Amide compounds containing 1,2,4-oxadiazole and their salts, preparation methods and uses

Abstract

The present invention discloses an amide compound containing 1,2,4-oxadiazole and its salt, preparation method and use. The compound has a structure shown in general formula I, and the definition of each substituent is as described in the specification and claims. The compound of the present invention is used as an insecticide, especially having a good control effect on armyworm, diamondback moth, cotton bollworm, Asian corn borer and rice leaf roller. #imgabs0#

Description

Technical Field

[0001] The present invention relates to amide compounds containing 1,2,4-oxadiazole and salts thereof, to methods for preparing the same, to their use as insecticide active agents, and to methods and applications of using the compounds and their compositions in preventing and controlling insect pests in agricultural, forestry and horticultural environments. Background Art

[0002] Plant diseases and insect pests are two major causes of agricultural production losses. Pest attacks on growing crops and stored crops can lead to significant reductions in yields, which in turn leads to increased production costs.

[0003] my country is a major producer and consumer of pesticides, and insecticides account for about 40% of the pesticides used. Currently, with the use of insecticides, insects are becoming more and more resistant to existing commercial insecticides, so the demand for green, high-efficiency, low-toxic, and new mode-of-action compounds is increasing day by day.

[0004] Diamide insecticides are a class of active molecules with an aromatic ring as the core and an amide bond connected at two different sites of the aromatic ring. This type of insecticide has a novel target, which is the insect nicotinic acid receptor. It has excellent stomach poison effect and certain contact activity. It has a good control effect on Lepidoptera insects, and is extremely effective on eggs and larvae. The risk of crop damage is small and the dosage is low. However, with the passage of time, the safety and resistance issues of diamide insecticides have gradually emerged. In the populations of striped stem borers in Yuyao and Xiangshan, Zhejiang, my country, cyantraniliprole, chlorantraniliprole, and tetrachlorantraniliprole all have cross-resistance with flubendiamide and chlorantraniliprole. Therefore, this type of pesticide still needs continuous innovation to reduce the occurrence of cross-resistance. Summary of the invention

[0005] The purpose of the present invention is to provide a class of novel amide compounds containing 1,2,4-oxadiazole structure and salts thereof for controlling plant pests.

[0006] In a first aspect of the present invention, there is provided a compound having a structure represented by general formula (I), an optical isomer, a cis-trans isomer or a pesticide-acceptable salt thereof,

[0007]

[0008] In the formula, each L, each Q, and each M are independently H, halogen, hydroxyl, nitro, carboxyl, cyano, C1-C8 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C2-C6 alkenyloxy, C2-C6 alkynyl, C2-C6 alkynyloxy, C1-C6 alkoxy, or C3-C6 cycloalkoxy;

[0009] Z is O, S or NR2 ;

[0010] R 2 is H, or a substituted or unsubstituted group selected from the group consisting of C1-C8 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C2-C6 alkenyloxy, C2-C6 alkynyl, C5-C7 cycloalkenyl, 4-8 membered heterocyclyl, C6-C 10 Aryl, 4-8 membered heteroaryl, -(C1-C8 alkylene)(4-10 membered heteroaryl), -(C1-C8 alkylene)(C6-C 10 aryl)-(C1-C8 alkylene) (4-10 membered heterocyclic group), -C(=O) (C1-C8 alkyl), -C(=O) (C6-C 10 aryl), -C(=O)(4-8 membered heteroaryl), -C(=O)(C3-C8 cycloalkyl), -C(=O)(4-8 membered heterocyclyl), -C(=O)(C1-C8 alkylene)(C3-C8 cycloalkyl), -C(=O)(C1-C8 alkylene)(C6-C 10 aryl), -C(=O)(C1-C8 alkylene)(4-8 membered heteroaryl), -S(=O)(C1-C8 alkyl), -S(=O)(C6-C 10 aryl), -S(=O)(4-8 membered heteroaryl), -S(=O)(C3-C8 cycloalkyl), -S(=O)(4-8 membered heterocyclyl), -S(=O)(C1-C8 alkylene)(C3-C8 cycloalkyl), -S(=O)(C1-C8 alkylene)(C6-C 10 aryl), -S(=O)(C1-C8 alkylene)(4-8 membered heteroaryl), -SO2(C1-C8 alkyl), -SO2(C6-C 10 aryl), -SO2(4-8 membered heteroaryl), -SO2(C3-C8 cycloalkyl), -SO2(4-8 membered heterocyclyl), -SO2(C1-C8 alkylene)(C3-C8 cycloalkyl), -SO2(C1-C8 alkylene)(C6-C 10 aryl), -SO2(C1-C8 alkylene)(4-8 membered heteroaryl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, hydroxy, oxo (=O), C1-C8 alkyl, halogen, C1-C8 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl;

[0011] R 1is H, or a substituted or unsubstituted group selected from the group consisting of C1-C8 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C2-C6 alkenyloxy, C2-C6 alkynyl, C5-C7 cycloalkenyl, 4-8 membered heterocyclyl, C6-C 10 Aryl, 4-8 membered heteroaryl, -(C1-C8 alkylene)(C6-C 10 aryl), -(C1-C8 alkylene)(4-10 membered heteroaryl), -(C1-C8 alkylene)(C6-C 10 aryl)-(C1-C8 alkylene) (4-10 membered heterocyclic group), -C(=O) (C1-C8 alkyl), -C(=O) (C6-C 10 aryl), -C(=O)(4-8 membered heteroaryl), -C(=O)(C3-C8 cycloalkyl), -C(=O)(4-8 membered heterocyclyl), -C(=O)(C1-C8 alkylene)(C3-C8 cycloalkyl), -C(=O)(C1-C8 alkylene)(C6-C 10 aryl), -C(=O)(C1-C8 alkylene)(4-8 membered heteroaryl), -S(=O)(C1-C8 alkyl), -S(=O)(C6-C 10 aryl), -S(=O)(4-8 membered heteroaryl), -S(=O)(C3-C8 cycloalkyl), -S(=O)(4-8 membered heterocyclyl), -S(=O)(C1-C8 alkylene)(C3-C8 cycloalkyl), -S(=O)(C1-C8 alkylene)(C6-C 10 aryl), -S(=O)(C1-C8 alkylene)(4-8 membered heteroaryl), -SO2(C1-C8 alkyl), -SO2(C6-C 10 aryl), -SO2(4-8 membered heteroaryl), -SO2(C3-C8 cycloalkyl), -SO2(4-8 membered heterocyclyl), -SO2(C1-C8 alkylene)(C3-C8 cycloalkyl), -SO2(C1-C8 alkylene)(C6-C 10 aryl), -SO2(C1-C8 alkylene)(4-8 membered heteroaryl), -SO2N(C1-C8 alkyl)(C1-C8 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, hydroxy, oxo (=O), C1-C8 alkyl, halogen, C1-C8 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl;

[0012] m is 1, 2 or 3; n1 is 1, 2, 3 or 4; n2 is 1, 2, 3 or 4.

[0013] In another preferred embodiment, L is H, fluorine, chlorine, bromine, iodine, hydroxyl, carboxyl, cyano or C1-C4 alkyl at the 2- or 3-position. In another preferred embodiment, m is 1, and L is fluorine, chlorine, bromine or iodine at the 2- or 3-position.

[0014] In another preferred embodiment, Q is H, fluorine, chlorine, bromine, iodine, hydroxyl, cyano or C1-C4 alkyl. In another preferred embodiment, n1 is 1, and Q is fluorine, chlorine, bromine or iodine.

[0015] In another preferred embodiment, n2 is 2, and each M is independently H, fluorine, chlorine, bromine, iodine, hydroxyl, carboxyl, cyano, C1-C4 alkyl, C3-C6 cycloalkyl or C1-C4 haloalkyl. In another preferred embodiment, n1 is 2, and each M is independently H, fluorine, chlorine, bromine, iodine, hydroxyl, carboxyl, cyano, methyl, ethyl, n-propyl or isopropyl.

[0016] In another preferred embodiment, Z is O or NR 2 ; R 2 is H, or is a substituted or unsubstituted group selected from the group consisting of: -C(=O)(C1-C8 alkyl), -C(=O)(C6-C 10 aryl), -C(=O)(4-8 membered heteroaryl), -C(=O)(4-8 membered heterocyclyl), -SO2(C1-C8 alkyl), -SO2(C6-C 10 The substituted groups include, but are not limited to, -SO2 (4-8 membered heteroaryl), -SO2 (C3-C8 cycloalkyl), -SO2 (4-8 membered heterocyclyl); wherein the substituted groups include, but are not limited to, halogen, cyano, C1-C8 alkyl, C1-C8 haloalkyl, nitro, hydroxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy.

[0017] In another preferred embodiment, R 1 is H, or a substituted or unsubstituted group selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, 4-8 membered heterocyclic group, C6-C 10 Aryl, 4-8 membered heteroaryl, -(C1-C4 alkylene)(C6-C 10 aryl), -(C1-C4 alkylene)(4-8 membered heteroaryl), -C(=O)(C1-C6 alkyl), -C(=O)(C6-C 10 aryl), -C(=O)(4-8 membered heteroaryl), -SO2(C1-C6 alkyl), -SO2(C6-C 10aryl), -SO2(4-8 membered heterocyclyl), -SO2N(C1-C4 alkyl)(C1-C4 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of cyano, hydroxy, oxo (=O), C1-C6 alkyl, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl.

[0018] In another preferred embodiment, the heteroaryl group is selected from: pyridyl, thiazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, piperidinyl, morpholinyl, triazolyl, pyrrolyl, pyranyl, pyrazinyl, thienyl, pyrimidinyl, furanyl.

[0019] In another preferred embodiment, L is a halogen; preferably bromine, chlorine, fluorine, iodine at the 2-position or bromine, chlorine, fluorine, iodine at the 3-position, more preferably bromine at the 2-position.

[0020] In another preferred embodiment, Q is halogen; preferably chlorine, fluorine, bromine or iodine at the 20-position; more preferably chlorine at the 20-position.

[0021] In another preferred embodiment, n2 is 2, one M is chlorine, fluorine, bromine, iodine, cyano, methyl or ethyl at position 12 or 13, and the other M is methyl, cyano or chlorine at position 14 or 15. In another preferred embodiment, n2 is 2, and M is independently halogen and C1-C4 alkyl; preferably, methyl at position 15 and disubstituted chlorine at position 13.

[0022] In another preferred embodiment, Z is NR 2 ; R 2 is H, or a substituted or unsubstituted group selected from the group consisting of: -C(=O)(C1-C8 alkyl), -C(=O)(C6-C 10 wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, C1-C8 alkyl, C1-C8 haloalkyl, nitro, hydroxy, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, and C1-C6 alkoxy.

[0023] In another preferred embodiment, R 1 is H, or a substituted or unsubstituted group selected from the group consisting of C1-C3 alkyl, C6-C 10Aryl, -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-7 membered heteroaryl), -C(=O)(C1-C6 alkyl), -C(=O)(phenyl), -C(=O)(5-7 membered heteroaryl), -SO2(C1-C4 alkyl), -SO2(phenyl), -SO2(5-7 membered heterocyclyl), -SO2N(C1-C3 alkyl)(C1-C3 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, hydroxy, oxo(=O), C1-C4 alkyl, halogen, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, C2-C4 alkynyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl.

[0024] In another preferred embodiment, the pesticide acceptable salt is a salt formed by the compound and any R in Table 1.

[0025] In another preferred embodiment, the compound is selected from the following group: compounds I-1 to I-150, II-1 to II-25, and III-1 to III-25 in Table 1.

[0026] The second aspect of the present invention provides a pesticide composition comprising:

[0027] (a) the compound of the first aspect, its optical isomers, cis-trans isomers or pesticide-acceptable salts thereof, or a combination thereof; and

[0028] (b) pesticide-acceptable carriers and / or excipients.

[0029] In another preferred embodiment, the pesticide composition further comprises an agriculturally acceptable adjuvant.

[0030] In another preferred embodiment, component (a) accounts for 0.001-99.99 wt % of the total weight of the pharmaceutical composition; preferably 0.01-99.9 wt %; more preferably 0.05-90 wt %.

[0031] Preferably, when necessary, one or more acceptable carriers in pesticide preparations may be added to the pesticide composition, and the carriers include conventional diluents, excipients, fillers, adhesives, wetting agents, absorption promoters, surfactants, lubricants, stabilizers, defoamers, diatomaceous earth, etc. in pesticide preparations; the dosage form of the prepared drug is also diverse, which may be powders, emulsions, aqueous solutions, granules, corrosion inhibitors, effervescent tablets, etc.

[0032] Preferably, the mass percentage of the compound of the present invention in the composition is 1%-90%, and the mass percentage of the compound of the present invention to the above-mentioned insecticide is 1%:99% to 99%:1%; it can be directly diluted with water and sprayed, and the preparation of the composition contains agriculturally acceptable solvents and emulsifiers, as well as cosolvents and synergists, etc. The dosage form of the composition is selected from sustained-release agents, powders, microcapsule suspensions, dispersible liquid preparations, dispersible solid preparations, seed treatment emulsions, aqueous emulsions, granules, microemulsions, oils, seeds coated with pesticides, suspension emulsions, soluble concentrates, poisonous valleys, aerosols, block baits, slow-release blocks, concentrated baits, capsule suspensions, dispersible concentrates Any one of the following: agent, emulsifiable concentrate, electrostatic spray, water-in-oil emulsion, seed treatment agent, oil-in-water emulsion, smoke can, fine granules, smoke candle, smoke tube, smoke stick, smoke sheet, smoke agent, smoke pill, granular poison bait, gasifier, ointment, hot fog agent, solid / liquid mixed agent, liquid / liquid mixed agent, cold fog agent, solid / solid mixed agent, varnish, seed treatment liquid, microgranule, oil suspension, oil, oil dispersible powder, paste, sheet poison bait, concentrated glue, pouring agent, stick agent, seed coating agent, poison bait, smear, small piece poison bait, suspension agent, suspension emulsion, water-soluble granule, soluble concentrate, film-forming oil agent, tablet, tracking powder, ultra-low volume liquid, and steam release agent.

[0033] In another preferred embodiment, the pesticide composition further comprises an insecticide selected from the group consisting of chlorpyrifos, diazinon, acetamiprid, avermectin, avermectin, spinosad, cypermethrin, cypermethrin, cypermethrin, flucythrinate, deltamethrin, cypermethrin, Beta-cypermethrin, flucythrinate, Lambda-flucythrinate, permethrin, permethrin, allethrin, cypermethrin, bifenthrin, permethrin, Ethofenprox, flumethrin, chlorfluanid, imidacloprid, acetamiprid, nitenpyram, chlorthiocarb, thiacloprid, thiamethoxam, clothianidin, dinotefuran, clothianidin, dartenam, diflubenzuron, diflubenzuron, diflubenzuron, diflubenzuron, flufenoxuron, acetamiprid, lufenuron, chlorfenapyr, flufenuron, Noliflumuron, which is flubendiamide, its CAS number is 121451-02-3, flufenuron, Nolaluron, which is flubendiamide, flufenuron, Bay sir6874 is {1-[(3,5-dichloro-4)4-nitrophenoxyphenyl 3-3-(2-chlorobenzene)-urea}, BaySIR-8514 is [1-(4-trifluoromethoxyphenyl)-3-(2-chlorobenzene)-urea}, oxathiapiron, Bistrifluron is bistrifluron, furanthinozide, chlorfenapyr, methoxyfenapyr, chlor ... Metocarb, isoprocarb, cartap, fenbutylcarb, leaf flying, carbaryl, benfuracarb, butasulfuron, cartap, bromocriptine, hexythiazox, fenpyroximate, pyridabenzan, cloftizine, fenpropimorph, diafenthiuron, benfuracarb, pymetrozine, spirocyclopent, spirotetracycline, spirotetracycline, butenefipronil, triazotin, buprofezin, cypermethrin, fipronil, insecticide, chlorantraniliprole, flubendiamide, flucythamide, cyanamide, tolfenpyrad, tebufenpyrad, bromofenpyrad, pyrazinone, etoxazole, tebufenpyrad, pyrifos, pyriproxyfen, emamectin.

[0034] The third aspect of the present invention provides the use of the compound described in the first aspect, its optical isomers, cis-trans isomers or their pesticide-acceptable salts, or the pesticide composition described in the second aspect for preparing pesticides or for controlling pests.

[0035] In another preferred embodiment, the use refers to preventing and controlling agricultural, forestry and horticultural plant pests.

[0036] Preferably, the agricultural, forestry and horticultural plants include rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, snow pea, broad bean, pea, mung bean, adzuki bean, cotton, sericulture, peanut, rape, sesame, sunflower, sugar beet, sugar cane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, pepper, radish, cucumber, cabbage, celery, mustard tuber, sugar beet, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, fruit, tea, wild vegetables, bamboo shoots, hops, rice, pepper, apple, banana, citrus, peach, papaya, orchid and bonsai.

[0037] Preferably, the insecticide controls the following pests: red spider, East Asian migratory locust, cloud-spotted locust, Chinese rice locust, Japanese yellow-spine locust, single-spined mole cricket, oriental mole cricket, rice thrips, tobacco thrips, greenhouse thrips, rice tube thrips, wheat tube thrips, greenhouse powdery wind, tobacco powdery wind, black tail leaf butterfly, big green leaf butterfly, cotton leaf butterfly, spotted clothes wrong butterfly, brown flying wind, white back flying wind, gray flying wind, sugarcane flat horned planthopper, cotton aphid, wheat aphid, wheat long tube aphid, peach aphid, sorghum aphid, radish aphid, blowing cotton scale, mulberry shield scale, arrow-pointed shield scale, pear round scale, white wax insect, red wax scale, Korean ball-hard scale, pear web stink bug, banana Web bugs, fine-horned flower bugs, tiny flower bugs, needle-edged bugs, rice spider bugs, rice brown bugs, rice black bugs, rice green bugs, green stink bugs, alfalfa stink bugs, middle black stink bugs, large lacewings, beautiful lacewings, Chinese lacewings, grain moths, clothes moths, yellow thorn moths, brown thorn moths, flat thorn moths, wheat moths, cotton bollworms, sweet potato wheat moths, diamondback moths, peach borers, soybean borers, peach borers, apple top leaf rollers, brown-banded long leaf rollers, quasi-small yellow leaf rollers, striped stem borers, bean pod borers, corn borers, yellow stem borers, cabbage borers, rice leaf rollers, striped stem borers, cotton leaf rollers, peach borers, armyworms, Spodoptera litura, rice borers , cotton bridgeworm, beet armyworm, stem borer, cotton bollworm, Dingdian diamond drill, small cutworm, large cutworm, yellow cutworm, thief moth, gypsy moth, sweet potato hawkmoth, bean hawkmoth, straight-striped rice butterfly, hidden grain butterfly, citrus swallowtail, jade-belt butterfly, cabbage butterfly, ramie red butterfly, ramie yellow butterfly, bean lycopersicon, Venus carabid, wrinkled carabid, wheat ear carabid, ditch wireworm, fine-breasted wireworm, grain spot beetle, black skin beetle, citrus small borax, golden-margin borax, yellow mealworm, black mealworm, red flour beetle, mixed flour beetle, copper green exotic beetle, dark beetle, North China black gill beetle, Mulberry longhorn beetle, star longhorn beetle, orange brown longhorn beetle, pink neck longhorn beetle, big monkey leafworm, small monkey leafworm, yellow melon guard, yellow striped flea beetle, mung bean weevil, pea weevil, broad bean weevil, corn weevil, rice weevil, wheat sawfly, pear sawfly, yellow-banded ichneumon wasp, white-star sticky insect wasp, hanging cocoon wasp, cotton bollworm tooth-lipped ichneumon wasp, black-spotted warty wasp, mosquito, fly, horsefly, red wheat midge, yellow wheat midge, rice gall midge, citrus fruit fly, melon fruit fly, wheat leaf gray leafminer, American spotted leafminer, bean stalk black leafminer, wheat stalk fly, seed fly, onion fly, radish fly, umbrella skirt chasing fly, corn borer fly, sticky insect fly without whiskers.

[0038] In another preferred embodiment, the insect pest is caused by an insect selected from the group consisting of cotton bollworm, Asian corn borer, rice leaf folder, diamondback moth, and armyworm.

[0039] The fourth aspect of the present invention provides a method for controlling insect pests, characterized in that the compound of the structure represented by the general formula (I) described in the first aspect, its optical isomers, cis-trans isomers or their pesticide-acceptable salts, or the pesticide composition described in the second aspect is applied to the environment, soil or agricultural, forestry and horticultural plants that need to be controlled.

[0040] In another preferred embodiment, the insect pest is caused by an insect selected from the group consisting of cotton bollworm, Asian corn borer, rice leaf folder, diamondback moth, and armyworm.

[0041] The invention synthesizes an amide compound containing 1,2,4-oxadiazole, has a simple and easy preparation method, simple operation, easy product purification, low cost and improved stability. The amide compound containing 1,2,4-oxadiazole of the invention has obvious insecticidal activity as confirmed by experiments and is used for preventing and controlling insect pests of crops, fruit trees, Chinese herbal medicines and flowers.

[0042] It should be understood that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features specifically described below (such as embodiments) can be combined with each other to form a new or preferred technical solution. Each feature disclosed in the specification can be replaced by any alternative feature that provides the same, equal or similar purpose. Due to space limitations, they will not be described one by one here. DETAILED DESCRIPTION

[0043] After extensive and in-depth research, the inventors of the present application have developed a series of amide compounds containing 1,2,4-oxadiazole, which have insecticidal activity and not only have obvious inhibitory effects on armyworms and diamondback moths, but also have good inhibitory activity on cotton bollworms, corn borers, and rice leaf folders, and can be used as pesticides in agricultural production.

[0044] the term

[0045] In the present invention, the term "C1-C8" refers to having 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms, and so on. "4-8 membered" refers to having 4, 5, 6, 7 or 8 ring atoms, and so on.

[0046] The term "C1-C8 alkyl" refers to a straight or branched alkyl group having 1 to 8 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or the like. The term "C2-C6 alkenyl" refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl or the like. The term "C2-C6 alkynyl" refers to a straight or branched alkynyl group having 2 to 6 carbon atoms, such as ethynyl, propynyl or the like.

[0047] The term "C3-C6 cycloalkyl" refers to a cyclic alkyl group having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or the like.

[0048] The term "C5-C7 cycloalkenyl" refers to a cyclic alkenyl group having 5 to 7 carbon atoms and having one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl or the like.

[0049] The term "C1-C6 alkoxy" refers to a straight or branched alkoxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or the like.

[0050] The term "halogen" refers to fluorine, chlorine, bromine or iodine. The term "halogenated" refers to a group substituted by the same or different one or more halogen atoms mentioned above, for example trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl or the like.

[0051] The term "alkyl" refers to an alkane molecule with one hydrogen atom missing.

[0052] The term "alkylene" refers to an alkane molecule minus two hydrogen atoms.

[0053] The term "aryl" refers to a hydrocarbon moiety containing one or more aromatic rings. For example, the term "C6-C 10 The term "aryl" refers to an aromatic ring group having 6 to 10 carbon atoms and containing no heteroatoms in the ring, such as phenyl, naphthyl, etc.

[0054] The term "heteroaryl" refers to a heteroaromatic system containing 1 to 4 heteroatoms, including nitrogen, oxygen and S(O)r (wherein r is an integer of 0, 1, or 2). For example, a 4-8 membered heteroaryl refers to a heteroaromatic system containing 4 to 8 ring atoms, and a 4-10 membered heteroaryl refers to a heteroaromatic system containing 4 to 10 ring atoms, including but not limited to pyrrolyl, furanyl, thienyl, pyrazolyl, thiazolyl, imidazolyl, oxazolyl, isoxazolyl, pyridinyl, pyranyl, pyridazinyl, pyrimidinyl, pyrazinyl, benzimidazolyl, triazolyl, and the like.

[0055] The term "heterocyclic group" refers to a cyclic group containing at least one ring heteroatom (e.g., N, O, or S). Typically, the heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens, and / or no more than 2 sulfurs. Unless otherwise indicated, the heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. Examples of heterocyclic groups include, but are not limited to, morpholinyl, hexahydroisoindolyl, tetrahydrofuranyl, tetrahydropyrrolyl, etc.

[0056] Insecticidal activity of the active substances of the invention

[0057] The term "active substance of the present invention" or "active compound of the present invention" refers to a compound of the structure shown in general formula (I) or a pesticide-acceptable salt thereof. The heterocyclic structure containing N and O has significant insecticidal activity, a broad insecticidal spectrum and strong stability.

[0058] The term "pesticide acceptable salt" means that the anion of the salt is known and acceptable when forming a pesticide pharmaceutically acceptable salt. Preferably, the salt is water-soluble. Suitable acid addition salts formed by the compound of formula (I) include salts formed by inorganic acids, such as hydrochlorides, phosphates, sulfates, nitrates; and salts formed by organic acids, such as acetates, benzoates, etc.

[0059] The compound of the present invention has good control effect on armyworm, diamondback moth, cotton bollworm, corn borer and rice leaf folder.

[0060] Insecticide composition containing the active substance of the present invention

[0061] The active substances of the present invention can be prepared into insecticide compositions by conventional methods. These active compounds can be made into conventional formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substances, microcapsules in polymers, coating compounds for seeds, and formulations used with combustion devices, such as fumigation cartridges, fumigation pots and fumigation trays, and ULV cold mist and hot mist formulations.

[0062] These preparations can be produced in a known manner, for example by mixing the active compound with an extender, i.e. a liquid, liquefied gas or solid diluent or carrier and optionally a surfactant, i.e. an emulsifier and / or dispersant and / or foam former. For example, when water is used as the extender, an organic solvent can also be used as an auxiliary agent.

[0063] When a liquid solvent is used as a diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons, for example xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, for example chlorobenzene, vinyl chloride or methylene chloride; aliphatic hydrocarbons, for example cyclohexane or paraffin, for example mineral oil fractions; alcohols, for example ethanol or ethylene glycol and their ethers and lipids; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; or less commonly used polar solvents, for example dimethylformamide, dimethyl sulfoxide and water.

[0064] A diluent or carrier for liquefied gas refers to a liquid that will become a gas at normal temperature and pressure, such as an aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

[0065] Solid carriers can be ground natural minerals, such as kaolin, clay, talc, quartz, atavistic clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicates. Solid carriers for particles are ground and classified natural zircons, such as calcite, marble, pumice, sepiolite, dolomite, inorganic and organic coarse powder synthetic particles, and organic materials such as sawdust, coconut shells, corn cobs and tobacco stem particles, etc.

[0066] Nonionic and anionic emulsifiers can be used as emulsifiers and / or foam formers. For example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysates. Dispersants include lignin sulfite waste liquor and methylcellulose.

[0067] Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, may be used in the formulation.

[0068] Colorants such as inorganic dyes, such as iron oxide, cobalt oxide and Prussian blue; organic dyes, such as azo dyes or metal phthalocyanine dyes; trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, aluminum and zinc, etc. can be used.

[0069] The active compounds of the present invention may be mixed with other active compounds in their commercial preparations or in the use formulations prepared from these preparations, and these other active compounds are insecticides, bactericides, fungicides, herbicides, growth control agents, etc. Insecticides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectin, etc., and fungicides include strobilurins, amides, triazoles, etc.

[0070] In addition, the active compounds of the present invention may also be mixed with synergists in their commercial preparations or dosage forms prepared from these preparations. These synergists are compounds that enhance the effects of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0071] These preparations usually contain 0.001-99.99% by weight, preferably 0.01-99.9% by weight, more preferably 0.05-90% by weight of the active compound of the present invention, based on the total weight of the fungicide composition. The concentration of the active compound in the commercial preparation or use formulation can vary over a wide range. The concentration of the active compound in the use formulation can be from 0.0000001-100% (g / v), preferably between 0.0001 and 1% (g / v).

[0072] Preparation method of the compound of the present invention

[0073] The compound of the general formula (I) of the present invention can be prepared by the following method, however, the conditions of the method, such as reactants, solvents, bases, the amount of the compounds used, reaction temperature, reaction time, etc. are not limited to the following explanation. The compound of the present invention can also be conveniently prepared by optionally combining various synthetic methods described in this specification or known in the art, and such combination can be easily performed by a person skilled in the art to which the present invention belongs.

[0074] The present invention is further described below in conjunction with specific examples. It should be understood that these examples are only used to illustrate the present invention and are not intended to limit the scope of the present invention. The experimental methods in the following examples that do not specify specific conditions are usually carried out under conventional conditions or under conditions recommended by the manufacturer. The materials described can be obtained from public commercial sources unless otherwise specified. Unless otherwise specified, percentages and parts are calculated by weight.

[0075] Example 1: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester

[0076] 1.1 Preparation of 2-amino-5-chloro-3-methylbenzoyl chloride

[0077]

[0078] 5.568g (30mmol) of 2-amino-5-chloro-3-methylbenzoic acid, 100ml of dichloromethane, 23.8g (200mmol) of thionyl chloride and 3 drops of DMF were added to a 500ml single-necked flask in sequence, and the temperature was raised to reflux for reaction. After 3h of reaction, the solvent was suspended to obtain 5.8g of brown product with a yield of 95%. No further treatment was performed and the next step was carried out directly.

[0079] 1.2 Preparation of N-(1-cyanomethyl)-2-amino-5-chloro-3-methylbenzamide

[0080]

[0081] 2.775g (30mmol) of aminoacetonitrile hydrochloride, 10ml of tetrahydrofuran, 10ml of water, and 5.1g (60mmol) of sodium bicarbonate were added to a 250ml three-necked flask in sequence, and a 20ml tetrahydrofuran solution containing 5.8g of 2-amino-5-chloro-3-methylbenzoyl chloride was added dropwise at -10°C. After the addition was completed, the reaction was continued to be stirred at -10°C for 2h. After 50ml of water was added to the reaction solution, it was extracted three times with 20ml of ethyl acetate, the organic phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was suspended to obtain 3.3g of product with a yield of 50%.

[0082] 1.3 Preparation of 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-yl chloride

[0083]

[0084] 3.02 g (10 mmol) of 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-carboxylic acid was added to 20 ml of dichloromethane, and 1.52 g (12 mmol) of oxalyl chloride and 3 drops of DMF were added dropwise under ice bath. After the addition, stirring was continued for 3 h. After reacting for 3 h, the solvent was suspended to dryness to obtain 3.05 g of yellow product with a yield of 95%. No further treatment was performed and the next step was carried out directly.

[0085] 1.4 Preparation of 3-bromo-N-(4-chloro-2-((cyanomethyl)carbamoyl)-6-methylphenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide

[0086]

[0087] 5mmol of N-(1-cyanomethyl)-2-amino-5-chloro-3-methylbenzamide, 20ml of acetonitrile, 5mmol of triethylamine and 5mmol of 3-bromo-1-(3-chloro-2-pyridine)-1H-pyrazole-5-acid chloride were added to a 50ml single-mouth bottle, stirred at room temperature, and the reaction was tracked by TLC. After the reaction was completed, the reaction solution was poured into 50ml of water, extracted 3 times with 20ml of dichloromethane, and the organic phase was washed with saturated ammonium carbonate, saturated sodium chloride aqueous solution and water in turn, dried over anhydrous sodium sulfate, and the solvent was suspended. The crude product was purified by column chromatography to obtain 1.27g of product with a yield of 50%. 1H NMR (400MHz, CDCl3 d)δ:10.81(s,1H),8.88(s,1H),8.61(m,1H),7.91-7.92(m,2H),7.69(s,1H ),7.55(m,1H),6.68(s,1H),4.33(s,2H),2.13(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 14 BrN6O2Cl2, calculated value: 506.9733, found value: 506.9731.

[0088] 1.5 Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester

[0089]

[0090] 2mmol of 3-bromo-N-(4-chloro-2-((cyanomethyl)carbamoyl)-6-methylphenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide was dissolved in 5ml of tetrahydrofuran, and 3mmol of tert-butyl nitrite was added. Then, 2ml of 4mol / L hydrogen chloride methanol solution was added to the reaction solution, and the reaction was tracked by TLC. After the reaction was completed, the solvent was suspended and the product was obtained by column chromatography (yield 71%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.43(dd,J=4.7,1.4Hz,1H),7.98(d,J=2.3Hz,1H),7.87(dd,J=8.1,1.5Hz,1H),7 .48(d,J=2.0Hz,1H),7.43(s,1H),7.40-7.37(m,1H),4.15(s,3H),2.28(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9632.

[0091] Example 2 Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester trifluoroacetate

[0092]

[0093] 1mmol-(2-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester, 1mmol EDCI, 0.1mmol DMAP, 1mmol trifluoroacetic acid were added to 5ml dichloromethane, and then the mixture was stirred at room temperature for 6 hours. The solvent was then suspended to dryness. The product was purified by column chromatography (yield 52%, white solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.43(dd,J=4.7,1.4Hz,1H),7.98(d,J=2.3Hz,1H),7.87(dd,J=8.1,1.5 Hz,1H),7.48(d,J=2.0Hz,1H),7.43(s,1H),7.40-7.37(m,1H),4.15(s,3H),2.28(s,3H); 19 F NMR(400MHz, CDCl3); δ-75.91; HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9636.

[0094] Example 3: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester difluoroacetate

[0095]

[0096] The synthesis of the target compound is similar to that of Example 2, except that difluoroacetic acid is used instead of trifluoroacetic acid (yield 52%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.83(s,1H),8.46(dd,J=4.7,1.4Hz,1H),8.01(d,J=2.2Hz,1H),7.90(dd,J=8.1,1.4Hz,1H),7.49(d,J=2.2Hz, 1H),7.46(s,1H),7.42(dd,J=8.1,4.7Hz,1H),5.86(t,J=53.3Hz,1H),4.16(s,3H),2.29(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9630.

[0097] Example 4: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester·3-chloro-5-trifluoromethylpyridine-2-carboxylate

[0098]

[0099] The synthesis of the target compound is similar to that of Example 2, except that 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid is used instead of trifluoroacetic acid (yield 55%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.80(s,1H),8.81-8.78(m,1H),8.45(dd,J=4.7,1.5Hz,1H),8.16-8.14(m,1H),7.99(d,J=2.4Hz, 1H),7.49-7.47(m,2H),7.45(s,1H),7.41-7.38(m,1H),4.16(s,3H),2.29(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9622.

[0100] Example 5: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester 2-trifluoromethylbenzoate

[0101]

[0102] The synthesis of the target compound is similar to that of Example 2, except that 2-trifluoromethylbenzoic acid is used instead of trifluoroacetic acid (yield 45%, yellow solid). 1H NMR (400MHz, CDCl3 d)δ:9.83(s,1H),8.46(dd,J=4.7,1.5Hz,1H),8.00(d,J=2.3Hz,1H),7.96-7.92(m,1H),7.88(dd,J=8.0,1.5Hz,1H),7.82-7.77(m,1 H),7.67-7.63(m,2H),7.49(d,J=2.3Hz,1H),7.45(s,1H),7.40(dd,J=8.0,4.7Hz,1H),4.16(s,3H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9642.

[0103] Example 6: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester 2,2-dichloroacetate

[0104]

[0105] The synthesis of the target compound is similar to that of Example 2, except that chloroacetic acid is used instead of trifluoroacetic acid (yield 45%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.46(dd,J=4.8,1.5Hz,1H),7.98(d,J=2.2Hz,1H),7.90(dd,J=8.0,1.5Hz,1H),7.48(d, J=2.0Hz,1H),7.45(s,1H),7.43-7.39(m,1H),5.89(s,1H),4.15(s,3H),2.28(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9626.

[0106] Example 7: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester 2-chlorobenzoate

[0107]

[0108] The synthesis of the target compound is similar to that of Example 2, except that 2-chlorobenzoic acid is used instead of trifluoroacetic acid (yield 45%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.82(s,1H),8.45-8.44(m,2H),7.99(d,J=2.3Hz,1H),7.89-7.84(m,2H),7.48(d,J= 2.2Hz,1H),7.42(s,1H),7.40-7.36(m,3H),3.92(s,3H),2.29(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9617.

[0109] Example 8: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester·4-trifluoromethoxybenzoate

[0110]

[0111] The synthesis of the target compound is similar to that of Example 2, except that 4-trifluoromethoxybenzoic acid is used instead of trifluoroacetic acid (yield 45%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.44(dd,J=4.7,1.5Hz,1H),8.13-8.11(m,2H),7.98(d,J=2.4Hz,1H),7.87(dd,J=8.0,1.6Hz,1H), 7.49-7.46(m,1H),7.45(s,1H),7.41-7.37(m,1H),7.30-7.27(m,2H),4.15(s,3H),2.29(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9591.

[0112] Example 9: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester 4-methylbenzoate

[0113]

[0114] The synthesis of the target compound is similar to that of Example 2, except that 4-methylbenzoate is used instead of trifluoroacetic acid (yield 45%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.43(dd,J=4.7,1.5Hz,1H),7.99(d,J=2.1Hz,1H),7.96(d,J=8.1Hz,2H),7.86(dd,J=8.0,1.6Hz,1H),7.48- 7.46(m,1H),7.44(s,1H),7.39-7.37(m,1H),7.25(d,J=8.0Hz,2H),4.15(s,3H),2.42(s,3H),2.29(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 14 BrN6O4Cl2, calculated value: 550.9631, found value: 550.9601.

[0115] Example 10: Preparation of ethyl 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylate

[0116]

[0117] The synthesis of the target compound is similar to that of Example 1.5, except that the methanol solution of hydrogen chloride is replaced by the ethanol solution of hydrogen chloride (yield 49%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.79(s,1H),8.43(dd,J=4.7,1.4Hz,1H),7.98(d,J=2.3Hz,1H),7.87(dd,J=8.1,1.5Hz,1H),7.48(d, J=2.0Hz,1H),7.43(s,1H),7.40-7.37(m,1H),4.49(q,2H),2.28(s,3H),1.33(t,3H); HRMS(ESI)m / z[M+H] + C 21 H 16 BrN6O4Cl2, calculated value: 564.9788, found value: 564.9789.

[0118] Example 11: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide

[0119]

[0120] The synthesis of the target compound is similar to that of Example 1.5, except that redistilled tetrahydrofuran is used instead of tetrahydrofuran (yield 51%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.59(s,1H),8.42(dd,J=4.7,1.5Hz,1H),7.98(d,J=2.3Hz,1H),7.89(d,J=1.6Hz,1H ),7.50(d,J=2.1Hz,1H),7.47(s,1H),7.42-7.41(m,1H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9645.

[0121] Example 12: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide 2-bromobenzoate

[0122]

[0123] The synthesis of the target compound was similar to that of Example 2, except that 2-bromobenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1 H NMR(400MHz, CDCl3)δ:9.64(s,1H),8.42(dd,J=4.7,1.5Hz,1H),7.97(d,J=2.3Hz,1H),7.90-7.88(m,1H),7.64(d,J=1.8 Hz,1H),7.62(d,J=1.4Hz,2H),7.50-7.47(m,2H),7.40-7.39(m,1H),7.38-7.37(m,1H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13BrCl2O3N7, calculated value: 535.9635, found value: 535.9625.

[0124] Example 13: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide 2-methylbenzoate

[0125]

[0126] The synthesis of the target compound was similar to that of Example 2, except that 2-methylbenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1 H NMR (400MHz, CDCl3) δ: 9.61 (s, 1H), 8.42 (dd, J = 4.7, 1.5Hz, 1H), 7.98 (d, J = 2.3Hz, 1H), 7.90-7.88 (m, 1H), 7.50 (d, J = 2.2Hz, 1H),7.48(s,1H),7.47-7.43(m,2H),7.42-7.37(m,2H),7.34(d,J=1.3Hz,1H),2.50(s,3H),2.31(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9615.

[0127] Example 14: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·3-chloro-4-trifluoromethoxybenzoate

[0128]

[0129] The synthesis of the target compound was similar to that of Example 2, except that 3-chloro-4-trifluoromethoxybenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1 H NMR(400MHz, CDCl3)δ:9.57(s,1H),8.41(dd,J=4.7,1.5Hz,1H),8.17(d,J=1.5Hz,1H),7.99(dd,J=8.6,1.6Hz,1H),7.95(d,J=2 .4Hz,1H),7.88(dd,J=8.1,1.5Hz,1H),7.48(d,J=2.3Hz,1H),7.44(s,1H),7.40-7.36(m,2H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9616.

[0130] Example 15: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·4,4,4-trifluorobutyrate

[0131]

[0132] The synthesis of the target compound is similar to that of Example 2, except that 4,4,4-trifluorobutyrylbenzoic acid is used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide is used instead of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester. (Yield 51%, yellow solid). 1H NMR (400MHz, CDCl3) δ: 9.58 (s, 1H), 8.42 (d, J = 4.6Hz, 1H), 8.00-7.97 (m, 1H), 7.91-7.87 (m, 1H), 7.51- 7.49(m,1H),7.47(s,1H),7.40(d,J=4.5Hz,1H),2.63(t,J=7.7Hz,2H),2.54-2.42(m,2H),2.31(s,3H); 19 F NMR (400MHz, CDCl3); δ-67.03ppm; HRMS (ESI) m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9628.

[0133] Example 16: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·4-cyanobenzoate

[0134]

[0135] The synthesis of the target compound was similar to that of Example 2, except that 4-cyanobenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1 H NMR (400MHz, CDCl3) δ: 9.56 (s, 1H), 8.41 (dd, J = 4.7, 2.0Hz, 1H), 8.18 (d, J = 8.5Hz, 2H), 7.95 (d, J = 2.3Hz, 1H), 7.89 (dd, J = 8. 0,1.6Hz,1H),7.77(d,J=8.5Hz,2H),7.48(d,J=2.0Hz,1H),7.44(s,1H),7.41-7.37(m,1H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9606.

[0136] Example 17: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·4-chlorobenzoate

[0137]

[0138] The synthesis of the target compound was similar to that of Example 2, except that 4-chlorobenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1 H NMR (400MHz, CDCl3) δ: 9.59 (s, 1H), 8.42 (d, J = 4.7Hz, 1H), 8.02 (d, J = 8.4Hz, 2H), 7.99-7.97 (m, 1H), 7.91-7.87 (m ,1H),7.76(d,J=8.4Hz,2H),7.50-7.48(m,1H),7.48(s,1H),7.44-7.43(m,1H),2.31(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9616.

[0139] Example 18: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·4-nitrobenzoate

[0140]

[0141] The synthesis of the target compound was similar to that of Example 2, except that 4-nitrobenzoic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester was replaced by 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide. (Yield 51%, yellow solid). 1H NMR (400MHz, CDCl3) δ: 9.59 (s, 1H), 8.46 (d, J = 5.3Hz, 1H), 8.31 (d, J = 8.8Hz, 2H), 8.25 (d, J = 8.5Hz, 2H), 8.00-7.9 7(m,1H),7.91-7.89(m,1H),7.51-7.49(m,1H),7.48(s,1H),7.42-7.40(m,1H),2.31(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9626.

[0142] Example 19: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide·6-(trifluoromethyl)nicotinic acid

[0143]

[0144] The synthesis of the target compound was similar to that of Example 2, except that 6-(trifluoromethyl)nicotinic acid was used instead of trifluoroacetic acid, and 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide was used instead of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxylic acid methyl ester. (Yield 51%, yellow solid). 1 H NMR (400MHz, CDCl3) δ: 9.59 (s, 1H), 8.48 (dd, J = 4.7, 1.5Hz, 1H), 8.42 (dd, J = 4.7, 1.5Hz, 1H), 7.98 (d, J = 2.3Hz, 1H),7.91-7.87(m,2H),7.49(d,J=2.2Hz,1H),7.47(s,1H),7.44-7.40(m,2H),2.30(s,3H); HRMS(ESI)m / z[M+H] + C 19 H 13 BrCl2O3N7, calculated value: 535.9635, found value: 535.9636.

[0145] Example 20: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl-N-(4-chlorobenzoyl)-1,2,4-oxadiazole-3-carboxamide

[0146]

[0147] 1 mmol of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide was added to 2 ml of pyridine, and 1 mmol of 4-chlorobenzoyl chloride was added at 0°C, followed by stirring at room temperature for 10 hours, and column chromatography to obtain the target compound. (Yield 45%, yellow solid). 1 H NMR (400MHz, CDCl3 d)δ:9.59(s,1H),8.43(d,J=4.7Hz,1H),8.02(d,J=8.4Hz,2H),7.99-7.97(m,1H),7.91-7.87(m,1H),7. 76(d,J=8.4Hz,2H),7.50-7.48(m,1H),7.49(s,1H),7.44-7.43(m,1H),2.32(s,3H); HRMS(ESI)m / z[M+H] + C 26 H 16 BrN7O4Cl3, calculated value: 673.9507, found value: 673.9505.

[0148] Example 21: Preparation of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl-N-methyl-1,2,4-oxadiazole-3-carboxamide

[0149]

[0150] 1mmol of 5-(2-(3-bromo-1-(3-chloropyridine-2-)-1H-pyrazole-5-carboxamide)-5-chloro-3-methylphenyl)-1,2,4-oxadiazole-3-carboxamide was added to 2ml of DMF, followed by 2mmol of sodium hydride, followed by stirring at room temperature for 2 hours, and then 2mmol of iodomethane was added after two hours, followed by stirring at 60°C for 24 hours. After the reaction, water was added and ethyl acetate was used for extraction. The organic phase was dried over anhydrous sodium sulfate, the solvent was dried, and the target compound was obtained by column chromatography. (Yield 45%, yellow solid). 1H NMR (400MHz, CDCl3 d)δ:9.59(s,1H),8.43(d,J=4.7Hz,1H),7.99-7.97(m,1H),7.91-7.87(m,1H),7.50-7.4 8(m,1H),7.49(s,1H),7.44-7.43(m,1H),2.85(s,3H),2.32(s,3H); HRMS(ESI)m / z[M+H] + C 20 H 15 BrN7O3Cl2, calculated value: 549.9791, found value: 549.9793.

[0151] The other compounds in the table were prepared using similar methods to Examples 1-21.

[0152] Example 22: Insecticidal activity test of the compounds of the present invention

[0153] Test A (Bollworm): Test units were prepared. Each unit consisted of a 250 ml plastic cup containing three-week-old cotton seedling plants. Ten third-instar larvae of the cotton bollworm were placed in each cup. The cups were sprayed with a solution of each test compound (75 / 25 acetone / distilled water) in groups of three. Each group of cups was sprayed with only one solution. The spraying method was to place the cups on a conveyor belt and pass them directly under a fan-shaped spray cone hydraulic nozzle. The nozzle sprayed at a rate of about 20 g / ha of active ingredient at a spray pressure of 30 lbs / 207 kPa. The cups were then covered and placed at 27°C and 50% relative humidity for 72 hours before data collection. The mortality of the compounds at 100 ppm is shown in Table 1.

[0154] Test B (Asian corn borer): Prepare test units consisting of a 250 ml plastic cup containing a germinated corn seed. Three test units are sprayed as described in Test A with only one test compound. After the spray has dried on the cups, place five third instar larvae of the Asian corn borer in each cup. Insert a dampened dental gauze into each cup to prevent drying and cover the cups. Then place the cups at 27°C and 50% relative humidity for 48 hours before collecting mortality data. The mortality of the compounds at 100 ppm is shown in Table 1.

[0155] Test C (Rice Leaf Folder): A set of 250 ml cups were filled with 5 adult rice leaf folders. The test method used was otherwise the same as in the test, with three cups per treatment group. Mortality data were collected 48 hours after treatment. Mortality of the compounds at 100 ppm is shown in Table 1.

[0156] Test D (Plutella xylostella): Take a 6 cm diameter petri dish, cover the bottom of the dish with a layer of filter paper, and add a proper amount of tap water to keep it moist. Select cabbage leaves from the greenhouse, remove the wax layer on the surface, use a hole punch to make a cabbage leaf disc with a diameter of 3 cm, and place the leaf with the back facing up in the petri dish. Use an Airbrush sprayer to evenly spray the front and back of the leaves (spray pressure: 10 psi, equivalent to 0.7 kg / cm 2 ; Spray volume: 0.5ml; Spray distance: 15-20cm). After the leaves are dried naturally in the shade, the third-instar larvae of Plutella xylostella are inoculated, and the clean water treatment is set as the blank control. The culture dish is moved to a standard observation room (23-25℃, RH 40-60%., L / D is 13h / 11h). During the observation period, if necessary, appropriate amount of tap water is dripped on the bottom of the dish to keep the leaf disc fresh. If the test insects eat up the treated leaf discs, untreated fresh feed can be added. The test investigation is carried out 72 hours after the treatment, and the number of dead and live insects of the test insects is recorded to calculate the mortality rate. The mortality rate of the compound at 100ppm is shown in Table 1.

[0157] Test E (Armyworm): Take 2 cm wide corn leaves grown in the greenhouse and cut them into 5 cm long leaf segments for treatment. The method is the same as the treatment method for diamondback moth. After the leaves are naturally dried in the shade, they are inoculated with 3rd instar larvae of armyworm. The test survey is carried out 72 hours after the treatment, and the number of dead and alive insects of the test insects is recorded to calculate the mortality rate. The mortality rate of the compound at 100 ppm is shown in Table 1.

[0158] Table 1. Structures of compounds of formula (I-III) and insecticidal activity test results

[0159]

[0160] (The number before the substituent represents the position)

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] Example 23: Compositions containing insecticides of the compounds of the present invention

[0178] (a) Microemulsion

[0179] Prepare the following components in proportion: 5.0% (weight percentage, the same below) of compounds I-1 to I-150, II-1 to II-25, III-1 to III-25 (Table 1); 30.0% polyvinyl pyrrolidone-vinyl acetate copolymer; 30.0% alkyl polyglycoside; 15.0% oleic acid glyceride; 20.0% water.

[0180] (b) Wettable powder

[0181] Prepare the following components in proportion: 65.0% of one of compounds I-1 to I-150, II-1 to II-25, III-1 to III-25 (Table 1); 2.0% of dodecylphenol polyglycol ether; 4.0% of sodium lignin sulfonate; 6.0% of sodium aluminum silicate; 23.0% of montmorillonite (calcined).

[0182] (c) Seed treatment agents

[0183] Prepare the following components in proportion: 20.00% of compounds I-1 to I-150, II-1 to II-25, III-1 to III-25 (Table 1); 5.00% polyvinyl pyrrolidone-vinyl acetate copolymer; 5.00% montan acid wax; 1.00% calcium lignin sulfonate; 1.00% polyoxyethylene / polyoxypropylene block copolymer; 2.00% stearyl alcohol (POE 20); 0.20% polysilicone; 0.05% colorant red dye; 65.75% water.

[0184] All documents mentioned in the present invention are cited as references in this application, just as each document is cited as reference individually. In addition, it should be understood that after reading the above teachings of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the claims attached to this application.

Claims

1. A compound having a structure represented by general formula (I) or a pesticide-acceptable salt thereof, In the formula, each L is independently H, halogen; Each Q is independently H, halogen, or C1-C8 alkyl; Each M is independently H, halogen, cyano, C1-C8 alkyl; Z is O, S or NH; R 1 is H, or a substituted or unsubstituted group selected from the group consisting of C1-C8 alkyl, C6-C 10 Aryl, -(C1-C8 alkylene)(C6-C 10 aryl), -(C1-C8 alkylene)(4-10 membered heteroaryl), -C(=O)(C1-C8 alkyl), -C(=O)(C6-C 10 aryl), -C(=O)(4-8 membered heteroaryl), -SO2(C1-C8 alkyl), -SO2(C6-C 10 aryl), -SO2(4-8 membered heteroaryl), -SO2(4-8 membered heterocyclyl), -SO2N(C1-C8 alkyl)(C1-C8 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, hydroxyl, oxo (=O), C1-C8 alkyl, C1-C8 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl; m is 1, 2 or 3; n1 is 1, 2, 3 or 4; n2 is 1, 2, 3 or 4.

2. The compound according to claim 1, or its pesticide acceptable salt, characterized in that: The compound has a structure as shown in the following formula (IA) or (IB): Where m is 1; Other substituents are as defined in claim 1.

3. The compound according to claim 1, or its pesticide acceptable salt, characterized in that: m is 1.

4. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: Q is H, fluorine, chlorine, bromine, iodine, or C1-C4 alkyl.

5. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: n1 is 1, and Q is fluorine, chlorine, bromine or iodine.

6. The compound or its pesticide acceptable salt according to claim 1, characterized in that: n1 is 2, and each M is independently H, fluorine, chlorine, bromine, iodine, cyano, or C1-C4 alkyl.

7. The compound or its pesticide acceptable salt according to claim 1, characterized in that: n1 is 2, and each M is independently H, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl or isopropyl.

8. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: Z is O or NH.

9. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: R 1 is H, or is a substituted or unsubstituted group selected from the group consisting of C1-C6 alkyl, C6-C 10 Aryl, -(C1-C4 alkylene)(C6-C 10 aryl), -(C1-C4 alkylene)(5-8 membered heteroaryl), -C(=O)(C1-C6 alkyl), -C(=O)(C6-C 10 aryl), -C(=O)(5-8 membered heteroaryl), -SO2(C1-C6 alkyl), -SO2(C6-C 10 aryl), -SO2(4-8 membered heterocyclyl), -SO2N(C1-C4 alkyl)(C1-C4 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of cyano, hydroxy, oxo (=O), C1-C6 alkyl, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl, C6-C 10 Aryl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl.

10. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: R 1 is a substituted or unsubstituted group selected from the following group: -(C1-C4 alkylene) (5-8 membered heteroaryl), -C(=O) (5-8 membered heteroaryl), -SO2 (4-8 membered heterocyclyl); wherein the heteroaryl is selected from: pyridyl, thiazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, piperidinyl, morpholinyl, triazolyl, pyrrolyl, pyranyl, pyrazinyl, thienyl, pyrimidinyl, furanyl, wherein the substitution refers to substitution by one or more groups selected from the following group: cyano, hydroxyl, oxo (=O), C1-C6 alkyl, halogen, C1-C6 haloalkyl, C3-C6 cycloalkyl, C1-C8 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, nitro, C2-C6 alkynyl.

11. The compound or pesticide-acceptable salt thereof according to claim 2, characterized in that: L is bromine, chlorine, fluorine or iodine.

12. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: The structure is shown in the following formula (IC): Wherein, Q is chlorine, fluorine, bromine or iodine, n1 is 1; and other substituents are as described in claim 1.

13. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: It is the structure shown in the following formula (I-D1~4): Wherein M2 is chlorine, fluorine, bromine, iodine, cyano, methyl or ethyl, and M1 is methyl, cyano or chlorine.

14. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: Z is NH.

15. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: R 1 is H, or a substituted or unsubstituted group selected from the group consisting of C1-C3 alkyl, C6-C 10 Aryl, -(C1-C4 alkylene)(phenyl), -(C1-C4 alkylene)(5-7 membered heteroaryl), -C(=O)(C1-C6 alkyl), -C(=O)(phenyl), -C(=O)(5-7 membered heteroaryl), -SO2(C1-C4 alkyl), -SO2(phenyl), -SO2(5-7 membered heterocyclyl), -SO2N(C1-C3 alkyl)(C1-C3 alkyl); wherein the substitution refers to substitution by one or more groups selected from the group consisting of halogen, cyano, hydroxy, oxo(=O), C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, nitro, C2-C4 alkynyl, phenyl, 4-8 membered heteroaryl, 4-8 membered heterocyclyl or C1-C6 thioalkyl.

16. The compound according to claim 1 or its pesticide acceptable salt, characterized in that: The pesticide-acceptable salt is a salt formed by the compound and any compound selected from the following groups:

17. The compound or its pesticide acceptable salt according to claim 1, characterized in that: The compound or its pesticide acceptable salt is selected from the following group: compounds I-1 to I-150, II-1 to II-25, III-1 to III-25 in Table 1; Table 1. Structures of compounds of formula (I-III) and insecticidal activity test results (The number before the substituent represents the position) 18. A pesticide composition, characterized in that: A compound having a structure represented by the general formula (I) according to any one of claims 1 to 17 or a pesticide-acceptable salt thereof; and A pesticide-acceptable carrier or excipient.

19. Use of the compound of the general formula (I) according to any one of claims 1 to 17 or its pesticide acceptable salt or the pesticide composition according to claim 18, characterized in that: (i) for the preparation of pesticides; or (ii) For pest control.

20. The use according to claim 19, characterized in that The insect pest is caused by an insect selected from the group consisting of cotton bollworm, Asian corn borer, rice leaf folder, diamondback moth, and armyworm.

21. A method for controlling pests, characterized in that: Apply the compound of the general formula (I) according to any one of claims 1 to 17 or its pesticide acceptable salt or the pesticide composition according to claim 18 to the environment, soil or agricultural, forestry and horticultural plants to be controlled.

22. The method according to claim 21, characterized in that The insect pest is caused by an insect selected from the group consisting of cotton bollworm, Asian corn borer, rice leaf folder, diamondback moth, and armyworm.

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