Isoc chromene pyridinone derivatives, processes for their preparation and uses thereof

Abstract

The present application provides a kind of containing isochromene pyridone derivatives and its preparation method and purposes, specifically related to a kind of derivatives, its chemical structure general formula see formula I: The present application discloses the general formula of the structure of the above compound, synthesis method and as insecticide, fungicide, anti-plant virus agent purposes, it is combined with agricultural acceptable adjuvant or synergist and with commercial insecticide, fungicide, anti-plant virus agent, miticide in the prevention and treatment of agricultural, forestry, horticultural plant pest, disease, viral disease purposes and preparation method.

Description

TECHNICAL FIELD

[0001] The technical scheme of the present application belongs to the field of pesticides, and specifically relates to an isochromene pyridinone derivative, a preparation method and use thereof. BACKGROUND

[0002] Pesticides are important strategic materials for ensuring stable and increased yields of crops and play an important role in national food security. However, with the large-scale use of pesticides, problems such as pesticide resistance, pesticide residues and environmental pollution have also arisen, so the creation of new pesticides with high efficiency, low toxicity, low residue and environmental friendliness has become a top priority. The creation of new pesticides is an important guarantee for the reduction and efficiency of pesticides in China. With the development of green and ecological agriculture, the creation of green pesticides has become a trend and challenge for the future development of pesticides (Shao Xusheng et al. World Pesticides, 2020, 42(04): 16-24). However, there are currently problems in the creation of new pesticides, such as a lack of original leads, a small number of green pesticide varieties, and a lack of original targets. Among them, the discovery of leads for green pesticides by modifying natural product molecules that act on the plant's own defense function is a clever solution.

[0003] The isocoumarin skeleton is widely present in natural product molecules, and its derivatives have physiological and biological activities such as antibacterial, anti-inflammatory, anticancer, protease inhibition and herbicidal activity, so the synthesis and biological activity of such compounds have attracted widespread attention. The isochromene pyridinone compound containing an isocoumarin structure can be used as an organic light-emitting diode iridium ligand (Matthew J. Jurow et al. Nature Materials, 2016, 15: 85-91), but there are few methods for synthesizing isochromene pyridinone compounds, and in these methods for constructing such derivatives, many substrates are complex, and the synthesis steps are often long and cumbersome. It is of great significance to develop a new simple and fast method for preparing isochromene pyridinone compounds and to enrich the skeleton of new potential drug molecules, laying a solid foundation for their potential applications. The present application develops a class of isochromene pyridinone derivatives and a preparation method thereof, and finds that they exhibit good bactericidal activity at low concentrations and can be used as potential bactericidal agent molecules. SUMMARY

[0004] The technical problem to be solved by the present application is to provide a new synthesis method of isochromene pyridinone derivatives, to provide the biological activity of these compounds in regulating agricultural, horticultural, and sanitary and forestry plant pests and plant pathogens and a method for determining the same, and to provide the application of these compounds in the fields of agriculture, horticulture, forestry and sanitation.

[0005] The technical scheme adopted by the present application to solve the technical problem is: a chemical structure general formula of an isochromene pyridone derivative with insecticidal, acaricidal, fungicidal, anti-plant virus, and plant disease resistance inducing activities in the fields of agriculture, horticulture, and forestry is shown as formula I:

[0006]

[0007] R 1 is selected from: hydrogen, fluorine, methoxy; R 2 is selected from: hydrogen, methyl, ethyl, isopropyl, phenyl.

[0008] The synthesis route of the isochromene pyridone derivative I and intermediates thereof in the present application is as follows:

[0009]

[0010] The synthesis method of the isochromene pyridone derivative I in the present application is divided into the following steps:

[0011] A. Preparation of compound 2:

[0012] Under inert gas protection and at -78 DEG C, equivalent n-butyllithium hexane solution is added dropwise into equivalent o-bromobenzaldehyde imine tetrahydrofuran solution, and the reaction is stirred at low temperature for 30 minutes to prepare a corresponding lithium salt solution, then the lithium salt solution is placed in a carbon monoxide atmosphere at normal pressure and stirred for 1 hour, 1 equivalent of acyl chloride is added, the reaction is carried out at room temperature for 1 hour, then the solvent is removed under reduced pressure, and the residue is purified by 200-300 mesh silica gel column chromatography with ethyl acetate / petroleum ether as the eluent to obtain the starting material 2. The acyl chloride is selected from acetyl chloride, propionyl chloride, n-butyryl chloride, phenylacetyl chloride, and isovaleryl chloride.

[0013] B. Preparation of compound 3:

[0014] At room temperature, 8.0 equivalents of concentrated sulfuric acid are added to 1 equivalent of intermediate 2 tetrahydrofuran solution, and the reaction is stirred at room temperature for 12 hours, then saturated sodium bicarbonate solution is added to quench, the liquid is separated, the aqueous phase is extracted with ethyl acetate, the combined organic phase is dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, and the residue is purified by 200-300 mesh silica gel column chromatography with ethyl acetate / petroleum ether as the eluent to obtain the isoindolinone morpholine derivative 3.

[0015] C. Preparation of compound I:

[0016] To 1 equivalent of intermediate 3 in toluene, 1.5 equivalents of acid are added and heated to 90 degrees Celsius with stirring for 9 hours. The reaction is quenched by the addition of saturated sodium bicarbonate solution, the phases are separated, the aqueous phase is extracted with ethyl acetate, the organic phases are combined and dried over anhydrous sodium sulfate, the solvent is removed under reduced pressure and the residue is purified by column chromatography on silica gel 200-300 mesh using ethyl acetate / petroleum ether as eluent to obtain the iso-chromenopyridinone derivative I. The acid is selected from the group consisting of concentrated sulfuric acid, triflic acid.

[0017] D. Use of iso-chromenopyridinone derivative I:

[0018] The present application provides the use of iso-chromenopyridinone derivative I for the preparation of a fungicide.

[0019] The present application provides the use of iso-chromenopyridinone derivative I for the preparation of an anti-tobacco mosaic virus agent.

[0020] The present application provides the use of iso-chromenopyridinone derivative I for the preparation of a plant activator for the induction of tobacco resistance to tobacco mosaic virus.

[0021] The present application provides the use of iso-chromenopyridinone derivative I for the control of pests of agricultural and forestry and horticultural plants.

[0022] E. Composition containing iso-chromenopyridinone derivative I and use thereof:

[0023] The iso-chromenopyridinone derivative I is co-applied with an agrochemical selected from the group consisting of one or more of the following: insecticide, fungicide, anti-plant virus agent, acaricide.

[0024] The iso-chromenopyridinone derivative I is combined with any one or two of the insecticides to form an insecticidal composition for the control of pests of agricultural and forestry and horticultural plants.

[0025] The insecticides mentioned are selected from: imidacloprid, difenoconazole, acetamiprid, emamectin benzoate, abamectin, spinosad, heptamethrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, deltamethrin, cypermethrin, β-cyhalothrin, λ-cyhalothrin, dichlorvos, permethrin, allethrin, bifenthrin, permethrin, fenpropathrin, flufenoxuron, cyhalothrin, imidacloprid, acetamiprid, chlorpyrifos, thiamethoxam, thiamethoxam, dinotefuran, fenpropathrin, fenpropathrin, difenoconazole, fenpropathrin, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole, difenoconazole , including: difenourea, flufenoxuron, fenflurfen, fenflurfen, furazolidone, chlorfenapyr, methoxyfenozide, cyclone dichlorvos, dichlorvos, quinalphos, pyridazin, leafhopper powder, carbaryl, imidacloprid, fenflurfen, isoprocarb, fenitrothion, sec-butylcarbide, leaf spray, carbaryl, fenitrothion, bromopropylate, thiamethoxam, azoxystrobin, pyridaben, tetradifon, propargite, difenoconazole, pymetrozine, spirodiclofen, spirotetramat, triazophos, thiamethoxam, cartap, chlorantraniliprole, tetrachlorantraniliprole, flufenoxuron, flufenoxuron, cyantraniliprole, butenpyram, azoxystrobin, bromopropylate, pyrazinone, etoxazole, pyridaben, pyridaben, pyriproxyfen, emamectin, pendimethalin:

[0026] The mass percentage of isochrome pyridone derivative I in the insecticidal composition is 1%-90%; preferably, the ratio of isochrome pyridone derivative I to the insecticide is 1%:99% to 99%:1% by mass.

[0027] The formulation of the insecticidal composition is selected from: seed treatment emulsions, water-in-oil emulsions, microemulsions, suspensions, capsule suspensions, water-soluble granules, fine granules, soluble concentrates, poison grains, block poison baits, granular poison baits, flake poison baits, concentrated poison baits, slow-release blocks, electrostatic sprays, oil-in-water emulsions, smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pellets, gas generators, ointments, hot fogging agents, cold fogging agents, aerosols, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated gels, pouring agents, seed coating agents, coating agents, film-forming oils, ultra-low volume liquids, and vapor release agents;

[0028] The plant pests controlled by the insecticidal composition are selected from: fall armyworm, spider mite, Oriental migratory locust, spotted locust, Chinese rice locust, Japanese yellow-spined locust, single-spined mole cricket, oriental mole cricket, rice thrips, tobacco thrips, greenhouse thrips, rice tube thrips, wheat tube thrips, greenhouse whitefly, tobacco whitefly, black-tailed leafhopper, large green leafhopper, cotton leafhopper, spotted lanternfly, brown planthopper, white-backed planthopper, gray planthopper, sugarcane flat-horned planthopper, cotton aphid, wheat two-forked aphid, wheat long-tubed aphid, peach aphid, sorghum aphid, radish aphid, cottony cushion scale, mulberry shield scale, arrowhead shield scale, pear round scale, white wax insect, red wax scale, Korean ball scale. Pear lace bug, banana lace bug, slender horned flower bug, miniature flower bug, needle-edged bug, rice spider-web bug, rice brown bug, rice black bug, rice green bug, green mirid bug, alfalfa mirid bug, medium black mirid bug, large lacewing, beautiful lacewing, Chinese lacewing, grain moth, clothes moth, yellow tussock moth, brown tussock moth, flat tussock moth, wheat moth, cotton bollworm, sweet potato wheat moth, diamondback moth, peach fruit moth, soybean fruit moth, peach fruit moth, apple top leafroller, brown-banded long leafroller, false yellow leafroller, rice stem borer, bean pod borer, corn borer, three-spined rice stem borer, cabbage stem borer, rice leaf roller, striped stem borer, cotton leafroller, peach borer, armyworm, sedge beetle. Noctuid moth, rice stem borer, cotton budworm, beet armyworm, large stem borer, cotton bollworm, *Diamond borer*, small cutworm, large cutworm, yellow cutworm, tussock moth, gypsy moth, sweet potato hawk moth, bean hawk moth, straight-striped rice skipper, hidden-striped rice skipper, citrus swallowtail butterfly, white-banded swallowtail butterfly, cabbage white butterfly, ramie red nymph, ramie yellow nymph, bean blister beetle, golden ground beetle, wrinkled sheath beetle, wheat ear beetle, wireworm, fine-breasted wireworm, grain bark beetle, black bark beetle, citrus small jewel beetle, golden-edged jewel beetle, yellow mealworm, black mealworm, red flour beetle, mixed flour beetle, green-green scarab beetle, dark scarab beetle, North China large Black-breasted beetle, mulberry longhorn beetle, star longhorn beetle, orange brown longhorn beetle, peach red-necked longhorn beetle, large ape leaf beetle, small ape leaf beetle, yellow cucumber beetle, yellow striped flea beetle, green bean weevil, pea weevil, broad bean weevil, corn weevil, rice weevil, wheat leaf beetle, pear fruit wasp, yellow-banded ichthys wasp, armyworm white-spotted ichthys wasp, moth larvae hanging cocoon ichthys wasp, cotton bollworm toothed ichthys wasp, moth black-spotted wart ichthys wasp, mosquito, fly, horsefly, wheat red midge, wheat yellow midge, rice gall midge, citrus fruit fly, melon fruit fly, wheat leaf gray leafminer, American serpentine leafminer, bean stalk black leafminer, wheat straw fly, seed fly, onion fly, turnip fly, umbrella-skirted parasitic fly, corn borer parasitic fly, armyworm;

[0029] The insecticidal composition controls plants selected from: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, snow pea, broad bean, pea, mung bean, adzuki bean, cotton, silkworm, peanut, rapeseed, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili pepper, radish, cucumber, cabbage, celery, pickled mustard greens, beet, rapeseed, onion, garlic, watermelon, cantaloupe, honeydew melon, papaya, apple, citrus and peach trees, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, and bonsai.

[0030] The isochromene pyridinone derivative I in combination with any one or both of the fungicides forms a fungicidal composition for controlling plant diseases in agriculture, forestry, and horticulture;

[0031] The fungicides are selected from: benzothiadiazole, thiamethoxam, methyl thiamethoxam, DL-β-aminobutyric acid, isothiazamide, ribavirin, antofenfen, ningnanmycin or salicylic acid, cymoxanil, thiram, zinc thiram, mancozeb, aluminum fosetyl-aluminum, thiophanate-methyl, chlorothalonil, dichlorvos, iprodione, benzyl benzoate, thiophanate-methyl, thiophanate-methyl, metalaxyl, flumorph, dimethomorph, high-efficiency metalaxyl, high-efficiency benzyl benzoate, diclofenac, sulfadiazine, mesotrione, thiabendazole, chlorothalonil, propiconazole, cyclopropiconazole, cyclofluoroacetate, cyclopropiconazole, cyproconazole, silthiamethoxam, carbendazim, oxidized carbendazim, carbendazim, mefenoxam, chlorpyrifos, fluopyram, furazolidone, thiabendazole, cyproconazole, pyraclostrobin, pyraclostrobin, bifenazate, fluopyram, fluorinated parabens. Azoxystrobin, fluopyram, fluopyram aniline, benzyl-fluoroquinolones, isothiazamide, fluopyram hydroxylamine, flufenoxuron, fluopyram, diyrylamide, benzylamide, ethoxysulfuron, iprodione, pyraclostrobin, azoxystrobin, fluopyram, azoxystrobin, fenoxystrobin, oxadiazon, azoxystrobin, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, oxadiazon, fenoxystrobin Azoxystrobin, propiconazole, difenoconazole, tebuconazole, high-efficiency tebuconazole, flutriafol, cyproconazole, fluquinazole, flusilazole, fenbendazole, hexaconazole, imidacloprid, tebuconazole, propiconazole, thiophanate-methyl, siloxyfenozide, tebuconazole, tetrafluoroether, triazole, tebuconazole, bifenthrin, thiamethoxam, cyproconazole, imazalil, high-efficiency imazalil, prochloraz. Fluopyram, Cyazofamid, Imidacloprid, Oxalide, Isoprothiolane, Oxalide, Pyrimethanil, Oxafloxacin, Oxafloxacin, Thiazolamide, Tebuconazole, Benzylthiocyanate, Dodecylmorpholine, Butylmorpholine, Tridemorpholine, Seed dressing, Fludioxonil, Fluazinam, Pyridabenoxac, Cyclopyridamole, Fluazinam, Pyrimethanil, Azoxystrobin, Fluazinam, Thifluzamide, Azoxystrobin, Pyrimethanil, Chlorpyrimethanil, Fluazinam, Acaricide, Dicyandioxonone, Ethoxyquinoline, Hydroxyquinoline, Propoxyquinoline, Phenoxyquinoline, Ethiocarb, Isopropamidone, Benzylthiamethoxam, Cymoxanil, Sulfocarb, Difenoconazole, Isoprothiolane, Pyridaben, Methyl thiophanate, Pyrimethanil, Kasugamycin, Polyoxin, Polyoxin, Activiamycin, Jinggangmycin, Streptomycin, Metalaxyl, Furazolidone Benzoyl, furazolidone, carbendazim, benomyl, thiophanate-methyl, triadimefon, ethirimol sulfonate, dimethomorph, ethirimol, captan, captan, thiophanate-methyl, chlorothalonil, fluchlorothalonil, chlorothalonil, isoprothiolane, isoprothiolane, tebuconazole, pentachloronitrobenzene, propineb, aluminum tris(ethylphosphonate), sulfur, Bordeaux mixture, copper sulfate, copper oxychloride, cuprous oxide, copper hydroxide, benomyl, pendimethalin, pyridaben, tetrachlorophthalide, quinclorac, spirocycline, tricyclazole, pyrazosulfuron, doxycycline, biguanide octyl salt, biguanide octylamine, chlorothalonil, benzylsulfonamide, toluenesulfonamide, indole ester, sodium dichloroisocyanurate, quinclorac, allylbenzylthiazide, bromonitol, iodomethyl, methyl methoxide, dimethoate, dazomet, dichloroisopropyl ether, thiamethoxam, fensodium, fenoxam, fenpyroxim, fenpyroximfluorofolpet, sulfuryl fluoride, dichloropropene, dichloroisocyanic acid, allylisothiazolone;

[0032] the total mass percentage content of the isochromenyl pyridone derivative I in the fungicidal composition is 1% to 90%; the ratio of the isochromenyl pyridone derivative I to the fungicide is 1%:99% to 99%:1% by mass percentage;

[0033] the processing dosage form of the fungicidal composition is selected from the group consisting of seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspending agent, water-soluble granule, fine granule, soluble concentrate, toxic grain, block toxic bait, granular toxic bait, tablet toxic bait, concentrated toxic bait, slow-release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke cartridge, smoke stick, smoke tablet, smoke pill, gas generating agent, ointment, hot fog agent, cold fog agent, aerosol, solid / liquid mixed agent, liquid / liquid mixed agent, solid / solid mixed agent, paint, microgranule, tracking powder, oil suspension, oil dispersible powder, thick adhesive, pouring agent, seed coating agent, smearing agent, film-forming oil agent, ultra-low volume liquid agent, vapor release agent;

[0034] the plant disease controlled by the fungicidal composition is selected from the group consisting of rice seedling damping-off, tomato root rot, potato late blight, tobacco black foot disease, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber downy mildew, cucumber anthracnose;

[0035] the plant suitable for the fungicidal composition is selected from the group consisting of rice, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Dutch pea, broad bean, pea, green bean, small bean, cotton, mulberry, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cacao, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, pepper, radish, cucumber, Chinese cabbage, celery, preserved vegetable, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, orange and peach, tea, wild vegetable, bamboo shoot, hops, pepper, banana, papaya, orchid, bonsai;

[0036] the isochromenyl pyridone derivative I is combined with any one or both of the antiviral agents to form an antiviral composition for controlling viral diseases of agricultural and forestry and horticultural plants;

[0037] the antiviral agent is selected from the group consisting of benzothiadiazole, thiabendazole, isothiazolyl sodium DL-β-amino butyric acid, 2,6-dichloro isonicotinic acid, N-cyanomethyl-2-chloro isonicotinamide, allyl isothiazolone, anisomycin, antofine, ningnanmycin, meththiazen or salicylic acid, peptidomycin, dichloro isonicotinic acid, allyl isothiazolone, Jinggangmycin, morpholinoguanidine hydrochloride;

[0038] The total mass percentage content of the isochrommen pyridinone derivative I in the antiviral composition is 1% to 90%; preferably, the ratio of the isochrommen pyridinone derivative I to the anti-plant virus agent is 1%:99% to 99%:1% by mass percentage;

[0039] The dosage form of the antiviral composition processed is selected from the group consisting of seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspension, water-soluble granule, fine granule, soluble concentrate, toxic bait, block toxic bait, granular toxic bait, tablet toxic bait, concentrated toxic bait, slow-release block, electrostatic spray, oil-in-water emulsion, smoke can, smoke candle, smoke cartridge, smoke stick, smoke tablet, smoke pill, gas generating agent, ointment, hot fog agent, cold fog agent, aerosol, solid / liquid mixed agent, liquid / liquid mixed agent, solid / solid mixed agent, paint, microparticle, tracking powder, oil suspension, oil dispersible powder, thick adhesive, pouring agent, seed coating agent, smearing agent, film-forming oil agent, ultra-low volume liquid agent, vapor release agent;

[0040] The viral disease to be prevented and controlled by the antiviral composition is selected from the group consisting of rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, maize dwarf mosaic virus disease, cauliflower mosaic virus disease, citrus virus disease, orchid mosaic virus disease, and orchid ring spot virus disease;

[0041] The plant to be prevented and controlled by the antiviral composition is selected from the group consisting of rice, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Dutch pea, broad bean, pea, green bean, small bean, cotton, mulberry, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cacao, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, pepper, radish, cucumber, Chinese cabbage, celery, preserved vegetable, sugar beet, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus, and peach tree, tea, wild vegetable, bamboo shoot, hops, pepper, banana, papaya, orchid, and bonsai.

[0042] The isochrommen pyridinone derivative I is combined with any one or both of the acaricides to form an acaricidal composition for preventing and controlling mite damage to agricultural and forestry and horticultural plants;

[0043] The acaricides are selected from: dichlorvos, heptamethrin, methamidophos, dibromophos, pyrimiphos, chlorpyrifos, ethion, chlorfenapyr, fenpropathrin, methyl pyrimiphos, quinalphos, abamectin, acephate, chlorpyrifos, fenpropathrin, bifenthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, flufenoxuron, deltamethrin, bifenazate, benzalkonium chloride, methyl ethyl methyl methoxide, chlorpyrifos, chlorfenapyr, chlorpyrifos, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr, chlorfenapyr. Carbendazim, thiamethoxam, tebufenozide, benzyl benzoate, bromopropylate, diflubenzuron, fenpyroximate, flufenoxuron, liuyangmycin, chlorfenapyr, thiophanate-methyl, acaricide, liuyangmycin, avermectin, doramectin, epoxim, ivermectin, selamectin, moxibustion, pyrethroid, nicotine, matrine, azadirachtin, rotenone, pyridaben, pyridaben, azoxystrobin, tetradifon, propargite, thiamethoxam, spirodiclofen, pyrimethanil, dicofol, dicofol, pyridaben;

[0044] The total mass percentage of the isochromene pyridinone derivative I in the acaricide composition is 1%-90%; the ratio of the isochromene pyridinone derivative I to the acaricide is 1%:99% to 99%:1% by mass percentage.

[0045] The formulation of the acaricide composition is selected from: seed treatment emulsions, water-in-oil emulsions, microemulsions, suspensions, capsule suspensions, water-soluble granules, fine granules, soluble concentrates, poison grains, block poison baits, granular poison baits, flake poison baits, concentrated poison baits, slow-release blocks, electrostatic sprays, oil-in-water emulsions, smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pellets, gas generators, ointments, hot fogging agents, cold fogging agents, aerosols, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated gels, pouring agents, seed coating agents, coating agents, film-forming oils, ultra-low volume liquids, and vapor release agents;

[0046] The mites controlled by the acaricide composition are selected from the following: the mites are selected from the Tetranychidae, Tetranychidae, Fusarium, Eriophyridae, Chlorella, and Eriophyridae families, and the mites are global agricultural mites, forestry mites, horticultural mites and sanitary mites.

[0047] The acaricide composition is used to control plants selected from: rice, wheat, barley, oats, corn, sorghum, sweet potato, potato, cassava, soybean, snow pea, broad bean, pea, mung bean, adzuki bean, cotton, silkworm, peanut, rapeseed, sesame, sunflower, beet, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconut, oil palm, sisal, tobacco, tomato, chili pepper, radish, cucumber, cabbage, celery, pickled mustard greens, beet, rapeseed, onion, garlic, watermelon, cantaloupe, honeydew melon, papaya, apple, citrus and peach trees, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, and bonsai.

[0048] The biological activity of the isochromene pyridone derivative I of the present application is determined as follows:

[0049] The fungicidal activity of the isochromene pyridone derivative I of the present application is determined as follows:

[0050] The fungicidal or bacteriostatic activity of the isochromene pyridone derivative I of the present application is determined by the mycelial growth rate method, and the specific steps are as follows: 1.8 mg of the sample is dissolved in 2 drops of dimethyl sulfoxide, and then diluted to 500 μg / mL of the agent with an aqueous solution containing a certain amount of Tween 20 emulsifier, 1 mL of the test agent is taken in each sterile culture dish, 9 mL of PDA medium is added, shaken uniformly to prepare a drug-containing plate of 50 μg / mL, and a plate with 1 mL of sterile water is used as a blank control, a 4 mm diameter puncher is used to cut the mycelium along the outer edge of the dish, and then placed on the drug-containing plate in an equilateral triangle, 3 replicates are performed for each treatment, the culture dishes are placed in a constant temperature incubator at 24±1℃, and after the control colony diameter expands to 2-3 cm, the expansion diameter of each treatment dish is investigated, the average value is calculated, compared with the blank control, the relative bacteriostatic rate is calculated, and the test strains are most of the typical plant pathogenic species actually occurring in the field of agricultural production in China, the codes and names of which are as follows: A.s: Alternaria solani, B.c: Botrytis cinerea, C.a: Cercospora arachidicola, F.g: Fusarium graminearum, P.p: Physalospora piricola, R.s: Rhizoctonia solani, S.s: Sclerotinia sclerotiorum.

[0051] The present application has the advantages that the isochromene pyridone derivative I is synthesized, and the bacteriostatic activity of the isochromene pyridone derivative I is screened.

[0052] The present application further specifically illustrates the synthesis, biological activity and application of the isochromene pyridone derivative I through specific preparation and biological activity determination examples, and the examples are only used to specifically illustrate the present application but not to limit the present application, especially the biological activity is only used to illustrate but not to limit the present patent, and the specific embodiments are as follows:

[0053] Example 1: Preparation of compound I-1:

[0054] (1) In a 500 mL Schlenk flask, 1-(2-bromophenyl)-N-(2,2-diethoxyethyl)formimidate (4.8 g, 16.0 mmol) and 200 mL of tetrahydrofuran were added, and under inert gas protection and at -78°C, n-butyllithium hexane solution (10 mL, 16.0 mmol) was added dropwise into the tetrahydrofuran solution, and the reaction was stirred at low temperature for 30 minutes to prepare a corresponding lithium salt solution. Then, the lithium salt solution was placed in a one-atom carbon monoxide atmosphere under normal pressure and stirred for 1 hour. Propionyl chloride (1.36 mL, 16.0 mmol) was added, and after the reaction was performed at room temperature for 1 hour, the solvent was removed under reduced pressure. The residue was purified by column chromatography on 200-300 mesh silica gel, and eluted with ethyl acetate / petroleum ether = 1:3 (volume ratio) to obtain 2-(2,2-diethoxyethyl)-3-propionylisoindolin-1-one as a yellow oil, 2.02 g, in a yield of 41%.

[0055] (2) In a 500 mL single-necked round-bottom flask, 2-(2,2-diethoxyethyl)-3-propionylisoindolin-1-one (3.5 g, 11.5 mmol) was dissolved in 300 mL of dichloromethane solution, and concentrated sulfuric acid (5.0 mL, 91.7 mmol) was added dropwise. After stirring at room temperature for 12 hours, 300 mL of saturated sodium bicarbonate solution was added to quench, and the water layer was separated and extracted with 150 mL of ethyl acetate twice. The combined organic layer was washed with 200 mL of saturated sodium chloride solution once, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on 200-300 mesh silica gel, and eluted with ethyl acetate / petroleum ether = 3:1 (volume ratio) to obtain 1-ethyl-3-hydroxy-3,4-dihydro-6H-[1,4]-oxazino-[3,4-a]-isoindol-6-one as a yellow oil, 1.73 g, in a yield of 65%.

[0056] (3) In a 100 mL single-necked round-bottom flask, 1-ethyl-3-hydroxy-3,4-dihydro-6H-[1,4]-oxazino-[3,4-a]-isoindol-6-one (1.73 g, 7.49 mmol) was dissolved in 50 mL of toluene, and trifluoromethanesulfonic acid (1.0 mL, 11.23 mmol) was added dropwise. After heating to 90°C and stirring for 9 hours, 200 mL of saturated sodium bicarbonate solution was added to quench, and the water layer was separated and extracted with 150 mL of dichloromethane three times. The combined organic layer was washed with 200 mL of saturated sodium chloride solution once, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on 200-300 mesh silica gel, and eluted with ethyl acetate / petroleum ether = 1:7 (volume ratio) to obtain I-1 as a yellow solid, 1.16 g, in a yield of 73%.

[0057] Example 2: Results of the determination of the antibacterial activity of the iso-chromenopyridone derivative I of the present application:

[0058] The common plant pathogenic fungi codes and names tested in the present application are as follows: A.s: Alternaria solani, B.c: Botrytis cinerea, C.a: Cercospora arachidicola, F.g: Fusarium graminearum, P.p: Physalospora piricola, R.c: Rhizoctonia cerealis, R.s: Rhizoctonia solani, S.s: Sclerotinia sclerotiorum. These strains are well representative and can represent most of the pathogenic fungi in the field of agricultural production.

[0059] The determination results of the mycelial growth rate method are shown in Table 2, which shows that all the synthetic compounds of the present application have different degrees of fungicidal activity at 50 μg / ml. The present application uses thifluzamide as a positive control to carry out the determination of the biological activity of the new compounds; the results show that for tomato early blight, the fungicidal activity of compounds I-2, I-4, I-5, I-6, I-7 and I-8 is more than 50%, among which the inhibition rate of I-7 is 66%, and the inhibition rate of the control thifluzamide is 65%; for cucumber gray mold, the fungicidal activity of compounds I-7 and I-8 is more than 70%, among which the inhibition rate of compound I-8 reaches 89%, and the inhibition rate of the control thifluzamide is 59%; for peanut brown spot, the inhibition rates of compounds I-5, I-8 and I-11 are more than 70%; for Fusarium graminearum, the inhibition rates of compounds I-4 and I-7 are more than 60%, which is 35% higher than the positive control thifluzamide; for apple ring rot, the fungicidal activity of compounds I-4, I-5, I-7, I-8 and I-11 is more than 50%, which is 39% higher than the positive control thifluzamide; for rice sheath blight, the inhibition rates of compounds I-1, I-2, I-4, I-5, I-6, I-7, I-8, I-11 and I-12 are more than 60%; for Sclerotinia sclerotiorum, the fungicidal activity of compounds I-4, I-6, I-7 and I-8 is more than 50%. In summary, compounds I-5, I-7 and I-8 show high fungicidal activity.

[0060] Example 3: Application of the isochromene pyridone derivative I of the present application in preparing a pesticide composition:

[0061] The isochromene pyridinone derivative I of the present application is used for the preparation of a pesticidal composition, which comprises the isochromene pyridinone derivative I of the present application and its intermediates as active ingredients, the mass percentage of the active ingredients being 0.1% to 99.9%, the mass percentage of solid or liquid adjuvants being 99.9% to 0.1%, and optionally 0 to 50% of surfactants.

[0062] Example 4: Use of the isochromene pyridinone derivative I of the present application for the preparation of a pesticidal composition:

[0063] The isochromene pyridinone derivative I of the present application and its intermediates can be used in combination with other commercial pesticides, i.e. insecticides, acaricides, fungicides, antiviral agents or plant activators to prepare a pesticidal composition, which comprises the isochromene pyridinone derivative I of the present application and its intermediates and the other commercial pesticides, i.e. insecticides, acaricides, fungicides, antiviral agents or plant activators as active ingredients, the ratio of the isochromene pyridinone derivative I of the present application and its intermediates to the other commercial pesticides, i.e. insecticides, acaricides, fungicides, antiviral agents or plant activators being 1%:99% to 99%:1% by mass percentage, the mass percentage of the active ingredients being 0.1% to 99.9%, the mass percentage of solid or liquid adjuvants being 99.9% to 0.1%, and optionally 0 to 50% of surfactants.

[0064] Example 5: Use of the isochromene pyridinone derivative I of the present application in combination with insecticides for the control of pests of agricultural and forestry and horticultural plants:

[0065] The present invention provides an insecticidal composition for controlling pests in agricultural, forestry, and horticultural plants by combining the isocyanate-containing pyridinone derivative I with any one or two commercial insecticides. The commercial insecticides are selected from: imidacloprid, difenoconazole, acetamiprid, emamectin, bamectin, spinosad, fenflurfen, cypermethrin, lambda-cyhalothrin, deltamethrin, deltamethrin, cypermethrin, β-cypermethrin, λ-cypermethrin, dichlorvos, permethrin, allethrin, bifenthrin, permethrin, fenflurfen, flufenoxuron, cypermethrin, pyrethrin, etc. Imidacloprid, acetamiprid, chlorpyrifos, thiamethoxam, thiamethoxam, dinotefuran, conidine, datnam, diflubenzuron, diflubenzuron, flufenoxuron, flufenoxuron, acetamiprid, lufenuron, fenflurfen, flufenoxuron, polyfluorourea, flufenoxuron, difenoflubenzuron, flufenoxuron, fenflurfen, fenflurfen, chlorfenapyr, methoxyfenozide, cyclophosphamide, dichlorvos, quinalphos, pyridaben, leafhopper spray, carbaryl, imidacloprid, fenpropathrin, isoprocarb, fenitrothion, sec-butylcarbide, leaf spray, carbaryl, fenitrothion, bromopropylate, thiamethoxam, azoxystrobin, pyridaben, tetradifon, propargite, The insecticide composition contains the following compounds: tebufenozide, pymetrozine, spirodiclofen, spirotetramat, spirotetramat ethyl ester, triazophos, thiamethoxam, cartap, chlorantraniliprole, tetrachlorantraniliprole, flufenoxuron, flufenoxuron, cyanantraniliprole, butenpyram, acetamiprid, brofenoxuron, pyrazinone, etoxazole, pyridoxamine, pyridoxin, pyriproxyfen, emamectin, pendimethalin; the isochromene pyridinone derivative I of the present invention is present in a mass percentage of 1%-90% in the insecticide composition, and the ratio of isochromene pyridinone derivative I of the present invention to the aforementioned commercial insecticides is 1%:99% to 99%:1% by mass percentage; the formulation of the insecticide composition is as follows. Selected from: Seed treatment emulsions, water-in-oil emulsions, microemulsions, suspensions, capsule suspensions, water-soluble granules, fine granules, soluble concentrates, poisoned grains, block poisoned baits, granular poisoned baits, flake poisoned baits, concentrated poisoned baits, slow-release blocks, electrostatic sprays, oil-in-water emulsions, smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pellets, gas generators, ointments, hot fogging agents, cold fogging agents, aerosols, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated gels, pouring agents, seed coating agents, coating agents, film-forming oils, ultra-low volume liquids, vapor release agents;The plant pests suitable for the insecticidal composition are selected from the group consisting of Spodoptera litura, red spider, Locusta migratoria, Oedaleus asiaticus, Chinese rice locust, Japanese yellow stripe locust, single-spined mole cricket, oriental mole cricket, rice plant hopper, tobacco plant hopper, greenhouse whitefly, rice white-backed planthopper, small brown planthopper, white-backed planthopper, green leafhopper, large green leafhopper, cotton leafhopper, white-backed planthopper, brown planthopper, white-backed planthopper, small brown planthopper, cotton aphid, wheat aphid, wheat aphid, peach aphid, sorghum aphid, radish aphid, cotton lace bug, mulberry shield bug, arrowhead shield bug, pear scale insect, white wax insect, red wax insect, Korean ball scale insect, pear netted bug, banana netted bug, tiny flower bug, small flower bug, needle-winged bug, rice spider bug, rice brown bug, rice black bug, rice green bug, green plant bug, alfalfa plant bug, medium black plant bug, large green lacewing, beautiful green lacewing, Chinese green lacewing, rice moth, clothes moth, yellow-streaked moth, brown-streaked moth, flat-streaked moth, wheat moth, cotton red bollworm, sweet potato moth, diamondback moth, peach fruit moth, soybean fruit moth, peach fruit moth, apple top-rolling leaf moth, brown-banded leaf-rolling moth, small yellow-rolling leaf moth, rice stem borer, bean podworm, corn borer, rice stem borer, cabbage caterpillar, rice leaf-rolling wild moth, peach leaf-rolling wild moth, pine caterpillar, oriental armyworm, rice borer, cotton webworm, sugar beet armyworm, cotton bollworm, diamondback moth, large black ground beetle, large ground beetle, yellow ground beetle, poisonous moth, dancing moth, sweet potato moth, bean moth, rice brown stripe, rice green stripe, citrus fruit fly, melon fruit fly, wheat leaf miner, American spotted leaf miner, bean stem borer, wheat stem borer, seed fly, onion fly, radish fly, umbrella skirt parasitic fly, corn borer parasitic fly, pine caterpillar; and the plants suitable for the insecticidal composition are selected from the group consisting of rice, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Dutch pea, broad bean, pea, green bean, small bean, cotton, mulberry, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cacao, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, pepper, radish, cucumber, Chinese cabbage, celery, preserved vegetable, sugar beet, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, orange and peach trees, tea, wild vegetable, bamboo shoot, hops, pepper, banana, papaya, orchid, bonsai.

[0066] Example 6: Use of the isochromene pyridinone derivative I according to the application in combination with a fungicide for controlling plant diseases in agriculture and forestry and in horticulture:

[0067] The present invention comprises a fungicide composition for controlling diseases of agricultural, forestry, and horticultural plants by combining the isocyanate-containing pyridinone derivative I with any one or two commercial fungicides. The commercial fungicides are selected from: benzothiadiazole, thiamethoxam, methyl thiamethoxam, isothiazine, ribavirin, anthraquinone, ningnanmycin or salicylic acid, cymoxanil, thiram, thiram, mancozeb, fosetyl-aluminum, thiophanate-methyl, chlorothalonil, dichlorvos, iprodione, benzyl benzoate, thiophanate-methyl, thiophanate-methyl, metalaxyl, flumorph, dimethomorph, high-efficiency metalaxyl, high-efficiency benzyl benzoate, cyhalofop-p-ethyl, sulfadiazine, mesotrione, thiabendazole, chlorothalonil, propiconazole, cyclopropiconazole, cyclofluoroacetate, cyclopropiconazole, cyhalofop-p-ethyl, silthiamethoxam, carbendazim, oxychloride, methyl thiophanate ... Amide, sulfadiazine, fluopyram, furopyram, thifluzamide, cyproconazole, pyraclostrobin, pyraclostrobin, bifenthiophanate-methyl, fluopyram, fluoxastrobin, fluoxastrobin, fluoxastrobin aniline, benzyl-fluoroquinolone, isopyram, fluoxastrobin hydroxylamine, flufenoxuron, fluoxastrobin, diyrylamide, benzylamide, ethoxysulfuron, iprodione, pyraclostrobin, ether amine Fluopyram, azoxystrobin, fenoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, oxadiazon, tebuconazole, oxadiazon ... Silfluzazole, Tebuconazole, Tebuconazole, Triazole, Mefenoxam, Bifenthrin, Thiamethoxam, Wheat-Spinning Agent, Imazalil, High-efficiency Imazalil, Prochloraz, Fluopyram, Cyazofamid, Imidacloprid, Oxamid, Isoprothiolane, Oxamid, Pyrimethanil, Oxamid, Oxamid, Thiazolamide, Oxythiazoline, Thioxam, Phoxim, Benzothiazoline, Dodecyl Morpholine, Butylmorpholine, Tridemorpholine, Seed Treatment Fluroxyfen, fluazinam, fluazinam, pyridaben, cyclopyridamole, fluazinam, pyridaben, pyrimethanil, thifluzamide, pyrimethanil, chlorpyrifos, fluazinam, abamectin, dicyandioxonone, ethoxyquinoline, hydroxyquinoline, propoxyquinoline, phenoxyquinoline, ethoxycarb, isopyram, benomyl, cymoxanil, sulfadiazine, difenoconazole, isopyram, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil, pyrimethanil Phoxim, methyl thiophanate, cymoxanil, kasugamycin, polyoxin, polyoxin, effectivemycin, jinggangmycin, streptomycin, metalaxyl, furazolidone, benzalkonium chloride, furazolidone, carbendazim, benomyl, thiophanate-methyl, triadimefon, ethirimol sulfonate, dimethomorph, ethirimol, captan, captan, vinclozolin, chlorothalonil, isoprothiolane, isoprothiolane, tebuconazole, pentachloronitrobenzene, propineb, aluminum triethylphosphonate, sulfur, Bordeaux mixture, copper sulfate, copper oxychloride, cuprous oxide, copper hydroxide, benomyl, pendimethalin, pyridaben, tetrachlorophthalide, quinolones, spirocycline, tricyclazole, pyrazosulfuron, doxycycline, chlorpyrifos, biguanide octyl salt, biguanide octylamine, chlorothalonil, benzylsulfonamide, toluenesulfonamide, indole ester, sodium dichloroisocyanurateQuinacram, allylbenzylthiazide, bromonitol, iodomethane, methyl methoxide, dimethoate, dazomet, dichloroisopropyl ether, thiamethoxam, fenpropathrin, fenpropathrin, fenpropathrin, thiamethoxam, thiocarbamate, thiocarbamate, thiocarbamate, thiocarbamate, dichloropropene, dichloroisonicotinic acid, allylisothiazide; the total mass percentage of isochromene pyridinone derivative I in the bactericidal composition of the present invention is 1%-90%, and the mass percentage of isochromene pyridinone derivative I of the present invention to the aforementioned commercial bactericides is 1%:99% to 99%:1. %; The formulation of the bactericidal composition is selected from: seed treatment emulsions, water-in-oil emulsions, microemulsions, suspensions, capsule suspensions, water-soluble granules, fine granules, soluble concentrates, poisoned grains, block poisoned bait, granular poisoned bait, flake poisoned bait, concentrated poisoned bait, slow-release blocks, electrostatic sprays, oil-in-water emulsions, smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pellets, vaporizers, ointments, hot fogging agents, cold fogging agents, aerosols, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures. The fungicidal composition includes lacquer, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated colloids, pour-over agents, seed coating agents, coating agents, film-forming oils, ultra-low volume liquids, and vapor release agents. The plant diseases for which the fungicidal composition is applicable are selected from: rice seedling rot, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber downy mildew, and cucumber anthracnose. The plants for which the fungicidal composition is applicable are selected from: rice, wheat, barley, oats, corn, sorghum, and sugarcane. Potatoes, cassava, soybeans, snow peas, broad beans, peas, mung beans, adzuki beans, cotton, silkworms, peanuts, rapeseed, sesame, sunflowers, beets, sugarcane, coffee, cocoa, ginseng, fritillaria, rubber, coconuts, oil palm, sisal, tobacco, tomatoes, chili peppers, radishes, cucumbers, cabbage, celery, pickled mustard greens, beets, rapeseed, scallions, garlic, watermelons, cantaloupes, honeydew melons, papayas, apples, citrus fruits and peaches, tea, wild vegetables, bamboo shoots, hops, pepper, bananas, papayas, orchids, bonsai.

[0068] Example 7: Application of the combination of the isochoride-containing pyridinone derivative I and an anti-plant virus agent in the prevention and control of viral diseases in agricultural, forestry, and horticultural plants:

[0069] The isochrommen pyridone derivative I of the present application is combined with any one or two of the commercial antiviral agents selected from the group consisting of benzothiadiazole, thiabendazole, isothiocyanate, anisomycin, antofine, ningnanmycin, methysticin or salicylic acid, peptidomycin, dichloroisocyanic acid, allyl isothiazole, jingangmycin, and morpholinoguanidine hydrochloride to form an antiviral composition for preventing and treating viral diseases of agricultural and forestry and horticultural plants. The total mass percentage of the isochrommen pyridone derivative I of the present application in the antiviral composition is 1% to 90%, and the ratio of the isochrommen pyridone derivative I of the present application to the aforementioned commercial antiviral agents is 1%:99% to 99%:1% by mass percentage. The antiviral composition is processed into a dosage form selected from the group consisting of a seed treatment emulsion, a water emulsion, a microemulsion, a suspension emulsion, a capsule suspension, a water-soluble granule, a fine granule, a soluble concentrate, a toxic grain, a block toxic bait, a granular toxic bait, a tablet toxic bait, a concentrated toxic bait, a slow-release block, an electrostatic spray, an oil-in-water emulsion, a smoke can, a smoke candle, a smoke cartridge, a smoke stick, a smoke tablet, a smoke pill, a gas-releasing agent, an ointment, a hot fog agent, a cold fog agent, an aerosol, a solid / liquid mixed agent, a liquid / liquid mixed agent, a solid / solid mixed agent, a paint, a microgranule, a tracking powder, an oil suspension, an oil dispersible powder, a thick adhesive, a pour-on agent, a seed coating agent, a smearing agent, a film-forming oil agent, an ultra-low volume liquid agent, and a steam release agent. The viral diseases prevented and treated by the antiviral composition are selected from the group consisting of rice dwarf disease, yellow dwarf disease, streak disease, tomato fern leaf virus disease, pepper mosaic virus disease, tobacco vein necrosis virus disease, maize dwarf mosaic virus disease, cauliflower mosaic virus disease, citrus virus disease, cymbidium mosaic virus disease, and cymbidium ring spot virus disease. The plants prevented and treated by the antiviral composition are selected from the group consisting of rice, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Dutch pea, broad bean, pea, mung bean, small bean, cotton, mulberry, peanut, rape, sesame, sunflower, sugar beet, sugarcane, coffee, cacao, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, pepper, radish, cucumber, Chinese cabbage, celery, preserved vegetable, rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, citrus, and peach, tea, wild vegetable, bamboo shoot, hops, pepper, banana, papaya, orchid, and bonsai.

[0070] Example 8: Application of the isochrommen pyridone derivative I of the present application in combination with a miticide in preventing and treating mite damage to agricultural and forestry and horticultural plants:

[0071] The isochrommen pyridone derivative I of the present invention is combined with any one or two of the commercial acaricides selected from dichlorvos, heptenophos, phosalone, naled, pyrimiphos-methyl, sulfotep, ethion, chlorphenothion, phosmet, pirimiphos-methyl, quinalphos, propetamphos, propetanphos, phosmet, phosalone, fluoroxyrene, bifenthrin, lambda-cyhalothrin, gamma-cyhalothrin, fenpropathrin, acrinathrin, flumethrin, chlorofluazuron, chlorobenzilate, fenbutatin-oxide, carbaryl, propoxur, pirimicarb, bensultap, thiocarboxime, chlorobenzilate, bromopropylate, diofenolan, chinomethionat, flucycloxuron, flufenoxuron, luyangmycin, chongmuycin, thuringiensin, spinosyn, avermectin, doramectin, eprinomectin, ivermectin, selamectin, moxidectin, pyrethrin, nicotine, matrine, azadirachtin, rotenone, pyridaben, pyridaben, azocyclotin, clofentezine, chinomethionat, hexythiazox, spirodiclofen, spiromesifen, chlorfoprop-methyl, propargite, pyridaben, and pyridaben to form an acaricidal composition for controlling acarid pests of agricultural and forestry and horticultural plants; the total mass percentage of the isochrommen pyridone derivative I of the present invention in the acaricidal composition is 1% to 90%, the ratio of the isochrommen pyridone derivative I of the present invention to the commercial acaricides is 1%:99% to 99%:1% by mass percentage; the processing dosage form of the acaricidal composition is selected from seed treatment emulsion, water emulsion, microemulsion, suspoemulsion, capsule suspensions, water-soluble granules, fine granules, soluble concentrate, toxic grains, block toxic bait, granular toxic bait, tablet toxic bait, concentrated toxic bait, slow-release block, electrostatic spray, oil-in-water emulsion, smoke canister, smoke candle, smoke cartridge, smoke stick, smoke tablet, smoke pill, gas-releasing agent, ointment, hot fogging agent, cold fogging agent, aerosol, solid / liquid mixed agent, liquid / liquid mixed agent, solid / solid mixed agent, paint, microgranule, tracking powder, oil suspension, oil-dispersible powder, thick paste, pour-on, seed coating, smearing agent, film-forming oil, ultra-low volume liquid, steam release agent; the acarid pests controlled by the acaricidal composition are selected from the family Tetranychidae, the family Tenuipalpidae, the family Empoascidae, the family Eriophyidae, the genus Tetranychus, and the family Eriophyidae, which are world-wide agricultural, forestry, horticultural and sanitary acarid pests; the plants controlled by the acaricidal composition are selected from rice, wheat, barley, oat, corn, sorghum, sweet potato, potato, cassava, soybean, Dutch pea, broad bean, pea, mung bean, cotton, mulberry, peanut, oilseed rape, sesame, sunflower, sugar beet, sugarcane, coffee, cacao, ginseng, fritillaria, rubber, coconut, oil palm, sisal hemp, tobacco, tomato, pepper, radish, cucumber, Chinese cabbage, celery, preserved vegetable, oilseed rape, onion, garlic, watermelon, melon, cantaloupe, papaya, apple, orange and peach, tea, wild vegetable, bamboo shoot, hops, pepper, banana, papaya, orchid, bonsai.

[0072] Industrial applicability

[0073] The present application provides a class of isochromene pyridone derivatives. The derivatives described in the present application can regulate the biological activity of agricultural, horticultural and health and forestry plant pests and plant pathogens, and can be used in the fields of agriculture, horticulture, forestry, insecticidal, acaricidal, fungicidal, anti-plant virus, induction of plant disease resistance, and have good economic value and application prospect.

[0074]

[0075]

[0076] Table 2 Antifungal activity of isochromene pyridone derivatives I of the present application (inhibition rate / % of 50 μg / ml)

[0077] No. Compound No. A.s B.c C.a F.g P.p R.s S.s 1 I-1 48 42 33 41 36 61 25 2 I-2 51 56 30 49 43 64 33 3 I-3 30 20 17 33 35 34 23 4 I-4 52 33 36 64 69 64 55 5 I-5 53 51 73 0 55 73 46 6 I-6 57 17 58 21 48 69 53 7 I-7 66 73 43 66 53 71 50 8 I-8 52 89 78 30 66 76 51 9 I-9 13 39 15 31 22 28 3 10 I-10 13 29 21 33 3 24 3 11 I-11 53 51 75 0 62 70 46 12 I-12 48 42 33 41 36 61 25 13 thifluzamide 65 59 82 35 39 85 88

[0078] A.s: Tomato early blight, its Latin name is: Alternaria solani, B.c: Cucumber gray mold, its Latin name is: Botrytis cinerea, C.a: Peanut brown spot, its Latin name is: Cercospora arachidicola, F.g: Fusarium graminearum, P.p: Apple ring spot, its Latin name is: Physalospora piricola, R.s: Rice sheath blight, its Latin name is: Rhizoctonia solani, S.s: Rape sclerotinia, its Latin name is: Sclerotinia sclerotiorum.

Claims

1. The synthetic route and method for isochorene pyridinone derivative I are as follows: in, R 1 Selected from: hydrogen, fluorine, methoxy; R 2 Selected from: hydrogen, methyl, ethyl, isopropyl, phenyl; The specific synthesis steps and procedures are described below: A. Preparation of compound 2: Under inert gas protection and at -78°C, an equimolar amount of n-butyllithium hexane solution was added dropwise to an equimolar amount of o-bromobenzaldehyde imine tetrahydrofuran solution, and the reaction was stirred at low temperature for 30 minutes to prepare the corresponding lithium salt solution. The lithium salt solution was then placed in a carbon monoxide atmosphere at atmospheric pressure and stirred for 1 hour. One equivalent amount of acyl chloride was added, and the reaction was brought to room temperature for 1 hour. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (200-300 mesh) using ethyl acetate / petroleum ether as the eluent to obtain starting material 2. The acyl chloride was selected from acetyl chloride, propionyl chloride, n-butyryl chloride, phenylacetyl chloride, and isovaleryl chloride. B. Preparation of compound 3: At room temperature, 8.0 equivalents of concentrated sulfuric acid were added to a 1 equivalent of tetrahydrofuran solution of intermediate 2, stirred at room temperature for 12 hours, quenched with saturated sodium bicarbonate solution, separated, the aqueous phase was extracted with ethyl acetate, the organic phases were combined and dried with anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography with ethyl acetate / petroleum ether as the eluent to obtain isoindolinone morpholine derivative 3. C. Preparation of Compound I: 1.5 equivalents of acid were added to a toluene solution of 1 equivalent of intermediate 3, heated to 90 degrees Celsius and stirred for 9 hours. The mixture was then quenched with saturated sodium bicarbonate solution. The mixture was separated into liquid and aqueous phases, extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography with ethyl acetate / petroleum ether as the eluent to obtain isocyanene pyridinone derivative I. The acid was selected from concentrated sulfuric acid and trifluoromethanesulfonic acid.

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