A dioxanyl-substituted meta-diamide compound, compositions, formulations and uses thereof

Abstract

The application belongs to the technical field of pesticides, and relates to a dioxoalkyl-substituted meta-diamide compound, a composition, a preparation and a use thereof.The dioxoalkyl-substituted meta-diamide compound has a structure shown in formula I.The compound has excellent insecticidal effect at a low dose, and has good control effect on various pests.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology and relates to a dioxane-substituted m-diamide compound, its composition, formulation and use. Background Technology

[0002] Pesticides play a vital role in controlling pests and diseases in agriculture and horticulture. Therefore, research on pesticides has been rapidly developing for decades, resulting in a plethora of pesticide types, including organophosphates, organochlorines, carbamates, pyrethroids, neonicotinoids, and chitin synthesis inhibitors. However, the widespread use of pesticides has also brought about significant problems such as food safety concerns, pest resistance, and environmental damage.

[0003] In 2007, Nippon Nippon Agricultural Chemicals Co., Ltd. launched flubendiamide, the first insecticide targeting ryanodine receptors. Due to its significant effect on lepidopteran pests, lack of cross-resistance with other commonly used insecticides, and safety for mammals, it garnered widespread attention upon its release. Subsequently, a development boom ensued for diamide insecticides, expanding their application from lepidopterans to field crops, vegetable cultivation, and the control of sanitary pests. However, with widespread use, safety and resistance issues related to diamide insecticides have emerged. For example, flubendiamide can cause serious harm to some aquatic invertebrates and beneficial organisms (such as silkworms, bees, and earthworms). Therefore, the search for highly effective, low-toxicity, and environmentally friendly new insecticides is urgently needed.

[0004] WO2010018714A1 discloses a series of highly insecticidal resorcinamide compounds, the most representative of which is broflanilide. Developed by Mitsui Chemicals, this compound uses flubendiamide as a lead compound, converting the fatty amino acyl group to benzamide, changing the linkage site from ortho to meta, and introducing a bromine atom and a trifluoromethyl group. Studies have shown that, unlike the ryanodine receptor, the target of traditional diamide insecticides, broflanilide targets GABA-gated chloride channels, inhibiting chloride ion translocation into cells, leading to insect over-excitation and death. Experiments have shown that broflanilide exhibits greater than or equal to 70% activity against both the beet armyworm and the diamondback moth at a concentration of 1 ppm. It not only demonstrates good killing activity against resistant pests but also exhibits high selectivity for insect GABA receptors and is relatively safe and non-toxic to humans and other mammals.

[0005]

[0006] CN112707841B and CN110810409A disclose a series of isophthalamide compounds with cyclopropyl structures, the most representative of which is cyclopropionamide, which uses bromoxynil as a lead compound, converts the N-methyl group to N-cyclopropylmethyl group and introduces an F atom, and has an activity of 50% against rice stem borer at a concentration of 0.453 ppm.

[0007]

[0008] CN115304510B discloses compound 1 (compound number I-2) and compound 2 (compound number I-26), both of which have greater than 90% activity against rice stem borer at a concentration of 5 ppm.

[0009]

[0010] CN110194726A discloses a series of isophthalamide compounds with cyano structures, among which compound 3 (compound number 2.31) and compound 4 (compound number 2.7) have greater than 90% activity against armyworm and diamondback moth at a concentration of 0.5 ppm.

[0011]

[0012] WO2023284645A1 discloses a series of isophthalamide compounds with an allyl structure, among which compounds 5 (compound number 3) and 6 (compound number 7) have greater than 90% activity against armyworm and diamondback moth at a concentration of 1.25 ppm.

[0013]

[0014] Although m-diamide compounds can overcome the resistance problem of diamide compounds to some extent, as the requirements for pesticide use in reality continue to increase, there is a need to continuously develop pesticides with better activity and lower dosage. Summary of the Invention

[0015] The problem the invention aims to solve

[0016] To address the above-mentioned problems, the present invention provides a dioxane-substituted meta-diamid compound, its composition, formulation, and uses.

[0017] Solution for solving the problem

[0018] In a first aspect, the present invention provides a compound of Formula I or a pesticide-acceptable salt, stereoisomer, or metabolite thereof.

[0019]

[0020] in,

[0021] R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl and C3-C6 cycloalkyl;

[0022] R2 is selected from hydrogen, halogen, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 haloalkoxy.

[0023] Preferably, R1 is selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, and C1-C3 haloalkoxy-C1-C3 alkyl; more preferably, R1 is selected from hydrogen and C1-C3 alkyl; more preferably, R1 is selected from hydrogen, methyl, and ethyl; even more preferably, R1 is methyl.

[0024] Preferably, R2 is selected from hydrogen, halogen, C1-C3 haloalkyl, C1-C3 alkoxy and C1-C3 haloalkoxy; preferably, R2 is selected from hydrogen and halogen; more preferably, R2 is selected from hydrogen, fluorine, bromine and iodine; even more preferably, R2 is selected from hydrogen and fluorine.

[0025] In a second aspect, the present invention provides the following compounds or their pesticide-acceptable salts, stereoisomers or metabolites;

[0026]

[0027] Thirdly, the present invention provides a pesticide composition comprising an active ingredient and optionally at least one pesticide-acceptable carrier and / or adjuvant, wherein the active ingredient is the aforementioned compound or a pesticide-acceptable salt, stereoisomer, or metabolite thereof.

[0028] Preferably, the content of the active ingredient in the above pesticide composition is 1wt%-99wt%.

[0029] Fourthly, the present invention provides a pesticide formulation made from the above-mentioned compound or its pesticide-acceptable salt, stereoisomer or metabolite or the above-mentioned pesticide composition.

[0030] Preferably, the formulation of the above-mentioned pesticide preparation is an emulsion, suspension, aqueous solution, microemulsion, water-in-oil emulsion, wettable powder, soluble powder, water dispersible agent, or microcapsule.

[0031] Fifthly, the present invention provides the use of the above-described compounds or their phytochemically acceptable salts, stereoisomers or metabolites, or the above-described pesticide compositions, or the above-described pesticide formulations in the preparation of products for controlling agricultural pests.

[0032] Preferably, in the above-mentioned uses, the pest is at least one of mites, Lepidoptera, Diptera, Thysanoptera, Hemiptera, Isoptera, and Coleoptera pests, with Lepidoptera pests being more preferred.

[0033] In a sixth aspect, the present invention provides a method for controlling agricultural pests, comprising the steps of: applying an effective dose of the above-mentioned compound or its phytochemically acceptable salt, stereoisomer or metabolite, or the above-mentioned pesticide composition, or the above-mentioned pesticide formulation to the agricultural pest to be controlled or its growth medium.

[0034] Preferably, in the above-described method for controlling agricultural pests, the effective dosage is 10 to 1000 grams per hectare, more preferably 20 to 500 grams per hectare.

[0035] In a seventh aspect, the present invention provides a pesticide combination comprising the above-described compound or its pesticide-acceptable salt, stereoisomer or metabolite, or the above-described pesticide composition, or the above-described pesticide formulation, and at least one other pesticide-active compound or fertilizer.

[0036] Preferably, in the above-mentioned pesticide combination, the other pesticide active compounds are fungicides, insecticides, acaricides, herbicides, or plant growth regulators.

[0037] The effects of the invention

[0038] This invention introduces a dioxane structure onto the nitrogen atom of an amide and different substituents onto the benzene ring to obtain compounds of general formula I. These compounds differ significantly in structure from those in the prior art. This change facilitates the binding of the molecule to the target, thereby enabling the compound to exhibit excellent insecticidal effects at low doses. Furthermore, the compounds of this invention demonstrate good control efficacy against a variety of pests. Detailed Implementation

[0039] In this specification, the word "may" has two meanings: to perform a certain process and not to perform a certain process.

[0040] In this specification, references to "some specific / preferred embodiments," "other specific / preferred embodiments," "implementation," etc., refer to specific elements (e.g., features, structures, properties, and / or characteristics) related to that embodiment, which are included in at least one of the embodiments described herein and may or may not be present in other embodiments. Furthermore, it should be understood that these elements may be combined in any suitable manner in various embodiments.

[0041] In this specification, the range of values ​​referred to as "value A to value B" refers to the range including the endpoint values ​​A and B.

[0042] In this instruction manual, when "room temperature" or "room temperature" is used, the temperature can be 15-25℃.

[0043] Terminology Definition

[0044] Unless otherwise specified, the term "C1-C6 alkyl" refers alone or in combination to a saturated straight-chain or branched alkyl group comprising 1 to 6 (particularly 1 to 3) carbon atoms, including (but not limited to) methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2-methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, n-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, and 3,3'-dimethyl-2-butyl, etc. Similarly, the term "C1-C3 alkyl" alone or in combination refers to a saturated straight-chain or branched alkyl group containing 1 to 3 carbon atoms, including methyl, ethyl, propyl, isopropyl, etc.

[0045] Unless otherwise specified, the term "cycloalkyl" refers to a monocyclic saturated aliphatic hydrocarbon group having a specific number of carbon atoms, for example, 3-12 carbon atoms (i.e., C12-C12). 3-12 cycloalkyl groups), 3-10 carbon atoms (C 3-10 cycloalkyl groups), 3-6 carbon atoms (C 3-6 cycloalkyl groups), 4-6 carbon atoms (C 4-6 cycloalkyl groups), 5-6 carbon atoms (C 5-6 (Cycloalkyl). Examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopropyl, 2-ethyl-cyclopentyl, dimethylcyclobutyl, etc.

[0046] Unless otherwise specified, the term "C1-C6 alkoxy" alone or in combination represents the group "C1-C6 alkyl-O-", wherein "C1-C6 alkyl" means as defined above. "O(C 1-6 Alkyl groups include (but are not limited to) methoxy (-OCH3), ethoxy (-OCH2CH3), n-propoxy (-OCH2CH2CH3), isopropoxy (-OCH(CH3)2), n-butoxy (-OCH2CH2CH2CH3), sec-butoxy (-OCH(CH3)CH2CH3), isobutoxy (-OCH2CH(CH3)2), tert-butoxy (-OC(CH3)3), n-pentoxy (-OCH2CH2CH2CH2CH3), and neopentoxy (-OCH2C(CH3)3), etc.

[0047] Unless otherwise specified, the terms "halogen" or "halogenated" refer to F, Cl, Br, and I. The term "halogenated alkyl" refers to an alkyl group as defined above in which one, two, or more hydrogen atoms, or all hydrogen atoms, are replaced by a halogen. Representative examples of halogenated alkyl groups include CCl3, CF3, CHCl2, CH2Cl, CH2Br, CH2I, CH2CF3, and CF2CF3.

[0048] This invention comprises "pesticide-acceptable salts" of the compounds of this invention, which can be produced by reacting the compounds of this invention with an acid or a base. Certain compounds, particularly those having acidic or basic groups, can also be in the form of, preferably, pesticide-acceptable salts. The term "pesticide-acceptable salt" refers to those salts that retain the pesticide efficacy and properties of a free base or free acid, which are not pesticide- or otherwise undesirable. Pesticide-acceptable salts generally include (but are not limited to) salts formed by reacting the compounds of this invention with pesticide-acceptable inorganic or organic acids; such salts are also known as acid addition salts. Common inorganic acids include (but are not limited to) hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, sulfuric acid (which can form sulfates or acid sulfates), and phosphoric acid (which can form phosphates or acid phosphates). Common organic acids include (but are not limited to) trifluoroacetic acid, citric acid (which can form mono-, di-, or tri-salts of citrate), maleic acid (which can form mono- or di-salts of maleic acid), fumaric acid (which can form mono- or di-salts of fumaric acid), succinic acid (which can form mono- or di-salts of succinic acid), tartaric acid (which can form mono- or di-salts of tartaric acid), oxalic acid (which can form mono- or di-salts of oxalic acid), oxalic acid (which can form mono- or di-salts of oxalic acid), lactic acid, pyruvic acid, salicylic acid, formic acid, acetic acid, propionic acid, benzoic acid, glycolic acid, methanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. Agrochemically acceptable salts may also include salts formed by the compounds of this invention with agrochemically acceptable organic or inorganic bases; such salts are also known as alkali addition salts. Common alkali addition salts include (but are not limited to) alkali metal salts, such as lithium, sodium, or potassium salts; alkaline earth metal salts, such as calcium or magnesium salts; and organic base salts, such as ammonium salts or N-containing organic bases formed with N-groups. + (C 1-6 Alkyl)4 salts. Common inorganic or organic bases include (but are not limited to) lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, magnesium carbonate, calcium carbonate, ammonia, triethylamine, or tetrabutylammonium hydroxide, etc. Pesticide-acceptable salts can be synthesized by general chemical methods.

[0049] Unless otherwise specified, the term "stereoisomer" refers to compounds having the same chemical structure but with different spatial arrangements of atoms or groups. Stereoisomers include enantiomers, diastereomers, conformational isomers (rotational isomers), geometric isomers (cis / trans) isomers, and inhibited isomers. Any mixture of stereoisomers obtained can be separated into pure or substantially pure geometric isomers, enantiomers, and diastereomers based on differences in the physicochemical properties of the components, for example, by chromatography and / or fractional crystallization.

[0050] dioxane-substituted meta-diamide compounds

[0051] This invention provides a compound of Formula I or a pesticide-acceptable salt, stereoisomer, or metabolite thereof.

[0052]

[0053] in,

[0054] R1 is selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 haloalkoxy-C1-C6 alkyl and C3-C6 cycloalkyl;

[0055] R2 is selected from hydrogen, halogen, C1-C6 haloalkyl, C1-C6 alkoxy, and C1-C6 haloalkoxy.

[0056] In one specific embodiment of the present invention, R1 is selected from hydrogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy-C1-C3 alkyl, and C1-C3 haloalkoxy-C1-C3 alkyl.

[0057] In one specific embodiment of the present invention, R1 is selected from hydrogen and C1-C3 alkyl groups.

[0058] In one specific embodiment of the present invention, R1 is selected from hydrogen, methyl, and ethyl.

[0059] In one specific embodiment of the present invention, R1 is methyl.

[0060] In one specific embodiment of the present invention, R2 is selected from hydrogen, halogen, C1-C3 haloalkyl, C1-C3 alkoxy, and C1-C3 haloalkoxy.

[0061] In one specific embodiment of the invention, R2 is selected from hydrogen and halogens.

[0062] In one specific embodiment of the present invention, R2 is selected from hydrogen, fluorine, bromine and iodine.

[0063] In one specific embodiment of the invention, R2 is selected from hydrogen and fluorine.

[0064] Specifically, the dioxane-substituted m-diamide compounds of the present invention include (but are not limited to) the following compounds:

[0065]

[0066] The present invention also provides a method for preparing the above-mentioned compound, which may include the following steps:

[0067] (1) Compound II-1 reacts with an acyl chloride reagent to give compound II-2.

[0068]

[0069] (2) Compound II-2 reacts with compound II-3 under the action of an acid-binding agent to give compound II-4.

[0070]

[0071] (3) Compound II-4 reacts with a reducing agent to give compound II-5.

[0072]

[0073] (4) Compound II-5 reacts with compound II-6 under the action of a base to give compound II-7.

[0074]

[0075] (5) Compound II-7 and compound II-8 react under the action of an acid-binding agent to give compound I.

[0076]

[0077] In one specific embodiment of the present invention, in step (1) of the above preparation method, the acyl chloride reagent may be selected from at least one of oxalyl chloride and thionyl chloride.

[0078] In one specific embodiment of the present invention, in step (1) of the above preparation method, the acyl chloride reagent can be thionyl chloride.

[0079] In one specific embodiment of the present invention, in step (2) of the above preparation method, the acid-binding agent may be selected from at least one of triethylamine and N,N-diisopropylethylamine.

[0080] In one specific embodiment of the present invention, in step (2) of the above preparation method, the acid-binding agent can be N,N-diisopropylethylamine.

[0081] In one specific embodiment of the present invention, in step (3) of the above preparation method, the reducing agent may be selected from at least one of iron powder-ammonium chloride and stannous chloride-hydrochloric acid.

[0082] In one specific embodiment of the present invention, in step (3) of the above preparation method, the reducing agent can be stannous chloride-hydrochloric acid.

[0083] In one specific embodiment of the present invention, in step (4) of the above preparation method, the alkali may be selected from at least one of potassium carbonate, sodium carbonate, cesium carbonate, N,N-diisopropylethylamine and sodium hydroxide.

[0084] In one specific embodiment of the present invention, in step (4) of the above preparation method, the base can be N,N-diisopropylethylamine.

[0085] In one specific embodiment of the present invention, in step (5) of the above preparation method, the acid-binding agent can be 4-dimethylaminopyridine.

[0086] pesticide compositions

[0087] The present invention provides a pesticide composition comprising an active ingredient and optionally at least one pesticide-acceptable carrier and / or adjuvant, wherein the active ingredient is the above-mentioned compound or a pesticide-acceptable salt, stereoisomer or metabolite thereof.

[0088] In one specific embodiment of the present invention, the content of the active ingredient in the above-mentioned pesticide composition can be 1wt%-99wt%.

[0089] In one specific embodiment of the present invention, the carrier in the above-mentioned pesticide composition can be a solid carrier or a liquid carrier.

[0090] In one specific embodiment of the present invention, the solid carrier in the above-mentioned pesticide composition may be natural or synthetic clay and silicate, such as natural silica and diatomaceous earth, magnesium silicate (e.g., talc), magnesium aluminum silicate (e.g., kaolinite, kaolin, montmorillonite and mica), white carbon black, calcium salts (e.g., calcium carbonate, light calcium carbonate, calcium sulfate), sodium sulfate, amine salts (e.g., ammonium sulfate, hexamethylenediamine).

[0091] In one specific embodiment of the present invention, the liquid carrier in the above-mentioned pesticide composition may be aromatic hydrocarbons (e.g., benzene, xylene, toluene, etc.), chlorinated hydrocarbons (chlorobenzene, vinyl chloride, chloroform, dichloromethane, etc.), aliphatic hydrocarbons (e.g., petroleum fractions, cyclohexane, light mineral oil), alcohols (e.g., isopropanol, butanol, ethylene glycol, glycerol, and cyclohexanol, etc.), as well as their ethers and esters, and ketones (e.g., acetone, cyclohexanone, dimethylformamide, and N-methylpyrrolidone).

[0092] In one specific embodiment of the present invention, the adjuvant in the above-mentioned pesticide composition may include a surfactant.

[0093] In one specific embodiment of the present invention, the surfactant in the above-mentioned pesticide composition can be at least one of ionic or nonionic emulsifiers, dispersants, and wetting agents. For example, the emulsifier can be polyoxyethylene fatty acid ester, polyoxyethylene fatty alcohol ether, polyoxyethylene fatty amine, and commercially available emulsifiers (e.g., Agricultural Emulsion 2201B, Agricultural Emulsion 0203B, Agricultural Emulsion 100#, Agricultural Emulsion 500#, Agricultural Emulsion 600#, Agricultural Emulsion 600-2#, Agricultural Emulsion 1601, Agricultural Emulsion 2201, Agricultural Emulsion NP-10, Agricultural Emulsion NP-15, Agricultural Emulsion 507#, Agricultural Emulsion OX-635, Agricultural Emulsion OX-622, Agricultural Emulsion OX-653, Agricultural Emulsion OX-667, Ningru 36#); the dispersant can be sodium lignosulfonate, dispersing agent, calcium lignosulfonate, methylnaphthalenesulfonic acid formaldehyde condensate, etc.; the wetting agent can be sodium lauryl sulfate, sodium dodecylbenzenesulfonate, sodium alkylnaphthalenesulfonate, etc.

[0094] pesticide formulations

[0095] The present invention provides a pesticide formulation made from the above-described compound or its pesticide-acceptable salt, stereoisomer or metabolite or the above-described pesticide composition.

[0096] In one specific embodiment of the present invention, the formulation of the above-mentioned pesticide preparation is an emulsion, suspension, aqueous solution, microemulsion, water-in-oil emulsion, wettable powder, soluble powder, water dispersible agent, or microcapsule.

[0097] In one specific embodiment of the present invention, the formulation of the above-mentioned pesticide preparation can be an emulsion, suspension, wettable powder or water dispersible agent.

[0098] In one specific embodiment of the present invention, the above-mentioned pesticide formulation can be prepared by a common method. For example, the active substance is mixed with a liquid solvent and / or a solid carrier, and surfactants (e.g., emulsifiers, dispersants, stabilizers, and wetting agents) are added simultaneously. Other adjuvants (e.g., binders, defoamers, antioxidants, etc.) may also be added.

[0099] Uses of pesticides

[0100] The present invention provides the use of the above-described compounds or their phytochemically acceptable salts, stereoisomers or metabolites, or the above-described pesticide compositions, or the above-described pesticide formulations in the preparation of products for controlling agricultural pests.

[0101] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be at least one of the following: mites, lepidopterans, dipterans, tsanoptera, hemiptera, isoptera, and coleopterans.

[0102] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be lepidopteran pests, such as armyworms, beet armyworms, diamondback moths, cutworms, yellow cutworms, cotton bollworms, bean loopers, forked loopers, tree loopers, spruce leaf rollers, rice stem borers, apple leaf rollers, pine caterpillars, southwestern corn stalk borers, Egyptian borers, South American corn seedling borers, privet leaf rollers, plum fruit moths, pear fruit moths, cotton bollworms, tobacco bud borers, corn ear borers, cabbage borers, and fall webworms. Apple leafminer, tomato leafminer, coffee leafminer, spiral leafminer, grape berry leafroller, beet webworm, gypsy moth, tussock moth, peach leafminer, yellow tent caterpillar, cabbage looper, yellow fir tussock moth, corn borer, small-eyed looper, cotton bollworm, Xinjiang looper, round-handled boat moth, potato tuber moth, citrus leafminer, European white butterfly, alfalfa green looper, diamondback moth, soybean looper, wheat moth, grape leafroller, grassland looper, sea gray-winged looper, beet armyworm, green oak moth, and pink-striped looper, etc.

[0103] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be hemiptera pests (bedbugs, aphids, leafhoppers, whiteflies, scale insects, cicadas), such as *Pseudomorphus simonii*, *Corn long bug*, *Black-spotted tobacco mirid bug*, *Cotton red bug*, *Wheat flat shield bug*, *Tobacco bug*, *Cotton red bug*, *American pasture mirid bug*, *Pasture mirid bug*, *Rice green bug*, *Sacchariformis lace bug*, *Larch ball aphid*, *Sacchariformis simonii*, *Strawberry root aphid*, *Apple aphid*, *Cotton aphid*, *North American tea aphid*, *Leaf roll aphid*, and *Pea aphid*. The species include potato aphid, silver leaf whitefly, apricot roundtail aphid, cabbage aphid, Caucasian fir ball aphid, spruce ball aphid, Jugenxi roundtail aphid, broad bean leafhopper, peach large-tail aphid, wheat long-tube aphid, euphorbia long-tube aphid, rose tube aphid, vegetable pruning tail aphid, wheat webless aphid, winter onion head aphid, plum head aphid, rice planthopper, stalked gall aphid, sugarcane planthopper, hop wart aphid, apple psyllid, pear psyllid, corn aphid, cereal overflow tube aphid, wheat two-fork aphid, whitefly, and grape root phylloxera, etc.

[0104] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be thrips, such as orchid thrips, brown tobacco thrips, alfalfa flower thrips, oriental flower thrips, bellflower thrips, rice thrips, palm thrips, western flower thrips, cotton thrips, yellow thrips, and tobacco thrips.

[0105] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be dipteran pests (flies, mosquitoes), such as Aedes aegypti, Aedes albopictus, Aedes piscis, fruit fly gnatus, Anopheles pentatylens, Anopheles leptolegs, Anopheles malariae, Anopheles leptolegs, Anopheles minimus, Anopheles tetratylens, blowfly, Mediterranean fruit fly, golden maggot fly, deer fly, sorghum gall midge, Culex pipiens fasciatus, Aedes mosquito, Culex quinquefasciatus, Aedes mosquito, melon fly, olive fruit fly, rapeseed Leaf gall midge, onion fly, wheat field seed fly, gray field seed fly, cabbage root fly, human skin fly, small toilet fly, horse fly, tsetse fly, spiky tsetse fly, peanut field gray field seed fly, striped tsetse fly, vegetable leafminer, American leafminer, copper green fly, silky green fly, wheat gall midge, autumn housefly, housefly, stable carrion fly, sheep fly, European straw fly, henbane fly, turnip fly, cherry fruit fly, apple fruit fly, red-tailed flesh fly, stable stinging fly, horsefly, red barnacle fly, and European giant mosquito, etc.

[0106] In one specific embodiment of the present invention, the pests used in the above-mentioned uses can be orthoptera (crickets, grasshoppers, locusts), such as house crickets, mole crickets, migratory locusts, black locusts with two stripes, red-legged black locusts, Mexican black locusts, migratory black locusts, rock-dwelling black locusts, striped red locusts, American desert locusts, African desert locusts, Moroccan horn locusts, garden katydids, Senegalese small car locusts, stink gland locusts, Italian locusts, Australian locusts, and brown migratory locusts, etc.

[0107] In one specific embodiment of the present invention, the pests used in the above-mentioned uses can be hymenoptera pests (ants, bees, wasps, leafhoppers), such as Xinjiang cabbage leafhoppers, leafcutter ants, *Hymenopterus* genus, black hairy ants, small yellow house ants, tropical fire ants, red fire ants, black fire ants, southern fire ants, red ants, big-headed ants, velvet ants, bumblebees, bumblebees, yellow-edged hornets, hornets, and Argentine ants, etc.

[0108] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be Coleoptera pests (beetles), such as pear narrow-necked beetle, straight-striped click beetle, dark-colored click beetle, Mexican boll weevil, apple flower weevil, beet gnat beetle, pit borer, broad bean weevil, pea weevil, European bean weevil, apple leaf roller, beet beetle beetle, golden flower beetle, cabbage seed beetle, bladder beetle, beet leg beetle, asparagus leaf beetle, longhorn leaf beetle, South American leaf beetle, corn root leaf beetle, Mexican Ladybug, tobacco flea beetle, cotton weevil variant, European pine bark weevil, Egyptian alfalfa leaf weevil, purple alfalfa leaf weevil, spruce bark beetle, tobacco leaf beetle, black-horned leaf beetle, potato leaf beetle, rice water weevil, rapeseed leaf beetle, large chestnut gill beetle, May gill beetle, rice leaf beetle, grape black-eared beetle, strawberry root weevil, horseradish leaf beetle, leaf-eating gill beetle, garden flea beetle, soybean pale-footed flea beetle, yellow striped vegetable flea beetle, Japanese scarab beetle, pea leaf weevil and grain weevil, etc.

[0109] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be cockroaches, such as German cockroaches, American cockroaches, Japanese cockroaches, brown cockroaches, Australian cockroaches, and Oriental cockroaches.

[0110] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be isoptera (termites), such as yellow-legged reticulate termites, southern reticulate termites, European reticulate termites, black-breasted reticulate termites, and house termites.

[0111] In one specific embodiment of the present invention, the pests used in the above-mentioned uses can be flea pests (fleas), such as cat fleas, dog fleas, rat fleas, itchy fleas, skin-penetrating fleas, and disease-carrying fleas.

[0112] In one specific embodiment of the present invention, the pests used in the above-mentioned uses can be Thysanura pests (silverfish, domestic silverfish), such as silverfish and spotted silverfish.

[0113] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be chiropterans (e.g., centipedes) or millipedes.

[0114] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be springtail pests, such as those of the genus *Echinochloa*.

[0115] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be nematodes, such as plant parasitic nematodes like root-knot nematodes, northern root-knot nematodes, southern root-knot nematodes, Javan root-knot nematodes, and other root-knot nematode genera; cyst-forming nematodes, such as potato golden nematode and other coccidioidomycete nematodes; cereal cyst nematodes, soybean cyst nematodes, beet cyst nematodes, clover cyst nematodes, and other cyst nematode genera; seed gall nematodes; grain nematodes; stem and leaf nematodes, such as the genus *Sclerotium*; stinging nematodes, such as weed stinging nematodes and other needle-stinging nematode genera; pine nematodes, such as pine wood nematodes and other *Sclerotium* genera; annular nematodes, such as the genera *Anoplophora*, *Small annular nematodes*, *Rotala*, and *Meso annular nematodes*; bulb nematodes, rotten stem nematodes, sweet potato stem nematodes, and others. *Heterocystis*; *Trichoderma*, *Trichoderma*; *Helical*; *Sheath Nematodes* and *Sheath-shaped Nematodes*, *Sheath Nematodes* and *Hemi-rotor Nematodes*; *Root-burrowing Nematodes*; *Crown Nematodes*, *Gymnocystis*; *Pseudo-root-knot Nematodes*, *Pearl Nematodes*; *Nematodes*, *Leptochrysis* and other *Leptochrysis*; *Root-rot Nematodes*, *Piercing Root-rot Nematodes*, *Body-short-bodied Nematodes* and other *Root-rot Nematodes*; *Perforating Nematodes*, *Banana Perforating Nematodes* and other *Perforating Nematodes*; *Kidney Nematodes*, *Coil Nematodes* and other *Kidney Nematodes*; *Residual Root Nematodes*, *Primitive Hairy Nematodes* and other *Hairy Hairy Nematodes*; *Pseudo-hair Nematodes*; *Stuttering Nematodes*, *Portulaca purpurea dwarfing nematodes*, *Colournea* dwarfing nematodes and other dwarfing nematodes; *Citrus nematodes*, *Hemi-piercing Nematodes*; *Scytherium*, *Scytherium*; and other plant-parasitic nematodes.

[0116] In one specific embodiment of the present invention, the pests used in the above-mentioned applications can be arachnid pests, such as those in the order Araneae, such as the red-spotted spider spider and the brown silk spider; those in the orders Acari, such as the families of Soft Ixodidae, Hard Ixodidae, and Sarcoptidae, such as the long-spotted tick, tropical flower tick, Persian sharp-edged tick, cattle tick, small cattle tick, Ankylornis, American hard tick, castor hard tick, black-footed hard tick, perringed hard tick, Pacific hard tick, avian spiny tick, chicken spiny tick, sheep scabies, brown dog tick, human scabies mite, and gall mite (such as the apple rust mite); mites (such as the lateral tarsier); fine mites (such as the purple short-haired mite); and spider mites (such as the carmine spider mite, the kaempferi spider mite, the Pacific spider mite, the cotton spider mite and the two-spotted spider mite, the apple spider mite and the citrus spider mite, etc.).

[0117] Methods of controlling agricultural pests

[0118] The present invention provides a method for controlling agricultural pests, comprising the following steps: applying an effective dose of the above-mentioned compound or its phytochemically acceptable salt, stereoisomer or metabolite, or the above-mentioned pesticide composition, or the above-mentioned pesticide formulation to the agricultural pest to be controlled or its growth medium.

[0119] In one specific embodiment of the present invention, the effective dosage in the above-described method for controlling agricultural pests can be from 10 grams to 1000 grams per hectare.

[0120] In one specific embodiment of the present invention, the effective dosage in the above-described method for controlling agricultural pests can be from 20 grams to 500 grams per hectare.

[0121] Combined pesticide formulation

[0122] The present invention provides a pesticide combination comprising the above-described compound or its pesticide-acceptable salt, stereoisomer or metabolite, or the above-described pesticide composition, or the above-described pesticide formulation, and at least one other pesticide-active compound or fertilizer.

[0123] In one specific embodiment of the present invention, the other pesticide active compounds in the above-mentioned pesticide combination form are fungicides, insecticides, acaricides, herbicides, or plant growth regulators.

[0124] Example

[0125] The technical solution of the present invention will be described in detail below with reference to embodiments. However, those skilled in the art will understand that the following embodiments are only for illustrating the present invention and should not be regarded as limiting the scope of the present invention. Unless otherwise specified in the embodiments, conventional conditions or conditions recommended by the manufacturer shall apply. Reagents or instruments used that do not specify the manufacturer are all commercially available conventional products.

[0126] Various exemplary embodiments, features, and aspects of the present invention will be described in detail below. The term "exemplary" as used herein means "serving as an example, embodiment, or illustration." Any embodiment described herein as "exemplary" is not necessarily to be construed as superior to or better than other embodiments.

[0127] Furthermore, to better illustrate the present invention, numerous specific details are set forth in the following detailed embodiments. Those skilled in the art should understand that the present invention can be practiced without certain specific details. In other instances, methods, means, apparatus, and steps well known to those skilled in the art have not been described in detail in order to highlight the spirit of the present invention.

[0128] Unless otherwise stated, all units used in this specification are international standard units, and all numerical values ​​and ranges appearing in this invention should be understood to include systematic errors that are unavoidable in industrial production.

[0129] DMF N,N-Dimethylformamide DIPEA N,N-Diisopropylethylamine DMAP 4-Dimethylaminopyridine TLC Thin-layer chromatography

[0130] Example 1: Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-{N-[(2-methoxyethoxy)methyl]benzamido}benzamide (I-5)

[0131] (1) Preparation of 2-fluoro-3-nitrobenzoyl chloride (II-2)

[0132]

[0133] At room temperature, DMF (0.20 g, 2.7 mmol) was added to a solution of 2-fluoro-3-nitrobenzoic acid (3.71 g, 20 mmol) and thionyl chloride (16.05 g). The reaction mixture was then heated to 80 °C and reacted for 6 hours. After the reaction was complete as indicated by TLC, the mixture was distilled off the thionyl chloride under reduced pressure to obtain acyl chloride, which was used directly in the next step without further processing.

[0134] (2) Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-nitrobenzamide (II-4)

[0135]

[0136] At room temperature, 2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)aniline (II-3, 4.06 g, 10.0 mmol), DIPEA (5.16 g, 40 mmol), and DMAP (0.98 g, 8 mmol) were added sequentially to a dioxane (40 mL) solution of II-2 (2.0 g, 10.0 mmol). The mixture was heated to 100 °C and reacted for 12 hours. After the reaction was confirmed to be complete by TLC, the reaction solution was cooled to room temperature, filtered to remove insoluble matter, concentrated under reduced pressure, dissolved in ethyl acetate (50 mL), washed successively with saturated sodium bicarbonate aqueous solution and saturated brine, the organic phases were combined and dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (petroleum ether:ethyl acetate = 50:1 to 5:1) to obtain an orange-yellow solid (5.32 g, yield 92%). 1 H NMR (400MHz, CDCl3): δ8.43-8.47(1H,m),8.28-8.38(1H,m),8.17-8.23(2H,m),7.94(1H,s),7.53(1H,t,J=7.6Hz).

[0137] (3) Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-aminobenzamide (II-5)

[0138]

[0139] At room temperature, stannous chloride dihydrate (4.60 g, 20.0 mmol) was added to 20 mL of ethanol containing II-4 (2.89 g, 5.0 mmol), followed by slow dropwise addition of concentrated hydrochloric acid (4 mL) to the reaction mixture. The mixture was heated to 60-65 °C. After TLC showed complete reaction, the reaction mixture was cooled to room temperature and poured into ice water (30 mL). Ethyl acetate (50 mL) was then added to the mixture, followed by slow addition of 1 N sodium hydroxide aqueous solution to neutralize to pH 8-9. The mixture was filtered through diatomaceous earth, the filter cake was washed with ethyl acetate, separated, and the organic layer was dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether:ethyl acetate = 20:1 to 5:1) to give a yellow solid (2.56 g, yield 93%). 1 ¹H NMR (400MHz, DMSO-d⁶): δ 10.48 (¹H, s), 8.40 (¹H, s), 7.95 (¹H, s), 7.94 (¹H, s), 6.98–7.02 (¹H, m), 6.92–6.96 (¹H, m), 6.79–6.83 (¹H, m), 5.41 (¹H, br s). ESI-MS: Theoretical m / z value: 544.9 [M+H] +Measured value: 545.0.

[0140] (4) Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-{[(2-methoxyethoxy)methyl]amino}benzamide (II-7A)

[0141]

[0142] At room temperature, DIPEA (129 mg, 1 mmol) was added to a solution of II-5 (273 mg, 0.5 mmol) in dichloromethane (5 mL), followed by dropwise addition of II-6A (75 mg, 0.6 mmol) to the reaction mixture. The reaction was allowed to proceed at room temperature. After TLC showed the reaction was complete, the reaction mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (petroleum ether:ethyl acetate = 10:1–2:1) to obtain an oil (103 mg, yield: 32%). ESI-MS: Theoretical value: 633 ([M+H)) + ), Measured value: 633.6.

[0143] (5) Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-{N-[(2-methoxyethoxy)methyl]benzamido}benzamide (I-5)

[0144]

[0145] At room temperature, DMAP (16 mg, 0.13 mmol) was added to a solution of II-7A (160 mg, 0.25 mmol) in 1,2-dichloroethane (8 mL), followed by the addition of benzoyl chloride (37 mg, 0.26 mmol) dropwise to the reaction mixture. The reaction mixture was then heated under reflux for 4 hours. After the reaction was complete as indicated by TLC, the reaction mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography (petroleum ether:ethyl acetate = 10:1–3:1) to give a solid (95 mg, yield 51%). 1 H NMR (400MHz, CDCl3): δ8.65-8.67(1H,m),8.18(2H,s),7.91-7.97(3H,m),7.60.-7.63(1H,m),7.52-7.5 6(2H,m),7.33-7.37(2H,m),4.96-5.06(2H,dd,J1=11.2Hz,J2=27.6Hz),3.36-3.47(4H,m),3.20(3H,s).

[0146] Example 2: Preparation of N-[2-bromo-4-(heptafluoroisopropyl-2-yl)-6-(trifluoromethyl)phenyl]-2-fluoro-3-{4-fluoro-N-[(2-methoxyethoxy)methyl]benzamido}benzamide (I-6)

[0147]

[0148] At room temperature, DMAP (16 mg, 0.13 mmol) was added to a solution of II-7A (100 mg, 0.15 mmol) in 6 mL of 1,2-dichloroethane. Then, 4-fluorobenzoyl chloride (II-8, 26.8 mg, 0.17 mmol) was added dropwise to the reaction mixture. The reaction mixture was heated under reflux for 4 hours. After the reaction was complete as indicated by TLC, the reaction mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography (petroleum ether:ethyl acetate = 10:1 to 3:1) to give a solid (63 mg, yield 54%). 1H NMR (400MHz, CDCl3): δ8.58-8.63(1H,m),8.18-8.19(1H,m),8.11(1H,br s),7.92-7.97(3H,m),7.31.-7.38(2H,m),7.19-7.24(2H,m),4.95-5.05(2H,dd,J1=27.2Hz,J2=11.2Hz),3.37-3.47(4H,m),3.20(3H,s).

[0149] Other compounds represented by general formula I can also be prepared in accordance with the methods described above.

[0150] Preparation of the formulation:

[0151] Example 3: Preparation of Emulsion

[0152] An emulsion was prepared by uniformly mixing 20 parts of the compound of the present invention represented by general formula I, 10 parts of polyoxyethylene styrene phenyl ether, and 70 parts of xylene.

[0153] Example 4: Preparation of wettable powder

[0154] A wettable powder was prepared by uniformly mixing 10 parts of the compound of the present invention represented by general formula I, 2 parts of sodium dodecyl sulfate, 2 parts of dialkyl sulfosuccinate, 1 part of sodium salt of β-naphthalenesulfonic acid formaldehyde condensate, and 85 parts of diatomaceous earth.

[0155] Example 5: Preparation of Suspension

[0156] Ten parts of the compound of the present invention represented by general formula I, three parts of sodium salt of β-naphthalenesulfonic acid formaldehyde condensate, one part of tristyrylphenol, five parts of propylene glycol, 0.5 parts of silicone defoamer, and 33.5 parts of water were thoroughly mixed. Then, 0.3 parts of xanthic acid gum and 46.7 parts of water were mixed. Finally, the two mixtures were stirred and mixed again to obtain a suspension.

[0157] Example 6: Preparation of water-dispersant

[0158] 20 parts of the compound of the present invention represented by general formula I, 6 parts of naphthalenesulfonic acid formaldehyde condensate metal salt, 1 part of dialkylsulfonylsuccinate metal salt, and 73 parts of calcium carbonate were uniformly pulverized and mixed, then water was added, kneaded, granulated and dried to obtain water-dispersible granules.

[0159] Bioactivity assay

[0160] Example 7: Insecticidal activity assay against diamondback moth (Plutella xylostella)

[0161] Dissolve the compound dimethyl sulfoxide (DMSO) in water and then prepare 100 mL of each of the following test solutions with concentrations of 100 ppm, 50 ppm, 10 ppm, and 1 ppm using a 0.1% wt Tween 80 solution. (The content of DMSO in the total solution shall not exceed 10%).

[0162] Select fresh, tender rapeseed leaves, cut them into 5 cm sections, and immerse them in the prepared solution for 10 seconds. After air-drying, place them in a 10 cm diameter petri dish lined with filter paper. Inoculate 10 healthy, uniform diamondback moth larvae (3rd instar). The experiment was repeated 4 times, with a water treatment as a blank control. After treatment, the larvae were placed indoors at 24℃, 60%-70% relative humidity, and natural light. After 72 hours, the number of surviving larvae was counted, and the mortality rate was calculated.

[0163] Among some of the tested compounds, compounds I-5 and I-6 showed insecticidal mortality rates exceeding 90% against diamondback moth at a concentration of 1 ppm, and 100% at a concentration of 10 ppm. In contrast, compound I-2 from CN115304510B, used as a positive control, showed a 60% insecticidal mortality rate against diamondback moth at a concentration of 1 ppm.

[0164] Example 8: Insecticidal activity assay against armyworm (Mythimna separata)

[0165] Dissolve the test compound dimethyl sulfoxide (DMSO) and then prepare 100 mL of each of the following test solutions with concentrations of 100 ppm, 50 ppm, 10 ppm, and 1 ppm using a 0.1% wt Tween 80 solution. (The content of DMSO in the total solution shall not exceed 10%).

[0166] Select fresh, tender rapeseed leaves, cut them into 5 cm sections, and immerse them in the prepared solution for 10 seconds. After air-drying, place them in a 10 cm diameter petri dish lined with filter paper. Inoculate 10 healthy, uniform armyworm larvae (3rd instar). The experiment was repeated 4 times, with a water treatment as a blank control. After treatment, the dishes were placed indoors at 24℃, 60%-70% relative humidity, and natural light. After 72 hours, the number of surviving larvae was counted, and the mortality rate was calculated.

[0167] Among some of the tested compounds, compounds I-5 and I-6 exhibited a 100% mortality rate against armyworms at a concentration of 1 ppm. However, compound I-2, used as a positive control in CN115304510B, showed a 70% mortality rate against armyworms at a concentration of 1 ppm.

[0168] It is evident that compounds I-5 and I-6 exhibit excellent insecticidal activity, showing a significant advantage over the positive control compounds.

[0169] As described above, the dioxane-substituted meta-diamid compounds of the present invention have novel structures and exhibit excellent insecticidal activity.

[0170] It should be noted that although the technical solution of the present invention has been described with specific examples, those skilled in the art will understand that the present invention should not be limited thereto.

[0171] The various embodiments of the present invention have been described above. These descriptions are exemplary and not exhaustive, nor are they limited to the disclosed embodiments. Many modifications and variations will be apparent to those skilled in the art without departing from the scope and spirit of the described embodiments. The terminology used herein is chosen to best explain the principles, practical application, or technical improvements to the embodiments in the market, or to enable others skilled in the art to understand the embodiments disclosed herein.

Claims

1. The compound represented by Formula I or its pesticide-acceptable salt, in, R1 is selected from hydrogen and C1-C6 alkyl groups; R2 is selected from hydrogen and halogens.

2. The compound according to claim 1 or a pesticide-acceptable salt thereof, characterized in that, R1 is selected from hydrogen and C1-C3 alkyl groups.

3. The compound according to claim 2 or a pesticide-acceptable salt thereof, characterized in that, R1 is selected from hydrogen, methyl, and ethyl.

4. The compound according to claim 3 or a pesticide-acceptable salt thereof, characterized in that, R1 is a methyl group.

5. The compound according to claim 1 or 2, or a pesticide-acceptable salt thereof, characterized in that, R2 is selected from hydrogen, fluorine, bromine, and iodine.

6. The compound according to claim 5 or a pesticide-acceptable salt thereof, characterized in that, R2 is selected from hydrogen and fluorine.

7. The following compounds or their pesticide-acceptable salts; 。 8. A pesticide composition comprising an active ingredient and optionally at least one pesticide-acceptable carrier and / or adjuvant, said active ingredient being a compound according to any one of claims 1 to 7 or a pesticide-acceptable salt thereof.

9. The pesticide composition according to claim 8, characterized in that, The active ingredient content in the pesticide composition is 1wt%-99wt%.

10. A pesticide formulation made from a compound according to any one of claims 1 to 7 or a pesticide-acceptable salt thereof, or a pesticide composition according to claim 8 or 9.

11. The pesticide formulation according to claim 10, characterized in that, The pesticide formulation is in the form of emulsion, suspension, wettable powder, or water dispersible agent.

12. A pesticide combination composition comprising a compound according to any one of claims 1 to 7 or a pesticide-acceptable salt thereof, or a pesticide composition according to claim 8 or 9, or a pesticide formulation according to claim 10 or 11, and at least one other pesticide-active compound or fertilizer. The other active pesticide compounds are fungicides, insecticides, acaricides, herbicides, or plant growth regulators.

13. Use of the compound according to any one of claims 1 to 7, or a pesticide composition according to claim 8 or 9, or a pesticide formulation according to claim 10 or 11, in the preparation of a product for controlling agricultural pests. The pests are at least one of the following: mites, lepidopterans, dipterans, thalassoptera, hemiptera, isoptera, and coleopterans.

14. The use according to claim 13, characterized in that, The pests in question are lepidopteran pests.

15. A method for controlling agricultural pests, comprising the following steps: Apply an effective dose of the compound according to any one of claims 1 to 7 or a pesticide-acceptable salt thereof, or a pesticide composition according to claim 8 or 9, or a pesticide formulation according to claim 10 or 11, to the agricultural pest to be controlled or its growth medium.

16. The method according to claim 15, characterized in that, The effective dose is 10 to 1000 grams per hectare.

17. The method according to claim 16, characterized in that, The effective dose is 20 to 500 grams per hectare.

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