecticides (e.g., indoxacarb). Phthalimide insecticides (e.g., chlorpyrifos, chlorpyrifos, and pyrethroids); pyrazole insecticides (e.g., acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, pyridaben, azoxystrobin, and vaniliprole); pyrethroid insecticides (e.g., flufenacet, allethrin, bio-allethrin, barthrin, bifenthrin, bioethanomethrin, cypermethrin, cypermethrin, lambda-cyhalothrin, β-cyhalothrin, cyhalothrin, γ-cyhalothrin, λ-cyhalothrin, cypermethrin, α-cyhalothrin, ... β-Cypermethrin, θ-Cypermethrin, Zeta-Cypermethrin, Lambda-cypermethrin, Deltamethrin, Tetrafluoromethrin, Cypermethrin, Fenmethrin, Pendiflubenzurin, Pyrimethanil, Cypermethrin, Cypermethrin, Cis-Cypermethrin, Flufenoxuron, Flufenoxuron, Flufenoxuron, Pyrethrin, Profluthrin, Cypermethrin, Cypermethrin, Transpermethrin, Pyrethrin, Profluthrin, Pyresmethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, Cypermethrin, and Cypermethrin.Pyrethroid insecticides (e.g., permethrin, triflufenoxam, fenprofen, protrifenbute, and flumethrin); pyrimidinamine insecticides (e.g., flufenerim and pyrimethanil); pyrrole insecticides (e.g., chlorfenapyr); quinoline insecticides (e.g., spirodiclofen, spirodiclofen); thiourea insecticides (e.g., difenourea); urea insecticides (e.g., flucofuron and sulcofuron); and unclassified insecticides (e.g., AKD-3088, chlorpyrifos, crotonyltoluidine, cyflumetofen, E...). 2Y45, EXD, fenazaquin, fenoxacrim, fenpyroximate, FKI-1033, flubendiamide, HGW86, flufenoxuron, IKI-2002, isoprothiolane, tebufenozide, metaflumizone, pymetrozine, flufenoxuron, NNI-9850, NNI-0101, pymetrozine, pyridaben, acetamiprid, Qcide, iodofensyl, rynaxypyr, SYJ-159, fenpyroximate and abamectin and any combination thereof); and any combination thereof.

[0080] Some fungicides that can be used in combination with the compounds of this invention include: 2-(cyanothiomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, powdery mildew, quisqualis, oxytetracycline, azoxystrobin, Bacillus subtilis, benomyl, benomyl, benzylaminobenzene sulfonate (BABS), bicarbonate, biphenyl, tebuconazole, bifenthrin, borax, Bordeaux mixture, cyazofamid, furazolidone, ethirimol sulfonate, lime sulfur, captan, carbendazim, cyproconazole, carvone, chlorpyrifos, chlorothalonil, ethirimol, scutellaria, copper hydroxide, copper octoate, copper sulfate, basic copper sulfate. Sulfate (tribasic)), cuprous oxide, cyazofamid, syflufenamid, cymoxanil, cyproconazole, pyraclostrobin, dazomet, imazalil, diammonium ethylenebis-(dithiocarbamate)), benzalkonium chloride, dichlorophenol, diclofenac, pyridaben, dichlorofuran, ethoxysulfuron, difenoconazole, difenoconazole, oat calcinate (difenzoquat) (ion), flupyraclostrobin, dimethomorph, fenpropathrin, tebuconazole, tebuconazole-M, acaricide, diphenylamine, dicyandioxonone, morpholine, morpholine acetate, phosmet, phosmet free alkali, difenophosphorus, flutriafol, thiamethoxam, ethoxyquin, tebuconazole, oxadixyl, imidacloprid, chlorpyrifos, fenfuram, cyclophosphamide, cyhalothrin, seed dressing agent, benzyl benzoate, butyl morpholine, triphenyltin, triphenyltin acetate, triphenyltin hydroxide, ferrous sulfate, pyraclostrobin Fluazinam, fluazinam, flumorph, fluazinam, fluchlorothalonil, fluoxastxobin, fluquinazole, flusilazole, sulfadiazine, fluamide, fenbendazole, captan, formaldehyde, tris(ethyl phosphonic acid), aluminum tris(ethyl phosphonate), fenvalerate, furazolidone, furazolidone, biguanidine, biguanidine acetate, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, high-efficiency imazalil, imidazolium, biguanidine octylamine, biguanidine octylamine acetate, iminoctadine tris(albesilate)), succinazole, isoprothiolane, iprodione, isoprothiolane, kasugamycin, kasugamycin hydrochlorideHydrochloridehydrate), azoxystrobin, mancozeb, mancozeb, mancozeb, pyraclostrobin, methamidophos, mercuric chloride, mercuric oxide, mercurous oxide, metalaxyl, metalaxyl-M, high-efficiency metalaxyl, methamidophos, methamidophos-potassium, methamidophos-sodium, tebuconazole, sulfadiazine, methyl iodine, methyl isothiocyanate, mancozeb, fenoxystrobin, benomyl, fenbendazole, cyproconazole, mancozeb sodium, pyraclostrobin, flufenoxuron, octazolone, furazolidone, oleic acid (fatty acid), oxime azoxystrobin, cymoxanil Ling, quinoline copper, oxadiazon fumarate, oxychloride, isoprothiolane, tebuconazole, pendimethalin, pendichlorophenol, pendichlorophenyl laurate, pyraclostrobin, phenylmercuric acetate, phosphonic acid, isoprothiolane, azoxystrobin, polyoxin-B, polyoxin, polyoxin, potassium bicarbonate, potassium hydroxyquinoline sulfate, allylphenthiazide, prochloraz, iprodione, cymoxanil, cymoxanil hydrochloride, propiconazole, propineb, propineb, propoxyquin, propoxyfenozide, prothioconazole, azoxystrobin, pyraclostrobin, barnyardgrass, pyridaben, pyraclostrobin, cymoxanil, quinoline, phenoxyquin, pentachloronitrobenzene, Polygonum cuspidatum sachalinensis extract, silthiamethoxam, silfluzole, sodium 2-phenylphenol, sodium bicarbonate, sodium pentachlorophenol, spirocycline, sulfur, SYP-Z071, tar oil, tebuconazole, tetrachloronitrobenzene, tetraflufenazole, thiamethoxam, thifluzamide, thiophanate-methyl, thiram, thiamethoxam, methyl thiophanate, toluenesulfonamide, triadimefon, triadimefon, imidazolimum, tricyclazole, tridemorph, azoxystrobin, fluopyram, fenazate, cymoxanil, fenazate, fenazate, benzoyl sulfadiazine, vinclozolinone, zineb, thiram, benzoyl sulfadiazine, Candida albicans, Fusarium oxysporum, Phlebiopsis gigantean, Streptomyces glaucus, Trichoderma, (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitrobenzene, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-inel, 1,4,4-tetraoxide, 2-methoxyethylmercuric acetate, 2-methoxyethylmercuric chloride, 2-methoxyethylmercuric silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitropropyl-1-enyl)phenylthiocyanate: aminophosphonic acid, difenoconazole, thiram-methyl bactericide, barium polysulfide, Bayer32394, Benzamacril, quinone oxime hydrazone, cyclohexane, benzamacril; benzamacril-isobutyl, benzamorf, chlorpyrifos, bis(methylmercuric) sulfate, bis(tributyltin) oxide, thiophene, cadmium calcium copper zinc chromate sulfate (cadmium calcium copperzinc) Chromatesulfate), cymoxanil, CECA, chlobenthiazone, chloraniformethan, 2-(2-chlorophenyl)-1H-benzimidazole, chlorfenazole, tetrachloroquinoline, imidacloprid, copper di(3-phenylsalicylic acid)copper, copper zinc chromate, thiophanate-methyl, cuprobam, cyclophosphamide, cyproconazole, esteramide, decanoate, diclofenac, sclerotinyl, benzyltriazol, dimethomorph, chlorpyrifos, nitrocellulose acaricide, nitrobutyl ester, dipyridamole, phosmet, doxorubicin, hydrazine, EBP, ESBP, eticonazole, mancozeb, ethirim, sodium dichloroisocyanurate, imidacloprid, seed dressing ester, triflubenzuron, dimethylfuran, furazolidone, furazolidone, furazolidone, furmecyclox, thiophanate-methyl, glyodine, glycyrrhizin, quinoline acrylate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, o-amide, mecarbinzid, metazoxolon, furazolidone, methylmercurio-cyanamide, thiamethoxam, mancozeb, chloric acid anhydride, methylparaben, N-3,5-dichlorophenyl-succinimide, N-3-nitrophenyl itaconimidide, natamycin, N-ethylmercurio-4-toluenesulfonylaniline, bis(dimethyldithiocarbamate)nickel, OCH, dimethyldithiocarbamate phenylmercuric acid, phenylmercuric nitrate, chlorfenapyr, thiocarb; thiocarb hydrochloride, pyridaben, cyproconazole, chloromethoxypyridine, chlorpyrifos, quinacetol; quinacetol Sulfate, quinconazole, rabenzazole, salicylaniline, SSF-109, pendimethalin, tecoram, thiadifluor, thiochlorfenphim, thiophanate-methyl, chlorpyrifos, tioxymid, cymoxanil, pyraclostrobin, triazole, salicylamide, thiamethoxam, XRD-563, and cyhalothrin, and any mixture thereof.

[0081] Beneficial effects

[0082] Due to the adoption of the above technical solution, the beneficial effects of the present invention are:

[0083] By chemically modifying and molecularly designing compounds with spirocyclic quaternary keto acid structures, pyrazole and polycyclic ring structures were introduced, resulting in a series of more efficient compounds with better crop safety that can be used for insecticidal or acaricidal purposes in agriculture or forestry. These compounds exhibit excellent activity against Lepidoptera, Hemiptera, and Acari (Arachnida), demonstrating excellent control effects against piercing-sucking pests and excellent crop safety.

[0084] Embodiments of the present invention

[0085] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are within the scope of protection of the present invention.

[0086] Based on a comprehensive consideration of the economy, diversity, and bioactivity of the synthesized compounds, some compounds were selected and are listed in the table below. Specific compound structures are shown in Table 1, and specific compound property data are shown in Table 2. The compounds in Tables 1-2 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not understand this to mean that the scope of the above-mentioned subject matter of the present invention is limited to the following compounds.

[0087]

[0088] Table 1 Structures of Compounds of Formula I

[0089]

[0090]

[0091]

[0092]

[0093] Table 2 1 H NMR data

[0094]

[0095]

[0096] The method for preparing the compounds of the present invention is described in the following technical solutions and examples. The raw materials can be purchased commercially or prepared by methods known in the literature or as detailed in the description. Those skilled in the art should 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. Variations or modifications to the preparation method of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation method 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.

[0097] Example 1

[0098] Synthesis of compound I-2:

[0099]

[0100] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-2 (1.84 g, 10 mmol) was added while stirring at 20 °C. DIPEA (1.5 eq) was added while stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the mixture was purified by column chromatography to give a new compound I-2, 2.73 g, white solid powder, melting point: 208 °C. 1 H NMR (500MHz, CDCl3) δ6.83 (s, 2H), 4.10 (t, J = 7.4Hz, 2H), 2.99 (t, J = 7.4Hz, 2H), 2.61 (t, J = 7. 4Hz,2H),2.33(s,3H),2.23(s,3H),2.19(s,6H),2.15(m,2H),2.05(m,4H),1.85–1.80(m,2H).

[0101] Example 2

[0102] Synthesis of compound I-3:

[0103]

[0104] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-3 (1.98 g, 10 mmol) was added while stirring at 20 °C. DIPEA (1.5 eq) was added while stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the product was purified by column chromatography to give a new compound I-3, 2.27 g, white solid powder, melting point: 201 °C. 1 H NMR (500MHz, CDCl3) δ6.82(s,2H),4.11(t,J=7.3Hz,2H),2.98(t,J=7.4Hz,2H),2.85-2.75(q,J=7.4Hz,2H),2.62( t,J=7.3Hz,2H),2.28-2.25(d,J=15.0Hz,9H),2.15(m,2H),2.05(m,4H),1.85–1.80(m,2H),1.07(t,J=8.0Hz,3H).

[0105] Example 3

[0106] Synthesis of compound I-4:

[0107]

[0108] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-4 (2.12 g, 10 mmol) was added while stirring at 20 °C. DIPEA (1.5 eq) was added while stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV color development). After the reaction was complete, the mixture was purified by column chromatography to give a new compound I-4, 2.57 g, white solid powder, melting point: 196 °C. 1 H NMR (500MHz, CDCl3) δ6.85(s,2H),4.08(t,J=7.1Hz,2H),3.51-3.47(m,1H),2.92(t,J=7.3Hz,2H),2.57(s,2H) ,2.27(s,3H),2.23(s,6H),2.10(p,J=7.2Hz,2H),1.92–1.84(m,4H),1.78–1.73(m,2H),1.46(d,J=6.8Hz,6H).

[0109] Example 4

[0110] Synthesis of compound I-22:

[0111]

[0112] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-22 (1.98 g, 10 mmol) was added under stirring at 20 °C. DIPEA (1.5 eq) was added under stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV colorimetric assay). After the reaction was complete, the mixture was purified by column chromatography to give a new compound I-22, 2.17 g, white solid powder, melting point: 180 °C. 1 H NMR (500MHz, CDCl3) δ6.81 (s, 2H), 4.02 (t, J = 5.6Hz, 2H), 2.85 (t, J = 6.3Hz, 2H), 2.28 (s, 3H) ,2.25(s,3H),2.19(s,6H),2.16(s,2H),2.05(m,4H),2.00-1.95(m,2H),1.86-1.81(m,4H).

[0113] Example 5

[0114] Synthesis of compound I-23:

[0115]

[0116] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-23 (2.12 g, 10 mmol) was added under stirring at 20 °C. DIPEA (1.5 eq) was added under stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV colorimetric assay). After the reaction was complete, the mixture was purified by column chromatography to give a new compound I-23, 2.74 g, white solid powder, melting point: 159 °C. 1 H NMR (500MHz, CDCl3) δ6.82(s,2H),4.06(t,J=6.1Hz,2H),2.85(t,J=6.4Hz,2H),2.73(q,J=7.5Hz,2H),2.22(s, 3H), 2.19 (s, 6H), 2.17–2.08 (m, 2H), 2.05 (m, 4H), 2.01–1.97 (m, 2H), 1.86–1.80 (m, 4H), 1.11 (t, J = 7.5Hz, 3H).

[0117] Example 6

[0118] Synthesis of compound I-29:

[0119]

[0120] Intermediate II (2.72 g, 10 mmol) was added to a reaction flask and dissolved in dichloromethane (30 ml). Intermediate III-29 (2.40 g, 10 mmol) was added under stirring at 20 °C. DIPEA (1.5 eq) was added under stirring at 20 °C. The reaction was monitored by TLC (ethyl acetate: petroleum ether = 1:1, GF254, UV colorimetric assay). After the reaction was complete, the mixture was purified by column chromatography to give a new compound I-29, 2.85 g, white solid powder, melting point: 167 °C. 1 H NMR (500MHz, CDCl3) δ6.84(s,2H),4.03(t,J=5.6Hz,2H),2.76(t,J=6.0Hz,2H),2.29(s, 3H),2.27(s,6H),2.12-2.08(m,6H),2.01-1.95(m,2H),1.86–1.81(m,4H),1.51(s,9H).

[0121] Example 7

[0122] Preparation of the formulation:

[0123] 1. Suspension agent: Weigh 24% of compound (Ⅰ), 5% FS3000 (phosphate ester anionic surfactant), 2% NS-500LQ (nonionic hydroxyl polyethylene oxide block copolymer), 0.3% xanthan gum, 1.3% magnesium aluminum silicate, 4% ethylene glycol, 0.1% BIT (1,2-benzisothiazolin-3-one), and 0.2% organic modified siloxane defoamer, add deionized water to 100%, prepare a slurry, and then grind it to obtain the product.

[0124] 2. Water-based emulsion: Weigh 24% of compound (I), 13% xylene, 7% EW-36, and 5% ethylene glycol, add deionized water to 100%, and shear the emulsion using a high-shear emulsifier to obtain the product.

[0125] All figures are weight percentages.

[0126] Bioactivity evaluation

[0127] The test compound was dissolved in N,N-dimethylformamide and then diluted with water containing 0.1% Tween-80 to the required concentration.

[0128] The insecticidal and acaricidal activities of these compounds were tested using *Tetranychus carmineus* and *Tetranychus two-spotted* as targets; and parallel tests of their insecticidal and acaricidal activities were conducted with the following compounds, the specific structures of which are as follows:

[0129] Spirodiclofen (specific structure is) ),

[0130] Spirodiclofen (specific structure is) ),

[0131] As described in compound A (CN101250174B), 3a has the following specific structure: ).

[0132] Example 8

[0133] The activity of the compound of this invention against the eggs of *Tetranychus carinata* was tested using *Tetranychus carinata* as the target. The procedure was as follows: Fresh peanut material with dense planting and large leaves was inoculated with adult mites. After 24 hours, larger leaves with adult mites and reproductive traces were selected. Adult mites on leaves with ≥60 mite eggs were removed. After investigating the number of eggs, the appropriate pesticide was sprayed using a Potter spray tower at a spray pressure of 0.5 kg / cm². 2 The spray volume was 1 ml, and each agent was repeated twice. A blank control (spraying with water) was set up.

[0134] Results investigation: Leaves were kept moist daily. The hatching of mite eggs in the control treatment was observed 3 days after spraying. One day after all eggs in the blank control hatched, the number of unhatched eggs in each treatment was investigated and the hatching inhibition rate was calculated.

[0135] Some test results are as follows:

[0136] When the drug concentration is 100 ppm,

[0137] The hatching rate of *Tetranychus cinnabarinus* eggs was less than 3% 7 days after application of compounds 2-5, 7-10, 17, 22-25, 27-29, 42-49, 62-65, 67-69, 81-84, and 86-87.

[0138] Seven days after application of spirodiclofen and spirodiclofen, the hatching rate of Tetranychus cinnabarin mites was 9% and 6%, respectively.

[0139] The hatching rate of Tetranychus cinnabarinus eggs was higher than 20% 7 days after treatment with compound A.

[0140] Example 9

[0141] Following the above method, some compounds 2, 3, 22, and 23 were selected and compared with known compounds spirodiclofen and spirodiclofen to conduct a control experiment on the inhibitory activity of Tetranychus cinnabarin on hatching eggs. The experimental results are shown in the table below.

[0142] Control test on the inhibitory activity of cinnabar spider mite egg hatching:

[0143]

[0144]

[0145] The above embodiments are merely illustrative of the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the content of the present invention and implement it accordingly. They should not be construed as limiting the scope of protection of the present invention. All equivalent changes or modifications made based on the essence of the content of the present invention should be covered within the scope of protection of the present invention.

Claims

1. A spirodiclofen derivative or a pesticide-acceptable salt thereof, the structural formula of which is shown below: 。 2. An insecticidal or miticidal composition, characterized by comprising Includes at least one of the insecticidal or acaricidal effective amounts of the spirodiclofen derivative of claim 1 or its salts acceptable as pesticides.

3. The insecticidal or acaricidal composition according to claim 2, wherein It also includes formulation carriers or formulation adjuvants.

4. A method for controlling pests or mites, characterized in that, This includes using an effective amount of the spirodiclofen derivative of claim 1 or at least one of its pesticide-acceptable salts, or the insecticidal or acaricidal composition of any one of claims 2-3, on pests or mites and / or their habitats.

5. Use of at least one of the spirodiclofen derivatives of claim 1 or its pesticide-acceptable salts, or the insecticidal or acaricidal compositions of any one of claims 2-3, in the control of pests or mites in agriculture and other fields.

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