Sulfone compound as well as preparation method and application thereof

Abstract

The invention belongs to the field of agricultural insecticides, and particularly relates to a sulfone compound as well as a preparation method and application thereof. The sulfone compound as shown in the formula I is synthesized, has good insecticidal activity on prodenia litura, spodoptera litura and beet armyworm, has no obvious inhibition effect on growth of traditional Chinese medicinal plants, and can be used as an insecticide. The skeleton of the novel sulfone compound provided by the invention is different from that of traditional commercially available botanical insecticides, and the novel sulfone compound is novel in structure, can be applied to planting of traditional Chinese medicinal materials and agricultural industry, solves the problems of insect pests and insect resistance, and provides a new choice for protection of traditional Chinese medicinal materials and research, development and application of agricultural chemicals. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the field of agricultural pesticides, and in particular relates to a sulfone compound, a preparation method and application thereof. Background Art

[0002] Agricultural pests directly damage plants by chewing leaves, sucking sap, gnawing on roots and stems, resulting in decreased yields or even total failure of crops or Chinese medicinal materials. They also spread bacteria, fungi and other pathogens, affecting plant health and causing serious damage to the ecosystem. Taking effective pest management measures is an important means to ensure the sustainable development of agriculture and the quality and safety of Chinese medicinal materials.

[0003] Sulfone compounds are an important class of active substances in the pesticide and pharmaceutical fields. These compounds possess broad-spectrum biological activities, such as insecticides, fungicides, and herbicides, and have demonstrated significant application value in agriculture. For example, a Japanese agricultural chemical company has reported the development of a new insecticide, flubendiamide, which belongs to the phthalamide sulfone family. Its first target is an inhibitor of the ryanodine receptor, showing excellent activity against lepidopteran pests, such as cotton bollworms. Aventis has developed the sulfoxide insecticide fipronil, which exhibits broad-spectrum, high-efficiency activity against aphids, leafhoppers, lepidopteran larvae, flies, and coleopteran pests. Furthermore, Aventis has developed ethiprole, also a sulfoxide insecticide. While existing insecticides have some insecticidal efficacy, they suffer from numerous environmental, health, and ecological drawbacks. Therefore, there is an urgent need to develop insecticides with novel structures to address insect pests and insect resistance. Summary of the Invention

[0004] In view of the problems of the prior art, the present invention provides a sulfone compound and a preparation method and use thereof.

[0005] The present invention provides a compound represented by Formula I, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof:

[0006]

[0007] wherein R is selected from hydrogen, halogen, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 20 Aryl, wherein the substituent is selected from halogen;

[0008] n is selected from 0, 1, 2, 3, 4, 5.

[0009] Preferably, R is selected from halogen, substituted or unsubstituted C1-C4 alkyl, cyclohexyl, substituted or unsubstituted C6 aryl, wherein the substituent is selected from halogen;

[0010] n is selected from 1, 2, and 3.

[0011] Preferably, R is selected from cyclohexyl and phenyl;

[0012] n is selected from 1.

[0013] Preferably, the compound represented by formula I is one of the following structures:

[0014]

[0015]

[0016]

[0017] The present invention also provides a method for preparing the above-mentioned compound, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof, comprising the following steps:

[0018]

[0019] Step 1, reacting compound a with pentafluorobenzoyl chloride to obtain compound b;

[0020] Step 2, subjecting compound b to a reduction reaction to obtain compound c;

[0021] Step 3, reacting compound c with thiol to obtain compound d;

[0022] Step 4, reacting compound d with compound e to obtain a compound represented by formula I;

[0023] The selection of R and n is as described above.

[0024] Preferably, in step 1, the solvent of the reaction is selected from at least one of dichloromethane and chloroform;

[0025] And / or, in step 1, the reaction is carried out under the action of a catalyst, and the catalyst is selected from aluminum chloride;

[0026] And / or, in step 1, the reaction is carried out in an ice bath for 20-40 minutes, followed by reaction at 20-30° C. for 2-4 hours;

[0027] And / or, in step 2, the solvent of the reaction is selected from at least one of tetrahydrofuran and methanol;

[0028] And / or, in step 2, the reducing agent of the reduction reaction is selected from sodium borohydride;

[0029] And / or, in step 2, the reaction time of the reduction reaction is 2-4 hours;

[0030] And / or, in step 3, the solvent of the reaction is selected from chloroform;

[0031] And / or, in step 3, the reaction is carried out under the action of a catalyst, the catalyst being selected from zinc chloride;

[0032] And / or, in step 3, the reaction time is 2-4 days;

[0033] And / or, in step 4, the solvent of the reaction is selected from dichloromethane;

[0034] And / or, in step 4, the reaction is carried out under the action of a catalyst, and the catalyst is selected from aluminum chloride;

[0035] And / or, in step 4, the reaction time is 2-10 min.

[0036] The present invention also provides use of the above-mentioned compound, or its salt, or its solvate, or its stereoisomer, or its geometric isomer, or its isotope-labeled substance, or its crystal form in the preparation of insecticides.

[0037] Preferably, the insecticide can control pests of the family Noctuidae of the order Lepidoptera.

[0038] Preferably, the pests of the family Noctuidae of the order Lepidoptera include at least one of the following: Spodoptera litura, Spodoptera frugiperda, and Spodoptera exigua.

[0039] The present invention also provides an insecticide, which is a preparation prepared with the above compound, or its salt, or its solvate, or its stereoisomer, or its geometric isomer, or its isotope-labeled substance, or its crystal form as the active ingredient.

[0040] The compounds and derivatives provided herein can be named according to the IUPAC (International Union of Pure and Applied Chemistry) or CAS (Chemical Abstracts Service, Columbus, OH) nomenclature system.

[0041] Definitions of terms used in the present invention: Unless otherwise stated, the initial definitions provided for groups or terms in this document apply to the groups or terms throughout the specification; for terms that are not specifically defined herein, they should be given the meaning that a person skilled in the art would give them based on the disclosure and context.

[0042] "Substitution" refers to the replacement of a hydrogen atom in a molecule by another different atom or molecule.

[0043] The minimum and maximum carbon atom content in a hydrocarbon group is indicated by a prefix, for example, the prefix C a -C b Alkyl refers to any alkyl group containing from "a" to "b" carbon atoms. Thus, for example, "C1-C6 alkyl" refers to an alkyl group containing from 1 to 6 carbon atoms.

[0044] "Alkyl" refers to a saturated hydrocarbon chain with a specified number of member atoms. For example, C1-C6 alkyl refers to an alkyl group with 1 to 6 member atoms, such as 1 to 4 member atoms. The alkyl group can be straight or branched. Representative branched alkyl groups have one, two or three branches. The alkyl group may optionally be substituted with one or more substituents as defined herein. Alkyl includes methyl, ethyl, propyl (n-propyl and isopropyl), butyl (n-butyl, isobutyl and tert-butyl), pentyl (n-pentyl, isopentyl and neopentyl) and hexyl. The alkyl group may also be part of other groups, such as C1-C6 alkoxy.

[0045] "Cycloalkyl" refers to a saturated or partially saturated cyclic group having from 3 to 10 carbon atoms and no ring heteroatoms, and having a single ring or multiple rings (including fused, bridged, and spiro ring systems).

[0046] "Halogen" is fluorine, chlorine, bromine or iodine.

[0047] "Haloalkyl" refers to an alkyl group in which the hydrogen atoms are replaced by one or more halogen atoms. For example, a C1-C6 haloalkyl group refers to an alkyl group containing 1 to 6 carbon atoms in which the hydrogen atoms are replaced by one or more halogen atoms.

[0048] "Aryl" refers to a functional group or substituent formed by removing a hydrogen atom from an aromatic compound, for example, phenyl.

[0049] In certain embodiments, one or more compounds of the present invention may be used in combination with each other, or optionally with any other active agent, to prepare a pesticide.

[0050] The sulfone compounds prepared by the present invention have good insecticidal activity against the armyworm, fall armyworm and beet armyworm, and have no obvious inhibitory effect on the growth of Chinese medicinal plants. They can be used as insecticides in Chinese medicinal plant planting and agricultural industries to solve insect pest and insect resistance problems, providing new options for the protection of Chinese medicinal materials and the research and development and application of agricultural chemicals.

[0051] Obviously, based on the above contents of the present invention, according to common technical knowledge and customary means in this field, without departing from the above basic technical ideas of the present invention, other various forms of modifications, replacements or changes can be made.

[0052] The following further describes the above content of the present invention in detail through specific embodiments in the form of examples. However, this should not be construed as limiting the scope of the above subject matter of the present invention to the following examples. All technologies implemented based on the above content of the present invention fall within the scope of the present invention. DETAILED DESCRIPTION

[0053] In the following examples and experimental examples, reagents and raw materials not specifically described are all commercially available.

[0054] Example 1 Sulfone compounds and preparation methods thereof

[0055] The synthetic route of sulfone compounds of the present invention is as follows:

[0056]

[0057] Preparation method:

[0058] Step 1: In a 100 ml round-bottom flask, 1 mmol of compound a and 3 mmol of aluminum chloride were dissolved in 20 ml of dichloromethane under an ice bath, and 3 mmol of pentafluorobenzoyl chloride was added dropwise. After stirring for 30 min, the ice bath was removed and the reaction was carried out at room temperature for 3 h. After the reaction was completed, 20 ml of ice-cold distilled water was added and stirred for 30 min. The mixture was extracted three times with ethyl acetate, the organic phase was collected, the solvent was removed under reduced pressure, and the mixture was purified by column chromatography with an eluent of petroleum ether: ethyl acetate 15:1→6:1 to obtain compound II as white crystals with a yield of 79%.

[0059] Step 2: In a 100 ml round-bottom flask, 1 mmol of compound b was dissolved in 20 ml of THF and 1 ml of methanol. 5 mmol of NaBH4 was added in portions. After reacting for 3 h, the product was purified by column chromatography with an eluent of petroleum ether:ethyl acetate (10:1 → 4:1) to obtain compound c as white crystals in a yield of 94%.

[0060] Step 3: In a 100 ml round-bottom flask, 1 mmol of compound III was dissolved in 20 ml of CHCl3, and 50 mmol of ZnCl2 and 50 mmol of thiol were added. After reacting for 3 days, the product was purified by column chromatography with an eluent of petroleum ether:ethyl acetate 200:1→60:1 to obtain compound d.

[0061] Step 4: In a 100 ml round-bottom flask, dissolve 1 mmol of compound d in 20 ml of CH2Cl2, add 10 mmol of AlCl3 and 10 mmol of compound e, react for 5 min, and purify by column chromatography using a mixture of petroleum ether:ethyl acetate (10:1 → 8:1) as eluent to obtain a sulfone compound (Formula I). wherein R is selected from hydrogen, halogen, substituted or unsubstituted C1-C4 alkyl, cyclohexyl, or phenyl, and wherein the substituent is selected from halogen;

[0062] n is selected from 1, 2, and 3.

[0063] Example 2 Compound W-1

[0064]

[0065] According to the preparation method of Example 1, wherein R is 4-methyl.

[0066] 1 H NMR (400MHz, Acetone-d6) δ11.09(s,1H),7.57–7.48(m,2H),7.30–7.23(m,2H),7.20(d,J=2.4Hz,1H),6.97(q,J=1.8Hz,1H),5.85(s,1H),3.65(s,3H). 19 F NMR (376MHz, Acetone) δ-138.15,-154.89,-163.89.

[0067] Example 3 Compound W-2

[0068]

[0069] According to the preparation method of Example 1, wherein R is 3-Cl or 4-F.

[0070] 1 H NMR (400MHz, Acetone-d6) δ11.33(s,1H),7.96(dd,J=6.8,2.3Hz,1H),7.79(ddd,J=8.7,4.4,2 .3Hz,1H),7.54(t,J=8.8Hz,1H),7.36(s,1H),7.12(t,J=2.0Hz,1H),6.19(s,1H),3.80(s,3H).

[0071] Example 4 Compound W-3

[0072]

[0073] According to the preparation method of Example 1, wherein R is 4-F.

[0074] 1 H NMR (400MHz, Acetone-d6) δ11.10(s,1H),7.81–7.60(m,2H),7.24–7.20(m,2H),6.99(t,J=1.9Hz,1H),5.93(s,1H),3.66(s,3H). 19 F NMR (376MHz, Acetone) δ-105.05,-138.44,-154.40,-163.46.

[0075] Example 5 Compound W-4

[0076]

[0077] According to the preparation method of Example 1, wherein R is 3-F or 4-F.

[0078] 1 H NMR(400MHz, Acetone-d6)δ11.13(s,1H),7.68(ddd,J=9.6,7.3,2.2Hz,1H),7.58–7.51(m,1H),7 .45(ddd,J=10.1,8.7,7.4Hz,1H),7.23(s,1H),6.99(t,J=1.9Hz,1H),6.03(s,1H),3.66(s,3H). 19 F NMR (376MHz, Acetone) δ-129.88,-136.22,-138.65,-154.19,-163.37.

[0079] Example 6 Compound W-5

[0080]

[0081] According to the preparation method of Example 1, wherein R is 3-F, 4-F, or 5-F.

[0082] 1 H NMR (400MHz, Acetone-d6) δ11.19(s,1H),7.56(t,J=6.4Hz,2H),7.24(t,J=2.3Hz,1H),6.98(t,J=1.9Hz,1H),6.10(s,1H),3.66(s,3H). 19 F NMR (376MHz, Acetone) δ-132.28,-137.86,-152.41,-153.94,-163.19.

[0083] Example 7 Compound W-6

[0084]

[0085] According to the preparation method of Example 1, wherein R is 4-Cl.

[0086] 1 H NMR (400MHz, Acetone-d6) δ11.25(s,1H),7.84–7.77(m,2H),7.69–7.60(m,2H),7.37(s,1H),7.14(t,J=2.0Hz,1H),6.10(s,1H),3.80(s,3H). 19F NMR (376MHz, Acetone) δ-138.61,-154.47,-163.67.

[0087] Example 8 Compound W-8

[0088]

[0089] According to the preparation method of Example 1, wherein R is 2-Cl, 4-Cl, or 5-Cl.

[0090] 1 H NMR (400MHz, Acetone-d6) δ11.30(s,1H),8.02(d,J=1.9Hz,2H),7.38(t,J=2.4Hz,1H),7.08(dd,J=2.7,1.5Hz,1H),6.50(s,1H),3.78(s,3H).

[0091] Example 9 Compound W-12

[0092]

[0093] According to the preparation method of Example 1, wherein R is 3-Cl or 4-Cl.

[0094] 1 H NMR (400MHz, Acetone-d6) δ11.13(s,1H),7.82(d,J=2.1Hz,1H),7.67(d,J=8.4Hz,1H),7.57( dd,J=8.4,2.1Hz,1H),7.23(d,J=2.8Hz,1H),7.00(t,J=2.0Hz,1H),6.07(s,1H),3.66(s,3H).

[0095] Example 10 Compound W-13

[0096]

[0097] According to the preparation method of Example 1, wherein R is 3-F.

[0098] 1 H NMR (400MHz, Acetone-d6) δ11.11(s,1H),7.56–7.37(m,4H),7.23(d,J=2.8Hz,1H),6.99(t,J=2.0Hz,1H),6.00(s,1H),3.66(s,3H).

[0099] Example 11 Compound W-14

[0100]

[0101] According to the preparation method of Example 1, wherein R is 2-Cl or 5-Cl.

[0102] 1 H NMR (400MHz, Acetone-d6) δ11.13(s,1H),7.76(dd,J=2.2,0.7Hz,1H),7.64–7.59(m,2H),7.24(s,1H),6.93(q,J=1.9Hz,1H),6.39(s,1H),3.64(s,3H).

[0103] Example 12 Compound W-17

[0104]

[0105] According to the preparation method of Example 1, wherein R is 2-Cl or 4-Cl.

[0106] 1 H NMR (400MHz, Acetone-d6) δ11.25(s,1H),7.95(d,J=8.5Hz,1H),7.85(d,J=2.0Hz,1H),7.59(dd, J=8.5,2.0Hz,1H),7.37(d,J=2.7Hz,1H),7.09(t,J=2.0Hz,1H),6.48(s,1H),3.81–3.76(m,6H). 19 F NMR (376MHz, Acetone) δ-137.94,-153.83,-163.38.

[0107] Example 13 Compound W-20

[0108]

[0109] According to the preparation method of Example 1, wherein R is 2-F or 4-F.

[0110] 1 H NMR (400MHz, Acetone-d6) δ11.11 (s, 1H), 7.73 (td, J = 8.5, 6.2Hz, 1H), 7.29–7. 21(m,2H),7.13–7.04(m,1H),6.97(q,J=1.8Hz,1H),6.07(s,1H),3.65(s,3H).

[0111] Example 14 Compound W-24

[0112]

[0113] According to the preparation method of Example 1, wherein R is 2-F or 3-Cl.

[0114] 1 H NMR (400MHz, Acetone-d6) δ11.12(s,1H),7.66(dd,J=8.5,7.6Hz,1H),7.47(dd,J=9.9,2.0Hz,1H),7.3 3(ddd,J=8.5,2.0,0.7Hz,1H),7.25(t,J=2.2Hz,1H),6.97(q,J=1.9Hz,1H),6.08(s,1H),3.65(s,3H). 19 F NMR (376MHz, Acetone) δ-106.37,-138.52,-153.90,-163.38.

[0115] Example 15 Compound W-25

[0116]

[0117] According to the preparation method of Example 1, wherein R is 4-CF3.

[0118] 1 H NMR (400MHz, Acetone-d6) δ11.28(s,1H),8.04(d,J=8.3Hz,2H),7.97(d,J=8.4Hz,2H),7.36(s,1H),7.13(s,1H),6.17(s,1H),3.79(s,3H). 19 F NMR (376MHz, Acetone) δ-63.77,-138.06,-154.18,-163.52.

[0119] Example 16 Compound W-26

[0120]

[0121] According to the preparation method of Example 1, wherein R is 4-ethyl.

[0122] 1H NMR (400MHz, Acetone-d6) δ11.26(s,1H),7.72–7.65(m,2H),7.47–7.41(m,2H),7.36(d,J=2.9Hz, 1H),7.11(q,J=1.8Hz,1H),6.00(s,1H),3.80(s,3H),2.75(q,J=7.6Hz,2H),1.23(t,J=7.6Hz,3H). 19 F NMR (376MHz, Acetone) δ-138.63,-154.82,-163.90.

[0123] Example 17 Compound W-27

[0124]

[0125] According to the preparation method of Example 1, wherein R is 4-cyclohexyl.

[0126] 1 H NMR (400MHz, Acetone-d6) δ11.08(s,1H),7.56–7.53(m,2H),7.33–7.28(m,2H),7.22(s,1H),6.96(s,1H),5.8 4(s,1H),3.66(s,3H),2.58–2.42(m,1H),1.64(dd,J=45.1,12.5Hz,4H),1.33–1.28(m,2H),0.90–0.71(m,4H). 19 F NMR(376MHz,Acetone)δ-138.91,-154.91,-164.02.

[0127] Example 18 Compound W-28

[0128]

[0129] According to the preparation method of Example 1, wherein R is 3-CF3 or 5-CF3.

[0130] 1 H NMR (400MHz, Acetone-d6) δ11.34(s,1H),8.68–8.14(m,3H),7.36(d,J=3.3Hz,1H),7.12(d,J=2.2Hz,1H),6.38(s,1H),3.81(d,J=1.3Hz,3H).

[0131] Example 19 Compound W-29

[0132]

[0133] According to the preparation method of Example 1, wherein R is 4-phenyl.

[0134] 1 H NMR(400MHz, Acetone-d6)δ11.27(s,1H),7.93–7.83(m,4H),7.78–7.69(m,2H), 7.57–7.42(m,3H),7.38(s,1H),7.14(d,J=2.2Hz,1H),6.08(s,1H),3.79(s,3H).

[0135] Example 20 Compound W-32

[0136]

[0137] According to the preparation method of Example 1, wherein R is 3-Cl or 5-Cl.

[0138] 1 H NMR (400MHz, Acetone-d6) δ11.33(s,1H),7.89(t,J=1.9Hz,1H),7.73(d,J=1.9Hz,2H),7.38(s,1H),7.12(d,J=2.2Hz,1H),6.27(s,1H),3.80(s,3H). 19 F NMR(376MHz,Acetone)δ-137.88,-154.07,-163.21.

[0139] Example 21 Compound W-37

[0140]

[0141] According to the preparation method of Example 1, wherein R is 2-F, 4-F, or 5-Cl.

[0142] 1 H NMR (400MHz, Acetone-d6) δ11.15(s,1H),7.77(dd,J=7.9,6.9Hz,1H),7.48(t,J =9.3Hz,1H),7.28(s,1H),6.98(dd,J=2.7,1.4Hz,1H),6.12(s,1H),3.65(s,3H). 19 F NMR (376MHz, Acetone) δ-101.10,-105.22,-138.36,-153.72,-163.20.

[0143] Example 22 Compound W-38

[0144]

[0145] According to the preparation method of Example 1, wherein R is 4-tert-butyl.

[0146] 1 H NMR (400MHz, Acetone-d6) δ11.24(s,1H),7.75–7.68(m,2H),7.64(d,J=8.6Hz,2H), 7.37(d,J=2.6Hz,1H),7.11(d,J=2.3Hz,1H),5.99(s,1H),3.80(s,3H),1.35(s,9H). 19 FNMR(376MHz,Acetone)δ-138.30,-154.89,-163.86.

[0147] Example 23 Compound W-42

[0148]

[0149] According to the preparation method of Example 1, wherein R is 4-CH2Br.

[0150] 1 H NMR(400MHz, Acetone-d6)δ11.05(s,1H),7.38(dd,J=8.6Hz,2H),7.33(dd,2H),7.10–7 .06(m,1H),6.81(ddd,J=2.6,1.8,0.8Hz,1H),5.42(s,1H),3.93(dd,2H),3.77(s,3H). 19 F NMR (376MHz, Acetone) δ-141.62,-158.93,-164.51.

[0151] The technical solution of the present invention is further illustrated by experiments below.

[0152] Experimental Example 1 Insecticidal Activity of Sulfone Compounds

[0153] 1. Experimental Methods

[0154] Insecticidal activity test method: 20 second-instar larvae of Spodoptera litura, Spodoptera frugiperda, and Spodoptera exigua were placed in 12-well culture plates. Culture medium soaked with 10 mg / L, 1 mg / L, 0.1 mg / L, and 0.01 mg / L working solutions of the target compound were added to the 12-well culture plates. Each concentration was tested in triplicate. After 48 hours, the mortality of the larvae was checked and the LC was calculated.50 ; Flurellanine was selected as the positive control.

[0155] 2. Experimental Results

[0156] As shown in Tables 1 and 2, the LC values of compounds W-27 and W-29 50 The values are low and the insecticidal activity is strong. The two compounds have better insecticidal activity against Spodoptera litura than the commercial insecticide flurelana. The results show that the sulfone compounds prepared by the present invention have good insecticidal activity against Spodoptera litura, Spodoptera frugiperda and Spodoptera exigua, and can be used as insecticides.

[0157] Table 1 Activity of compounds W-1 to W-42 against Spodoptera litura

[0158]

[0159]

[0160] Table 2 Activity of compounds W-1 to W-42 against fall armyworm and beet armyworm

[0161]

[0162]

Claims

1. A compound represented by formula I, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof: in, R is selected from hydrogen, halogen, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 20 Aryl, wherein the substituent is selected from halogen; n is selected from 0, 1, 2, 3, 4, 5.

2. The compound according to claim 1, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof, characterized in that: R is selected from halogen, substituted or unsubstituted C1-C4 alkyl, cyclohexyl, substituted or unsubstituted C6 aryl, wherein the substituent is selected from halogen; n is selected from 1, 2, and 3.

3. The compound according to claim 1 or 2, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof, characterized in that: R is selected from cyclohexyl and phenyl; n is selected from 1.

4. The compound according to claim 1, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof, characterized in that: The compound shown in Formula I is one of the following structures:

5. A method for preparing the compound according to any one of claims 1 to 4, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystalline form thereof, characterized in that: The steps include: Step 1, reacting compound a with pentafluorobenzoyl chloride to obtain compound b; Step 2, subjecting compound b to a reduction reaction to obtain compound c; Step 3, reacting compound c with thiol to obtain compound d; Step 4, reacting compound d with compound e to obtain a compound represented by formula I; The selection of R and n is as described in any one of claims 1-4.

6. The preparation method according to claim 5, characterized in that: In step 1, the reaction solvent is selected from at least one of dichloromethane and chloroform; And / or, in step 1, the reaction is carried out under the action of a catalyst, and the catalyst is selected from aluminum chloride; And / or, in step 1, the reaction is carried out in an ice bath for 20-40 minutes, followed by reaction at 20-30° C. for 2-4 hours; And / or, in step 2, the solvent of the reaction is selected from at least one of tetrahydrofuran and methanol; And / or, in step 2, the reducing agent of the reduction reaction is selected from sodium borohydride; And / or, in step 2, the reaction time of the reduction reaction is 2-4 hours; And / or, in step 3, the solvent of the reaction is selected from chloroform; And / or, in step 3, the reaction is carried out under the action of a catalyst, the catalyst being selected from zinc chloride; And / or, in step 3, the reaction time is 2-4 days; And / or, in step 4, the solvent of the reaction is selected from dichloromethane; And / or, in step 4, the reaction is carried out under the action of a catalyst, and the catalyst is selected from aluminum chloride; And / or, in step 4, the reaction time is 2-10 min.

7. Use of the compound according to any one of claims 1 to 4, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystal form thereof in the preparation of an insecticide.

8. The use according to claim 7, characterized in that The insecticide can prevent and control pests of the family Noctuidae of the order Lepidoptera.

9. The use according to claim 8, characterized in that The pests of the family Noctuidae of the order Lepidoptera include at least one of the group consisting of Spodoptera litura, Spodoptera frugiperda, and Spodoptera exigua.

10. An insecticide, characterized in that: The invention relates to a preparation prepared by using the compound according to any one of claims 1 to 4, or a salt thereof, or a solvate thereof, or a stereoisomer thereof, or a geometric isomer thereof, or an isotope-labeled substance thereof, or a crystal form thereof as an active ingredient.

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