A cyano-substituted benzamide compound and its application

Abstract

The present invention provides a cyano-substituted benzamide compound and application thereof. The cyano-substituted benzamide compound has a structure shown in Formula I. The cyano-substituted benzamide compound described in the present application can have high insecticidal activity at a low dose, has a good acaricidal effect, has good rapid effectiveness, produces less drug residue during application, is more environmentally friendly, and has broad application prospects.

Description

Technical Field

[0001] The invention belongs to the field of pesticides and relates to a cyano-substituted benzamide compound and application thereof. Background Art

[0002] Mites are a common crop pest, widely distributed around the world, and can harm a variety of crops. Once crops are attacked by mites, the appearance of the crops is damaged at the least, and the serious ones can lead to crop yield reduction or even crop failure. Mites are small, reproduce quickly, have a small range of movement, are highly adaptable, and are prone to drug resistance. They are recognized as a group of harmful organisms that are difficult to control. In crop production such as agriculture and horticulture, the damage caused by pests such as mites is still very significant. Due to the resistance of pests to existing pesticides and the environmental unfriendliness of existing pesticides, there has been a need to develop new pesticides with better activity, lower dosage, and more environmental friendliness.

[0003] The insecticidal activity of cyano-substituted benzamide compounds has been reported, such as CN108586279A discloses compound 286 (KC1), CN109497062A discloses compound 23 (KC2) and its insecticidal activity against pests such as diamondback moth and striped stem borer, and CN102119143A discloses the insecticidal activity of compound 6-1125 (KC3) against pests such as diamondback moth, Spodoptera litura, and housefly, but the invention does not disclose the acaricidal activity of such compounds.

[0004]

[0005] There is still a need to actively develop new insecticides that have high acaricidal activity at low doses to meet the needs of agriculture and forestry. Summary of the invention

[0006] In view of the deficiencies of the prior art, the object of the present invention is to provide a cyano-substituted benzamide compound and its application, wherein the cyano-substituted benzamide compound has a good acaricidal effect at a low dosage and is used in a low dosage, which is more conducive to environmental protection.

[0007] To achieve this object, the present invention adopts the following technical solutions:

[0008] In one aspect, the present invention provides a cyano-substituted benzamide compound, wherein the cyano-substituted benzamide compound has a structure as shown in the following formula I:

[0009]

[0010] in,

[0011] Y 1 Selected from chlorine, bromine, iodine or C 1 -C 6 alkyl;

[0012] Y 2 are selected from chlorine, bromine, iodine, C 1 -C 6 Alkyl or C 1 -C 6 Haloalkyl;

[0013] Y 3 Selected from hydrogen or C 1 -C 6 alkyl;

[0014] R 1 , R 2 are independently selected from hydrogen, fluorine, chlorine, bromine, iodine or C 1 -C 6 Alkyl, where R 1 , R 2 At least one is not hydrogen;

[0015] X 1 , X 2 are independently selected from hydrogen or fluorine, wherein X 1 , X 2 At least one is not hydrogen;

[0016] W 1 and W 2 are independently an oxygen atom or a sulfur atom.

[0017] The cyano-substituted benzamide compounds having the structure shown in Formula I of the present invention can achieve good insecticidal effects at low doses, especially good acaricidal effects. Due to the good effects at low doses, the amount of the agent used is reduced in practical applications, which is more environmentally friendly.

[0018] In the present invention, as a preferred technical solution, in Formula I, Y 1 is selected from chlorine, bromine, iodine or methyl; Y 2 is selected from chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl; Y 3 is selected from hydrogen or methyl.

[0019] In the present invention, as another preferred technical solution, in Formula I, R 1 , R 2 are independently selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, wherein R 1 , R 2 At least one of them is not hydrogen.

[0020] As a further preferred technical solution of the present invention, the cyano-substituted benzamide compound is any one of the compounds shown in Table 1 below having a general formula I, wherein W in Formula I1 and W 2 Selected from oxygen.

[0021] Table 1

[0022]

[0023]

[0024]

[0025] In the present invention, as a further preferred technical solution, in Formula I, in the present invention, as another preferred technical solution, in Formula I, R 1 , R 2 are independently selected from hydrogen, fluorine, chlorine, methyl, ethyl, wherein R 1 , R 2 At least one of them is not hydrogen.

[0026] In the present invention, as a particularly preferred technical solution, the cyano-substituted benzamide compound is any one selected from the following compounds:

[0027]

[0028]

[0029]

[0030] The alkyl group described in the present invention refers to a straight chain or branched chain, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and the like. A haloalkyl group refers to a group in which an alkyl group is substituted by one or more halogen atoms, such as trifluoromethyl and difluoromethyl.

[0031] The term "C 1 -C 6 "Alkyl" refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms, including but not limited to methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. "C 1 -C 6 The term "haloalkyl" refers to a straight or branched alkyl group having 1 to 6 carbon atoms substituted with a halogen atom, including but not limited to trifluoromethyl, difluoromethyl, 1,1,1-trifluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, and the like.

[0032] In the present invention, the C 1 -C 6The number of carbon atoms in the group is represented by C1-C6, for example, C1-C6 represents a group having 1, 2, 3, 4, 5 or 6 carbon atoms. 3 -C 6 It indicates that the number of carbon atoms can be 3, 4, 5 or 6, and so on.

[0033] In the present invention, it should be noted that "i-" represents iso, "s-" represents secondary, "t-" represents tertiary, "H" represents a hydrogen atom, "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "I" represents an iodine atom, "CN" represents a cyano group, "Me" represents a methyl group, and "CF" represents a tertiary group. 2 H" is difluoromethyl, "CF 3 " " is trifluoromethyl, "Me" is methyl, "Et" is ethyl, "n-Pr" is n-propyl, "i-Pr" is n-propyl, "n-Bu" is n-butyl, "i-Bu" is isobutyl, and "t-Bu" is tert-butyl.

[0034] The compounds of the general formula I of the present invention can be prepared by the following method. Unless otherwise specified, the groups in the reaction formula are as defined above.

[0035] Preparation method 1:

[0036] The structure of the compound of general formula I of the present invention is as follows, and it can be prepared by the following method:

[0037]

[0038] Wherein LG is selected from fluorine, chlorine, bromine, C 1 -C 12 Alkoxy, C 1 -C 12 Alkyl acyloxy or C 1 -C 12 Alkoxyacyloxy; Hal is selected from fluorine, chlorine, bromine or iodine; R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , W 1 , W 2 The limitations are the same as above.

[0039] 1-(i): The compound of formula III and the compound of formula IV are subjected to reductive amination reaction to obtain the compound of formula V.

[0040] Preferably, the molar ratio of the compound of formula III to the compound of formula IV is 0.5-2:1, for example 0.5:1, 0.8:1, 1:1, 1.2:1, 1.4:1, 1.5:1, 1.8:1 or 2:1.

[0041] In the present invention, the reaction in step 1-(i) is carried out in the presence of an acidic substance and a reducing agent, and the acidic substance is an organic acid and / or an inorganic acid.

[0042] As the reduction reaction, there can be mentioned a method utilizing a hydrogenation reaction and a method utilizing a metal compound (eg, stannous chloride) or a metal (zinc powder, iron powder, etc.).

[0043] The method utilizing the hydrogenation reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere. The catalyst in the hydrogenation reaction may be a palladium catalyst such as palladium-carbon, a cobalt catalyst, a ruthenium catalyst, a platinum catalyst, etc. The solvent may be an alcohol such as methanol and ethanol; an aromatic hydrocarbon such as benzene and toluene; a chain or cyclic ether such as diethyl ether and tetrahydrofuran; or an ester such as ethyl acetate.

[0044] Preferably, the pressure of the hydrogenation reaction is 0.1-10 MPa, for example, 0.1 MPa, 0.5 MPa, 1 MPa, 2 MPa, 3 MPa, 5 MPa or 10 MPa.

[0045] Preferably, the temperature of the hydrogenation reaction is greater than or equal to -20°C and less than or equal to the boiling point of the reaction solvent, for example -20°C, -5°C, 0°C, 10°C, 35°C, 50°C, 70°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0046] Preferably, the hydrogenation reaction time is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 5 hours, 8 hours, 20 hours, 35 hours or 48 hours.

[0047] Preferably, the method using a metal compound or a metal is carried out in any one of methanol, ethanol or ethyl acetate or a mixed solvent of at least two of them.

[0048] Preferably, the metal compound is stannous chloride, and the metal is zinc powder or iron powder, or a combination of at least two of them.

[0049] Preferably, the reaction temperature of the method utilizing a metal compound or metal is greater than or equal to -10°C and less than or equal to the boiling point of the reaction solvent, for example, -10°C, 0°C, 10°C, 25°C, 35°C, 50°C, 70°C, 80°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0050] Preferably, the reaction time of the method using a metal compound or a metal is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 8 hours, 20 hours, 40 hours or 48 hours.

[0051] Preferably, the organic acid is any one of acetic acid, trifluoroacetic acid or formic acid, or a combination of at least two of them.

[0052] Preferably, the inorganic acid is any one of hydrochloric acid, hydrobromic acid, and nitric acid, or a combination of at least two of them.

[0053] Preferably, the reaction temperature in step 1-(i) is greater than or equal to room temperature and less than or equal to the boiling point of the reaction solvent, for example, 25°C, 35°C, 40°C, 60°C, 70°C, 80°C, 90°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0054] Preferably, the reaction time of step 1-(i) is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 5 hours, 10 hours, 15 hours, 20 hours, 30 hours, 33 hours or 48 hours.

[0055] 1-(ii): The compound of formula V reacts with the compound of formula VI to obtain the compound of formula VII.

[0056] Preferably, the molar ratio of the compound of formula V to the compound of formula VI is 0.5-2:1, for example 0.5:1, 1:1, 1.2:1, 1.6:1, 1.8:1 or 2:1.

[0057] In the present invention, the reaction in step 1-(ii) is carried out in the presence of a basic substance, and the basic substance is an organic base and / or an inorganic base.

[0058] Preferably, the organic base is any one of triethylamine, N,N-diisopropylethylamine, pyridine, sodium carbonate, potassium carbonate, sodium methoxide, or potassium tert-butoxide, or a combination of at least two thereof.

[0059] Preferably, the inorganic base is any one of sodium hydroxide, potassium hydroxide or sodium hydride, or a combination of at least two of them.

[0060] Preferably, the solvent for the reaction in step 1-(ii) is selected from any one of dichloromethane, chloroform, toluene, ethyl acetate, acetonitrile, tetrahydrofuran, dioxane, N,N-dimethylformamide, dimethyl sulfoxide or hexamethylphosphoric acid triamide, or a combination of at least two thereof.

[0061] Preferably, the reaction temperature in step 1-(ii) is greater than or equal to -10°C and less than or equal to the boiling point of the reaction solvent, for example -10°C, 0°C, 10°C, 20°C, 40°C, 50°C, 60°C80°C, 90°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0062] Preferably, the reaction time of step 1-(ii) is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 5 hours, 10 hours, 15 hours, 20 hours, 30 hours, 40 hours or 48 hours.

[0063] 1-(iii): The compound of formula VII is hydrolyzed to obtain the compound of formula VIII.

[0064] The hydrolysis in step 1-(iii) is carried out in any one of water, methanol, ethanol, tetrahydrofuran or dioxane, or a mixed solvent of at least two of them.

[0065] Preferably, the hydrolysis in step 1-(iii) is carried out in the presence of an alkaline substance, and the alkaline substance is preferably lithium hydroxide, sodium hydroxide or potassium hydroxide.

[0066] Preferably, the amount of the alkaline substance used is 1-5 times the molar amount of the compound of formula VII, for example, 1 time, 1.5 times, 2 times, 2.5 times, 3 times, 4 times or 5 times.

[0067] 1-(iv): The compound of formula VIII is subjected to substitution reaction to obtain the compound of formula II.

[0068] In this step, the compound of formula VIII is reacted with a compound containing a LG group such as thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, triphosgene, phosphorus tribromide or isopropyl chloroformate using a known method to prepare a compound represented by formula II.

[0069] 1-(v): The compound of formula II reacts with the compound of formula IX to obtain the compound of formula I

[0070] Preferably, the molar ratio of the compound of formula II to the compound of formula IX is 0.5-2:1, such as 0.5:1, 1:1, 1.2:1, or 2:1.

[0071] In the present invention, the reaction in step 1-(v) is carried out in the presence of a basic substance, and the basic substance is an organic base and / or an inorganic base.

[0072] Preferably, the organic base is any one of trimethylamine, triethylamine, diisopropylethylamine, pyridine, 4-N,N-dimethylaminopyridine, and alkali metal alcoholate, or a combination of at least two thereof.

[0073] Preferably, the alkali metal alcoholate is sodium methoxide and / or sodium ethoxide.

[0074] Preferably, the inorganic base is any one of alkali metal hydroxides and carbonates, or a combination of at least two of them.

[0075] Preferably, the alkali metal hydroxide is any one of lithium hydroxide, sodium hydroxide or potassium hydroxide, or a combination of at least two thereof. Preferably, the carbonate is any one of sodium bicarbonate, sodium carbonate or potassium carbonate, or a combination of at least two thereof.

[0076] Preferably, the solvent for the reaction in step 1-(v) is any one of dichloromethane, toluene, tetrahydrofuran, dioxane, acetic acid, acetonitrile, 1,3-dimethyl-2-imidazolidinone, cyclopentane, dimethyl sulfoxide, and N,N-dimethylformamide, or a combination of at least two thereof.

[0077] Preferably, the reaction temperature in step 1-(v) is greater than or equal to -70°C and less than or equal to the boiling point of the reaction solvent, for example, -70°C, -30°C, -5°C, 0°C, 15°C, 30°C, 40°C, 70°C, 90°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0078] Preferably, the reaction time of step 1-(v) is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 5 hours, 10 hours, 15 hours, 30 hours or 48 hours.

[0079] Preparation method 2:

[0080] The compound of general formula I of the present invention can be prepared by another method as follows:

[0081]

[0082] Among them, R 1 , R 2 , Y 1 , Y 2 , Y 3 , X 1 , X 2 , W 1 , W 2 The definitions of , Hal and LG are the same as above.

[0083] 2-(i): Preparation of the compound of general formula XI from the compound of general formula X

[0084] That is, in this step, the compound of the general formula X is reacted with thionyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, triphosgene, phosphorus tribromide or isopropyl chloroformate by a known method to prepare a compound represented by the general formula XI containing a LG group.

[0085] 2-(ii): The compound of formula XI reacts with the compound of formula IX to obtain the compound of formula XII.

[0086] The compound represented by the general formula XI is reacted with the compound represented by the general formula IX under the same conditions as described in 1-(v) to prepare the compound represented by the general formula XII.

[0087] 2-(iii): The compound of formula XII is subjected to reduction reaction to obtain the compound of formula XIII

[0088] The aromatic carboxylic acid amide derivative having a nitro group represented by the general formula XII can be converted into an aromatic carboxylic acid amide derivative having an amine group represented by the general formula XIII through a reduction reaction.

[0089] As the reduction reaction, there can be mentioned a method utilizing a hydrogenation reaction and a method utilizing a metal compound (eg, stannous chloride) or a metal (zinc powder, iron powder, etc.).

[0090] The method utilizing the hydrogenation reaction can be carried out in a suitable solvent, in the presence of a catalyst, at normal pressure or under pressure, in a hydrogen atmosphere. The catalyst in the hydrogenation reaction may be a palladium catalyst such as palladium-carbon, a cobalt catalyst, a ruthenium catalyst, a platinum catalyst, etc. The solvent may be an alcohol such as methanol and ethanol; an aromatic hydrocarbon such as benzene and toluene; a chain or cyclic ether such as diethyl ether and tetrahydrofuran; or an ester such as ethyl acetate.

[0091] Preferably, the pressure of the hydrogenation reaction is 0.1-10 MPa, for example, 0.1 MPa, 0.5 MPa, 1 MPa, 2 MPa, 3 MPa, 5 MPa or 10 MPa.

[0092] Preferably, the temperature of the hydrogenation reaction is greater than or equal to -20°C and less than or equal to the boiling point of the reaction solvent, for example -20°C, -5°C, 0°C, 10°C, 35°C, 50°C, 70°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0093] Preferably, the hydrogenation reaction time is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 5 hours, 8 hours, 20 hours, 35 hours or 48 hours.

[0094] Preferably, the method using a metal compound or a metal is carried out in any one of methanol, ethanol or ethyl acetate or a mixed solvent of at least two of them.

[0095] Preferably, the metal compound is stannous chloride, and the metal is zinc powder or iron powder, or a combination of at least two of them.

[0096] Preferably, the reaction temperature of the method utilizing a metal compound or metal is greater than or equal to -10°C and less than or equal to the boiling point of the reaction solvent, for example, -10°C, 0°C, 10°C, 25°C, 35°C, 50°C, 70°C, 80°C, etc., or the reaction is carried out at the boiling point of the solvent, i.e., under reflux.

[0097] Preferably, the reaction time of the method using a metal compound or a metal is 0.5-48 hours, for example 0.5 hours, 1 hour, 3 hours, 8 hours, 20 hours, 40 hours or 48 hours.

[0098] 2-(iv): The compound of formula XIII reacts with the compound of formula IV to obtain the compound of formula XIV.

[0099] The compound represented by the general formula XIII is reacted with the compound represented by the general formula IV under the same conditions as described in step 1-(i) to produce a compound represented by the general formula XIV.

[0100] 2-(v): The compound of formula XIV reacts with the compound of formula VI to obtain the compound of formula I.

[0101] The compound represented by the general formula XIV is reacted with the compound represented by the general formula VI under the same conditions as described in step 1-(ii) to produce the compound represented by the general formula I.

[0102] On the other hand, the present invention provides an intermediate for preparing the above-mentioned cyano-substituted benzamide compound, which has a structure shown in Formula VIII:

[0103]

[0104] Among them, R 1 , R 2 are independently selected from hydrogen, fluorine, chlorine, bromine, iodine or C 1 -C 6 Alkyl, where R 1 , R 2 At least one is not hydrogen;

[0105] X 1 , X 2 are independently selected from hydrogen or fluorine, wherein X 1 , X 2 At least one is not hydrogen;

[0106] The preparation method of the intermediate compound of formula VIII in the present invention has been mentioned above when describing the preparation method of formula I, and will not be repeated here.

[0107] In the present invention, representative compounds of the intermediate compounds of Formula VIII of the compounds of the present invention are shown in Table 2, but the present invention is not limited thereto.

[0108] Table 2

[0109] No. <![CDATA[R 1 ]]> <![CDATA[R 2 ]]> <![CDATA[W 1 ]]> <![CDATA[W 2 ]]> <![CDATA[X 1 ]]> <![CDATA[X 2 ]]> Characteristics VIII1. Me H O O F H Yellow solid VIII2. F H O O F H Yellow solid VIII3. Cl H O O F H Yellow solid VIII4. E H O O F H VIII5. H Me O O F H Yellow solid VIII6. H F O O F H Yellow solid

[0110] On the other hand, the present invention provides an intermediate for preparing the above-mentioned cyano-substituted benzamide compound, which has a structure shown in Formula XIV:

[0111]

[0112] In Formula XIV, Y 1 Selected from chlorine, bromine, iodine or C 1 -C 6 Alkyl; Y 2 are selected from chlorine, bromine, iodine, C 1 -C 6 Alkyl or C 1 -C 6 Haloalkyl; Y 3 Selected from hydrogen or C 1 -C 6 Alkyl; X 1 , X 2 are independently selected from hydrogen or fluorine, wherein X 1 , X 2 At least one of them is not hydrogen.

[0113] In the present invention, representative compounds of the intermediate compounds of Formula VIII of the compounds of the present invention are shown in Table 3, but the present invention is not limited thereto.

[0114] Table 3

[0115]

[0116]

[0117] In another aspect, the present invention provides tautomers, enantiomers, diastereomers or salts thereof of the cyano-substituted benzamide compounds described above.

[0118] In the present invention, the tautomers, enantiomers, diastereomers or salts thereof of the cyano-substituted benzamide compounds can also exert the same effects as the cyano-substituted benzamide compounds, have good insecticidal effects at low doses, have good acaricidal effects, and have good rapid effectiveness.

[0119] On the other hand, the present invention provides the use of the cyano-substituted benzamide compounds described above in the prevention and control of insect pests and nematodes in the fields of agriculture, forestry, horticulture and health.

[0120] The cyano-substituted benzamide compounds of the present invention are suitable for preventing and controlling various agricultural, forestry and horticultural insect pests, sanitary pests and nematodes that harm rice, corn, wheat, potatoes, fruit trees, vegetables, other crops and flowers.

[0121] In the present invention, the pests include Lepidoptera, Coleoptera, Hemiptera, Thysanoptera, Diptera, Orthoptera, Homoptera, Isoptera, Hymenoptera, spider mite pests and nematodes, mosquitoes, flies, ants and the like.

[0122] Preferably, the pests include but are not limited to: cotton bollworm, diamondback moth, beet armyworm, Spodoptera litura, cabbage worm, striped stem borer, yellow stem borer, semen inferens, fall armyworm, rice leaf roller, rice thrips, western flower thrips, melon thrips, onion thrips, ginger thrips, mango thrips, peach aphid, cotton aphid, alfalfa aphid, apple yellow aphid, wheat aphid, flea beetle, stink bug, gray planthopper, brown planthopper, white-backed planthopper, termite, mosquito fly, cinnabar spider mite, two-spotted spider mite, citrus red spider, tea yellow mite.

[0123] The compounds of the present invention have a wide range of applications, and the plants or ranges used mainly include the following categories: vegetables, including cucumber, loofah, watermelon, melon, pumpkin, hanging melon, spinach, celery, cabbage, cabbage, gourd, pepper, eggplant, tomato, onion, ginger, garlic, leek, lettuce, kidney bean, cowpea, broad bean, radish, carrot, potato, and yam; cereals, including wheat, barley, corn, rice, and sorghum; fruit trees, including apple, pear, banana, citrus, grape, litchi, and mango; flowers, including peony, rose, and flamingo; oil crops, including peanut, soybean, rapeseed, sunflower, and sesame; sugar crops, including beet and sugarcane; other crops, such as strawberry, potato, sweet potato, tobacco, and tea; gardening, forestry, household hygiene, and public health areas, etc.; the plants or ranges listed above have no limiting effect on the scope of use of the cyano-substituted benzamide compounds of the present invention.

[0124] On the other hand, the present invention provides an insecticide composition, which comprises an active component and an agrochemically acceptable carrier, wherein the active component is the cyano-substituted benzamide compound as described above.

[0125] The composition of the present invention 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 ingredient or formulated into a formulation so as to be more easily dispersed when used as an insecticide.

[0126] In the present invention, the insecticide composition can be prepared into formulations such as wettable powder, suspension, aqueous emulsion or emulsifiable concentrate.

[0127] The insecticide composition of the present invention can be used in agriculture, forestry, health and other fields.

[0128] Preferably, in the insecticide composition, the weight percentage of the active ingredient is 1-99%, for example 1%, 3%, 5%, 8%, 10%, 15%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 99%.

[0129] Preferably, the pesticidally acceptable carrier comprises a surfactant.

[0130] In the present invention, the surfactant is an ionic surfactant or a nonionic surfactant.

[0131] The surfactant includes an emulsifier, a dispersant or a wetting agent. The emulsifier can be polyoxyethylene fatty acid ester, polyoxyethylene fatty alcohol ether, polyoxyethylene fatty amine and commercially available emulsifiers (Nongru 2201B, Nongru 0203B, Nongru 100#, Nongru 500#, Nongru 600#, Nongru 600-2#, Nongru 1601, Nongru 2201, Nongru NP-10, Nongru NP-15, Nongru 507#, Nongru OX-635, Nongru OX-622, Nongru OX-653, Nongru OX-667, Ningru 36#, etc.). Dispersants include sodium lignin sulfonate, pull-open powder, calcium lignin sulfonate, methyl naphthalene sulfonic acid formaldehyde condensate, etc. Wetting agents include sodium lauryl sulfate, sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate, etc.

[0132] Preferably, the pesticide-acceptable carrier comprises a solid carrier and / or a liquid carrier.

[0133] Preferably, the solid carrier includes natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates such as talc; magnesium aluminum silicates such as kaolinite, kaolin, montmorillonite and mica; white carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; amine salts such as ammonium sulfate and hexamethylenediamine. Liquid carriers include water and organic solvents. When water is used as a solvent or diluent, organic solvents can also be used as adjuvants or antifreeze additives. Suitable organic solvents include aromatic hydrocarbons such as benzene, xylene, toluene, etc.; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, chloroform, dichloromethane, etc.; aliphatic hydrocarbons such as petroleum fractions, cyclohexane, light mineral oil; alcohols such as isopropanol, butanol, ethylene glycol, glycerol and cyclohexanol, etc.; and their ethers and esters; and ketones such as acetone, cyclohexanone, dimethylformamide and N-methylpyrrolidone.

[0134] In the preparation process of the insecticide composition, the active ingredients can be mixed with liquid carriers and / or solid carriers, and surfactants (such as emulsifiers, dispersants, stabilizers, wetting agents) can be added at the same time. Other auxiliary agents (such as adhesives, defoaming agents, oxidants, etc.) can also be added.

[0135] In another aspect, the present invention provides a method for controlling pests, comprising: applying an effective dose of the cyano-substituted benzamide compound or the insecticide composition as described above to the pests to be controlled or to the medium in which they grow.

[0136] Preferably, the effective dose is 10-1000g per hectare, for example 10g, 20g, 50g, 80g, 100g, 120g, 150g, 180g, 200g, 250g, 300g, 350g, 400g, 450g, 500g, 600g, 700g, 800g, 900g or 1000g, preferably 20-500g per hectare.

[0137] The composition of the present invention can be applied to pests or their growth medium in the form of a preparation. The general formula compound I is dissolved or dispersed in a carrier as an active ingredient or formulated into a preparation so that it is easier to disperse when used as an insecticide. For example, these chemical preparations can be formulated into various liquids, emulsifiable concentrates, suspensions, aqueous suspensions, microemulsions, emulsions, aqueous emulsions, powders, wettable powders, soluble powders, granules, water-dispersible granules or capsules.

[0138] For certain applications, such as in agriculture, one or more other pesticides, fungicides, herbicides, plant growth regulators or fertilizers may be added to the pesticidal composition of the present invention, thereby producing additional advantages and effects.

[0139] Compared with the prior art, the present invention has the following beneficial effects:

[0140] The cyano-substituted benzamide compounds of the present invention have significant effects on preventing and controlling pests and diseases in agriculture and forestry, nematodes and pests in the field of health, and can achieve good insecticidal effects at low doses, with rapid onset of action, and can exert insecticidal activity one day after application, and can achieve very high insecticidal activity within three days, and have good acaricidal effects and good rapidity, and can be applied at low doses, thereby reducing the damage to plants and humans caused by excessive drug concentrations, and generating less drug residues during application, which is more environmentally friendly, and the preparation method thereof is simple and efficient, easy to mass-produce, and has broad application prospects. DETAILED DESCRIPTION

[0141] The technical scheme of the present invention is further described below by specific implementation methods. Those skilled in the art should understand that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention. Unless otherwise specified in the embodiments and the present invention: when the compounds are characterized by nuclear magnetic resonance hydrogen spectrum test, the corresponding samples are dissolved in deuterated dimethyl sulfoxide (DMSO-d 6 ), a 400MHz nuclear magnetic resonance instrument was used to test and obtain hydrogen spectrum data, and the chemical shift unit was ppm (i.e., δ: ppm); the eluent used for column chromatography purification was prepared according to the volume ratio of petroleum ether (abbreviated as PE): ethyl acetate (abbreviated as EA) as shown. The mass spectrometry analysis conditions are as follows, where TFA represents trifluoroacetic acid and MeCN represents acetonitrile:

[0142] Instrument and model: AB Sciex, 4500QTRAP

[0143] Ionization mode: ESI

[0144] Chromatographic column: Quasar C 18, 100*3.0mm, 3.0μm

[0145] Flow rate: 0.5mL / min

[0146] Mobile phase: time / min <![CDATA[H 2 O with TFA 0.1%]]> ACN% 0 70 30 2 70 30 12 10 90 15 10 90 15.1 70 30 20 70 30

[0147] Synthesis Example

[0148] Synthesis Example 1

[0149] Preparation of N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-2-fluorobenzamide (Compound No. 1):

[0150] (1) Synthesis of methyl 2-fluoro-[3-(cyclopropylmethyl)amino]benzoate

[0151]

[0152] To the reaction flask, methyl 2-fluoro-3-aminobenzoate (8.5 g, 50.0 mmol), 50 mL of ethyl acetate, cyclopropylcarboxaldehyde (3.5 g, 50.0 mmol) and zinc powder (6.5 g, 100.0 mmol) were added in sequence. The temperature was raised to 60°C, and glacial acetic acid (12.0 g, 200.0 mmol) was added dropwise. The reaction was stopped after 6 hours. After the reaction solution was cooled to room temperature, water (50 mL) was added to the reaction solution for separation and extraction. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE: EA = 97: 3) to give a colorless liquid product, methyl 2-fluoro-[3-(cyclopropylmethyl)amino]benzoate (10 g, yield 89.3%).

[0153] (2) Synthesis of methyl 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoate

[0154]

[0155] Add 2-methyl-4-cyanobenzoic acid (1.0 g, 6.2 mmol), toluene (15 mL) and thionyl chloride (3.3 g, 27.5 mmol) to the reaction bottle in sequence, react under reflux for 2 h, concentrate toluene under reduced pressure, and dissolve the concentrated residue in tetrahydrofuran (10 mL) for later use. Dissolve methyl 2-fluoro-[3-(cyclopropylmethyl)amino]benzoate (1.2 g, 5.4 mmol) in tetrahydrofuran (10 mL), add pyridine (0.5 g, 6.3 mmol), dropwise add the tetrahydrofuran solution of acyl chloride obtained in the first step, and stir at room temperature for 4 h. Ethyl acetate (30 mL) was added to the reaction solution for dissolution, and the organic layer was washed with 2 M hydrochloric acid and saturated sodium bicarbonate in sequence, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE: EA = 3: 1) to give a yellow liquid product, 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoic acid methyl ester (1.4 g, yield 70.7%).

[0156] (3) Synthesis of 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoic acid

[0157]

[0158] Methyl 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoate (1.4 g, 3.8 mmol) was dissolved in methanol (8 mL), 10% aqueous sodium hydroxide solution (7 mL) was added, and the mixture was stirred at room temperature for 2 h. The methanol was removed by concentration under reduced pressure. The residue after concentration was dissolved in water (30 mL), and the mixture was extracted with ethyl acetate (20 mL). The organic phase was discarded, and the pH of the aqueous phase was adjusted to 7 with 2M aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoic acid (1.3 g, yield 97.0%) as a yellow solid.

[0159] (4) Synthesis of N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-2-fluorobenzamide

[0160]

[0161] To the reaction flask, 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoic acid (0.7 g, 2.0 mmol), toluene (6 mL), and thionyl chloride (1.65 g, 13.8 mmol) were added in sequence. The mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (3 mL) for later use.

[0162] 2-Bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (0.8 g, 1.96 mmol) was dissolved in tetrahydrofuran (4 mL), and 2.0 M lithium diisopropylamide tetrahydrofuran solution (1.19 mL, 2.39 mmol) was added dropwise at -70°C, and 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoyl chloride tetrahydrofuran solution synthesized in one step was added dropwise after 5 minutes, and the mixture was stirred at -70°C for 30 minutes, and then stirred at room temperature for 30 minutes. The reaction was terminated when the reaction was no longer progressing as monitored by thin layer chromatography. Water (20 mL) was added to the reaction solution, extracted with ethyl acetate (20 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:1), N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamide]-2-fluorobenzamide (0.5 g, yield 34.0%).

[0163] Compound 1 1H NMR (400 MHz, CDCl 3 -d), δ[ppm]: 8.15(d,J=2.0Hz,1H),8.09-7.99(m,2H),7.66-7.59(m,1H),7.52-7.42(m,1H),7.39(s,1H),7.24(d,J=7.6Hz ,1H),7.17(d,J=8.0Hz,1H),3.84(d,J=72.0Hz,2H),2.44(s,3H),1.16-1.02(m,1H),0.62-0.49(m,2H),0.33-0.14(m,2H).

[0164] Synthesis Example 2

[0165] Preparation of N-[2-bromo-6-methyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-2-fluorobenzamide (Compound No. 2):

[0166]

[0167] 2-Bromo-6-methyl-4-heptafluoroisopropylaniline (300 mg, 0.85 mmol), N,N-diisopropylethylamine (1.0 mL) and 4-N,N-dimethylaminopyridine (30 mg) were added to 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoyl chloride (300 mg, 0.81 mmol) in sequence at room temperature, the mixture was reacted at 100°C for 8 h, and the reaction solution was cooled to room temperature. Water (20 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (20 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=5:1). N-[2-bromo-6-methyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]-2-fluorobenzamide (142 mg, yield 25.5%)

[0168] Compound 2 1 H NMR (400 MHz, DMSO-d 6), δ[ppm]: 10.15(s,1H),7.83-7.77(m,2H),7.68-7.58(m,4H),7.48(d,J=8.0Hz,1H),7.31–7.27(m,1H),3.8 7–3.79(m,1H),3.73–3.65(m,1H),2.34(s,6H),1.09–1.00(m,1H),0.46(d,J=8.0Hz,2H),0.20-0.17(m,2H).

[0169] Synthesis Example 3

[0170] Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-2-fluorobenzamide (Compound No. 6):

[0171]

[0172] To the reaction flask, 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoic acid (0.7 g, 2.0 mmol), toluene (6 mL), and thionyl chloride (1.65 g, 13.8 mmol) were added in sequence. The mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (3 mL) for later use.

[0173] Dissolve 2,6-dibromo-4-heptafluoroisopropylaniline (0.82 g, 1.96 mmol) in tetrahydrofuran (4 mL), add 2.0 M lithium diisopropylamide tetrahydrofuran solution (1.19 mL, 2.39 mmol) dropwise at -70°C, and add the tetrahydrofuran solution of 2-fluoro-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]benzoyl chloride synthesized in one step dropwise after 5 minutes, stir at -70°C for 30 minutes, warm to room temperature and continue stirring for 30 minutes. The reaction is terminated when the reaction is no longer progressing as monitored by thin layer chromatography. Water (20 mL) was added to the reaction solution, extracted with ethyl acetate (20 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=3:1), N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamide]-2-fluorobenzamide (0.15 g, yield 9.9%).

[0174] Compound 6 1 H NMR (400 MHz, CDCl 3-d), δ[ppm]: 8.03(t,J=7.6Hz,1H),7.94(t,J=13.2Hz,1H),7.89(s,2H),7.65-7.59(m,1H),7.51-7.41(m,1H),7.39(s,1H) ,7.25-7.23(m,1H),7.18(d,J=8.0Hz,1H),3.96-3.77(m,2H),1.16-1.05(m,1H),0.52(d,J=7.6Hz,2H),0.34-0.23(m,2H).

[0175] Mass spectral data ESI-MS: [M+H] + =752.3, [MH] + =750.1

[0176] Synthesis Example 4

[0177] Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]-2-fluorobenzamide (Compound No. 39):

[0178] (1) Synthesis of methyl 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoate

[0179]

[0180] Add 3-methyl-4-cyanobenzoic acid (1.1 g, 6.8 mmol), toluene (15 mL) and thionyl chloride (4.0 g, 34.0 mmol) to the reaction bottle in sequence, react under reflux for 2 h, concentrate toluene under reduced pressure, and dissolve the concentrated residue in tetrahydrofuran (10 mL) for later use. Dissolve methyl 2-fluoro-3-(N-cyclopropylmethylamino)benzoate (1.5 g, 6.8 mmol) in tetrahydrofuran (10 mL), add pyridine (0.65 g, 8.2 mmol), dropwise add the tetrahydrofuran solution of acyl chloride obtained in the first step, and stir at room temperature for 4 h. Ethyl acetate (30 mL) was added to the reaction solution for dissolution, and the organic layer was washed with 2 M hydrochloric acid and saturated sodium bicarbonate in sequence, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE: EA = 5: 1) to give a yellow liquid product, 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoic acid methyl ester (1.0 g, yield 40.2%).

[0181] (3) Synthesis of 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoic acid

[0182]

[0183] Methyl 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoate (1.0 g, 2.7 mmol) was dissolved in methanol (8 mL), 10% aqueous sodium hydroxide solution (7 mL) was added, and the mixture was stirred at room temperature for 2 h. The methanol was removed by concentration under reduced pressure. The residue after concentration was dissolved in water (30 mL), and the mixture was extracted with ethyl acetate (20 mL). The organic phase was discarded, and the pH of the aqueous phase was adjusted to 7 with 2M aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoic acid (0.9 g, yield 94.7%) as a yellow solid.

[0184] (4) Synthesis of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]-2-fluorobenzamide

[0185]

[0186] To the reaction flask, 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoic acid (0.3 g, 0.85 mmol), toluene (6 mL), and thionyl chloride (1.0 g, 8.5 mmol) were added in sequence. The mixture was refluxed for 2 h and concentrated under reduced pressure to obtain 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoyl chloride.

[0187] N,N-diisopropylethylamine (0.22 g, 1.7 mmol), 4-N,N-dimethylaminopyridine (21 mg, 0.17 mmol) and 2,6-dibromo-4-heptafluoroisopropylaniline (0.35 g, 0.85 mmol) were added to 2-fluoro-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamido]benzoyl chloride in sequence with stirring, and the mixture was reacted at 100°C for 8 h. The reaction solution was cooled to room temperature. Water (20 mL) was added to the reaction solution, extracted with ethyl acetate (20 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=5:1), N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-phenyl]-3-[N-(cyclopropylmethyl)-3-methyl-4-cyanobenzamide]-2-fluorobenzamide (0.22 g, yield 34.9%).

[0188] Compound 39 1H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.49(s,1H),8.04(s,2H),7.75-7.56(m,3H),7.44(br s,1H),7.32(br s,1H),7.21(br s,1H),3.73(s,2H),2.39(s,3H),1.03(br s, 1H), 0.43 (d, J = 8.4Hz, 2H), 0.12 (br s, 2H).

[0189] Synthesis Example 5

[0190] Preparation of N-[2-bromo-6-trifluoromethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide (Compound No. 43):

[0191] (1) Preparation of N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl]-4-fluoro-3-nitrobenzamide

[0192]

[0193] 4-Fluoro-3-nitrobenzoic acid (4.0 g, 21.6 mmol) and 30 mL of toluene were added to a reaction flask, and dichlorothionyl (25.7 g, 0.22 mol) was added. The temperature was raised to reflux for reaction for 2 h. The reaction solution was cooled to room temperature and distilled under reduced pressure to obtain 4-fluoro-3-nitrobenzoyl chloride. 2-Bromo-6-trifluoromethyl-4-heptafluoroisopropylaniline (6.6 g, 16.17 mmol), N,N-diisopropylethylamine (10 mL) and 4-N,N-dimethylaminopyridine (0.4 g) were heated to 120°C for 8 h. The reaction solution was cooled to room temperature, 50 mL of ethyl acetate and 50 mL of water were added, and the mixture was separated and extracted. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=10:1) to obtain N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-nitrobenzamide (3.7 g) as a red solid with a yield of 39.3%.

[0194] 1 H NMR (400 MHz, DMSO-d 6)δ[ppm]: 11.08(s,1H),8.77(dd,J=7.2,2.4Hz,1H),8.47(d,J=2.4Hz,1H),8.4 1(ddd,J=8.8,4.2,2.4Hz,1H),8.03–7.97(m,1H),7.85(dd,J=11.2,8.8Hz,1H).

[0195] (2) Preparation of 3-amino-N-[(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluorobenzamide

[0196]

[0197] N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluoro-3-nitrobenzamide (3.65 g, 6.4 mmol) was dissolved in 30 ml of ethanol, and dihydrated stannous chloride (5.7 g, 25.5 mmol) was added. The mixture was refluxed and monitored by TLC until the reaction was completed. The reaction solution was cooled to room temperature, and the pH value of the reaction solution was adjusted to 12 with a 10% aqueous sodium hydroxide solution, and filtered. The filter cake was rinsed with 30 ml of ethyl acetate, and water (100 mL) was added to the filtrate, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=8:1) to obtain 3-amino-N-[(2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-4-fluorobenzamide (2.95 g) as a red solid with a yield of 84.9%.

[0198] 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.42(s,1H),8.41(d,J=2.4Hz,1H),7.95(d,J=2.4Hz,1H),7.39–7.34(m,1H),7.19–7.12(m,2H),5.47(s,2H).

[0199] (3) Preparation of N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-[(cyclopropylmethyl)amino]-4-fluorobenzamide

[0200]

[0201] 3-Amino-N-[(2-bromo-4-(heptafluoroprop-2-yl)-6-(trifluoromethyl)phenyl]-4-fluorobenzamide (2.95 g, 5.4 mmol) was dissolved in 1,2-dichloroethane, cyclopropanecarboxaldehyde (0.38 g, 5.4 mmol) and acetic acid (0.36 g, 5.94 mmol) were added, and the mixture was reacted at room temperature for 0.5 hour. Then sodium triacetoxyborohydride (1.1 g, 5.4 mmol) was added and the mixture was reacted at room temperature. After the reaction was completed as monitored by TLC, 20 ml of saturated aqueous sodium bicarbonate solution was added, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=10:1) to give N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-[(cyclopropylmethyl)amino]-4-fluorobenzamide (2.36 g) as a white solid with a yield of 72.9%.

[0202] 1 H NMR (400 MHz, DMSO-d 6 )δ10.44(s,1H),8.43(d,J=2.2Hz,1H),7.97(d,J=2.2Hz,1H),7.35–7.29(m,1H),7.23–7.16(m,2H),5.8 0(td,J=6.4,2.0Hz,1H),3.04(t,J=6.4Hz,2H),1.16–1.07(m,1H),0.51–0.45(m,2H),0.31–0.22(m,2H).

[0203] (4) Preparation of N-[2-bromo-6-trifluoromethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide

[0204]

[0205] 2-Methyl-4-cyanobenzoic acid (130 mg, 0.8 mmol) was suspended in 10 ml of toluene, and dichlorothionyl (1.2 g, 10 mmol) was added, and the temperature was raised to reflux for reaction for 2 h. The mixture was evaporated under reduced pressure, and 3 mL of tetrahydrofuran and N-[2-bromo-4-(heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-[(cyclopropylmethyl)amino]-4-fluorobenzamide (300 mg, 0.5 mmol) were added to the obtained residue. The mixture was refluxed and monitored by TLC until the reaction was completed. The reaction solution was cooled to room temperature. Saturated aqueous sodium bicarbonate solution (10 mL) was added to the reaction solution, extracted with ethyl acetate (20 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=5:1) to give N-[2-bromo-6-trifluoromethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide (329 mg) as a yellow solid in a yield of 88.6%.

[0206] Compound 43 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.64(s,1H),8.46(br s,1H),8.05–7.94(m,2H),7.85–7.99(m,3H),7.65(br s,1H),7.53–7.45(m,1H),7.40(t,J=9.2Hz,1H),7.27(d,J=8.0Hz,1H),3.82(d,J=7. 2Hz,1H),3.79(m,2H),2.34(s,3H),0.98-1.09(m,1H),0.45(d,J=8.0Hz,2H),0.17(br s,2H).

[0207] Synthesis Example 6

[0208] Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide (Compound No. 48):

[0209] (1) Synthesis of N-(2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)phenyl)-4-fluoro-3-nitrobenzamide

[0210]

[0211] To the reaction flask, 4-fluoro-3-nitrobenzoic acid (3.31 g, 17.9 mmol), toluene (30 mL), and thionyl chloride (4.26 g, 35.8 mmol) were added in sequence, and the mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure to obtain 4-fluoro-3-nitrobenzoyl chloride.

[0212] KI (0.99 g, 5.95 mmol) and 2,6-dibromo-4-heptafluoroisopropylaniline (5 g, 11.9 mmol) were added to 4-fluoro-3-nitrobenzoyl chloride acetonitrile solution (50 ml) in sequence under stirring, and the mixture was reacted at 80°C for 8 h. The reaction solution was cooled to room temperature. Water (100 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=5:1) to give N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-fluoro-3-nitrobenzamide (5.64 g, yield 80.7%).

[0213] 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 11.03(s,1H),8.80(dd,J=7.2,2.4Hz,1H),8.43(ddd,J=8.8,4.2,2.4Hz,1H),8.07(s,2H),7.85(dd,J=11.2,8.8Hz,1H).

[0214] (2) Synthesis of 3-amino-N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-fluorobenzamide

[0215]

[0216] Dissolve N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)phenyl]-4-fluoro-3-nitrobenzamide (5 g, 8.5 mmol) in anhydrous ethanol (50 ml), add stannous chloride dihydrate (7.7 g, 34.1 mmol) under stirring, react at 78°C for 2 h, cool the reaction solution to room temperature, concentrate under reduced pressure, dissolve the residue in ethyl acetate (150 ml), add Add water (150 ml), adjust the pH value to 12 with sodium hydroxide at 0-30°C, separate the phases, wash the organic layer with saturated brine, dry it with anhydrous sodium sulfate, and concentrate it under reduced pressure. The residue is purified by column chromatography (PE:EA=5:1) to obtain 3-amino-N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-fluorobenzamide (4.06 g, yield 85.6%).

[0217] 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.40(s,1H),8.02(s,2H),7.39(dd,J=8.8,2.2Hz,1H),7.26–7.07(m,2H),5.46(s,2H).

[0218] (3) Synthesis of 3-[(cyclopropylmethyl)amino]-N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-fluorobenzamide

[0219]

[0220] 3-Amino-N-(2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoroprop-2-yl)phenyl)-4-fluorobenzamide (4.00 g, 7.2 mmol), 1,2-dichloroethane (40 ml), acetic acid (2.59 g, 43.2 mmol), cyclopropanecarboxaldehyde (0.51 g, 7.2 mmol) were added to the flask in sequence, and the mixture was reacted at room temperature for 30 minutes. Sodium triacetoxyborohydride (4.58 g, 21.6 mmol) was added in batches. ), react at room temperature for 2h, add water (50ml) to the reaction solution to quench, extract with dichloromethane (50ml), wash the organic layer with saturated brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure. The residue is purified by column chromatography (PE:EA=10:1) to give 3-[(cyclopropylmethyl)amino]-N-(2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl)-4-fluorobenzamide (2.03g, yield 46.3%).

[0221] 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.40(s,1H),8.03(s,2H),7.35(dd,J=8.4,2.0Hz,1H),7.26–7.16(m,2H),5.76(td,J= 5.8, 2.2Hz, 1H), 3.04 (t, J = 6.2Hz, 2H), 1.21–1.00 (m, 1H), 0.54–0.39 (m, 2H), 0.32–0.18 (m, 2H).

[0222] (4) Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide (Compound No. 48):

[0223]

[0224] 2-Methyl-4-cyanobenzoic acid (145 mg, 0.9 mmol) was suspended in 10 ml of toluene, and dichlorothionyl (1.2 g, 10 mmol) was added. The temperature was raised to reflux for reaction for 2 h, and distillation was performed under reduced pressure. To the obtained residue was added 3 mL of toluene, N,N-diisopropylethylamine (1 mL) and 3-[(cyclopropylmethyl)amino]-N-[2,6-dibromo-4-(heptafluoroprop-2-yl)phenyl]-4-fluorobenzamide (400 mg, 0.66 mmol), and the mixture was refluxed for reaction. After the reaction was completed, the reaction solution was cooled to room temperature after monitoring by TLC. Water (20 mL) was added to the reaction solution, extracted with ethyl acetate (20 mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=5:1) to give N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-methyl-4-cyanobenzamido]-4-fluorobenzamide (178 mg) with a yield of 35.8%.

[0225] Compound 48 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.61(s,1H),8.07-8.03(m,3H),7.92-7.86(m,1H),7.67(d,J=1.6Hz 1H),7.50(dd,J=7.8,1.6Hz,1H),7.38(t,J=9.2Hz,1H),7.28(d,J=8.0Hz,1H),3.79(d, J=7.2Hz,2H),2.35(s,3H),1.10–0.98(m,1H),0.45(d,J=8.4Hz,2H),0.38–0.09(m,2H).

[0226] Mass spectral data ESI-MS: [M+H] + =751.98, [MH] + =749.96

[0227] Synthesis Example 7

[0228] Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-ethyl-4-cyanobenzamido]-4-fluorobenzamide (Compound No. 53):

[0229] (1) Synthesis of 4-cyano-2-ethylbenzoic acid

[0230]

[0231] To the reaction flask, methyl 4-amino-2-ethylbenzoate (1.60 g, 8.9 mmol) and 35 wt% H 2 SO 4 (50ml), cooled to 0-5°C in an ice bath under stirring, sodium nitrite aqueous solution (0.86g, 9.34mmol, 10ml water) was added dropwise, reacted at 0-5°C for 1h, KI (1.78g, 10.7mmol) was added, and reacted at 40-50°C for 2h, water (50mL) was added to the reaction solution, and extracted with ethyl acetate (40mL), the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, and the residue was purified by column chromatography (PE:EA=1:0), 4-iodo-2-ethylbenzoic acid methyl ester (2.00g, yield 76.9%).

[0232] To the reaction flask, methyl 4-iodo-2-ethylbenzoate (2.00 g, 6.9 mmol), dimethyl sulfoxide (20 ml), and cuprous cyanide (1.23 g, 13.8 mmol) were added in sequence, and the reaction was carried out at 135-140 ° C for 8 h. The reaction was cooled to room temperature, and 10 wt% ethylenediamine solution (50 mL) was added to the reaction solution. It was extracted with ethyl acetate (100 mL), and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE: EA = 10: 1) to give methyl 4-cyano-2-ethylbenzoate (1.10 g, yield 84.6%).

[0233] To the reaction flask, methyl 4-cyano-2-ethylbenzoate (0.72 g, 3.8 mmol), anhydrous ethanol (30 ml), and 1 M aqueous sodium hydroxide solution (7 ml) were added in sequence, and the mixture was reacted at room temperature for 2 h. Water (50 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (80 mL). The pH value of the aqueous layer was adjusted to 2 with 1 M aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate (80 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 4-cyano-2-ethylbenzoic acid (0.46 g, yield 69.1%).

[0234] Compound 4-cyano-2-ethylbenzoic acid 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 13.45(s,1H),7.88–7.82(m,2H),7.75(dd,J=8.0,1.7Hz,1H),2.92(q,J=7.5Hz,2H),1.17(t,J=7.5Hz,3H).

[0235] (2) N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-ethyl-4-cyanobenzamido]-4-fluorobenzamide

[0236]

[0237] To the reaction flask, 4-cyano-2-ethylbenzoic acid (0.069 g, 0.39 mmol), toluene (5 mL), and thionyl chloride (0.5 g, 4.2 mmol) were added in sequence, and the mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure to obtain 4-cyano-2-ethylbenzoyl chloride.

[0238] 3-[(Cyclopropylmethyl)amino]-N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-fluorobenzamide (0.2 g, 0.33 mmol) was added to a tetrahydrofuran solution of 4-cyano-2-ethylbenzoyl chloride (10 ml) under stirring, and the mixture was reacted at room temperature for 16 h. Water (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (40 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=4:1), and N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-ethyl-4-cyanobenzamido]-4-fluorobenzamide (0.20 g, yield 77.1%) was obtained.

[0239] Compound 53 1 H NMR (400 MHz, DMSO-d 6 )δ[ppm]: 10.59(s,1H),8.06(s,2H),8.03-7.97(m,1H)7.92-7.86(m,1H),7.70(d,J=1.6Hz,1H),7.51(dd,J=8.0,1.6Hz,1H),7.38(t,J=9.2Hz,1 H),7.27(d,J=8.0Hz,1H),3.91–3.59(m,2H),2.73–2.59(m,2H),1.23–1 .17(m,3H),1.07-0.97(m,1H),0.45(d,J=8.0Hz,2H),0.18-0.15(m,2H).

[0240] Synthesis Example 8

[0241] Preparation of N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-ethyl-4-cyanobenzamido]-2-fluorobenzamide (Compound No. 15):

[0242]

[0243] To the reaction flask, 4-cyano-2-ethylbenzoic acid (0.069 g, 0.39 mmol), toluene (5 mL), and thionyl chloride (0.5 g, 4.2 mmol) were added in sequence, and the mixture was refluxed for 2 h. The mixture was concentrated under reduced pressure to obtain 4-cyano-2-ethylbenzoyl chloride.

[0244] 3-[(Cyclopropylmethyl)amino)-N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-2-fluorobenzamide (0.2 g, 0.33 mmol) was added to a tetrahydrofuran solution of 4-cyano-2-ethylbenzoyl chloride (10 ml) under stirring, and the mixture was reacted at room temperature for 16 h. Water (30 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (40 mL). The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EA=4:1), and N-[2,6-dibromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[N-(cyclopropylmethyl)-2-ethyl-4-cyanobenzamido]-4-fluorobenzamide (0.15 g, yield 57.7%) was obtained.

[0245] 1H NMR (400 MHz, DMSO-d6) δ [ppm] of compound 15: 10.51 (s, 1H), 8.04 (s, 2H), 7.88-7.77 (m, 1H), 7.70 (d, J = 1.6 Hz, 1H), 7.68-7.55 (m, 2H), 7.28 (dd, J = 13.2, 7.8 Hz, 2H), 3.68 (s, 2H), 2.66 (q, J = 7.8 Hz, 2H), 1.19 (t, J = 7.8 Hz, 3H), 1.13-0.98 (m, 1H), 0.46 (d, J = 7.8 Hz, 2H), 0.17 (d, J = 5.2 Hz, 2H).

[0246] In addition to the compounds described above, some of the compounds in Table 1 were prepared by methods similar to those in Synthesis Examples 1-7. The following Table 4 gives the NMR data of some of the compounds synthesized by methods similar to those in Synthesis Examples 1-8.

[0247] Table 4

[0248]

[0249]

[0250]

[0251]

[0252] Other compounds of general formula I of the present invention can be synthesized by referring to the above method.

[0253] Formulation Examples

[0254] Preparation Example 1 Preparation of Compound 2 emulsifiable concentrate

[0255] Table 5 Compound 2 EC

[0256] name Fold content (W / W, %) Remark Compound 2 5 Active ingredients Calcium dodecylbenzenesulfonate 5 Emulsifier Castor Oil Polyoxyethylene Ether 5 Emulsifier Trimethylbenzene Make up 100 Solvents

[0257] Preparation method: Calculate the amount of each material according to the formula in Table 5, add trimethylbenzene into a 250mL three-necked flask, add compound 2, calcium dodecylbenzenesulfonate, and castor oil polyoxyethylene ether into the three-necked flask, stir at 40-50°C for 1.5 hours, and filter to obtain 5% compound 2 emulsifiable concentrate.

[0258] Formulation Example 2 Compound 6 Wettable Powder

[0259] Table 6 30% Compound 6 Wettable Powder

[0260] name Fold content (W / W, %) Remark Compound 6 30 Active ingredients Sodium Lauryl Sulfate 1.5 Wetting Agents Sodium lignin sulfonate 6 Dispersants Kaolin Make up 100 Carrier

[0261] Preparation method: Calculate the amount of each material according to the formula in Table 6, mix compound 6, sodium dodecyl sulfate, sodium lignin sulfonate and kaolin evenly, and grind them into an average particle size of 10 microns using a jet mill to obtain a 30% wettable powder of compound 6.

[0262] Biological Activity Test Example

[0263] The compounds of the present invention obtained above were tested on various pests. Unless otherwise specified in the examples and the present invention: the sample preparation method is to weigh 10 mg of the original drug of the sample to be tested, dissolve it with 1 mL of DMF, prepare a 10000 ppm mother solution, and dilute the mother solution with 0.05% Tween-80 water to the required concentration for activity testing. The mortality rate is the mortality rate that causes the death of pests at the test concentration of the compound, and the calculation formula is mortality rate (%) = number of dead insects / total number of insects*100.

[0264] Indoor biological activity of the compound of test example 1 against Tetranychus cinnabarinus

[0265] Cut a single leaf of broad bean with stem, insert it into a penicillin bottle filled with 20mL of clean water, and inoculate about 20 adult mites of Tetranychus cinnabarinus on each leaf. Check the number of adult mites after 24 hours, and select single leaves with more than 15 mites for the test. Immerse the single leaf with adult mites in the drug solution for 10 seconds, take it out and dry it, and place it in an observation room for cultivation at a temperature of 20-26℃, a light of 14hL:10hD, and a humidity of 40-60%. Investigate the number of dead and alive mites 3 days after the drug, and calculate the mortality rate.

[0266] When the concentration of the compounds 3, 4, 5, 12, 23, 24, 39, 45 and 47 of the present invention is 10 ppm, the mortality rate of the cinnabarinus spider mite is ≥ 90% 3 days after the application.

[0267] When the concentration of the compounds 1, 2, 6, 7, 8, 43, 48, 49, 51 and 53 of the present invention is 5 ppm, the mortality rate of the compounds 1, 2, 6, 7, 8, 43, 48, 49, 51 and 53 against Tetranychus cinnabarinus is ≥ 90% 3 days after the application.

[0268] According to the above method, compounds 1, 6, 43, 48, 51 were selected to be tested in parallel with KC1, KC2, and KC3 for insecticidal activity against Tetranychus cinnabarinus to compare the insecticidal activity. The test results are shown in Table 7.

[0269] Table 7: Comparison of insecticidal activity of the compounds of the present application and KC1, KC2, and KC3 against Tetranychus cinnabarinus

[0270]

[0271]

[0272] The applicant declares that the present invention illustrates the cyano-substituted benzamide compounds and their applications through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A cyano-substituted benzamide compound, characterized in that: The cyano-substituted benzamide compound has a structure shown in the following formula I: In Formula I, Y1 is selected from chlorine, bromine or iodine; Y2 is selected from chlorine, bromine, iodine, methyl, difluoromethyl or trifluoromethyl; Y3 is selected from hydrogen; R1 is selected from methyl, R2 is selected from hydrogen; X1 and X2 are independently selected from hydrogen or fluorine, wherein at least one of X1 and X2 is not hydrogen; W1 and W2 are independently an oxygen atom or a sulfur atom.

2. The cyano-substituted benzamide compound according to claim 1, characterized in that: The cyano-substituted benzamide compound is any one selected from the following compounds:

3. Use of the cyano-substituted benzamide compound according to claim 1 or 2 in preventing and controlling plant pests.

4. An insecticide composition, characterized in that The insecticide composition comprises an active component and a pesticide acceptable carrier, wherein the active component is the cyano-substituted benzamide compound as claimed in claim 1 or 2.

5. The insecticide composition according to claim 4, characterized in that The weight percentage of the active ingredient in the insecticide composition is 1-99%.

6. A method for controlling pests, characterized in that: The method comprises: applying an effective dose of the cyano-substituted benzamide compound as claimed in claim 1 or 2 or the insecticide composition as claimed in claim 4 or 5 to the harmful organisms to be controlled or the medium in which they grow.

7. The method for controlling pests according to claim 6, characterized in that: The effective dosage is 10-1000g per hectare.

8. The method for controlling pests according to claim 7, characterized in that: The effective dose is 25-500g per hectare.

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