A class of isoindolinone and morpholine derivatives, and preparation method and use thereof

Abstract

The present application provides a class of isoindolinone and morpholine derivatives, and a preparation method and use thereof, and particularly relates to a class of derivatives, the chemical structure general formula of which is shown in formula I: The present application discloses the structural general formula, the synthesis method and the use of the above-mentioned compound as a plant activator, an insecticide, a fungicide, an anti-plant virus agent and a plant immune activator, the use thereof in combination with an agriculturally acceptable adjuvant or synergist and with commercial insecticides, fungicides, anti-plant virus agents, miticides and plant immune activators in preventing and treating agricultural, forestry and horticultural plant pests, diseases, virus diseases, and a preparation method.

Description

Technical Field

[0001] The technical solution of this invention belongs to the field of pesticides, specifically relating to isoindoline ketone-morpholine derivatives, their preparation methods, and uses. Background Technology

[0002] Pesticides are important strategic materials related to national stability and economic development. As one of the important means of plant protection, they play an extremely important role in solving the problems of pests, diseases, and weeds, as well as increasing the yield of grain crops. However, with the large-scale use of pesticides, problems such as pesticide resistance, pesticide residues, and environmental pollution have also arisen. Therefore, the creation of new pesticides that are highly efficient, low in toxicity, low in residues, and environmentally friendly has become a top priority in research (Shao Xusheng et al. World Pesticides, 2020, 42(04): 16-24). Therefore, "green ecological pesticides" plant activators, which have the characteristics of broad spectrum, low toxicity, no risk of resistance, delayed and long-lasting effects, and synergistic or enhanced effects when mixed with other fungicides, have become an important direction for the creation of green pesticides.

[0003] Compounds containing the isoindolineone skeleton are very important nitrogen- and oxygen-containing heterocyclic compounds, widely found in pharmaceutical molecules, pesticide molecules, and natural products. Many of these molecules possess excellent biological activities, such as antioxidant, anti-inflammatory, antiviral, anticancer, antibacterial, and enzyme inhibitor properties. Morpholine, also a nitrogen- and oxygen-containing heterocyclic skeleton, is widely found in pharmaceutical and pesticide molecules and has broad application value, such as as an anti-inflammatory drug and a lead molecule for herbicides. Therefore, the synthesis and biological activity studies of compounds containing isoindolineone and morpholine skeletons have received widespread attention from chemists and biochemists, and numerous synthetic methods and property studies have been reported (Ariadni Tzara et al. ChemMedChem, 2020, 15(5): 392-403). However, in these methods for constructing isoindolineone and morpholine derivatives, many substrates are complex, and the synthetic steps are often lengthy and cumbersome. Developing new, simple, and rapid methods for preparing isoindolineone and morpholine compounds, and enriching the molecular skeletons of novel potential drugs, is of great significance in laying a solid foundation for their potential applications. This invention develops a class of isoindolineone and morpholine derivatives and their preparation methods, and discovers that they exhibit good induction of disease resistance activity at low concentrations, making them potential plant activator molecules. Summary of the Invention

[0004] The technical problem to be solved by this invention is to provide a new method for synthesizing a class of isoindoline ketone-morpholine derivatives, to provide methods for measuring the bioactivity of these compounds in regulating agricultural, horticultural, health, and forestry plant pests and pathogens, and to provide applications of these compounds in the fields of agriculture, horticulture, forestry, and health.

[0005] The technical solution adopted by this invention to solve this technical problem is as follows: the general chemical formula of the isoindoline ketone-morpholine derivative having insecticidal, acaricidal, fungicidal, antiviral, and plant disease-inducing activities in agriculture, horticulture, and forestry is shown in Figure I:

[0006]

[0007] Among them, R 1 Selected from: hydrogen, fluorine, methoxy; R 2 Selected from: methyl, ethyl, propyl, phenyl, benzyl, isopentyl, 3-trifluoromethyl-phenyl, 4-methoxyphenyl, 2-furanyl; R 3 Selected from: hydrogen, ethyl, benzo[d][1,2,3]thiadiazole-7-acyl, 3,4-dichloroisothiazol-5-acyl, 4-methyl-1,2,3-thiadiazole-5-acyl.

[0008] The synthetic route of the isoindoline ketone-morpholine derivative I and its intermediates of the present invention is as follows:

[0009]

[0010] The method for synthesizing the isoindoline ketone-morpholine derivative I described in this invention comprises the following steps:

[0011] A. Preparation of compound 2:

[0012] 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. The mixture was stirred at low temperature for 30 minutes to prepare the corresponding lithium salt solution. This 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 mixture was raised to room temperature and reacted for 1 hour. The solvent was removed under reduced pressure. 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, benzoyl chloride, phenylacetyl chloride, isovaleryl chloride, 3-trifluoromethylbenzoyl chloride, 4-methoxybenzoyl chloride, and 2-furanyl chloride.

[0013] B. Preparation of compound Ia:

[0014] At room temperature, 1.0 equivalent of trifluoromethanesulfonic acid (abbreviated as TfOH) was added to a dichloromethane solution of 1 equivalent of intermediate 2. The mixture was stirred at room temperature for 1 minute, quenched with saturated sodium bicarbonate solution, separated, and the aqueous phase was extracted with dichloromethane. 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 Ia.

[0015] C. Preparation of compound Ib:

[0016] At room temperature, 8.0 equivalents of concentrated sulfuric acid were added to a 1 equivalent of tetrahydrofuran solution of intermediate 2, and the mixture was stirred at room temperature for 12 hours. The mixture was then quenched with saturated sodium bicarbonate solution, separated, and 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 give isoindolinone morpholine derivative Ib.

[0017] D. Preparation of compound Ic:

[0018] At room temperature, 1 equivalent of carboxylic acid, 1.5 equivalents of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, and 0.2 equivalents of 4-dimethylaminopyridine were added to a dichloromethane solution of 1 equivalent of compound Ib. The mixture was stirred at room temperature for 12 hours, quenched with saturated sodium bicarbonate solution, and separated. The aqueous phase was 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 (200-300 mesh) using ethyl acetate / petroleum ether as the eluent to give isoindolinone-morpholine derivative Ic. The carboxylic acid was selected from benzo[d][1,2,3]thiadiazole-7-carboxylic acid, 3,4-dichloroisothiazol-5-carboxylic acid, and 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.

[0019] E. Uses of isoindoline ketone-morpholine derivative I:

[0020] This invention provides the use of the isoindoline ketone-morpholine derivative I in the preparation of fungicides.

[0021] This invention provides the use of the isoindoline ketone-morpholine derivative I in the preparation of plant immune activators.

[0022] This invention provides the use of the isoindoline ketone-morpholine derivative I in the preparation of an anti-tobacco mosaic virus agent.

[0023] This invention provides the use of the isoindoline ketone-morpholine derivative I in the preparation of a plant activator for inducing tobacco resistance to tobacco mosaic virus.

[0024] This invention provides the use of the isoindoline ketone-morpholine derivative I in the control of pests in agricultural, forestry, and horticultural plants.

[0025] F. Compositions containing isoindolinone-morpholine derivative I and their uses:

[0026] The isoindoline ketone-morpholine derivative I is applied in conjunction with agricultural chemicals; the agricultural chemicals are selected from one or more of the following: insecticides, fungicides, antiviral agents for plants, acaricides, and plant immune activators.

[0027] The isoindoline ketone-morpholine derivative I, combined with any one or two of the insecticides, forms an insecticidal composition for the prevention and control of pests in agricultural, forestry, and horticultural plants.

[0028] 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 , bis(phenylfluorouron), flufenoxuron, fenflurfen, bis(triflufenoxuron), furazolidone, chlorfenapyr, methoxyfenozide, cyclone dichlorvos, dichlorvos, quinalphos, pyridazin, leafhopper powder, carbaryl, pirimicarb, methamidophos, isoprocarb, pyridaben, methyl parathion, methyl parathion, bromopropylate, thiamethoxam, azoxystrobin, pyridaben, tetradifon, propargite, bufenozide, pymetrozine, spirodiclofen, spirotetramat, triazophos, thiamethoxam, chlorfenapyr, tetrachlorfenapyr, flufenoxuron, flufenoxuron, cyanfenoxuron, butenylflufenoxuron, azoxystrobin, bromopropylate, pyrazinazole, etoxazole, pyridaben, pyridaben, pyriproxyfen, emamectin, pendimethalin;

[0029] The mass percentage of the isoindoline morpholine derivative I in the insecticidal composition is 1%-90%; preferably, the ratio of the isoindoline morpholine derivative I to the insecticide is 1%:99% to 99%:1% by mass percentage.

[0030] 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;

[0031] 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;

[0032] 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.

[0033] The isoindoline ketone-morpholine derivative I, combined with any one or two of the fungicides, forms a fungicidal composition for the prevention and control of diseases in agricultural, forestry, and horticultural plants.

[0034] 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, fenpyroximKiller carbendazim, thiocyanate, dichloropropene, dichloroisocyanuric acid, allylisothiazol;

[0035] The total mass percentage of the isoindoline morpholine derivative I in the bactericidal composition is 1%-90%; the ratio of the isoindoline morpholine derivative I to the bactericide is 1%:99% to 99%:1% by mass percentage.

[0036] 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, 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;

[0037] The plant diseases controlled by the bactericidal composition are selected from: rice seedling cottony 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.

[0038] The plants suitable for use in the bactericidal composition are 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.

[0039] The isoindoline ketone-morpholine derivative I, combined with any one or two of the antiviral agents, forms an antiviral composition for the prevention and control of viral diseases in agricultural, forestry, and horticultural plants.

[0040] The antiviral agents are selected from: benzothiadiazole, thiamethoxam, isothiazine DL-β-aminobutyric acid, 2,6-dichloroisonicotinic acid, N-cyanomethyl-2-chloroisonicotinamide, allylisothiazide, ribavirin, antofen, ningnanmycin, methiazolinone or salicylic acid, pyrimethanil, dichloroisonicotinic acid, allylisothiazide, jinggangmycin, and morpholine guanidine hydrochloride.

[0041] The total mass percentage of the isoindoline morpholine derivative I in the antiviral composition is 1%-90%; preferably, the ratio of the isoindoline morpholine derivative I to the anti-plant virus agent is 1%:99% to 99%:1% by mass percentage.

[0042] The dosage forms of the antiviral composition are 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.

[0043] The antiviral composition controls viral diseases selected from: rice dwarf virus, yellow dwarf virus, stripe leaf blight, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, maize dwarf mosaic virus, cauliflower mosaic virus, citrus virus, Cymbidium faberi leaf virus, and Cymbidium faberi ringspot virus.

[0044] The antiviral composition is used to prevent and control diseases from 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.

[0045] The isoindoline ketone-morpholine derivative I, combined with any one or two of the acaricides, forms an acaricide composition for the prevention and control of mite infestations in agricultural, forestry, and horticultural plants.

[0046] 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;

[0047] The total mass percentage of the isoindoline morpholine derivative I in the acaricide composition is 1%-90%; the ratio of the isoindoline morpholine derivative I to the acaricide is 1%:99% to 99%:1% by mass percentage.

[0048] 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;

[0049] 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.

[0050] 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.

[0051] The isoindoline ketone-morpholine derivative I, combined with any one or two of the plant immune activators, forms a plant immune activator composition for the prevention and control of diseases in agricultural, forestry, and horticultural plants.

[0052] The plant activator agents are selected from: benzothiadiazole, isothiazamine, S-inducer, oligosaccharide chain protein, amino oligosaccharide, lentinan, fluoxetine activated ester, oligosaccharide, chitosan, flufenoxuron, DL-β-aminobutyric acid, 2,6-dichloroisonicotinic acid, N-cyanomethyl-2-chloroisonicotinamide, allylisothiazide, methylthiazolinone, crotonin, salicylic acid, jinggangmycin, hypersensitive protein, laminarin, pyraclostrobin, and allylisothiazide.

[0053] The total mass percentage of the isoindoline morpholine derivative I in the plant immune activator composition is 1%-90%; preferably, the ratio of the isoindoline morpholine derivative I to the plant immune activator is 1%:99% to 99%:1% by mass percentage.

[0054] The dosage forms of the plant immune activator composition are 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;

[0055] The diseases controlled by the anti-plant immune activator composition are selected from: rice seedling cottony rot, tomato root rot, potato late blight, tobacco black shank, millet powdery mildew, grape downy mildew, lettuce downy mildew, cucumber downy mildew, cucumber anthracnose, rice dwarf disease, yellow dwarf disease, stripe leaf blight, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, corn dwarf mosaic, cauliflower mosaic virus, citrus virus, Cymbidium faberi leaf virus, and Cymbidium faberi ringspot virus.

[0056] The plant immune activator composition used for prevention and control includes the following plants: 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, scallion, garlic, watermelon, cantaloupe, honeydew melon, papaya, apple, citrus and peach trees, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, and bonsai.

[0057] The bioactivity of the isoindoline ketone-morpholine derivative I described in this invention was determined as follows:

[0058] Determination of the bactericidal activity of the isoindoline ketone-morpholine derivative I of the present invention:

[0059] The bactericidal or bacteriostatic activity of the isoindoline ketone-morpholine derivative I of this invention was determined by the cell growth rate assay. The specific steps are as follows: 1.8 mg of sample was dissolved in 2 drops of dimethyl sulfoxide, then diluted to 500 μg / mL with an aqueous solution containing a certain amount of Tween 20 emulsifier. Under aseptic conditions, 1 mL of the test reagent was placed in each petri dish, and 9 mL of PDA medium was added to each dish. After shaking well, a 50 μg / mL drug-containing plate was prepared. A plate with 1 mL of sterile water added was used as a blank control. A 4 mm diameter plate was used. Mycelial discs were cut along the outer edge of the hyphae using a punch and transferred to drug-containing plates, arranged in an equilateral triangle. Each treatment was repeated three times. The petri dishes were incubated in a constant temperature incubator at 24±1 degrees Celsius. After the diameter of the control colonies expanded to 2-3 cm, the diameter of the expanded mycelial discs for each treatment was measured, and the average value was calculated. The relative inhibition rate was calculated by comparing the average value with the blank control. The tested fungal species are most of the typical plant pathogens that actually occur in the field in my country's agricultural production. Their codes and names are as follows: As: Tomato early blight pathogen, its Latin name is Alternaria. solani, Bc: Botrytis cinerea, the causal agent of gray mold in cucumber; Ca: Cercospora arachidicola, the causal agent of brown spot in peanut; Fg: Fusarium graminearum, the causal agent of Fusarium graminearum; Pp: Physalospora piricola, the causal agent of ring rot in apple; Rc: Rhizoctonia cerealis, the causal agent of sclerotium rot in cereal; Ss: Sclerotinia sclerotiorum, the causal agent of sclerotium rot in rapeseed.

[0060] Assay of the in vivo immunoinduction activity of the isoindoline ketone morpholine derivative I of the present invention:

[0061] The immunoinducing activity of the isoindoline ketone-morpholine derivative I against *Peronobacter thaliana* of this invention was determined by spore counting. The specific steps were as follows: 1.8 mg of sample was dissolved in 2 drops of N,N-dimethylformamide, and then diluted to 100 μmol / L with an aqueous solution containing a certain amount of Tween 20 emulsifier. *Arabidopsis thaliana* (Col-O) seeds were sown in the soil of a growth chamber and grown for 2 weeks under a 16-hour light (22°C) / 8-hour dark (20°C) cycle. Twenty *Arabidopsis thaliana* seedlings were then sprayed with 1 ml of the 100 μmol / L concentration of the agent; 0.2% DMF (N,N-dimethylformamide) without the test compound was used as a control. After 24 hours of chemical treatment, the isolated seedlings containing *Arabidopsis thaliana* were collected and vortexed in sterile water. The number of spores in the water was then determined using a hemocytometer, and the solution was diluted to 5 × 10⁻⁶. 4 A spore concentration of *Arabidopsis thaliana* spore solution (spores / mL) was inoculated onto *Arabidopsis thaliana* seedlings. After inoculation, the seedlings were placed in an incubator at 18°C ​​and 80-100% humidity and observed for 7 days. To determine the spore count, the collected seedlings were vortexed in sterile water and then counted using a hemocytometer. The relative inhibition rate was calculated by comparing the results with the control. Each treatment consisted of three replicates.

[0062] The beneficial effects of this invention are: a novel isoindoline ketone-morpholine derivative I was synthesized, and the antibacterial activity of isoindoline ketone-morpholine derivative I was screened.

[0063] This invention provides more specific examples of the synthesis, bioactivity, and application of isoindolinetone-containing morpholine derivative I through specific preparation and bioactivity assays. These examples are for illustrative purposes only and are not intended to limit the invention. In particular, the bioactivity is merely illustrative and not intended to limit this patent. Specific implementation methods are as follows:

[0064] Example 1: Preparation of compound Ia-1:

[0065] (1) Add 4.8 g (16.0 mmol) of 1-(2-bromophenyl)-N-(2,2-diethoxyethyl)methylimine and 200 mL of tetrahydrofuran to a 500 mL Schlenk flask. Under inert gas protection and at -78 °C, add 10 mL (16.0 mmol) of n-butyllithium hexane solution to the tetrahydrofuran solution dropwise. Stir the reaction at low temperature for 30 minutes to obtain the corresponding lithium salt solution. Then place the lithium salt solution in a container... The reaction was stirred for 1 hour under a carbon monoxide atmosphere at normal pressure. Propionyl chloride (1.36 mL, 16.0 mmol) 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 with ethyl acetate / petroleum ether as the eluent at a ratio of 1:3 (v / v). 2.02 g of the starting material, a yellow oily substance 2-(2,2-diethoxyethyl)-3-propionylisoindoline-1-one, was obtained, with a yield of 41%.

[0066] (2) In a 100 mL single-necked round-bottom flask, 2-(2,2-diethoxyethyl)-3-propionylisoindoline-1-one (664 mg, 2.17 mmol) was dissolved in 35 mL of dichloromethane solution. Trifluoromethanesulfonic acid (0.19 mL, 2.17 mmol) was added dropwise. After stirring at room temperature for 1 minute, 20 mL of saturated sodium bicarbonate solution was added to quench the reaction. The aqueous layer was separated and extracted twice with 20 mL of dichloromethane. The combined organic layers were washed once with 30 mL of saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (200–300 mesh) using ethyl acetate / petroleum ether as eluent (2:1, v / v) to give 400 mg of a yellow oil, Ia-1, in 71% yield.

[0067] Example 2: Preparation of compound Ib-1:

[0068] In a 500 mL single-necked round-bottom flask, 3.5 g (11.5 mmol) of 2-(2,2-diethoxyethyl)-3-propionylisoindoline-1-one was dissolved in 300 mL of dichloromethane solution. Concentrated sulfuric acid (5.0 mL, 91.7 mmol) was added dropwise. After stirring at room temperature for 12 hours, the mixture was quenched with 300 mL of saturated sodium bicarbonate solution. The aqueous layer was separated and extracted twice with 150 mL of ethyl acetate. The combined organic layers were washed once with 200 mL of saturated sodium chloride solution and dried over anhydrous sodium sulfate. 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 eluent (3:1, v / v) to give 1.73 g of a yellow oil, Ib-1, in 65% yield.

[0069] Example 3: Preparation of compound Ic-1:

[0070] In a 100 mL single-necked round-bottom flask, 72 mg (0.5 mmol) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 1,5N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (144 mg, 0.75 mmol), and 12 mg (0.1 mmol) of 4-dimethylaminopyridine were added to 20 mL of a dichloromethane solution containing compound Ib-6 (140 mg, 0.5 mmol). The mixture was stirred at room temperature for 12 hours, quenched with 10 mL of saturated sodium bicarbonate solution, and the aqueous layer was separated and extracted twice with 10 mL of ethyl acetate. The combined organic layers were washed once with 20 mL of saturated sodium chloride solution and dried over anhydrous sodium sulfate. 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 (3:1, v / v) to give 100 mg of a yellow oil, Ic-1, in 49% yield.

[0071] Example 4: Results of antibacterial activity assay of isoindoline ketone morpholine derivative I of the present invention:

[0072] The common plant pathogenic fungi tested in this invention are coded and named as follows: As: *Alternaria solani*, the Latin name for early blight of tomato; Bc: *Botrytis cinerea*, the Latin name for gray mold of cucumber; Ca: *Cercospora arachidicola*, the Latin name for brown spot of peanut; Fg: *Fusarium graminearum*, the Latin name for Fusarium graminearum; Pp: *Physalospora piricola*, the Latin name for ring rot of apple; Rs: *Rhizoctonia solani*, the Latin name for sheath blight of rice; Ss: *Sclerotinia sclerotiorum*, the Latin name for sclerotinia sclerotiorum, the Latin name for sclerotinia sclerotiorum. These species are highly representative and can represent most of the pathogenic fungi occurring in the field during agricultural production.

[0073] The results of the cell growth rate assay are shown in Table 2. Table 2 shows that the compounds synthesized in this invention have certain fungicidal activity at 50 μg / mL. The commercial plant activator BTH and thifluzamide with an amide structure were used as positive controls to determine the bioactivity of the new compounds. The results showed that compounds Ia-8 and Ia-11 had fungicidal activity above 50% against *Pseudomonas aeruginosa*, the causal agent of early blight of tomato; and compounds Ia-7, Ia-8, Ia-11, Ib-6, Ib-7, Ib-8, Ic-1, Ic-2, and Ic-3 had fungicidal activity against *Botrytis cinerea*, the causal agent of gray mold of cucumber. The inhibitory activity of all compounds was above 60%, superior to the control drug thifluzamide; among them, compounds Ic-1 and Ic-3 achieved an inhibition rate of 80%; for peanut brown spot fungus, compounds Ia-7 and Ia-11 showed fungicidal activity above 60%; for Fusarium graminearum causal agent, compound Ia-8 showed fungicidal activity above 50%, higher than the control drug thifluzamide; for apple ring rot fungus, compounds Ia-7 and Ia-11 showed fungicidal activity above 50%, higher than the control drug thifluzamide; for rice sheath blight fungus, compounds Ia-7 and Ia-11 showed fungicidal activity above 50%. Compounds Ia-7 and Ia-11 exhibited relatively broad-spectrum fungicidal activity.

[0074] Example 5: Assay of the in vivo immunoinduction activity of the isoindolinone nemorpholine derivative I of the present invention:

[0075] The *Arabidopsis thaliana* fungus used in the in vivo immunogenicity testing of this invention was *Arabidopsis thaliana*. The test results are shown in Table 3. Table 3 shows that at 100 μmol / L, all Ic compounds synthesized in this invention exhibited certain immunogenic resistance activity. Among them, Ic-2 and Ic-3 showed 100% immunogenic resistance activity against *Arabidopsis thaliana*, comparable to the commercial plant activator BTH. At 5 μmol / L, compound Ic-2 showed 97% immunogenic resistance activity against *Arabidopsis thaliana*, superior to the 92% of the commercial control drug BTH. These results indicate that the compounds possess excellent immunogenic resistance activity.

[0076] Example 6: Application of the isoindoline ketone-morpholine derivative I of the present invention in the preparation of pesticide compositions:

[0077] The present invention provides a pesticide composition for preparing a pesticide containing isoindoline ketone morpholine derivative I, wherein the composition contains the present invention's isoindoline ketone morpholine derivative I and its intermediates as active ingredients, the active ingredients having a mass percentage content of 0.1% to 99.9%, solid or liquid adjuvants having a mass percentage content of 99.9% to 0.1%, and optionally a surfactant having a mass percentage content of 0 to 50%.

[0078] Example 7: Application of the isoindoline ketone-morpholine derivative I of the present invention in the preparation of pesticide compound compositions:

[0079] The isoindoline morpholine derivative I and its intermediates of the present invention can be compounded with other commercial pesticides, namely insecticides, acaricides, fungicides, antiviral agents or plant activators, to prepare pesticide compound compositions. These compound compositions contain the isoindoline morpholine derivative I and its intermediates of the present invention and commercial pesticides, namely insecticides, acaricides, fungicides, antiviral agents or plant activators, as active ingredients. The ratio of the isoindoline morpholine derivative I and its intermediates to other commercial pesticides, namely insecticides, acaricides, fungicides, antiviral agents or plant activators, is 1%:99% to 99%:1% by mass. The mass percentage content of the active ingredient is 0.1% to 99.9%, the mass percentage content of solid or liquid adjuvants is 99.9% to 0.1%, and the mass percentage content of surfactant is optionally 0% to 50%.

[0080] Example 8: Application of the combination of the isoindoline ketone-morpholine derivative I of the present invention with an insecticide in the control of agricultural, forestry, and horticultural plant pests:

[0081] The present invention relates to an insecticidal composition formed by combining isoindoline ketone-morpholine derivative I with any one or two commercial insecticides for the control of agricultural, forestry, and horticultural plant pests. The commercial insecticides are selected from: imidacloprid, difenoconazole, acetamiprid, emamectin benzoate, miconazole, abamectin, spinosad, cypermethrin, deltamethrin, deltamethrin, deltamethrin, cypermethrin, β-cypermethrin, λ-cypermethrin, dichlorvos, permethrin, allethrin, bifenthrin, permethrin, fenpropathrin, flufenoxuron, and deltamethrin. Imidacloprid, acetamiprid, chlorpyrifos, thiamethoxam, thiamethoxam, dinotefuran, conidine, datnam, diflubenzuron, diflubenzuron, flufenoxuron, flufenoxuron, acetamiprid, lufenuron, tebufenozide, flufenoxuron, polyfluorourea, flufenoxuron, difenourea, flufenoxuron, fenflurfen, fenflurfen, chlorfenapyr, methoxyfenozide, cyclone dichlorvos, dichlorvos, quinalphos, pyridazin, leafhopper powder, carbaryl, pirimicarb, fenpropathrin, isoprocarb, fenitrothion, sec-butylcarbide, leaf spray, carbaryl, fenitrothion, bromopropylate, thiamethoxam, azoxystrobin, pyridaben, tetradifon, propargite, dicofol Etherurea, pymetrozine, spirodiclofen, spirotetramat, spirotetramat ethyl ester, triazophos, thiamethoxam, cartap, chlorantraniliprole, tetrachlorantraniliprole, flufenoxuron, flufenoxuron, cyanantraniliprole, butenpyram, acetamiprid, bromfenoxuron, pyrazinone, etoxazole, pyridoxamine, pyridoxone, pyriproxyfen, emamectin, pendimethalin; the isoindoline morpholine derivative I of the present invention has a mass percentage content of 1%-90% in the insecticidal composition, and the ratio of the isoindoline morpholine derivative I of the present invention to the aforementioned commercial insecticides is 1%:99% to 99%:1% by mass percentage; the insecticidal composition is processed... The formulations are 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, and vapor release agents;The insecticidal composition is suitable for the following plant pests: 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 leafhopper. Planthoppers, gray planthoppers, sugarcane flat-horned planthoppers, cotton aphids, wheat two-pronged aphids, wheat long-tubed aphids, peach aphids, sorghum aphids, radish aphids, 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 flower bug, tiny flower bug, needle-edged bug, rice spider-edged bug, rice brown bug, rice black bug, rice green bug, green mirid bug, alfalfa mirid bug, 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, rice leaf roller The following are listed: Rice leaf roller, cotton leaf roller, peach borer, armyworm, beet armyworm, rice stem borer, cotton bollworm, beet armyworm, large stem borer, cotton bollworm, *Gnaphalium affine*, 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 ramie butterfly, ramie yellow ramie butterfly. Butterfly, Bean Fern, Golden Ground Beetle, Wrinkled-Sheath Ground Beetle, Wheat Ear Ground Beetle, Threadworm, Fine-breasted Threadworm, Grain-spotted Ground Beetle, Black Ground 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-gilled Scarab Beetle, Mulberry Longhorn Beetle, Star Longhorn Beetle, Orange Brown Longhorn Beetle, Peach Red-necked Longhorn Beetle, Large Ape Leaf Beetle, Small Leaf beetle, cucumber beetle, yellow-striped flea beetle, bean weevil, pea weevil, broad bean weevil, corn weevil, rice weevil, wheat leaf beetle, pear fruit wasp, yellow-banded ichneumon wasp, armyworm white-spotted ichneumon wasp, larval ichneumon wasp, cotton bollworm toothed ichneumon wasp, larval black-spotted wart ichneumon wasp, mosquito, fly, horsefly, wheat red midge, wheat yellow midge, rice gall midge, citrus fruit fly, melon fruit fly, wheat leaf miner, American serpentine leafminer Flies, including black leafminer flies, wheat stem flies, seed flies, onion flies, turnip flies, umbrella-shaped leafminer flies, corn borers, and armyworms; the insecticidal composition is suitable for 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.

[0082] Example 9: Application of the combination of the isoindoline ketone-morpholine derivative I of the present invention with a fungicide in the prevention and control of diseases in agricultural, forestry, and horticultural plants:

[0083] The present invention relates to a fungicidal composition formed by combining isoindoline ketone-morpholine derivative I with any one or two commercial fungicides for the prevention and control of diseases in agricultural, forestry, and horticultural plants. The commercial fungicides are selected from: benzothiadiazole, thiamethoxam, methomyl, isothiazamide, ribavirin, anthraquinone, ningnanmycin or salicylic acid, cymoxanil, thiram, 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, cycloflufenoxam, cyclopyridamole, cyproconazole, silthiamethoxam, carbendazim, oxychloride, methyl thiophanate, methyl thiophanate, thiabendazim, thiabendazim, silthiabendazim, carbendazim, oxychloride, carbendazim, thia ... Furazolidone, cymoxanil, fluopyram, furazolidone, thifluzamide, cyproconazole, pyraclostrobin, pyraclostrobin, bifenazamide, fluopyram, fluoxastrobin, fluoxastrobin, fluoxastrobin aniline, benzyl-fluoroquinolones, isopyram, fluoxastrobin hydroxylamine, flufenoxuron, fluoxastrobin, diyrylamide, benzyl-fluoroquinolones, ethoxysulfuron, iprodione, pyraclostrobin, ether-based fungicides Amine, flupyraclostrobin, azoxystrobin, fenoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, tebuconazole, oxadiazon, tebuconazole, cyproconazole, difenoconazole, tebuconazole, tebuconazole, flutriafol, cyproconazole, fluquinazole, flusilazole, fenbendazole, hexaconazole, imidacloprid, tebuconazole, cyproconazole, tebuconazole, propiconazole, prothioconazole Azoxystrobin, silfluthrin, tebuconazole, tetraflufenazole, triazole, tebuconazole, bifenthrin, thiamethoxam, imazalil, pyraclostrobin, prochloraz, fluopyram, cyazofamid, imazalil, oxadiazon, isoprothiolane, oxadiazon, pyraclostrobin, oxadiazon, thiamethoxam, terbufos, octothiamethoxam, benzylthiocyanate, dodecyl morpholine, butyl morpholine, tridemorpholine, [unclear text - possibly a continuation of the previous sentence] Flufenoxam, fluazinam, fluazinam, pyridaben, cyclopyridamole, fluazinam, pyridaben, pyrimethanil, thifluzamide, pyrimethanil, chlorpyrifos, fluazinam, abamectin, anthraquinone, ethoxyquinoline, hydroxyquinoline, propoxyquinoline, phenoxyquinoline, ethoxycarb, isoprothiolane, benomyl, cymoxanil, sulfadiazine, difenoconazole, isoprothiolane ... Pyraclostrobin, 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 the isoindoline ketone-morpholine derivative I in the bactericidal composition of the present invention is 1%-90%, and the mass percentage of the isoindoline ketone-morpholine derivative I of the present invention to the aforementioned commercial bactericide 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, and solid / solid mixtures. The fungicidal composition includes agents, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated colloids, pouring 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, and 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, scallion, garlic, watermelon, cantaloupe, honeydew melon, papaya, apple, citrus and peach trees, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, bonsai.

[0084] Example 10: Application of the combination of the isoindoline ketone-morpholine derivative I of the present invention with an antiviral agent in the prevention and control of viral diseases in agricultural, forestry, and horticultural plants:

[0085] The isoindoline ketone-morpholine derivative I of the present invention is combined with any one or two commercial antiviral agents to form an antiviral composition for the prevention and control of viral diseases in agricultural, forestry, and horticultural plants. The commercial antiviral agents are selected from: benzothiadiazole, thiamethoxam, isothiazamide, ribavirin, antofenfen, ningnanmycin, methamidophos or salicylic acid, pyrimethanil, dichloroisonicotinic acid, allylisothiazide, jinggangmycin, and morpholine guanidine hydrochloride. The total mass percentage of the isoindoline ketone-morpholine derivative I in the antiviral composition of the present invention is 1%-90%. The ratio of the known isoindoline ketone-morpholine derivative I to the aforementioned commercial antiviral agent is 1%:99% to 99%:1% by mass percentage; the formulation of the antiviral 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, and aerosols. Solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated colloids, pouring agents, seed coating agents, coating agents, film-forming oils, ultra-low volume liquids, vapor release agents; the viral diseases controlled by the antiviral composition are selected from: rice dwarf virus, yellow dwarf virus, rice stripe leaf blight, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, maize dwarf mosaic virus, cauliflower mosaic virus, citrus virus, Cymbidium faberi leaf virus, and Cymbidium ringspot virus; the antiviral composition is used to control... The plants selected are: 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 tuber, beet, rapeseed, scallion, garlic, watermelon, cantaloupe, honeydew melon, papaya, apple, citrus and peach trees, tea, wild vegetables, bamboo shoots, hops, pepper, banana, papaya, orchid, and bonsai.

[0086] Example 11: Application of the combination of the isoindoline ketone-morpholine derivative I of the present invention with an acaricide in the control of mite pests in agricultural, forestry, and horticultural plants:

[0087] The present invention relates to an isoindoline ketone-morpholine derivative I combined with any one or two commercial acaricides to form an acaricide composition for controlling mite pests in agricultural, forestry, and horticultural plants. The commercial acaricides are selected from: dichlorvos, heptamethrin, cypermethrin, dibromophos, pyrimiphos, chlorpyrifos, ethion, chlorfenapyr, fenpropathrin, methyl pyrimiphos, quinalphos, abamectin, acephate, chlorpyrifos, chlorpyrifos, chlorfenapyr, bifenthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, flufenoxuron, deltamethrin, bifenazate, fenthion, methyl chlorpyrifos, ... The acaricide composition contains the following ingredients: abamectin, fenvalerate, flufenoxuron, flufenoxuron, liuyangmycin, chlorfenapyr, thuringin, dicofol, liuyangmycin, avermectin, doramectin, eprinoxuron, ivermectin, selamectin, moxibustion, pyrethroid, nicotine, matrine, azadirachtin, rotenone, pyridaben, pyridaben, azoxystrobin, tetradifon, propargite, thiamethoxam, spirodiclofen, pyrimethanil, dicofol, clopyralid, pyridaben; the total mass percentage of the isoindoline morpholine derivative I in the acaricide composition is 1%-90%, and the ratio of the isoindoline morpholine derivative I to the commercial acaricide is 1%:99% to 99%:1% by mass percentage; the formulation of the acaricide 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, thermal 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, smearing agents, film-forming oils, ultra-low volume liquids, vapor release agents; the mites controlled by the acaricide composition are selected from: mites selected from Tetranychidae, Amanita fulvidae, Fusarium moniliformes, and Gall mites. The acaricide composition is used to control harmful mites belonging to the genera *Tetranychus*, *Tetranychus*, and *Gallaria*, which are global agricultural, forestry, horticultural, and sanitary pests. The plants used for control are 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.

[0088] Example 12: Application of the combination of the isoindoline ketone-morpholine derivative I of the present invention with a plant immune activator in the prevention and control of viral diseases in agricultural, forestry, and horticultural plants:

[0089] The present invention relates to a plant immune-activating composition formed by combining isoindoline ketone-morpholine derivative I with any one or two commercial plant immune activators for the prevention and control of pathogenic and viral diseases of agricultural, forestry, and horticultural plants. The commercial plant immune-activating agents are selected from: benzothiadiazole, isothiazamine, S-inducer, oligosaccharide chain protein, amino oligosaccharide, lentinan, fluoxetine activated ester, oligosaccharide, chitosan, flufenoxuron, DL-β-aminobutyric acid, 2,6-dichloroisonicotinic acid, N-cyanomethyl-2-chloroisonicotinamide, allylisothiazide, methylthiazolinone, crotonyl thiamethoxam, salicylic acid, jinggangmycin, hypersensitive protein, laminarin, pyraclostrobin, and allylisothiazide. The total mass percentage of the isoindoline ketone-morpholine derivative I in the plant immune activator composition is 1%-90%, and the ratio of the isoindoline ketone-morpholine derivative I to the aforementioned commercial plant immune activator is 1%:99% to 99%:1% by mass percentage; the dosage form of the plant immune activator 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 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, vaporizers, and oils. Ointments, hot mists, cold mists, aerosols, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated colloids, pouring agents, seed coating agents, smearing agents, film-forming oils, ultra-low volume liquids, and vapor release agents; the plant immune-activating composition controls diseases 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, cucumber anthracnose, rice dwarf virus, yellow dwarf virus, rice stripe leaf blight, tomato fern leaf virus, pepper mosaic virus, tobacco vein necrosis virus, corn dwarf mosaic virus, and cauliflower mosaic virus. Citrus virus diseases, Cymbidium leaf virus, Cymbidium ringspot virus; the plants used for prevention and control of the plant immune activation composition are 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, bonsai.

[0090] Industrial applicability

[0091] This invention provides a class of isoindoline ketone-morpholine derivatives. These derivatives can regulate the biological activity of agricultural, horticultural, sanitary, and forestry plant pests and pathogens, and can be used in agriculture, horticulture, and forestry for insecticidal, acaricidal, bactericidal, antiviral, and disease-inducing purposes, exhibiting good economic value and application prospects.

[0092]

[0093]

[0094]

[0095]

[0096] Table 2. Antibacterial activity of the isoindoline ketone-morpholine derivative I of the present invention (inhibition rate / %) at 50 μg / mL

[0097] Serial Number Compound numbering As Bc Ca Fg Pp Rs Ss 1 Ia-1 19 29 13 8 30 22 12 2 Ia-2 13 24 14 0 25 16 2 3 Ia-3 7 9 0 0 12 0 1 4 Ia-4 5 34 15 0 27 12 7 5 Ia-5 23 37 36 0 24 29 16 6 Ia-6 25 47 33 20 27 25 22 7 Ia-7 55 74 66 42 52 57 48 8 Ia-8 34 63 35 55 39 48 35 9 Ia-9 10 22 20 0 22 13 0 10 Ia-10 17 20 21 5 18 22 11 11 Ia-11 57 72 70 40 65 67 45 12 Ib-1 17 33 23 0 29 2 4 13 Ib-2 19 30 18 0 28 10 5 14 Ib-3 16 16 14 27 28 12 8 15 Ib-4 9 11 14 19 22 10 13 16 Ib-5 28 38 27 0 28 49 9 17 Ib-6 23 70 23 0 29 25 24 18 Ib-7 11 63 15 0 15 18 14 19 Ib-8 20 70 31 1 30 36 30 20 Ib-9 22 29 15 0 19 27 2 21 Ib-10 18 32 15 31 33 27 10 22 Ib-11 19 42 23 0 27 34 12 23 Ic-1 25 82 15 17 16 25 30 24 Ic-2 23 60 18 13 15 23 16 25 Ic-3 19 80 20 24 22 35 25 26 BTH 65 14 18 12 19 74 5 27 Thifluzamide 65 59 82 35 39 85 88

[0098] As: Alternaria solani, the causal agent of early blight in tomatoes; Bc: Botrytis cinerea, the causal agent of gray mold in cucumbers; Ca: Cercospora arachidicola, the causal agent of brown spot in peanuts; Fg: Fusarium graminearum, the causal agent of Fusarium graminearum in cereals; Pp: Physalospora piricola, the causal agent of ring rot in apples; Rs: Rhizoctonia solani, the causal agent of sheath blight in rice; Ss: Sclerotinia sclerotiorum, the causal agent of sclerotinia in rapeseed.

[0099] Table 3. In vivo immunogenicity induction activity (inhibition rate / %) of the isoindoline ketone-morpholine derivative I of the present invention against Arabidopsis thaliana perennialis.

[0100]

Claims

1. A class of derivatives containing isoindolinetone morpholine, characterized in that... The structure containing both isoindolinone and morpholine has the general structural formula shown in Formula I: I： Among them, R 1 Selected from: hydrogen, fluorine, methoxy; R 2 Selected from: methyl, ethyl, propyl, phenyl, benzyl, isopentyl, 3-trifluoromethyl-phenyl, 4-methoxyphenyl, 2-furanyl; R 3 Selected from: hydrogen, ethyl, benzo[d][1,2,3]thiadiazole-7-acyl, 3,4-dichloroisothiazol-5-acyl, 4-methyl-1,2,3-thiadiazole-5-acyl.

2. The specific synthetic method of the isoindoline ketone-morpholine derivative I according to claim 1 is as follows: The substituent R 1 R 2 The definition is as described in claim 1, R 4 Selected from: benzo[d][1,2,3]thiadiazole-7-yl, 3,4-dichloroisothiazol-5-yl, 4-methyl-1,2,3-thiadiazole-5-yl; The specific synthesis method consists of the following steps: 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 obtain 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, benzoyl chloride, phenylacetyl chloride, isovaleryl chloride, 3-trifluoromethylbenzoyl chloride, 4-methoxybenzoyl chloride, and 2-furancarboxyl chloride. B. Preparation of compound Ia: At room temperature, 1.0 equivalent of trifluoromethanesulfonic acid (TfOH) was added to a dichloromethane solution of 1 equivalent of intermediate 2, stirred at room temperature for 1 minute, quenched with saturated sodium bicarbonate solution, separated, the aqueous phase was extracted with dichloromethane, 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 give isoindolinone morpholine derivative Ia; C. Preparation of compound Ib: At room temperature, 8.0 equivalents of concentrated sulfuric acid were added to a 1 equivalent of tetrahydrofuran solution of intermediate 2, and the mixture was stirred at room temperature for 12 hours. The mixture was then quenched with saturated sodium bicarbonate solution, separated, and the aqueous phase was extracted with ethyl acetate. 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 give isoindolinone morpholine derivative Ib. D. Preparation of compound Ic: At room temperature, 1 equivalent of acid, 1.5 equivalents of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride, and 0.2 equivalents of 4-dimethylaminopyridine were added to a 1 equivalent of compound Ib in dichloromethane solution. The mixture was stirred at room temperature for 12 hours, quenched with saturated sodium bicarbonate solution, separated, and the aqueous phase was extracted with ethyl acetate. 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 (200-300 mesh) using ethyl acetate / petroleum ether as the eluent to obtain isoindolinone-morpholine derivative Ic. The acid was selected from benzo[d][1,2,3]thiadiazole-7-carboxylic acid, 3,4-dichloroisothiazol-5-carboxylic acid, and 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.

3. The use of the isoindoline ketone-morpholine derivative I according to claim 1 in the preparation of agricultural fungicides, wherein the fungus is selected from: early blight pathogen of tomato, gray mold pathogen of cucumber, brown spot pathogen of peanut, Fusarium graminearum, ring rot pathogen of apple, sheath blight pathogen of rice, sclerotinia sclerotium of rapeseed, and downy mildew of Arabidopsis thaliana.

4. The use of the isoindoline ketone-morpholine derivative I according to claim 1 in the preparation of plant immune activators.

5. An agricultural bactericidal composition comprising, as claimed in claim 1, an isoindolinone-morpholine derivative I as an active ingredient, wherein the active ingredient is present in an amount of 0.1% to 99.9% by weight, a solid or liquid adjuvant of 99.9% to 0.1% by weight, and optionally a surfactant of 0 to 25% by weight.

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