Sulfonamide compound as well as preparation method and application thereof

Abstract

The invention provides a sulfonamide compound as well as a preparation method and application thereof. The structure of the sulfonamide compound is as shown in formula I:-I. The sulfonamide compound has excellent pest lethal activity. The invention further provides a preparation method of the sulfonamide compound, and the preparation method is simple and easy to produce. The invention also provides application of the sulfonamide compound in preparation of insecticides or acaricides, and the sulfonamide compound has good commercial development value.

Description

Technical Field

[0001] This application relates to the field of pesticide technology, specifically to a sulfonamide compound, its preparation method, and its application. Background Technology

[0002] Current agricultural pest control methods still primarily rely on pesticides. The widespread use of traditional pesticides has led to problems such as the development of pesticide resistance in pests and environmental pollution risks. Many pests have developed severe resistance to some classic pesticides due to long-term use, resulting in poor pesticide efficacy. Furthermore, with increasing environmental requirements, the development of green pesticides will be a new trend in future plant protection development.

[0003] Therefore, it is necessary to provide a more efficient insecticide. Summary of the Invention

[0004] To discover and develop more efficient, broad-spectrum, low-toxicity pesticide lead and candidate compounds without cross-resistance, this invention innovatively designs and synthesizes a sulfonamide compound (as shown in Formula I). ​​According to national standards for insecticide bioassays, the inventors conducted insecticidal activity tests on a series of compounds. The relevant bioassay data show that the synthesized compound exhibits good insecticidal activity at low concentrations, low toxicity to non-target organisms, safety for mammals, and no negative environmental effects, meeting the requirements for the development of environmentally friendly green pesticides and possessing high value. This application has strong academic, social, and economic value for the development of sulfonamide compounds with novel structures and good environmental compatibility.

[0005] To address at least one of the aforementioned technical problems, in a first aspect, this application provides a sulfonamide compound or a pesticide-acceptable salt thereof, the structure of which is shown in Formula I:

[0006] I; Where R is selected from , -(CH2) n3 -C3-C8 cycloalkyl, -(CH2) n4 -C3-C8 heterocycle or -(CH2) n5 - Substituted C3-C8 heterocycles, R1, R2, R3, R4 are independently selected from cyano, C1-C6 alkyl, halogen, and halogen-substituted C1-C6 alkyl, respectively; n1, n2, n3, n4, n5 are independently selected from integers from 0 to 5; Het is selected from... , , , , , , Ar is selected from R5 is selected from cyano, C1-C6 alkyl, halogen-substituted C1-C6 alkyl, and n6 is selected from integers from 0 to 5; R6 is selected from hydrogen and C1-C6 alkyl; R7 is selected from C1-C6 alkyl and halogen-substituted C1-C6 alkyl.

[0007] Preferably, R1 and R4 are independently selected from cyano, C1-C3 alkyl, and halogen-substituted C1-C3 alkyl groups, respectively; R2 and R3 are independently selected from C1-C3 alkyl groups, respectively; R6 is selected from hydrogen and C1-C3 alkyl groups; R7 is selected from fluorine-substituted C1-C3 alkyl groups; and C3-C8 cycloalkyl groups are selected from... , , The substituted C3-C8 heterocycle is selected from C1-C3 alkyl-substituted C3-C8 heterocycles, amino-substituted C3-C8 heterocycles, and -N(CH3)2-substituted C3-C8 heterocycles.

[0008] Preferably, the structure of the sulfonamide compound is shown in Formula I-1: ; Preferably, Het is selected from , , .

[0009] Preferably, Ar is selected from , R 51 R 52 R 53 R 54 R 55 They are independently selected from halogens and halogen-substituted C1-C3 alkyl groups.

[0010] Preferably, Ar is selected from , , .

[0011] Preferably, n1 and n2 are each independently selected from integers between 0 and 3.

[0012] Preferably, R is selected from , R1 and R4 are independently selected from cyano, -CHF2, and -CF3, respectively.

[0013] Preferably, R2 and R3 are both methyl groups.

[0014] Preferably, the sulfonamide compound is selected from the following structures: , 、 、

[0015] 、 、 、

[0016] 、 、 、

[0017] 、 、 、

[0018] 、 、 、

[0019] 、 、 、

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[0028] 、 、 、

[0029] 、 、 、

[0030] 、 、 、

[0031] 、 、 、

[0032] 、 、 、

[0033] 、 、 、

[0034] 、 、 、

[0035] 、 、 、

[0036] 、 、 、

[0037] 、 、 、

[0038] 、 、 、

[0039] 、 、 、

[0040] 、 、 、

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[0042] 、 、 、

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[0044] , , ,

[0045] , , ,

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[0049] , , ,

[0050] , , ,

[0051] , , ,

[0052] , , ,

[0053] , , ,

[0054] , , .

[0055] Preferably, the sulfonamide compound is selected from the following structures: , , ,

[0056] , , ,

[0057] , , ,

[0058] , , ,

[0059] , , ,

[0060] .

[0061] Preferably, the pesticide-acceptable salt of the sulfonamide compound is prepared by reacting the sulfonamide compound with a pesticide-acceptable acid, wherein the pesticide-acceptable acid is an inorganic acid or an organic acid, wherein the inorganic acid is selected from at least one of hydrochloric acid, sulfuric acid, phosphoric acid and hydrobromic acid, and the organic acid is selected from at least one of oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, citric acid and benzoic acid.

[0062] Secondly, this application provides a method for preparing the sulfonamide compound or its pesticide-acceptable salt as described in the first aspect of this application, wherein the reaction formula for preparing the sulfonamide compound is as follows: ;

[0063] Where X is a halogen.

[0064] Preferably, the reaction formula for preparing the sulfonamide compound is as follows: ;

[0065] Where X is Cl.

[0066] Preferably, the preparation of the sulfonamide compound includes: reacting compound A and compound B under the action of an acid-binding agent to obtain a reaction solution containing the sulfonamide compound, purifying the solution to obtain the sulfonamide compound.

[0067] Preferably, the acid-binding agent is K2CO3, triethylamine, or pyridine.

[0068] Preferably, the solvent used in the reaction is dichloromethane.

[0069] Preferably, the purification includes extraction and recrystallization, and the solvent used for recrystallization is dichloromethane.

[0070] Thirdly, this application provides an agricultural insecticide and acaricide composition, characterized in that it includes the sulfonamide compounds described in the first aspect of this application or their pesticide-acceptable salts.

[0071] Preferably, the pesticide further includes commercial agricultural insecticides, including acetamiprid, difenoconazole, acetamiprid, abamectin, imidacloprid, spinosad, heptamethrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, deltamethrin, cypermethrin, β-cyhalothrin, lambda-cyhalothrin, dichlorvos, permethrin, allethrin, bifenthrin, permethrin, permethrin, flufenoxuron, flufenoxuron, imidacloprid, acetamiprid, chlorpyrifos, thiamethoxam, thiamethoxam, dinotefuran, difenoconazole, diflubenzuron, difenoconazole ... The following are listed as examples of polyfluorourea, flufenoxuron, diphenylfluorourea, flufenoxuron, fenflurfen, fenflurfen, furazolidone, chlorfenapyr, methoxyfenozide, cyclone dichlorvos, dichlorvos, quinalphos, pyridazin, leafhopper powder, carbaryl, pirimicarb, fenpropathrin, isoprocarb, fenitrothion, sec-butanil, leaf spray, carbaryl, fenitrothion, bromopropylate, thiamethoxam, azoxystrobin, pyridaben, tetradifon, propargite, difenoconazole, pymetrozine, spirodiclofen, spirotetramat, triazophos, thiamethoxam, chlorfenapyr, tetrachlorfenapyr, flufenoxuron, flufenoxuron, cyantraniliprole, butenylflufenoxam, azoxystrobin, bromopropylate, pyrazinone, etoxazole, pyridaben, pyridaben, pyriproxyfen, emamectin, pendimethalin.

[0072] Preferably, the sulfonamide compound or its pesticide-acceptable salt in the agricultural insecticide and acaricide composition has a mass percentage of 0.1%-99.9%.

[0073] Preferably, the agricultural insecticide and acaricide composition further includes adjuvants, wherein the adjuvants in the agricultural insecticide and acaricide composition have a mass percentage of 0.1%-99.9%.

[0074] Preferably, the additives include at least one of solvents, surfactants, emulsifiers, and pH adjusters.

[0075] Preferably, the additives include acetone and an emulsifier in a volume ratio of 1:(8-10).

[0076] Preferably, the emulsifier comprises 0.5-3% by mass of APG0810, 8-12% by mass of 505 emulsifier, 3-5% by mass of 700# emulsifier, 8-12% by mass of xylene, 3-8% by mass of 604# emulsifier, and 200# solvent oil.

[0077] Preferably, the concentration of the sulfonamide compound or its pesticide-acceptable salt in the pesticide is 10-10. 5 mg / L.

[0078] Preferably, the formulation of the agricultural insecticide and acaricide composition is selected from: water emulsion, microemulsion, suspension emulsion, capsule suspension, water-soluble granules, fine granules, soluble concentrate, poison grains, block poison bait, granular poison bait, flake poison bait, concentrated poison bait, slow-release blocks, electrostatic sprays, oil-in-water emulsions, smoke cans, smoke candles, smoke tubes, smoke sticks, smoke sheets, smoke pellets, ointments, thermal fogging agents, solid / liquid mixtures, liquid / liquid mixtures, solid / solid mixtures, medicated paints, microparticles, tracking powders, oil suspensions, oil-dispersible powders, concentrated gels, pouring agents, seed coating agents, smearing agents, film-forming oils, ultra-low volume liquids, and vapor release agents.

[0079] Fourthly, this application provides the use of the sulfonamide compound described in the first aspect of this application or its phytochemically acceptable salt, or the agricultural insecticide and acaricide composition described in the third aspect of this application, in the preparation of insecticides and / or acaricides.

[0080] Preferably, the sulfonamide compounds or their phytochemically acceptable salts or the pesticides described above can be used to kill pests or mites on fruit trees, vegetables and ornamental plants. The sulfonamide compounds or their phytochemically acceptable salts or the pesticides described above can also be used to kill pests, mites or ticks in the growing environment of fruit trees, vegetables and ornamental plants, such as soil and nutrient solution.

[0081] Preferably, the insects include diamondback moth, cutworm, yellow cutworm, kapok worm, bean looper, forked looper, tree looper, spruce leafroller, rice stem borer, apple leafroller, pine caterpillar, southwestern corn stalk borer, Egyptian borer, South American corn seedling borer, privet leafroller, wax borer, plum fruit moth, pear fruit moth, cotton bollworm, tobacco bud borer, corn ear borer, cabbage borer, fall webworm, apple leafminer, tomato moth, beet armyworm, coffee leafminer, spiral leafminer, grape berry leafroller, beet webworm, gypsy moth, tussock moth, peach leafminer, yellow tent caterpillar, cabbage looper, fir tussock moth, corn borer, small-eyed looper, cotton pink bollworm, Xinjiang looper, round-handled boat moth, potato leafminer, citrus Leaf miner, European white butterfly, alfalfa green armyworm, diamondback moth, soybean armyworm, wheat moth, grape leafroller, grassland armyworm, sea gray-winged armyworm, beet armyworm, green oak moth, pink-striped armyworm, pear narrow jewel beetle, straight click beetle, dark click beetle, Mexican cotton boll weevil, apple flower weevil, beet gnat beetle, pit pruning beetle, broad bean weevil, pea weevil, European lentil weevil, apple leaf roller, beet beet giant beetle, golden flower beetle, cabbage seed beetle, bladder beetle, beet shank flea beetle, asparagus leaf beetle, longhorn leaf beetle, South American leaf beetle, corn root leaf beetle, Mexican bean ladybug, tobacco flea beetle, cotton gray weevil variant, European pine bark weevil, Egyptian alfalfa leaf weevil, purple alfalfa leaf weevil, spruce eight-toothed bark beetle, tobacco leaf beetle, black-horned leaf beetle Potato leaf beetle, rice water weevil, rapeseed leaf beetle, large chestnut gill beetle, May gill beetle, rice mud beetle, grape black-eared beetle, strawberry root weevil, horseradish leaf beetle, leaf-eating gill beetle, garden flea beetle, soybean pale-legged flea beetle, yellow-striped flea beetle, Japanese scarab beetle, pea leaf weevil, grain weevil; flies and mosquitoes such as Aedes aegypti, Aedes albopictus, Aedes nigra, Mexican fruit fly, Anopheles five-spotted mosquito, Anopheles white-legged mosquito, Anopheles malaria, Anopheles white-ankle, Anopheles minimus, Anopheles four-spotted mosquito, blowfly, Mediterranean fruit fly, maggot fly, deer fly, sorghum gall midge, Culex pipiens pulveratus, Aedes mosquito, Culex quinquefasciatus, Aedes mosquito, melon fly, olive fruit fly, rapeseed leaf gall midge, onion fly, wheat field seed fly, gray field seed fly, cabbage root fly Human skin fly, small toilet fly, horse fly, tsetse fly, spiky tsetse fly, peanut field gray seed fly, striped skin fly, vegetable leafminer, American leafminer, green leaf fly, silky green fly, wheat gall midge, autumn housefly, housefly, stable carrion fly, sheep mad fly, European wheat straw fly, turnip fly, cherry fruit fly, apple fruit fly, red-tailed flesh fly, flesh fly genus, stable stinging fly, horsefly red barnacle, and European giant mosquito; thrips such as orchid thrips, smoke brown thrips, alfalfa flower thrips, oriental flower thrips, bellflower thrips, rice thrips, palm thrips, tobacco thrips; termites such as yellow-legged reticulate termite, southern reticulate termite, European reticulate termite, black-breasted reticulate termite, house termite ant; cockroaches such as German cockroach, American cockroach, Japanese cockroach, brown cockroach, Australian cockroach, and oriental cockroach;And bedbugs, aphids, leafhoppers, whiteflies, scale insects, cicadas such as *Pseudomorphus spp.*, *Pseudomorphus corniculatus*, *Pseudomorphus spp. ... Aphids, corn aphids, cereal overflow aphids, wheat two-pronged aphids, wheat long-tubed aphids, whiteflies, grape root phylloxera; ants, bees, wasps, sawflies such as Xinjiang cabbage leaf wasps, leafcutter ants, *Hemiberlesia spp.*, black hairy ants, small yellow house ants, tropical fire ants, red fire ants, black fire ants, southern fire ants, red ants, big-headed ants, velvet ants, bumblebees, hornets, yellow-edged hornets, wasps, Argentine ants; crickets, grasshoppers, locusts, house crickets, mole crickets, migratory locusts, two-striped black locusts, red-legged black locusts, Mexican black locusts, migratory black locusts, rock-dwelling black locusts, striped red locusts, American desert locusts, African desert locusts, Moroccan horn-striped locusts, garden crickets, Senegalese small car locusts, stink gland locusts, Italian locusts, Australian locusts, brown migratory locusts.

[0082] Preferably, the nematode also includes control nematodes (e.g., plant parasitic nematodes such as root-knot nematodes, northern root-knot nematodes, southern root-knot nematodes, Javan root-knot nematodes), *Root-knot Nematodes*, cyst-forming nematodes, potato golden nematode, *Sacchariformis*, cereal cyst nematode, soybean cyst nematode, beet cyst nematode, clover cyst nematode, seed gall nematode, *Gracilaria*, stem and leaf nematodes, *Smilax*, stinging nematode, weed stinging nematode and other needle-stinging nematodes, pine nematode, pine wood nematode, annular nematode, *Syngonium*, *Small annular nematode*, *Rotaria*, *Medium annular nematode*, and bulb nematode. Stem nematodes, sweet potato stem nematodes, trypanosomes, trypanosomes, spiral nematodes, sheath nematodes, sheath-shaped nematodes, sheath nematodes and hemirotifers, root-burrowing nematodes, crown nematodes, spear nematodes, pseudo-root-knot nematodes, pearl nematodes, needle nematodes, transverse needle nematodes and other long needle nematodes, root rot nematodes, piercing root rot nematodes, whole short-bodied nematodes, perforating nematodes, banana perforating nematodes, kidney-shaped nematodes, spiral nematodes, residual root nematodes, primitive hairy nematodes, pseudo-hairy nematodes, growth-blocking nematodes, purslane dwarfing nematodes, compliant and compliant dwarfing nematodes, citrus nematodes, hemi-piercing nematodes, xiphoid nematodes.

[0083] The ticks and mites mentioned include: ticks (Acari order), long star tick, tropical flower tick, Persian sharp-edged tick, cattle tick, tiny cattle tick, castor hard tick, chicken skin mites, human scabies mite, apple rust mite, fine mites, and leaf mites.

[0084] Preferably, the insect includes at least one of diamondback moth and thrips; the mite is a spider mite.

[0085] In summary, this application includes at least one of the following beneficial technical effects: 1. This application provides a sulfonamide compound or its pesticide-acceptable salt. Based on the principles of pesticide molecular design and optimization, this application innovates the skeletal structure and selects sulfonamide compounds with stable structures and properties. This breaks through the application limitations of traditional amide pesticides and greatly expands the control range of amide insecticides against agricultural pests. Some compounds have good control effects on a variety of agricultural pests. They have excellent lethal activity against Lepidoptera, Homoptera, and Thysanoptera pests and are not prone to cross-resistance with existing amide compounds.

[0086] 2. This application also provides a method for preparing the above-mentioned sulfonamide compounds, which is simple and easy to produce.

[0087] 3. This application provides an agricultural insecticide and acaricide composition comprising the above-mentioned sulfonamide compounds, wherein the agricultural insecticide and acaricide composition has excellent insecticidal activity.

[0088] 4. This invention also provides the application of the above-mentioned sulfonamide compounds in the preparation of insecticides or acaricides. These sulfonamide compounds can be used for pest control in the agricultural, horticultural, and forestry fields, and have great commercial development value. Detailed Implementation

[0089] The present invention will be further described below with reference to specific embodiments. However, the following embodiments are for illustrative purposes only and should not be considered as limiting the scope of the invention. Unless otherwise specified, specific conditions in the following embodiments are performed under conventional conditions or conditions recommended by the manufacturer. Unless otherwise specified, the methods used are conventional methods known in the art, and the consumables and reagents used are commercially available. Unless otherwise stated, the technical and scientific terms used herein have the same meaning as those familiar with the art. Furthermore, any methods or materials similar to or equivalent to those described herein may also be applied to the present invention.

[0090] Example 1 Example 1 provides a sulfonamide compound with the structure shown in Formula I-1:

[0091] I-1; Where R is selected from , -(CH2) n3 -C3-C8 cycloalkyl, -(CH2) n4 -C3-C8 heterocycle or -(CH2) n5- Substituted C3-C8 heterocycles, R1, R2, R3, R4 are independently selected from cyano, C1-C6 alkyl, halogen, and halogen-substituted C1-C6 alkyl, respectively; n1, n2, n3, n4, n5 are independently selected from integers from 0 to 5; Het is selected from... , , , , , , Ar is selected from R5 is selected from cyano, C1-C6 alkyl, halogen-substituted C1-C6 alkyl, and n6 is selected from integers from 0 to 5.

[0092] Preferably, R1 and R4 are independently selected from cyano, C1-C3 alkyl, and halogen-substituted C1-C3 alkyl groups, respectively; R2 and R3 are independently selected from C1-C3 alkyl groups, respectively; R6 is selected from hydrogen and C1-C3 alkyl groups; R7 is selected from fluorine-substituted C1-C3 alkyl groups; and C3-C8 cycloalkyl groups are selected from... , , The substituted C3-C8 heterocycle is selected from C1-C3 alkyl-substituted C3-C8 heterocycles, amino-substituted C3-C8 heterocycles, and -N(CH3)2-substituted C3-C8 heterocycles.

[0093] The structures and compound numbers of the sulfonamide compounds provided in the examples are shown in Table 1 below: Table 1. Structures of sulfonamide compounds

[0094] The reaction formula for preparing the sulfonamide compound is shown below: ;

[0095] Where X is Cl.

[0096] The preparation method of the sulfonamide compounds provided in this application is illustrated below using the preparation of compound 1 as an example.

[0097] The chemical structure of compound 1 (compound number 1) is as follows: ; The chemical reaction equation for the preparation of compound 1 is shown below: ; Specific experimental procedures: Add triethylamine (20 mmol) to a 100 mL reaction flask and (4.37 g, 10 mmol) Then add dichloroethane (50 mL), and add 20 mL containing [unclear text - possibly a substance or ingredient] dropwise at room temperature with stirring. A solution of 2.20 g (10 mmol) in dichloroethane was stirred for 2.5 h at 15–35 °C. After the reaction was complete, the solvent was removed, and then 60 mL of ethyl acetate and 10 mL of water were added sequentially. After thorough stirring, the ethyl acetate phase was separated. The ethyl acetate phase was dried over sodium sulfate, the solvent was removed, and recrystallization in dichloroethane yielded 5.62 g of a white powdery solid with a melting range of 189.4–192.5 °C and a yield of 90.6%.

[0098] The preparation methods for the other compounds in Table 1 are the same as for compound 1. The only difference lies in the different Ar, R, and Het groups in the reactants. The physicochemical properties of the resulting compounds 1, 2, 3, 57, 58, 59, 60, 99, 100, 101, 102, 113, 155, 156, 157, and 158 are as follows: 1 The H-NMR data are shown in Table 2 below.

[0099] Table 2 Physicochemical properties of sulfonamide compounds and 1 H-NMR data

[0100] Example 2 This application tested the mortality rates of the sulfonamide compounds prepared in this application against diamondback moth, spider mites, and thrips. These insect species are highly representative and can represent most pests occurring in the field during agricultural production. The insecticidal activity tests of the sulfonamide compounds provided in this application are as follows: 1. The mortality rate of diamondback moth was determined according to the Agricultural Industry Standard of the People's Republic of China, "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 14: Leaf Dipping Method" NY / T 1154.14-2008.

[0101] The procedure for determining the mortality rate of diamondback moth using the leaf immersion method is as follows: (1) Preparation of test materials: Select 3rd instar larvae of diamondback moth that have been continuously reared indoors and have the same physiological state as standard test insects, and starve them for 4 hours in advance. Select rapeseed leaves with the same growth and no pesticide residue to make leaf discs with a diameter of 1.5cm. When preparing leaf discs, try to avoid selecting parts with large and thick veins.

[0102] (2) Preparation of reagent: Weigh 0.1 g of the technical grade drug (sulfonamide compound and positive control prepared in this application), dissolve it in 1 mL of acetone, and then use emulsifiers (including 1% APG0810, 10% 505 emulsifier, 4% 700# emulsifier, 10% xylene, 5% 604# emulsifier, and then make up to 100% with 200# solvent oil) to make up to 10 mL in a volumetric flask. After complete dissolution, a concentration of 10 is obtained. 4 The mother liquor of mg / L was diluted 100 times with distilled water to obtain a drug solution of 100 mg / L for later use.

[0103] (3) Chemical treatment: Immerse the leaf discs in the chemical solution, remove them after 10 seconds, and let them air dry in a ventilated place. Transfer them to 9 cm diameter petri dishes with moistened filter paper for humidity control, and inoculate them with 3rd instarred diamondback moth larvae that have completed starvation. Place 10 larvae in each dish. The experiment includes a solvent control (using a solution without chemical treatment (1 mL of acetone diluted to 10 mL with the above emulsifier)) and a positive control using the compound Fluxametamide. Each group has 6 parallel experiments.

[0104] (4) Feeding and observation: The treated test insects were fed and observed under the conditions of temperature (25±1)℃, photoperiod L:D=16 h:8 h and relative humidity (65±5)%.

[0105] (5) Investigation: Check the mortality of test insects 24 h and 48 h after treatment. Touch the surface of the test insect with a brush. If the insect does not move within 5 seconds, it is considered dead. Record the total number of test insects and the number of dead insects in each group, calculate the mortality rate, and take the average value. The results are shown in Table 3.

[0106] 2. The mortality rate of spider mites was determined in accordance with the Agricultural Industry Standard of the People's Republic of China, "Guidelines for Indoor Bioassay Tests of Pesticides - Insecticides Part 12: Spider Mite Slide Immersion Method" NY / T 1154.12-2008.

[0107] The procedure for determining the mortality rate of spider mites using the slide immersion method is as follows: (1) Preparation of test materials: Select female adult mites that have been continuously reared indoors and are in the same physiological state as standard test insects. Cut double-sided tape into 2cm lengths and attach them to one end of a glass slide. Then, attach the backs of healthy female adult mites to the double-sided tape, taking care not to stick the mite legs, antennae, and mouthparts. Place 20 mites per slide in a petri dish lined with moist cotton, cover the slide, and place it under the conditions of temperature (25±1)℃, photoperiod L∶D=16 h∶8 h, and relative humidity (65±5)%. Examine the slide under a microscope after 2 hours, remove dead and injured individuals, and replenish the slide to 20 mites per slide.

[0108] (2) Preparation of reagent: Weigh 0.1 g of the technical grade drug (sulfonamide compound and positive control prepared in this application), dissolve it in 1 mL of acetone, and then use emulsifiers (including 1% APG0810, 10% 505 emulsifier, 4% 700# emulsifier, 10% xylene, 5% 604# emulsifier, and then make up to 100% with 200# solvent oil) to make up to 10 mL in a volumetric flask. After complete dissolution, a concentration of 10 is obtained. 4 The mother liquor of mg / L was diluted 100 times with distilled water to obtain a drug solution of 100 mg / L for later use.

[0109] (3) Treatment with pesticide: Immerse the slide with spider mites in the pesticide solution, gently shake for 5 seconds, remove it, absorb excess pesticide with absorbent paper, place it in a petri dish lined with moist cotton, cover the dish, and place it under the conditions of (25±1)℃, photoperiod L:D=16h:8h, and relative humidity (65±5)%. The experiment included a solvent control (using a solution without pesticide (1 mL of acetone diluted to 10 mL with the above emulsifier)) and a positive control of the compound Fluxametamide. Six parallel experiments were set up for each group.

[0110] (4) Feeding and observation: The treated spider mites were fed and observed under the conditions of temperature (25±1)℃, photoperiod L:D=16 h:8 h and relative humidity (65±5)%.

[0111] (5) Investigation: Check the mortality of spider mites 24 h and 48 h after treatment. Gently touch the legs or mouthparts of the mites with a brush. If there is no reaction, the mites are considered dead. Record the total number of tested mites and the number of dead mites in each group, calculate the mortality rate, and take the average value. The results are shown in Table 3.

[0112] 3. According to the People's Republic of China Agricultural Industry Standard NY / T 3680-2020: Technical Specification for Monitoring Herbicide Resistance of Western Flower Thrips - Determination of Thrips Mortality by Leaf Tube Film Method.

[0113] The procedure for determining thrips mortality using the leaf tube film method is as follows: (1) Preparation of test materials: Select adult western flower thrips that have been continuously reared indoors and are in the same physiological state as standard test insects. Select cowpea pods with uniform growth and no pesticide residues and make them into segments of about 2 cm, making sure that no beans are left at both ends of the pods. Cut off the bottom of a 10 ml centrifuge tube, then attach 200 mesh mesh, and tighten the cap for subsequent experiments.

[0114] (2) Preparation of reagent: Weigh 0.1 g of the technical grade drug (sulfonamide compound and positive control prepared in this application), dissolve it in 1 mL of acetone, and then use emulsifiers (including 1% APG0810, 10% 505 emulsifier, 4% 700# emulsifier, 10% xylene, 5% 604# emulsifier, and then make up to 100% with 200# solvent oil) to make up to 10 mL in a volumetric flask. After complete dissolution, a concentration of 10 is obtained. 4 The mother liquor of mg / L was diluted 100 times with distilled water to obtain a drug solution of 100 mg / L for later use.

[0115] (3) Drug treatment: Use a pipette to fill 10 mL centrifuge tubes with the drug solution through a mesh screen, let stand for 4 hours, then discard the drug solution and air dry. Each tube constitutes a replicate. Immerse the pre-cut cowpea segments in the drug solution, remove them after 10 seconds, and let them air dry naturally at room temperature. Use tweezers to pack the dried cowpea segments into centrifuge tubes treated with the corresponding concentration of drug solution, one segment per tube. Set up a solvent control (using a solution without the drug solution (1 mL of acetone diluted to 10 mL with the above emulsifier)) and a positive control drug, the compound Fluxametamide. Set up 5 parallel experiments for each group.

[0116] (4) Inoculation: Use a pipette to transfer thrips into centrifuge tubes, about 15 to 20 test thrips per tube, and then cover the tubes.

[0117] (5) Feeding and observation: The treated test insects were fed and observed under the conditions of temperature (25±1)℃, photoperiod L:D=16 h:8 h and relative humidity (65±5)%.

[0118] (6) Investigation: The mortality of test insects was checked 24 h and 48 h after treatment. The insects that could not crawl when touched with the tip of a brush were considered dead. The total number of test insects and the number of dead insects in each group were recorded. The mortality rate was calculated and the average value was taken. The results are shown in Table 3.

[0119] In the three groups of experiments, the mortality rate of diamondback moth, spider mite, and thrips in the solvent control group was close to 0, indicating that the solvent control group had no killing effect on diamondback moth, spider mite, and thrips.

[0120] The sulfonamide compounds 1, 2, 3, 57, 58, 59, 60, 99, 100, 101, 102, 113, 155, 156, 157, and 158, and the positive control compound Fluxametamide, exhibited their insecticidal effects against diamondback moth, spider mite, and thrips at a concentration of 100 mg / L for 48 hours in an indoor bioassay. The structure of the positive control compound Fluxametamide (CK) is as follows:

[0121] Fluxametamide Table 3. Insecticidal and acaricidal activity test results of sulfonamide compounds.

[0122] Table 3 shows that, according to the aforementioned national standards for pesticide bioassay, the insecticidal activity of the sulfonamide compounds prepared in this invention was determined. The experimental data indicate that the sulfonamide compounds with the unique structure designed in this invention exhibit insecticidal effects unexpected by those skilled in the art. The sulfonamide compounds prepared in this invention are photochemically stable and, in controlling agricultural pests, break through the limitations of traditional amide insecticides, greatly expanding the control range of agricultural pests by sulfonamide pesticides, with results far exceeding the expectations of those skilled in the art. The sulfonamide compounds provided by this invention all exhibit good insecticidal activity, yielding unexpected results. Among them, compounds 1, 57, 99, 101, and 155 show significantly better killing effects on thrips than the positive control compound Fluxametamide. Under the same test conditions, the sulfonamide compounds provided by this invention show remarkable specificity and ideal control effects on agricultural pests, making them suitable for further development and utilization as agricultural insecticides. This is unexpected and inconceivable to those skilled in the art without creative effort.

[0123] The above are all preferred embodiments of this application, and are not intended to limit the scope of protection of this application. Therefore, all equivalent changes made in accordance with the structure, shape and principle of this application should be covered within the scope of protection of this application.

Claims

1. A sulfonamide compound or a pesticide-acceptable salt thereof, characterized in that, The structure of the sulfonamide compound is shown in Formula I: I； Where R is selected from , -(CH2) n3 -C3-C8 cycloalkyl, -(CH2) n4 -C3-C8 heterocycle or -(CH2) n5 - Substituted C3-C8 heterocycles, R1, R2, R3, R4 are independently selected from cyano, C1-C6 alkyl, halogen, and halogen-substituted C1-C6 alkyl, respectively; n1, n2, n3, n4, n5 are independently selected from integers from 0 to 5; Het is selected from... , , , , , , Ar is selected from R5 is selected from cyano, C1-C6 alkyl, halogen-substituted C1-C6 alkyl, and n6 is selected from integers from 0 to 5; R6 is selected from hydrogen and C1-C6 alkyl; R7 is selected from C1-C6 alkyl and halogen-substituted C1-C6 alkyl.

2. The sulfonamide compound or its pesticide-acceptable salt according to claim 1, characterized in that, R1 and R4 are independently selected from cyano, C1-C3 alkyl, and halogen-substituted C1-C3 alkyl groups, respectively; R2 and R3 are independently selected from C1-C3 alkyl groups, respectively; R6 is selected from hydrogen and C1-C3 alkyl groups; R7 is selected from fluorine-substituted C1-C3 alkyl groups; and C3-C8 cycloalkyl groups are selected from... , , The substituted C3-C8 heterocycle is selected from C1-C3 alkyl-substituted C3-C8 heterocycles, amino-substituted C3-C8 heterocycles, and -N(CH3)2-substituted C3-C8 heterocycles.

3. The sulfonamide compound or its pesticide-acceptable salt according to claim 1, characterized in that, The structure of the sulfonamide compound is shown in Formula I-1: ； Among them, Het is selected from , , Ar is selected from , R 51 R 52 R 53 R 54 R 55 They are independently selected from halogens and halogen-substituted C1-C3 alkyl groups.

4. The sulfonamide compound or its pesticide-acceptable salt according to claim 3, characterized in that, Ar selected , , .

5. The sulfonamide compound or its pesticide-acceptable salt according to claim 1, characterized in that, The sulfonamide compounds are selected from the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 6. A method for preparing a sulfonamide compound or a pesticide-acceptable salt thereof according to any one of claims 1-5, characterized in that, The reaction formula for preparing the sulfonamide compound is shown below: ； Where X is a halogen; The preparation of the sulfonamide compound includes: reacting compound A and compound B under the action of an acid-binding agent to obtain a reaction solution containing the sulfonamide compound, purifying the solution to obtain the sulfonamide compound.

7. An agricultural insecticide and acaricide composition, characterized in that, Includes the sulfonamide compounds of any one of claims 1-5 or their pesticide-acceptable salts.

8. The agricultural insecticide and acaricide composition according to claim 7, characterized in that, In the agricultural insecticide and acaricide composition, the sulfonamide compound or its pesticide-acceptable salt has a mass percentage of 0.1%-99.9%.

9. The agricultural insecticide and acaricide composition according to claim 7, characterized in that, It also includes adjuvants, wherein the adjuvants in the agricultural insecticide and acaricide composition are 0.1%-99.9% by mass.

10. The use of a sulfonamide compound of any one of claims 1-5 or a pesticide-acceptable salt thereof, or an insecticidal and acaricidal composition of any one of claims 7-9, in the preparation of an insecticide and / or an acaricide.

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