Bisamide compound and application thereof

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a bisamide compound and application thereof. The compound is shown as a general formula I: # imgabs0 #, in which X is aryl or heterocyclic group, and Y is halogen or alkoxy. The compound has an excellent control effect on pests, especially agricultural and horticultural pests, and is safe to bees.

Description

Technical Field

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

[0002] In crop production in the fields of agriculture and horticulture, damage caused by pests remains serious, and due to the emergence of pests resistant to existing pesticides, etc., there is a desire to develop novel insecticides for agriculture and horticulture. Summary of the Invention

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

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

[0005] A diamide compound, as shown in formula I:

[0006]

[0007] Wherein, X is an aryl group or a heterocyclic group, which are each independently unsubstituted or substituted by at least one group 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, or two adjacent carbon atoms on the ring are combined with unsubstituted or halogen- or alkyl-substituted -OCH 2 CH 2 - or -OCH 2 O- to form a fused ring;

[0008] Y is halogen or alkoxy;

[0009] R are each 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;

[0010] n is 0, 1 or 2.

[0011] In a specific embodiment, X is an aryl or a heterocyclic group, which are each independently unsubstituted or substituted by one or more groups selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo C1-C8 alkyl, halo C2-C8 alkenyl, halo 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, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy, -OR, -SR, -(CO)OR, -S(O) n R, -N(R) 2 or -O-(C1-C8) alkylene-(CO)OR, or two adjacent carbon atoms on the ring are combined with unsubstituted or halogen- or C1-C8 alkyl-substituted -OCH 2 CH 2 - or -OCH 2 O- to form a fused ring;

[0012] Y is halogen or C1-C8 alkoxy;

[0013] R are each independently hydrogen, C1-C8 alkyl, halo C1-C8 alkyl, phenyl, or phenyl substituted by at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy.

[0014] In another specific embodiment, X is an aryl or a heterocyclic group, which are each independently unsubstituted or substituted by 1 to 3 groups 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 by C1-C6 alkyl or halogen, phenyl, phenyl substituted by 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, or two adjacent carbon atoms on the ring are combined with unsubstituted or halogen- or C1-C6 alkyl-substituted -OCH 2 CH2 - or -OCH 2 O - forms a condensed ring;

[0015] Y is halogen or C1 - C6 alkoxy;

[0016] Each R is independently hydrogen, C1 - C6 alkyl, halo - C1 - C6 alkyl, phenyl, or phenyl substituted by 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.

[0017] In the definitions of the compounds represented by the above general formula and all the following structural formulas, the technical terms used, whether used alone or in a compound word, represent the following substituents: An alkyl group having more than two carbon atoms can be straight - chain or branched - chain. For example, in the compound word “-O - alkylene -(CO)OR”, alkylene can be -CH 2 -, -CH 2 CH 2 -, -CH(CH 3 ) -, -C(CH 3 ) 2 -, etc. The alkyl group is, for example, C1 alkyl - methyl; C2 alkyl - ethyl; C3 alkyl - propyl such as n - propyl or isopropyl; C4 alkyl - butyl such as n - butyl, isobutyl, tert - butyl or 2 - butyl; C5 alkyl - pentyl such as n - pentyl; C6 alkyl - hexyl such as n - hexyl, iso - hexyl and 1,3 - dimethylbutyl. Similarly, alkenyl is, for example, vinyl, allyl, 1 - methylprop - 2 - en - 1 - yl, 2 - methylprop - 2 - en - 1 - yl, but - 2 - en - 1 - yl, but - 3 - en - 1 - yl, 1 - methylbut - 3 - en - 1 - yl and 1 - methylbut - 2 - en - 1 - yl. Alkynyl is, for example, ethynyl, propargyl, but - 2 - yn - 1 - yl, but - 3 - yn - 1 - yl, 1 - methylbut - 3 - yn - 1 - yl. The multiple bond can be at any position of each unsaturated group. Cycloalkyl is a saturated carbocyclic ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

[0018] Unless otherwise specified, the “aryl” as used in the present invention includes, but is not limited to, phenyl, naphthyl, The “heterocyclic group” not only includes, but is not limited to, saturated or unsaturated non - aromatic cyclic groups

[0019]

[0020] Also included are, but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally having benzo ring fusion, where 1 to 4 (e.g., 1, 2, 3, or 4) of the ring atoms are heteroatoms selected from oxygen, nitrogen, and sulfur, such as

[0021] If a group is substituted by a group, this is to be understood to mean that the group is substituted by one or more identical or different groups selected from those mentioned. Additionally, the identical or different substitution characters contained in the identical or different substituents are each independently selected and can be the same or different. This also applies to ring systems formed from different atoms and units. At the same time, the scope of the claims will exclude those compounds that are known to those skilled in the art to be chemically unstable under standard conditions.

[0022] In addition, unless otherwise specifically defined, "substituted by at least one group" as used in the present invention means substituted by, for example, 1, 2, 3, 4, or 5 groups; for groups without specific connection positions indicated (including heterocyclic groups, aryl groups, etc.), they can be connected at any position, including positions connected to C or N; if it is substituted, the substituents can also be substituted at any position as long as it conforms to the chemical bond connection rules. For example, a heteroaryl group substituted by 1 methyl group can represent

[0023] The bisamide compounds represented by formula I of the present invention may contain one or a plurality of asymmetric centers in the structural formula, and in some cases, there may be two or more optical isomers and diastereoisomers. The present invention includes any one 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.

[0024] The present invention also provides a method for preparing the bisamide compounds, comprising the following steps:

[0025] (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;

[0026]

[0027] (2) Oxidizing the compound represented by formula IV to obtain the compound represented by formula I;

[0028] Among them, Hal represents a halogen, preferably Cl, and the substituents X and Y are defined as described above.

[0029] In one specific embodiment, the reaction (1) is carried out in the presence of a base and a solvent.

[0030] In another specific embodiment, the base is selected from at least one of inorganic bases (such as K 2 CO 3 , Na 2 CO 3 , Cs 2 CO 3 , NaHCO 3 , KF, CsF, KI, NaI, K 3 PO 4 , NaOH, KOH, NaH, KH, etc.) or organic bases (such as MeONa, t-BuONa, EtONa, AcOK, AcONa, DMAP, pyridine, pyrazole, triethylamine, DIEA, etc.).

[0031] In another specific embodiment, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane (DCM), or ethyl acetate.

[0032] In one specific embodiment, the reaction (2) is carried out in the presence of an oxidant and a solvent.

[0033] In another specific embodiment, the oxidant is selected from at least one of m-chloroperoxybenzoic acid, H 2 O 2 , H 2 O 2 / sodium tungstate, NaClO, or KMnO 4 .

[0034] In another specific embodiment, the solvent is selected from at least one of THF, DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane (DCM), or ethyl acetate.

[0035] The preparation method of the compound of the present invention can also be prepared with reference to CN200810149162.6, CN200680022240.5, CN200680022139.X, etc.

[0036] The present invention also provides an insecticidal composition, which contains at least one of the diamide compounds in a biologically effective amount; preferably, formulation adjuvants are further included; more preferably, other active ingredients are further included.

[0037] 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 diamide compound or the composition as described above.

[0038] The present invention also provides the use of the diamide compound or the composition as described above in controlling pests.

[0039] The term "biologically effective amount" refers to the amount of a biologically active compound (e.g., a compound of formula I) that, when applied to (i.e., contacted with) the pests to be controlled or their environment, or to a plant, the seeds from which the plant grows, or the location of the plant (e.g., the growth medium), is sufficient to produce the desired biological effect, thereby protecting the plant from damage by pests or achieving other desired effects (e.g., enhancing plant vigor). The compounds of the present invention can also be applied prophylactically to locations where pests or parasites are expected to occur.

[0040] The pest control agent containing the compound of the present invention as an active ingredient can effectively control the following pests at a low concentration: various agricultural pests that damage agricultural and horticultural crops and trees, etc., sanitary pests that have an adverse impact on the living environment of people such as houses, stored grain pests that damage grains stored in warehouses, etc., wood-eating pests that damage the wood of buildings, etc., insects, and any pests among mites, crustaceans, mollusks, and nematodes that occur and cause damage under the same circumstances.

[0041] Insects, mites, crustaceans, mollusks, and nematodes that can be controlled using the compounds of the present invention. Specifically, for example, the following substances can be mentioned, but are not limited thereto: 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, Matsumuraeses phaseoli, Pandemis heparana, Bucculatrix pyrivorella, Lyonetia clerkella, Carposina niponensis, Lyonetia prunifoliella malinella, Caloptilia theivora, Phyllonorycter ringoniella, Phyllocnistis citrella, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella, Plutella xylostella, Stathmopoda masinissa, Helcystogramma triannulella, Pectinophora gossypiella, Carposina sasakii, Chilo suppressalis, Cnaphalocrocis medinalis, Ephestia elutella, Conogethes punctiferalis, Diaphaniaindica), Etiella zinckenella, Glyphodes pyloalis, Scirpophaga incertulas, Hellula undalis, Ostrinia furnacalis, Ostrinia scapulalis, Parapediasia teterrella, Parnara guttata, Pieris brassicae, Pieris rapae crucivora, Papilio xuthus, Ascotis selenaria, Pseudoplusia includens, Euproctis pseudoconspersa, Lymantria dispar, Orgyia thyellina, Hyphantria cunea, Lemyra imparilis, Adris tyrannus, Aedia leucomelas, Agrotis ipsilon, Agrotis segetum, Autographa nigrisigna, Ctenoplusia agnata, Cydia pomonella, Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea, Heliothis virescens, Ostrinia nubilalis, Mamestra brassicae, Mythimna separata, Sesamia inferens, Naranga aenescens, Spodoptera eridania, Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, SpodopteraLepidopteran insects such as depravata, Trichoplusia ni, Endopiza viteana, Manduca quinquemaculata, Manduca sexta, etc.;

[0042] Arboridia apicalis, Balclutha saltuella, Epiacanthus stramineus, Empoasca fabae, Empoascanipponica, Empoasca onukii, Empoasca sakaii, Macrosteles striifrons, Nephotettix cinctinceps, Psuedatomoscelisseriatus, Laodelphax striatella, Nilaparvata lugens, Sogatella furcifera, Diaphorina citri, Psylla pyrisuga, Aleurocanthus spiniferus, Bemisia argentifolii, Bemisia tabaci, Dialeurodes citri, Trialeurodes vaporariorum, Aleurolobus taonabae, Viteus vitifolii, Lipaphis erysimi, Aphis gossypii, Aphis spiraecola, Myzus persicae, Toxoptera aurantii, Drosicha corpulenta, Icerya purchasi, Phenacoccus solani, Pulvinaria aurantii, Planococcus citri, Pseudaonidia duplex, Planococcus kuraunhiae, Pseudococcus comstocki, Comstockaspis perniciosa, Ceroplastes ceriferus, Ceroplastes rubens, AonidiellaAonidiella aurantii, Fiorinia theae, Pseudaonidia paeoniae, Pseudaulacaspis pentagona, Pseudaulacaspis prunicola, Unaspis euonymi, Unaspis yanonensis, Cimex lectularius, Dolycoris baccarum, Eurydema rugosum, Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Glaucias subpunctatus, Halyomorpha halys, 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 rubrovittatus, Trigonotylus caelestialium and other Hemiptera insects;

[0043] 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, Epuraea domina, Epilachna varivestis, Epilachna vigntioctopunctata, Tenebrio 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 grandis, Echinocnemus squameus, Euscepes postfasciatus, Hypera postica, LissohoptrusColeoptera insects such as Oryzophilus, Otiorhynchus sulcatus, Sitophilus granarius, Sitophilus zeamais, Sphenophorus venatus vestitus, Paederus fuscipes, etc.;

[0044] Thysanoptera insects such as Frankliniella intonsa, Thrips flavus, Frankliniella occidentalis, Heliothrips haemorrhoidalis, Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Ponticulothrips diospyrosi, etc.;

[0045] Asphondylia yushimai, Sitodiplosis mosellana, Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis capitata, Hydrellia griseola, Drosophila suzukii, Agromyza oryzae, Chromatomyia horticola, Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii, Delia platura, Delia antique, Pegomya cunicularia, Rhagoletis pomonella, Mayetiola destructor, Musca domestica, Stomoxys calcitrans, Melophagus ovinus, Hypoderma bovis, Hypoderma lineatum, Oestrus ovis, Glossina palpalis, Glossina morsitans, Prosimulium yezoensis, Tabanus trigonus, Telmatoscopus albipunctatus, Leptoconops nipponensis, Culex pipiens pallens, Aedes aegypti, Aedes albopicutus, Anopheles hyracanus sinesis and other Diptera insects;

[0046] Hymenoptera insects such as Apethymus kuri, Athalia rosae, Arge pagana, Neodiprion sertifer, Dryocosmus kuriphilus, Eciton burchelli, Eciton schmitti, Camponotus japonicus, Vespa mandarina, Myrmecia spp., Solenopsis spp., Monomorium pharaonis, etc.;

[0047] Orthoptera insects such as Teleogryllus emma, Gryllotalpa orientalis, Locusta migratoria, Oxya yezoensis, Schistocerca gregaria, etc.;

[0048] Collembola insects such as Onychiurus folsomi, Onychiurus sibiricus, Bourletiella hortensis, etc.;

[0049] Dictyoptera insects such as Periplaneta fuliginosa, Periplaneta japonica, Blattella germanica, Periplaneta Americana, etc.;

[0050] Isoptera insects such as Coptotermes formosanus, Reticulitermes speratus, Odontotermes formosanus, etc.;

[0051] Siphonaptera insects such as Ctenocephalidae felis, Ctenocephalides canis, Echidnophaga gallinacea, Pulex irritans, Xenopsylla cheopis, etc.;

[0052] Mallophagans such as Menacanthus stramineus and Bovicola bovis;

[0053] Anoplurans such as Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, and Solenopotes capillatus;

[0054] Eriophyids such as Phytonemus pallidus, Polyphagotarsonemus latus, and Tarsonemus bilobatus;

[0055] Oribatids such as Penthaleus erythrocephalus and Penthaleus major;

[0056] Tetranychids such as Oligonychus shinkajii, Panonychus citri, Panonychus mori, Panonychus ulmi, Tetranychus kanzawai, and Tetranychus urticae;

[0057] Eriophyids such as Acaphylla theavagrans, Aceria tulipae, Aculops lycopersici, Aculops pelekassi, Aculus schlechtendali, Eriophyes chibaensis, and Phyllocoptruta oleivora;

[0058] Acarids such as Rhizoglyphus robini, Tyrophagus putrescentiae, and Tyrophagus similis;

[0059] Varroas such as Varroa jacobsoni;

[0060] Ticks such as *Boophilus microplus*, *Rhipicephalus sanguineus*, *Haemaphysalis longicornis*, *Haemophysalis flava*, *Haemophysalis campanulata*, *Ixodes ovatus*, *Ixodes persulcatus*, *Amblyomma spp.*, *Dermacentor spp.*;

[0061] Carnivorous mites such as *Cheyletiella yasguri*, *Cheyletiella blakei*;

[0062] Demodex mites such as *Demodex canis*, *Demodex cati*;

[0063] Psoroptes mites such as *Psoroptes ovis*;

[0064] Sarcoptes mites such as *Sarcoptes scabiei*, *Notoedres cati*, *Knemidocoptes spp.*;

[0065] Crustaceans such as *Armadillidium vulgare*;

[0066] Gastropods such as *Pomacea canaliculata*, *Achatina fulica*, *Meghimatium bilineatum*, *Limax valentiana*, *Acusta despecta sieboldiana*, *Euhadra peliomphala*;

[0067] Nematodes such as Prathylenchus coffeae, Prathylenchus penetrans, Prathylenchus vulnus, Globodera rostochiensis, Heterodera glycines, Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, Bursaphelenchus xylophilus, etc.

[0068] The pest control agent containing the compound of the present invention as an active ingredient has a remarkable control effect on the above-mentioned harmful crops that invade paddy field crops, upland field crops, fruit trees, vegetables, other crops and flowers, etc. Therefore, according to the predicted pest occurrence period, before the pests occur or at the moment when the pests are confirmed to occur, the paddy water, stems and leaves or soil of paddy fields, upland fields, fruit trees, vegetables, other crops, flowers, etc. are treated, and thus the effect of the pest control agent of the present invention can be obtained.

[0069] The pest control agent containing the compound of the present invention as an active ingredient has a remarkable control effect on stored grain pests, etc. generated during the storage of harvested products. That is, the harvested products or the storage places of the harvested products are subjected to postharvest treatments such as spraying, smearing, coating, impregnating, film coating, fumigating / smoking or pressure injection with the pest control agent containing the compound of the present invention as an active ingredient.

[0070] In addition, when the pest control agent containing the compound of the present invention as an active ingredient is applied to plant seeds, the invasion caused by pests generated in the plants after sowing can be prevented. That is, the pest control agent containing the compound of the present invention as an active ingredient is directly applied, or appropriately diluted with water or the like or in a suspended form, and the plant seeds are treated by spraying, smearing, impregnating or film coating, etc. with an effective amount for pest control, so that the compound of the present invention can be brought into contact with the plant seeds.

[0071] The so-called plant seeds refer to substances that store the nutrients required for the germination of plant seedlings and are used for reproduction in agriculture. For example, seeds such as corn, soybean, adzuki bean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, kidney bean, pumpkin, sugarcane, tobacco leaf, sweet pepper and canola, or seed tubers such as taro, potato, sweet potato, konjac, bulbils such as edible lily, tulip, or bulbils such as scallion, etc. can be cited.

[0072] The pest control agent containing the compound of the present invention as an active ingredient has a remarkable control effect on sanitary pests such as Diptera pests (Culex pipiens pallens, Culex molestus, Chironomus plumosus, Musca domestica, Psychodidae, Tabanidae, etc.), Lepidoptera pests (Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, etc.).

[0073] The pest control agent containing the compound of the present invention as an active ingredient has a remarkable control effect on wood-eating pests such as termites, Lyctus brunneus, Rhizopertha dominica, Anobiidae, Cerambycidae, etc. By treating the wood of soil or buildings, etc., the above-mentioned wood-eating pests can be controlled.

[0074] The compound of the present invention shows a control effect on various pests, shows an effect of protecting useful crops, and shows an excellent control effect as an insecticide or acaricide at a low drug amount. Therefore, it has an effect of making a great contribution to reducing the environmental load. In addition, the compound of the present invention can also show an excellent control effect by being mixed with other agricultural and horticultural insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, biological pesticides, etc.

[0075] When using the compound of the present invention, it can usually be mixed with a suitable solid carrier or liquid carrier, and further, surfactants, penetrants, spreaders, thickeners, antifreezes, binders, anti-caking agents, disintegrants, defoamers, preservatives, decomposition inhibitors, etc. can be added as needed to prepare any of the following dosage forms for practical use. The dosage forms include soluble concentrate, emulsifiable concentrate, wettable powder, water soluble powder, water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion, microemulsion, dustable powder, granule, tablet, emulsifiable gel, etc. In addition, from the viewpoints of labor saving and safety improvement, the preparations of any of the above dosage forms can also be sealed in water-soluble capsules and water-soluble film bags and other water-soluble packages for supply.

[0076] The inert carrier that can be used in the present invention can be either solid or liquid. As materials that can form a solid inert carrier, for example, soybean powder, cereal powder, wood powder, bark powder, sawdust, tobacco stem powder, walnut shell powder, bran, cellulose powder, residue after extraction of plant extracts, synthetic polymers such as pulverized synthetic resin, clays (such as kaolin, bentonite, acid clay, etc.), talcs (such as talc, pyrophyllite, etc.), silica-based materials (such as diatomaceous earth, silica sand, mica, white carbon black [also known as hydrated micropowdered silica, synthetic highly dispersed silicic acid containing water. Depending on the product, there are products with calcium silicate as the main component.]), activated carbon, sulfur powder, pumice, sintered diatomaceous earth, pulverized bricks, fly ash, sand, calcium carbonate, calcium phosphate and other inorganic mineral powders, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, compost, etc. can be cited. The above carriers can be used alone or in the form of a mixture of two or more kinds.

[0077] As materials that can become liquid inert carriers, in addition to materials that themselves have solvent properties, materials that do not have solvent properties but can disperse the active ingredient compound with the help of auxiliaries can also be selected. For example, as representative examples, the carriers listed below can be cited. The following carriers can be used alone or in the form of a mixture of two or more kinds. For example, water, alcohols (such as methanol, ethanol, isopropanol, butanol, ethylene glycol, etc.), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.), ethers (such as diethyl ether, dioxane, 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.).

[0078] The above solid and liquid carriers can be used alone or two or more kinds can be used simultaneously.

[0079] Examples of the surfactant include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl (mono- or di-) phenyl ether, polyoxyethylene (mono-, di- or tri-) styrylphenyl ether, polyoxyethylene-polyoxypropylene block copolymer, polyoxyethylene fatty acid (mono- or di-) ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, ethylene oxide adduct of castor oil, ethylene glycol (acetylene glycol), acetylenic alcohol, ethylene oxide adduct of ethylene glycol, ethylene oxide adduct of acetylenic alcohol, and alkyl glucoside; anionic surfactants such as alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formaldehyde condensate of naphthalene sulfonic acid, salt of formaldehyde condensate of alkyl naphthalene sulfonic acid, sulfate or phosphate ester salt of polyoxyethylene alkyl ether, sulfate or phosphate ester salt of polyoxyethylene (mono- or di-) alkyl phenyl ether, sulfate or phosphate ester salt of polyoxyethylene (mono-, di- or tri-) styrylphenyl ether, polycarboxylate (e.g., polyacrylate, polymaleate, and copolymer formed from maleic acid and olefin, etc.), and polystyrene sulfonate; cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt; amphoteric surfactants such as amino acid type and inner ammonium salt type; polysiloxane surfactants; and fluorine surfactants.

[0080] The content of the above surfactant is not particularly limited, and is usually 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. In addition, the above surfactants can be used alone or two or more kinds can be used simultaneously.

[0081] In order to control various pests, it can be used directly, or appropriately diluted with water or the like, or made into a suspension form, and used in an amount effective for controlling diseases on crops where the pests are predicted to occur or at sites where their occurrence is not desired. Its application rate varies depending on various factors such as purpose, target pests, growth stage of crops, occurrence tendency of pests, climate, environmental conditions, formulation type, application method, application site, application period, etc. Generally, it is desirable to use the active ingredient at a concentration of 0.0001 to 5000 ppm, preferably 0.01 to 1000 ppm. In addition, the application rate per 10 a is usually 1 to 300 g in terms of the active ingredient.

[0082] The effective ingredient amount of the compound of the present invention is generally 0.1 to 20% by weight in the case of powder, 5 to 50% by weight in the case of emulsion, 3 to 90% by weight in the case of wettable powder, 0.1 to 20% by weight in the case of granule, 5 to 90% by weight in the case of suspension, and 3 to 90% by weight in the case of water-dispersible granule. On the other hand, the amount of the carrier in each dosage form is generally 60 to 99.9% by weight in the case of powder, 40 to 95% by weight in the case of emulsion, 10 to 90% by weight in the case of wettable powder, 80 to 99.9% by weight in the case of granule, 10 to 95% by weight in the case of suspension, and 10 to 90% by weight in the case of water-dispersible granule. In addition, the amount of the auxiliary agent is generally 0.1 to 20% by weight in the case of powder, 1 to 20% by weight in the case of emulsion, 0.1 to 20% by weight in the case of wettable powder, 0.1 to 20% by weight in the case of granule, 0.1 to 20% by weight in the case of suspension, and 0.1 to 20% by weight in the case of water-dispersible granule.

[0083] In addition, when using the compound of the present invention as a pesticide, it can also be mixed and applied with other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, synergists, fertilizers, soil conditioners, etc. as needed during formulation or spraying.

[0084] All the documents, patent applications, and technical specifications described in this specification are incorporated herein by reference to the same extent as if each document, patent application, and technical regulation were specifically and separately incorporated by reference. Detailed implementation mode

[0085] The following examples are used to illustrate the present invention and should not be construed as limiting the present invention in any way. The scope of the rights claimed by the present invention is defined by the claims.

[0086] In view of the economy and diversity of the compounds, we preferably synthesized some compounds. Among the many synthesized compounds, some are listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustrating the present invention, but do not limit the present invention. For those skilled in the art, this should not be construed as the scope of the above-mentioned subject matter of the present invention being limited to the following compounds.

[0087] Table 1 Compound structures and their 1 H NMR

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] 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. 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 starting materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar starting materials and conditions. Various isomers of the compounds and the like resulting from such modifications or variations of the preparation method of the present invention are included within the scope of the present invention. In addition, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction, etc.

[0099] The method examples provided below are used to facilitate a further understanding of the preparation method of the present invention. The specific substances, types, and conditions used are determined to be further illustrative of the present invention and are not a limitation of its reasonable scope. The reagents used in the synthesis of the compounds shown in the following table can either be purchased commercially or can be easily prepared by those of ordinary skill in the art.

[0100] Examples of representative compounds are as follows. The synthesis methods of other compounds are similar and will not be described in detail here.

[0101] 1. Synthesis of Compound 1

[0102] (1) Dissolve 1-1 (500 mg, 1.15 mmol, 1 eq) in acetonitrile (10 ml), add it to a 50 ml single-necked flask, add potassium iodide (47 mg, 0.28 mmol, 0.25 eq), 1-2 (628 mg, 2.3 mmol, 2 eq), and react at 85 °C for 12 h. Monitor the completion of the reaction, concentrate the acetonitrile, add ethyl acetate for extraction, wash the organic phase twice with saturated brine, dry it with anhydrous sodium sulfate, mix the sample, and perform normal-phase separation (EA / PE = 2 / 3) to obtain 300 mg of 1-3, yield: 37.5%.

[0103]

[0104] (2) Dissolve 1-3 (300 mg, 0.44 mmol, 1 eq) in dichloromethane (10 ml), add it to a 50-ml single-necked flask, add m-chloroperbenzoic acid (151 mg, 0.88 mmol, 2 eq), and react at room temperature for 2 h. Monitor the completion of the reaction, add water for extraction, wash the organic phase twice with saturated brine, dry it with anhydrous sodium sulfate, mix the sample, and perform normal-phase separation (EA / PE = 1 / 2) to obtain 80 mg of compound 1, yield: 26%.

[0105]

[0106] 2. Synthesis of Compound 2

[0107] (1) In a 50-ml single-necked flask, dissolve 1-1 (1 g, 2.3 mmol) in acetonitrile (20 ml), add potassium iodide (94 mg, 0.57 mmol, 0.25 eq) and 2-1 (1.1 g, 4.6 mmol, 2 eq), and react at 80 °C for 12 h. Monitor the completion of the reaction, concentrate to remove acetonitrile, add ethyl acetate for extraction, wash the organic phase twice with saturated brine, dry it with anhydrous sodium sulfate, mix the sample, and perform normal-phase separation (EA / PE = 2 / 3) to obtain 2-2 (912 mg, yield 78.1%, white solid).

[0108]

[0109] (2) In a 100-ml single-necked flask, dissolve 2-2 (912 mg, 1.5 mmol) in ethanol (50 ml), add an aqueous solution of ammonium chloride (0.16 g, 3 mmol), then add iron powder (0.17 g, 3 mmol), and react at 60 °C for 1 h. Monitor the completion of the reaction, filter while hot, concentrate the filtrate, add water for extraction, and rotary evaporate the organic phase to obtain the crude product 2-3 (549 mg, yield 63.3%, white solid).

[0110]

[0111] (3) Dissolve 2-3 (549 mg, 0.93 mmol) in 5 ml of concentrated sulfuric acid, slowly add 2 ml of aqueous formaldehyde solution dropwise under an ice bath, slowly raise the temperature to 50 °C, and react for 1 h. Monitor the reaction until the starting material disappears. Add water to the reaction solution, extract it three times with ethyl acetate, and wash it three times with saturated brine. After drying with anhydrous sodium sulfate, mix the sample and pass it through a column. Rotary evaporate the fractions to obtain 2-4 (146 mg, yield 25.9%, white solid).

[0112]

[0113] (4) Dissolve 2-4 (146 mg, 0.24 mmol) in 10 ml of THF, add pyridine (37.9 mg, 0.48 mmol), slowly dropwise add benzoyl chloride (33.6 mg, 0.24 mmol) under an ice bath, react at room temperature for 1 h, and monitor the reaction until the starting material disappears. Add water to the reaction solution, extract it three times with ethyl acetate, and wash it three times with saturated brine. After drying over anhydrous sodium sulfate, sample it and pass it through a column. Rotate the distillate to dryness to obtain 2-5 (102 mg, yield 59.6%, white solid).

[0114]

[0115] (5) Dissolve 2-5 (102 mg, 0.14 mmol) in 10 ml of DCM, add m-chloroperoxybenzoic acid (48.2 mg, 0.28 mmol), react at room temperature for 5 h, and monitor the reaction until the starting material disappears. Add water to the reaction solution, extract it three times with DCM, and wash it three times with saturated brine. After drying over anhydrous sodium sulfate, sample it and pass it through a column. Rotate the distillate to dryness to obtain Compound 2 (61 mg, yield 57.5%, white solid).

[0116]

[0117] 3. Synthesis of Compound 46

[0118] (1) In a 250 mL single-necked flask, add 1-1 (10 g, 1.0 eq, 23.09 mmol) to 100 mL of acetonitrile, successively add potassium iodide (766.5 mg, 0.2 eq, 4.62 mmol) and 46-1 (5.0 g, 1.0 eq, 23.09 mmol), displace with nitrogen three times, and heat to 80 °C and react overnight. Monitor the reaction until the starting material disappears. Concentrate the reaction solution, dilute the residue with water (50 mL), extract it with ethyl acetate (50 mL x 3), wash the organic phase with saturated brine (50 mL x 3), dry over anhydrous sodium sulfate, concentrate, sample it, and pass it through a column to obtain the product 46-2 (12.5 g, yield 88%, yellow oil).

[0119]

[0120] (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. 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, and the temperature was raised to 80 °C and reacted for 2 h. The reaction was monitored until the starting materials disappeared. The reaction solution was concentrated, the residue was diluted with water (50 mL), and then 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 loaded onto a column for purification to obtain product 46-3 (6.3 g, yield 53%, brown solid).

[0121]

[0122] (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. Paraformaldehyde (1.3 g, 4.0 eq, 43.3 mmol) was added, and the temperature was raised to 40 °C and reacted for 2 h. The reaction was monitored until the starting materials disappeared. After the reaction was completed, the reaction solution was poured into 100 mL of water, the pH was adjusted to neutral, and then 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 loaded onto a column for purification to obtain product 46-4 (3.2 g, yield 49%, white solid).

[0123]

[0124] (4) In a 50 mL single-necked flask, 46-4 (0.1 g, 1.0 eq, 167.7 μmol) was added to 5 mL of dichloromethane. 46-5 (0.04 g, 1.5 eq, 251.55 μmol) and triethylamine (0.02 g, 1.0 eq, 167.7 μmol) were added successively, and the reaction was carried out overnight at room temperature. The reaction was monitored until the starting materials disappeared. After the reaction was completed, the reaction solution was poured into 10 mL of water, and then 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 loaded onto a column for purification to obtain product 46-6 (0.1 g, yield 80%, white solid).

[0125]

[0126] (5) In a 50 mL single-necked flask, 46-6 (0.1 g, 1.0 eq, 135.80 μmol) was added to 5 mL of dichloromethane, and m-chloroperoxybenzoic acid (0.06 g, 2.0 eq, 271.59 μmol) was added. The reaction was carried out at room temperature for 2 h. The reaction was monitored until the starting material disappeared. After the reaction was completed, the reaction solution was poured into 20 mL of saturated sodium thiosulfate solution, extracted with ethyl acetate (10 mL × 3), the organic phase was washed with saturated sodium bicarbonate solution (10 mL × 3), dried over anhydrous sodium sulfate, concentrated, loaded onto a column, and the product compound 46 (0.05 g, yield 48%, white solid) was obtained.

[0127]

[0128] 4. Synthesis of Compound 76

[0129] (1) In a 50 mL single-necked flask, 46-4 (0.1 g, 1.0 eq, 167.7 μmol) was added to 5 mL of dichloromethane, and 76-1 (0.04 g, 1.5 eq, 251.55 μmol) and triethylamine (0.02 g, 1.0 eq, 167.7 μmol) were added successively. The reaction was carried out 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, extracted with ethyl acetate (10 mL × 3), the organic phase was washed with saturated brine (10 mL × 3), dried over anhydrous sodium sulfate, concentrated, loaded onto a column, and the product 76-2 (0.1 g, yield 85%, white solid) was obtained.

[0130]

[0131] (2) In a 50 mL single-necked flask, 76-2 (0.1 g, 1.0 eq, 142.57 μmol) was added to 5 mL of acetonitrile, hydrogen peroxide (0.02 g, 3.0 eq, 427.72 μmol) was added, and then sodium tungstate (0.004 g, 0.1 eq, 14.26 μmol) was added. The temperature was raised to 50 °C and the reaction was carried out for 2 h. The reaction was monitored until the starting material disappeared. After the reaction was completed, the reaction solution was concentrated, the residue was diluted with water (10 mL) and extracted with ethyl acetate (10 mL × 3), the organic phase was washed with sodium chloride solution (10 mL × 3), dried over anhydrous sodium sulfate, concentrated, loaded onto a column, and compound 76 (0.07 g, yield 48%, white solid) was obtained.

[0132]

[0133] Biological Activity Evaluation:

[0134] (1) Insecticidal Activity Test:

[0135] Pharmaceutical preparation: The original drug is dissolved in acetone, and then the liquid medicine is diluted to gradient doses with distilled water.

[0136] Application method:

[0137] Spodoptera frugiperda (leaf dipping method): Pick corn leaves without drugs and without insect-resistant genes, cut them into leaf segments 3-4 cm in length, soak them in the liquid medicine for 20 s respectively, take them out and dry them on absorbent paper, then put 3 treated leaves into a plastic box and introduce 10 3rd-instar test insects that have been starved for 2 h. Each box is one replicate, and each treatment is replicated 3 times, with the acetone contained in the highest dose as the control. After application, transfer them to the feeding conditions for rearing. After 48 h, investigate the number of dead insects and calculate the mortality rate.

[0138] Bradysia odoriphaga (droplet method + leaf dipping method): Line the bottom of a petri dish with 2 layers of filter paper, moisten the filter paper with water, then introduce 15 3rd-instar test insects that have been starved for 2 h into each dish, and then use a pipette to suck 400 μL of the liquid medicine and evenly drip it on the larvae of Bradysia odoriphaga. Then take 2-cm-long leek pseudostems, wash and dry them, soak them in the liquid medicine for 20 s respectively, take them out and dry them on absorbent paper, and place them beside the larvae of Bradysia odoriphaga in the petri dish. Each petri dish is one replicate, and each treatment is replicated 3 times, with the acetone contained in the highest dose as the control. After application, transfer them to the feeding conditions for rearing. After 48 h, investigate the results, respectively count the death situations of each treatment, and calculate the mortality rate.

[0139] Tenebrio molitor (leaf dipping method): Pick cabbage leaves without drugs and without insect-resistant genes, cut them into 2*2-cm squares, soak them in the liquid medicine for 20 s respectively, take them out and dry them on absorbent paper, then put 2 treated leaves into a plastic box and introduce 10 test insects that have been starved for 2 h. Each box is one replicate, and each treatment is replicated 3 times, with the acetone contained in the highest dose as the control. After application, transfer them to the feeding conditions for rearing. After 48 h, investigate the number of dead insects and calculate the mortality rate.

[0140] Myzus persicae (insect dipping method): Cut the leaves with insects, soak them in the liquid medicine for 5 s respectively, take them out and dry them on absorbent paper, then put them into a small plastic box with an outer diameter of 9 cm. After 48 h, investigate the number of dead insects and calculate the mortality rate.

[0141] Mythimna separata, Spodoptera litura (spraying method): Select test insects with consistent physiological states reared indoors, put them into disposable sauce cups, introduce 10 test insects with consistent growth into each cup, and put host plant leaves or stems into the cups, then use a spray tower for spraying. After spraying, tighten the lid, repeat 3 times, with the acetone contained in the highest dose as the control. After application, transfer them to the feeding conditions for rearing.

[0142] Mortality rate = (number of dead insects / number of test insects) × 100%

[0143] Table 2 Test Results of Insecticidal Activity of Representative Compounds

[0144]

[0145] Note: N represents no data; Control Compound A: Control Compound B: Control Compound C:

[0146] (2) Acute Toxicity Test on Bees:

[0147] The acute toxicity test on bees was carried out according to the method described in GB / T 31270.10-2014. The poisoning symptoms and the number of deaths were observed and recorded 96 h after treatment. The test results showed that the LD50 values of the acute oral toxicity and acute contact toxicity of Compound 1 of the present invention to bees were both greater than 2 μg a.i. / bee, while the LD50 value of the acute oral toxicity of Control Compound B (broflanilide) was 0.0008 μg a.i. / bee, and the LD50 value of the acute contact toxicity was 0.005 μg a.i. / bee. It can be seen that the toxicity of the compounds described in this application to bees is significantly reduced and the safety is better.

[0148] At the same time, through many tests, it was found that the compounds described in the present invention have excellent effects as pest control agents, especially as insecticides for agriculture and horticulture, and have 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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