An oxadiazole compound and its application

Abstract

The present invention discloses a compound of formula I, wherein Q is selected from Q-1 and Q-2, wherein R 1 ‑R 6 , X, Y and Z are as defined in the description. The compound of the present invention has excellent insecticidal effect and has good application prospects.

Description

Technical Field

[0001] The present invention belongs to the field of agricultural pesticides, and specifically relates to a novel oxadiazole compound pesticide. The present invention also relates to compositions containing these compounds and their use in controlling or preventing plant pests in agriculture or horticulture. Technical Background

[0002] There are prior art reports on the use of oxadiazole compounds as active ingredients in agricultural pesticides or external or parasitic insecticides for animals.

[0003] CN108699066A discloses that the compound of formula (1) has a good insecticidal effect. The compound of formula (1) has the following structure:

[0004]

[0005] CN114641475A discloses that the compound of formula (1) has an insecticidal effect. The compound of formula (1) has the following structure:

[0006]

[0007] In farmland crop production, pests cause significant damage. Developing new agricultural pesticides, particularly those with superior insecticide efficacy and minimal environmental impact, is a key research and development direction. Summary of the Invention

[0008] The present invention provides an oxadiazole compound, its nitrogen oxide, an pesticide-acceptable salt and a composition thereof, which has excellent insecticidal activity and can be used as an insecticide for crops.

[0009] Specifically, the present invention discloses a compound of formula I,

[0010]

[0011] in,

[0012] Q is selected from Q-1 and Q-2,

[0013]

[0014] R 1 is H, C1-C6 alkyl, preferably, R1 is H;

[0015] R 2 is H, C3-C6 cycloalkyl, preferably, R2 is H, cyclopropyl;

[0016] R 3 is H, C1-C6 alkyl, preferably, R3 is H and methyl;

[0017] R 4 and R 5 Each is independently H, C1-C6 alkyl, substituted C3-C6 cycloalkyl, preferably, each is independently selected from H, cyclopropyl substituted cyclopropyl and halogen substituted cyclopropyl;

[0018] R 6 is H, halogen, C1-C6 alkyl or C1-C6 haloalkyl;

[0019] X, Y and Z are each independently O or N or C.

[0020] The present invention also provides a composition comprising the compound of formula I of the present invention.

[0021] Preferably, the above composition comprises the compound of the present invention and at least one auxiliary agent selected from the group consisting of surfactants, solid diluents and liquid diluents.

[0022] Preferably, the compound of formula I or the composition of the present invention is used in controlling plant pests.

[0023] In another aspect, the present invention provides a method for curatively or preventively controlling plant or crop pests, comprising applying the compound of formula I or the composition of the present invention to seeds, plants or plant fruits, or to soil where plants are growing or to be grown. DETAILED DESCRIPTION

[0024] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "including" or its variations such as "comprising" or "including" will be understood to include the stated components or steps, without excluding other material components or steps.

[0025] Furthermore, in order to better illustrate the present invention, numerous specific details are given in the following detailed description.

[0026] Those skilled in the art will appreciate that the present invention can be practiced without certain specific details. In some embodiments, raw materials, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the main purpose of the present invention.

[0027] If the compounds of formula I described herein are capable of forming geometrical isomers, such as E / Z isomers, both the pure isomers and mixtures thereof can be used in the compositions according to the invention.

[0028] If the compounds of formula I described herein have one or more chiral centers and therefore exist as enantiomers or diastereomers, the pure enantiomers, racemates, or diastereomers can be used in the compositions of the present invention.

[0029] When the compounds of the present invention are capable of existing in tautomeric forms, the above and below references to

[0030] The compounds described are to be understood as also comprising the corresponding tautomeric forms, even if these are not explicitly mentioned in each case.

[0031] Any asymmetric atom (eg, carbon, etc.) in the compounds disclosed herein may exist in a racemic or enantiomerically enriched form, such as in the (R)-, (S)-, or (R,S)-configuration.

[0032] If the compounds of the formula I according to the invention have functional groups which can be ionized, they can also be used in the form of their agriculturally acceptable salts or mixtures thereof.

[0033] Suitable are generally salts of cations whose cations do not adversely affect the action of the active compounds ("agriculturally acceptable"). Preferred cations are ions of alkali metals, preferably lithium, sodium and potassium, ions of alkaline earth metals, preferably calcium and magnesium, and ions of transition metals, preferably manganese, copper, zinc and iron.

[0034] Anions useful for acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, and carbonate.

[0035] The present invention C n -C m The subscripts n and m in each case indicate the number of carbon atoms in the group. For example, C1-C6 indicates a group containing 1 to 6 carbon atoms. The alkyl groups appearing in the definitions of substituents may be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, sec-butyl, isobutyl or tert-butyl.

[0036] Halogen is typically fluorine, chlorine, bromine or iodine in the present invention, preferably fluorine, bromine or chlorine. Accordingly, this also applies to halogens combined with other structures, such as haloalkyl. Haloalkyl preferably has a chain length of 1 to 6 carbon atoms, more preferably a chain length of 1 to 4 carbon atoms. Examples of haloalkyl include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, difluorochloromethyl and dichlorofluoromethyl. C3-C6 cycloalkyl represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like, and substituted C3-C6 cycloalkyl refers to substituted by halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl.

[0037] The term "plant propagation material" should be understood as meaning the reproductive parts of a plant, such as seeds that can be used for plant propagation, and plant materials, such as cuttings or tubers, for example potatoes. Examples include seeds (strictly speaking), roots, fruits, tubers, bulbs, rhizomes, and plant parts. Examples also include germinated plants and seedlings to be transplanted after germination or after emergence from the soil. These seedlings can be protected by whole or part immersion treatments before transplanting. Preferably, "plant propagation material" should be understood as meaning a seed.

[0038] The present invention provides a compound represented by formula I,

[0039]

[0040] in,

[0041] Q is selected from Q-1 and Q-2,

[0042]

[0043] R 1 is H, C1-C6 alkyl, preferably, R1 is H;

[0044] R 2 is H, C3-C6 cycloalkyl, preferably, R2 is H and cyclopropyl;

[0045] R 3 is H, C1-C6 alkyl, preferably, R3 is H and methyl;

[0046] R 4 and R 5 Each is independently H, C1-C6 alkyl, substituted C3-C6 cycloalkyl, preferably, each is independently selected from H, cyclopropyl substituted cyclopropyl and halogen substituted cyclopropyl;

[0047] R6 is H, halogen, C1-C6 alkyl or C1-C6 haloalkyl;

[0048] X, Y and Z are each independently O or N or C. Indicates the group attachment position.

[0049] Particularly preferably, the compound of formula I is selected from:

[0050]

[0051] In this specification, if there is any difference between the chemical name and the chemical structure, the structure is the preferred one. Generally, the compounds of the present invention can be prepared by the methods described herein, unless otherwise specified. The following synthetic schemes and examples are provided to further illustrate the present invention.

[0052] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many other compounds of the present invention, and other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of non-exemplified compounds according to the present invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents (in addition to those described herein), or by making some conventional modifications to the reaction conditions. In addition, the reactions disclosed herein or known reaction conditions are also generally applicable to the preparation of other compounds of the present invention.

[0053] Synthesis scheme

[0054]

[0055] Among them, Q, R 1 and R 2 The definition of is as defined in formula I.

[0056] Structural formula I can be synthesized by existing methods. I-01 is used as a raw material, reacted with hydroxylamine hydrochloride, and then reacted with an acyl chloride to cyclize to obtain an oxadiazole ring structure to synthesize compound I. As described by Du HC et al. in Bioconjugate Chem. 2019, 30(5), 1304-1308.

[0057] The present invention also provides a composition comprising the compound of formula I of the present invention and at least one adjuvant selected from the group consisting of surfactants, solid diluents and liquid diluents.

[0058] Application of the compound or composition of the present invention in preventing and controlling plant pests.

[0059] The present invention also provides a method for treating plant propagation material, which comprises applying to the propagation material a composition or formulation containing a compound of the present invention.

[0060] The compounds of the present invention can generally be used as active ingredients of pesticides in compositions or formulations, which usually also include pesticide-acceptable surfactants and carriers. The carriers can be solid carriers or liquid carriers.

[0061] Suitable solid carriers include natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as kaolinite, kaolin, montmorillonite and mica; white carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; ammonium salts, such as ammonium sulfate, hexamethylenediamine and urea, etc.

[0062] Liquid carriers include water and organic solvents. When water is used as the solvent or diluent, organic solvents can also be used as adjuvants or antifreeze additives. Useful liquefied gaseous fillers or carriers are those liquids that are gaseous at standard temperature and standard pressure, such as aerosol propellants, such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide, etc.

[0063] Suitable organic solvents include aromatic hydrocarbons, such as benzene, xylene, toluene, etc.; chlorinated hydrocarbons, such as chlorobenzene, vinyl chloride, chloroform, dichloromethane, etc.; aliphatic hydrocarbons, such as petroleum fractions, cyclohexane, light mineral oil; alcohols, such as isopropyl alcohol, butanol, ethylene glycol, glycerol and cyclohexanol, etc.; and their ethers and esters; ketones, such as acetone, cyclohexanone, dimethylformamide and N-methyl-pyrrolidone, vegetable oils, such as soybean oil, rapeseed oil and cottonseed oil, etc.

[0064] Suitable surfactants (adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and binders) include all common ionic and nonionic substances, for example ethoxylated nonylphenols, polyalkylene glycol ethers of linear or branched alcohols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, reaction products of fatty acid amines with ethylene oxide and / or propylene oxide, and also fatty acid esters, alkylsulfonates, alkyl sulfates, alkyl ether sulfates, alkyl ether phosphates, aryl sulfates, ethoxylated arylalkylphenols (such as tristyrylphenol ethoxylate), and ethoxylated and propoxylated arylalkylphenols, such as sulfated and phosphated arylalkylphenol ethoxylates and -ethoxylates and -propoxylates. Other examples are natural and synthetic water-soluble polymers, such as ligninsulfonates, gelatin, gum arabic, phospholipids, starch, hydrophobically modified starch and cellulose derivatives, in particular cellulose esters and cellulose ethers, as well as polyvinyl alcohol, polyvinyl acetate, polyvinyl pyrrolidone, polyacrylic acid, polymethacrylic acid and copolymers of (meth)acrylic acid and (meth)acrylic esters, as well as copolymers of methacrylic acid and methacrylic esters neutralized with alkali metal hydroxides, and condensates of optionally substituted naphthalenesulfonates with formaldehyde. If one of the active ingredients and / or one of the inert carriers is insoluble in water and application is carried out in water, the presence of a surfactant is essential.

[0065] The agrochemical insecticides of the present invention can be prepared by conventional methods. For example, the active substance is mixed with a liquid solvent and / or a solid carrier, and a surfactant such as an emulsifier, dispersant, stabilizer, or wetting agent is added. Other adjuvants such as adhesives, defoamers, foaming agents, antioxidants, crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet regulators, pigments, neutralizers and buffers, corrosion inhibitors, dyes, flavoring agents, spreading agents, penetration aids, micronutrients, dispersants, thickeners, freezing point depressants, and antimicrobial agents may also be added.

[0066] The agrochemical insecticides of the present invention can be applied in the form of their formulations or use forms prepared therefrom, such as aerosols, capsule suspensions, cold-fogging concentrates, hot-fogging concentrates, encapsulated granules, fine granules, flowable concentrates for seed treatment, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, large granules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, aerosols (under pressure), gas-generating products, foams, pastes, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble and water-dispersible granules or tablets, water-soluble or water-dispersible powders for seed treatment, wettable powders, natural products and synthetic substances impregnated with active substances, and microcapsules in polymers and seed coating materials, as well as ULV (ultra low volume) cold mist and hot mist preparations.

[0067] The formulation of the present invention may also contain other components, such as other fungicides, insecticides, herbicides, plant growth regulators, attractants, acaricides, nematicides, fertilizers, safeners, etc., which can be formulated with liquid fertilizers or solid, granular fertilizer carriers such as ammonium nitrate, urea, etc., or mixed with fine sand or soil.

[0068] The treatment of plants and plant parts according to the present invention with a composition comprising the compound of the present invention can be carried out directly or by acting on their surroundings, habitats or storage spaces by conventional treatment methods, such as by dipping, spraying, atomizing, irrigation, evaporation, dusting, misting, broadcasting, foaming, smearing, coating, watering (irrigation), dripping, and for plant propagation materials, especially seeds, dry seed treatment, wet seed treatment, slurry treatment, crusting, coating with one or more coatings, etc. The active substance can also be effectively utilized by ultra-low volume method or by injecting a preparation comprising the compound of the present invention or the compound of the present invention itself into the soil.

[0069] The agricultural and horticultural insecticide containing the oxadiazole compound represented by the general formula (I) of the present invention or its salt as an active ingredient is suitable for controlling various agricultural, forestry, horticultural, stored-grain pests, sanitary pests, nematodes and other pests that cause damage to rice, fruit trees, vegetables, other crops and flowers.

[0070] Non-limiting examples of pests that the present invention is intended to control or prevent from attacking useful plants include:

[0071] Examples of the lepidopteran pests include the green caterpillar, the citrus swallowtail, the Japanese bean moth, the sedge armyworm, the cuneiform moth, the Asian corn borer, the yellow cutworm, the sugarcane borer, the yellow swallowtail butterfly, and the yellow stem borer.

[0072] Examples of Hemiptera pests include rice green toon, cottony scale, pea aphid (Acyrthosiphon pisum), oak leafhopper, citrus scale, Cordyceps pyrethrum aphid, yellow round-hoofed shield scale, soybean aphid, Bemisia whitefly, corn aphid, polyphagous leafhopper, small green leafhopper, pine leafhopper, peach aphid, apple psyllid, apple leaf bug (Heterocordylus flavipes), apple gall aphid (Myzus malisuctus), apple aphid, apple leafhopper, apple aphid, and cotton aphid.

[0073] Examples of the coleopteran pests include the green bean weevil, the rice weevil, the yellow cabbage flea beetle, the yellow star longhorn beetle, the yellow spotted longhorn beetle, the corn weevil, the red flour beetle, the rice weevil, the potato leaf beetle, the beet flea beetle, the large green scarab beetle, the cucumber flea beetle, and the pine sawyer beetle.

[0074] Examples of Diptera pests include Culex pipiens pallens, beet leafminer, liriomyza huidobrensis, housefly, cucurbit fruitfly, cherry fruitfly, Anopheles sinensis, and apple fruitfly.

[0075] Examples of the Hymenoptera pests include cabbage sawfly, chestnut gall wasp, black-backed radish sawfly, rose sawfly, Japanese turnip sawfly, leafcutter ants, and fire ants.

[0076] Examples of the Orthoptera pests include the southern rice grasshopper, the small-winged rice grasshopper, the migratory locust, and the short-winged rice grasshopper.

[0077] Examples of the Thysanoptera pests include rice thrips, rice pipe thrips, yellow thrips, citrus thrips, and lily thrips.

[0078] Examples of the Acarina pests include the hawthorn spider mite, the redback spider, the two-spotted spider mite, the citrus mites, and the apple mites.

[0079] Examples of the Isoptera pests include Coptotermes formosanus, Japanese carpenter ants, Coptotermes spp., and Reticulitermes speratus.

[0080] Examples of the pests of the order Blattaria include Periplaneta fuliginosa, German cockroach, Oriental cockroach, Periplaneta japonica, and American cockroach.

[0081] Examples of the order Siphonaptera include human fleas, cat fleas, and chicken fleas.

[0082] Examples of nematodes include strawberry bud nematodes, rice stem nematodes, northern root-knot nematodes, southern root-knot nematodes, and soybean cyst nematodes. Examples of mollusks include golden apple snails, giant African land snails, yellow slugs, and snails.

[0083] Furthermore, the agricultural and horticultural insecticide of the present invention also has a strong insecticidal effect against the tomato leafminer, which is another pest.

[0084] In addition, examples of parasitic ticks that live inside or outside animals and are to be controlled include the microtiscus, the haemaphysalis japonicus, and the mites.

[0085] When the external or internal parasite control agent of the present invention is used as a medicament for humans or animals belonging to mammals or birds other than humans, the optimal amount (effective amount) of the active ingredient will vary depending on the distinction between treatment and prevention, the type of infecting parasites, the type and degree of infection, the dosage form, etc., but in general, in the case of oral administration, the optimal amount (effective amount) of the active ingredient is in the range of about 0.0001 to 10,000 mg / kg body weight per day. In the case of parenteral administration, the optimal amount (effective amount) of the active ingredient is in the range of about 0.0001 to 10,000 mg / kg body weight per day, and can be administered all at once or in divided doses.

[0086] The concentration of the active ingredient in the external or internal parasite control agent of the present invention is generally 0.001 to 100% by mass, preferably 0.001 to 99% by mass, and more preferably about 0.005 to 20% by mass. The internal parasite control agent of the present invention may be a composition for direct administration or a high-concentration composition that is diluted to an appropriate concentration before use.

[0087] Since the compounds of the present invention have a significant control effect on the pests that cause damage to paddy field crops, dry field crops, fruit trees, vegetables, other crops, and flowers, etc., the desired effects of the agricultural and horticultural insecticides of the present invention can be exerted by applying the compounds to cultivation carriers such as seeds, paddy field water, stems and leaves, or soil in seedling raising facilities, paddy fields, dry fields, fruit trees, vegetables, other crops, and flowers, etc., before or when the pests are confirmed to have appeared, based on the predicted period of pest emergence. Among them, a preferred mode of use is: application to the soil for raising seedlings of crops, flowers, etc., the soil in planting pits during transplanting, the roots of plants, irrigation water, cultivation water in hydroponic cultivation, etc., so that the compounds of the present invention are absorbed by the roots through the soil or without passing through the soil, that is, an application mode utilizing systemic absorption.

[0088] Beneficial plants to which the agricultural and horticultural insecticide of the present invention can be applied are not particularly limited, and examples thereof include cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybeans, red beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leafy vegetables and fruits (cabbage, tomatoes, spinach, broccoli, lettuce, onions, shallots, shallots, green peppers, eggplants, strawberries, peppers, okra, leeks, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, lotus roots, burdocks, etc.), , garlic, chives, etc.), processing crops (cotton, hemp, sugar radish, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), melons (pumpkin, cucumber, watermelon, cantaloupe, muskmelon, etc.), forage grasses (duckgrass, sorghum, timothy, clover, alfalfa, etc.), grasses (Korean grass, bentgrass, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (chrysanthemum, rose, carnation, orchid, tulip, lily, etc.), garden trees (gingko, cherry, coralwood, etc.), forest trees (fir, spruce, pine, cypress, fir, juniper, eucalyptus, etc.), etc.

[0089] Within the scope of the present invention, useful plants include the following plant species: cereals (wheat, barley, rye, oats, rice, corn, sorghum and related species); beets (sugar beet and fodder beet); pome, stone and soft fruits (apple, pear, plum, peach, almond, cherry, strawberry, raspberry and blackberry); legumes (lentil, bean, pea, soybean); oil crops (rape, mustard, olive, sunflower, coconut, castor oil plant, cocoa bean, peanut or soybean); cucurbits (squash, cucumber, melon). ; fiber plants (cotton, flax, hemp, jute); citrus fruits (oranges, lemons, grapefruits, mandarins); vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, red peppers); laurel plants (avocado, cinnamon, camphor) or plants such as tobacco, nuts, coffee, eggplant, sugar cane, tea, pepper, grapevines, hops, bananas and natural rubber plants, as well as turf, ornamental and forest plants, such as flowers, shrubs, broad-leaved trees or evergreen trees, such as conifers, and plant propagation material.

[0090] The composition comprising the compound of the present invention is simple to use. The composition comprising the compound of the present invention is applied to the pest or its growth medium. The dosage of the composition of the present invention varies depending on weather conditions, formulation, timing of application, method of application, application area, target pest, target crop, and the like.

[0091] Preparation Example

[0092] Generally, the compounds of the present invention can be prepared by the methods described in the present invention. Unless otherwise specified, the raw materials, reagents, etc. used to prepare the compounds of the present invention are commercially available or can be prepared by conventional methods in the art.

[0093] Example 1 Preparation of 3-(5-ethylsulfonyl-6-(3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-3-yl)-5-(2-cyclopropylcyclopropyl)-1,2,4-oxadiazole (Compound 8)

[0094]

[0095] Dissolve 10 g (0.025 mol) of 5-ethylsulfonyl-6-(3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridin-2-yl)nicotinonitrile in ethanol (100 mL), add triethylamine (7.0 ml) and hydroxylamine hydrochloride (2.6 g), and stir at 80°C for 1 hour. Add water and extract with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 5-ethylsulfonyl-N'-hydroxy-6-(3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridine-3-carboximidamide. This product is used in the next reaction without purification. 0.15 g of the resulting crude product is dissolved in tetrahydrofuran (4 mL), and triethylamine (0.10 g) and 2-(cyclopropyl)cyclopropanecarbonyl chloride (0.056 g) are added, followed by stirring at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. Dissolved in acetic acid (1 ml), toluene (2 ml) was added, and stirred at 120°C for 1 hour. Saturated aqueous sodium carbonate solution was added, and extraction was performed with ethyl acetate. After concentration under reduced pressure, purification by column chromatography afforded the desired product (yield 40%).

[0096] Example 2 Preparation of 3-(5-ethylsulfonyl-6-(4-isopropyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)pyridin-3-yl)-5-cyclopropyl-1,2,4-oxadiazole (Compound 1)

[0097]

[0098] 8.0 g (0.025 mol) of 5-ethylsulfonyl-6-(4-isopropyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinonitrile was dissolved in ethanol (100 mL), triethylamine (7.1 mL) and hydroxylamine hydrochloride (2.6 g) were added, and the mixture was stirred at 80°C for 1 hour. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the addition product. This product was used in the next reaction without purification. 0.13 g of the crude product was dissolved in tetrahydrofuran (3 mL), triethylamine (0.1 g) and cyclopropanecarbonyl chloride (0.042 g) were added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure, dissolved in acetic acid (1 mL), and toluene (2 mL) was added. The mixture was stirred at 120°C for 1 hour. Saturated aqueous sodium carbonate solution was added, and the mixture was extracted with ethyl acetate. After concentration under reduced pressure, the residue was purified by column chromatography to obtain the target product (yield 30%).

[0099] The compounds shown in the following table were prepared by referring to the methods of the above examples.

[0100]

[0101]

[0102] Biological Example: Insecticide Activity Assay

[0103] Insecticidal activity test against peach aphid (Myzus persicae)

[0104] Mix 10 parts of the compound of formula I of the present invention, 75 parts of toluene, 10 parts of DMF and 5 parts of T-T to prepare an emulsifiable concentrate. Disperse the prepared emulsifiable concentrate in water and dilute it to a 250 ppm solution for use.

[0105] Cabbage was planted in a plastic pot with a diameter of 10 cm and a height of 8 cm, and peach aphids were allowed to reproduce on the cabbage. The number of peach aphids in the pot was then investigated.

[0106] The prepared solution was applied to the stems and leaves of cabbage in pots. After air-drying, the pots were placed in a greenhouse. Six days after application, the number of green peach aphids on the cabbage was counted, and a water blank control was used. The control rate of green peach aphids was calculated using the following equation.

[0107] Control rate = 100-{(T*Ca) / (Ta*C)}*100

[0108] in,

[0109] Ta represents the number of peach aphids in the application area before treatment

[0110] T represents the number of peach aphids after treatment in the application area

[0111] Ca represents the number of peach aphids in the blank control area before watering

[0112] C: represents the number of peach aphids in the blank control area after 6 days.

[0113] The results showed that compounds 1-8 of the present invention had excellent insecticidal effects at 250 ppm, and the control rates all reached 100%.

Claims

1. A compound of formula I, in, Q is selected from Q-1, R1 is H, C1-C6 alkyl; R2 is H, C3-C6 cycloalkyl; R3 is H, C1-C6 alkyl; R 4 and R 5 Each is independently H, C1-C6 alkyl, or C3-C6 cycloalkyl substituted by halogen, C1-C6 alkyl, C1-C6 haloalkyl, or C3-C6 cycloalkyl; X, Y and Z are each independently O or N or C.

2. The compound of formula I according to claim 1, characterized in that R1 is H; R2 is H and cyclopropyl; R3 is H and methyl; R 4 and R 5 Each is independently selected from H, cyclopropyl-substituted cyclopropyl and halogen-substituted cyclopropyl.

3. A compound characterized in that Selected from the following compounds:

4. A composition, characterized in that The composition comprises the compound according to any one of claims 1 to 3 and at least one auxiliary agent selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.

5. Use of the compound according to any one of claims 1 to 3 or the composition according to claim 4 in controlling plant pests.

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