Amide compound, preparation method therefor, and use thereof

Abstract

Provided are an amide compound, a preparation method therefor, and a use thereof. The amide compound has a structure represented by formula I. The amide compound exhibits high insecticidal activity at a low dosage. Moreover, due to the good efficacy thereof at a low dosage, the amount of pesticide used can be reduced, which is conducive to environmental protection and provides broad application prospects.

Description

An amide compound, its preparation method and application Technical Field

[0001] This application belongs to the field of insecticides, specifically relating to an amide compound, its preparation method, and its application. Background Technology

[0002] In agricultural and horticultural crop production, pest damage remains severe, and chemical control remains the primary means of combating it. However, due to the long-term, large-scale, and unscientific use of pesticides, some pests have developed resistance to existing pesticides. Furthermore, some pesticides are banned or restricted due to environmental factors. Therefore, the market urgently needs to develop new pesticides that are more efficient, less toxic, and more environmentally friendly.

[0003] The insecticidal activity of amide compounds has been reported in the prior art. For example, patent CN108137548A discloses compounds CK1 (i.e., compound I-5 in CN108137548A), CK2 (i.e., compound I-15 in CN108137548A), CK3 (i.e., compound I-16 in CN108137548A), CK4 (i.e., compound I-20 in CN108137548A), CK5 (i.e., compound 49 in CN106414441B), CK6 (i.e., compound 3 in CN107428759B), CK7 (i.e., compound 13 in CN107428759B), and CK8 (i.e., compound 69 in CN107428759B) and their insecticidal activity. Although these disclosed compounds have insecticidal activity, their insecticidal effect is poor at low doses.

[0004] In this field, the development of more efficient new pesticides to meet the needs of agriculture and forestry remains a desirable goal. Summary of the Invention

[0005] To address the shortcomings of existing technologies, the purpose of this application is to provide an amide compound, its preparation method, and its application. The amide compound exhibits excellent insecticidal effects at low doses, requires low dosage, and is more environmentally friendly.

[0006] To achieve this objective, the following technical solution is adopted in this application:

[0007] On the one hand, this application provides an amide compound having the structure shown in Formula I:

[0008] In formula I,

[0009] R is selected from hydrogen, halogen, methyl, cyclopropyl, halogen-substituted methyl, cyano, or phenyl with 1-5 R3 substitutions;

[0010] Wherein: each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom;

[0011] R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, and C1-C3 haloalkylthio-substituted C1-C3 alkyl. C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, 1-5 R3-substituted benzyl, C2-C6 alkylacyl, C3-C6 cycloalkylacyl, C1-C6 haloalkylacyl, C3-C6 halocycloalkylacyl, 1-5 R3-substituted benzoyl or 1-4 R3-substituted pyridyl, where R3 is defined as described above;

[0012] in:

[0013] R4 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C4 alkyl, C1-C6 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, or C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl.

[0014] When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above;

[0015] When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

[0016] Preferably, in formula I,

[0017] R is selected from hydrogen, halogen, methyl, cyclopropyl, trifluoromethyl, cyano, or phenyl with 1-5 R3 substitutions;

[0018] Wherein: each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom;

[0019] R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, and C1-C3 haloalkylthio-substituted C1-C3 alkyl. Alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, R3-substituted benzyl, C2-C6 alkylacyl, C3-C6 cycloalkylacyl, C1-C6 haloalkylacyl, C3-C6 halocycloalkylacyl, 1-5 R3-substituted benzoyl or 1-4 R3-substituted pyridyl, where R3 is defined as described above;

[0020] in:

[0021] R4 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C4 alkyl, C1-C6 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, or C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl.

[0022] When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above;

[0023] When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

[0024] More preferably, in formula I,

[0025] R is selected from hydrogen, chlorine, bromine, iodine, cyclopropyl, trifluoromethyl, cyano, or phenyl groups with 1-5 R3 substitutions;

[0026] Wherein: each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom;

[0027] R4 is selected from hydrogen atom, halogen atom, cyano, nitro, amino, hydroxyl or mercapto;

[0028] R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C 1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, C2-C6 alkyl acyl, C3-C6 cycloalkyl acyl, C1-C6 haloalkyl acyl, C3-C6 halocycloalkyl acyl, 1-5 R3-substituted benzoyl groups or 1-4 R3-substituted pyridyl groups, where R3 is defined as described above;

[0029] in:

[0030] R4 is selected from hydrogen, C1-C6 alkyl, and C3-C6 cycloalkyl;

[0031] When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above;

[0032] When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

[0033] Amide compounds having the structure shown in Formula I of this application can achieve high insecticidal activity within 3 days at low doses; and because of their good efficacy at low doses, they reduce the harm to plants and humans caused by excessive drug concentrations, and produce less drug residues during application, which is more environmentally friendly.

[0034] As a further preferred technical solution of this application, the amide compound is any one of the compounds shown in Table 1 below that have general formula I.

[0035] Table 1

[0036] It should be noted that "H" represents hydrogen atom, "N" represents nitrogen atom, "O" represents oxygen atom, "S" represents sulfur atom, "F" represents fluorine atom, "Cl" represents chlorine atom, "Br" represents bromine atom, "I" represents iodine atom, "CF3" represents trifluoromethyl, "CN" represents cyano, "CH2CN" represents cyanomethyl, "CH2CH2CN" represents cyanoethyl, "CH2OCH3" represents methoxymethyl, "CH2OCH2CH3" represents ethoxymethyl, and "CH3" represents methyl.

[0037] In this application, as a particularly preferred technical solution, the amide compound is selected from any one of the following compounds:

[0038] The alkyl group referred to in this application refers to a straight-chain or branched alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. A haloalkyl group is a group in which the hydrogen atom of the alkyl group is replaced by one or more halogen atoms. An alkoxy group is a group with an oxygen atom attached to the alkyl terminus, such as methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, etc. A haloalkoxy group is a group in which the hydrogen atom of the alkoxy group is replaced by one or more halogen atoms, and the halogen is F, Cl, Br, or I.

[0039] As used in this application, the term "C1-C4 alkyl" refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms, and includes, without limitation, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, etc. The term "C1-C4 alkoxy" refers to a straight-chain or branched alkoxy group having 1 to 4 carbon atoms, and includes, without limitation, methoxy, ethoxy, n-propoxy, isopropoxy, and tert-butoxy, etc. "C1-C4 haloalkyl" refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms substituted with halogen atoms, and includes, without limitation, trifluoromethyl, difluoromethyl, 1,1,1-trifluoroethyl, pentafluoroethyl, heptafluoroisopropyl, etc. "C1-C4 haloalkoxy" refers to a straight-chain or branched alkoxy group having 1 to 4 carbon atoms substituted with halogen atoms, and includes, without limitation, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, etc. As used in this application, the term "C3-C6 cycloalkyl" refers to a cyclic alkyl group having 3 to 6 carbon atoms, and includes, without limitation, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "C3-C6 halocycloalkyl" as used in this application refers to a cyclic alkyl group having 3 to 6 carbon atoms with halogen substitution on the ring, and includes, without limitation, 1-chlorocyclopropyl, 1-fluorocyclopropyl, perfluorocyclopropyl, etc.

[0040] In this application, C1-C4, C3-C6, etc., preceding the specific group indicate the number of carbon atoms contained in the group. For example, C1-C4 indicates a group with 1, 2, 3, or 4 carbon atoms, C3-C6 indicates a group with 3, 4, 5, or 6 carbon atoms, and so on.

[0041] The compound of general formula I of this application can be prepared by the following method, unless otherwise specified, the definitions of each group in the reaction formula are the same as above.

[0042] (i): The reaction of compound of general formula II with compound of general formula III yields compound of general formula I. a Compounds.

[0043] In this application, in step 1-(i), the molar ratio of compound of general formula II to compound of general formula III is 0.25-1:1, and the reaction is carried out in the presence of an alkaline substance such as an organic base and / or an inorganic base. Preferably, the organic base is any one or a combination of at least two of triethylamine, N,N-diisopropylethylamine, pyridine, 2-methylpyridine, 4-N,N-dimethylaminopyridine (DMAP), 1,8-diazobisspirocyclic [5.4.0]undec-7-ene (DBU), N-methylmorpholine, N-methylpiperidine, or N,N-dimethylpiperazine. Preferably, the inorganic base is any one or a combination of at least two of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, or sodium hydride. The reaction temperature is greater than or equal to room temperature and less than or equal to the boiling point of the reaction solvent. The reaction time is 2-48 hours.

[0044] According to the above preparation of general formula I a The method of reacting a compound of general formula IV with a compound of general formula III to obtain a compound of general formula I. b Compounds.

[0045] (ii): Compound of general formula IV is coupled and acylated to obtain compound of general formula I. c Compounds.

[0046] In this application, a compound of general formula IV (R = Br, I) reacts with cyclopropylboronic acid, methylboronic acid, or a substituted phenylboronic acid in the presence of a catalyst and an inorganic base. The catalyst is tetrakis(triphenylphosphine)palladium, palladium acetate, [1,1-bis(diphenylphosphine)ferrocene]palladium dichloride, bis(triphenylphosphine)palladium dichloride, bis(dibenzylacetone)palladium, or a 1,1-bis(diphenylphosphine)ferrocene palladium(II)dichloromethane complex. The inorganic base is any one or a combination of at least two of sodium carbonate, sodium bicarbonate, potassium carbonate, cesium carbonate, sodium hydroxide, lithium hydroxide, potassium hydroxide, or potassium phosphate. The reaction temperature is greater than or equal to room temperature and less than or equal to the boiling point of the reaction solvent. The reaction time is 2-24 hours.

[0047] The obtained product is prepared according to the above method using general formula I. a The compound method yielded general formula I. c Compounds.

[0048] (iii): Compound of general formula V reacts with compound of general formula VI to give compound of general formula II.

[0049] In this application, the molar ratio of compound V to compound VI is 10.0-1.0, and the reaction is carried out in the presence of an alkaline substance such as an organic base and / or an inorganic base. Preferably, the organic base is any one or a combination of at least two of triethylamine, N,N-diisopropylethylamine, pyridine, 2-methylpyridine, 4-N,N-dimethylaminopyridine (DMAP), 1,8-diazobisspirocyclic [5.4.0]undec-7-ene (DBU), N-methylmorpholine, N-methylpiperidine, N,N-dimethylpiperazine, sodium methoxide, or sodium ethoxide. Preferably, the inorganic base is any one or a combination of at least two of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, or sodium hydride. The reaction temperature is greater than or equal to room temperature and less than or equal to the boiling point of the reaction solvent. The reaction time is 2-48 hours.

[0050] (iv): Compound of general formula II reacts with a halogenating agent to give compound of general formula IV.

[0051] In this application, the molar ratio of the compound of general formula II to the halogenating agent is 0.5-1.0, and the reaction is carried out in the presence of the halogenating agent. Preferably, the halogenating agent is N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS), or N-iodosuccinimide (NIS). The reaction temperature is greater than or equal to room temperature and less than or equal to the boiling point of the reaction solvent. The reaction time is 2-48 hours.

[0052] (v): Compounds of general formula III or general formula V are commercially available or can be prepared by known methods.

[0053] On the other hand, this application provides tautomers, enantiomers, diastereomers or salts thereof of the amide compounds as described above.

[0054] In this application, the tautomers, enantiomers, diastereomers, or salts thereof of the amide compounds can also exert the same effects as the amide compounds, and have good insecticidal effects at low doses.

[0055] On the other hand, this application provides the application of the amide compounds described above in the control of pests and nematodes in the fields of agriculture, forestry and horticulture.

[0056] The amide compounds of this application are suitable for controlling various agricultural, forestry, and horticultural pests, sanitary pests, and nematodes that harm rice, corn, wheat, potatoes, fruit trees, vegetables, other crops, and flowers.

[0057] In this application, the pests include Lepidoptera, Coleoptera, Hemiptera, Thysanoptera, Diptera, Orthoptera, Homoptera, Isoptera, Hymenoptera, spider mites, nematodes, mosquitoes, flies, ants, etc.

[0058] Preferably, the pests include, but are not limited to: cotton bollworm, diamondback moth, beet armyworm, cotton bollworm, cabbage caterpillar, rice stem borer, rice leaf roller, rice thrips, western flower thrips, melon thrips, onion thrips, ginger thrips, mango thrips, peach aphid, cotton aphid, alfalfa aphid, apple aphid, wheat aphid, flea beetle, stink bug, gray planthopper, brown planthopper, white-backed planthopper, termite, mosquito fly, carmine spider mite, and citrus red spider mite.

[0059] The compounds in this application have a wide range of applications, and the plants or ranges to which they are applied mainly include the following categories: rice; fruits and vegetables, such as cucumber, loofah, watermelon, cantaloupe, pumpkin, gourd, spinach, celery, cabbage, Chinese cabbage, gourd, chili pepper, eggplant, tomato, onion, ginger, garlic, leek, lettuce, green beans, cowpeas, broad beans, radish, carrot, potato, and yam; cereals, such as wheat, barley, corn, rice, and sorghum; fruit trees, such as apple, pear, banana, citrus, grape, lychee, and mango; flowers, such as peony, rose, and flamingo; oil crops, such as peanut, soybean, rapeseed, sunflower, and sesame; sugar crops, such as sugar beet and sugarcane; other crops, such as strawberry, potato, sweet potato, tobacco, and tea; horticulture, forestry, household hygiene, and public health areas, etc. The above-listed plants or ranges do not limit the scope of use of the amide compounds in this application.

[0060] On the other hand, this application provides an insecticide composition comprising an active ingredient and a pesticide-acceptable carrier, wherein the active ingredient is an amide compound as described above.

[0061] The compositions of this application can be applied in the form of a formulation, wherein the compound of general formula I is dissolved or dispersed in a carrier as an active component or formulated to facilitate dispersion when used as an insecticide.

[0062] In this application, the insecticide composition may be formulated into wettable powder, suspension, water-in-oil emulsion or emulsifiable concentrate, etc.

[0063] The insecticide composition described in this application can be used in agriculture, forestry, health and other fields.

[0064] Preferably, the active ingredient in the insecticide composition has a weight percentage of 1-99%, for example, 1%, 10%, 20%, 35%, 55%, 75%, 95%, or 99%.

[0065] Preferably, the pesticide-acceptable carrier includes a surfactant.

[0066] In this application, the surfactant is an ionic surfactant or a nonionic surfactant.

[0067] The surfactants include emulsifiers, dispersants, or wetting agents. Emulsifiers can be polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty amines, and commercially available emulsifiers (such as 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#, etc.). Dispersants include sodium lignosulfonate, dispersing agents, calcium lignosulfonate, and methylnaphthalenesulfonic acid formaldehyde condensate. Wetting agents include sodium lauryl sulfate, sodium dodecylbenzenesulfonate, and sodium alkylnaphthalenesulfonate.

[0068] Preferably, the pesticide-acceptable carrier includes a solid carrier and / or a liquid carrier.

[0069] Preferably, the solid carrier comprises natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as kaolinite, montmorillonite, and mica; white carbon black, calcium carbonate, and light calcium carbonate; calcium sulfate; limestone; sodium sulfate; and amine salts such as ammonium sulfate and hexamethylethylenediamine. The liquid carrier comprises water and organic solvents, which can also be used as auxiliaries or antifreeze additives when water is used as a solvent or diluent. Suitable organic solvents include aromatic hydrocarbons such as xylene and toluene; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, chloroform, and dichloromethane; aliphatic hydrocarbons such as petroleum fractions, cyclohexane, and light mineral oils; alcohols such as isopropanol, butanol, ethylene glycol, glycerol, and cyclohexanol; their ethers and esters; and ketones such as acetone, cyclohexanone, dimethylformamide, and N-methylpyrrolidone.

[0070] In the formulation of insecticide compositions, the active ingredients can be mixed with liquid and / or solid carriers, and surfactants (such as emulsifiers, dispersants, stabilizers, and wetting agents) can be added. Other adjuvants (such as binders, defoamers, and oxidants) can also be added.

[0071] On the other hand, this application provides a method for controlling pests, the method being: applying an effective dose of the amide compound or insecticide composition as described above to the pest that needs to be controlled or its growth medium.

[0072] Preferably, the effective dose is 7.5-1000g per hectare, such as 7.5g, 50g, 100g, 180g, 250g, 350g, 450g, 600g, 800g or 1000g, and more preferably 15-600g per hectare.

[0073] The compositions of this application can be applied to pests or their growth media in formulation form. Compound I of general formula is dissolved or dispersed in a carrier or formulated as an active ingredient for easier dispersion when used as an insecticide. For example, these chemical formulations can be formulated into various liquids, emulsifiable concentrates, suspensions, aqueous suspensions, microemulsions, emulsions, water-in-oil emulsions, powders, wettable powders, soluble powders, granules, water-dispersible granules, or capsules.

[0074] For certain applications, such as in agriculture, one or more other insecticides, fungicides, herbicides, plant growth regulators or fertilizers may be added to the insecticidal composition of this application, thereby producing additional advantages and effects.

[0075] Compared with the prior art, this application has the following advantages:

[0076] The amide compounds of this application have significant insecticidal effects on the control of pests and diseases in agriculture and forestry. At low concentrations, i.e., 100 ppm and below, they can achieve ≥73% insecticidal activity within 3 days, thereby effectively reducing the harm to plants, the environment and humans caused by excessive drug concentrations. They also result in less drug residues during application, which is more conducive to environmental protection and ecological civilization. Detailed Implementation

[0077] The technical solution of this application will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of this application and should not be considered as specific limitations thereof. Unless otherwise specified, in the embodiments and this application, the corresponding samples for characterizing the compounds by 1H NMR spectroscopy were dissolved in deuterated dimethyl sulfoxide (DMSO-d6) or deuterated chloroform (CDCl3), and 1H NMR data were obtained using a 400MHz NMR spectrometer. The chemical shift unit is ppm (i.e., δ:ppm). The eluent used for column chromatography purification was prepared according to the indicated volume ratio of petroleum ether (PE): ethyl acetate (EA).

[0078] Synthesis Examples

[0079] Preparation of Compound 1 in Example 1

[0080] (1) Synthesis of 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0081] In a solution of 2-(6-chloro-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (2.00 g, 4.89 mmol, synthesized according to literature CN106103433B) and N-methylpyrrolidone (15 mL), 25%-30% ammonia (3 mL) was added, and the mixture was refluxed for 4 hours. Then, water (100 mL) and ethyl acetate (100 mL) were added, respectively, and the mixture was extracted and separated. The organic layer was washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 1.70 g of pale yellow solid target intermediate, with a yield of 89%.

[0082] According to the above method, the intermediate 2-(6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine was synthesized by replacing the 25%-30% ammonia water in the above reaction with 40% methylamine aqueous solution (2 mL), yielding 1.60 g of pale yellow solid, with a yield of 81%.

[0083] (2) Preparation of compound 1

[0084] In a toluene (5 mL) solution of 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (270.60 mg, 0.70 mmol), N,N-diisopropylethylamine (193.21 mg, 1.48 mmol) and propionyl chloride (98.13 mg, 1.05 mmol) were added sequentially. After reflux for 4 hours, water (10 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 290.60 mg of white solid compound 1, with a yield of 92%.

[0085] Compound 1 1 H NMR (DMSO-d6, δ [ppm]): 11.27 (s, 1H), 8.90 (d, J = 1.2Hz, 1H), 8.69 (d, J = 1.6Hz, 1H), 8.55 (d, J = 9.2Hz, 1H), 8.49 (d, J=9.2Hz,1H),3.79(s,3H),3.67(q,J=7.2Hz,2H),2.50–2.45(m,2H),1.18(t,J=7.2Hz,3H),1.09(t,J=7.6Hz,3H).

[0086] Preparation of Compound 45 in Synthetic Example 2

[0087] In a solution of 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200.04 mg, 0.51 mmol) in acetonitrile (10 mL), potassium iodide (34.46 mg, 0.21 mmol) and monomethyl oxaloyl chloride (76.72 mg, 0.62 mmol) were added. After stirring at 90 °C for 2 hours, water (20 mL) and ethyl acetate (20 mL) were added to the reaction solution, respectively. The mixture was extracted, separated, and the organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 2:1) to give 120.00 mg of white solid compound 45, yield 49%.

[0088] Compound 45 1 H NMR(DMSO-d6,δ[ppm]):11.78(s,1H),8.91(d,J=1.2Hz,1H),8.71(d,J=1.6Hz,1 H),8.59(d,J=8.8Hz,1H),8.40(s,1H),3.98–3.61(m,8H),1.21(t,J=7.2Hz,3H).

[0089] Preparation of compound 47 in Example 3

[0090] In a solution of 5-(ethylsulfonyl)-6-(3-methyl-6-(trifluoromethyl)-3H-imidazol[4,5-b]pyridin-2-yl)pyridin-2-methylamine (218.00 mg, 0.54 mmol) in toluene (3 mL), N,N-diisopropylethylamine (161.88 mg, 1.24 mmol) and acetyl chloride (87.22 mg, 1.10 mmol) were added sequentially. The mixture was reacted at 100 °C for 5 h. Water (10 mL) and ethyl acetate (20 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 81.00 mg of yellow solid compound 47, with a yield of 34%.

[0091] Compound 47 1H NMR(DMSO-d6,δ[ppm]):8.91(s,1H),8.69(s,1H),8.50(d,J=8.8Hz,1H),8.25(d,J=8.8Hz ,1H),3.84(s,3H),3.79(q,J=7.2Hz,2H),3.48(s,3H),2.36(s,3H),1.23(t,J=7.2Hz,3H).

[0092] Preparation of Compound 66 in Synthetic Example 4

[0093] In a solution of 2-(6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (201.71 mg, 0.50 mmol) in acetonitrile (10 mL), potassium iodide (33.25 mg, 0.20 mmol) and monomethyl oxaloyl chloride (74.25 mg, 0.60 mmol) were added. After stirring at 90 °C for 2 hours, water (20 mL) and ethyl acetate (20 mL) were added to the reaction solution, respectively. The mixture was extracted, separated, and the organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 3:1) to give 110.00 mg of yellow solid compound 66, with a yield of 43%.

[0094] Compound 66 1 H NMR(DMSO-d6,δ[ppm]):8.92(d,J=1.2Hz,1H),8.71(d,J=1.6Hz,1H),8.60(d,J=8.8Hz,1H) ,7.89(d,J=8.8Hz,1H),3.75–3.70(m,5H),3.52(s,3H),3.13(s,3H),1.20(t,J=7.2Hz,3H).

[0095] Preparation of Compound 116 in Synthetic Example 5

[0096] (1) Synthesis of 2-(6-(cyclopropylmethylamino)-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0097] In a toluene (70 mL) solution of 2-(6-chloro-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (7.07 g, 17.29 mmol), N,N-diisopropylethylamine (3.35 g, 25.94 mmol) and cyclopropylmethylamine (2.21 mg, 31.13 mmol) were added sequentially. After reflux for 6 hours, water (100 mL) and ethyl acetate (100 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (25 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 7.00 g of white solid target intermediate, with a yield of 92%.

[0098] (2) Preparation of compound 116

[0099] In a solution of 2-(6-(cyclopropylmethylamino)-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (230.00 mg, 0.52 mmol) in tetrahydrofuran (5 mL), pyridine (83.09 mg, 1.04 mmol) and acetyl chloride (49.95 mg, 0.63 mmol) were added sequentially. After reacting at 100 °C for 5 h, water (10 mL) and ethyl acetate (20 mL) were added, respectively. The mixture was extracted, separated, and the organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 172.50 mg of white solid compound 116, with a yield of 68%.

[0100] Compound 116 1 H NMR(DMSO-d6,δ[ppm]):8.91(d,J=1.2Hz,1H),8.69(d,J=1.6Hz,1H),8.52(d,J=8.8Hz,1H),8.10(d,J=8.8Hz,1H),3.88(d,J =6.8Hz,2H),3.81–3.75(m,5H),2.26(s,3H),1.22(t,J=7.2Hz,3H),1.11–1.03(m,1H),0.41–0.36(m,2H),0.17–0.13(m,2H).

[0101] Preparation of Compound 145 in Synthetic Example 6

[0102] (1) Synthesis of 2-(5-chloro-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0103] In a DMF (5 mL) solution of 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200.00 mg, 0.51 mmol), N-chlorosuccinimide (103.95 mg, 0.77 mmol) was added. After reacting at 60 °C for 4 hours, water (10 mL) and ethyl acetate (50 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 198.81 mg of orange-yellow solid target intermediate, with a yield of 91%.

[0104] According to the above method, N-chlorosuccinimide in the above reaction was replaced with N-bromosuccinimide to synthesize the intermediate 2-(5-bromo-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine, 220.04 mg orange-yellow liquid, yield 92%.

[0105] (2) Preparation of compound 145

[0106] In a THF (5 mL) solution of 2-(5-chloro-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200.03 mg, 0.47 mmol), trifluoroacetic anhydride (149.57 mg, 0.71 mmol) and triethylamine (96.23 mg, 0.94 mmol) were added, respectively. After reacting at room temperature for 4 hours, water (15 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 220.61 mg of black solid compound 145, with a yield of 89%.

[0107] Compound 145 1 H NMR(DMSO-d6,δ[ppm]):12.67(s,1H),8.92(d,J=1.6Hz,1H),8.77(s,1H),8.7 3(d,J=1.6Hz,1H),3.85(s,3H),3.59(q,J=7.2Hz,2H),1.17(t,J=6.8Hz,3H).

[0108] Preparation of Compound 174 in Example 7

[0109] In a toluene (10 mL) solution of 2-(5-chloro-6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (201.57 mg, 0.46 mmol), pyridine (73.51 mg, 0.92 mmol) and 2-methoxyacetyl chloride (75.64 mg, 0.69 mmol) were added sequentially. The mixture was heated under reflux at 100 °C for 5 hours, and the reaction was monitored by TLC until the reactants were completely reacted. Water (10 mL) and ethyl acetate (20 mL) were added to the reaction solution, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA = 1:1) to give 150.00 mg of brown solid compound 174, with a yield of 63%.

[0110] Compound 174 1 H NMR(DMSO-d6,δ[ppm]):8.94–8.89(m,1H),8.73(s,1H),8.72–8.68(m,1H),4.17(s,2H ),3.89(q,J=7.2Hz,2H),3.82(s,3H),3.30(s,3H),3.20(s,3H),1.27(t,J=7.2Hz,3H).

[0111] Preparation of compound 211 in Example 8

[0112] In a toluene (5 mL) solution of 2-(5-chloro-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200.06 mg, 0.47 mmol), N,N-diisopropylethylamine (122.71 mg, 0.94 mmol) and cyclopropionyl chloride (103.17 mg, 0.98 mmol) were added sequentially. After reflux for 4 hours, water (15 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1:1) to give 250.60 mg of brownish-yellow solid compound 211, with a yield of 94%.

[0113] Compound 211 1H NMR(DMSO-d6,δ[ppm]):8.93–8.92(m,1H),8.87(s,1H),8.72(d,J=1.6Hz,1H),3.95(q ,J=7.2Hz,2H),3.81(s,3H),2.23–2.17(m,2H),1.30–1.26(m,3H),1.06–0.99(m,8H).

[0114] Preparation of Compound 253 in Example 9

[0115] In a tetrahydrofuran (5 mL) solution of 2-(5-bromo-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (150.00 mg, 0.32 mmol), 60% sodium hydride (26.01 mg, 0.65 mmol) and acetyl chloride (25.78 mg, 0.33 mmol) were added sequentially. After stirring at room temperature for half an hour, the temperature was raised to 60 °C and reacted for 1 hour. Heating was stopped, the mixture was cooled to room temperature, and acetyl chloride (25.75 mg, 0.32 mmol) was added. The mixture was then reacted at 60 °C for another hour. Water (15 mL) and ethyl acetate (30 mL) were added to the reaction mixture, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 2:1) to give 100.00 mg of yellow liquid compound 253, with a yield of 60%.

[0116] Compound 253 1 H NMR (DMSO-d6, δ [ppm]): 10.69 (s, 1H), 8.94–8.88 (m, 1H), 8.70 (d, J = 8.4Hz, 1H), 8.69 (s, 1H), 3.92–3.84 (m, 5H), 2.18 (s, 3H), 1.26 (t, J = 7.2Hz, 3H).

[0117] Preparation of compound 313 in Synthetic Example 10

[0118] In a toluene (10 mL) solution of 2-(5-bromo-6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (227.00 mg, 0.47 mmol), pyridine (75.90 mg, 0.95 mmol) and acetyl chloride (56.30 mg, 0.71 mmol) were added sequentially. The mixture was heated under reflux at 100 °C for 5 hours, and the reaction was monitored by TLC until the reactants were completely reacted. Water (20 mL) and ethyl acetate (20 mL) were added to the reaction mixture, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA = 1:1) to give 100.00 mg of a yellow solid compound 313, with a yield of 40%.

[0119] Compound 313 1 H NMR(DMSO-d6,δ[ppm]):8.92(d,J=1.2Hz,1H),8.84(s,1H),8.70(d,J=1.6Hz,1H),3 .91(q,J=7.2Hz,2H),3.83(s,3H),3.27(s,3H),2.04(s,3H),1.28(t,J=7.2Hz,3H).

[0120] Preparation of compound 391 in Synthetic Example 11

[0121] In a tetrahydrofuran (5 mL) solution of 2-(5-bromo-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (150.00 mg, 0.32 mmol), 60% sodium hydride (26.01 mg, 0.65 mmol) and benzoyl chloride (95.13 mg, 0.67 mmol) were added sequentially. After stirring at room temperature for half an hour, the mixture was heated to 60 °C and reacted for 2 hours. Then, water (15 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted, separated, and the organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 3:1) to give 120.00 mg of white solid compound 391, with a yield of 55%.

[0122] Compound 391 1H NMR (DMSO-d6, δ [ppm]): 8.99 (s, 1H), 8.89–8.84 (m, 1H), 8.69 (d, J = 1.6Hz, 1H), 7.87–7.80 (m, 4H), 7. 68(t,J=7.2Hz,2H),7.56(t,J=7.6Hz,4H),3.85(q,J=7.2Hz,2H),2.91(s,3H),1.23(t,J=7.2Hz,3H).

[0123] Preparation of compound 414 in Example 12

[0124] (1) Synthesis of 2-(5-iodo-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0125] In a solution of 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (1.51 g, 3.89 mmol) in acetonitrile (50 mL), concentrated sulfuric acid (0.19 g, 1.94 mmol) and N-iodosuccinimide (1.75 g, 7.70 mmol) were added sequentially. After reacting at 30 °C for 8 h, water (50 mL) and ethyl acetate (150 mL) were added, respectively. The mixture was extracted, separated, and the organic layer was washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 2:1) to give 1.53 g of a yellow liquid target intermediate, with a yield of 76%.

[0126] According to the above method, 2-(6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine was substituted with 2-(6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine in the above reaction to synthesize the intermediate 2-(5-iodo-6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine, 1.28 g of yellow solid, yield 62%.

[0127] (2) Preparation of compound 414

[0128] In a toluene (5 mL) solution of 5-(ethylsulfonyl)-3-iodo-6-(3-methyl-6-(trifluoromethyl)-3H-imidazol[4,5-b]pyridin-2-yl)pyridin-2-amine (200.00 mg, 0.39 mmol), pyridine (62.32 mg, 0.78 mmol) and acetyl chloride (30.92 mg, 0.39 mmol) were added sequentially. The mixture was reacted at 100 °C for 2 h. Then, water (10 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1.5:1) to give 152.30 mg of brown solid compound 414, with a yield of 69%.

[0129] Compound 414 1 H NMR (DMSO-d6, δ [ppm]): 10.61 (s, 1H), 8.93–8.88 (m, 1H), 8.82 (s, 1H), 8.72–8.69 (m, 1H), 3.90–3.83 (m, 5H), 2.14 (s, 3H), 1.24 (t, J = 7.6Hz, 3H).

[0130] Preparation of compound 438 in Example 13

[0131] In a toluene (5 mL) solution of 5-(ethylsulfonyl)-3-iodo-6-(3-methyl-6-(trifluoromethyl)-3H-imidazol[4,5-b]pyridin-2-yl)pyridin-2-amine (200.01 mg, 0.39 mmol), N,N-diisopropylethylamine (77.02 mg, 0.59 mmol) and benzoyl chloride (55.38 mg, 0.39 mmol) were added sequentially. The mixture was reacted at 100 °C for 2 h. Then, water (10 mL) and ethyl acetate (30 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1.5:1) to give 198.00 mg of white solid compound 438, with a yield of 81%.

[0132] Compound 438 1 H NMR (DMSO-d6, δ [ppm]): 11.24 (s, 1H), 8.91 (s, 2H), 8.73 (s, 1H), 8.02 (d, J = 7.2Hz, 2H), 7.67 ( t,J=7.2Hz,1H),7.58(t,J=7.6Hz,2H),3.91(q,J=7.2Hz,2H),3.83(s,3H),1.28–1.25(m,3H).

[0133] Preparation of compound 475 in Synthetic Example 14

[0134] In a toluene (5 mL) solution of 2-(5-iodo-6-methylamino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200.03 mg, 0.38 mmol), N,N-diisopropylethylamine (99.22 mg, 0.76 mmol) and acetyl chloride (37.27 mg, 0.47 mmol) were added sequentially. The mixture was reacted at 100 °C for 2 h. Then, water (10 mL) and ethyl acetate (20 mL) were added, respectively. The mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 1.5:1) to give 175.00 mg of brown solid compound 475, with a yield of 80%.

[0135] Compound 475 1 H NMR (DMSO-d6, δ [ppm]): 8.95 (s, 1H), 8.93–8.90 (m, 1H), 8.71 (d, J = 1.6Hz, 1H), 3. 91(q,J=7.2Hz,2H),3.82(s,3H),3.20(s,3H),1.97(s,3H),1.26(t,J=7.2Hz,3H).

[0136] Preparation of Compound 604 in Synthetic Example 15

[0137] (1) Synthesis of 2-(5-(4-chlorophenyl)-6-amino-3-(ethanesulfonyl)pyridin-2-yl)-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine

[0138] 3-Bromo-5-(ethylsulfonyl)-6-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (1.00 g, 2.15 mmol), 4-chlorophenylboronic acid (404.18 mg, 2.58 mmol), potassium carbonate (595.37 mg, 4.31 mmol), 1,4-dioxane (15 mL), water (3 mL), and ferrocene palladium dichloride (50.00 mg, 0.068 mmol) were added to single-necked flasks, and the mixture was refluxed for 4 h under nitrogen protection. Water (30 mL) and ethyl acetate (30 mL) were added separately, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 4:1) to give 0.95 g of pale yellow solid 3-(4-chlorophenyl)-5-(ethylsulfonyl)-6-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridine-2-amine, with a yield of 89%.

[0139] 1 H NMR(DMSO-d6,δ[ppm]):8.87(d,J=1.6Hz,1H),8.65(d,J=2.0Hz,1H),7.77(s,1H),7 .59(s,4H),7.25(s,2H),3.81(s,3H),3.60(q,J=7.2Hz,2H),1.18(t,J=7.6Hz,3H).

[0140] (2) Preparation of compound 604

[0141] 3-(4-chlorophenyl)-5-(ethylsulfonyl)-6-(3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (300.00 mg, 0.60 mmol), acetyl chloride (142.00 mg, 1.81 mmol), N,N-diisopropylethylamine (233.92 mg, 1.81 mmol), and toluene (5 mL) were added to a single-necked flask and stirred at 130 °C for about 2 hours. Water (50 mL) and ethyl acetate (50 mL) were added separately, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 4:1) to give 0.32 g of a yellow solid compound 604 (yield 91%).

[0142] Compound 604 1H NMR(DMSO-d6,δ[ppm]):8.93(s,1H),8.73(s,1H),8.59(s,1H),7.66(d,J=8.8Hz,2H),7.5 5(d,J=8.8Hz,2H),3.95(q,J=7.6Hz,2H),3.83(s,3H),2.21(s,6H),1.30(t,J=7.6Hz,3H).

[0143] Preparation of Compound 601 in Synthetic Example 16

[0144] Compound 604 (200.00 mg, 0.35 mmol), sodium hydroxide (28.00 mg, 0.70 mmol), tetrahydrofuran (10 mL), and water (0.5 mL) were added to a single-necked flask and stirred at 25 °C for about 1 hour. Water (50 mL) and ethyl acetate (50 mL) were added separately, and the mixture was extracted and separated. The organic layer was washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA = 3:1) to give 0.14 g of a yellow solid, compound 601, in 75% yield.

[0145] Compound 601 1 H NMR(DMSO-d6,δ[ppm]):10.71(s,1H),8.91(d,J=1.6Hz,1H),8.71(d,J=1.6Hz,1H),8.32(s,1 H),7.64(d,J=8.8Hz,2H),7.58(d,J=8.8Hz,2H),3.90–3.83(m,5H),1.96(s,3H),1.26(s,3H).

[0146] Other compounds in Table 1 were prepared using similar methods to those described in Synthetic Examples 1-16. Table 2 below lists some representative compounds prepared using these methods. 1 Nuclear magnetic resonance data obtained from H NMR testing.

[0147] Table 2

[0148] Other compounds included in general formula I of this application can also be prepared by referring to the methods in synthetic examples 1-16.

[0149] Formulation Example 1

[0150] In this embodiment, a formulation is prepared using compound 1 of this application as a representative compound, as detailed below:

[0151] 30 parts by weight of Compound 1 of this application, 15 parts by weight of polyoxyethylene styrene phenyl ether, 10 parts by weight of phosphorous acid, and 45 parts by weight of xylene were uniformly mixed to obtain an emulsifiable concentrate of Compound 1 of this application with a concentration of 30%.

[0152] Formulation Example 2

[0153] In this embodiment, a formulation is prepared using compound 1 of this application as a representative compound, as detailed below:

[0154] 20 parts by weight of Compound 1 of this application, 2 parts by weight of sodium dodecyl sulfate, 2 parts by weight of dialkyl sulfosuccinate, 1 part by weight of sodium salt of β-naphthalenesulfonic acid formaldehyde condensate, and 75 parts by weight of diatomaceous earth were uniformly stirred and mixed to obtain a 20% wettable powder of Compound 1 of this application.

[0155] Formulation Example 3

[0156] In this embodiment, a formulation is prepared using compound 1 of this application as a representative compound, as detailed below:

[0157] 30 parts by weight of Compound 1 of this application, 10 parts by weight of ethylene glycol, 6 parts by weight of nonylphenol polyethylene glycol ether, 10 parts by weight of sodium lignosulfonate, 10 parts by weight of carboxymethyl cellulose, 1 part by weight of silicone oil aqueous solution, and water to make up to 100 parts by weight are mixed and ground evenly to obtain a 30% suspension of Compound 1 of this application.

[0158] Bioactivity testing examples

[0159] The compounds obtained above were tested against various pests. Unless otherwise specified, the following examples and this application describe the sample preparation method: 10 mg of the original drug was weighed, dissolved in 1 mL of DMF to prepare a 10,000 ppm stock solution, and diluted with 0.05% Tween-80 water to the required concentration for activity testing. The mortality rate is the mortality rate of pests caused by the compound at the test concentration, calculated as: Mortality rate (%) = Number of dead insects / Total number of insects * 100.

[0160] Bioassay Example 1: Insecticidal activity of the compound against alfalfa aphids

[0161] The activity test was conducted using the immersion method. Single leaves with stems were cut from broad beans and inserted into bottles filled with 20 mL of penicillin water. Four adult aphids were inoculated onto each leaf. After 24 hours, the adult aphids were removed to check the nymph population, and single leaves with more than 15 aphids were selected for the experiment. After 72 hours, single leaves with 3-day-old nymphs were immersed in the pesticide solution for 10 seconds, removed, and air-dried. Each treatment was repeated three times. The leaves were then incubated in an observation room at a temperature of 20–26℃, a light intensity of 14 hL:10 hD, and a humidity of 40–60%. The number of live and dead aphids was investigated three days after the treatment, and the mortality rate was calculated.

[0162] The test results are as follows:

[0163] Compounds 1, 4, 5, 6, 11, 47, 50, 53, 59, 115, 116, 120, 121, 123, 125, 126, 127, 130, 133, 134, 141, 142, 143, 145, 147, 166, 174, 253, 265, 313, 318, 415, 418, 426, 475, 484, and 519 of this application, at a concentration of 400 ppm, showed a mortality rate of ≥80% against alfalfa aphids 3 days after application.

[0164] Compounds 1, 11, 47, 50, 53, 59, 115, 116, 120, 121, 125, 126, 130, 133, 134, 145, 147, 166, 174, 253, 265, 313, 318, 415, 418, 426, 475, 484, and 519, at a concentration of 100 ppm, showed a mortality rate of ≥80% against alfalfa aphids 3 days after application.

[0165] Following the above method, a number of compounds from this application were selected and compared with CK1 to CK8 in parallel tests of their alfalfa aphid-killing activity. The test results are shown in Table 3.

[0166] Table 3 Comparison of the insecticidal activity of the compounds in this application with CK1-CK8 against alfalfa aphids.

[0167] " / " indicates that no test was performed.

[0168] As shown in Table 3, at a concentration of 100 ppm, the compounds of this application, along with the control compounds CK1, CK2, and CK3, exhibited excellent insecticidal activity (>92%) against alfalfa aphids. However, at a lower concentration of 10 ppm, the control compounds CK1–CK8 showed no insecticidal activity or were inactive against alfalfa aphids (0%). In contrast, the compounds of this application not only showed very high insecticidal activity (100%) at a concentration of 100 ppm, but also maintained relatively high insecticidal activity (greater than 73%) even at a lower concentration of 10 ppm.

[0169] Biological testing of the insecticidal activity of the compound against brown planthopper in Example 2

[0170] The activity test was conducted using the rice seedling immersion method. Approximately 6cm long hydroponically grown rice seedlings with roots were immersed in the pesticide solution for 10 seconds, then removed and air-dried on absorbent paper. A 200mL plastic cup was prepared, with a moistened filter paper placed at the bottom for moisture retention. 15–30 third-instar nymphs of the brown planthopper were introduced into the cup. The dried rice seedlings were then placed in the cup, roots in contact with the filter paper, facing downwards. The cup was sealed with plastic wrap, with holes punched in the wrap. Each treatment was repeated three times. The plants were then cultured in an observation room at 20–26℃, with a light intensity of 14 hL:10 hD and humidity of 40–60%. The number of surviving and dead planthoppers was assessed three days after treatment, and the mortality rate was calculated.

[0171] The test results are as follows:

[0172] Compounds 1, 4, 6, 10, 14, 45, 46, 47, 50, 51, 53, 59, 66, 115, 116, 120, 121, 123, 125, 126, 127, 141, and 142, at a concentration of 100 ppm, showed a mortality rate of ≥80% against brown planthoppers 3 days after application.

[0173] Following the above method, a number of compounds from this application and control compounds CK5-CK8 were selected for parallel determination of their insecticidal activity against brown planthoppers. The results are shown in Table 4.

[0174] Table 4 Comparison of the insecticidal activity of the compound of this application with CK5-CK8 against brown planthopper.

[0175] " / " indicates that no test was performed.

[0176] As shown in Table 4, at a concentration of 10 ppm, the control compounds CK5–CK8 showed no insecticidal activity against brown planthoppers (0.00%). However, the compounds of this application not only exhibited high insecticidal activity (>98%) at a concentration of 10 ppm, but also maintained high insecticidal activity (>80%) even at a lower dose of 5 ppm.

[0177] Biological testing of the insecticidal activity of compound 3 against diamondback moth

[0178] The activity test was conducted using the leaf immersion method. Cabbage leaves were punched to create leaf discs with a diameter of 1 cm. The leaf discs were immersed in the pesticide solution for 10 seconds, then removed and air-dried in a cool place before being placed in petri dishes with 4 leaf discs per dish. Moistened filter paper was placed in each petri dish to maintain humidity. Ten third-instar diamondback moths were inoculated into each dish, with each treatment repeated three times. The dishes were incubated in a light incubator at 25℃ with a light intensity of 14 hL:10 hD. Three days after treatment, the insects' reactions and the number of dead insects were assessed, and the mortality rate was calculated.

[0179] The test results are as follows:

[0180] Compounds 209, 361, 414, 420, 426, 436, 475, 519, 521 and 523, at a concentration of 1 ppm, showed a mortality rate of ≥80% against diamondback moth 3 days after application.

[0181] Following the above method, parallel determinations of the insecticidal activity of some compounds of this application and control compounds CK1-CK8 were conducted. The results are shown in Table 5.

[0182] Table 5 Comparison of the insecticidal activity of the compound in this application with CK1-CK8 against diamondback moth.

[0183] As can be seen from Table 5, at a concentration of 1 ppm, the compounds of this application have excellent insecticidal activity against diamondback moth (greater than 85%), while the control compounds CK1 to CK8 have no activity (0.00%).

[0184] Biological testing of the insecticidal activity of compound 4 against armyworms

[0185] The activity test was conducted using the leaf immersion method. Leaves from approximately two-week-old corn seedlings were cut into 6cm segments. The corn leaf segments were immersed in the pesticide solution for 10 seconds, then removed and air-dried in a cool, shaded place. Six leaf segments were then placed in each petri dish, with moistened filter paper placed inside to maintain humidity. Ten third-instar armyworm larvae were introduced into each dish, with each treatment repeated three times. The dishes were then incubated in a light incubator at 25℃ with a light intensity of 14 hL:10 h. Three days after treatment, the insects' reactions and the number of dead insects were assessed, and the mortality rate was calculated.

[0186] The test results are as follows:

[0187] Compounds 145, 147, 163, 209, 211, 253, 265, 274, 359, 361, 391, 414, 415, 418, 420, 426, 436, 438, 484, 519, 521, 523, 524, 525, 526, 527, 537, 539, 553, 555, 608, 609, 611, 619, 623, 631, 632, 633, 634, 635, 637, 638, 639, 640, 641, and 642 of this application, at a concentration of 1 ppm, showed a mortality rate of ≥80% against armyworms 3 days after application.

[0188] Following the above method, a number of compounds from this application and control compounds CK1-CK8 were selected for parallel determination of their insecticidal activity against armyworms. The results are shown in Table 6.

[0189] Table 6 Comparison of the insecticidal activity of the compounds in this application with those of CK1-CK8 against armyworms.

[0190] As can be seen from Table 6, at a concentration of 1 ppm, the compounds of this application have high insecticidal activity (≥90%) against armyworms, while the control compounds CK1 to CK8 have no activity (0.00%).

[0191] This application illustrates the amide compounds, their preparation methods, and applications through the above embodiments. However, this application is not limited to the above embodiments, meaning that this application does not necessarily rely on the above embodiments for implementation. Those skilled in the art should understand that any improvements to this application, equivalent substitutions of raw materials for the products, additions of auxiliary components, and selection of specific methods all fall within the protection and disclosure scope of this application.

Claims

1. An amide compound having the structure shown in Formula I: In Formula I: R is selected from hydrogen, halogen, methyl, cyclopropyl, halogen-substituted methyl, cyano, or phenyl with 1-5 R3 substitutions; in: Each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom; R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, and C1-C3 haloalkylthio-substituted C1-C3 alkyl. Alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, R3-substituted benzyl, C2-C6 alkylacyl, C3-C6 cycloalkylacyl, C1-C6 haloalkylacyl, C3-C6 halocycloalkylacyl, 1-5 R3-substituted benzoyl or 1-4 R3-substituted pyridyl, where R3 is defined as described above; in: R4 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C4 alkyl, C1-C6 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, or C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl. When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above; When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

2. The amide compound according to claim 1, wherein, In equation I, R is selected from hydrogen, halogen, methyl, cyclopropyl, trifluoromethyl, cyano, or phenyl with 1-5 R3 substitutions; Wherein: each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom; R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, and C1-C3 haloalkylthio-substituted C1-C3 alkyl. Alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, R3-substituted benzyl, C2-C6 alkylacyl, C3-C6 cycloalkylacyl, C1-C6 haloalkylacyl, C3-C6 halocycloalkylacyl, 1-5 R3-substituted benzoyl or 1-4 R3-substituted pyridyl, where R3 is defined as described above; in: R4 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C4 alkyl, C1-C6 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, or C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl. When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above; When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

3. The amide compound according to claim 1, wherein, In equation I, R is selected from hydrogen, chlorine, bromine, iodine, cyclopropyl, trifluoromethyl, cyano, or phenyl groups with 1-5 R3 substitutions; Wherein: each R3 is independently selected from hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 haloalkyl-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 haloalkoxy-substituted C1-C4 alkyl, C1-C4 alkylthio-substituted C1-C4 alkyl, C1-C4 haloalkylthio-substituted C1-C4 alkyl, C1-C4 alkylsulfinyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfinyl-substituted C1-C4 alkyl, C1-C4 alkylsulfonyl-substituted C1-C4 alkyl, C1-C4 haloalkylsulfonyl-substituted C1-C4 alkyl, or saturated five- or six-membered heterocyclic groups containing an O atom; R1 is selected from hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-substituted C1-C3 alkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C 1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkyl sulfinyl-substituted C1-C3 alkyl, N-(R4)carbamoylmethylene, C2-C6 alkyl acyl, C3-C6 cycloalkyl acyl, C1-C6 haloalkyl acyl, C3-C6 halocycloalkyl acyl, 1-5 R3-substituted benzoyl groups or 1-4 R3-substituted pyridyl groups, where R3 is defined as described above; in: R4 is selected from hydrogen, C1-C6 alkyl, and C3-C6 cycloalkyl; When R and R1 are not both selected from H, R2 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C3 haloalkyl-substituted C1-C3 alkyl, C1-C3 alkoxy-substituted C1-C3 alkyl, C1-C3 alkylthio-substituted C1-C3 alkyl, C1-C3 alkylsulfinyl-substituted C1-C3 alkyl, C1-C3 alkylsulfonyl-substituted C1-C3 alkyl, C1-C3 haloalkylthio-substituted C1-C3 alkyl, C1-C3 haloalkylsulfinyl-substituted C1-C3 alkyl, C1-C3 haloalkylsulfonyl-substituted C1-C3 alkyl, C1-C6 alkoxyformyl, phenyl with 1-5 R3-substituted or pyridyl with 1-4 R3-substituted, and the definition of R3 is as described above; When both R and R1 are selected from H, R2 is selected from C2-C6 alkyl, C4-C6 cycloalkyl, C2-C6 haloalkyl, C1-C3 haloalkyl substituted with C1-C3 alkyl, C1-C3 alkoxy substituted with C1-C3 alkyl, C1-C3 haloalkylthio substituted with C1-C3 alkyl, C1-C3 haloalkylsulfinyl substituted with C1-C3 alkyl, C1-C3 haloalkylsulfonyl substituted with C1-C3 alkyl, 1-5 R3-substituted phenyl or 1-4 R3-substituted pyridyl, and R3 is defined as described above.

4. The amide compound according to any one of claims 1-3, wherein, The amide compound is selected from any one of the following compounds:

5. Tautomers, enantiomers, diastereomers, or salts thereof of the amide compounds according to any one of claims 1-4.

6. The use of the amide compound according to any one of claims 1-4 or the tautomer, enantiomer, diastereomer or salt thereof of the amide compound according to claim 5 in the control of plant pests.

7. An insecticide composition comprising an active ingredient and a pesticide-acceptable carrier, said active ingredient being an amide compound as described in any one of claims 1-4 or a tautomer, enantiomer, diastereomer, or salt thereof of an amide compound as described in claim 5.

8. The insecticide composition according to claim 7, wherein, The insecticide composition contains 0.1-99% by weight of the active ingredient.

9. An insecticide composition comprising a mixture of an amide compound as described in any one of claims 1-4 and other active compounds, wherein the other active compounds are selected from one or more of insecticides, nematicides, acaricides, fungicides, plant growth regulators, herbicides, disinfectants, and poison baits.

10. A method for controlling agricultural or forestry pests, comprising applying an effective dose of an amide compound as described in any one of claims 1-4, or a tautomer, enantiomer, diastereomer, or salt thereof of an amide compound as described in claim 5, or an insecticidal composition as described in claim 9, to the pest to be controlled or to the medium in which it grows.

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