A cyclopropanecarboxamide substituted benzamide derivative, its preparation method and use

Abstract

The present application relates to the cyclopropanecarboxamide substituted benzamide derivatives of formula (I) and the preparation method and use thereof; the compounds of formula (I) show good activity to various pests and harmful mites in agriculture or other fields. And, the compounds can obtain good control effect at very low dose. Therefore, can be used for preparing insecticide and / or miticide.

Description

[0001] This application claims priority to the earlier application filed on November 22, 2022, with patent application number 2022114695570, entitled "A Cyclopropamide-substituted Benzamide Derivative and Its Preparation Method and Use Thereof," the entire contents of which are incorporated herein by reference. Technical Field

[0002] This invention belongs to the field of insecticide and acaricide technology, specifically relating to a cyclopropamide-substituted benzamide derivative, its preparation method, and its uses. Background Technology

[0003] Modern insecticides and acaricides must meet numerous requirements, such as bioactivity levels, residual activity, spectrum of action, and other beneficial effects and potential uses. With increasing demands for the safety and environmental impact of chemicals, there is a growing need to develop safer and more effective pest control agents. Furthermore, due to years of use of insecticides and acaricides, pests have gradually developed resistance to these biological control agents, leading to unsatisfactory control results. Therefore, developing pest control agents with superior safety, control efficacy, spectrum of action, and residual effects is a future development trend.

[0004] Patent document WO2016168058 discloses the following amide compounds CK1 and CK2 (compound numbers F66 and F69):

[0005]

[0006] However, the bioactivity of the aforementioned compounds still needs further improvement. The inventors conducted in-depth research to discover insecticides and acaricides with superior performance. Summary of the Invention

[0007] To address the aforementioned problems, the present invention provides compounds of formula (I), their stereoisomers, racemates, tautomers, nitrides, or pharmaceutically acceptable salts thereof.

[0008]

[0009] R1, R2, R3, R4, R5, R 11 R 12 R 13 R 14They may be the same or different, and are independently selected from H, F, Cl, Br, I, CN, NH2, NO2, SF5, C1-C4 alkyl, C3-C6 cycloalkyl, C2-C4 alkenyl, C2-C4 alkoxy, halo-C1-C4 alkyl, halo-C1-C4 alkoxy, C1-C4 alkyl thio, C1-C4 alkyl-SO-, C1-C4 alkyl-SO2- or halo-C1-C4 alkyl-SO2-;

[0010] R6 and R7 may be the same or different, and are independently selected from H, F, Cl, Br, I or C1-C4 alkyl groups;

[0011] R8 and R9 may be the same or different, and are independently selected from H or C1-C4 alkyl groups;

[0012] R 10 Selected from H, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C4 alkyl-, C1-C4 alkyl-CO-, C3-C6 cycloalkyl-CO- or C1-C4 alkoxy-C1-C4 alkyl-CO-;

[0013] R 15 Selected from -C1-C4 alkyl-cyano, -C1-C4 alkyl-CF3 or -C1-C4 alkyl-CHF2;

[0014] R 16 Selected from -C1-C4 alkyl-cyano, unsubstituted or optionally substituted by one, two or more Rs: C3-C6 cycloalkyl or -C1-C4 alkyl-C3-C6 cycloalkyl; Rs are selected from halogens, C1-C4 alkyl or halo-C1-C4 alkyl;

[0015] Q1 and Q2 may be the same or different, and are selected independently from O or S.

[0016] According to an embodiment of the present invention: in formula (I),

[0017] R1, R2, R3, R4, R5, R 11 R 12 R 13 R 14 They may be the same or different, and are independently selected from H, F, Cl, Br, CN, SF5, methyl, ethyl, cyclopropyl, methoxy, difluoromethyl, trifluoromethyl, or trifluoromethoxy;

[0018] R6 and R7 may be the same or different, and are independently selected from H, F, Cl or Br;

[0019] R8 and R9 may be the same or different, and are independently selected from H or methyl groups;

[0020] R10 Selected from H, C1-C4 alkyl, halogenated C1-C4 alkyl, C3-C6 cycloalkyl or C3-C6 cycloalkyl-C1-C4 alkyl-.

[0021] According to an embodiment of the present invention: in formula (I),

[0022] R1, R5, R8, R9, R 11 and R 12 H is the highest value; Q1 and Q2 are both O.

[0023] R2 is a halo-C1-C3 alkyl group, F, Cl, Br, or CN;

[0024] R3 can be H, F, Cl, or Br;

[0025] R4 is a halogenated C1-C3 alkyl group, F, Cl, Br, or methyl group;

[0026] R6 and R7 are F, Cl, and Br, respectively.

[0027] R 10 H, methyl or methylcyclopropyl

[0028] R 13 For example, H, F, Cl, Br;

[0029] R 14 For example, H, F, Cl, Br;

[0030] R 15 Selected from -C1-C4 alkyl-cyano groups;

[0031] R 16 Selected from C3-C6 cycloalkyl groups.

[0032] According to an embodiment of the present invention: in formula (I),

[0033] R1, R5, R8, R9, R 11 and R 12 H is the highest value; Q1 and Q2 are both O.

[0034] R2 is trifluoromethyl, Cl, or CN;

[0035] R3 is H, F, or Cl;

[0036] R4 is trifluoromethyl, Cl, F or methyl;

[0037] R6 and R7 are Cl;

[0038] R 10 H, methyl or methylcyclopropyl

[0039] R13 It is H or Cl;

[0040] R 14 For H or F;

[0041] R 15 Selected from -C1-C4 alkyl-cyano groups;

[0042] R 16 It is selected from cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0043] In some implementations, R 15 When it is a -C1-C4 alkyl-cyano group, R 16 The substitution may be a substituted or unsubstituted -C1-C4 alkyl-C3-C6 cycloalkyl group, or a substituted or unsubstituted -C3-C6 cycloalkyl group; the substitution may be, for example, substitution by one, two or more of the following groups: F, Cl, methyl, ethyl, cyclopropyl, methoxy, difluoromethyl, trifluoromethyl or trifluoromethoxy; the substitution is preferably on the C3-C6 cycloalkyl group of the -C1-C4 alkyl-C3-C6 cycloalkyl group;

[0044] In some implementations, R 15 R 16 Not simultaneously -C1-C4 alkyl-cyano;

[0045] In some implementations, R 15 When R is -C1-C4 alkyl-CF3, 16 The substitution may be a substituted or unsubstituted -C3-C6 cycloalkyl or -C1-C4 alkyl-cyano group; the substitution may be, for example, by one, two or more of the following groups: F, Cl, methoxy, difluoromethyl, trifluoromethyl or trifluoromethoxy.

[0046] In some implementations, R 15 When R is -C1-C4 alkyl-CHF2, 16 The substituted or unsubstituted -C3-C6 cycloalkyl group; the substitution may be, for example, by one, two or more of the following groups: F, Cl, methoxy, difluoromethyl, trifluoromethyl or trifluoromethoxy.

[0047] In some implementations, R 15 The compounds are cyanomethyl, cyanoethyl, cyanopropyl, trifluoroethyl, difluoroethyl, trifluoropropyl, and difluoropropyl.

[0048] In some implementations, R 16 The compounds are cyanomethyl, cyanoethyl, cyclopropyl, cyclopropylmethyl, dichlorocyclopropyl, difluorocyclopropyl, fluorochlorocyclopropyl, methylcyclopropyl, and trifluoromethylcyclopropyl.

[0049] In some implementations, R 15 R 16 Together with the N atoms they are attached to, they form the following groups:

[0050] In some implementations, Q1 and Q2 are selected from O.

[0051] According to an embodiment of the present invention: in formula (I),

[0052] R1, R2, R3, R4, and R5 may be the same or different, and are independently selected from H, F, Br, methyl, trifluoromethyl, CHF2, or Cl;

[0053] R6 and R7 are selected from Cl or Br;

[0054] R8 is selected from H;

[0055] R9 is selected from H;

[0056] R 10 Selected from H, methyl, ethyl, trifluoroethyl, cyclopropyl, or cyclopropylmethyl;

[0057] R 11 R 12 They are either the same or different, and are selected independently from H;

[0058] R 13 R 14 They are independently selected from H, F, Br, Cl, or CF3;

[0059] R 15 R 16 Together with the N atoms they are attached to, they form the following groups:

[0060] Q1 and Q2 are selected from O.

[0061] As an example, the compound of formula (I) is selected from the following compounds:

[0062]

[0063] Where R1 = H, R5 = H, R8 = H, R9 = H, R 11 =H,R 12 =H, Q1=O, Q2=O

[0064] Table 1

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] Where R6 = Cl, R7 = Cl, R8 = H, R9 = H, Q1 = O, Q2 = O (Table 2)

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] The present invention also provides a method for preparing the compound shown in formula (I) above, comprising the following steps:

[0126] Scheme 1: The amine shown in formula (II-1) reacts with the activated acid shown in formula (III-1) to obtain the compound shown in formula (I), wherein A is the activating group;

[0127]

[0128] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R 15 R 16 It has the definition as described above, where Q1 and Q2 are selected from oxygen; or,

[0129] Option 2: When Q1 and / or Q2 are sulfur, it can be obtained by reacting the carbonyl compound of formula (I) with Q1 and / or Q2 being O obtained from Option 1 with 2,4-bis(p-methoxyphenyl)-1,3-dithiodiphosphonic heterocyclic butane-2,4-sulfide (Lawson's reagent); or,

[0130] Scheme 3: The amine shown in formula (II-2) reacts with the activated acid shown in formula (III-2') to obtain the compound of formula (I), wherein A is the activating group:

[0131]

[0132] Among them, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 R 14 R15 R 16 It has the definition described above.

[0133] According to an embodiment of the present invention, in embodiment 1, the activated carboxylic acid (III-1) may be an acyl halide, such as an acyl chloride, acyl bromide, or acyl fluoride; a carboxylic acid ester, such as p-nitrophenyl ester, pentafluorophenyl ester, ethyl (hydroxyimino)cyanoacetate, methyl ester, ethyl ester, benzyl ester, N-hydroxysuccinimide ester, hydroxybenzotriazole-1-yl ester, or hydroxypyridinyltriazole-1-yl ester; O-acyl isourea; an acid anhydride; or a thioester. The acyl chloride may be prepared from the corresponding carboxylic acid (III) by means of, for example, oxaloyl chloride or thionyl chloride. Activated carboxylic acid esters can be prepared from carboxylic acid (III) and ureonium salts, such as 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethylureonium hexafluorophosphate (HBTU), or (1-cyano-2-ethoxy-2-oxoethyleneaminooxy)dimethylamino- Morpholino-carbamonite hexafluorophosphate (COMU) can also be prepared from a coupling agent such as benzotriazol-1-yl-oxytripyrrolidinephosphonium hexafluorophosphate (PyBop), or from a coupling agent such as hydroxybenzotriazol-monohydrate (HOBt) or 1-hydroxy-7-azabenzotriazol (HOAt), consisting of carboxylic acid (III) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or dicyclohexylcarbodiimide. O-acylisourea can be prepared from the dehydrated carbodiimide of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or dicyclohexylcarbodiimide. Activated carboxylic acid esters can also be prepared from a coupling agent such as 2-chloro-1,3-dimethylimidazolium (CIP) in the presence of a triazole such as 1-hydroxy-7-azabenzotriazol (HOAt), consisting of carboxylic acid (III) and a coupling agent such as 2-chloro-1,3-dimethylimidazolium (CIP). Activated carboxylic acid esters can also be prepared in the presence of a base such as pyridine from a coupling agent of carboxylic acid (III) with a coupling agent such as 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphacyclohexane 2,4,6-trioxide.

[0134] According to an embodiment of the present invention, the activated acid represented by formula (III-1) is prepared by the following method:

[0135]

[0136] R1, R2, R3, R4, R5, R6, R7, R8, R9, and A have the definitions described above.

[0137] According to an embodiment of the present invention, in Scheme 1, the amine represented by formula (II-1) reacts with the activated acid represented by formula (III-1) in an anhydrous aprotic solvent of dichloromethane, dichloroethane, tetrahydrofuran, toluene, or any combination thereof; the reaction temperature is 0–120 °C.

[0138] The reaction preferably occurs in the presence of organic or inorganic bases such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydroxide, or potassium hydroxide.

[0139] According to an embodiment of the present invention, in Scheme 3, the amine represented by formula (II-2) reacts with the activated acid represented by formula (III-2') in an anhydrous aprotic solvent of dichloromethane, dichloroethane, tetrahydrofuran, toluene, or any combination thereof, at a temperature of about 0 to 120°C, in the presence of an organic or inorganic base such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydroxide, or potassium hydroxide.

[0140] According to an embodiment of the present invention, in embodiment 3, the activated carboxylic acid (III-2') may be an acyl halide, such as an acyl chloride, acyl bromide, or acyl fluoride; a carboxylic acid ester, such as p-nitrophenyl ester, pentafluorophenyl ester, ethyl (hydroxyimino)cyanoacetate, methyl ester, ethyl ester, benzoyl ester, N-hydroxysuccinimide ester, hydroxybenzotriazole-1-yl ester, or hydroxypyridinyltriazole-1-yl ester; O-acyl isourea; an acid anhydride; or a thioester. The acyl chloride may be prepared from the corresponding carboxylic acid by means of, for example, oxaloyl chloride or thionyl chloride. Activated carboxylic acid esters can be prepared from carboxylic acids and ureon salts, such as 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethylureon hexafluorophosphate (HBTU), or (1-cyano-2-ethoxy-2-oxoethyleneaminooxy)dimethylamino- Morpholino-carbamonite hexafluorophosphate (COMU) can also be prepared from a coupling agent such as benzotriazol-1-yl-oxytripyrrolidinephosphonium hexafluorophosphate (PyBop), or from a carboxylic acid with a coupling agent such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or dicyclohexylcarbodiimide in the presence of hydroxybenzotriazine monohydrate (HOBt) or 1-hydroxy-7-azabenzotriazine (HOAt). O-acylisourea can be prepared from the dehydrated carbodiimide of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or dicyclohexylcarbodiimide. Activated carboxylic acid esters can also be prepared from a carboxylic acid with a coupling agent such as 2-chloro-1,3-dimethylimidazolium (CIP) in the presence of a triazole such as 1-hydroxy-7-azabenzotriazine (HOAt). Activated carboxylic acid esters can also be prepared in the presence of a base such as pyridine by coupling of carboxylic acid with a coupling agent such as 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphoscyclohexane 2,4,6-trioxide.

[0141] The amine represented by formula (II-2) can be purchased commercially or prepared using methods known to those skilled in the art.

[0142] In some embodiments, in Scheme 1, the amine represented by formula (II-1) can be prepared by the following method:

[0143] When R 10 When hydrogen is selected, following the method described above, an activated carboxylic acid (II-4) is first prepared from a carboxylic acid (II-3). The activated carboxylic acid (II-4) can be an acyl halide, such as an acyl chloride, acyl bromide, or acyl fluoride; a carboxylic acid ester, such as p-nitrophenyl ester, pentafluorophenyl ester, ethyl (hydroxyimino)cyanoacetate, methyl ester, ethyl ester, benzoyl ester, N-hydroxysuccinimide ester, hydroxybenzotriazol-1-yl ester, or hydroxypyridinyltriazol-1-yl ester; O-acyl isourea; an acid anhydride; or a thioester. The activated carboxylic acid (II-4) then reacts with the amine shown in (II-2) in an anhydrous aprotic solvent of dichloromethane, dichloroethane, tetrahydrofuran, toluene, or any combination thereof, at a temperature of about 0–120 °C, in the presence of an organic or inorganic base such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, potassium carbonate, sodium carbonate, sodium hydroxide, or potassium hydroxide to obtain the compound of formula (II-5). The compound shown in formula (II-5) is reduced to obtain the compound shown in formula (II-1), for example, by using metallic iron or hydrogen gas, with ethanol or methanol as the solvent, and reacting at room temperature to reflux to obtain the compound shown in formula (II-1). The reaction can be carried out with reference to the methods described in the 2011 edition of the "Handbook of Organic Compound Synthesis", patent document CN1993328B or EP085890, or other similar methods.

[0144]

[0145] Where R 11 R 12 R 13 R 14 R 15 R 16 A has the definition described above;

[0146] When R 10 When other groups are selected, the amine represented by formula (II-1) can be prepared by methods known to those skilled in the art, for example, by the following methods:

[0147]

[0148] Where R 10 R 11 R 12 R 13 R 14 R 15 R 16 It has the definition described above;

[0149] For example, the reaction can be carried out with reference to the method described in Wang Jie, Qin Shuai, Pesticides 2020, Vol.59, No.1 or a similar method.

[0150] In some embodiments, cyclopropionic acid (III) can be prepared from an unsaturated aldehyde (III-1'), wherein R1, R2, R3, R4, R5, R6, R7, R8, and R9 have the definitions described above. The unsaturated aldehyde represented by formula (III-1') can be synthesized from commercially available aldehydes with appropriate substitutions, as described in PCT 2010123006. In the presence of acids (such as hydrobromic acid, N-bromosuccinimide, hydrochloric acid, N-bromosuccinimide, hydrochloric acid, N-chlorosuccinimide, and pyridinium p-toluenesulfonate (PPTS)) in C1-C6 alkyl alcohols, at 0°C to room temperature, formula (III-1') reacts with orthoformic acid (C1-C6) alkyl esters to give acetal (III-2). Acetal (III-2) is reacted with carbides of haloforms such as chloroform or bromoform in the presence of bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, or potassium carbonate, and with phase transfer catalysts such as benzyltriethylamine chloride, (-)-N-dodecyl-N-methylephedrine bromide, tetramethylammonium bromide, tetrabutylammonium tetrafluoroborate, tetramethylammonium chloride, or tetrabutylammonium hexafluorophosphate, at 15–60°C. The source is reacted to prepare cyclopropyl acetal (III-3). Cyclopropyl acetal (III-3) is oxidized to aldehyde (III-4) at 15–45 °C in polar solvents selected from acetone, acetonitrile, methanol, ethanol, N,N-dimethylformamide, dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, and 1,4-dioxane, in the presence of an aqueous inorganic acid selected from nitric acid, hydrochloric acid, hydrobromic acid, and sulfuric acid. Aldehyde (III-4) is oxidized to cyclopropyl acid (III) by oxidizing with oxidants such as potassium permanganate or sodium permanganate, or under Pinnick oxidation conditions, in polar aprotic solvents selected from acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, or 1,4-dioxane at 0–60 °C.

[0151]

[0152] R1, R2, R3, R4, R5, R6, R7, R8, and R9 have the definitions described above; Ra is selected from C1-C6 alkyl groups.

[0153] In some embodiments, cyclopropyl acetic acid (III) can also be reacted with mesitylene (III-5) in the presence of a carbene source such as chloroform or bromoform and a phase transfer catalyst such as N-benzyl-N,N-diethylethylamine chloride in a polar protic solvent at a temperature of 0–50 °C in the presence of a base such as sodium hydroxide or potassium hydroxide to give diarylcyclopropane (III-6); diarylcyclopropane (III-6) is then treated with a ruthenium transition metal chloride in the presence of an oxidant such as sodium periodate in a mixed solvent such as water, ethyl acetate, and acetonitrile at a temperature of 0–50 °C to give cyclopropylcarboxylic acid (III).

[0154]

[0155] R1, R2, R3, R4, R5, R6, R7, R8, and R9 have the definitions described above; Rb is selected from C1-C4 alkyl groups.

[0156] In some embodiments, cyclopropionic acid (III) can be resolved into (R,R) and (S,S) enantiomers by known methods, as described in Kovalenko VN, Kulinkovich OGTetrahedron: Asymmetry 2011, 22, 26:

[0157]

[0158] According to an embodiment of the present invention, the reaction can be carried out with reference to the method described in patent document CN 107466291.

[0159] The preparation of the compound of formula (I) and its starting materials in this article can be carried out according to the appropriate reaction conditions and the selection of starting materials in each case. For example, in a one-step reaction, only one substituent can be replaced by another substituent according to the invention, or multiple substituents can be replaced by other substituents according to the invention in the same reaction step.

[0160] If the compounds cannot be obtained via the above-described route, they can be prepared by deriving other compounds or by conventionally modifying the synthetic route.

[0161] After the reaction is complete, the reaction mixture can be post-processed in a conventional manner, such as by mixing with water, separating the phase, and, if appropriate, purifying the crude product by chromatography, for example, on alumina or silica gel.

[0162] The pharmaceutically acceptable salt of the compound represented by formula (I) of this invention can be prepared by known methods.

[0163] The above preparation method can obtain a mixture of isomers of the compound shown in formula (I). If pure isomers are required, they can be separated by conventional methods such as crystallization or chromatography.

[0164] Unless otherwise specified, all of the above reactions can be conveniently carried out at atmospheric pressure or at the pressure of the specific reaction itself.

[0165] The present invention also provides a pesticide composition, such as an insecticidal and / or acaricidal composition, comprising one, two or more of the following as active ingredients: a compound of formula (I), its stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof.

[0166] According to an embodiment of the present invention, the weight percentage of the active ingredient in the composition is 0.1-99.9%, for example, 0.5-99%.

[0167] According to embodiments of the present invention, the composition further includes one, two, or more of agricultural and / or forestry and / or sanitary acceptable carriers.

[0168] According to an embodiment of the present invention, the composition can be administered in the form of a formulation.

[0169] For example, the compound shown in formula (I) is dissolved or dispersed in a carrier or formulated as an active ingredient to facilitate dispersion when used as an insecticide and / or acaricide.

[0170] According to embodiments of the present invention, the formulation includes, but is not limited to, the following forms: granules, wettable powders, oil suspensions, water suspensions, water emulsions, aqueous solutions, emulsifiable concentrates, or microcapsules, etc.

[0171] According to embodiments of the invention, a liquid or solid carrier and optionally a surfactant may also be added to the composition.

[0172] The present invention also provides the use of one, two or more of the compounds of formula (I), their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof as pesticides, such as insecticides and / or acaricides.

[0173] The present invention also provides the use of one, two or more of the compounds of formula (I), their stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof in the preparation of pesticides, such as insecticides and / or acaricides.

[0174] The present invention also provides a method for controlling pests and / or mites, comprising applying an effective amount of one, two or more of the following: a compound of formula (I), its stereoisomers, racemates, tautomers, nitrogen oxides or pharmaceutically acceptable salts thereof, or applying the composition to a growth medium of pests and / or mites.

[0175] According to an embodiment of the present invention, the effective amount is 10 to 1000 grams per hectare, preferably 20 to 500 grams per hectare.

[0176] The active substances of this invention, or the active substances to be used in this invention, are suitable for protecting plants and plant organs, increasing yield, improving the quality of harvested products, and controlling pests, particularly in agriculture, horticulture, animal husbandry, forestry, gardens and recreational facilities, warehouse pest control and material protection, and in the sanitation field, where pests and mites are present. They are preferably used in plant protection compositions. They are active against conventionally susceptible and resistant species and against all or individual developmental stages. The aforementioned pests and mites include, but are not limited to:

[0177] Arthropoda, especially Arachnida, includes species such as *Acarus* spp., *Aceriasheldoni*, *Aculops* spp., *Aculus* spp., *Amblyomma* spp., *Amphitetranychus viennensis*, *Argas* spp., *Boophilus* spp., *Brevipalpus* spp., *Bryobiagraminum*, *Bryobiapraetiosa*, *Centruroides* spp., and *Chorioptes*. spp.), Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Epirimerus pyri, Eutetranychus spp., Eriophyes spp., Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Metatatetranychus spp.), Neutrombicula autumnnalis, Nuhersa spp., Oligoychus spp., Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Phyllocoptrutaoleivora, Polyphagotarsonemuslatus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.), Middle Eastern golden scorpion (Scorpiomaurus), Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., Tetranychus spp., Trombicula alfreddugesi, Vaejovis spp., Vasateslycopersici;

[0178] Coleoptera (Beetles): * *Acanthoscelides* spp. (bean weevil), * *Acanthoscelides obtectus* (common pea weevil), * *Agrilus planipennis* (flowering ash beetle), * *Agriotes* spp. (wireworm), * *Anoplophoraglabripennis* (Asian longhorn beetle), * *Anthonomus* spp. (cotton boll weevil), * *Anthonomus grandis* (cotton boll weevil), * *Aphidius* spp. (branch wasp), * *Apion* spp. (weevil), * *Apogonia* spp. (cane beetle grub), * *Atacnius sprctulus* (black velvet beetle), * *Atomaria linearis* (small beetle beetle). The following species are listed: mangold beetle, Aulacophore spp., Bothynoderes punctiventris (beef root weevil), Bruchus spp. (beef weevil), Bruchus pisorum (pea weevil), Cacoesia spp., Callosobrus maculatus (southern cowpea weevil), Carpophilus hempteras (dried fruit beetle), Cassida vittata, Ccrostcrna spp., Ccrotoma spp. (chrysomcids), Cerotoma trifur cata (bean leaf beetle), and Ceutorhynchus (turtle weevil). spp. (weevils), *Ceutorhynchus assimilis* (cabbage seedpod weevil), *Ceutorhynchus napi* (cabbage curculio), *Chaetocnema spp.* (golden trichomoniasis), *Colaspis spp.*(Earth beetle), Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar (Plum beetle), Cotinus nitidis (Green Junebeetle), Crioceris asparagi (Earth beetle), Cryptolestes ferrugincus (Rusty grain beetle), Cryptolestes pusillus (Flat grain beetle), Cryptolestes turcicus (Turkish grain beetle), Ctenicera spp. (Nematode), Curculio spp. (Weevil), Cyclocephala spp. (Grub), Cylindrocpturus (Dense-spotted twig weevil) *Adpersus* (sunflower stem weevil), *Deporaus marginatus* (mango leaf-cutting weevil), *Dermestes lardarius* (ham weevil), *Dermestes maculates* (white-bellied weevil), *Diabrotica spp.* (leaf beetle), *Epilachna varivcstis* (Mexican beetle), *Raustinus cubae* (stem borer), *Hylobius pales* (fighting weevil), *Hypera spp.* (leaf weevil), *Hypera postica* (alfalfa leaf weevil), *Hyperdoes spp.* (Argentine stem weevil), *Hypothenemus* (coffee berry weevil). hampei (coffee fruit beetle), species of the genus Ips spp.(Spiny-legged beetle (engravers)), Tobacco beetle (Lasioderma serricorne), Potato beetle (Leptinotarsa ​​decemlineata), Liogenys fuscus, Liogenys suturalis, Rice water weevil (Lissorhoptrus oryzophilus), Powder beetle (Lyctus spp.), Powder post beetle (Maecolaspis joliveti), Megascelis spp., Corn beetle (Melanotus communis), Blossom beetle (Meligethes spp.), Blossom beetle (Meligethes aeneus), Common European beetle (Melolontha melolontha), Oberea brevis, Longhorn beetle (Oberea brevis) * *linearis*, *Oryctesrhinoceros* (date palm beetle), *Oryzaephilus mercator* (merchant grain beetle), *Oryzaephilus surinamensis* (sawtooth grain beetle), *Otiorhynchus spp.* (weeviler), *Oulemamelanopus* (orange-legged leaf beetle), *Oulema oryzae*, *Pantomorus spp.* (weeviler), *Phyllophaga spp.* (May / June beetle), *Phvllophaga cuyabana*, *Phyllotreta* (yellow-striped flea beetle). spp. (Golden Trichomonas), species of the genus Phynchites spp.), Japanese scarab beetle (Popillia japonica), large grain borer (Prostephanus truncates), lesser grain borer (Rhizoperthadominica), European scarab beetle (Rhizotrogus spp.), weevil (Rhynchophorus spp.), wood moth (Scolytus spp.), grain weevil (Shenophorus spp.), pea leaf weevil (Sitonalincatus), rice weevil (Sitophilus spp.), grain weevil (Sitophilus granaries), rice weevil (Sitophilus oryzae). The following species are listed: *Stegobium paniceum* (drugstore beetle), *Tribolium spp.* (face beetle), *Tribolium castaneum* (red flour beetle), *Tribolium confusum* (confused flour beetle), *Trogoderma variabile* (warehouse beetle), and *Zabrus tenebioides*.

[0179] Dermaptcra (earwigs).

[0180] Neuroptera (cockroaches): German cockroach (Blattella germanica), Oriental cockroach (Blatta orientalis), Pennsylvania wood cockroach (Parcoblatta pennylvanica), American cockroach (Periplaneta americana), Australian cockroach (Periplaneta australoasiae), brown cockroach (Pcriplancta brunnca), smoky brown cockroach (Periplaneta fuliginosa), sugarcane cockroach (Pyncoselus suninamensis). cockroach) and long-bearded cockroach (Supella longipalpa) (brownbanded cockroach).

[0181] Diptera (flies): *Aedes* spp. (mosquito), *Agromyza frontella* (alfalfa leafminer), *Agromyza* spp. (leafminer), *Anastrepha* spp. (fruit fly), *Anastrepha suspensa* (Caribbean fruit fly), *Anopheles* spp. (mosquito), *Batrocera* spp. (fruit fly), *Bactroceracucurbitae* (melon fly), *Bactroceradorsalis* (orange fruit fly), *Ceratitis* spp. (fruit fly), *Ceratitiscapitata* (Mediterranean fruit fly), *Chrysops* (tigerfly). *Cochliomyia spp.* (spp.) (deer fly), *Cochliomyia* spp. (slipper fly larvae), *Contarinia* spp. (slipper fly), *Culex* spp. (mosquito), *Dasineura* spp. (slipper fly), *Dasineura brassicae* (cabbage leaf fly), *Delia* spp., *Delia pla tura* (seed cornmaggot), *Drosophila* spp. (vinegar fly), *Fannia* spp. (housefly), *Fannia canicularis* (little house fly), *Fannia scalaris* (grey-bellied house fly), *Gasterophilus intestinalis* (horse stomach fly), *Gracillia* perseae, Haematobia irritans (hornfly), Hylemyia spp. (root maggot), Hypoderma lineatum (common cattle grub), Liriomyza spp.(Leaf miner), cabbage leafminer (Liriomyza brassica), sheep tick (Melophagus ovinus), housefly (Musca spp.), face fly (Muscaa utumnalis), housefly (Vuscadomestica), sheep bot fly (Oestrusovis), Swedish straw fly (Oscinella frit), beetleafminer (Pegomyia betae), carrot rust fly (Psila rosae), cherry fruit fly (Rhagoletis cerasi), apple fruit fly (Rhagoletis) The following species are listed: *Pomonella* (apple maggot), *Sitodiplosismosellana* (orange wheat blossom midge), *Stomoxyscalcitruns* (stable fly), *Tahanus* spp. (horsefly), and *Tipula* spp. (large mosquito).

[0182] Hemiptera (bugs): * *Acrosternum hilare* (green stinkbug), * *Blissus leucopterus* (chinch bug), * *Calocoris norvegicus* (potato mirid), * *Cimex hemipterus* (tropical bed bug), * *Cimex lectularius* (bed hug bug), * *Daghertus fasciatus*, * *Dichelops furcatus*, * *Dysdercus suturellus* (cottonstainer), * *Edessa meditabunda*, * *Eurygaster maura* (cereal bug), * *Euschistus heros*, * *Euschistus* (brown stink bug). The following species are listed: *Helopeltis antonii* (brown stink bug), *Helopeltis theivora* (tea blightplant bug), *Lagynotomus spp.* (stink bug), *Leptocorisa oratorius* (large rice-margined bug), *Leptocorisa varicornis* (different rice-margined bug), *Lygus spp.* (plant bug), *Lygushesperus* (western tarnished plant bug), *Maconellicoccushirsutus* (hibiscus pink bug), *Neurocolpus longirostris* (southern greenstink bug), and *PhyLocoris spp.* (plant bug).(Mirid bug), California plant mirid bug (Phytocoris californicus), Phytocoris relativus, Piezodorus guildingi, four-lined plant bug (Poecilocapsus lineatus), Psallus vaccinicola, Pseudacystaperseae, Scaptocoris castanea, and Triatoma spp. (bloodsucking conenose bug / kissing bug).

[0183] Homoptera (aphids, scale insects, whiteflies, leafhoppers): Pea aphid (Acrythosiphonpisum), Adelges spp. (adelg ds), cabbage whitefly (Aleurodesproletella), spiral whitefly (Aleurodicus di sperses), woolly whitefly (Aleurothrixus flccosus), white-skinned scale (Aluacaspisspp.), Amrasca bigutella bigutella, leafhopper (Aphropho ra spp.), red scale (Aonidiella aurantii), aphid (Aphis spp.), cotton aphid (Aphis gossypii). Apple aphid (Aphis pomi), foxglove aphid (Aulacorthitm solani), whitefly (Bemisia spp.), silver leaf aphid (Bemisia argentifolii), sweet potato whitefly (Bemisia tabaci), tobacco whitefly (Bemisia tabaci (Gennadius)), Russian aphid (Brachycolus noxius), asparagus aphid (Brachycorynclia asparagi), cabbage aphid (Brevicoryne brassicae), scale insect (Ceroplastes spp.), red wax scale (Ceroplastes rubens). Scale, *Chionaspis* spp. (scale), *Chrysomphalus* spp. (scale), *Coccus* spp. (scale), *Dysaphis plantaginea* (rosy apple aphid), *Empoasca* spp.(Leafhopper), Apple cotton aphid (Eriosoma lanigerum) (woolly apple aphid), Cottony scale (Icerya purchasi) (cottonycushion scale), Mango yellow-lined leafhopper (Idioscopus nitidulus) (mango leafhopper), Smaller brown planthopper (Laodelphax striatellus) (Laodelphax striatellus), Species of Lepidosaphesspp., Species of Macrosiphum spp., Macrosiphum euphorbiae (potato aphid), English grain aphid (Macrosiphum granarium), Rose aphid (Macrosiphum rosae) (rose aphid), Four-lined leafhopper (Macrosteles quadrilin eatus) (aster leafhopper) The following species are listed: Mahanarvafrimbiolata, Metopolophium dirhodum (rose grain aphid), Midis longicornis, Myzus persicae (green peach aphid), Nephotettix spp. (leafhopper), Nephotettix cinctipes (green leafhopper), Nilaparvata lugens (brown planthopper), Parlatoria pergandii (chaff scale), Parlatoriaziziphi (ebony scale), Peregrinus maidis (corn delphacid), Philaenus spp. (blower), Phylloxera vitifoliae (grape phylloxera), Physokermes *Pseudococcus* (spruce bud scale), *Planococcus* spp. (meat scale), *Pseudococcus* spp.(Pincapple mcaly bug), Pineapple mcaly bug (Pscudococcus brcvipcs), Orchard scale (Quad raspidiotus perniciosus) (San Jose scale), Aphid species (Rhapalosiphum spp.) (Aphid), Corn leaf aphid (Rhapalosiphum maida) (corn leafaphid), Oatbird-cherry aphid (Rhapalosiphumpadi), Scale insect (Saissetia spp.) (scale insect), Black scale insect (Saissetiaoleae), Green bug (Schizaphis graminum), British wheat aphid (Sitobion avenge), White-backed planthopper (Sogatella) *Furcifera* (white-backed planthopper), *Therioaphis* spp. (aphid), *Toumeyella* spp. (scale insect), *Toxoptera* spp. (aphid), *Trialeurodes* spp. (whitefly), *Trialeurodes vaporariorum* (greenhouse whitefly), *Trialeurodes abutiloneus* (bandedwing whitefly), *Unaspis* spp. (scale insect), *Unaspis yanonensis* (arrowhead scale), and *Zulia entreriana*.

[0184] Hymenoptera (ants, wasps, and bees): *Acromyrrmex* spp., *Athalia rosae*, *Atta* spp. (leafcutting ants), *Camponotus* spp. (carpenter ant), *Diprion* spp. (sawfly), *Formica* spp. (ant), *Iridomyrmex humilis* (Argentine ant), *Monomorium* spp. (subspecies), *Monomorium minumum* (littleblack ant), *Monomorium pharaonis* (Pharaoh ant), *Neodiprion* spp. (sawfly), *Pogonomyrmex* spp. (harvester ants), Polistes spp. (paperwasp), Solenopsis spp. (fire ants), Tapoinum sessile (odorous house ants), Tetranomorium spp. (pavement ants), Vespula spp. (yellow jacket ants), and Xylocopa spp. (carpenter bees).

[0185] Isoptera (termites): *Coptotermes spp.*, *Coptotermes curvignathus*, *Coptotermes frenchii*, *Coptotermes formosanus* (Formosan subterranean termite), *Cornitermes spp.* (nasute termite), *Cryptotermes spp.* (drywood termite), *Heterotermes spp.* (desert subterranean termite), *Ileterotermes aureus*, *Kalotermes spp.* (drywood termite), *Incistitermes spp.* (drywood termite), *Macrotermes* *Reticulitermes* spp. (fungus growing termite), *Marginitermes* spp. (drywood termite), *Microcerotermes* spp. (harvester termite), *Microtermes obesi*, *Procornitermes* spp., *Reticulitermes* spp. (soil-dwelling termite), *Reticulitermes banyulensis*, *Reticulitermes grassei*, *Reticulitermes f la vi pes* (eastern soil-dwelling termite), *Reticulitermes hageni*, *Reticulitermes hesperus* (western soil-dwelling termite), *Reticulitermes santonensis*, *Reticulitermes santonensis* *Reticulitermes speratus*, *Reticulitermes tibialis*, *Reticulitermes virginicus*, *Schedorhinotermes spp.*, and *Zootermopsis spp.* (wood-rotting termite).

[0186] Lepidoptera (moths and butterflies): *Achoea janata*, *Adoxophyes* spp., *Adoxophyes orana*, *Agrotis* spp. (root cutter), *Agrotis ipsilon* (black root cutter), *Alabama argillacea* (cottonleaf worm), *Amorbia cuneana*, *Amyelosi transitella* (navel orange worm), *Anacamptodes defectaria*, *Anarsia lineatella* (peach twig borer), *Anomis sabulijera* (jute looper), *Anticarsiag emmatalis* (velvetbean caterpillar), *Archips argyrospila* (fruit tree leafroller), *Archips rosana* (rose leafroller). The following moths are listed: leafroller, *Argyrotaenia* spp. (tortricid moths), *Argyrotaenia citrana* (orange tortrix), *Autographa gamma*, *Bonagota cranaodcs*, *Borbocinnara* (rice leafroller), *Buccula trix thurberiella* (cotton leafperforator), *Caloptilia* spp. (leaf miner), *Capua reticulana*, *Carposina niponensis* (peach fruit moth), *Chilo* spp., *Chlumetia transversa* (mango shoot borer), *Choristoneurarosaceana* (obliquebanded leaf roller), and *Chrysodeixis* spp.The following species are listed: *Cnaphalocerus mediumis* (grass leafroller), *Colias spp.*, *Conpomorpha cramerella*, *Cossus cossus* (wood moth), *Crambuss spp.* (Sod webworms), *Cydia funebrana* (plum fruit moth), *Cydia molesta* (oriental fruit moth), *Cydianignicana* (pea moth), *Cydia pomonella* (codling moth), *Darna diducta*, *Diaphania spp.* (stem borer), and *Diatraeas spp.* (stalk borer). (The following are a list of species and their names, not part of the main text): *Diatraea saccharalis* (sugarcane borer), *Diatraea graniosella* (southwester cornborer), *Earias spp.* (cotton bollworm), *Earias insulata* (Egyptianbollworm), *Eariasvit.ella* (rough northern bollworm), *Ecdytopophaaurantianum*, *Elasmopalpus lignosellus* (lesser cornstalk borer), *Epiphysiaspostrutta na* (light brown apple moth), *Ephestia spp.* (almond moth), *Ephestia cautella* (almond moth), *Ephestia* (tobacco white moth). Tobacco moth (Ephestia kuehniella), Mediterranean flour moth (Ephestia kuehniella), and species of the genus Epimeces (Epimeces spp.).), Epinotia aporema, Erionota thrax (bananaskipper), Eupoecilia ambiguella (grape berry moth), Euxoa auxiliaris (armycutworm), Feltia spp. (root cutter), Gortyna spp. (stem borer), Grapholita molesta (peach (apricot) fruit borer), Hedylepta indicata (bean leaf webber), Helicoverpa spp. (noctuid moth), Helicoverpa *Helicoverpazea* (corn borer), *Heliothis* spp. (noctus), *Heliothis virescens* (tobacco budworm), *Hellula undalis* (cabbageweb worm), *Indarbela* spp. (root borer), *Keiferia lycopersicella* (tomato pinworm), *Leucinodesorbonalis* (eggplantfruit borer), *Leucoptera malifoliella*, *Lithocollectis* spp., *Lobesia botrana* (grape fruit moth), *Loxagrotis* spp. (noctus), *Loxagrotis albicosta* (western bean moth) Cutworm, gypsy moth (Lymantria dispar), apple leafminer (Lyonetia clerkella), oil palm bagworm (Mahasenacorbetti), and tent caterpillar (Malacosoma spp.).(tent caterpillars), cabbage armyworm (Mamestra brassicae), bean pod borer (Marucatestulalis), bagworm (Metisa plana), true armyworm (Mythimna unipuncta), small tomato borer (Neoleucinodes elegantalis), rice leaf roller (Nym phulade punctalis), winter moth (Operophtherabrumata), European corn borer (Ostrinianubilalis), Oxydia vesulia, common grape leaf roller (Pandemiscerasana), brown apple leaf roller (Pandemis heparana) The following species are listed: *Pectinophoragos sypiella* (red bollworm), *Peridroma spp.* (root cutter), *Peridroma saucia* (variegated cutworm), *Perileucopte ra coffeella* (white coffeeleafminer), *Phthorimaea operculella* (potato tuber moth), *Phyllocnisitis citrella* (citrus leafminer), and *Phyllonorycter spp.*(Leaf miner), cabbage white butterfly (Pieris ra pae), imported cabbage worm, green armyworm (Plathypenascabra), Indian meal moth (Plodia interpunctella), diamondback moth (Plutellaxylostella), grape berry moth (Polychrosis viteana), citrus endocarps, olive moth (Prsys oleae), armyworm (Pseudaletia spp.), armyworm (Pseudaletia unipunctata), soybean looper (Pseudoplusia includens), inchworm (Rachiplusia nu), rice stem borer (Chilo suppressalis), rice stem borer (Scirpophaga incertulas), stem borer (Sesamia) spp. (stem borer), rice stem borer (Sesamia inferens) (pink rice stemborer), rice stem borer (Sesamianona grioides), copper-spotted brown tussock moth (Setora nitens), wheat moth (Sitotroga cerealella) (Angoumois grain moth), grape long-bearded leafroller (Sparganothis pilleriana), armyworm (Spodoptera spp.), beet armyworm (Spodoptera exigua), fall armyworm (Spodoptcrafugipcrda), southern armyworm (Spodoptera oridania), root borer (Synanthedon spp.), Theclabasilides, Thermisia gemmatalis, clothes moth (Tineola) bisselliella (webbingclothesmoth), Trichoplusia ni (cabbage looper), Tomato leafminer (Tutsabsoluta), and Yponomeuta spp.The species include the coffee leopard moth (Zeuzeracoffeae) (red branchborer), the pear leopard moth (Zeuzerapyrina), and the beet armyworm (Spodoptera litura (Fabricius)).

[0187] Mallophaga (chewing lice): sheep louse (Bovicola ovis), chicken body louse (Menacanthus stramineus), and common hen house louse (Menopon gallinea).

[0188] Orthoptera (grasshoppers, locusts, and crickets): *Anabrus simplex* (Mormon cricket), *Gryllotalpidae* (mole cricket), *Locusta migratoria*, *Melanoplus spp.* (grasshopper), *Microcentrumretinerve* (angular winged katydid), *Pterophylla spp.* (katydid), *chistocerca gregaria*, *Scudderia furcata* (fork-tailed bush katydid), and *Valanga nigricorni*.

[0189] The order Phthiraptera (sucking louse): *Haematopinus spp.* (cattle and pig lice), *Linognathus ovillus* (sheep louse), *Pediculus humanus capitis* (body lice), *Pediculus humanus humanus* (body lice), and *Pthirus pubis* (crab louse).

[0190] Siphonaptera (fleas): Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea), and Pulex irritans (human flea).

[0191] Thysanoptera (Thrips): Tobacco thrips (Frankliniella fusca), Western flower thrips (Frankliniella occidentalis), Frankliniella shultzei, Corn thrips (Frankliniella williamsi), Greenhouse thrips (Ilioliothrips haemorrhaidalis), Riphiphorothrips cruentatus, Scirtothrips spp., Citrus thrips (Scirtothrips cirri), Yellow tea thrips (Scirtothrips dorsalis), Taeniothrips rhopalantennalis, and Thrips spp.

[0192] Thysanura (bristletails): Lepisma spp. (silverfish) and Thermobia spp. (thermobia).

[0193] Order Acarina (mites and ticks): *Acarapsis woodi* (tracheal mite of honeybee), *Acarus spp.* (food mite), *Acarus siro* (grain mite), *Aceria mangiferae* (mango bud mite), *Aculops spp.*, *Aculops lycopersici* (tomatorussetmite), *Aculops pelekasi*, *Aculus pelekassi*, *Aculus schlechtendali* (apple rust mite), *Amblyommaamcricanum* (lone star tick), *Boophilus* spp. (tick), *Brevipalpus obovatus* (privet mite), *Brevipalpus phoenicis* (red and blackflat mite), *Demodex* spp. (mange mites), *Dermacentors* spp. (hard tick), *Dermacentor variabilis* (American dog tick), *Dermatophagoides pteronyssinus* (house dust mite), *Eotetranycus* spp., *Eotetranychus carpini* (yellow spider mite), *Epitimerus* spp., *Eriophyes* spp., *Metatetranycus* spp. (tick), *Metatetranycus* spp. spp.), cat ear mite (Notoedres cati), small claw mite (Oligonychus spp.), coffee small claw mite (Oligonychus coffee), southern red claw mite (Oligonychus ilicus), panonychus spp.The following are listed as examples of spider mites: * *Panonychuscirri* (citrus-red mite), * *Panonychus ulmi* (European red mite), * *Phyllocoptruta oleivora* (citrus rust mite), * *Polyphagotarsonemun latus* (broad mite), * *Rhipicephalus sanguineus* (brown dog tick), * *Rhizoglyphus spp.* (bulb mite), * *Sarcoptes scabiei* (itch mite), * *Tegolophus perseaflorae* (avocado gall mite), * *Tetranychus spp.* (tetranychus urticae) (two-spotted spider mite). The mite (Varroa destructor) and the bee mite.

[0194] Nematodes (Nematodes): *Aphelenchoides* spp. (bud and leaf nematode and pine wood nematode), *Belonolaimus* spp. (sting nematodes), *Criconemella* spp. (ring nematodes), *Dirofilaria immitis* (dog heartworm), *Ditylenchus* spp. (stem and bulb nematodes), *Heterodera* spp. (cyst nematode), *Heterodera zeae* (corncyst nematode), *Hirschmanniella* spp. (root nematodes), *Hoplolaimus* spp. (lance nematodes), *Meloidogyne* (root-knot nematode). The species *Meloidogyne incognita* (root-knot nematode), *Onchocercavolvulus* (hook-tail worm), *PraLylenchus* (lesion nematode), *Radiopholus* (burrowing nematode), and *Rotylenchus reniformis* (kidney-shaped nematode) are listed.

[0195] Synthetic class (synthetic insects): White pine worm (Scutigerella immaculata).

[0196] In some embodiments, the pests and / or mites are selected from, for example, the following: western flower thrips, diamondback moth, cabbage white butterfly, armyworm, beet armyworm, rice stem borer, rice leaf roller, flea beetle, and carmine spider mite.

[0197] Due to their positive properties, the compound shown in formula (I) can be advantageously used to protect important crops, livestock and breeding stock in agriculture and horticulture, as well as environments frequented by humans, from pests and / or mites.

[0198] To achieve the desired effect, the amount of the compound shown in formula (I) varies depending on various factors, such as the compound used, the crop being protected, the type of pest, the degree of infection, climatic conditions, the application method, and the formulation used.

[0199] The selection of dosage forms or compositional components described herein should be consistent with the physical properties of the active ingredient, the method of application, and environmental factors such as soil type, humidity, and temperature.

[0200] Useful dosage forms include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and / or suspensions), etc., which can optionally be thickened into a gel. Useful dosage forms also include solids such as powders, granules, tablets, pills, films, etc., which can be water-dispersible (“wettable”) or water-soluble. Active ingredients can be microencapsulated and re-formed into suspensions or solid dosage forms; alternatively, the entire dosage form of the active ingredient can be encapsulated. Encapsulation can control or delay the release of the active ingredient. Sprayable formulations can be diluted in a suitable medium, with a spray volume of approximately one hundred to several hundred liters per hectare. High-concentration compositions are primarily used as intermediates for further processing.

[0201] Typical solid diluents are described in Watkins et al., *Handbook of Insecticide Dust Diluents and Carriers*, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, *Solvents Guide*, 2nd Ed., Interscience, New York, 1950. McCutcheon's *Detergents and Emulsifiers Annual*, Allured Publ. Corp., Ridgewood, New Jersey, and *Sisely and Wood, Encyclopedia of Surface Active Agents*, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended applications. All formulations may contain small amounts of additives to reduce foaming, clumping, corrosion, microbial growth, etc., or thickeners to increase viscosity.

[0202] Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, sulfonated dialkyl succinate, alkyl sulfates, alkylbenzene sulfonates, organosilanes, N,N-dialkyl taurate, lignin sulfonates, naphthalene sulfonates with aldehyde condensates, polycarboxylate esters, and polyoxyethylene / polyoxypropylene block copolymers.

[0203] Solid diluents include, for example, clays such as bentonite, montmorillonite, magnesia and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate; liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfone, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffin, alkylbenzene, alkylnaphthalene, olive oil, castor oil, linseed oil, tung oil, sesame oil, corn oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil and cocoa butter, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, and dodecyl alcohol.

[0204] Solutions, including emulsifiable concentrates, can be prepared by simply mixing the components. Powders and fine powders can be prepared by mixing and, typically, by grinding in a hammer mill or hydraulic mill; suspensions are generally prepared by wet milling; granules and pellets, for example, US3060,084, are prepared by spraying the active ingredient onto freshly made granular carriers or by granulation techniques. See Browning, “Agglomeration,” Chemical Engineering, December 4, 1967, pp. 147-48; Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, Pages 8-57; and WO 91 / 13546. The preparation of pills is described in US4172714; water-dispersible and water-soluble granules are prepared by methods as described in US4144050, US3920442, and DE 3246493; and tablets are prepared by methods as described in US 5180587, US5232701, and US5208030. Films can be prepared by methods as described in GB2095558 and US3299566.

[0205] More information on the processing can be found in US 3,235,361; US ​​3,309,192; US 2,891,855; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York 1961, pp. 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

[0206] In this document, for certain applications of the composition, such as in agriculture, one, two or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers may be added to the insecticidal and / or acaricidal compositions of the present invention, thereby producing additional advantages and effects.

[0207] Beneficial effects

[0208] The compounds of formula (I) described in this invention exhibit excellent activity against a variety of pests and mites in agriculture and other fields. Furthermore, these compounds achieve good control effects at very low dosages. More importantly, their control effects are significantly superior to existing insecticides and / or acaricides, and therefore they can be used to prepare insecticides and / or acaricides.

[0209] Terminology Definitions and Explanations

[0210] Unless otherwise defined, all technical terms in this document have the same meanings as commonly understood by one of ordinary skill in the art to which the subject matter of the claims pertains. Unless otherwise stated, all patents, patent applications, and publications cited in this document are incorporated herein by reference in their entirety. If multiple definitions exist for terms in this document, the definitions in this chapter shall prevail.

[0211] Some groups in this application (e.g.) )middle The location indicates the connection point.

[0212] In this application, "more than" means three or more.

[0213] It should be understood that references (including Carey and Sundberg, "Advanced Organic Chemistry 4") may be included. THED."Vols.A(2000)and B(2001),Plenum Press,New Definitions of standard chemical terms can be found in the York ( ). Unless otherwise stated, conventional methods within the scope of the art, such as mass spectrometry, NMR, and pharmacological methods, are used. Unless specifically defined, the terms used herein in the relevant descriptions of analytical chemistry, organic synthetic chemistry, and pharmaceutical and medicinal chemistry are known in the art. Standard techniques can be used in chemical synthesis, chemical analysis, drug preparation, formulation and delivery, and in the treatment of patients. For example, reactions and purifications can be carried out using the manufacturer's instructions for use of kits, or in accordance with methods known in the art or the descriptions of this application. The techniques and methods described herein are generally carried out according to conventional methods well known in the art, based on the descriptions in several summary and more specific documents cited and discussed in this specification. In this specification, groups and their substituents can be selected by those skilled in the art to provide stable structural moieties and compounds. When a substituent is described by a conventional chemical formula written from left to right, the substituent also includes chemically equivalent substituents obtained when the structural formula is written from right to left, provided that they conform to the valence bond rules. For example, CH2O is equivalent to OCH2 and can be attached to the substitution position by an oxygen atom or a carbon atom of a methylene group.

[0214] The term "halogen" refers to fluorine, chlorine, bromine, or iodine.

[0215] The term “C1-C4 alkyl” should be understood to mean a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.

[0216] The term “C1-C6 alkyl” should be understood to mean a straight-chain or branched saturated monovalent hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, butyl, isopropyl, isobutyl, sec-butyl, and tert-butyl.

[0217] The above definition of the term "alkyl" also applies to other terms containing "C1-C4 alkyl", such as "C1-C4 alkoxy (C1-C4 alkyloxy)," "halogenated C1-C4 alkyl," "halogenated C1-C4 alkoxy," "C1-C4 alkyl thio," "(C1-C4) alkyl-SO-," "(C1-C4) alkyl-SO2-," "(C1-C4) haloalkyl sulfone-SO2-," etc.

[0218] The term "C3-C6 cycloalkyl" should be understood to refer to a saturated monovalent monocyclic or bicyclic hydrocarbon ring having 3 to 6 carbon atoms. In particular, the group has 3, 4, 5, or 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0219] Term "C" 2- "C4 alkenyl" should be understood to refer to a straight-chain or branched monovalent hydrocarbon group containing one or more double bonds and having 2 to 4 carbon atoms. It should be understood that when the alkenyl group contains more than one double bond, the double bonds may be separable or conjugated.

[0220] Term "C" 2- "C4 alkynyl" should be understood as representing a straight-chain or branched monovalent hydrocarbon group that contains one or more triple bonds and has 2 to 4 carbon atoms.

[0221] As used herein, the term "pharmaceutically acceptable salt" refers to a salt that retains the bioavailability of the free acid and free base of the specified compound and has no adverse effects in biological or other respects. The compounds in this application also include pharmaceutically acceptable salts, such as nitrates, hydrochlorides, sulfates, phosphates, acetates, trifluoroacetates, malates, or citrates, and other salts generally usable in the agricultural and horticultural fields. A pharmaceutically acceptable salt refers to a salt form obtained by converting a base group in a parent compound into a salt form. Pharmaceutically acceptable salts include, but are not limited to, inorganic or organic acid salts with base groups such as amine (amino) groups. The pharmaceutically acceptable salts of this application can be synthesized from the parent compound by reacting a basic group in the parent compound with 1-4 equivalents of an acid in a solvent system. Suitable salts are listed in Remingtong's Pharmaceutical Sciences, 17. th See, for example, hydrochloride, in Mack Publishing Company, Easton, Pa., 1985, p. 1418 and Journal of Pharmaceutical Science, 66, 2 (1977).

[0222] As used herein, “stereoisomers” refers to isomers resulting from different spatial arrangements of atoms in a molecule. Compounds of Formula (I) contain asymmetric or chiral centers, and therefore, different stereoisomers exist. All stereostructures and mixtures of Formula (I), including racemic mixtures, are included as part of this application. Diastereomeric mixtures can be separated into individual diastereomers based on their different physicochemical properties using well-known methods, such as the resolution of enantiomers by reacting them with a suitable optically active substance (e.g., a chiral alcohol or Mosher's chloride) to convert them to diastereomers, separating and converting them (e.g., hydrolysis) to the corresponding single isomer. Some compounds in Formula (I) may be transisomers (e.g., substituted aryl groups), which are also part of this application. Enantiomers can also be separated using chiral chromatographic columns. Compounds of Formula (I) may exist in different tautomeric forms, all of which are included within the scope of this application. For example, compounds in the keto-enol and imine-enamine forms. Detailed Implementation

[0223] The technical solution of the present invention will be further described in detail below with reference to specific embodiments. It should be understood that the following embodiments are merely illustrative and explanatory of the present invention, and should not be construed as limiting the scope of protection of the present invention. All technologies implemented based on the above content of the present invention are covered within the scope of protection intended by the present invention.

[0224] Unless otherwise stated, the raw materials and reagents used in the following examples are commercially available products or can be prepared by known methods.

[0225] The following LC-MS detection and analysis were performed under the following chromatographic conditions:

[0226] Column: Agilent ZORBAX SB-C18 150mm×4.6mm, 5μm (id);

[0227] Detection wavelength: 254 nm; Flow rate: 0.8 mL / min; Column temperature: 30 °C;

[0228] Gradient elution conditions:

[0229]

[0230]

[0231] Synthesis Examples

[0232] Example 1: Preparation of 2-chloro-N-(cyanomethyl)-N-cyclopropyl-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-amide)benzamide (compound 2)

[0233] 1. Preparation of 5-amino-2-chloro-N-(cyanomethyl)-N-cyclopropylbenzamide

[0234]

[0235] Step 1: Preparation of 2-chloro-N-(cyanomethyl)-N-cyclopropyl-5-nitrobenzamide: At 0°C, 1.61 g (0.008 mol) of 2-chloro-5-nitrobenzic acid, 2.06 g (0.016 mol) of di(isopropyl)ethylamine, and 4.58 g (0.0088 mol) of benzotriazol-1-yl-oxytripyrrolidine phosphoric acid hexafluorophosphate were dissolved sequentially in 50 mL of dichloromethane. The reaction mixture was stirred for 2 hours. At room temperature, 0.92 g (0.0096 mol) of 2-(cyclopropylamino)acetonitrile was added to the above solution. Stirring was continued at room temperature for 10 hours. 30 mL of water was added to the reaction system, and the phases were separated. The aqueous phase was extracted twice with dichloromethane. The organic phases were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The organic phase was desolvated under reduced pressure and subjected to column chromatography (eluent: V). 乙酸乙酯：石油醚 =1:4) yielded 1.93g of product, with a yield of 86%.

[0236] LC-MS[M+H] + =280.05, [M+Na] + =302.03, [M+K] + =318.

[0237] Step 2: Preparation of 5-amino-2-chloro-N-(cyanomethyl)-N-cyclopropylbenzamide: At room temperature, 1.86 g (0.0067 mol) of 2-chloro-N-(cyanomethyl)-N-cyclopropyl-5-nitrobenzamide and 5.12 g (0.027 mol) of anhydrous stannous chloride were added sequentially to 25 mL of 1,4-dioxane, followed by slow dropwise addition of 7 mL of concentrated hydrochloric acid. After the addition was complete, the reaction solution was heated to 60–65 °C and reacted for 2.5 h. Heating was stopped, and after the reaction solution cooled to room temperature, 4 M sodium hydroxide aqueous solution was added to adjust the pH to 10. The reaction solution was filtered through diatomaceous earth, and the filtrate on the diatomaceous earth was washed with ethyl acetate. The filtrate was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. Column chromatography was then performed (eluent: V). 乙酸乙酯：石油醚 =1:3) yielded 1.06g of product, with a yield of 63%.

[0238] LC-MS[M+H] + =250.08, [M+Na] + =272.06, [M+K] + =288.03.

[0239] 2. Preparation of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-acyl chloride

[0240]

[0241] Step 1: Preparation of 1,3-dichloro-5-(3,3-diethoxyprop-1-en-1-yl)benzene: At room temperature, 1.58 g (0.015 mol) of triethyl orthoformate and 0.018 g (0.07 mmol) of pyridine 4-methylbenzenesulfonic acid were added sequentially to a solution of 1.43 g (0.007 mol) of 3-(3,5-dichlorobenzene)propenal in 15 mL of anhydrous ethanol. The reaction mixture was stirred for 20 h. 5 mL of saturated sodium carbonate aqueous solution was added to the reaction mixture, and the ethanol was removed by vacuum distillation. The concentrate was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 1.83 g of product (95% yield).

[0242] LC-MS[M+H] + =275.06, [M+Na] + =297.04, [M+K] + =313.01.

[0243] Second step reaction: Preparation of 1,3-dichloro-5-(2,2-dichloro-3-(diethoxymethyl)cyclopropane)benzene: At room temperature, 0.34 g (0.88 mmol) tetrabutylammonium hexafluorophosphate was added sequentially to a solution of 1.80 g (0.0065 mmol) 1,3-dichloro-5-(3,3-diethoxyprop-1-en-1-yl)benzene in 12 mL of chloroform. 9 mL of 50% sodium hydroxide aqueous solution was slowly added dropwise to the above reaction solution. The reaction solution was stirred for 36 h. The reaction solution was filtered through diatomaceous earth, and the filtrate on the diatomaceous earth was washed with dichloromethane. The filtrate was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 1.58 g of product, with a yield of 68%.

[0244] LC-MS[M+H] + =357, [M+Na] + =378.98, [M+K] + =394.95.

[0245] Step 3: Preparation of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxaldehyde: 7 mL of 3M hydrochloric acid solution was added to 1.50 g (0.0041 mmol) of 1,3-dichloro-5-(2,2-dichloro-3-(diethoxymethyl)cyclopropane)benzene in 25 mL of acetone. The reaction mixture was stirred for 24 h. The reaction mixture was diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 0.83 g of product, yield 71%.

[0246] LC-MS[M+H] + =282.93, [M+Na] + =304.91, [M+K] +=320.88.

[0247] Step 4: Preparation of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxylic acid: At 0°C, 2.18 g (0.028 mol) of 2-methyl-2-butene was added to 0.80 g (0.0028 mol) of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxaldehyde in 15 mL of tetrahydrofuran solution. A mixture of 0.76 g (0.0084 mol) of sodium chlorite in 8 mL of water and a mixture of 1.52 g (0.011 mol) of potassium dihydrogen phosphate in 10 mL of water were slowly added dropwise to the above reaction solution. After the addition was complete, the mixture was allowed to react at room temperature for 22 h. The pH of the reaction solution was adjusted to acidity by adding 2M hydrochloric acid aqueous solution. The mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated residue was adjusted to alkaline pH with 1M sodium hydroxide aqueous solution, washed with water and the organic phase was separated. The aqueous phase was adjusted to acidic pH with 2M hydrochloric acid aqueous solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain 0.57 g of product, with a yield of 68%.

[0248] LC-MS[M+H] + =298.92, [M+Na] + =320.9, [M+K] + =336.87.

[0249] Step 5: Preparation of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-acyl chloride: 0.30 g (1.0 mmol) of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxylic acid, 0.24 g (2.0 mmol) of thionyl chloride, and a catalytic amount of N,N-dimethylformamide (2 drops) were added sequentially to 15 mL of toluene. The reaction solution was refluxed for 2 h. Heating was stopped, and after the reaction solution cooled to room temperature, toluene and thionyl chloride were removed by vacuum distillation to obtain 0.31 g of the product. Yield: 96%.

[0250] 3. Preparation of 2-chloro-N-(cyanomethyl)-N-cyclopropyl-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-amide)benzamide (compound 2)

[0251]

[0252] 0.25 g (1.0 mmol) of 5-amino-2-chloro-N-(cyanomethyl)-N-cyclopropylbenzamide and 0.33 g (1.05 mmol) of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-acyl chloride were added sequentially to 15 mL of toluene. The reaction mixture was refluxed for 2 h. Heating was stopped, and the reaction mixture was allowed to cool to room temperature. The mixture was washed with saturated sodium bicarbonate aqueous solution, and the phases were separated. The organic phase was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. Column chromatography was then performed (eluent: V). 乙酸乙酯：石油醚 The product yield was 0.39g with a ratio of 1:3, representing a yield of 75%.

[0253] LC-MS[M+H] + =529.98, [M+Na] + =551.96, [M+K] + =567.93.

[0254] 1 H-NMR (400MHz, CDCl3) δ9.41(s,1H),7.74(d,1H),7.36(m,2H),7.24(s,1H),7.22(m,2H),4.49(s,2H),3.51(d,1H),2.94(m,2H),0.69(m,4H).

[0255] Example 2: Preparation of 2-chloro-N-(cyanomethyl)-N-cyclopropyl-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-amide)benzamide (compound 62)

[0256]

[0257] 0.25 g (1.0 mmol) of 5-amino-2-chloro-N-(cyanomethyl)-N-cyclopropylbenzamide and 0.37 g (1.05 mmol) of 2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-acyl chloride were added sequentially to 15 mL of toluene. The reaction mixture was refluxed for 2 h. Heating was stopped, and the reaction mixture was allowed to cool to room temperature. The mixture was washed with saturated sodium bicarbonate aqueous solution, and the phases were separated. The organic phase was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. Column chromatography was then performed (eluent: V). 乙酸乙酯：石油醚 =1:3) yielded 0.43g of product, with a yield of 76%.

[0258] LC-MS[M+H] + =563.94, [M+Na] + =585.92, [M+K] + =601.89.

[0259] 1H-NMR (400MHz, CDCl3) δ9.09(s,1H),7.74(d,1H),7.37(m,3H),7.13(d,1H)4.49(s,2H),3.50(d,1H),3.00(m,1H),2.88(d,1H),0.70(m,4H).

[0260] Example 3: Preparation of N-(cyanomethyl)-N-(cyclopropyl)-3-(2,2-dichloro-N-methyl-3-(3,4,5-trichlorophenyl)cyclopropane-1-amide)-2-fluorobenzamide (compound 81)

[0261]

[0262] Step 1: Preparation of N-(cyanomethyl)-N-(cyclopropyl)-2-fluoro-3-(methylamine)benzamide: At 0°C, 12 mL of 37% formaldehyde aqueous solution was slowly added dropwise to 2.30 g (10.07 mmol) of 3-amino-N-(cyanomethyl)-N-(cyclopropyl)-2-fluorobenzamide in 18 mL of concentrated sulfuric acid solution, maintaining the reaction solution temperature between 30 and 35°C during the addition. After the addition was complete, the temperature was raised to 40°C and the reaction was allowed to proceed for 2 hours. Heating was then stopped, and the reaction solution was allowed to cool to room temperature. The solution was then poured into ice water, and the pH was adjusted to 10 with 4M sodium hydroxide aqueous solution. A solid precipitated in the mixed solution; this was filtered and washed with water. The obtained solid was pulped with petroleum ether, filtered, washed with cold petroleum ether, and dried to obtain 2.36 g of product, with a yield of 95%.

[0263] LC-MS[M+H] + =248.12, [M+Na] + =270.1, [M+K] + =286.07.

[0264] Step 2: Preparation of N-(cyanomethyl)-N-(cyclopropyl)-3-(2,2-dichloro-N-methyl-3-(3,4,5-trichlorophenyl)cyclopropane-1-amide)-2-fluorobenzamide: 0.25 g (1.0 mmol) of N-(cyanomethyl)-N-(cyclopropyl)-2-fluoro-3-(methylamine)benzamide and 0.37 g (1.05 mmol) of 2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-acyl chloride were added sequentially to 15 mL of toluene. The reaction solution was refluxed for 4 h. Heating was stopped, and after the reaction solution cooled to room temperature, it was washed with saturated sodium bicarbonate aqueous solution, the phases were separated, the organic phase was washed with water, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, the solvent was removed by vacuum distillation, and column chromatography was performed (eluent: V). 乙酸乙酯：石油醚 The product yield was 0.39g with a ratio of 1:3, representing a yield of 69%.

[0265] LC-MS[M+H] + =561.98, [M+Na] + =583.96, [M+K] + =599.93.

[0266] 1 H-NMR(400MHz, CDCl3)δ9.09(s,1H),7.74(d,1H),7.37(m,3H),7.13(d,1H)4 .49(s,2H),3.50(d,1H),3.42(s,3H),3.00(m,1H),2.88(d,1H),0.70(m,4H).

[0267] Example 4: Preparation of 2-chloro-N-(cyanomethyl)-N-(cyclopropylmethyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-amide)benzamide (compound 652)

[0268]

[0269] 0.27 g (1.0 mmol) of 5-amino-2-chloro-N-(cyanomethyl)-N-(cyclopropylmethyl)benzamide and 0.37 g (1.05 mmol) of 2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-acyl chloride were added sequentially to 15 mL of toluene. The reaction mixture was refluxed for 2 h. Heating was stopped, and the reaction mixture was allowed to cool to room temperature. The mixture was washed with saturated sodium bicarbonate solution, and the phases were separated. The organic phase was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. Column chromatography was then performed (eluent: V). 乙酸乙酯：石油醚 =1:3) yielded 0.44g of product, with a yield of 75%.

[0270] LC-MS[M+H] + =577.96, [M+Na] + =599.94, [M+K] + =615.91.

[0271] 1 H-NMR(400MHz, CDCl3)δ9.54(d,1H),7.83(d,1H),7.33(m,4H),7.15(d,1H),4.64(m ,2H),3.48(d,1H),3.32(m,1H),2.92(d,1H),1.04(m,2H),0.73(m,1H),0.30(m,2H).

[0272] Example 5: Preparation of 2-chloro-N-cyclopropyl-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-amide)-N-(2,2,2-trifluoroethyl)benzamide (compound 663)

[0273]

[0274] 0.30 g (1.0 mmol) of 5-amino-2-chloro-N-cyclopropyl-N-(2,2,2-trifluoroethyl)benzamide and 0.33 g (1.05 mmol) of 2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-acyl chloride were added sequentially to 15 mL of toluene. The reaction mixture was refluxed for 2 h. Heating was stopped, and the reaction mixture was allowed to cool to room temperature. The mixture was washed with saturated sodium bicarbonate aqueous solution, and the phases were separated. The organic phase was washed with water, extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation. Column chromatography was then performed (eluent: V). 乙酸乙酯：石油醚 The product yield was 0.41g (1:3 ratio), with a yield of 71%.

[0275] LC-MS[M+H] + =572.97, [M+Na] + =594.95, [M+K] + =610.92.

[0276] 1 H-NMR (400MHz, CDCl3) δ9.41(s,1H),7.74(d,1H),7.36(m,2H),7.26(s,1H),7.23(m,2H),4.49(s,2H),3.55(d,1H),2.96(m,2H),0.69(m,4H).

[0277] The present invention also synthesized the following compounds with reference to the methods in the above embodiments:

[0278] Table 3

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302] Formulation Examples

[0303] In the following examples, all percentages are by weight, and all dosage forms were prepared using conventional methods.

[0304] Example 6:

[0305] This embodiment uses the compound obtained in the above embodiment to prepare a wettable powder, specifically using the following raw material composition ratio:

[0306] The present invention comprises 50.0% compound, 4.0% dodecylphenol polyethoxyethylene glycol ether, 6.0% sodium lignosulfonate, 8.0% sodium aluminosilicate, and 32.0% montmorillonite (calcined).

[0307] Example 7:

[0308] This embodiment uses the compound obtained in the above embodiment to prepare granules, specifically using the following raw material composition ratio:

[0309] The present invention comprises 20.0% compound, 2.0% sodium dodecyl sulfate, 6.0% calcium lignosulfonate, 10.0% potassium chloride, 1.0% polydimethylsiloxane, and soluble starch to make up to 100%.

[0310] Example 8:

[0311] This embodiment uses the compound obtained in the above embodiment to prepare extruded pellets, specifically using the following raw material composition ratio:

[0312] The present invention comprises 30.0% of the compound, 9.0% of anhydrous calcium sulfate, 4.0% of crude lignin sulfonate calcium, 1.0% of sodium alkyl naphthalene sulfonate, and 56.0% of calcium and magnesium bentonite.

[0313] Example 9:

[0314] This embodiment uses the compound obtained in the above embodiment to prepare an emulsifiable concentrate, specifically using the following raw material composition ratio:

[0315] The present invention comprises 25.0% compound, 60% solvent 150, 5% PEG400, 3% calcium dodecylbenzenesulfonate, and 7% (Z)-9-octadecenoimino bis-2,1-ethylenedimethylethylene oxide.

[0316] Example 10:

[0317] This embodiment uses the compound obtained in the above embodiment to prepare an aqueous suspension, specifically using the following raw material composition ratio:

[0318] The present invention comprises 30.0% of the compound, 5.0% of POE (polystyrene phenyl ether sulfate), 0.5% of xanthan gum, 5% of polyethylene glycol, 1% of triethanolamine, 0.5% of sorbitol, and water to a total of 100.0%.

[0319] Bioactivity assay

[0320] Example 11:

[0321] 1. Insecticidal activity assay

[0322] In this embodiment, the insecticidal activity of the compounds prepared in the above embodiments was tested on several insects.

[0323] Insecticidal activity assay: The test method is as follows: the sample of the compound to be tested is dissolved in a suitable solvent (the type of solvent is such as acetone, methanol, DMSO, etc., and the solvent is selected according to its solubility in the sample) to prepare a test solution of the required concentration. The test unit consists of a small open container containing 12-15 day old radish plants. The plant is pre-infected by placing 30-40 pests located on a leaf cut from a cultivated plant (leaf cutting method) on a leaf of the test plant. As the leaf dehydrates, the pests move on the test plant. After pre-infection, the soil of the test unit is covered with a layer of sand.

[0324] The test method is as follows: The test was repeated three times. After spraying the prepared test compound, each test unit was allowed to dry for 1 hour, and then a black net cover was placed on top. The test units were kept in a growth chamber at 25°C and 70% relative humidity for 6 days. The insect mortality rate (lethality rate) of each test unit was then visually evaluated. The lethality rate was calculated as follows:

[0325]

[0326] (1) Exemplary embodiment: Test results of compound control of western flower thrips

[0327] Compounds with a lethality of over 80% against western flower thrips at a dose of 25 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 60 5, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0328] Compounds with a lethality of over 80% against western flower thrips at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 21 3, 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 753, 758, 760, 763, 771, 775, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0329] Compounds with a lethality of over 80% against western flower thrips at a dose of 1 ppm include: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 60 4, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740 742, 745, 746, 753, 758, 760, 763, 771, 775, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0330] (2) Test results of compounds used to control diamondback moth in exemplary embodiments

[0331] The compounds with a lethality of over 80% against diamondback moth at a dose of 10 ppm are: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 214. 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0332] Compounds with a lethality of over 80% against diamondback moth at a dose of 1 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 60 4, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740 742, 745, 746, 748, 753, 758, 760, 763, 775, 776, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0333] The compounds that, at a dose of 0.1 ppm, have a lethality of over 80% against diamondback moth include: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 60 3, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 7 35, 740, 742, 745, 746, 748, 753, 758, 760, 763, 776, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0334] (3) Exemplary Examples: Test Results of Compound Control of Cabbage White Butterfly

[0335] Compounds with a lethality of over 80% against the cabbage white butterfly at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 21 4, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0336] Compounds with a lethality of over 80% against the cabbage white butterfly at a dose of 1 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 7 42, 745, 746, 748, 753, 758, 760, 763, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0337] The compounds that have a lethality of over 80% against the cabbage white butterfly at a dose of 0.1 ppm are: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 6 04, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 748, 753, 758, 760, 763, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0338] (4) Exemplary Examples: Compound Control of Armyworm Test Results

[0339] Compounds with a lethality of over 80% against armyworms at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, and 214. 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0340] Compounds with a lethality of over 80% against armyworms at a dose of 1 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735 740, 742, 745, 746, 748, 753, 758, 760, 763, 775, 776, 780, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0341] The compounds that, at a dose of 0.1 ppm, have a lethality of over 80% against armyworms are: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735 740, 742, 745, 746, 748, 753, 758, 760, 763, 775, 776, 780, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0342] (5) Exemplary Examples: Test Results of Compound Control of Spodoptera litura

[0343] Compounds with a lethality of over 80% against *Spodoptera litura* at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 60 5, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0344] Compounds with a lethality of over 80% against *Spodoptera litura* at a dose of 1 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 21 3, 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735 740, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0345] The compounds that, at a dose of 0.1 ppm, have a lethality of over 80% against *Spodoptera litura* are: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 21 3, 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735 740, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0346] (6) Test results of the compound for controlling rice stem borer in exemplary embodiments

[0347] Compounds with a lethality of over 80% against rice stem borer at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 21 4, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0348] Compounds with a lethality of over 80% against rice stem borer at a dose of 5 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 6 04, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 780, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0349] Compounds with a lethality of over 80% against rice stem borer at a dose of 1 ppm include: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 60 4, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 780, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0350] (7) Test results of the compound for controlling rice leaf roller in exemplary embodiments

[0351] Compounds with a lethality of over 80% against rice leaf roller at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 60 5, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0352] Compounds with a lethality of over 80% against rice leaf roller at a dose of 5 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 21 3, 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0353] Compounds that, at a dose of 1 ppm, have a lethality of over 80% against the rice leaf roller include: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 6 04, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0354] (8) Exemplary Examples: Compound Test Results for Flea Beetle Control

[0355] Compounds with a lethality of over 80% against flea beetles at a dose of 25 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, and 214. 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0356] Compounds with a lethality of over 80% against flea beetles at a dose of 10 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 6 04, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 74 0, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0357] Compounds with a lethality of over 80% against flea beetles at a dose of 1 ppm include: 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 21 4, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 781, 789, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0358] 2. Acaricide activity assay

[0359] In this embodiment, the compounds prepared in the above embodiments were used to conduct acaricidal activity tests on several mite pests.

[0360] The testing method is as follows: Dissolve the sample of the compound to be tested in a suitable solvent (the type of solvent is such as acetone, methanol, DMSO, etc., and the solvent is selected according to its solubility in the sample) to prepare a test solution of the required concentration. Cut double-sided tape into 2-3 cm lengths and attach them to one end of a microscope slide. Use tweezers to peel off the paper off the tape. Use a size 0 brush to select female adult mites that are uniform in size, brightly colored, and active. Stick their backs onto the double-sided tape (Note: Do not stick the mite legs, antennae, and mouthparts). Stick 4 rows per tape, with 10 mites per row.

[0361] The test method is as follows: The test was repeated three times. After 4 hours in a biochemical incubator at approximately (25±1)℃ and 85% relative humidity, the mites were observed using a binocular microscope, and dead or inactive individuals were removed. One end of a slide containing mites was immersed in the drug solution, gently shaken for 5 seconds, and then removed. Excess drug solution was quickly absorbed from the mites and surrounding area using absorbent paper. The slide was placed in the aforementioned biochemical incubator, and after 24 hours, the results were examined using a binocular microscope. The mites were gently touched with a brush; those whose legs did not move were considered dead. The mortality rate was calculated. The mortality rate was calculated as follows:

[0362]

[0363] The results of partial testing of Tetranychus cinnabarinus are as follows:

[0364] Compounds with a lethality of over 80% against *Tetranychus carmine* at a dose of 25 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213, 2 14, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 60 5, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 806, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0365] The compounds that, at a dose of 10 ppm, have a lethality of over 80% against the carmine spider mite are: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604, 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 742, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 789, 800, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882;

[0366] Compounds with a lethality of over 80% against *Tetranychus carinii* at a dose of 1 ppm include: 1, 2, 3, 4, 6, 7, 17, 32, 36, 47, 61, 62, 63, 64, 66, 67, 77, 81, 91, 92, 93, 96, 106, 107, 121, 122, 124, 126, 136, 137, 138, 139, 152, 157, 167, 181, 182, 183, 184, 186, 187, 196, 197, 201, 211, 212, and 213. 214, 226, 227, 231, 241, 242, 243, 244, 246, 257, 258, 261, 271, 272, 276, 287, 301, 302, 304, 306, 361, 362, 363, 366, 377, 422, 423, 424, 426, 481, 482, 484, 486, 497, 501, 512, 516, 542, 543, 544, 546, 547, 557, 558, 561, 602, 603, 604 605, 608, 611, 614, 620, 623, 624, 626, 629, 632, 638, 640, 645, 652, 653, 656, 663, 665, 666, 670, 672, 674, 676, 677, 679, 681, 686, 688, 691, 692, 694, 698, 699, 704, 706, 709, 710, 712, 717, 722, 724, 727, 728, 730, 731, 735, 740, 7 42, 745, 746, 748, 753, 758, 760, 763, 770, 771, 775, 776, 780, 781, 800, 811-1, 812-1, 814-1, 815-1, 817-1, 818-1, 820-1, 821-1, 823-1, 824-1, 811, 813, 814, 815, 816, 818, 819, 821, 823, 832, 841, 853, 863, 868, 871, 878, 881, 882.

[0367] 3. Test results of exemplary embodiment compounds and control reagents

[0368] This embodiment conducted an activity comparison test between the exemplary compound and the control agent (compounds CK1 and CK2 are compounds numbered F66 and F69 in patent document WO2016168058, and these two compounds were prepared according to the method reported in the literature).

[0369] The test results are shown in Table 4 below.

[0370]

[0371] Table 4

[0372]

[0373] In addition to the compounds listed in the table above, the compounds of other exemplary embodiments of the present invention exhibit superior control activity against pests and mites compared to the control agents. Therefore, the compounds of formula (I) of the present invention show excellent activity against a variety of pests and mites in the agricultural field.

[0374] The embodiments of the present invention have been described above. However, the present invention is not limited to the above embodiments. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. The compound represented by formula (I) or a pharmaceutically acceptable salt thereof, wherein, The compound represented by formula (I) is selected from the following compounds: (I) Where R1=H, R5=H, R8=H, R9=H, R 11 =H、R 12 =H, Q1=O, Q2=O; Alternatively, it can be selected from the following compounds: Among them, R6=Cl, R7=Cl, R8=H, R9=H, Q1=O, and Q2=O.

2. A pesticide composition, characterized in that, The pesticide composition comprises one, two, or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof as active ingredients.

3. Use as a pesticide of one, two, or more of the compounds of formula (I) of claim 1 or their pharmaceutically acceptable salts.

4. Use as an insecticide of one, two or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof.

5. Use of one, two, or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof as acaricides.

6. Use of one, two or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof in the preparation of pesticides.

7. Use of one, two or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof in the preparation of insecticides.

8. Use of one, two or more of the compounds of formula (I) of claim 1 or pharmaceutically acceptable salts thereof in the preparation of acaricides.

9. A method for controlling pests or mites, characterized in that, The method comprises applying one, two, or more of the compound of formula (I) of claim 1 or a pharmaceutically acceptable salt thereof, or applying the composition of claim 2 to a growth medium of pests or mites.

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