Bisamide compound and application thereof

Abstract

The present invention belongs to the field of pesticides, and particularly relates to a bisamide compound or a pesticide acceptable salt, a composition and uses thereof, the compound has a structure represented by a formula (I), and each group in the formula is defined in the specification. The bisamide compound provided by the invention has efficient insecticidal activity, and has excellent safety to crops.

Description

Technical Field

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

[0002] Rice is an important food crop, and the rice planthopper is one of the most serious pests affecting rice production, significantly hindering high and stable yields. Currently, conventional pesticides on the market include pymetrozine, thiamethoxam, imidacloprid, acetamiprid, and dinotefuran, but their promotion and application are hampered by emerging resistance issues. With increasingly stringent requirements for pesticide use, developing more effective insecticides remains a pressing issue. Numerous patents have been reported on aryltriazole compounds, such as CN113597424, CN114728928, CN115023420, CN111989323, and CN109311841, regarding their use in controlling animal pests, including arthropods and insects, as well as their application in controlling ectoparasites. However, the effectiveness of these compounds in controlling animal pests, including arthropods and insects, is not always satisfactory. The general formula and the compound shown in this invention are significantly different from the prior art and have excellent control efficacy against animal pests, including arthropods and insects. Summary of the Invention

[0003] The technical solution adopted by the present invention to achieve the above objectives is: a diamide compound or its salt acceptable as a pesticide, the structural formula of which is shown in formula (I): (I)

[0004] In formula (I), Q is selected from substituted or unsubstituted five- or six-membered aryl or heteroaryl groups, such as phenyl, pyridyl, thiophene, thiazole, pyrazole, pyrrole, and furan.

[0005] R1 is selected from five- or six-membered aryl or heteroaryl groups substituted with substituents, such as phenyl, pyridinyl, thiazolyl, pyrazolyl, pyrroleyl, and pyrimidinyl.

[0006] R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted penta- or hexa-aryl or heteroaryl.

[0007] Preferably, Q is selected from five- or six-membered aryl or heteroaryl groups that are substituted with 1-3 substituents or are not substituted with substituents.

[0008] Preferably, the five- or six-membered aryl or heteroaryl group in R1 is pyridyl, thiophene, or pyrimidinyl.

[0009] Preferably, R2 is selected from C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, substituted or unsubstituted phenyl, pyridyl.

[0010] Further, the five- or six-membered aryl or heteroaryl group in Q is phenyl, pyridyl, pyrazolyl, or thiazolyl; the substituent is selected from F, Cl, Br, I, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OCF3, SCF3, CF3, OCF 2、 CHF2, CH2F, CCl3, CHCl2, CH2Cl, or cyclopropane.

[0011] Furthermore, the five- or six-membered aryl or heteroaryl group in R1 is pyridinyl, thiophene, or pyrimidinyl; and the substituent is H.

[0012] Further, R2 is selected from Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CF3, CHF2, CH2F, CCl3, CHCl2, CH2Cl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and phenyl.

[0013] Furthermore, R2 is selected from Me, Et, CF3, CHF2, cyclopropane, n-Pr, i-Pr, t-Bu, and cyclopentane.

[0014] The pesticide-acceptable salt can be a salt obtained by reacting the diamide compound 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 aryl or heteroaryl substituted m-diamide compound 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.).

[0015] 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.

[0016] The present invention also discloses an insecticidal composition comprising an insecticidal effective amount of at least one of the diamide compounds as described above or their salts acceptable as pesticides; further comprising a formulation carrier or formulation adjuvant.

[0017] The present invention also discloses a method for controlling plant pests, comprising applying an insecticidal effective amount of at least one of the diamide compounds as described above or their pesticide-acceptable salts, or the insecticidal composition as described above, to the crop or the pest and / or its habitat.

[0018] The present invention also discloses the use of at least one of the diamide compounds as described above or their pesticide-acceptable salts, or the insecticidal compositions as described above, in controlling plant pests in agriculture and other fields.

[0019] In the definitions of the above compound structural formulas, the technical terms used all have the following meanings: halogen or halogen refers to: fluorine, chlorine, bromine, iodine.

[0020] 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.

[0021] 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.

[0022] Insecticides containing compounds or their salts represented by formula (I) as active ingredients are suitable for controlling soil pests in the fields of fruit trees, vegetables, other crops and ornamental plants.

[0023] Examples of pests to which the insecticide of this invention can be applied include, but are not limited to, lepidopteran insects, such as small cutworm (Agrotis ypsilon), yellow cutworm (Agrotis segetum), cotton beetle (Alabama argillacea), bean leafroller (Anticarsiagemmatalis), Argyresthia conjugella, forked leafroller (Autographa gamma), tree looper (Bupaluspiniarius), Cacoecia murinana, Capua reticulana, Cheimatobiabrumata, spruce leafroller (Choristoneura fumiferana), Choristoneura occidentalis, rice stem borer (Cirphis unipuncta), apple leafroller (Cydia pomonella), pine caterpillar (Dendrolimus pini), Diaphanianitidalis, southwestern corn stalk borer (Diatraea grandiosella), Egyptian leafminer (Eariasinsulana), and South American corn seedling borer (Elasmopalpus). lignosellus), privet leafroller (Eupoecilia ambiguella), evetria bouliana, feltia subterranea, wax moth (Galleria mellonella), plum fruit moth (Grapholitha funebrana), pear fruit moth (Grapholitha molesta), cotton bollworm (Heliothis armigera), tobacco bud borer (Heliothis virescens), corn ear borer (Heliothis zea), cabbage borer (Hellulaundalis), hibernia defoliaria, fall webworm (Hyphantria cunea), apple leafminer (Hyponomeutamalinellus), tomato leafminer (Keiferia lycopersicella), lambdinafiscellaria, beet armyworm (Laphygma exigua), coffee leafminer (Leucoptera coffeella), spiral leafminer (Leucopterascitella), Lithocolletis blancardella, grape berry leafroller (Lobesiabotrana), beet lace borer (Loxostege)sticticalis, gypsy moth (Lymantria dispar), tussock moth (Lymantria monacha), peach leafminer (Lyonetia clerkella), yellow tent caterpillar (Malacosomaneustria), cabbage cutworm (Mamestrabrassicae), yew tussock moth (Orgyia pseudotsugata), corn borer (Ostrinia nubilalis), small-eyed cutworm (Panolis flammea), cotton bollworm (Pectinophoragossypiella), burrowing cutworm (Peridromasaucia), round-handled boat moth (Phalera bucephala), potato leafminer (Phthorimaea operculella), citrus leafminer (Phyllocnistis citrella), European white butterfly (Pieris brassicae), alfalfa green cutworm (Plathypena scabra), diamondback moth (Plutella xylostella), soybean cutworm (Pseudoplusia includens), Rhyacionia frustrana, Scorobipalpula absoluta, wheat moth (Sitotrogacerealella), grape leafroller (Sparganothis pilleriana), meadow noctuid moth (Spodopterafrugiperda), sea gray-winged noctuid moth (Spodoptera littoralis), beet armyworm (Spodopteralitura), Thaumatopoea pityocampa, green oak moth (Tortrix viridana), pink noctuid moth (Trichoplusiani), and Zeiraphera canadensi.

[0024] Bed bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera, such as the green stink bug (Acrosternum hilare), corn stink bug (Blissus leucopterus), black-spotted smoke stink bug (Cyrtopeltisnotatus), cotton red stink bug (Dysdercus cingulatus), Dysdercus intermedius, wheat flat shield stink bug (Eurygaster integriceps), tobacco stink bug (Euschistus impictiventris), cotton red bell beak stink bug (Leptoglossus phyllopus), American pasture stink bug (Lygus lineolaris), pasture stink bug (Lyguspratensis), rice green stink bug (Nezara viridula), beet lace stink bug (Piesma quadrata), Solubeainsularis, Thyanta perditor, Acyrthosiphon) *Aphis onobrychis*, *Adelgeslaricis*, *Aphidula nasturtii*, *Aphis fabae*, *Aphis forbesi*, *Aphis pomi*, *Aphis gossypii*, *Aphis grossulariae*, *Aphis schneideri*, *Aphis spiraecola*, *Aphis sambuci*, *Acyrthosiphonpisum*, *Aulacorthum solani*, *Bemisia argentifolii*, *Brachycaudus cardui*, *Brachycaudus helichrysi*, *Brachycaudus persicae*, *Brachycaudus prunicola*, *Brevicoryne brassicae*, *Capitophorus horni*, *Cerosipha* gossypii, Chaetosiphon fragaefolii, Cryptomyzusribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthumpseudosolani, Dysaphisplantaginea, Dysaphispyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzuslactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus Donc, Myzuscerasi, Myzus varians, Nasonoviaribis-nigri, Nilaparvatalugens, Pemphigus bursarius, Perkinsiella The following aphids are listed: saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphummaidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduviussenilis, Triatoma spp., and Arilus critatus.

[0025] Beetles (Coleoptera), such as the pear beetle beetle (Agrilus sinuatus), straight click beetle (Agriotes lineatus), dark click beetle (Agriotes obscurus), Amphimallus solstitialis, Anisandrus dispar, Mexican boll weevil (Anthonomus grandis), apple flower weevil (Anthonomus pomorum), Aphthona euphoridae, Athous haemorrhoidalis, beet beetle beetle (Atomaria linearis), pit beetle (Blastophagus piniperda), Blitophaga undata, bean weevil (Bruchus rufimanus), pea weevil (Bruchus pisorum), European bean weevil (Bruchus lentis), apple roller weevil (Byctiscus betulae), beet beetle beetle (Cassida nebulosa), Cerotoma trifurcata, and golden flower beetle (Cetonia). aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp.The following species are listed: Longhorned Leaf Beetle (Diabrotica longicornis), Semipunctata (Diabrotica semipunctata), 12-punctata (Diabrotica 12-punctata), South American Leaf Beetle (Diabrotica speciosa), Corn Root Leaf Beetle (Diabrotica virgifera), Mexican Bean Ladybug (Epilachna varivestis), Tobacco Flea Beetle (Epitrix hirtipennis), Cotton Gray Weevil (Eutinobothrus brasiliensis), European Pine Bark Weevil (Hylobius abietis), Egyptian Alfalfa Leaf Weevil (Hypera brunneipennis), Purple Alfalfa Leaf Weevil (Hypera postica), Spruce Bark Beetle (Ipstypographus), Tobacco Leaf Beetle (Lema bilineata), Black Horned Leaf Beetle (Lema melanopus), Potato Leaf Beetle (Leptinotarsa ​​decemlineata), Limonius californicus, Rice Water Weevil (Lissorhoptrusoryzophilus), Melanotus communis, rapeseed beetle (Meligethes aeneus), large chestnut beetle (Melolontha hippocastani), May beetle (Melolontha melolontha), rice leaf beetle (Oulemaoryzae), grape black-eared beetle (Ortiorrhynchus sulcatus), strawberry root weevil (Otiorrhynchusovatus), horseradish leaf beetle (Phaedon cochleariae), Phyllobius pyri, Phyllotretachrysocephala, leaf-eating beetle (Phyllophaga sp.), garden dwarf beetle (Phyllopertha horticola), soybean flea beetle (Phyllotreta nemorum), yellow flea beetle (Phyllotretastriolata), Japanese scarab beetle (Popillia japonica), pea leaf weevil (Sitonalineatus), and grain weevil (Sitophilus granaria).

[0026] Flies and mosquitoes (Diptera), such as Aedes aegypti, Aedes albopictus, Aedes vexans, Anatrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles salbimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomyabezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops Silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culisetamelanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Delia antique, Delia coarctata, Delia platura, Delia radicum, Dermatobia hominis, Fannia canicularis, Geomyza tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossinafuscipes, Glossinatachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., peanut field maggot (Hylemyia platura), striped leaf fly (Hypoderma lineata), Leptoconops torrens, vegetable leafminer (Liriomyza sativae), American leafminer (Liriomyza trifolii), Lucilia caprina, copper green fly (Lucilia cuprina), silky green fly (Lucilia sericata), Lycoria pectoralis, Mansoniatitillanus, wheat gall midge (Mayetiola destructor), autumn housefly (Musca autumnalis), housefly (Musca domestica), stable rot fly (Muscina stabulans), sheep mad fly (Oestrus ovis), Opomyza florum, European straw fly (Oscinella frit), henbane fly (Pegomya) hysocyami), Phorbiaantiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophoracolumbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga, Simulium vittatum, Stomoxyscalcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, Tabanus similis, Tipula oleracea, and Tipula paludosa.

[0027] Thrips (order Thysanoptera), such as orchid thrips (Dichromothrips corbetti), Dichromothrips ssp, brown thrips (Frankliniella fusca), alfalfa thrips (Frankliniella occidentalis), oriental flower thrips (Frankliniella tritici), bellflower thrips (Scirtothrips citri), rice thrips (Thrips oryzae), palm thrips (Thrips palmi), and tobacco thrips (Thrips tabaci).

[0028] Termites (Isoptera), such as Calotermes flavicollis, Leucotermesflavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus.

[0029] Cockroaches (Blattaria-Blattodea), such as the German cockroach (Blattella germanica), Blattella asahinae, American cockroach (Periplaneta americana), Japanese cockroach (Periplaneta japonica), brown cockroach (Periplaneta brunnea), Periplaneta fuligginosa, Australian cockroach (Periplaneta australasiae), and oriental cockroach (Blatta orientalis).

[0030] Ants, bees, wasps, and sawflies (Hymenoptera), such as the Xinjiang cabbage wasp (Athaliarosae), leafcutter ants (Atta cephalotes), Atta capiguara, Atta cephalotes, Attalaevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster, Hoplocampaminuta, Hoplocampa testudinea, black hairy ants (Lasius niger), small yellow house ants (Monomoriumpharaonis), tropical fire ants (Solenopsis geminata), red fire ants (Solenopsis invicta), black fire ants (Solenopsis richteri), southern fire ants (Solenopsis xyloni), red ants (Pogonomyrmex barbatus), Pogonomyrmex californicus, big-headed ants (Pheidolemegacephala), and velvet ants (Dasymutilla). The genera include *Occidentalis*, *Bombus*, *Vespula squamosa*, *Paravespula vulgaris*, *Paravespula pennsylvanica*, *Paravespula germanica*, *Dolichovespula maculata*, *Vespa crabro*, *Polistes rubiginosa*, *Campodontus floridanus*, and *Linepithema humile*.

[0031] Crickets, grasshoppers, and locusts (Orthoptera), such as the house cricket (Acheta domestica), mole cricket (Gryllotalpa gryllotalpa), migratory locust (Locusta migratoria), two-striped black locust (Melanoplus bivittatus), red-legged black locust (Melanoplus femurrubrum), Mexican black locust (Melanoplus mexicanus), migratory black locust (Melanoplus sanguinipes), rock-dwelling black locust (Melanoplusspretus), striped red locust (Nomadacris septemfasciata), American desert locust (Schistocerca americana), African desert locust (Schistocerca gregaria), Moroccan locust (Dociostaurus maroccanus), house katydid (Tachycines asynamorus), Senegalese small car locust (Oedaleus senegalensis), and stink gland locust (Zonozerus). variegatus), Hieroglyphus daganensis, Kraussaria angulifera, Italian locust (Calliptamus italicus), Australian locust (Chortoicetes terminifera), and brown locust (Locustana pardalina).

[0032] Arachnoidea, such as red spiders (Acari order Acarina), including families like Argasidae, Ixodidae, and Sarcoptidae, such as the long-spotted tick (Amblyomma americanum), tropical flower tick (Amblyomma variegatum), Ambryomma maculatum, Persian sharp-edged tick (Argas persicus), cattle tick (Boophilus annulatus), Boophilus decoloratus, small cattle tick (Boophilus microplus), Dermacentor silvarum, Dermacentor andersoni, American large-footed tick (Dermacentor variabilis), Hyalomma truncatum, castor tick (Ixodes ricinus), Ixodes rubicundus, black-legged tick (Ixodes scapularis), and perianth tick (Ixodes...). The following mites are listed: *Holocyclus*, *Ixodes pacificus*, *Ornithodorus moubata*, *Ornithodorus hermsi*, *Ornithodorusturicata*, *Ornithonyssus bacoti*, *Otobius megnini*, *Dermanyssus gallinae*, *Psoroptes ovis*, *Rhipicephalus sanguineus*, *Rhipicephalus appendiculatus*, *Rhipicephalus evertsi*, *Sarcoptes scabiei*, and *Eriophyidae*, such as *Aculus schlechtendali*, *Phyllocoptrataoleivora*, and *Eriophyes sheldoni*; and *Tarsonemidae*, such as *Phytonemus*. pallidus and Polyphagotarsonemuslatus; Tenuipalpidae, such as Brevipalpus phoenicis;Spider mites (Tetranychidae), such as *Tetranychus cinnabarinus*, *Tetranychus kanzawai*, *Tetranychus pacificus*, *Tetranychus telarius*, and *Tetranychus urticae*, as well as *Panonychus ulmi*, *Panonychus citri*, and *Oligonychus pratensis*; and spiders (Araneida), such as *Latrodectus mactans* and *Loxosceles reclusa*.

[0033] Fleas (order Siphonaptera), such as cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), rat fleas (Xenopsylla cheopis), itch fleas (Pulex irritans), skin-penetrating fleas (Tunga penetrans), and disease-carrying fleas (Nosopsyllus fasciatus).

[0034] Silverfish, including domestic silverfish (Thysanura), such as Lepisma saccharina and Thermobia domestica; centipedes (Chilopoda), such as Scutigera coleoptrata; millipedes (Diplopoda), such as Narcesus spp.; earwigs (Dermaptera), such as forficula auricularia; lice (Phthiraptera), such as Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinuseurysternus, Haematopinus suis, Linognathus vitiligoi, Bovicolabovis, and Menopon gallinae), Menacanthus stramineus and Solenopotes capillatu.

[0035] Collembola (springtails), for example, the genus Onychiurus.

[0036] They are also suitable for controlling nematodes: plant parasitic nematodes such as root-knot nematodes, including the northern root-knot nematode (Meloidogynehapla), the southern root-knot nematode (Meloidogyne incognita), the Javan root-knot nematode (Meloidogyne javanica), and other root-knot nematodes of the genus Meloidogyne; cyst-forming nematodes, such as the potato golden nematode (Globodera arostochiensis) and other globodera cyst nematodes; cereal cyst nematodes (Heterodera avenae), soybean cyst nematodes (Heterodera glycines), beet cyst nematodes (Heterodera schachtii), and clover cyst nematodes (Heterodera... *Trifolii* and other cyst nematodes (*Heterodera*); seed gall nematodes, *Anguina*; stem and leaf nematodes, *Aphelenchoides*; stinging nematodes, *Belonolaimus longicaudatus* and other needle-stinging nematodes (*Belonolaimus*); pine nematodes, *Bursaphelenchus xylophilus* and other *Bursaphelenchus*; annular nematodes, *Criconema*, *Criconemella*, *Criconemoides*, *Mesocriconema*; bulb nematodes, *Ditylenchus destructor*, sweet potato stem nematode (*Ditylenchus*). (dipsaci) and other stem nematodes (Ditylenchus); trypanosomes (Dolichodorus); spiral nematodes (Heliocotylenchus multicinctus and other Helicotylenchus); sheath nematodes and sheath-shaped nematodes (Hemicycliophora and Heemicriconemoides); root-burrowing nematodes (Hirshmanniella); crown nematodes (Hoplolaimus); pseudo-root-knot nematodes (Nacobbus); needle nematodes (Longidorus elongatus and other Longidorus).Root-rot nematodes: *Pratylenchus neglectus*, *Pratylenchus spenetrans*, *Pratylenchus curvitatus*, *Pratylenchus goodeyi*, and other *Pratylenchus* species; Perforating nematodes: *Radopholus similis*, and other *Radopholus* species; Kidney-shaped nematodes: *Rotylenchus robustus*, and other *Rotylenchus* species; *Scutellonema* genus; Residual root nematodes: *Trichodorus primitivus*, and other *Trichodorus* species; *Paratrichodorus* genus; Growth-blocking nematodes: *Tylenchorhynchus claytoni*, *Tylenchorhynchus* (both compliant and resistant varieties). *Dubius* and other dwarfing nematodes (*Tylenchorhynchus*); citrus nematodes, *Tylenchulus*; xiphinema nematodes; and other plant-parasitic nematodes.

[0037] The plant species used in the insecticide of this invention are not particularly limited; examples include, for instance, cereals (e.g., rice, barley, wheat, rye, oats, corn, sorghum, etc.), legumes (soybeans, mung beans, broad beans, peas, peanuts, etc.), fruit trees / fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, apricots, bananas, strawberries, etc.), vegetables (cabbage, tomatoes, spinach, cabbage, lettuce, onions, scallions, green peppers, etc.), and root vegetables (carrots, potatoes, sweet potatoes, etc.). Radishes, lotus roots, and wild grasses, etc.), industrial crops (cotton, paper mulberry, daphne, rapeseed, sugar beets, hops, sugarcane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), berries (pumpkin, cucumber, watermelon, melon, etc.), forage grasses (orchard grass, sorghum, timothy grass, alfalfa, purple alfalfa, etc.), turfgrass (Korean zoysia grass, creeping bentgrass, etc.), spice crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), and flowers (chrysanthemums, roses, orchids, etc.).

[0038] Beneficial Effects: Due to the adoption of the above technical solutions, the beneficial effects of this invention are as follows: By chemically modifying and molecularly designing compounds with diamide structures, a triazole structure is introduced onto the heterocycle, thereby obtaining a series of more efficient compounds with excellent activity that can be used for insecticidal purposes in agriculture or forestry, especially exhibiting rapid and long-lasting insecticidal activity at low doses.

[0039] The embodiments of the present invention will be described clearly and completely 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.

[0040] 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 Table 1 are only for better illustration of the present invention and are not intended to 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.

[0041]

[0042] In the structure shown in Equation I, the specific structure and 1 The H NMR spectra are shown in Table 1: Serial Number Q <![CDATA[R1]]> <![CDATA[R2]]> <![CDATA[ 1 H NMR]]> I-1 3-Chloro-5-trifluoromethylphenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO- d 6)δ 10.63 (s,1H), 9.58 (d, J = 6.8 Hz,1H), 8.98 (m,1H), 8.85 (s,1H), 8.46 (s,2H), 8.32 (s,1H),7.59 (d, J = 5.0 Hz,1H), 6.02 (m,1H), 2.08 (s,3H), 1.68 (d, J =6.9 Hz,3H). <!-- 8 -->]]> I-2 3,5-Bistrifluoromethylphenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 10.62 (s,1H), 9.56 (d,J = 6.8 Hz,1H), 8.95 (d,J = 4.8 Hz,2H), 8.44 (s,2H), 8.30 (s,1H), 7.58(d,J = 5.0 Hz,1H), 6.02 (m,1H), 2.07 (s,3H), 1.67 (d,J = 6.9 Hz,3H).]]> I-3 3,5-Dibromophenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 10.60 (s,1H), 9.64 (d,J = 6.8 Hz,1H), 8.99 (d,J = 4.8 Hz,2H), 8.48 (s,2H), 8.34 (s,1H), 7.57(d,J = 5.0 Hz,1H), 6.03 (m,1H), 2.07 (s,3H), 1.69 (d,J = 6.9 Hz,3H). <!-- 9 -->]]> I-4 3,5-Dichlorophenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 10.61 (s,1H), 9.65 (d,J = 6.8 Hz,1H), 8.98 (d,J = 4.8 Hz,2H), 8.49 (s,2H), 8.35 (s,1H), 7.58(d,J = 5.0 Hz,1H), 6.01 (m,1H), 2.08 (s,3H), 1.69 (d,J = 6.9 Hz,3H).]]> I-5 3-Fluoro-5-trifluoromethylphenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 10.63 (s,1H), 9.57 (d,J = 6.8 Hz,1H), 8.99 (m,1H), 8.86 (s,1H), 8.47 (s,2H), 8.31 (s,1H), 7.60 (d,J = 5.0 Hz,1H), 6.02 (m,1H), 2.07 (s,3H), 1.67 (d,J =6.9 Hz,3H). <!-- 10 -->]]> I-6 3-Bromo-5-trifluoromethylphenyl Pyrimidine-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 10.60 (s,1H), 9.59 (d,J = 6.8 Hz,1H), 8.97 (m,1H), 8.85 (s,1H), 8.45 (s,2H), 8.32 (s,1H), 7.59 (d,J = 5.0 Hz,1H), 6.02 (m,1H), 2.08 (s,3H), 1.66 (d,J =6.9 Hz,3H).]]> I-7 3-Chloro-5-trifluoromethylphenyl Pyrimidin-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.39 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.04 (d,J = 4.9 Hz,2H), 8.49 (t,J = 1.7 Hz,1H),8.36 (m,1H), 8.34 (s,1H), 7.65 (t,J = 4.8 Hz,1H), 6.03 (m,1H), 1.71 (d,J = 7.0 Hz,3H). <!-- 11 -->]]> I-8 3,5-Bistrifluoromethylphenyl Pyrimidine-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 9.00 (d,J = 4.9 Hz,2H), 8.43 (d,J = 1.7 Hz,2H), 8.32 (s,1H), 7.64 (t,J = 4.8 Hz,1H), 6.03 (m,1H), 1.70 (d,J = 7.0 Hz, 3H).]]> I-9 3,5-Dibromophenyl Pyrimidine-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.41 (s,1H), 9.63 (d,J = 6.7 Hz,1H), 9.03 (d,J = 4.9 Hz,2H), 8.50 (d,J = 1.7 Hz,2H), 8.35 (s,1H), 7.63 (t,J = 4.8 Hz,1H), 6.02 (m,1H), 1.71 (d,J = 7.0 Hz, 3H). <!-- 12 -->]]> I-10 3,5-Dichlorophenyl Pyrimidine-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.41 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.04 (d,J = 4.9 Hz,2H), 8.51 (d,J = 1.7 Hz,2H), 8.36 (s,1H), 7.62 (t,J = 4.8 Hz,1H), 6.02 (m,1H), 1.72 (d,J = 7.0 Hz, 3H).]]> I-11 3-Fluoro-5-trifluoromethylphenyl Pyrimidine-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 9.02 (d,J = 4.9 Hz,2H), 8.49 (t,J = 1.7 Hz,1H),8.37 (m,1H), 8.33 (s,1H), 7.65 (t,J = 4.8 Hz,1H), 6.03 (m,1H), 1.71 (d,J = 7.0 Hz,3H). <!-- 13 -->]]> I-12 3-Bromo-5-trifluoromethylbenzene Pyrimidine-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.39 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.04 (d,J = 4.9 Hz,2H), 8.49 (t,J = 1.7 Hz,1H),8.38 (m,1H), 8.34 (s,1H), 7.64 (t,J = 4.8 Hz,1H), 6.00 (m,1H), 1.70 (d,J = 7.0 Hz,3H).]]> I-13 3-Chloro-5-trifluoromethylphenyl Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.39 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.04 (d,J = 4.9 Hz,2H), 8.49 (t,J = 1.7 Hz,1H),8.38 (m,1H), 8.34 (s,1H), 7.64 (t,J = 4.8 Hz,1H), 7.34 (t,J = 57.3 Hz,1H), 6.00 (m,1H), 1.70 (d,J = 7.0 Hz,3H). <!-- 14 -->]]> I-14 3,5-Bistrifluoromethylphenyl Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.38 (s,1H), 9.59 (d,J = 6.7 Hz,1H), 9.00 (d,J = 4.9 Hz,2H), 8.42 (d,J = 1.7 Hz,2H), 8.30 (s,1H), 7.62 (t,J = 4.8 Hz,1H), 7.35 (t,J = 57.3 Hz,1H), 6.03 (m,1H), 1.71 (d,J = 7.0 Hz,3H).]]> I-15 3,5-Dibromobenzene Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.41 (s,1H), 9.63 (d,J = 6.7 Hz,1H), 9.03 (d,J = 4.9 Hz,2H), 8.50 (d,J = 1.7 Hz,2H), 8.35 (s,1H), 7.63 (t,J = 4.8 Hz,1H), 7.34 (t,J = 57.3 Hz,1H), 6.02 (m,1H), 1.71 (d,J = 7.0 Hz,3H). <!-- 15 -->]]> I-16 3,5-Dichlorophenyl Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.43 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.00 (d,J = 4.9 Hz,2H), 8.51 (d,J = 1.7 Hz,2H), 8.38 (s,1H), 7.62 (t,J = 4.8 Hz,1H), 7.34 (t,J = 57.3 Hz,1H), 6.04 (m,1H), 1.72 (d,J = 7.0 Hz,3H).]]> I-17 3-Fluoro-5-trifluoromethylphenyl Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 9.02 (d,J = 4.9 Hz,2H), 8.48 (t,J = 1.7 Hz,1H),8.37 (m,1H), 8.33 (s,1H), 7.65 (t,J = 4.8 Hz,1H), 7.34 (t,J = 57.3 Hz,1H), 6.03 (m,1H), 1.69 (d,J = 7.0 Hz,3H). <!-- 16 -->]]> I-18 3-Bromo-5-trifluoromethylphenyl Pyrimidine-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.39 (s,1H), 9.62 (d,J = 6.7 Hz,1H), 9.04 (d,J = 4.9 Hz,2H), 8.49 (t,J = 1.7 Hz,1H),8.38 (m,1H), 8.34 (s,1H), 7.64 (t,J = 4.8 Hz,1H),7.33 (t,J = 57.3 Hz,1H), 6.00 (m,1H), 1.70 (d,J = 7.0 Hz,3H).]]> I-19 3,5-Bistrifluoromethylphenyl Pyridin-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 8.51( d,J = 4.1Hz, 1H)8.43 (d, J =1.7 Hz, 2H),8.32 (s,1H),8.05 (m, 1H),7.90 (d, J =6.7 Hz, 1H )7.44 (m, 1H),6.03 (m, 1H),2.08 (s, 3H),1.66 (d, J =6.9 Hz, 3H). <!-- 17 -->]]> I-20 3-Bromo-5-trifluoromethylphenyl Pyridin-2-yl methyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.38 (s,1H), 9.62 (d,J = 6.8 Hz,1H) , 8.53(d, J = 4.3Hz,1H ), 8.44(d, J = 1.7Hz, 2H), 8.33(s,1H), 8.06(m, 1H), 7.92(d, J = 6.9Hz, 1H )7.46(m, 1H), 6.03(m, 1H), 2.08(s, 3H), 1.66(d, J =6.9Hz, 3H).]]> I-21 3,5-Bistrifluoromethylphenyl Pyridin-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 8.51( d,J = 4.1Hz, 1H)8.43 (d, J =1.7 Hz, 2H),8.32 (s,1H),8.05 (m, 1H),7.90 (d, J =6.7 Hz, 1H )7.44 (m, 1H),6.03 (m, 1H),1.70 (d, J =7.0 Hz, 3 H). <!-- 18 -->]]> I-22 3-Bromo-5-trifluoromethylphenyl Pyridin-2-yl Trifluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.38 (s,1H), 9.62 (d,J = 6.8 Hz,1H), 8.53( d,J = 4.3Hz, 1H), 8.44 (d, J= 1.7 Hz,2H), 8.33 (s,1H), 8.06 (m,1H), 7.92 (d,J = 6.9 Hz,1H )7.46 (m,1H), 6.03 (m,1H), 1.70 (d,J = 7.0 Hz, 3H).]]> I-23 3,5-Bistrifluoromethylphenyl Pyridin-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.40 (s,1H), 9.61 (d,J = 6.7 Hz,1H), 8.51( d,J = 4.1Hz, 1H)8.43 (d, J =1.7 Hz, 2H),8.32 (s,1H),8.05 (m, 1H),7.90 (d, J =6.7 Hz, 1H ),7.65 (t, J =4.8 Hz, 1H),7.34 (t, J =57.3 Hz, 1H),6.03 (m, 1H),1.70 (d, J =7.0 Hz, 3 H). <!-- 19 -->]]> I-24 3-Bromo-5-trifluoromethylphenyl Pyridin-2-yl difluoromethyl <![CDATA[ 1 H NMR (400MHz, DMSO-d6)δ 12.38 (s,1H), 9.62 (d,J = 6.8 Hz,1H) , 8.53(d, J = 4.3Hz,1H ), 8.44(d, J = 1.7Hz, 2H), 8.33(s,1H), 8.06(m, 1H), 7.92(d, J = 6.9Hz, 1H ),7.65 (t, J =4.8 Hz, 1H),7.34 (t, J =57.3 Hz, 1H),6.03 (m, 1H),1.70 (d, J =7.0 Hz, 3 H).]]>

[0043] 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.

[0044] Example 1

[0045] Preparation of compound I-1:

[0046] (1) Preparation of VI-1:

[0047] Intermediate VII-1 is commercially available.

[0048] Intermediate VII-1 (90.1 mmol, 17.11 g) was dissolved in 250 mL of tetrahydrofuran and added to a dry 500 mL single-necked flask. Phthaloyl-L-alanine (90.1 mmol, 19.73 g), HATU (90.1 mmol, 34.24 g), and triethylamine (180.2 mmol, 18.2 g) were added with stirring at room temperature (25 °C). After the addition was complete, the reaction mixture was transferred to an 80 °C oil bath and reacted for 2 h. The reaction was monitored by LS-MS. After the reaction was complete, the solvent was removed under reduced pressure, 400 mL of ethyl acetate was added, and the mixture was extracted three times with 200 mL of saturated brine. After drying, the mixture was separated by silica gel column chromatography (development ratio: petroleum ether: ethyl acetate = 15:1) to give intermediate VI-1 (24.72 g, 70.17%), which was a pale yellow oily liquid.

[0049] (2) Preparation of V-1:

[0050] The intermediate VI-1 (24.72 g) obtained in the previous step was dissolved in 250 mL of pyridine and added to a dry 500 mL single-necked flask. 2-Hydroxypyrimidine (63.22 mmol, 6.95 g) was added to the reaction system with stirring at room temperature (25 °C). After the addition was complete, the reaction mixture was transferred to an 80 °C oil bath and reacted for 6 h. The reaction was monitored by LS-MS. After the reaction was complete, the solvent was removed under reduced pressure, 400 mL of ethyl acetate was added, and the mixture was extracted three times with 200 mL of saturated brine, twice with 200 mL of dilute hydrochloric acid, and twice with 200 mL of water. The extract was dried over anhydrous sodium sulfate and filtered. The solution was concentrated under reduced pressure to obtain intermediate V-1 (27.1 g, 98.86% yield), a pale yellow solid.

[0051] (3) Preparation of IV-1:

[0052] The intermediate V-1 (27.19 g) obtained in the previous step was dissolved in 250 mL of ethanol and added to a dry 500 mL single-necked flask. Under stirring at room temperature (25 °C), 80% hydrazine hydrate (187.5 mmol, 11.72 g) was added to the reaction system. After the addition was complete, the reaction mixture was transferred to an 80 °C oil bath and reacted for 1.5 h. The reaction was monitored by LS-MS. After the reaction was complete, the mixture was filtered, dissolved under reduced pressure, and then separated by silica gel column chromatography (development ratio of ethyl acetate:methanol = 5:1) to obtain intermediate IV-1 (15.16 g, 79.52%), which was a white solid.

[0053] (5) Preparation of III-1

[0054] 3-Chloro-5-trifluoromethylbenzoic acid (49.7 mmol, 11.16 g) was dissolved in 250 mL of dichloromethane and added to a dry 500 mL single-necked flask. HATU (49.7 mmol, 18.89 g) and DIPEA (54.67 mmol, 7.05 g) were added with stirring at room temperature (25 °C). After reacting for 0.5 h, intermediate IV-1 (15.16 g) obtained in the previous step was added to the reaction system, and stirring continued at room temperature (25 °C). The reaction was monitored by LS-MS. After the reaction was complete, the sample was extracted three times with 200 mL of saturated brine, and then separated by silica gel chromatography (petroleum ether:ethyl acetate = 1:2) after drying to obtain intermediate III-1 (23.44 g, 92.29%), which was a white solid.

[0055] (6) Preparation of compound II-1:

[0056] Intermediate III-1 (23.44 g) obtained in the previous step was dissolved in a mixed solution of dichloromethane and trifluoroacetic acid (3:1) and added to a dry 500 mL single-necked flask. The mixture was stirred at room temperature (25 °C) for 12 h, and the reaction was monitored by LS-MS. After the reaction was completed, the solvent was removed under reduced pressure, and the product was separated by silica gel column chromatography (development ratio of ethyl acetate:methanol = 20:1) to obtain intermediate II-1 (10.43 g, 55.35%), which was a white solid.

[0057] (7) Preparation of compound I-1:

[0058] In a dry 100 mL single-necked flask, 45 mL of dry tetrahydrofuran and 25 mmol (1.0 g) of 60% NaH were added. Intermediate VI (10 mmol, 4.11 g) was added at 0 °C, and the mixture was then moved to room temperature (25 °C) and reacted for 0.5 h. Acetyl chloride (20 mmol, 1.57 g) was dissolved in 5 mL of tetrahydrofuran and added dropwise to the reaction mixture. The mixture was reacted at room temperature (25 °C) for 4 h. The reaction was monitored by LS-MS. After the reaction was complete, the mixture was quenched with water, and 250 mL of ethyl acetate was added. The mixture was extracted three times with 150 mL of saturated brine, dried, and then separated by silica gel column chromatography (development ratio: methanol:ethyl acetate = 1:20) to give compound I-1 (3.64 g, 80.30%). 1 H NMR (400 MHz, DMSO- d6) δ 10.63 (s, 1H), 9.58 (d, J =6.8 Hz, 1H), 8.98 (m, 1H), 8.85 (s, 1H), 8.46 (s, 2H), 8.32 (s, 1H),7.59(d, J = 5.0 Hz, 1H), 6.02 (m, 1H), 2.08 (s, 3H), 1.68 (d, J =6.9 Hz, 3H). The product is a white solid.

[0059] Example 2.

[0060] Preparation of compound I-9:

[0061] Intermediate II-9 was obtained by the synthesis method described in Example 1.

[0062] Intermediate II-9 (10 mmol, 4.65 g) was dissolved in 45 mL of dichloromethane and added to a dry 100 mL single-necked flask. Trifluoroacetic anhydride (13.5 mmol, 2.84 g) and DMAP catalytic amount (0.1 mmol) were added to the reaction system with stirring at room temperature (25 °C). Pyridine (20 mmol, 1.58 g) was added dropwise to the reaction system, and the reaction was carried out at room temperature (25 °C) for 4 h. The reaction was monitored by LS-MS. After the reaction was complete, the solvent was removed under reduced pressure, and 250 mL of ethyl acetate was added. The mixture was extracted three times with 150 mL of saturated brine, twice with 100 mL of dilute hydrochloric acid, and twice with 200 mL of water. After drying, the mixture was separated by silica gel column chromatography (development ratio: methanol:ethyl acetate = 1:20) to obtain compound I-9 (4.79 g, 85.3%). 1 ¹H NMR (400 MHz, DMSO-d⁶) δ 12.41 (s, 1H), 9.63 (d, J = 6.7 Hz, 1H), 9.03 (d, J = 4.9 Hz, 2H), 8.50 (d, J = 1.7 Hz, 2H), 8.35 (s, 1H), 7.63 (t, J = 4.8 Hz, 1H), 6.02 (m, 1H), 1.71 (d, J = 7.0 Hz, 3H). The product is a white solid.

[0063] Example 3.

[0064] Preparation of compound I-14:

[0065] Intermediate II-14 was obtained by the synthesis method of Example 1.

[0066] Intermediate II-14 (10 mmol, 4.45 g) was dissolved in 45 mL of dichloromethane and added to a dry 100 mL single-necked flask. Difluoroacetic anhydride (13.5 mmol, 2.35 g) and DMAP catalytic amount (0.1 mmol) were added to the reaction system with stirring at room temperature (25 °C). Pyridine (20 mmol, 1.58 g) was added dropwise to the reaction system, and the reaction was carried out at room temperature (25 °C) for 4 h. The reaction was monitored by LS-MS. After the reaction was complete, the solvent was removed under reduced pressure, 250 mL of ethyl acetate was added, and the mixture was extracted three times with 150 mL of saturated brine, twice with 100 mL of dilute hydrochloric acid, and twice with 200 mL of water. After drying, the mixture was separated by silica gel column chromatography (development ratio: methanol:ethyl acetate = 1:20) to obtain compound I-14 (4.14 g, 79.2%). 1 ¹H NMR (400 MHz, DMSO-d⁶) δ 12.38 (s, 1H), 9.59 (d, J = 6.7 Hz, 1H), 9.00 (d, J = 4.9 Hz, 2H), 8.42 (d, J = 1.7 Hz, 2H), 8.30 (s, 1H), 7.62 (t, J = 4.8 Hz, 1H), 7.35 (t, J = 57.3 Hz, 1H), 6.03 (m, 1H), 1.71 (d, J = 7.0 Hz, 3H). The product is a white solid.

[0067] Example 4.

[0068] Preparation of formulations.

[0069] 1. Soluble liquid: The product is obtained by dissolving 10-50% of the compound of formula (Ⅰ) and 5-20% of the wetting agent in water and / or water-soluble solvent to a concentration of 100%.

[0070] 2. Emulsifiable concentrate: The product is obtained by dissolving 15-70% of the compound of formula (Ⅰ) and 5-10% of the emulsifier in a water-insoluble organic solvent to a concentration of 100%.

[0071] 3. Water-in-water emulsion: Dissolve 5-40% of the compound of formula (I) and 1-10% of the emulsifier in 20-40% of a water-insoluble organic solvent. Use an emulsifier to introduce the mixture into 100% water and prepare a homogeneous emulsion to obtain the product.

[0072] 4. Suspension: In a stirred ball mill, 20-60% of the compound of formula (Ⅰ) is pulverized with the addition of 2-10% dispersant, 1-5% wetting agent, 0.1-2% thickener, and water to a concentration of 100% to prepare an active substance suspension to obtain the product.

[0073] 5. Water-dispersible granules: The product is obtained by grinding 50-80% of the compound of formula (Ⅰ) with the addition of 100% dispersant and wetting agent and then using industrial production equipment to make it into water-dispersible granules.

[0074] All figures are weight percentages.

[0075] Example 5.

[0076] Bioactivity evaluation: Brown planthopper (Nilaparvata lugens).

[0077] The test compound was dissolved in N,N-dimethylformamide and then diluted to the required concentration with water containing 0.1% Tween-80. Indoor bioassays were performed using a spray method. Uniformly sized rice seedlings were cultured, and the test compound solution was sprayed evenly onto the seedlings. Healthy, uniform brown planthoppers were selected to infect the rice plants. Each concentration treatment was replicated four times, with a blank control containing the same amount of solvent without the pesticide. Two days after application, the number of dead brown planthoppers was assessed, and the mortality rate was calculated (rounded to the nearest integer).

[0078] Mortality grading 48 hours after specific drug treatment: Below 50% is E 50%-70% is D 70%-80% are C 80%-90% are B 90%-100% is A

[0079] In Table 2, CK1 is selected from page 6 of CN113597424. .

[0080] In Table 2, CK2 is selected from CN114728928, I-010.

[0081] In Table 3, CK3 is selected from CN113597424, specifically from 58.003.

[0082] The activity of the above compounds was determined at a concentration of 25 ppm, and the results are shown in Table 2: compound 48-hour mortality rate (%) I-1 A I-2 A I-3 A I-4 A I-5 A I-6 A I-7 A I-8 A I-9 A I-10 A I-11 A I-12 A I-13 A I-14 A I-15 A I-16 A I-17 A I-18 A Fipronil C Trifluoropyrimidine A CK1 C CK2 B CK3 B

[0083] Example 6

[0084] Bioactivity evaluation: Peach aphid (Myzus persicae); the test compound was dissolved in N,N-dimethylformamide and then diluted to the required concentration with water containing 0.1% Tween-80. Indoor bioassays were performed using a spray method. Uniformly sized Chinese cabbages were selected, and the test compound solution was sprayed evenly onto the cabbage leaves. Healthy, uniform aphids were selected to infect the Chinese cabbages. Each concentration treatment was replicated four times, with a treatment containing the same amount of solvent without the pesticide serving as a blank control. The number of dead peach aphids was counted 72 hours after application, and the mortality rate was calculated (rounded to the nearest integer).

[0085] Mortality grading 72 hours after specific drug treatment: Below 50% is E 50%-70% is D 70%-80% are C 80%-90% are B 90%-100% is A

[0086] In Table 3, CK1 is selected from page 6 of CN113597424. In Table 3, CK2 is selected from I-010 of CN114728928. In Table 3, CK3 is selected from 58.003 of CN113597424.

[0087] The activity of the above compounds was determined at a concentration of 25 ppm, and the results are shown in Table 3: compound 72-hour mortality rate (%) I-1 A I-2 A I-3 A I-4 A I-5 A I-6 A I-7 A I-8 A I-9 A I-10 A I-11 A I-12 A I-13 A I-14 A I-15 A I-16 A I-17 A I-18 A Fipronil B Trifluoropyrimidine A CK1 C CK2 C CK3 B

[0088] 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 diamide compound or a salt thereof acceptable as a pesticide, having the structural formula shown in formula (I):

2. In formula (I), Q is selected from substituted or unsubstituted five- or six-membered aryl or heteroaryl groups, such as phenyl, pyridyl, thiophene, thiazole, pyrazole, pyrrole, and furan. R1 is selected from five- or six-membered aryl or heteroaryl groups substituted with substituents, such as phenyl, pyridyl, thiazolyl, pyrazolyl, pyrroleyl, and pyrimidinyl. R2 is selected from C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, substituted or unsubstituted penta- or hexa-aryl or heteroaryl.

3. A diamide compound as described in claim 1, or a salt thereof acceptable as a pesticide, characterized in that, In formula (I), R2 is selected from C1-C4 alkyl, halo-C1-C4 alkyl, C3-C6 cycloalkyl, substituted or unsubstituted phenyl, pyridyl; Preferably, R2 is selected from Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, CF3, CHF2, CH2F, CCl3, CHCl2, CH2Cl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and phenyl. More preferably, R2 is selected from Me, Et, CF3, CHF2, cyclopropane, n-Pr, i-Pr, t-Bu, and cyclopentane.

4. A diamide compound as described in claim 1, or a salt thereof acceptable as a pesticide, characterized in that, In formula (I), R1 is selected from five- or six-membered aryl or heteroaryl groups substituted with substituents; Preferably, the five- or six-membered aryl or heteroaryl group is pyridinyl, thiophene, or pyrimidinyl. Preferably, the substituent is selected from H.

5. A diamide compound as described in claim 1, or a salt thereof acceptable as a pesticide, characterized in that, In formula (I), Q is selected from five- or six-membered aryl or heteroaryl groups that are substituted with 1-3 substituents or are not substituted with substituents; Preferably, the five- or six-membered aryl or heteroaryl group is phenyl, pyridyl, pyrazolyl, or thiazolyl. Preferably, the substituent is selected from F, Cl, Br, I, CN, Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu, OCF3, SCF3, CF3, and OCF. 2、 CHF2, CH2F, CCl3, CHCl2, CH2Cl, or cyclopropane.

6. An insecticidal composition, characterized in that, The pesticide includes at least one of the diamide compounds of any one of claims 1-4 or their salts that are acceptable as pesticides; preferably, it also includes a formulation carrier or formulation adjuvant.

7. A method for controlling plant pests, characterized in that, This includes using an insecticidal effective amount of at least one of the diamide compounds of any one of claims 1-5 or their pesticide-acceptable salts, or the insecticidal composition of claim 5, on crops or pests and / or their habitats.

8. Use of at least one of the diamide compounds as described in any one of claims 1-4 or their pesticide-acceptable salts, or the insecticidal composition as described in claim 5, in the control of plant pests in agriculture and other fields.

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