Chiral, isomeric sulfite compounds and use thereof

Abstract

The application discloses a chiral, isomeric sulfite compound and preparation, separation and application of a chiral structure of the chiral, isomeric sulfite compound, and belongs to the field of agricultural technology. The application finds that the chiral, isomeric sulfite compound with the structure of a general formula (A) has excellent inhibitory activity on insect eggs, especially has a strong inhibitory effect on insect eggs of plant bugs, mites, lepidoptera, whiteflies and ladybugs, and has fungicidal activity, and absolute configurations of the chiral, isomeric sulfite compound are obtained through preparation and separation; the compound with the structure can be used for killing insect eggs and killing fungi, and has high pesticide research value and wide application prospects in the field of pesticide science.

Description

Technical Field

[0001] This invention relates to the field of agricultural technology, and in particular to a chiral, isomeric sulfite insecticide compound, and its chiral preparation, separation and application. Background Technology

[0002] The pesticide market is vast and enormous, with a market capacity approaching 10 billion yuan. Typical agricultural pesticides mainly include Orthoptera such as locusts and mole crickets; Hemiptera such as stink bugs; Homoptera including aphids, leafhoppers, and planthoppers; Thysanoptera such as thrips; Coleoptera such as beetles; Lepidoptera such as moths and butterflies; Hymenoptera such as bees and ants; Diptera such as mosquitoes, flies, and horseflies; and Grylloides such as various spider mites.

[0003] In existing pest control practices, most insecticides focus on contact and stomach poison effects against adults, nymphs, or larvae. This aims to control the pest population by significantly reducing the number of insects on crops, thereby protecting crops from excessive damage and minimizing economic losses after infestations. While this method is generally effective in controlling pest populations in the environment, it often proves less effective in controlling short-generation-cycle pests (such as various spider mites and thrips).

[0004] Taking spider mites as an example, there are numerous registered acaricides, including dozens of plant-derived, inorganic mineral, or chemical acaricides such as etoxazole, abamectin, triazophos, fenbutatin, spirodiclofen, etoxazole, veratrum root extract, and matrine. However, most of these acaricides target adult mites or nymphs, with only a few exhibiting good ovicidal activity. In the field, mites reproduce extremely rapidly, completing a generation cycle approximately every week, resulting in severe generational overlap. Therefore, if only acaricides without ovicidal activity are sprayed, although adult mites may be killed, new larvae will quickly hatch from the eggs and rapidly expand the population. While secondary applications can eliminate subsequently hatched mites, several problems arise in practical application. For example, overly frequent applications can lead to rapid development of mites' resistance. Simultaneously, the cost of pesticide application for farmers will increase exponentially. In the field, to save labor costs, traditional pesticide application methods tend to involve mixing multiple agents, such as acaricides, insecticides, fungicides, regulators, and foliar nutrients, in buckets. In actual mite control applications in the field, farmers often choose to use them in combination with ovicidal agents to extend the duration of effectiveness. However, among the registered acaricides, only etoxazole and spirodiclofen are explicitly used as ovicidal agents, making them relatively scarce. This scarcity and rising resistance are increasing the demand for new, effective dual-action acaricides that kill both mites and eggs. Simultaneously, multifunctional small-molecule acaricides are scarce. Farmers typically need to mix and apply multiple agents, such as regulators, foliar nutrients, fungicides, and ovicidal agents, in the field. Mixing multiple chemical agents with different mechanisms of action and formulations not only easily leads to antagonistic effects between agents but also easily damages the stability of the aqueous solution, causing precipitation, flocculation, and stratification, severely impacting the field application of the pesticides. At the same time, the mixing of large amounts of pesticides can easily lead to a further increase in target resistance and adverse environmental effects from pesticide residues.

[0005] Therefore, developing novel and highly effective insecticides and ovicides with novel structures and unique mechanisms of action is the key to agricultural pest control. Summary of the Invention

[0006] The purpose of this invention is to provide a chiral, isomeric sulfite insecticidal compound, which is prepared and isolated to obtain one or more absolute configurations of the compound to solve the problems existing in the prior art and achieve good inhibitory and killing effects on insect eggs.

[0007] While studying the insecticidal activity of sulfite compounds, the inventors accidentally discovered that some of these compounds had low insecticidal activity (insect population reduction rate less than 75%), but showed excellent inhibitory activity on insect eggs.

[0008] The present invention provides chiral, isomeric sulfite compounds or their meso, racemic, stereoisomer, or pharmaceutically acceptable salts having the structure shown in formula (A);

[0009]

[0010] Among them, R1 and R2 are independently selected from hydrogen, halogen, substituted or unsubstituted C1 to C2. 10 Alkyl, substituted or unsubstituted C1-C 10 Alkoxy, C2-C 10 alkoxycarbonyl, C2~C 10 Alkyl carbonyl, C1-C 10 carbonyl group;

[0011] R3, R3', R4, and R4' are each independently selected from hydrogen, C1-C5 alkyl, and C1-C5 alkenyl; or, R3, R3', R4, and R4' together with the C atoms attached to them form a five-membered heterocyclic alkyl group.

[0012] R5 is selected from halogens, substituted or unsubstituted C1-C2. 10 alkyl.

[0013] Furthermore, the structure of the compound is selected from one of the following:

[0014]

[0015] In formulas (A) and (I) to (VI), the C1 to (C5) alkyl groups are methyl or ethyl.

[0016] In formulas (A), I to VI, the C1 to C5 alkenyl groups are further selected from vinyl groups.

[0017] In formulas (A), I to VI, the five-membered heterocyclic alkyl group is further selected from...

[0018] Furthermore, R5 is selected from fluoroethyl, bromoethyl, chloroethyl, 2,2-difluoroethyl, and 2,2-dichloroethyl; R1 and R2 are independently selected from H, F, Cl, and Br.

[0019] Furthermore, R5 is -CH2CH2F; R1 and R2 are Cl.

[0020] Furthermore, the compound is selected from the following compounds:

[0021]

[0022]

[0023] In the above text, unless otherwise specified, “substitution” means that the mentioned group can be substituted by one or more additional groups, each and independently selected from alkyl, cycloalkyl, aryl, carboxyl, heteroaryl, heterocycloalkyl, hydroxyl, alkoxy, alkylthio, aryloxy, O=, guanidinyl, cyano, nitro, acyl, halogen, haloalkyl, amino, etc.

[0024] The structures of the compounds of this invention can be confirmed using conventional methods well known to those skilled in the art. If this invention relates to the absolute configuration of a compound, then that absolute configuration can be confirmed using conventional techniques in the art. According to the literature (Absolute configuration of glycosyl sulfoxides, Tetrahedron: Asymmetry, Volume 21, Issue 15, 2010, Pages 1830-1832), if the lone pair electrons of the group and sulfur are on the same side, the group is shielded, the chemical shift decreases, and the chemical shift shifts to a higher field. If the group is on the same side as the oxygen atom, the group is unshielded, the chemical shift increases, and it shifts to a lower field. The absolute configuration of the compounds is obtained by comparing and analyzing the proton NMR spectra of chiral separation compounds and by testing their optical rotation.

[0025] The compound numbers listed above are for convenience in subsequent explanations only.

[0026] The present invention provides a method for controlling and / or killing insect eggs and / or sterilizing by applying the above-mentioned compound to insect eggs and / or fungi.

[0027] Furthermore, when used to control and / or kill insect eggs, and / or for sterilization, the compound is selected from the following compounds, including mixtures of multiple configurations:

[0028]

[0029]

[0030] The intermediate compounds of the present invention can be prepared by a variety of synthetic methods known to those skilled in the art, including the specific embodiments listed herein, embodiments formed by combining them with other chemical synthetic methods, and equivalent substitutions known to those skilled in the art. Preferred embodiments include, but are not limited to, the embodiments of the present invention.

[0031] The chemical reactions in the specific embodiments of this invention are carried out in a suitable solvent, which must be suitable for the chemical changes of this invention and the reagents and materials required therefor. To obtain the compounds of this invention, it is sometimes necessary for those skilled in the art to modify or select the synthesis steps or reaction flow based on existing embodiments.

[0032] As used in this application, the term "pest" refers to an organism that adversely affects a host (e.g., a plant or an animal such as a mammal) by parasitizing, damaging, attacking, competing with, or infecting them for nutrients.

[0033] Unless otherwise specified, pests include arthropods (including insects and arachnids), and include piercing-sucking pests and biting pests (such as bedbugs, mites, ticks, ants, lice, cockroaches, thrips, etc.).

[0034] Unless otherwise specified, the insect eggs are produced by insects of the orders Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Acari, Tetranychidae, Eriophyta, Tardiidae, Pyromitidae, Chrysophagidae, or Carnivorous mites; the fungi include fungi and bacteria.

[0035] The order "Thysanoptera" belongs to the class Insecta. Insects in this order are commonly known as thrips. They are small insects with slender, elongated bodies, generally yellowish-brown or black; they have well-developed eyes, piercing-sucking mouthparts, and are asymmetrical; their wings are narrow and long, with a few veins or no veins, and the wing edges are flat and long, with hairs of varying lengths; some species are wingless or only have vestigial hairs; they lack cerci. They generally suck plant sap, harming cereals, cotton, and tobacco, and some can transmit plant viruses, making them pests. Thrips are divided into the suborders Terebrantia and Tubulifera. The suborder *Thrips* includes: the superfamily *Aeolothripoidea* (including *Aeolothripidae*, *Orothripidae*, *Melanthripidae*, *Dactuliothripidae*, and *Franklinothripidae*), the superfamily *Merothripoidea* (including *Aeolothripoidea*), and the superfamily *Thripoidea* (including *Heterothripidae*, *Hemithripidae*, *Ceratothripidae*, *Panchaetothripidae*, and *Thripidae*). Among these, *Thripidae* is the largest and most important family in this order, containing 33 genera and approximately 200 species, such as *Frankliniella intonsa*, *Thripstabaci Lindeman*, and *Taeniothrips distalis*. Karny, rice thrips (Stenchaeotothrips biformis), yellow-breasted thrips (Thrips hawaiiensis Morgan), palm thrips (Thrips palmi Karny), western flower thrips (Frankliniella occidentalis), loquat thrips (Thrips japonicus Bagnall), sugarcane thrips (Thrips serratus Kobus), rice thrips (Frankliniella tenuicornis Uzel), yellow hard thrips (Scirtothrips dorsalis Hood), greenhouse thrips (Heliothrips haemorrhoidalis Bouche), yellow thrips (Scirtothrips dorsalis Hood), and six-spotted thrips (Scolothrips sexmaculatus Pergande) are all common species in my country.The suborder *Phlaeothripoidea* includes: the superfamily *Phlaeothripoidea* (comprising Pypothripidae, Ecacanthothripidae, Eupatithripidae, Phlaeothripidae, Chirothripoididae, Hystricothripidae, Idolothripidae, and Megathripidae) and the superfamily *Urothripoidea* (comprising Urothripidae). The parentheses following each superfamily represent its subfamilies; similarly, all references to superfamilies in the following text will use this method.

[0036] The term "Hemiptera" refers to insects with a slightly flattened and rigid body; piercing-sucking mouthparts; filiform or club-shaped antennae; two ocelli or none; a well-developed pronotum with triangular scutels; forewings that are hemolecular and hindwings that are membranous, with some species having vestigial or wingless wings; most species have scent glands; the tarsi often have claws at the end, with claw pads below the claws; the abdomen has 9-11 segments, usually 10; and no cerci; it is named for its hemolecular forewings. The order Hemiptera is divided into the suborders Auchenorrhyncha and Sternorrhyncha. Auchenorrhyncha includes the superfamily Cicadoida (Cicadidae, Membracidae, Machearotidae, Cercopidae, Cicadellidae) and the superfamily Fulgoroidea (Tettigometridae, Delphacidae, Fulgoridae, Eurybrachydidae, Cixiidae, Meenoplidae, Dictyopharidae, Achilidae, Tropiduchidae, Derbidae, Lophopididae). ae, Issidae, Flatidae, Ricaniidae; the suborder Thyrocodontidae includes Psylloidea, Aleyrodoidea, Aphidoidea (Adelgidae, Phyloxeridae, Pemphigidae, Aphididae) and Coccoidea (Margarodidae, Ortheziidae, Kerridae, Kermidae, Dactylopiidae, Pseudococcidae, Asterolecaniidae, Coccidae, Diaspididae).

[0037] The "Lepidoptera" mentioned above belong to the class Insecta and have a very wide distribution, with the most abundant species in the tropics. The larvae of most species damage various cultivated plants. The larger ones often eat all the leaves or bore into the branches and trunks. The smaller ones often roll leaves, clump leaves together, form sheaths, spin webs, or burrow into plant tissues to feed. The adults mostly supplement their nutrition with nectar, or their mouthparts degenerate and they no longer feed. Lepidoptera includes the suborder Zeugloptera (family Micropterygidae), the suborder Monotrysia (superfamilies Eriocraniidea, Hepialoidea, Stigmelloidea, Incurvarioidea), and the suborder Ditrhysia (superfamilies Tinaeoidea, Cossoidea, Psychoidea, Castnioidea, Tortricoidea, Pyraloidea, Bombycoidea, Calliduloidea, Geometridae, Sphingoidea, Noctuoidea, Hesperioidea, and Papilionoidea).

[0038] The order Coleoptera is the largest and most diverse order in the class Insecta and even the animal kingdom. It is divided into the suborders Adephaga, Polyphaga, and Rhynchophora. The Adephaga suborder includes: Caraboidea (including Cicindelidae, Carabidae, Amphizoidae, Omophronidae, Hygrobiidae, Haliplidae, and Dytiscidae), Gyrinoidea (including Gyrinidae), and Paussoidea (including Paussidae). The superfamily Cupesoidea and the superfamily Rhysodoidea are included. The suborder Polyphagous includes: the superfamily Hydrophiloidea, the superfamily Staphylinoidea, the families Silphidae, Leiodidae, Clambidae, Scydmaenidae, Orthoperidae, Phaenocephalidae, and Discolomi. dae, Platypsyllidae (sea otter beetles), Cantharoidea (Lycidae, Lampyridae, Cantharidae, Drilidae, Malachiidae, Phloeophilidae, Prionoceridae, Dasytidae), Lymexyloidea (Lymexylidae, Atractoceridae), Elateroidea (feathered beetles) piceridae, Cebrionidae, Elateridae, Eucinmidae, Throscidae), Dryopoidea (Psephenidae, Helmidae, Geoyssidae, Heteroceridae), Dascilloidea, Tenebrionoidea (Alleculidae)The superfamily Ptinidae (including Lyctidae, Bostrychidae, Anobiidae, and Ptinidae), the superfamily Scarabaeoidea (including Scarabaeidae, Aegialiidae, Aphodiidae, Ochodaeidae, Geotrupidae, Trogidae, Melolonthidae, Rutelidae, Dynastidae, Cetoniidae, Trichiidae, and Passalidae), and the superfamily Cerambycoidea (including saw beetles) The families Prionidae, Cerambycidae, Lamidae, and Sagridae are all longhorn beetles. The superfamily Brentoidea includes Anthribidae, Aglycyderidae, Proterhiniidae, Cyladidae, and Curculionidae. The suborder Curculionidae includes: Curculionoidea (Anthribidae, Aglycyderidae, Proterhiniidae, Cyladidae, and Curculionidae). Common insects (common names): Ladybug, Longhorn beetle, Ladybug, Firefly, Dung beetle, Blister beetle, Rhinoceros beetle, Jewel beetle, Blastode, Scarab beetle, Stag beetle, Click beetle, Diving beetle, Rice weevil.

[0039] The "mites" mentioned in this application mainly include agricultural pests, most of which belong to the families Tetranychidae, Tenuipalpidae, Eriophyidae, Tarsonemidae, Pyemotidae, Penthhaleidae, and Cheyetidae of the class Acachnidae.

[0040] The family Tetranychus is divided into several genera: *Oligonychus* (e.g., *Oligonychus baipisongis*, *Oligonychus karamatus*, *Oligonychus rubicundus*), *Eotetranychus* (e.g., *Eotetranychus albus*, *Eotetranychus bailae*, *Eotetranychus camelliae*), *Tetranychus* (e.g., *Tetranychus neocaledonicus*, *Tetranychus phaselus*, *Tetranychus surticae*, *Tetranychus cinnabarinus*), and *Schizotetranychus* (e.g., *Schizotetranychus baltazarae*, *Schizotetranychus basilica*). * *Schizotetranychus elongatus*, etc.; *Mixonychus* (e.g., *Mixonychus (Bakerina) aestiva*, *Mixonychus (Mixonychus) ganjuis*, *Mixonychus (Bakerina) murrayae*, etc.); *Panonychus* (e.g., *Panonychus citri*, *Panonychus caglei*, *Panonychus ulmi*, etc.); *Allonychus* (e.g., *Allonychus bambusae*, *Allonychus wuyinicus*); *Stigmaeopsis* (e.g., *Stigmaeopsis*). Celarius, Stigmaeopsis nanjingensis, Monocyllus (e.g., Monocyllus georicus), Acanthonychus (e.g., Acanthonychus jiangfengensis), Amphitetranychus (e.g., Amphitetranychus hawthorn)The genera *Viennensis*, *Sonotetranychus* (e.g., *Sonotetranychus neosalix*), *Xinella* (e.g., *Xinella huangshanensis*), *Yunonychus* (e.g., *Yunonychus daliensis*), *Neotetranychus* (e.g., *Neotetranychus lek*), *Eurytetranychus* (e.g., *Eurytetranychus glycyrrhizae*, *Eurytetranychus wuyishanensis*), *Aponychus* (e.g., *Aponychus equilibris*, *Aponychus corpuzae*), and *Eutetranychus* (e.g., *Eutetranychus orientalis*, *Eutetranychus xi'anensis*). genus *Stylophoronychus* (e.g., *Stylophoronychus baghensis*), genus *Eurytetranychoides* (e.g., *Eurytetranychoides japonicus*), genus *Tenuipalpoides* (e.g., *Tenuipalpoides hastata*, *Tenuipalpoides zizyphus*), genus *Bryobia* (e.g., *Bryobia borealis*, *Bryobia exserta*), genus *Sinobryobia* (e.g., *Sinobryobia chinensis*). genus *Tetranycopsis*, genus *Petrobia* (e.g., *Petrobia xinjiangensis*, *Petrobia (Tetranychina) zachvatkini*), genus *Tetranycopsis* (e.g., *Tetranycopsis hystriciformis*, *Tetranycopsis spiraeae*), genus *Aplonobia* (e.g., *Aplonobia salsa*).The genera *Alpha alkalisalinae*, *Mesobryobia* (e.g., *Mesobryobia terpoghossiani*), and *Dolichonobia* (*Dolichonobia altaiensis*).

[0041] Furthermore, the eggs are produced by the following species: flower thrips (Frankliniella intonsa), tobacco thrips (Thrips stabaci Lindeman), bean thrips (Taeniothrips distalis Karn), rice thrips (Stenchaeotothrips biformis), yellow-breasted thrips (Thrips hawaiiensis Morgan), palm thrips (Thrips palmi Karny), western flower thrips (Frankliniella occidentalis), loquat thrips (Thrips japonicus Bagnall), sugarcane thrips (Thrips serratus Kobus), rice thrips (Frankliniella tenuicornis Uzel), tea thrips (Scirtothrips dorsalis Hood), greenhouse thrips (Heliothrips haemorrhoidalis Bouche), tea yellow thrips (Scirtothrips dorsalis Hood), and six-spotted thrips (Scolothrips). The following are listed: *Sexmaculatus Pergande*, *Cnaphalocrocis medinalis*, *Spodoptera exigua*, *Spodoptera litura*, *Carposina sasakii*, *Helicoverpaarmigera*, *Plutella xylostella*, and *Diaphania indica*.Bean pod borer (Marucatestulalis Geyer), tobacco whitefly (Bemisia tabaci Gennadius), greenhouse whitefly (Trialeurodesvaporariorum), black spiny whitefly (Aleurocanthus spiniferus), citrus whitefly (Dialeurodescitri Ashm), mulberry whitefly (Bemisiamyricae Kuwana), rice whitefly (Aleurocybotus indicus), spiral whitefly (Aleurodicus dispersus), white pine small clawed mite (Oligonychus baipisongis), larch small clawed mite (Oligonychus karamatus), red clawed mite (Oligonychus rubicundus), longhorn beetle (Cerambycidae), ladybug (Coccinellidae), firefly (Lampyridae), dung beetle (Scarabaeidae), blister beetle (Mylabrisphalerata), rhinoceros beetle (Allomyrina) dichotoma, jewel beetle (Buprestidae), blister beetle (Melyridae), scarab beetle (Scarabaeidae), stag beetle (Lucanidae), click beetle (Elateridae), water beetle (Dytiscidae), rice weevil (Sitophilus oryzae), ladybug (Harmonia axyridis), white spider mite (Eotetranychus albus), white wax spider mite (Eotetranychus bailae), camellia spider mite (Eotetranychus camelliae), cabbage leaf mite (Tetranychus neocaledonicus), bean leaf mite (Tetranychus phaselus), two-spotted spider mite (Tetranychus urticae), cinnabar spider mite (Tetranychus cinnabarinus), citrus split claw mite.

[0042] (Schizotetranychus baltazarae), bamboo splitting claw mite (Schizotetranychus bambusae), long splitting claw mite (Schizotetranychus elongatus), fig splitting claw mite (Mixonychus(Bakerina)aestiva), citrus splitting claw mite (Mixonychus(Mixonychus)ganjuis), citrus whole claw mite (Panonychus citri), Carrion whole claw mite (Panonychus caglei), bamboo anomaly claw mite (Allonychus bambusae), Wuyi anomaly claw mite (Allonychus wuyinicus), bamboo-eating elk mite (Stigmaeopsis celarius), Georgian single claw mite (Mononychellusgeorgicus), spiky second claw mite (Acanthonychus jiangfengensis), hawthorn double leaf mite (Amphitetranychus viennensis).

[0043] The fungi mentioned are selected from fungi.

[0044] In one specific embodiment of the present invention, the fungus is selected from *Rhizoctonia solani*, the rice blast pathogen. *Rhizoctonia solani* causes rice blast disease, damaging seedlings, leaves, panicles, and nodes.

[0045] The term "control" as used in this invention refers to, but is not limited to, the arbitrary killing of insect eggs, regulation of hatching, inhibition / interference with egg activity, and prevention of hatching; the term "prevention of hatching" refers to preventing or delaying the hatching of larvae from the eggs.

[0046] The term "kill" in this invention refers to the permanent loss of the insect eggs' ability to grow and hatch.

[0047] The "sterilization" described in this invention refers to the direct killing or inhibition of the growth of plant pathogens, including fungi and bacteria. The sterilization includes protective sterilization and systemic sterilization. Protective sterilization involves direct contact with pathogens outside or on the surface of the plant, killing or inhibiting the pathogens and preventing them from entering the plant, thereby protecting the plant from the harm of pathogens. Systemic sterilization, on the other hand, can be absorbed by the plant and transported within the plant to the site of pathogen infection to eliminate the pathogens.

[0048] In this invention, the sulfite compound is used to make an agricultural product, which further includes one or more of the following: excipient dispersant, wetting agent, binder, surfactant, stabilizer, and solvent.

[0049] Suitable surfactants can be selected by those skilled in the art based on actual usage requirements. Examples of surfactants that may be used in some embodiments of the invention include, but are not limited to, ethoxylated castor oil, sodium lauryl sulfate, saponins, ethoxylated alcohols, ethoxylated fatty esters, alkoxylated diols, ethoxylated fatty acids, carboxylated alcohols, carboxylic acids, fatty acids, ethoxylated alkylphenols, fatty esters, sodium dodecyl sulfide, other fatty acid-based surfactants, other natural or synthetic surfactants, and combinations thereof. In some embodiments, the surfactant is a nonionic surfactant. In some embodiments, the surfactant is an ionic surfactant. The selection of a suitable surfactant depends on the relevant application and usage conditions, and suitable surfactants are known to those skilled in the art.

[0050] In this invention, the dosage forms include, but are not limited to, emulsifiable concentrates, soluble powders, soluble granules, solutions, dispersible liquids, water-in-oil emulsions, microemulsions, microcapsule suspensions, seed treatment liquids, aerosols, etc.

[0051] Emulsifiable concentrates (ECs) are a type of pesticide formulation. They are liquids made by dissolving a high concentration of the active ingredient in a solvent and adding an emulsifier. They are typically diluted with a large amount of water to form a stable emulsion before being sprayed using a sprayer. Low-volume spraying and even ultra-low-volume spraying are also possible. They can be used directly or diluted with water before spraying.

[0052] Wettable powder is a very fine dry agent obtained by mixing and pulverizing the active ingredient, filler, surfactant and other adjuvants together.

[0053] Suspension concentrates are formulations in which solid active pharmaceutical ingredients are uniformly dispersed in water as particles smaller than 4 micrometers. Their international code is SC. They have fine particle sizes, typically 0.1–3 μm, and high suspension rates. Suspension concentrates are divided into two types: aqueous suspensions and oil suspensions. Aqueous suspensions use water as the suspension medium, while oil suspensions use oils as the suspension medium and do not contain water. Commonly used oils are vegetable oils, such as corn oil and rapeseed oil. Suspension concentrates can be used without organic solvents, making them a good dosage form for processing solid active pharmaceutical ingredients. Suspension concentrates are mixtures of solid powder and liquid suspended in water. They need to be shaken well before use and then diluted with water before spraying. Suspension concentrates are easy to carry and dilute, can be sprayed evenly, and have good adhesion and long-lasting effect.

[0054] Powder formulations refer to the original powder of the pesticide, or powder prepared by adding a certain diluent. They can be sprayed directly using a simple duster, resulting in high work efficiency, minimal adhesion to crops, low residue, and minimal risk of pesticide damage.

[0055] Granules, also known as granules, are a solid dosage form obtained by mixing and granulating the active pharmaceutical ingredient with carriers, binders, dispersants, wetting agents, stabilizers, and other adjuvants. Their performance requirements mainly include fineness, uniformity, storage stability, hardness, and disintegration properties. Granules have the largest particle size among solid dosage forms, ranging from 300 to 1700 μm in diameter, and offer advantages such as ease of use, minimal outward diffusion, and long-lasting efficacy.

[0056] Aqueous solutions are solutions of the active pharmaceutical ingredient. The drug is uniformly dispersed in water in an ionic or molecular state. The concentration of the drug depends on the water solubility of the active pharmaceutical ingredient, which is generally its maximum solubility. It is then diluted with water before use.

[0057] In this invention, the sulfite compounds can be used in combination with most commercially available agricultural formulations such as insecticides, acaricides, and fungicides to achieve synergistic effects.

[0058] Furthermore, when using sulfite compounds to control and / or kill insect eggs and / or disinfect, the concentration of the sulfite compound shall not be less than 0.1 ppm. Even further, the concentration of the sulfite compound shall not be less than 1 ppm.

[0059] The concentration of the sulfite compound used is 0.1–10000 ppm, or it can be 0.1–500 ppm, 0.1–200 ppm, 0.1–100 ppm, 0.1–50 ppm, 1–500 ppm, 1–200 ppm, 1–100 ppm, 1–50 ppm, 1–10 ppm, 1–5 ppm, 2–200 ppm, 2–100 ppm, 2–50 ppm, 2–10 ppm, 3–200 ppm, 3–100 ppm, 3–50 ppm, 3–10 ppm, 4–200 ppm, 4–100 ppm, 4–50 ppm, 4–10 ppm, or 10–1000 ppm. Specific options include, but are not limited to: 0.1ppm, 0.2ppm, 0.3ppm, 0.4ppm, 0.5ppm, 0.6ppm, 0.7ppm, 0.8ppm, 0.9ppm, 1ppm, 1.1ppm, 1.2ppm, 1.3ppm, 1.4ppm, 1.5ppm, 1.6ppm, 1.7ppm, 1.8ppm, 1.9ppm, 2.0ppm, 2.5ppm, 3ppm, 3.5ppm, 4ppm, 4.5ppm, 5ppm, 5.5ppm, 6ppm, 6.5ppm, 7ppm, 7.5ppm, 8ppm, 8.5ppm, 9ppm, 9.5ppm, 10ppm, 11ppm, 12ppm, 13ppm, 14ppm, 15ppm, 20ppm, 25ppm, 30ppm, 35ppm, 40ppm, 45ppm, 50ppm, 100ppm, etc.

[0060] Furthermore, when the sulfite compound is used to control and / or kill insect eggs, the concentration of the sulfite compound is 0.1-500 ppm; when the sulfite compound is used for sterilization, the concentration of the sulfite compound is 10-1000 ppm.

[0061] The present invention also provides a pesticide composition, wherein the active substance is a compound of formula (A).

[0062] In this invention, the pesticide composition may further include dispersants, wetting agents, binders, surfactants, stabilizers, solvents, etc.

[0063] In this invention, the pesticide composition can also be compounded with other products, including but not limited to one or more other insecticides, acaricides, fungicides, herbicides, plant growth regulators or fertilizers, and compounds with equivalent functions but not yet commercialized, thereby producing additional advantages and effects. For example, other insecticides may be flupyradifurone, deltamethrin, acetamiprid, tetrazole, imidacloprid, spirotetramat, spirodiclofen, difenoconazole, chlorfenapyr, cis-cypermethrin, brofenoxam, acetamiprid, lambda-cyhalothrin, pymetrozine, thiamethoxam, lufenuron, abamectin, chlorantraniliprole, bifenthrin, brofenoxam, diflubenzuron, spinosad, trifluralin, flonicamid, methyl pyrimiphos, indoxacarb, dinotefuran, dithion, flufenoxuron, permethrin, flufenoxuron, and flufenoxuron diethyl.

[0064] In one embodiment of the present invention, the pesticide composition further includes a mixture of ginger rhizome extract and galangal rhizome extract, wherein the ratio of ginger rhizome extract to galangal rhizome extract is 7:3. The ginger rhizome extract is obtained by extracting ginger rhizomes with ethanol and ethyl acetate at a ratio of 1–4:1; the galangal rhizome extract is volatile oil from galangal rhizomes. The mixing ratio of the above-mentioned ginger and galangal mixture with the compound of formula (A) can be (200–500):(0.1–1). Experimental studies have shown that the combined use of the two compounds has a certain synergistic effect and can reduce the concentration of the active ingredient.

[0065] As used in this application, “comprising” or “including” is interpreted in their open sense, meaning that the specified feature, element, step or component mentioned is present, but does not exclude the presence or addition of further features, elements, steps or components.

[0066] In some embodiments, any of the above compositions are applied outdoors, or to the interior or exterior of vegetation or agricultural areas and / or buildings. In some embodiments, any of the above compositions are applied to surfaces within homes, residences, or buildings. In some embodiments, any of the above compositions are applied to mattresses, sheets, fabrics, travel bags / suitcases, carpets, painted or unpainted hard surfaces, wood, flooring, furniture, and / or buildings.

[0067] In some embodiments, any of the above-described compositions are formulated in a deliverable form suitable for a particular application. These deliverable forms include, but are not limited to, liquids, emulsions, solids, waxes, dusts, fumigants, aqueous suspensions, oil dispersions, pastes, powders, dusts, emulsifiable concentrates, aerosol sprays, wood fillers, varnishes, wood treatments or furniture oils, cleaners, drywall mixtures, scented candles, caulking compositions, crack and fissure fillers, sealants, and mattress and bedding treatments. Suitable deliverable forms can be selected and formulated by those skilled in the art using methods known in the art. In different application scenarios, the above-mentioned compositions can be used in various ways, including directly, after dilution, or in concentrated form. In addition, these can be used as: a protective oil for wood or furniture; a laundry detergent; a gel or paste that can be applied to a target area; an oily emulsion; a component of dry wall materials for dust mixtures; a filler or other sealant for filling cracks or gaps; foam; a component of grout; incense mist or candles; an aerosol or spray insecticide; and a treatment for mattresses or bedspreads. In some cases, these mixtures can be used in domestic or commercial environments to combat pest eggs and fungi in a dispersed form. Furthermore, they can also be used in agricultural or other outdoor environments to control pest eggs and fungi.

[0068] The "solvent" used in the above products or compositions may be water, ketone, alcohol, aldehyde, ether, ester or carboxylic acid, and may include non-aryl ketones, non-aryl alcohols, non-aryl aldehydes, non-aryl esters, non-aryl carboxylic acids, aryl alcohols, aryl-alkyl alcohols, aryl aldehydes, aryl-alkyl ketones, aryl-aryl ketones, aryl carboxylic acids, aryl-alkyl esters, aryl-aryl esters, aryl-alkyl ethers, aryl-aryl ethers and / or combinations thereof.

[0069] In some embodiments, the solvent includes ethanol, isopropanol, benzyl alcohol, acetone, acetophenone, water, citric acid, lactic acid, glycerol, castor oil, benzoic acid, carbonic acid, ethoxylated alcohols, ethoxylated amides, glycerides, butanol, 1-propanol, hexanol, other alcohols, dimethyl ether, polyethylene glycol, etc.

[0070] The beneficial effects of this invention are as follows: This invention provides the application of chiral, isomeric sulfite compounds in inhibiting insect eggs. The chiral, isomeric sulfite compounds have a strong inhibitory effect on insect eggs, especially on the eggs of various thrips, mites, and whiteflies, which are pests of the order Thysanoptera. Compounds with this structure can be used as insecticides or ovicides, have high value in pesticide research, and have broad application prospects in the field of pesticide science. Attached Figure Description

[0071] Figure 1 Chromatogram of a mixture of compound 1 and compound 1' separated using an IG column;

[0072] Figure 2 Chromatograms showing the separation of compound 1 and compound 1' by R configuration using an IG column;

[0073] Figure 3 Chromatograms showing the separation of compound 1' and the S configuration of compound 1 using an IG column;

[0074] Figure 4 The chromatogram of the first peak separated from the R configuration in the IG column;

[0075] Figure 5 The chromatogram of the second peak separated for the R configuration in the IG column.

[0076] Figure 6 The chromatogram of the third peak separated for the R configuration in the IG column.

[0077] Figure 7 The chromatogram of the fourth peak separated by the R configuration in an IG column;

[0078] Figure 8 The chromatogram of the first peak separated from the S configuration in the IG column;

[0079] Figure 9 The chromatogram of the second peak separated from the S configuration in the IG column;

[0080] Figure 10 The chromatogram of the third peak separated from the S configuration in the IG column;

[0081] Figure 11 The first peak on the IG column after separation of the S configuration of compound 1 and compound 1' is the chromatographic peak when separated using an AS column. Detailed Implementation

[0082] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention. Furthermore, unless otherwise specified, all reagents, raw materials, and other experimental materials used in the following embodiments are commercially available or can be synthesized, cultured, or cultivated according to methods described herein or known to the public. Experimental conditions not listed are also readily available to those skilled in the art.

[0083] When numerical ranges are provided, it is understood that the intermediate values ​​between the upper and lower limits of the range (to one-tenth of the unit of the lower limit, unless the context explicitly indicates otherwise) and any other provisions or intermediate values ​​within the specified range are covered in the embodiments of this application. The upper and lower limits of these smaller ranges may independently define smaller numerical ranges, and it will be understood that these smaller ranges are intended to be covered in the embodiments of this application, subject to any explicitly excluded limits within the specified range.

[0084] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application pertains. Any methods and materials similar to or equivalent to those described herein may also be used in the practice or testing of embodiments of this application.

[0085] Example 1: Synthesis of compounds S-1 and S-1'

[0086]

[0087] Step 1:

[0088]

[0089] 2,4-Dichlorophenol (500 mg, 3.1 mmol), R-propylene oxide (356 mg, 6.1 mmol), DMF (12 mL), and cesium carbonate (4.0 g, 12.3 mmol) were added to a reaction flask and heated to 100°C under reflux. The reaction was monitored by TLC. After the reaction was complete, the mixture was concentrated, and the residue was dissolved in water (10 mL) and ethyl acetate (50 mL). The mixture was separated, and the aqueous phase was extracted with ethyl acetate (50 mL x 2). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and column chromatography was performed to obtain compounds iii-1 and iii-1' (total 511 mg, colorless, transparent oil).

[0090] Step 2:

[0091]

[0092] Thionium chloride (415 mg, 3.5 mmol) was added to a reaction flask and dissolved in 15 mL of dichloromethane. The mixture was then stirred in an ice bath at 0 °C, and a mixture of compounds iii-1 and iii-1' (511 mg, 2.3 mmol) was slowly added dropwise. After the addition was complete, the mixture was allowed to react at room temperature for 10 h. Once the reaction was complete as monitored by TLC, the reaction solution was concentrated under reduced pressure to obtain a pale yellow oily substance, which was the crude product of compounds v-1 and v-1', and was set aside for later use.

[0093] Step 3:

[0094]

[0095] Compound vi-1 (224 mg, 3.5 mmol) was added to a reaction flask, followed by triethylamine (349 mg, 3.5 mmol). The flask was then heated in an ice bath at 0 °C, and a mixture of compounds v-1 and v-1' (690 mg, 2.3 mmol) was slowly added dropwise. After the addition was complete, the mixture was allowed to react at room temperature for 6 h. Once the reaction was complete as monitored by TLC, 100 mL of water was added to the reaction solution, and the mixture was extracted with dichloromethane (30 mL × 3). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain a mixture of compounds S-1 and S-1' (501 mg, colorless transparent liquid).

[0096] Example 2: Synthesis of compounds R-1 and R-1'

[0097]

[0098] In Example 1, R-propylene oxide was replaced with S-propylene oxide, and the mixture of compounds R-1 and R-1' (515 mg, colorless transparent liquid) was synthesized according to the synthesis method of Example 1.

[0099] Example 3: Chiral separation of compounds S-1, S-1', R-1, and R-1'

[0100] 1 Experimental Methods

[0101] 1.1 Isolation of Compounds

[0102] Preliminary analysis indicated that the sulfite compounds possessed two chiral centers. Using chiral starting materials, they were synthesized and then separated to obtain eight components. Instrumentation: Shimadzu preparative high-performance liquid chromatography (HPLC), LC20AR; Chiral column: Positive IG column, Normal-phase AS column, 4.6 mm ID × 250 mm, diameter: 5 μm; mobile phase: n-hexane:isopropanol = 95:5. The S mixture of compounds 1 and 1' was separated into 3 components by IG column chromatography, and the R mixture of compounds 1 and 1' was separated into 4 components by IG column chromatography. Further separation of the 7 separated components by AS column chromatography revealed that the first peak in the S configuration of compounds 1 and 1' contained 2 components. After further separation, a total of 8 components were obtained.

[0103] In the synthesis of compound 1, the first step reaction results in two products, iii-1 and iii-1', due to the different ring-opening positions. These products can be separated using chiral preparative chromatography. Instrumentation: Shimadzu high-performance liquid chromatography (HPLC) LC20AR; chiral column: Normal-phase IG column, 4.6 mm ID × 250 mm, diameter: 5 μm; mobile phase: n-hexane:isopropanol = 90:10. (The same conditions were used for the separation of iii-4, iii-4', etc.)

[0104] 1.2 Determination of the absolute configuration of the compound

[0105] 1.2.1 Compound proton spectrum testing

[0106] According to the literature (Absolute configuration of glycosyl sulfoxides, Tetrahedron: Asymmetry, Volume 21, Issue 15, 2010, Pages 180-1832, https: / / doi.org / 10.1016 / j.tetasy.2010.06.019.), if the lone pair electrons of the group and sulfur are on the same side, the group is shielded, the chemical sites decrease, and the chemical shift moves to a higher field. If the group is on the same side as the oxygen atom, the group is deshielded, the chemical shift increases, and it moves to a lower field. Based on this result, by analyzing the NMR data of the isolated compound, its absolute configuration is inferred as follows:

[0107]

[0108] 1-(R,R): 1H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.90(td,J=6.6,4.1Hz,1H),4.62(dd,J=5.1,3.1Hz,1H),4.53–4.45(m,1H),4.37–4.10(m,2H),3.98(qd,J=10.0,5.4Hz,2H),1.39(d,J=6.5Hz,3H)ppm.

[0109] 1-(R,S): 1 H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.6Hz,1H),6.85(d,J=8.8Hz,1H),4.64–4.55(m,1H),4.55–4.38(m,2H),4.22–4.11(m,3H),4.04(dd,J=11.2,4.1Hz,1H),1.32(d,J=6.3Hz,3H)ppm.

[0110] 1-(S,R): 1 H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.6Hz,1H),6.85(d,J=8.8Hz,1H),4.6463–4.55(m,1H),4.55–4.38(m,2H),4.24–4.11(m,3H),4.04(dd,J=11.2,4.1Hz,1H),1.32(d,J=6.3Hz,3H)ppm.

[0111] 1-(S,S): 1 H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.90(td,J=6.6,4.1Hz,1H),4.62(dd,J=5.1,3.1Hz,1H),4.56–4.45(m,2H),4.37–4.10(m,2H),3.98(qd,J=10.0,5.4Hz,2H),1.39(d,J=6.5Hz,3H)ppm..

[0112] 1’-(S,R): 1H NMR(400MHz,CDCl3)δ7.30(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.88(pd,J=6.4,4.4Hz,1H),4.68–4.56(m,1H),4.55–4.45(m,1H),4.34–4.11(m,2H),4.01(dd,J=10.0,6.3Hz,1H),3.93(dd,J=10.0,4.3Hz,1H),1.43(d,J=6.5Hz,3H)ppm.

[0113] 1’-(S,S): 1 H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.90(td,J=6.6,4.1Hz,1H),4.62(dd,J=5.1,3.1Hz,1H),4.53–4.45(m,1H),4.37–4.10(m,2H),3.98(qd,J=10.0,5.4Hz,2H),1.39(d,J=6.5Hz,3H)ppm. 1

[0114] 1’-(R,R): 1 H NMR(400MHz,CDCl3)δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.90(td,J=6.6,4.1Hz,1H),4.69–4.57(m,1H),4.57–4.46(m,1H),4.36–4.09(m,2H),3.98(qd,J=10.0,5.4Hz,2H),1.39(d,J=6.5Hz,3H)ppm.

[0115] 1’-(R,S): 1H NMR (400MHz, CDCl3) δ7.30(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.76(d,J=8.8Hz,1H),4.88(td,J=6.4,4.3Hz,1H),4.65–4.57( m,1H),4.50(td,J=3.9,3.3,1.5Hz,1H),4.32–4.12(m,2H),4.01(dd,J=10.0,6.3Hz,1H),3.93(dd,J=10.0,4.3Hz,1H),1.43(s,3H)ppm.

[0116] 1.2.2 Determination of the specific rotation of compounds

[0117] Using chloroform as solvent, at a concentration of 1 mg / mL, its specific rotation was measured at 25 degrees Celsius. The specific data are as follows:

[0118] 1-(S,R): [α] 25 D = -10.00

[0119] 1-(S,S): [α] 25 D = -9.00

[0120] 1-(R,R): [α] 25 D = +10.00

[0121] 1-(R,S): [α] 25 D = +10.00

[0122] 1'-(R,S): [α] 25 D = -8.00

[0123] 1'-(R,R): [α] 25 D = +41.00

[0124] 1'-(S,R): [α] 25 D = +7.00

[0125] 1'-(S,S): [α] 25 D = -38.00

[0126] The specific rotation results are consistent with the absolute configuration predicted by NMR analysis; therefore, the product configuration should be correct.

[0127] Example 4 Synthesis of Compound 1

[0128]

[0129] Step 1:

[0130]

[0131] 2,4-Dichlorophenol (1 g, 6.2 mmol) was added to a reaction flask and dissolved in 20 mL of DMF. Propylene oxide (722 mg, 7.6 mmol) and cesium carbonate (8 g, 24.8 mmol) were added, and the mixture was heated in an oil bath at 100 °C. After 6 h, the reaction was monitored by TLC until complete. 100 mL of water was added, and the mixture was extracted with ethyl acetate (30 mL × 3). After washing with saturated brine, the organic phase was collected, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by separation and chiral preparation (instrument: Shimadzu preparative high-performance liquid chromatography, LC20AR; chiral column: [instrument missing]). Normal-phase IG column, 4.6 mm I.D. × 250 mm, diameter: 5 μm; mobile phase: n-hexane:isopropanol = 90:10) to give compound iii-1 (356 mg, colorless transparent liquid).

[0132] Step 2:

[0133]

[0134] Thionyl chloride (293 mg, 2.5 mmol) was added to a reaction flask and dissolved in 20 mL of dichloromethane. The mixture was then stirred in an ice bath at 0 °C, and compound iii-1 (356 mg, 1.6 mmol) was slowly added dropwise. After the addition was complete, the mixture was allowed to react at room temperature for 10 h. Once the reaction was complete as monitored by TLC, the reaction solution was concentrated under reduced pressure to obtain a pale yellow oily substance, which was the crude product of compound v-1, and was set aside for later use.

[0135] Step 3:

[0136]

[0137] Compound vi-1 (123 mg, 1.9 mmol) was added to a reaction flask, followed by the addition of triethylamine (243 mg, 2.4 mmol). The flask was then heated in an ice bath at 0 °C, and compound v-1 (480 mg, 1.6 mmol) was slowly added dropwise. After the addition was complete, the mixture was allowed to react at room temperature for 6 h. Once the reaction was complete as monitored by TLC, 100 mL of water was added to the reaction mixture, and the mixture was extracted with dichloromethane (30 mL × 3). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain compound 1 (423 mg, oil).

[0138] 1H NMR (400MHz, CDCl3) δ7.50(d,J=1.4Hz,1H),7.30–7.27(m,1H),7.08(d,J=7.5Hz,1H),4.87(t,J=2.9Hz,1H),4.75(t,J=2.9Hz,1H) ,4.64–4.54(m,1H),4.51–4.46(m,1H),4.14–4.10(m,1H),3.95(t,J=2.8Hz,1H),3.88(t,J=2.9Hz,1H),1.40(d,J=5.7Hz,3H)ppm.

[0139] HRMS(ESI)Calcd.For C 11 H 14 Cl2FO4SNa + [M+Na] + 352.9768; Found:352.9789,354.9773

[0140] Example 5 Synthesis of Compound 1'

[0141]

[0142] Step 1:

[0143]

[0144] Following step 1 of Example 4, the target compound iii-1' was prepared chirally.

[0145] Step 2: Same as step 2 in Example 1

[0146] Step 3: Same as step 3 in Example 1

[0147] The target compound 1' (674 mg, colorless and transparent liquid) was obtained by synthesis.

[0148] 1 H NMR (400MHz, CDCl3) δ7.39(d,J=2.5Hz,1H),7.20(dd,J=8.8,2.5Hz,1H),6.85(d,J=8.8Hz,1H),5.01-4.93(m,1H),4.74–4.66(m,1H),4.63 –4.55(m,1H),4.40-4.31(m,1H),4.31-4.22(m,1H),4.10(dd,J=10.0,6.3Hz,1H),4.02(dd,J=10.0,4.3Hz,1H),1.52(d,J=6.5Hz,3H)ppm.

[0149] HRMS(ESI)Calcd.For C 11 H 14 Cl2FO4SNa + [M+Na] + 352.9768; Found:352.9786,354.9758.

[0150] Example 6 Synthesis of Compound 10

[0151]

[0152] Step 1:

[0153]

[0154] Following step 1 of Example 4, the target compound iii-10 was prepared chirally.

[0155] Step 2: Same as step 2 in Example 1

[0156] Step 3: Same as step 3 in Example 1

[0157] The target compound 10 (685 mg, colorless and transparent liquid) was obtained by synthesis.

[0158] 1 H NMR (400MHz, CDCl3) δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.6Hz,1H),6.75(d,J=8.8Hz,1H),4.61–4.57( m,1H),4.49–4.45(m,1H),4.30–2.34(m,1H),4.21–4.18(m,1H),3.92(s,2H),1.58(s,3H),1.57(s,3H)ppm.

[0159] HRMS(ESI)Calcd.For C 12 H 16 Cl2FO4S + [M+H] + 345.0125; Found: 345.0143.

[0160] Example 7 Synthesis of Compound 10'

[0161]

[0162] Step 1:

[0163]

[0164] Following step 1 of Example 6, the target compound iii-10' was prepared chirally.

[0165] Step 2: Same as step 2 in Example 1

[0166] Step 3: Same as step 3 in Example 1

[0167] The target compound 10' (311 mg, colorless transparent liquid) was obtained by synthesis.

[0168] 1 H NMR (400MHz, CDCl3) δ7.31(d,J=2.5Hz,1H),7.11(dd,J=8.8,2.6Hz,1H),6.75(d,J=8.8Hz,1H),4.61–4.57( m,1H),4.49–4.45(m,1H),4.30–2.34(m,1H),4.21–4.18(m,1H),3.92(s,2H),1.58(s,3H),1.57(s,3H)ppm.

[0169] HRMS(ESI)Calcd.For C 12 H 16 Cl2FO4S + [M+H] + 345.0125; Found: 345.0126.

[0170] Example 8 Synthesis of Compound 19

[0171]

[0172] Step 1:

[0173]

[0174] Following step 1 of Example 4, propylene oxide was replaced with 1,2-epoxybutane, and the target compound iii-19 was prepared chirally.

[0175] Step 2: Same as step 2 in Example 1

[0176] Step 3: Same as step 3 in Example 1

[0177] The target compound 19 (692 mg, colorless and transparent liquid) was obtained by synthesis.

[0178] 1H NMR (400MHz, CDCl3) δ7.32–7.29(m,1H),7.14–7.09(m,1H),6.85–6.81(m,1H),4.75–3.96(m,7H),1.86-1.66(m,2H),0.98(t,J=6.7Hz,3H)ppm.

[0179] HRMS(ESI)Calcd.For C 12 H 15 O4Cl2FS + [M+H] + 344.0052; Found: 344.0026.

[0180] Example 9 Synthesis of Compound 19'

[0181]

[0182] Step 1:

[0183]

[0184] Following step 1 of Example 8, the target compound iii-19' was prepared chirally.

[0185] Step 2: Same as step 2 in Example 1

[0186] Step 3: Same as step 3 in Example 1

[0187] The target compound 19' (309 mg, colorless and transparent liquid) was obtained by synthesis.

[0188] 1 H NMR (400MHz, CDCl3) δ7.32–7.29(m,1H),7.14–7.09(m,1H),6.85–6.81(m,1H),4.75–3.96(m,7H),1.86-1.66(m,2H),0.95(t,J=6.8Hz,3H)ppm.

[0189] HRMS(ESI)Calcd.For C 12 H 13 O4Cl2FS + [M+H] + 341.9896; Found: 341.9903.

[0190] Example 10 Synthesis of Compound 22

[0191]

[0192] Step 1:

[0193]

[0194] Following step 1 of Example 4, propylene oxide was replaced with butylene oxide, and the target compound iii-22 was prepared chirally.

[0195] Step 2: Same as step 2 in Example 1

[0196] Step 3: Same as step 3 in Example 1

[0197] The target compound 22 (671 mg, colorless and transparent liquid) was obtained by synthesis.

[0198] 1 H NMR (400MHz, CDCl3) δ7.31(dd,J=2.6,1.4Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.77(dd,J=8.8,1.2Hz,1H),5.95–5.87(m,1H),5.48(d, J=17.2,Hz,1H),5.39-5.33(m,1H),5.17-5.10(m,1H),4.65-4.56(m,1H),4.54-4.45(m,1H),4.40-4.12(m,2H),4.06-3.97(m,2H)ppm.

[0199] HRMS(ESI)Calcd.For C 12 H 13 O4Cl2FS + [M+H] + 341.9896; Found: 341.9857.

[0200] Example 11 Synthesis of Compound 22'

[0201]

[0202] Step 1:

[0203]

[0204] Following step 1 of Example 6, the target compound iii-22' was prepared chirally.

[0205] Step 2: Same as step 2 in Example 1

[0206] Step 3: Same as step 3 in Example 1

[0207] The target compound 22' (297 mg, colorless and transparent liquid) was obtained by synthesis.

[0208] 1 H NMR (400MHz, CDCl3) δ7.31(dd,J=2.6,1.4Hz,1H),7.11(dd,J=8.8,2.5Hz,1H),6.77(dd,J=8.8,1.2Hz,1H),5.95–5.87(m,1H),5.48(d, J=17.2,Hz,1H),5.39-5.33(m,1H),5.17-5.10(m,1H),4.65-4.56(m,1H),4.54-4.45(m,1H),4.40-4.12(m,2H),4.06-3.97(m,2H)ppm.

[0209] HRMS(ESI)Calcd.For C 12 H 13 O4Cl2FS + [M+H] + 341.9896; Found: 341.9903.

[0210] Example 12 Synthesis of Compound 25

[0211]

[0212] Step 1:

[0213]

[0214] Following step 1 of Example 4, propylene oxide was replaced with 3,4-epoxytetrahydrofuran to obtain the target compound iii-25.

[0215] Step 2: Same as step 2 in Example 1

[0216] Step 3: Same as step 3 in Example 1

[0217] The target compound 25 (703 mg, colorless and transparent liquid) was obtained by synthesis.

[0218] 1 H NMR (400MHz, CDCl3) δ7.34–7.31(m,1H),7.15(d,J=8.8,Hz,1H),6.86(d,J=8.8Hz,1H),5.09(dd,J=4.0Hz ,1H),4.82(d,J=4.4Hz,1H),4.65–4.61(m,1H),4.52–4.57(m,1H),4.25-14(m,4H),4.01-3.87(m,2H)ppm.

[0219] HRMS(ESI)Calcd.ForC 13 H13 O5Cl2F + [M+H] + 339.0124; Found: 339.0150.

[0220] Example 13 Synthesis of Compound 28

[0221]

[0222] Step 1:

[0223]

[0224] Following step 1 of Example 6, propylene oxide was replaced with ethylene carbonate to obtain the target compound iii-28.

[0225] Step 2: Same as step 2 in Example 1

[0226] Step 3: Same as step 3 in Example 1

[0227] The target compound 22 (671 mg, colorless and transparent liquid) was obtained by synthesis.

[0228] 1 H NMR (400MHz, CDCl3) δ7.31 (d, J=2.5Hz, 1H), 7.12 (dd, J=8.8, 2.5Hz, 1H), 6.78 (d, J=8.8 Hz,1H),4.65–4.62(m,1H),4.53–4.49(m,1H),4.34–4.30(m,2H),4.25–4.18(m,3H)ppm.

[0229] HRMS(ESI)Calcd.For C 10 H 11 O4Cl2FS + [M+H] + 316.9739; Found: 316.09658.

[0230] The remaining compounds were synthesized using the same method described above.

[0231] Experimental Example 1: Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S), compound 1, and compound 1' on the hatching of Tetranychus cinnabarinus eggs.

[0232] 1 Experimental Methods

[0233] (1) Preparation of leaf discs containing eggs: 20 adult female Tetranychus carmineus were transferred to broad bean leaf discs with a diameter of 2.0 cm (with moistened filter paper at the bottom). The discs were then covered with covered culture dishes and kept moist. The adult mites were removed within 36 hours, and the leaf discs containing eggs were examined and counted under a microscope.

[0234] (2) Egg count survey: Before soaking in the drug, the egg count of each leaf disc was investigated by microscopic examination, and each treatment was repeated twice.

[0235] (3) Immersion treatment: The leaf discs carrying mite eggs were immersed in water and sulfite compounds for 10 seconds respectively, and then removed and kept moist for incubation. Each treatment was repeated no less than 3 times.

[0236] (4) Cultivation and observation: The treated mite eggs and leaf discs were cultured under normal conditions. Five days after the treatment, the hatching of the spider mite eggs was investigated.

[0237] Note: After treatment, the temperature and humidity conditions of the constant temperature and humidity incubator should be carefully controlled to avoid excessive temperature differences, which could cause condensation to form in the dish and drip down, leading to abnormal death of the eggs due to water immersion; it is also necessary to ensure sufficient strong light in the environment, but not direct sunlight on the leaf surface.

[0238] (5) Results Investigation: The experimental materials in each treatment group were regularly hydrated and moisturized, and the hatching status of the eggs was observed. The number of hatched eggs in each treatment was recorded on the 7th day after the drug was applied, and the investigation results were recorded in the original record book. The investigation period may be shortened or extended depending on the experimental requirements and the characteristics of the drug.

[0239] Survey indicators:

[0240] ① Investigate and record the number of hatched eggs for each treatment.

[0241] ② Take photos to record whether the broad bean leaves have suffered pesticide damage.

[0242] ③ Record the developmental status of the test mite eggs and the behavior of the nymphs, such as delayed or stopped development of the mite eggs, difficulty in hatching the nymphs, or painful struggles after hatching.

[0243] (6) Calculation method: Based on the survey data, calculate the prevention effect of each treatment according to the following formula, and keep the calculation results to two decimal places.

[0244] Egg hatching rate (%) = (Number of hatched eggs / Total number of eggs processed) * 100

[0245] Control effect (%) = (hatching rate of eggs in control area - hatching rate of eggs in treatment area) / hatching rate of eggs in control area) * 100.

[0246] The experimental design is shown in Table 1.

[0247] Table 1 Experimental Design

[0248]

[0249]

[0250] 2 Experimental Results

[0251] The results are shown in Table 2. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), and compound 1 and compound 1' all showed excellent inhibitory effects on the hatching of Tetranychus cinnabarinus eggs at 1 ppm.

[0252] Table 2

[0253]

[0254]

[0255] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on thrips egg hatching in Experiment Example 2

[0256] This experiment adopted the method described in Experiment 1 of the technical section, primarily using the leaf-disc method to explore the effects of 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the inhibition of thrips egg hatching. The concentration of all compounds was 100 ppm.

[0257] The experimental results are shown in Table 3. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S) and compound 1 and compound 1' showed strong inhibitory activity against thrips egg hatching at 100 ppm.

[0258] Table 3

[0259]

[0260] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of Tetranychus taeniorhynchus eggs in Experiment Example 3

[0261] This experiment adopted the method described in Experiment Example 1 of the technical section, primarily using the leaf disc method to explore the effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the inhibition of hatching of Tetranychus spp. eggs. The concentration of all compounds was 5 ppm.

[0262] The experimental results are shown in Table 4. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S) and compound 1 and compound 1' showed strong inhibitory activity against the hatching of Tetranychus tinctoria eggs at 5 ppm.

[0263] Table 4

[0264]

[0265] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of eggs of *Pachycerium citrinum* in Experiment Example 4

[0266] This experiment adopted the method described in Experiment Example 1 of the technical section, primarily using the leaf-dish method to explore the effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of eggs of *Pachycercus citrus*. The concentration of all compounds was 1 ppm.

[0267] The experimental results are shown in Table 5. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S) and compound 1 and compound 1' all showed good inhibitory effects on the hatching of Citrus moniliforme eggs at 1 ppm.

[0268] Table 5

[0269]

[0270]

[0271] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of whitefly eggs in Experiment Example 5

[0272] This experiment adopted the method of Experiment 1 in the technical section, mainly using the leaf-dish method to explore the effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the inhibition of whitefly egg hatching. The concentration of all compounds was 10 ppm.

[0273] The experimental results are shown in Table 6. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S) and compound 1 and compound 1' showed strong inhibitory activity against whitefly egg hatching at 10 ppm.

[0274] Table 6

[0275]

[0276] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of Spodoptera litura eggs in Experiment Example 6

[0277] 1 Experimental Design

[0278] (1) Preparation of egg-containing paper: Cut the egg mass into small pieces, each piece containing about 60 eggs, and soak the egg-laying paper together in the pre-prepared test reagent for 10 minutes (the concentration of the compounds is 500 ppm). After taking it out, use absorbent paper to absorb the excess solution adhering to the egg-laying paper and egg mass.

[0279] (2) Culture: Place each egg mass into a glass test tube (5.0 cm high and 2.5 cm in diameter, the same below), seal the tube with plastic film with fine holes punched with an insect needle, and place it in an artificial climate chamber with (24±1)℃, (80±10)% relative humidity and photoperiod L∶D=12∶12. When the eggs are about to hatch, add castor bean leaves with a diameter of about 3 cm for the hatched larvae to feed on.

[0280] (3) Observation: Check and record the number of hatched and unhatched eggs for each egg mass, and calculate the hatching rate according to the formula. Each treatment was repeated 3 times.

[0281] (4) Results Investigation: The experimental materials in each treatment group were regularly hydrated and moisturized, and the hatching status of the eggs was observed. The number of hatched eggs in each treatment was recorded on the 4th day after the drug was applied, and the investigation results were recorded in the original record book. The investigation period may be shortened or extended depending on the experimental requirements and the characteristics of the drug.

[0282] Survey indicators:

[0283] ① Investigate and record the number of hatched eggs for each treatment.

[0284] ② Record the developmental status of the beet armyworm eggs and the behavior of the nymphs, such as any abnormal phenomena such as delayed or stopped development of the beet armyworm eggs.

[0285] (5) Calculation method: Based on the survey data, calculate the prevention effect of each treatment according to the following formula. The calculation results are all retained to two decimal places.

[0286] Egg hatching rate (%) = (Number of hatched eggs / Total number of eggs processed) * 100

[0287] Control efficacy (%) = (hatching rate of eggs in control area - hatching rate of eggs in treatment area) / hatching rate of eggs in control area) * 100

[0288] 2 Experimental Results

[0289] The experimental results are shown in Table 7. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), and 1'-(R,S) showed good inhibitory activity against the hatching of Spodoptera litura eggs at 500 ppm.

[0290] Table 7

[0291]

[0292] Effects of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' on the hatching of Heterochromis heterochromis eggs in Experiment 7

[0293] 1. Test Plan

[0294] Ladybug egg cards (each card containing approximately 20 eggs) were purchased from Jiyuan Baiyun Industrial Co., Ltd., Henan Province. The number of eggs on each card was used as the baseline before treatment. Five egg cards constituted one treatment, with three replicates per treatment. The egg cards were immersed in a 100 ppm solution for 30 seconds, then removed, air-dried, and cultured under moist conditions. The treated mite eggs and leaf discs were incubated at 27°C. Hatching of the ladybug eggs was investigated four days after treatment. The control efficacy was calculated using the following formula.

[0295] Egg hatching rate (%) = (Number of hatched eggs / Total number of eggs processed) * 100

[0296] Control efficacy (%) = (hatching rate of eggs in control area - hatching rate of eggs in treatment area) / hatching rate of eggs in control area) * 100

[0297] 2. Experimental Results

[0298] The experimental results are shown in Table 8. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S) and compound 1 and compound 1' showed strong inhibitory activity against the hatching of Heterochromis heterochromis eggs at 100 ppm.

[0299] Table 8

[0300]

[0301]

[0302] Preliminary screening of fungicidal (rice blast pathogen) activity of compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) with compounds 1 and 1' in Experimental Example 8

[0303] 1 Experimental Design

[0304] Experimental materials: culture medium, activated bacteria, sterile water, 96-well plate, and multi-well pipette.

[0305] Rapid screening system (200 μL): culture medium (150 μL) + drug (40 μL) + bacteria (10 μL).

[0306] Experimental steps: Prepare reagents, add culture medium, add reagents, add bacteria, and detect.

[0307] (1) Preparation of the drug: Prepare the drug to a final concentration of 100 ppm and transfer the prepared drug into a 1.5 mL centrifuge tube for later use.

[0308] (2) Use a pipette to add the culture medium and reagents into the prepared 96-well plate.

[0309] (3) Preparation of inoculum: Take a culture dish (for rice blast pathogen), add 15 mL of sterile water, and slide a pipette tip across the surface of the hyphae to break them and dissolve them in the sterile water. Take 10 μL of the bacterial suspension and examine it under a microscope, ensuring that there are at least 10 hyphae in the field of view. Culture the bacteria to OD600 = 1.0, then dilute 1000 times to obtain the inoculum; the number of oomycete zoospores should be at least 1*10^6. 5 / mL.

[0310] (4) Detection: Fungi were measured at OD=450nm, and bacteria at OD=600nm, recorded as 0-hour data. After incubation for the corresponding time, growth data were recorded, and the inhibition rate was calculated according to the formula.

[0311] Antibacterial rate (%) = ((blank control OD(72h) - blank control OD(0h)) - (treatment OD(72h) - treatment OD(0h)) / blank control OD(72h) - blank control OD(0h)) * 100

[0312] 2 Experimental Results

[0313] The experimental results are shown in Table 9. Compounds 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'-(S,R), 1'-(R,R), 1'-(R,S) and compounds 1 and 1' showed strong inhibition rates against rice blast pathogens at 100 ppm. In particular, compounds 1-(S,S), 1-(R,R), 1'-(R,S), 1'-(S,R), compounds 1 and 1' showed inhibition rates of over 90%.

[0314] Table 9

[0315]

[0316] Experimental Example 9: Effects of sulfite compounds on the hatching of Tetranychus cinnabarinus eggs

[0317] 1 Experimental Methods

[0318] This experiment adopted the method described in Experiment Example 1 of the technical section, primarily using the leaf disc method to explore the effects of compounds 1-30 and 1'-24' on the hatching of eggs of *Pseudomonas citrus*. The concentration of all compounds was 100 ppm.

[0319] 2 Experimental Results

[0320] The experimental results are shown in Table 10. The hatching rate of all compounds was less than 15%, and they all showed good activity in killing acaricide eggs.

[0321] Table 10

[0322]

[0323]

[0324] Example 10

[0325] A mixture of ginger extract and galangal volatile oil was prepared in a ratio of 7:3. This mixture was then compounded with compounds 1, 10, and 19. Based on the experimental method of Example 1, the leaf disc method was used to investigate the control effect on Tetranychus cinnabarinus eggs.

[0326] Ginger extract is prepared by extracting ginger rhizomes using a mixed solvent of ethyl acetate and ethanol in a ratio of 1:4.

[0327] Bliss, based on his concept of independent combined action, believes that the theoretical mortality rate P when insecticides and acaricides are mixed can be calculated using the following formula:

[0328] P = Pm + Pn(1 - Pm)

[0329] Pm represents the target mortality rate (%) of the first active component at a concentration of m; Pn represents the target mortality rate (%) of the second active component at a concentration of n.

[0330] If the actual mortality rate of the target is greater than the theoretical mortality rate P after the two active components are mixed at a certain concentration, it is determined that the two active components have a synergistic effect when used together at the set concentration; otherwise, they have an antagonistic effect.

[0331] The experimental results are shown in Table 11. Compounds 1, 10 and 19, when combined with a mixture of ginger and sand ginger, have a synergistic effect on the control of spider mite eggs.

[0332] Table 11

[0333]

[0334]

[0335]

[0336] The above embodiments are merely illustrative of the principles and effects of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by those skilled in the art without departing from the spirit and technical concept disclosed in the present invention should still be covered by the claims of the present invention.

Claims

1. A compound, characterized in that, The compound is selected from one of the following compounds: 。 2. A method for controlling and / or killing insect eggs, or for sterilization, characterized in that, The compound of claim 1 is applied to insect eggs and / or fungi.

3. The method according to claim 2, characterized in that, When used to control and / or kill insect eggs, and / or for sterilization, the compound is selected from one or a mixture of two or more of the following compounds: 。 4. The method according to claim 2, characterized in that, The insect eggs are produced by insects of the orders Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Tetranychidae, Avesidae, Eriophyridae, Tardiidae, Pyromitidae, Lepidoptera, or Carnivorous mites; the fungi include fungi and bacteria.

5. The method according to claim 2, characterized in that, The eggs are laid by various insect species, including flower thrips, tobacco thrips, bean thrips, rice thrips, yellow-breasted thrips, palm thrips, western flower thrips, melon thrips, loquat thrips, sugarcane thrips, rice thrips, tea yellow thrips, greenhouse thrips, tea yellow thrips, six-spotted thrips, rice leaf roller, tobacco whitefly, greenhouse whitefly, black spiny whitefly, citrus whitefly, mulberry whitefly, rice whitefly, spiral whitefly, white pine small claw mite, larch small claw mite, carmine small claw mite, ladybug, longhorn beetle, ladybug, firefly, and dung beetle. The fungus is a blister beetle, rhinoceros beetle, jewel beetle, blister beetle, scarab beetle, stag beetle, click beetle, water beetle, rice weevil, white spider mite, white wax spider mite, camellia spider mite, cabbage spider mite, bean spider mite, two-spotted spider mite, cinnabar spider mite, citrus split claw mite, bamboo split claw mite, long split claw mite, fig split claw mite, citrus split claw mite, citrus whole claw mite, caryopsis whole claw mite, bamboo anomaly, Wuyi anomaly, bamboo-eating elk mite, Georgian single claw mite, sharp-peaked second claw mite, hawthorn double-leaved mite; the fungus is the rice blast pathogen.

6. The method according to claim 2, characterized in that, The concentration of the compound used is not less than 0.1 ppm.

7. The method according to claim 2, characterized in that, When used, the compound is formulated into an agricultural product, which further includes one or more of the following: excipient dispersant, wetting agent, binder, emulsifier, stabilizer, and solvent.

8. The method according to claim 7, characterized in that, The formulations of the agricultural products are emulsifiable concentrates, suspension concentrates, wettable powders, powders, granules, aqueous solutions, mother liquors, or mother powders.

9. A pesticide composition, characterized in that, The compound of claim 1 is used as the active substance.

10. The pesticide composition according to claim 9, characterized in that, It also includes a mixture of ginger rhizome extract and sand ginger rhizome extract, with a ginger rhizome extract: sand ginger rhizome extract ratio of 7:

3. The ginger rhizome extract is obtained by extracting ginger rhizomes with ethanol: ethyl acetate in a ratio of 1 to 4:

1. The sand ginger rhizome extract is the volatile oil of sand ginger rhizomes.

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