Diphenyl ether substituted pyrazole derivative and application thereof
By synthesizing pyrazole derivatives substituted with diphenyl ether, the environmental and health threats posed by existing pyrazole compounds have been resolved, achieving highly efficient control of pests and mites, especially low-dose insecticidal effects against a variety of pests.
Patent Information
- Application Number
- CN202311527761.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2023-07-06
- Filing Date
- 2023-11-16
- Publication Date
- 2025-01-07
AI Technical Summary
Existing pyrazole compounds pose risks to pollinating insects and aquatic organisms in insecticides, and also pose threats to the environment and human health. There is a need to develop new pesticide compounds that are highly efficient and environmentally friendly.
This invention provides pyrazole derivatives substituted with diphenyl ether and their applications, and achieves pest control effects by synthesizing low doses of compound I. The preparation method includes using bromine, iodine, trifluoromethanesulfonate, etc. as reaction reagents, and the synthetic route includes reacting at 30-120℃ for 1-24 hours.
It achieves highly efficient control of pests and mites, especially effective control of pests such as Lepidoptera and Coleoptera, and exhibits significant insecticidal activity at low doses.
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Abstract
Description
Technical Field
[0001] The present invention relates to the field of agricultural chemicals, and in particular to a biphenyl ether-substituted pyrazole derivative and application thereof. Background Art
[0002] Pyrazole compounds are widely used in the field of agricultural chemicals. Pyrazole compounds are easy to synthesize, have diverse molecular structures, good biological activity and selectivity, making them a hot spot for the creation of new pesticides. Among the new varieties of pesticides currently being developed, more and more pyrazole insecticides, acaricides, herbicides and fungicides have emerged, such as the insecticides Fipronil, Pyrafluprole, Nicofluprole, etc. It is currently known that the introduction of nicotinamide in the molecular design process of physiologically active substances can change the lipid solubility, stability, permeability and other properties of drug molecules, and can significantly improve the biological activity of physiologically active molecules.
[0003]
[0004] It should be pointed out that these compounds have high insecticidal activity. However, there are certain risks to pollinating insects and aquatic organisms, and they pose certain threats to environmental safety and human health. Therefore, in order to meet the growing requirements of growers, the environment, consumers and regulatory agencies, agricultural chemicals need to continue to innovate and develop new solutions for managing crop pests. The development of an efficient, environmentally friendly and safe green pesticide compound has great application value in the agricultural field. Summary of the invention
[0005] In order to overcome the existing shortcomings and deficiencies, the primary purpose of the present invention is to provide a diphenyl ether substituted pyrazole derivative, which can achieve better pest control effects at a lower dosage.
[0006] Another object of the present invention is to provide applications of the above-mentioned pyrazole derivatives.
[0007] In a first aspect, the present invention provides a compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or a pesticidally acceptable salt thereof as a pyrazole derivative,
[0008]
[0009] in,
[0010] R1 is hydrogen, C 1-6 Alkyl, -C(=O)-C 1-6 Alkyl, -C 1-6 Alkylene-C(=O)-C 1-6 Alkyl, -C(=O)-OC1-6 Alkyl, -C 1-6 Alkylene-C(=O)-OC 1-6 Alkyl, C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-8 Cycloalkyl, C 6-12 Aryl, Aryl-C 1-3 Alkyl or C 3-8 Cycloalkyl C 1-3 alkyl;
[0011] R2 and R4 are hydrogen, halogen, hydroxy, nitro, amino, cyano, C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 Halogenated alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl;
[0012] R3 is hydrogen, fluorine-substituted C1-C4 alkyl or fluorine-substituted C 1-4 Alkoxy;
[0013] Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkoxy, C1-C6 haloalkoxyC1-C6 alkyl, C1-C6 haloalkoxyC1-C6 alkoxy, C3-C6 cycloalkylC1-C3 alkoxy, C3-C6 cycloalkyloxy;
[0014] Q is C 3-6 Cycloalkyl or three-membered to six-membered heterocycloalkyl, wherein the C 3-6 1 to 3 hydrogen atoms in the cycloalkyl or three-membered to six-membered heterocycloalkyl are optionally replaced by halogen, hydroxy, nitro, amino, cyano, C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Haloalkyl, C 1-6 Alkoxy or C 1-6 Haloalkoxy substitution.
[0015] In one embodiment of the present invention,
[0016] R1 is hydrogen, C 1-3 Alkyl, -C(=O)-C 1-3 Alkyl, -C 1-3 Alkylene-C(=O)-C 1-3 Alkyl, -C(=O)-OC 1-3 Alkyl, -C 1-3 Alkylene-C(=O)-OC 1-3 Alkyl, C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-8 Cycloalkyl;
[0017] R2 and R4 are hydrogen, halogen, hydroxy, nitro, amino, cyano, C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 1-3 Alkoxy, halogenated C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl;
[0018] R3 is a C1-C4 alkyl substituted with hydrogen or fluorine;
[0019] Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy;
[0020] Q is a cyclopropyl group, wherein 1 to 3 hydrogen atoms in the cyclopropyl group are optionally replaced by halogen, cyano, C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy or C 1-3 haloalkoxy substituted, preferably optionally substituted by fluorine, chlorine, bromine, cyano, methyl, monofluoromethyl, difluoromethyl, trifluoromethyl, ethyl, fluoroethyl, methoxy, monofluoromethoxy, difluoromethoxy, trifluoromethoxy or ethoxy;
[0021] In another embodiment of the present invention, wherein
[0022] R1 is hydrogen, C 1-3 Alkyl, C 3-8 Cycloalkyl;
[0023] R2 and R4 are hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 alkyl;
[0024] R3 is hydrogen or fluorine substituted C1-4 alkyl;
[0025] Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy;
[0026] Q is cyclopropyl.
[0027] In another preferred embodiment of the present invention, the compound of formula (I) has the following structure:
[0028]
[0029]
[0030] For the sake of simplicity, the "pyrazole derivatives", "compounds of formula (I)" or "compounds of the present invention" mentioned below may also include any isotope-labeled compounds of the compound of formula (I), or their optical isomers, geometric isomers, tautomers or isomer mixtures, or their pesticide-acceptable salts.
[0031] The compounds of the present invention can be prepared in a variety of ways known to those skilled in the art of organic synthesis. Those skilled in the art can refer to the synthetic routes of the specific compounds of the specific embodiments of the present invention and make appropriate adjustments to the reaction raw materials and reaction conditions to obtain synthetic methods for other compounds.
[0032] The compound of formula (I) of the present invention can be prepared by the following method:
[0033]
[0034] wherein Y is selected from bromine, iodine, triflate, boric acid, boric ester or trifluoroborate, and U is selected from boric acid, boric ester, trifluoroborate, bromine, iodine or triflate.
[0035] In particular, when Y is boronic acid, boronic ester or trifluoroborate, U is, for example, bromine, iodine or trifluoromethanesulfonate, and when Y is bromine, iodine or trifluoromethanesulfonate, U is, for example, boronic acid, boronic ester or trifluoroborate.
[0036] The specific steps include: dissolving raw material III in a suitable solvent, adding raw material II, and adding a base and a metal catalyst, reacting at a temperature of 30-120° C. for 1-24 hours to obtain the target compound I.
[0037] In addition, the present invention also lists a number of exemplary compounds that have been synthesized, and their specific group selections are shown in Table 1 below. It should be understood that the scope of the present invention is not limited to the exemplary compounds listed in the following table, and the various group selections of the compounds in Table 1 below can be arbitrarily combined without particular limitation.
[0038]
[0039] Table 1 Structures of some compounds
[0040]
[0041]
[0042] Table 2 Physical properties and characterization data of some compounds
[0043]
[0044]
[0045]
[0046]
[0047] In a second aspect, the present invention provides a pesticide composition comprising a compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or a pesticide-acceptable salt thereof, and a pesticide-acceptable carrier.
[0048] The pesticide-acceptable carrier may be an organic or inorganic inert carrier material, for example, suitable carriers include water, gelatin, gum arabic, magnesium stearate, talc, vegetable oil, polyalkylene glycol, vaseline, mannitol, cellulose, cellulose derivatives, sodium saccharin, magnesium carbonate, saline, glycerol, ethanol, etc. In addition, the pesticide composition may also contain other additives, such as preservatives, stabilizers, emulsifiers, buffers, diluents, adhesives, wetting agents, lubricants, glidants, etc.
[0049] The dosage form of the insecticide composition of the present invention can be a liquid dosage form, a solid dosage form or a semisolid dosage form, without particular limitation. In some embodiments, the dosage form of the insecticide composition is selected from powders, granules, liquids, suspensions or sprays, preferably wettable powders, wettable liquids, soluble powders, dispersible liquids, aqueous agents, microemulsions, emulsifiable concentrates, aqueous emulsions, sprayable solutions, dispersible oil suspensions, microcapsule suspensions, water-dispersible granules, water-soluble granules, large granules, granules for broadcasting and soil application, aerosols, ultra-low volume agents and wax products.
[0050] The content of the compound of the present invention in the insecticide composition can be adjusted according to actual needs (such as dosage form, application method, application object, etc.), including but not limited to 0.001 mg / L-10 mg / L, such as 0.001 mg / L, 0.01 mg / L, 0.1 mg / L, 0.5 mg / L, 1 mg / L, 2.5 mg / L, 5 mg / L or 10 mg / L.
[0051] The specific administration frequency can be determined by technicians in the relevant field, for example, once a day, once every two days, once every three days, once every four days, once every five days, once every six days, twice a day, three times a day, etc.
[0052] The compounds of the present invention are suitable for controlling pests or acarids, i.e. controlling pests or acarids, wherein the pests or acarids refer to harmful or unwanted insects or acarids, especially harmful or unwanted insects or acarids encountered in agriculture, forestry, storage product protection and material protection and hygiene. The compounds of the present invention are active against generally sensitive and resistant species and are effective at all stages of the development of the pests or acarids.
[0053] The present invention also relates to a method for controlling pests or mites, which comprises applying a control effective amount of a compound of formula (I) to the insect locus, insect habitat, pest habitat, area to be protected, or directly to the insect to be controlled. The compounds of the present invention can also be used to control other invertebrate pests or organisms.
[0054] The inventors of the present invention have found that even if the compound of the present invention is applied at a lower dose, it can still show a highly effective control effect on pests, especially on pests of the orders Lepidoptera, Coleoptera, Homoptera, Hemiptera, Thysanoptera, Isoptera, Diptera, Hymenoptera, Trichophaga, Pediculus, Orthoptera, Blattodea, Siphonaptera, Acarina, Nematoda, etc. In addition, in one embodiment of the present invention, the pests are selected from pests belonging to the phylum Arthropoda, Coleoptera, Diptera, Heteroptera, Homoptera, Hymenoptera, Isoptera, Lepidoptera, Orthoptera, Pediculus, Thysanoptera, and Nematoda.
[0055] In another preferred embodiment of the present invention, the pests may be selected from Plutella xylostella, armyworm, and Spodoptera litura.
[0056] Those skilled in the art will appreciate that the definitions and preferences described in one aspect of the present invention are equally applicable to other aspects. Those skilled in the art will appreciate that the embodiments of the various aspects of the present invention can be combined in various ways without departing from the subject matter and ideas of the present invention, and these combinations are also included within the scope of the present invention. DETAILED DESCRIPTION
[0057] The compounds of formula (I) of the present invention can be synthesized by various methods familiar to those skilled in the art of organic synthesis. The following specific examples provide some exemplary methods for synthesizing compounds of formula (I), which are well known in the field of synthetic chemistry. Obviously, referring to the exemplary schemes in this patent, those skilled in the art can easily design other synthetic routes of compounds of formula (I) by appropriately adjusting the reactants, reaction conditions and protecting groups.
[0058] The present invention is further described below with reference to the examples; however, these examples do not limit the scope of the present invention. Unless otherwise stated, all reactants used in the examples are obtained from commercial sources; the instruments and equipment used in the synthesis experiments and product analysis and detection are conventional instruments and equipment commonly used in organic synthesis.
[0059] Example 1: Synthesis of the compound N-methyl-N-cyclopropyl-2-chloro-5-[4-(4-chloro-phenyloxy)phenylpyrazol-4-yl]nicotinamide
[0060]
[0061] Under nitrogen protection, 5-bromo-2-chloro-N-cyclopropyl-N-methylnicotinamide (0.79 g, 2.6 mmol) was added to a 10 mL reaction bottle in sequence, 4-iodo-(4-chloro-phenyloxy)phenylpyrazole (1.46 g, 2.6 mmol), 15 mL of potassium carbonate (0.752 g, 5.2 mmol) aqueous solution and tetrakis(triphenylphosphine)palladium (0.16 g, 0.13 mmol) were added to the reaction bottle, and nitrogen was continued to be ventilated for 3 times. The reaction was carried out at 65 ° C for 5 h. After the reaction was completed as monitored by TLC, the filtrate was distilled under reduced pressure, extracted, and the organic phases were combined, washed with water, dried, filtered, concentrated under reduced pressure, and purified by column chromatography to obtain 0.933 mg of the product as a light yellow solid I-1 with a yield of 75%.
[0062] Other compounds in Table 1 can be prepared by methods similar to those exemplified above.
[0063] Example 2: Bioassay Example
[0064] This example tests the insecticidal activity of some pyrazole compounds against Plutella xylostella, Spodoptera litura, and Armyworm.
[0065] The specific implementation process is as follows:
[0066] Diamondback moth: At room temperature, use the Airbrush spray method to take cabbage leaves and make leaf discs with a diameter of 3 cm. Use acetone to remove the wax layer on the surface, spray the leaf discs evenly, put them in a petri dish lined with filter paper to dry in the shade, and inoculate 10 test insects. Set up a clean water treatment as a blank control. Conduct an experimental investigation 3 days later and record the number of dead and live test insects. Set up 3 replicates and take the average value of the results. The mortality rate is calculated according to formula (1). Use emamectin benzoate as a positive control. The specific results are shown in Table 3. The test concentrations are 200 mg / L, 100 mg / L, and 25 mg / L, respectively.
[0067]
[0068]
[0069] Sticky insects: At room temperature, use the Airbrush spray method to cut the middle leaves of corn into 2×5cm small sections, spray evenly on both sides of the leaves, and after the leaves are naturally dried in the shade, inoculate 10 3rd-instar sticky insect larvae. At the same time, set the water treatment as a blank control. Conduct an experimental investigation 72 hours after treatment, and record the number of dead and live insects in the test insects. Set up 3 replicates and take the average value of the results. The mortality rate is calculated according to formula (1). Emamectin benzoate is used as a positive control. The specific results are shown in Table 4. The test concentrations are 200mg / L, 100mg / L, and 50mg / L, respectively.
[0070] Spodoptera litura: At room temperature, use the leaf dipping method to make a 3cm diameter leaf disc from cabbage leaves. After dipping the leaf disc in the test solution for 10s, take it out and dry it at room temperature, then put it into a culture dish, 1 disc per dish, and move 10 test larvae that have been starved for 2h into it, and put it into a constant temperature incubator for culture. At the same time, set clear water treatment as a blank control. Conduct an experimental investigation 72h after treatment, and record the number of dead and live insects of the test insects. Set up 3 repetitions and take the average value of the results. The mortality rate is calculated according to formula (1), with emamectin benzoate as the positive control. The specific results are shown in Table 5. The test concentrations are 500mg / L, 200mg / L, and 100mg / L, respectively.
[0071] Table 3 The lethality of the compounds of the present invention to Plutella xylostella at different dosages
[0072]
[0073]
[0074] Table 4 The lethality of the compounds of the present invention to Mythimna separata at different dosages
[0075]
[0076] Table 5 The lethality of the compounds of the present invention to Spodoptera litura at different dosages
[0077]
[0078] From the data in the above table, it can be seen that compounds I-2, I-4, I-5, I-8, I-19 to I-21 all have certain insecticidal activity against diamondback moth, but the insecticidal activity is greatly affected by the substituents. In particular, compound I-19 has an insecticidal activity of 87% against diamondback moth at 25ppm. In general, the insecticidal activity test data in the above table show that the pyrazole compounds of the present invention have certain insecticidal activity against diamondback moth, Spodoptera litura, and armyworm, and are expected to develop into a new type of insecticide or drug precursor.
[0079] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be equivalent replacement methods and are included in the protection scope of the present invention.
[0080] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.
Claims
1. A compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or a pesticide-acceptable salt thereof, which is a biphenyl ether-substituted pyrazole derivative. in, R1 is hydrogen, C 1-6 Alkyl, -C(=O)-C 1-6 Alkyl, -C 1-6 Alkylene-C(=O)-C 1-6 Alkyl, -C(=O)-OC 1-6 Alkyl, -C 1-6 Alkylene-C(=O)-OC 1-6 Alkyl, C 1-6 Alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl, C 3-8 Cycloalkyl, C 6-12 Aryl, Aryl-C 1-3 Alkyl or C 3-8 Cycloalkyl C 1-3 alkyl; R2 and R4 are hydrogen, halogen, hydroxy, nitro, amino, cyano, C 1-6 Alkyl, C 1-6 Haloalkyl, C 1-6 Alkoxy, C 1-6 Halogenated alkoxy, C 2-6 Alkenyl, C 2-6 Alkynyl; R3 is hydrogen, fluorine-substituted C1-C4 alkyl or fluorine-substituted C 1-4 Alkoxy; Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 halocycloalkylC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkoxy, C1-C6 haloalkoxyC1-C6 alkyl, C1-C6 haloalkoxyC1-C6 alkoxy, C3-C6 cycloalkylC1-C3 alkoxy, C3-C6 cycloalkyloxy; Q is C 3-6 Cycloalkyl or three-membered to six-membered heterocycloalkyl, wherein the C 3-6 1 to 3 hydrogen atoms in the cycloalkyl or three-membered to six-membered heterocycloalkyl are optionally replaced by halogen, hydroxy, nitro, amino, cyano, C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, C 1-6 Haloalkyl, C 1-6 Alkoxy or C 1-6 Haloalkoxy substitution.
2. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its pesticide-acceptable salt, wherein: R1 is hydrogen, C 1-3 Alkyl, -C(=O)-C 1-3 Alkyl, -C 1-3 Alkylene-C(=O)-C 1-3 Alkyl, -C(=O)-OC 1-3 Alkyl, -C 1-3 Alkylene-C(=O)-OC 1-3 Alkyl, C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl, C 3-8 Cycloalkyl; R2 and R4 are hydrogen, halogen, hydroxy, nitro, amino, cyano, C 1-3 Alkyl, halogenated C 1-3 Alkyl, C 1-3 Alkoxy, halogenated C 1-3 Alkoxy, C 2-4 Alkenyl, C 2-4 Alkynyl; R3 is a C1-C4 alkyl substituted with hydrogen or fluorine; Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy; Q is a cyclopropyl group, wherein 1 to 3 hydrogen atoms in the cyclopropyl group are optionally replaced by halogen, cyano, C 1-3 Alkyl, C 1-3 Haloalkyl, C 1-3 Alkoxy or C 1-3 The haloalkoxy group is substituted, preferably optionally substituted, by fluorine, chlorine, bromine, cyano, methyl, monofluoromethyl, difluoromethyl, trifluoromethyl, ethyl, fluoroethyl, methoxy, monofluoromethoxy, difluoromethoxy, trifluoromethoxy or ethoxy.
3. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its pesticide-acceptable salt, wherein: R1 is hydrogen, C 1-3 Alkyl, C 3-8 Cycloalkyl; R2 and R4 are hydrogen, halogen, C 1-3 Alkyl, halogenated C 1-3 alkyl; R3 is hydrogen or fluorine substituted C 1-4 alkyl; Ar1 is a substituted or unsubstituted aryl group, which may be substituted by one or more substituents selected from halogen, cyano, nitro, C1-C3 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy; Q is cyclopropyl.
4. The compound of formula (I) according to claim 1 or its isotope-labeled compound, or its optical isomer, geometric isomer, tautomer or isomer mixture, or its pesticide-acceptable salt, which has the following structure:
5. An insecticide composition comprising a compound of formula (I) according to any one of claims 1 to 5 or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or a pesticidally acceptable salt thereof, and a pesticidally acceptable carrier.
6. The insecticide composition according to claim 5, wherein the dosage form is selected from powders, granules, liquids, suspensions or sprays, preferably wettable powders, wettable liquids, soluble powders, dispersible liquids, aqueous solutions, microemulsions, emulsifiable concentrates, aqueous emulsions, sprayable solutions, dispersible oil suspensions, microcapsule suspensions, water-dispersible granules, water-soluble granules, large granules, granules for broadcasting and soil application, aerosols, ultra-low volume agents and wax products.
7. Use of a compound of formula (I) or an isotope-labeled compound thereof, or an optical isomer, geometric isomer, tautomer or isomer mixture thereof, or an acceptable salt thereof in pesticides for the preparation of an insecticide for pest control according to any one of claims 1 to 4.
8. The use according to claim 7, wherein the pests are selected from the group consisting of pests belonging to the phylum Arthropoda, the order Coleoptera, the order Diptera, the order Heteroptera, the order Homoptera, the order Hymenoptera, the order Isoptera, the order Lepidoptera, the order Orthoptera, the order Phylum Acropora, the order Thysanoptera, and the phylum Nematoda.
9. The use according to claim 8, wherein the pests are selected from the group consisting of Plutella xylostella, armyworm, and Spodoptera litura.