Bisamide compound and use thereof

Abstract

The present invention belongs to the technical field of pesticides and particularly relates to a bisamide compound and a use thereof. The compound is as represented by general formula (I), wherein X is an aryl group or a heterocyclic group, and Y is a halogen or an alkoxy group. The compound has an excellent control effect on pests, especially agricultural and horticultural pests, but is safe for bees.

Description

A bisamide compound and its application Technical Field

[0001] The present invention belongs to the technical field of pesticides, and in particular relates to a diamide compound and application thereof. Background Art

[0002] In crop production in the agricultural and horticultural fields, damage caused by pests is still serious, and due to the emergence of pests resistant to existing pesticides, etc., the development of novel agricultural and horticultural pesticides is desired. Summary of the Invention

[0003] In order to solve the above problems existing in the prior art, the present invention provides a bisamide compound, which has excellent control effects on harmful organisms, especially agricultural and horticultural pests, and is safe for bees.

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

[0005] A bisamide compound, as shown in Formula I:

[0006] wherein X is an aryl or heterocyclic group, each of which is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl substituted by alkyl or halogen, phenyl, phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-alkylene-(CO)OR is substituted by at least one group, or two adjacent carbon atoms on the ring form a fused ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen or alkyl;

[0007] Y is halogen or alkoxy;

[0008] R is independently hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

[0009] n is 0, 1, or 2.

[0010] In one embodiment, X is aryl or heterocyclic, each of which is independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl or halogen, phenyl, phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-(C1-C8)alkylene-(CO)OR is substituted by at least one group, or two adjacent carbon atoms on the ring form a condensed ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted with halogen or C1-C8 alkyl;

[0011] Y is halogen or C1-C8 alkoxy;

[0012] R is independently hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

[0013] In another embodiment, X is aryl or heterocyclic, each of which is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl or halogen, phenyl, phenyl substituted with 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-(C1-C6)alkylene-(CO)OR substituted by 1 to 3 groups, or two adjacent carbon atoms on the ring form a condensed ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted by halogen or C1-C6 alkyl;

[0014] Y is halogen or C1-C6 alkoxy;

[0015] R is independently hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, or phenyl substituted by 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

[0016] In the definitions of the compounds represented by the above general formula and in all the following structural formulas, the technical terms used, whether used alone or in compound terms, represent the following substituents: Alkyl groups having more than two carbon atoms may be straight-chain or branched. For example, in the compound term "-O-alkylene-(CO)OR," the alkylene group may be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups include, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl, such as n-propyl or isopropyl; C4 alkyl-butyl, such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl, such as n-pentyl; and C6 alkyl-hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but-3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds can be at any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system with, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl with, for example, three to six carbocyclic ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein double bonds can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0017] Unless otherwise specified, the "aryl" mentioned in the present invention includes but is not limited to phenyl, naphthyl, The "heterocyclic group" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups etc., and also include but are not limited to heteroaryl, i.e. an aromatic cyclic group containing, for example, 3 to 6 ring atoms and optionally fused to a benzo ring, wherein 1 to 4 (e.g. 1, 2, 3 or 4) heteroatoms in the ring atoms are selected from oxygen, nitrogen and sulfur, for example

[0018] If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different groups selected from the groups mentioned. Furthermore, identical or different substituent characters contained in identical or different substituents are independently selected and may be identical or different. The same applies to ring systems formed from different atoms and units. At the same time, compounds known to those skilled in the art to be chemically unstable under standard conditions are excluded from the scope of the claims.

[0019] In addition, unless otherwise specified, the term "substituted by at least one group" as used herein refers to being substituted by 1, 2, 3, 4 or 5 groups; groups (including heterocyclic groups, aryl groups, etc.) without a specific connection position can be connected at any position, including the position connected to C or N; if it is substituted, the substituent can also be substituted at any position as long as it complies with the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group Can represent wait.

[0020] The bisamide compounds represented by Formula I of the present invention may contain one or more asymmetric centers in the structural formula, and in some cases, may have two or more optical isomers and diastereomers. The present invention includes any of such optical isomers and mixtures containing them in any proportion. In addition, the bisamide compounds represented by Formula I of the present invention may have two types of geometric isomers derived from carbon-carbon double bonds in the structural formula. The present invention includes all geometric isomers and mixtures containing them in any proportion.

[0021] The present invention also provides a method for preparing the bisamide compound, comprising the following steps:

[0022] (1) reacting the compound represented by Formula II with the compound represented by Formula III or the compound represented by Formula V with the compound represented by Formula VI to obtain the compound represented by Formula IV;

[0023] (2) the compound represented by formula IV is oxidized to obtain the compound represented by formula I;

[0024] Wherein, Hal represents halogen, preferably Cl, and the substituents X and Y are as defined above.

[0025] In one embodiment, the reaction (1) is carried out in the presence of a base and a solvent.

[0026] In another specific embodiment, the base is selected from at least one of an inorganic base (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, K3PO4, NaOH, KOH, NaH, KH, etc.) or an organic base (such as MeONa, t-BuONa, EtONa, AcOK, AcONa, DMAP, pyridine, pyrazole, triethylamine, DIEA, etc.).

[0027] In another embodiment, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane (DCM) or ethyl acetate.

[0028] In one embodiment, the reaction (2) is carried out in the presence of an oxidizing agent and a solvent.

[0029] In another specific embodiment, the oxidant is selected from at least one of meta-chloroperbenzoic acid, H2O2, H2O2 / sodium tungstate, NaClO or KMnO4.

[0030] In another embodiment, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane (DCM) or ethyl acetate.

[0031] The preparation method of the compound of the present invention can also be obtained by referring to CN200810149162.6, CN200680022240.5, CN200680022139.X, etc.

[0032] The present invention also provides an insecticide composition, which comprises a biologically effective amount of at least one of the diamide compounds; preferably, it also comprises a formulation adjuvant; more preferably, it also comprises other active ingredients.

[0033] The present invention also provides a method for controlling pests, which comprises contacting the pests or their environment with a biologically effective amount of the bisamide compound or the composition.

[0034] The present invention also provides use of the bisamide compound or the composition in preventing and controlling pests.

[0035] The term "biologically effective amount" refers to an amount of a biologically active compound (e.g., a compound of Formula I) sufficient to produce the desired biological effect when applied to (i.e., contacted with) the pest to be controlled or its environment, or the plant, the seed from which the plant grows, or the locus of the plant (e.g., the growth medium), thereby protecting the plant from damage by the pest or achieving other desired effects (e.g., increasing plant vigor). The compounds of the present invention can also be applied prophylactically to locations where pests or parasites are expected to appear.

[0036] Pest control agents containing the compound of the present invention as an active ingredient can effectively control the following pests at low concentrations: various agricultural pests that harm agricultural and horticultural crops and trees, sanitary pests that have adverse effects on people's living environment such as houses, stored-grain pests that harm grains stored in warehouses, wood-feeding pests that harm wood in buildings, etc., as well as any harmful organisms such as mites, crustaceans, mollusks, and nematodes that occur and harm in similar circumstances.

[0037] Insects, mites, crustaceans, mollusks and nematodes that can be controlled using the compounds of the present invention include, but are not limited to, Adoxophyes honmai, Adoxophyes orana faciata, Archips breviplicanus, Grapholita inopinata, Archips fuscocupreanus, Grapholita molesta, Choristoneura magnanima, Leguminivora glycinivorella, Olethreutes mori, Caloptilia zachrysa, Argyresthia conjugella, Spulerrina astaurota, Matsumuraes spp. phaseoli), Pandemis heparana (apple leaf roller), Bucculatrix pyrivorella (pear ridge moth), Lyonetia clerkella (peach moth), Carposina niponensis (peach fruit borer), Lyonetia prunifoliella malinella (silver moth), Caloptilia theivora (tea leaf moth), Phyllonorycter ringoniella (golden leaf moth), Phyllocnistis citrella (citrus leaf moth), Acrolepiopsis sapporensis (onion leaf moth), Acrolepiopsis suzukiella (potato leaf moth), Plutella xylostella (diamond back moth), Stathmopoda masinissa (persimmon leaf moth), Helcystogramma triannulella (sweet potato leaf moth), Pectinophora gossypiella (red bell leaf moth), Carposina sasakii (peach fruit borer), Chilo suppressalis (Chilo suppressalis) suppressalis), rice leaf roller (Cnaphalocrocis medinalis), tobacco stem borer (Ephestia elutella), peach borer (Conogethes punctiferalis), melon silk borer (Diaphaniaindica), Bean Pod Borer (Etiella zinckenella), Mulberry Silk Borer (Glyphodes pyloalis), Scirpophaga incertulas, Cabbage Borer (Hellula undalis), Asian Corn Borer (Ostrinia furnacalis), Bean Stalk Borer (Ostrinia scapulalis), Grass Borer (Parapediasia teterrella), Rice Skipper (Parnara guttata), Cabbage White Butterfly (Pieris brassicae), Cabbage White Butterfly (Pieris rapae crucivora), Citrus Swallowtail (Papilio xuthus), Bridge-Building Bug (Ascotis selenaria), Soybean Armyworm (Pseudoplusia includens), Tea Tussock Moth (Euproctis pseudoconspersa), Gypsy Moth (Lymantria dispar), Ancient Tussock Moth (Orgyia thyellina), Fall Moth (Hyphantria cunea), Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Cydla pomonella, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Ostrinia nubilalis, Mamestra brassicae, Mythimna separata, Sesamia inferens, Naranga aenescens, Spodoptera eridania), beet armyworm (Spodoptera exigua), fall armyworm (Spodoptera frugiperda), sea armyworm (Spodoptera littoralis), cutworm (Spodoptera litura), pale sword-shaped armyworm (Spodopteradepravata), Cabbage looper (Trichoplusia ni), grape berry moth (Endopiza viteana), tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta), and other Lepidoptera insects;

[0038] Grape leafhopper (Arboridia apicalis), black-breasted leafhopper (Balclutha saltuella), two-spotted leafhopper (Epiacanthus stramineus), broad bean leafhopper (Empoasca fabae), Empoasca nipponica, large green leafhopper (Empoasca onukii), itai green leafhopper (Empoasca sakaii), Macrosteles striifrons, black-tailed leafhopper (Nephotettix cinctinceps), Psuedatomoscelis seriatus, gray leafhopper (Laodelphax striatella), brown leafhopper (Nilaparvata lugens), whiteback leafhopper (Sogatella furcifera), citrus psylla (Diaphorina citri), pear psylla (Psylla pyrisuga), citrus whitefly (Aleurocanthus spiniferus), silverleaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum), grape whitefly (Aleurolobus taonabae), grape phylloxera (Viteus vitifolii), radish aphid (Lipaphis erysimi), cotton aphid (Aphis gossypii), spiraea aphid (Aphis spiraecola), peach aphid (Myzus persicae), citrus aphid (Toxoptera aurantii), grass scale insect (Drosicha corpulenta), blowing scale insect (Icerya purchasi), Lycoris radish mealybug (Phenacoccus solani), citrus mealybug (Pulvinaria aurantii), citrus hip mealybug (Planococcus citri), citrus round scale insect (Pseudaonidia duplex), vine hip mealybug (Planococcus kuraunhiae), Pseudococcus comstocki, Comstockaspis perniciosa, Ceroplastes ceriferus, Ceroplastes rubens, Aonidiellaaurantii), Tea Garden Shield Scale (Fiorinia theae), Peony Net Shield Scale (Pseudaonidia paeoniae), Mulberry White Shield Scale (Pseudaulacaspis pentagona), Plum White Scale (Pseudaulacaspis prunicola), Euonym Slough Shield Scale (Unaspis euonymi), Arrowhead Scale (Unaspis yanonensis), Temperate Bed Bug (Cimex lectularius), Spotted Whisker Bug (Dolycoris baccarum), Wrinkled Cabbage Bug (Eurydema rugosum), Northern Two-starred Bug (Eysarcoris aeneus), Japanese Two-starred Bug (Eysarcoris lewisi), Black-bellied Bug (Eysarcoris ventralis), Green Bug (Glaucias subpunctatus), Tea Winged Bug (Halyomorpha halys), Black-whiskered Green Rice Bug (Nezara antennata), Nezara viridula, Piezodorus hybneri, Plautia crossota, Scotinophora lurida, Cletus punctiger, Leptocorisa chinensis, Riptortus clavatus, Rhopalus msculatus, Cavelerius saccharivorus, Togo hemipterus, Dysdercus cingulatus, Stephanitis pyrioides, Halticus insularis, Lygus lineolaris, Stenodema sibiricum, Stenotus sibiricum rubrovittatus), rice leaf pest (Trigonotylus caelestialium), and other Hemiptera insects;

[0039] Anomala cuprea, Anomala rufocuprea, Gametis jucunda, Heptophylla picea, Popillia japonica, Lepinotarsa ​​decemlineata, Epilachna varivestis, Melanotus fortnumi, Melanotus tamsuyensis, Lasioderma serricorne, Lyctus brunneus, Tomicus piniperda, Rhizopertha dominica, Epurea domina, Epilachna varivestis, Epilachna vigntioctopunctata, Tenebrio molitor molitor), Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus, Callosobruchus chinensis, Aulacophora femoralis, Oulema oryzae, Chaetocnema concinna, Diabrotica undecimpunctata, Diabrotica virgifera, Diabrotica barberi, Phyllotreta striolata, Psylliodes angusticollis, Rhynchites heros, Cylas formicarius, Anthonomus spp. grandis), rice weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus), clover leaf weevil (Hypera postica), rice water weevil (LissohoptrusColeoptera insects such as the black-eared grape weevil (Otiorhynchus sulcatus), the grain weevil (Sitophilus granarius), the corn weevil (Sitophilus zeamais), the Sphenophorus venatus vestitus, and the green-winged paederus (Paederus fuscipes);

[0040] Insects of the order Brachyoptera, including Frankliniella intonsa, Thrips flavus, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, and Ponticulothrips diospyrosi;

[0041] Asphondylia yushimai, Sitodiplosis mosellana (wheat midge), Bactrocera cucurbitae (melon fruit fly), Bactrocera dorsalis (citrus fruit fly), Ceratitis capitata (Mediterranean fruit fly), Hydrellia griseola (barley water fly), Drosophila suzukii (cherry fruit fly), Agromyza oryzae (rice stalk fly), Chromatomyia horticola (pea fly), Liriomyza bryoniae (tomato fly), Liriomyza chinensis (onion fly), Liriomyza sativae (vegetable fly), Liriomyza trifolii (African daisy fly), Delia platura (gray ground fly), Delia antique (onion fly), Pegomya cunicularia (Cunicularia cunicularia), Rhagoletis pomonella (apple fruit fly), Mayetiola destructor (wheat gall midge), Musca domestica (housefly), domestica), stable flies (Stomoxys calcitrans), sheep lice flies (Melophagus ovinus), cow hide flies (Hypoderma bovis), skin flies (Hypoderma lineatum), sheep mad flies (Oestrus ovis), thorny tongue flies (Glossina palpalis, Glossina morsitans), Prosimulium yezoensis, horseflies (Tabanus trigonus), white-spotted moth flies (Telmatoscopus albipunctatus), Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Asian tiger mosquitoes (Aedes albopicutus), Anopheles hyracanus sinesis, and other Diptera insects;

[0042] Hymenoptera, including Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp., and Monomorium pharaonis;

[0043] Orthoptera insects such as the yellow-faced oil gourd (Teleogryllus emma), oriental mole cricket (Gryllotalpa orientalis), migratory locust (Locusta migratoria), small-winged rice locust (Oxya yezoensis), and desert locust (Schistocerca gregaria);

[0044] Insects of the order Myxothrips, such as Onychiurus folsomi, Onychiurus sibiricus, and Bourletiella hortensis;

[0045] Dictyoptera, including Periplaneta fuliginosa, Periplaneta japonica, Blattella germanica, and Periplaneta Americana;

[0046] Isoptera such as Formosan termites (Coptotermes formosanus), Reticulitermes speratus, and Odontotermes formosanus;

[0047] Cat flea (Ctenocephalidae felis), dog flea (Ctenocephalides canis), chicken flea (Echidnophaga gallinacea), human flea (Pulex irritans), rat flea (Xenopsylla cheopis), and other insects of the order Isoptera;

[0048] Trichophaga insects such as Menacanthus stramineus and Bovicola bovis;

[0049] Insects of the order Pseudotoptera, such as the cattle louse (Haematopinus eurysternus), the pig blood louse (Haematopinus suis), the cattle jaw louse (Linognathus vituli), and the buffalo blind louse (Solenopotes capillatus);

[0050] Mites such as the primrose phytophagous mite (Phytonemus pallidus), the polyphagous tarsonemus latus, and the double-leafed tarsonemus (Tarsonemus bilobatus);

[0051] Penthaleus erythrocephalus, Penthaleus major and other walking mites;

[0052] Spider mites such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai, and Tetranychus urticae;

[0053] Gall mites such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis, and Phyllocoptruta oleivora;

[0054] Flour mites such as the Robin root mite (Rhizoglyphus robini), the corrosive tyrophagus mite (Tyrophagus putrescentiae), and the similis tyrophagus mite;

[0055] Varroa jacobsoni and other Varroa mites;

[0056] Ticks such as Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemophysalis flava, Haemophysalis campanulata, Ixodes ovatus, Ixodes persulcatus, Amblyomma spp., and Dermacentor spp.;

[0057] Carnivorous mites such as Cheyletiella yasguri and Cheyletiella blakei;

[0058] Demodex canis, Demodex cati, and other Demodex mites;

[0059] Sheep itch mite (Psoroptes ovis) and other itch mites;

[0060] Sarcoptes scabiei, Notoedres cati, Knemidocoptes spp. and other scabies mites;

[0061] Crustaceans such as the flat beetle (Armadillidium vulgare);

[0062] Gastropods such as the golden apple snail (Pomacea canaliculata), brown clouded agate snail (Achatina fulica), two-lined slug (Meghimatium bilineatum), Limax Valentiana, land snail (Acusta despecta sieboldiana), and Japanese land snail (Euhadra peliomphala);

[0063] Nematodes include Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, and Bursaphelenchus xylophilus.

[0064] The pest control agent containing the compound of the present invention as an active ingredient has a significant control effect on the above-mentioned harmful crops that attack paddy field crops, dry field crops, fruit trees, vegetables, other crops and flowers. Therefore, according to the predicted period of pest occurrence, before the occurrence of pests or at the moment when the occurrence of pests is confirmed, the paddy field water, stems, leaves or soil of paddy fields, dry fields, fruit trees, vegetables, other crops, flowers, etc. are treated, thereby achieving the effect of the pest control agent of the present invention.

[0065] Pest control agents containing the compounds of the present invention as active ingredients have significant control effects on stored-grain pests and the like that occur during the storage of harvested produce. Specifically, post-harvest treatments such as spraying, painting, coating, impregnating, dusting, fumigating, or pressurized injection of the pest control agents containing the compounds of the present invention as active ingredients onto harvested produce or areas where harvested produce are stored can be performed.

[0066] Furthermore, applying a pest control agent containing the compound of the present invention as an active ingredient to plant seeds can prevent pests that arise in the sown plants. Specifically, the pest control agent containing the compound of the present invention as an active ingredient can be applied directly, diluted with water or the like, or suspended in a form effective for pest control, to the plant seeds by spraying, smearing, dipping, or dusting, thereby contacting the plant seeds with the compound of the present invention.

[0067] Plant seeds are substances used for agricultural reproduction and contain nutrients necessary for plant seedling germination. Examples include seeds of corn, soybeans, adzuki beans, cotton, rice, sugar beets, wheat, barley, sunflowers, tomatoes, cucumbers, eggplants, spinach, beans, pumpkins, sugarcane, tobacco, pimento, and canola; seeds of taro, potato, sweet potato, and konjac; bulbs of edible lilies and tulips; and bulbs of leek.

[0068] The pest control agent containing the compound of the present invention as an active ingredient has a significant control effect on sanitary pests such as dipteran pests (Culex pipiens, ground house mosquitoes, chironomids, houseflies, butterfly flies, horseflies, etc.) and ptera pests (German cockroaches, black cockroaches, American cockroaches, etc.).

[0069] The pest control agent containing the compound of the present invention as an active ingredient has a significant control effect on wood-feeding pests such as termites, brown powder borers, grain borers, leeches, and longhorn beetles (Cerambycidae). By treating the soil or wood in buildings, the above-mentioned wood-feeding pests can be controlled.

[0070] The compounds of the present invention exhibit control effects against various pests and are effective in protecting useful crops. They also demonstrate excellent control effects as insecticides or acaricides at low dosages, significantly contributing to reducing environmental impacts. Furthermore, the compounds of the present invention can exhibit excellent control effects when used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biopesticides, and the like.

[0071] When using the compound of the present invention, it can usually be mixed with an appropriate solid carrier or liquid carrier, and further, as needed, a surfactant, a penetrant, a spreader, a thickener, an antifreeze, a binder, an anti-caking agent, a disintegrant, a defoaming agent, a preservative, and an anti-decomposition agent can be added to prepare any of the following dosage forms for practical use: a solution (soluble concentrate), an emulsion (emulsifiable concentrate), a wettable powder (wettable powder), a water-soluble powder, a water-dispersible granule (water dispersible granule), a water-soluble granule (water soluble granule), a suspension (suspension concentrate), a concentrated emulsion (concentrated emulsion), a suspoemulsion (suspoemulsion), a microemulsion (microemulsion), a dustable powder, a granule (granule), a tablet (tablet), and an emulsifiable gel (emulsifiable gel). Furthermore, from the viewpoint of labor saving and safety improvement, the preparations in any of the above dosage forms may be sealed in water-soluble packaging such as water-soluble capsules and bags made of water-soluble films and supplied.

[0072] The inert carrier that can be used in the present invention may be either solid or liquid. Examples of materials that can form a solid inert carrier include soybean flour, grain flour, wood flour, bark powder, sawdust, tobacco stem powder, walnut shell powder, bran, cellulose powder, residues after plant extract extraction, synthetic polymers such as pulverized synthetic resins, clays (such as kaolin, bentonite, acid clay, etc.), talcs (such as talc, pyrophyllite, etc.), silicas (such as diatomaceous earth, silica sand, mica, white carbon [also known as hydrous micropowder silicon, synthetic highly dispersed silicic acid containing hydrous silicic acid, and products containing calcium silicate as the main component depending on the product]), activated carbon, sulfur powder, pumice, sintered diatomaceous earth, brick crushed material, fly ash, sand, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride, and compost. The above carriers can be used alone or in the form of a mixture of two or more.

[0073] As materials that can serve as liquid inert carriers, in addition to materials having solvent properties themselves, materials that do not have solvent properties but disperse the active ingredient compound with the help of an auxiliary agent can also be selected. For example, the following carriers can be cited as representative examples. The following carriers can be used alone or in the form of a mixture of two or more, such as water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (for example, diethyl ether, dioxane, etc.), and the like. , cellosolve, diisopropyl ether, tetrahydrofuran, etc.), aliphatic hydrocarbons (such as kerosene, mineral oil, etc.), aromatic hydrocarbons (such as benzene, toluene, xylene, solvent naphtha, alkyl naphthalene, etc.), halogenated hydrocarbons (such as dichloromethane, chloroform, carbon tetrachloride, chlorobenzene, etc.), esters (such as ethyl acetate, butyl acetate, ethyl propionate, diisobutyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (such as dimethylformamide, diethylformamide, dimethylacetamide, etc.), nitriles (such as acetonitrile, etc.).

[0074] The above-mentioned solid and liquid carriers may be used alone or in combination of two or more.

[0075] Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkyl (mono- or di-)phenyl ethers, polyoxyethylene (mono-, di- or tri-)styrylphenyl ethers, polyoxyethylene polyoxypropylene block copolymers, polyoxyethylene fatty acid (mono- or di-)esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, castor oil ethylene oxide adducts, ethylene glycol (acetylene glycol),

[0014] In some embodiments, the present invention relates to anionic surfactants such as ethylene glycol, ethylene oxide adducts of acetylene alcohols, ethylene oxide adducts of ethylene glycol, and alkyl glucosides; nonionic surfactants such as alkyl sulfates, alkylbenzenesulfonates, ligninsulfonates, alkylsulfosuccinates, naphthalenesulfonates, alkylnaphthalenesulfonates, salts of formaldehyde condensates of naphthalenesulfonic acid, salts of formaldehyde condensates of alkylnaphthalenesulfonic acid, polyoxyethylene alkyl ether sulfates or phosphates, polyoxyethylene (mono- or di-)alkylphenyl ether sulfates or phosphates, polyoxyethylene (mono-, di-, or tri-)styrylphenyl ether sulfates or phosphates, polycarboxylates (e.g., polyacrylates, polymaleates, and copolymers of maleic acid and olefins) and polystyrenesulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; amphoteric surfactants such as amino acid type and betaine type; polysiloxane surfactants; and fluorine-based surfactants.

[0076] The content of the surfactant is not particularly limited, but is generally preferably in the range of 0.05 to 20 parts by weight relative to 100 parts by weight of the preparation of the present invention.

[0077] To control various pests, the agent can be applied directly, diluted with water, or suspended in an amount effective for pest control, to crops predicted to be infested with the pest or to areas where it is undesirable. The dosage varies depending on various factors, such as the intended purpose, target pest, crop growth status, pest infestation tendency, climate, environmental conditions, formulation, application method, application location, and application period. Generally, it is desirable to use the active ingredient at a concentration of 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm. Furthermore, the application rate per 10 days is generally 1 to 300 g of the active ingredient.

[0078] The amount of the active ingredient of the compound of the present invention is generally 0.1-20% by weight for powders, 5-50% by weight for emulsions, 3-90% by weight for wettable powders, 0.1-20% by weight for granules, 5-90% by weight for suspensions, and 3-90% by weight for water-dispersible granules. Meanwhile, the amount of the carrier in each dosage form is generally 60-99.9% by weight for powders, 40-95% by weight for emulsions, 10-90% by weight for wettable powders, 80-99.9% by weight for granules, 10-95% by weight for suspensions, and 10-90% by weight for water-dispersible granules. The amount of the adjuvant is usually 0.1 to 20% by weight for powders, 1 to 20% by weight for emulsions, 0.1 to 20% by weight for wettable powders, 0.1 to 20% by weight for granules, 0.1 to 20% by weight for suspensions, and 0.1 to 20% by weight for water-dispersible granules.

[0079] Furthermore, when the compounds of the present invention are used as pesticides, they may be mixed with other herbicides, insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. during formulation or spraying, as needed.

[0080] All documents, patent applications, and technical specifications described in this specification are incorporated herein by reference to the same extent as if each individual document, patent application, or technical specification was specifically and individually incorporated by reference. DETAILED DESCRIPTION

[0081] The following examples are provided to illustrate the present invention and should not be considered to limit the present invention in any way. The scope of the rights claimed in the present invention is described in the claims.

[0082] Given the economical efficiency and diversity of the compounds, we have selected and synthesized a number of compounds. A selection of these compounds is listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are intended to better illustrate the present invention but are not intended to limit the present invention. Those skilled in the art should not interpret this as limiting the scope of the present invention to the following compounds.

[0083] Table 1 Compound structures and their 1 H NMR

[0084] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The starting materials can be purchased commercially or can be prepared by methods known in the literature or as described in detail. It will be understood by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention. Although the specific starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions, and these modifications or variations of the preparation methods of the present invention that result in various isomerizations of the compounds are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the present disclosure using conventional chemical methods well known to those skilled in the art. For example, appropriate groups can be protected during the reaction, etc.

[0085] The following process examples are provided to facilitate a further understanding of the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further illustrate the present invention and are not intended to limit its reasonable scope. The reagents used in the synthesis of the compounds shown in the table below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0086] Examples of representative compounds are shown below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0087] 1. Synthesis of Compound 1

[0088] (1) 1-1 (500 mg, 1.15 mmol, 1 eq) was dissolved in acetonitrile (10 ml) and added to a 50 ml single-necked flask. Potassium iodide (47 mg, 0.28 mmol, 0.25 eq) and 1-2 (628 mg, 2.3 mmol, 2 eq) were added and reacted at 85°C for 12 h. After monitoring the reaction completion, the acetonitrile was concentrated and extracted with ethyl acetate. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was mixed and separated by normal phase separation (EA / PE = 2 / 3) to obtain 1-3 (300 mg, yield: 37.5%).

[0089] (2) 1-3 (300 mg, 0.44 mmol, 1 eq) was dissolved in dichloromethane (10 ml) and added to a 50 ml single-necked flask. Meta-chloroperbenzoic acid (151 mg, 0.88 mmol, 2 eq) was added and allowed to react at room temperature for 2 h. After monitoring the reaction completion, water was added for extraction. The organic phase was washed twice with saturated brine, dried over anhydrous sodium sulfate, mixed, and subjected to normal phase separation (EA / PE = 1 / 2) to obtain 80 mg of compound 1, with a yield of 26%.

[0090] 2. Synthesis of Compound 2

[0091] (1) In a 50 ml single-necked flask, 1-1 (1 g, 2.3 mmol) was dissolved in acetonitrile (20 ml), potassium iodide (94 mg, 0.57 mmol, 0.25 eq) and 2-1 (1.1 g, 4.6 mmol, 2 eq) were added, and the mixture was reacted at 80°C for 12 h. After monitoring the reaction completion, the acetonitrile was removed by concentration, and ethyl acetate was added for extraction. The organic phase was washed twice with saturated brine and dried over anhydrous sodium sulfate. The sample was mixed and subjected to normal phase separation (EA / PE = 2 / 3) to obtain 2-2 (912 mg, yield 78.1%) as a white solid.

[0092] (2) In a 100 ml single-necked flask, 2-2 (912 mg, 1.5 mmol) was dissolved in ethanol (50 ml). An aqueous solution of ammonium chloride (0.16 g, 3 mmol) was added, followed by iron powder (0.17 g, 3 mmol). The mixture was reacted at 60°C for 1 h. After monitoring the reaction completion, the mixture was filtered while hot, concentrated, extracted with water, and the organic phase was dried to give crude 2-3 (549 mg, 63.3% yield, as a white solid).

[0093] (3) 2-3 (549 mg, 0.93 mmol) was dissolved in 5 ml of concentrated sulfuric acid. 2 ml of formaldehyde solution was slowly added dropwise under ice-cooling. The temperature was slowly raised to 50°C and the reaction was allowed to proceed for 1 h. The reaction was monitored until the starting material disappeared. Water was added to the reaction solution, extracted three times with ethyl acetate, and washed three times with saturated brine. After drying over anhydrous sodium sulfate, the sample was mixed and passed through a column. The fraction was spin-dried to obtain 2-4 (146 mg, yield 25.9%) as a white solid.

[0094] (4) 2-4 (146 mg, 0.24 mmol) was dissolved in 10 ml of THF, pyridine (37.9 mg, 0.48 mmol) was added, and benzoyl chloride (33.6 mg, 0.24 mmol) was slowly added dropwise in an ice bath. The reaction was allowed to react at room temperature for 1 h, and the reaction was monitored until the starting material disappeared. Water was added to the reaction solution, extracted three times with ethyl acetate, and washed three times with saturated brine. After drying over anhydrous sodium sulfate, the mixture was passed through a column, and the fraction was spin-dried to obtain 2-5 (102 mg, yield 59.6%, white solid).

[0095] (5) 2-5 (102 mg, 0.14 mmol) was dissolved in 10 ml of DCM, and m-chloroperbenzoic acid (48.2 mg, 0.28 mmol) was added. The reaction was allowed to react at room temperature for 5 h, and the reaction was monitored until the starting material disappeared. The reaction solution was added with water, extracted three times with DCM, and washed three times with saturated brine. After drying over anhydrous sodium sulfate, the sample was mixed and passed through a column. The fraction was spin-dried to obtain compound 2 (61 mg, yield 57.5%, white solid).

[0096] 3. Synthesis of Compound 46

[0097] (1) In a 250 mL single-necked bottle, 1-1 (10 g, 1.0 eq, 23.09 mmol) was added to 100 mL of acetonitrile, followed by potassium iodide (766.5 mg, 0.2 eq, 4.62 mmol) and 46-1 (5.0 g, 1.0 eq, 23.09 mmol). The atmosphere was replaced with nitrogen three times, and the temperature was raised to 80°C for overnight reaction. The reaction was monitored until the starting material disappeared. The reaction solution was concentrated, the residue was diluted with water (50 mL), and extracted with ethyl acetate (50 mL x 3). The organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then mixed and passed through a column to obtain the product 46-2 (12.5 g, yield 88%, yellow oil).

[0098] (2) In a 250 mL single-necked flask, 46-2 (12.5 g, 1.0 eq, 20.42 mmol) was added to 90 mL of ethanol and 30 mL of water, and ammonium chloride (3.3 g, 3.0 eq, 61.25 mmol) and iron powder (3.42 g, 3.0 eq, 61.25 mmol) were added. The temperature was raised to 80°C and the reaction was allowed to react for 2 h. The reaction was monitored until the starting material disappeared. The reaction solution was concentrated, and the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3). The organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then mixed and passed through a column to obtain the product 46-3 (6.3 g, 53% yield, brown solid).

[0099] (3) In a 100 mL single-necked flask, 46-3 (6.3 g, 1.0 eq, 10.8 mmol) was added to 50 mL of concentrated sulfuric acid, and paraformaldehyde (1.3 g, 4.0 eq, 43.3 mmol) was added. The temperature was raised to 40°C and the reaction was allowed to proceed for 2 h. The reaction was monitored until the starting material disappeared. After the reaction was completed, the reaction solution was poured into 100 mL of water, the pH was adjusted to neutral, and the solution was extracted with ethyl acetate (50 mL x 3). The organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then passed through a column to obtain the product 46-4 (3.2 g, 49% yield, as a white solid).

[0100] (4) In a 50 mL single-necked bottle, 46-4 (0.1 g, 1.0 eq, 167.7 μmol) was added to 5 mL of dichloromethane, followed by the addition of 46-5 (0.04 g, 1.5 eq, 251.55 μmol) and triethylamine (0.02 g, 1.0 eq, 167.7 μmol). The reaction was allowed to react overnight at room temperature. The reaction was monitored until the starting material disappeared. After the reaction was complete, the reaction solution was poured into 10 mL of water and extracted with ethyl acetate (10 mL x 3). The organic phase was washed with saturated brine (10 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then passed through a column to obtain the product 46-6 (0.1 g, 80% yield, white solid).

[0101] (5) In a 50 mL single-necked bottle, 46-6 (0.1 g, 1.0 eq, 135.80 μmol) was added to 5 mL of dichloromethane, and m-chloroperbenzoic acid (0.06 g, 2.0 eq, 271.59 μmol) was added. The reaction was allowed to react at room temperature for 2 h. The reaction was monitored until the starting material disappeared. After the reaction was complete, the reaction solution was poured into 20 mL of saturated sodium thiosulfate solution and extracted with ethyl acetate (10 mL x 3). The organic phase was washed with saturated sodium bicarbonate solution (10 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then mixed and passed through a column to obtain the product, compound 46 (0.05 g, 48% yield, as a white solid).

[0102] 4. Synthesis of Compound 76

[0103] (1) In a 50 mL single-necked bottle, 46-4 (0.1 g, 1.0 eq, 167.7 μmol) was added to 5 mL of dichloromethane, followed by the addition of 76-1 (0.04 g, 1.5 eq, 251.55 μmol) and triethylamine (0.02 g, 1.0 eq, 167.7 μmol). The mixture was reacted at room temperature overnight. The reaction was monitored until the starting material disappeared. After the reaction was completed, the reaction solution was poured into 10 mL of water and extracted with ethyl acetate (10 mL x 3). The organic phase was washed with saturated brine (10 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then mixed and passed through a column to obtain the product 76-2 (0.1 g, yield 85%, white solid).

[0104] (2) In a 50 mL single-necked bottle, 76-2 (0.1 g, 1.0 eq, 142.57 μmol) was added to 5 mL of acetonitrile, followed by hydrogen peroxide (0.02 g, 3.0 eq, 427.72 μmol) and sodium tungstate (0.004 g, 0.1 eq, 14.26 μmol). The temperature was raised to 50°C for 2 h. The reaction was monitored until the starting material disappeared. After the reaction was complete, the reaction solution was concentrated, the residue was diluted with water (10 mL), and extracted with ethyl acetate (10 mL x 3). The organic phase was washed with sodium chloride solution (10 mL x 3), dried over anhydrous sodium sulfate, concentrated, and then passed through a column to obtain compound 76 (0.07 g, 48% yield, as a white solid).

[0105] Biological activity evaluation:

[0106] (1) Insecticidal activity test:

[0107] Preparation of medicine: After dissolving the original medicine with acetone, dilute the solution with distilled water to a gradient dose.

[0108] Application method:

[0109] Fall Armyworm (leaf dip method): Harvest untreated corn leaves that do not contain insecticide-resistant genes, cut them into 3-4 cm segments, and soak each leaf in the insecticide solution for 20 seconds. Remove and air dry on absorbent paper. Then, place three treated leaves in a plastic box and inoculate ten third-instar insects that have been starved for two hours. Each box contains one replicate, and each treatment is replicated three times. Acetone at the highest dose serves as a control. After application, transfer the insects to captive conditions. After 48 hours, count the number of dead insects and calculate mortality.

[0110] Leek Bradyma (drip method + leaf dip method): Place two layers of filter paper in a petri dish. After moistening the filter paper with water, inoculate 15 third-instar test insects that have been starved for 2 hours into each dish. Then use a pipette to draw 400uL of the drug solution and evenly drip it on the leek Bradyma larvae. Then take a 2cm long leek pseudostem, wash and dry it, soak it in the drug solution for 20 seconds, take it out and dry it on absorbent paper, and place it next to the leek Bradyma larvae in the petri dish. Each petri dish is a replicate, and each treatment is repeated 3 times. The highest dose of acetone is used as a control. After application, transfer the insects to the breeding conditions for breeding. After 48 hours, the results are investigated, and the mortality of each treatment is counted and the mortality rate is calculated.

[0111] Mealworm (leaf dip method): Pick untreated cabbage leaves that do not contain insecticide-resistant genes, cut them into 2 x 2 cm squares, and soak each in the insecticide solution for 20 seconds. Remove and air dry on absorbent paper. Then, place two treated leaves in a plastic box and inoculate 10 mealworms that have been starved for 2 hours. Each box contains one replicate, and each treatment is replicated three times. The highest dose of acetone was used as a control. After treatment, transfer the insects to captive conditions. After 48 hours, count the number of dead insects and calculate the mortality rate.

[0112] Green peach aphid (immersion method): Cut the leaves with insects and soak them in the drug solution for 5 seconds. After taking them out, dry them on absorbent paper, and then put them in a small plastic box with an outer diameter of 9 cm. After 48 hours, investigate the number of dead insects and calculate the mortality rate.

[0113] Armyworms and Spodoptera litura (spray method): Select test insects that have been reared indoors and have the same physiological state. Place them in disposable sauce cups. Inoculate 10 test insects of the same growth type in each cup. Place them on leaves or stems of host plants. Then use a spray tower to spray. Close the lid tightly after spraying. Repeat three times. Use the highest dose of acetone as a control. After spraying, transfer the insects to the rearing conditions. Mortality rate = (number of dead insects / number of test insects) × 100%

[0114] Table 2 Insecticidal activity test results of representative compounds

[0115] Note: N stands for no data; Reference compound A: Control compound B: Control compound C:

[0116] (2) Bee acute toxicity test:

[0117] An acute toxicity test on honeybees was conducted according to the method described in GB / T 31270.10-2014, and the poisoning symptoms and the number of deaths were observed and recorded 96 hours after treatment. The test results showed that the acute oral toxicity and acute contact toxicity of compound 1 of the present invention to honeybees had a half-lethal dose (LD50) greater than 2 μg ai / bee, while the acute oral toxicity LD50 of the control compound B (brofenac) was 0.0008 μg ai / bee, and the acute contact toxicity LD50 was 0.005 μg ai / bee. It can be seen that the compounds described in the present application have significantly reduced toxicity to honeybees and better safety.

[0118] At the same time, many tests have found that the compound of the present invention has excellent effects as a pest control agent, especially an agricultural and horticultural insecticide, and has certain commercial value.

Claims

1. A bisamide compound as shown in formula I, in, X is an aryl or heterocyclic group, which is independently unsubstituted or selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl substituted by alkyl or halogen, phenyl, phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-alkylene-(CO)OR is substituted by at least one group, or two adjacent carbon atoms on the ring form a condensed ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted by halogen or alkyl; Y is halogen or alkoxy; R is independently hydrogen, alkyl, haloalkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy; n is 0, 1 or 2.

2. A bisamide compound according to claim 1, characterized in that: X is an aryl or heterocyclic group, which is independently unsubstituted or substituted by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl substituted by C1-C8 alkyl or halogen, phenyl, phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-(C1-C8)alkylene-(CO)OR is substituted by at least one group, or two adjacent carbon atoms on the ring form a condensed ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted by halogen or C1-C8 alkyl; Y is halogen or C1-C8 alkoxy; R is independently hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. A bisamide compound according to claim 1 or 2, characterized in that: X is an aryl or heterocyclic group, which is independently unsubstituted or selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl or halogen, phenyl, phenyl substituted by 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R)2 or -O-(C1-C6)alkylene-(CO)OR substituted by 1 to 3 groups, or two adjacent carbon atoms on the ring form a condensed ring with -OCH2CH2- or -OCH2O- which is unsubstituted or substituted by halogen or C1-C6 alkyl; Y is halogen or C1-C6 alkoxy; R is independently hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl, or phenyl substituted by 1 to 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

4. A method for preparing a bisamide compound as claimed in any one of claims 1 to 3, characterized in that: The following steps are involved: (1) reacting the compound represented by formula II with the compound represented by formula III or reacting the compound represented by formula V with the compound represented by formula VI to obtain the compound represented by formula IV; (2) the compound represented by formula IV is oxidized to obtain the compound represented by formula I; Wherein, Hal represents halogen, preferably Cl, and the substituents X and Y are defined as described in any one of claims 1-3; Preferably, the reaction (1) is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of an inorganic base or an organic base; more preferably, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; Preferably, the reaction (2) is carried out in the presence of an oxidant and a solvent; more preferably, the oxidant is selected from at least one of meta-chloroperbenzoic acid, H2O2, H2O2 / sodium tungstate, NaClO or KMnO4; more preferably, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

5. An insecticidal composition, characterized in that: It comprises a biologically effective amount of at least one of the bisamide compounds described in any one of claims 1 to 3; preferably, it also comprises a formulation adjuvant; more preferably, it also comprises other active ingredients.

6. A method for controlling pests, characterized in that: The method comprises contacting the pest or its environment with a biologically effective amount of the bisamide compound according to any one of claims 1 to 3 or the composition according to claim 5.

7. Use of the bisamide compound according to any one of claims 1 to 3 or the composition according to claim 5 in controlling pests.

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