Chiral and Isomeric Sulfonate Compound and its Applications
Chiral and isomeric sulfonate compounds address the ovicidal gap in current pesticides, effectively controlling pest eggs and preventing population resurgence with improved formulation stability and reduced environmental harm.
Patent Information
- Authority / Receiving Office
- BR · BR
- Patent Type
- Applications
- Current Assignee / Owner
- CHENGDU HANOVA BIOSCIENCES CO LTD
- Filing Date
- 2025-05-13
- Publication Date
- 2026-07-14
AI Technical Summary
Current pesticide methods fail to effectively control short-lived pests like red mites and thrips due to a lack of ovicidal activity, leading to rapid population resurgence and increased resistance, and mixing multiple chemicals causes formulation instability and environmental harm.
Development of chiral and isomeric sulfonate compounds with specific structural formulas that exhibit high inhibitory activity on pest eggs, formulated into agricultural products with suitable surfactants and application forms.
The sulfonate compounds achieve effective egg inhibition and killing, reducing pest populations and minimizing resistance, while maintaining formulation stability and reducing environmental impact.
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Description
/ 61 “CHIRAL AND ISOMERIC SULFONATE COMPOUND AND ITS APPLICATIONS” FIELD OF TECHNOLOGY
[001] The present invention pertains to the field of agricultural technology, especially to a chiral and isomeric sulfonate pesticide compound, as well as its chiral preparation, separation and applications. TECHNOLOGY FUND
[002] The pesticide market is vast and enormous, with a market capacity close to billions. Typical agricultural pesticides include: Order Orthoptera, such as grasshoppers and tarantulas; Order Hemiptera, such as bed bugs; Order Homoptera, including aphids, leafhoppers and the like; Order Thysanoptera, such as thrips; Order Coleoptera, various species of beetles; Order Lepidoptera, moths and butterflies; Order Hymenoptera, bees and ants; Order Diptera, mosquitoes, flies and the like; Order Acari, various species of red mites, etc.
[003] In current pest control practice, most pesticide products focus on controlling adults, nymphs, or larvae through contact or ingestion, drastically reducing pest populations in crops to protect plants from excessive damage and minimize economic losses after infestation. This method generally effectively controls the pest population in the environment. However, for some short-lived pests (such as red mites and thrips), this method often does not achieve good results.
[004] Taking the red mite as an example, there are many types of acaricides registered, including flubendiamide, abamectin, hexythiazox, fenbutatinoxide, spirodiclofen, etoxazole, liliaceae root extract, Sophora flavescens alkaloids, among dozens of other acaricides of plant, inorganic mineral, or chemical origin. However, most of these acaricides target adults or nymphs, with only a few exhibiting good ovicidal activity. In the field, mites reproduce rapidly, completing a generation every week, resulting in a very serious overlap of generations. Therefore, if only acaricides without ovicidal activity are applied, although adults and nymphs are eliminated, new nymphs quickly hatch from the eggs and rapidly increase the population. Although Petition 870250038759, dated 05 / 13 / 2025, page 135 / 208 / 61, while it is possible to remove subsequently hatched mites through a second application, there are some practical problems. For example, frequent pesticide application leads to a rapid increase in mite resistance. Furthermore, the cost of pesticide application for farmers increases significantly. In the field, to save labor costs, the traditional method of pesticide application tends to mix several substances in a single application, including acaricides, insecticides, fungicides, growth regulators, and foliar nutrients. In field mite control practice, farmers often choose to use ovicidal acaricides in combination to prolong the period of effectiveness. However, among registered acaricides, only etoxazole and spirodiclofen are explicitly used as ovicides, which is relatively rare.The scarcity of varieties and the increase in resistance also increase the demand for new, effective acaricides that can kill both eggs and mites. At the same time, the scarcity of small-molecule acaricides with multiple functions means that farmers often need to mix and apply several types of pesticides, including growth regulators, foliar nutrients, fungicides, and ovicides. Mixing various chemicals with different mechanisms of action and formulations can not only cause antagonism between pesticides but also destroy the stability of the aqueous solution formulation, with precipitation, coagulation, and separation phenomena frequently occurring, which significantly affects pesticide use in the field. Furthermore, the overuse of pesticides can lead to a further increase in target resistance and a negative impact on the environment due to pesticide residues.
[005] Therefore, developing a new type of highly efficient insecticide and ovicide with a novel structure and a unique mechanism of action is key to controlling agricultural pests. CONTENT OF INVENTION
[006] The objective of this invention is to provide a chiral and isomeric sulfonate insecticidal compound, whose absolute configuration is obtained through preparation and separation, and one or more configuration compounds can solve the problems existing in current techniques, achieving a good inhibition effect and Petition 870250038759, dated 05 / 13 / 2025, pages 136 / 208 3 / 61 death of insect eggs.
[007] The inventor, while researching the insecticidal activity of sulfonate compounds, discovered by chance that some of these compounds exhibit low insecticidal activity (insect population reduction rate less than 75%), but display excellent inhibitory activity on pest eggs.
[008] The present invention provides sulfonate compounds with chiral and isomeric structure, according to formula (A), or their mesomers, racemes, stereoisomeric isomers and salts acceptable from a pharmaceutical point of view: THE (THE) Where: Ri and R2 are independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkyl, C2-C10 alkyl carbonyl, C2-C10 alkyl carbonyl and C1-C10 carbonyl; R3, R3', R4 and Rf are independently selected from hydrogen and C1-C5 alkyl, C1-C5 alkenyl; or, R3, R3', R4, R4' and the C to which they are attached form a five-membered cycloalkanyl heterocyclic group; Rs is selected from either halogen or substituted or unsubstituted C1-C10 alkyl.
[009] Additionally, the structure of the compound is selected from one of the following: go Petition 870250038759, dated 05 / 13 / 2025, pp. 137 / 208 4 / 61
[010] In formula (A) and in formulas I to VI, additionally, the C1C5 alkyne group is methyl or ethyl.,
[011] In formula (A) and in formulas I to VI, additionally, the said alkenyl group from C1 to C5 is selected from vinyl. In formula (A) and in formulas I to VI, additionally, the five-membered cycloalkanyl heterocyclic is selected from the
[012] Additionally, R5 is selected from fluorinated ethyl, brominated ethyl, golden ethyl, 2,2-difluorinated ethyl and 2,2-dichlorinated ethyl; Ri and R2 are selected independently from H, F, Cl, Br.
[013] Additionally, R5 is -CH2CH2F; Ri and R2 are Cl.
[014] Additionally, the compound is selected from among the following compounds: Petition 870250038759, dated 05 / 13 / 2025, pp. 138 / 208 5 / 61 7' Petition 870250038759, dated 05 / 13 / 2025, pages 139 / 208 6 / 61
[015] Except where already specified, the term substituted refers to the possibility of the mentioned group being replaced by one or more additional groups, each additional group being independently selected from alkyl, cycloalkyl, aryl, carboxyl, heteroaryl, heterocycloalkyl, hydroxyl, alkoyl, altyl, aryloyl, O=, guanidine, cyanyl, nitrile, acyl, halogen, haloalkyl, amino, among others.
[016] The compounds of the present invention can have their structure confirmed by conventional methods known to a person skilled in the art. If the invention involves the absolute configuration of a compound, this absolute configuration can be confirmed by conventional techniques in the field. According to the literature (Absolute configuration of glycosyl sulfoxides, Tetrahedron: Asymmetry, Volume 21, Issue 15, 2010, Pages 1830-1832), if a group and the lone pair of electrons of sulfur are on the same side, the group is shielded, the chemical shift decreases and moves to the high field. If a group is on the same side as the oxygen atom, the group is unshielded, the chemical shift increases and moves to the low field. The absolute configuration is obtained by comparing and analyzing the hydrogen spectrum of chirally separating compounds and by measuring the optical rotation.
[017] The compound numbers above are only to facilitate the subsequent explanation.
[018] The present invention provides a method for controlling and / or killing pest eggs and / or fungicide, using the above compounds applied to pest eggs and / or fungi.
[019] Additionally, for the control and / or killing of pest eggs and / or fungicide, the compound is selected from the following compounds, including mixtures of various configurations: Petition 870250038759, dated 05 / 13 / 2025, pp. 140 / 208 7 / 61 19' 19'-(R,R)
[020] The intermediate compounds of the present invention can be prepared by various synthesis methods known to a person skilled in the art, including the specific implementation modes enumerated in this text, their combinations with other chemical synthesis methods and equivalent substitution modes known to a person skilled in the art, wherein the preferred implementation modes include, but are not limited to, the examples of the present invention.
[021] The chemical reactions of the specific embodiments of the present invention are carried out in a suitable solvent, which must be compatible with the chemical transformations of the invention and with the reagents and materials required. To obtain the compounds of the present invention, it is sometimes necessary for a person skilled in the art to make modifications or selections in the synthesis steps or in the reaction process, based on existing embodiments.
[022] In the present application, the term pest refers to an organism that Petition 870250038759, dated 05 / 13 / 2025, page 141 / 208 / 61 adversely affects the host (e.g., plants or animals such as mammals) through parasitism, damage, attack, competition for nutrients, or infection.
[023] In the absence of specific limitation, pests include arthropods (including insects and arachnids), and encompass sucking pests and biting pests (e.g., bed bugs, mites, ticks, ants, lice, cockroaches, thrips, etc.).
[024] In the absence of specific limitation, pest eggs are produced by insects of the orders Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Arachnoidea, arachnids of the families Tetranychidae, Tarsonemidae, Eriophyidae, Tenuipalpidae, Phytoseiidae, Ascidae or Prostigmata; and fungi include fungi and bacteria.
[025] Thysanoptera (Order Thysanoptera), belonging to the class Insecta, is commonly known as thrips. They are small insects with elongated, thin bodies, generally yellowish-brown or black in color. They have well-developed eyes and a piercing-sucking mouthparts that are asymmetrical. The wings are narrow and have few or no veins, with elongated edges covered in long hairs. Some types may be winged or wingless, and there are also forms with wings reduced to vestiges. They do not have tails. They feed mainly on plant sap, affecting cereal, cotton, and tobacco crops, among others. Some species can transmit plant viruses and are considered pests. Thrips are divided into two suborders: Terebrantia and Tubulifera. The suborder Thrips (sawtails) includes: Aeolothripoidea (family Aeolothripidae, family Orothripidae, family Melanthripidae, family Dactuliothripidae, family Franklinothripidae).Merothripoidea (family Merothripidae), Thripoidea (family Heterothripidae, family Hemithripidae, family Ceratothripidae, family Panchaetothripidae, family Thripidae); among them, the Thripidae family is the largest and most important of the suborder, with 33 known genera and about 200 species, such as: Frankliniella intonsa (flower thrips), Thrips tabaci Lindeman (tobacco thrips), Taeniothrips distalis Karny (soybean thrips), Stenchaetothrips biformis (rice thrips), Thrips hawaiiensis Morgan (Hawaiian thrips), Thrips palmi Karny (palm thrips), Frankliniella occidentalis (western flower thrips), Thrips japonicus Bagnall (Japanese thrips), Thrips serratus Kobus (saw thrips, Petition 870250038759, dated 05 / 13 / 2025, page 142 / 208 / 61 sugarcane), Frankliniella tenuicornis Uzel (wheat thrips), Scirtothrips dorsalis Hood (tea thrips), Heliothrips haemorrhoidalis Bouche (greenhouse thrips), Scolothrips sexmaculatus Pergande (six-spot thrips), among other species common in China. Tubulifera includes: Phlaeothripoidea (Pypothripidae, Ecacanthothripidae, Eupatithripidae, Phlaeothripidae, Chirothripoididae, Hystricothripidae, Idolothripidae, Megathripidae) and Urothripoidea (Urothripidae). The families listed in parentheses after each superfamily are subfamilies belonging to that superfamily. Similarly, all subsequent references to superfamilies will be expressed using this method.
[026] Hemiptera (Order Hemiptera), belonging to the class Insecta, has a slightly flattened and rigid body; the mouthparts are of the piercing-sucking type; the antennae are filiform or clavate; there are two simple eyes or none; the thoracic scutes are well developed, and the scutellum is often triangular; the forewings are hemelytra, and the hindwings are membranous, with some species having reduced or absent wings; most species possess scent glands; the tarsi often have claws at the end, with a claw pad below them; the abdomen has 9-11 segments, usually 10; there are no tails. The name Hemiptera derives from the fact that its forewings are hemelytra.Hemiptera is divided into Auchenorrhyncha and Sternorrhyncha; Auchenorrhyncha includes Cicadiodea(Cicadidae, Membracidae, Machearotidae, Cercopidae, Cicadellidae) and Fulgoroidea(Tettigometridae, Delphacidae, Fulgoridae, Eurybrachydidae, Cixiidae, Meenoplidae, Dictyopharidae, Achilidae, Tropiduchidae, Derbidae, Lophopidae, Issidae, Flatidae, Ricaniidae); Sternorrhyncha includes Psylloidea(Psyllidae), Aleyrodoidea(Aleyrodidae), Aphidoidea(Adelgidae, Phylloxeridae, Pemphigidae, Aphididae) and Coccoidea(Margarodidae, Ortheziidae, Kerridae, Kermidae, Dactylopiidae, Pseudococcidae, Asterolecaniidae, Coccidae and Diaspididae).
[027] Lepidoptera (Order Lepidoptera), belonging to the class Insecta, has an extremely wide distribution, with tropical species being the most abundant. The vast majority of larvae of these species feed on cultivated plants, with the larger ones frequently consuming all the leaves or boring into trunks and branches. The smaller ones, on the other hand, usually curl leaves, join Petition 870250038759, dated 05 / 13 / 2025, p. 143 / 208 / 61 leaves, form capsules, weave webs or penetrate plant tissues to feed. Adults generally feed on flower nectar as a supplementary source of nutrition, or have reduced mouthparts and no longer feed. Lepidoptera includes Zeugloptera (Micropterygidae), Monotrysia (Eriocraniidea, Hepialoidea, Stigmelloidea and Incurvarioidea) and Ditrhysia (Tinaeoidea, Cossoidea, Psychoidea, Castnioidea, Tortricoidea, Pyraloidea, Bombycoidea, Calliduloidea, Geometroidea, Sphingoidea, Noctuoidea, Hesperioidea and Papilionoidea).
[028] Coleoptera is the order with the largest number of species and the widest distribution within the class Insecta, and even in the animal kingdom. It is divided into Adephaga, Polyphaga, Rhynchophora; Adephaga includes: Caraboidea (Cicindelidae, Carabidae, Amphizoidae, Omophronidae, Hygrobiidae, Haliplidae and Dytiscidae), Gyrinoidea (Gyrinidae), Paussoidea (Paussidae), Cupesoidea (Cupesidae), Rhysodoidea(Rhysodoidae); Polyphaga includes: Hydrophiloidea (Hydophilidae), Staphylinoidea (Silphidae, Leiodidae, Clambidae, Scydmaenidae, Orthoperidae, Phaenocephalidae, Discolomidae and Platypsillidae), Cantharoidea (Lycidae, Lampyridae, Cantharidae, Drilidae, Malachiidae, Phloeophilidae, Prionoceridae and Dasytidae), Lymexyloidea (Lymexylidae and Atractoceridae), Elateroidea Rhipiceridae, Cebrionidae, Elateridae, Eucnemidae and Throscidae), Dryopoidea (Psephenidae, Dryopidae, Helmidae, Georyssidae and Heteroceridae), Dascilloidea (Dascillidae), Tenebrionoidea (Alleculidae and Tenebrionidae), Ptinidae (Lyctidae, Bostrychidae, Anobiidae and Ptinidae), Scarabaeoidea (Scarabaeidae, Aegialiidae, Aphodiidae, Ochodaeidae, Geotrupidae, Trogidae, Melolonthidae, Rutelidae, Dynastidae, Cetoniidae, Trichiidae and Passalidae), Cerambycoidea (Prionidae, Cerambycidae, Lamiidae and Sagridae), Brentoidea (Brentidae), Curculionoidea (Anthribidae, Aglycyderidae, Proterhiniidae, Cyladidae, Curculionidae);Rhynchophora includes: Curculionoidea (Anthribidae, Aglycyderidae, Proterhiniidae, Cyladidae and Curculionidae). Common insects (commonly known): Coccinella transversalis, Cerambycidae, Coccinellidae, Lampyridae, Scarabaeidae, Mylabris, Dynastinae, Buprestidae, Meloidae, Scarabaeidae, Lucanidae, Elateridae, Hydrometidae, Sitophilus.;
[029] The mites referred to in this application mainly include agricultural pest mites, most of which belong to the order Achacinida of the following Petition 870250038759, dated 05 / 13 / 2025, pp. 144 / 208 / 61 families: Tetranychidae, Tenuipalpidae, Eriophyidae, Tarsonemidae, Pyemotidae, Penthaleidae and Cheyetidae.
[030] Tetranychidae includes Oligonychus(Oligonychus baipisongis, Oligonychus karamatus and Oligonychus rubicundus), Eotetranychus(Eotetranychus albus, Eotetranychus bailae and Eotetranychus camelliae), Tetranychus(Tetranychus neocaledonicus, Tetranychus phaselus, Tetranychus urticae and Tetranychus cinnabarinus), Schizotetranychus(Schizotetranychus baltazarae, Schizotetranychus bambusae and Schizotetranychus elongatus), Mixonychus(Mixonychus (Bakerina) aestiva, Mixonychus (Mixonychus) ganjuis and Mixonychus (Bakerina) murrayae), Panonychus(Panonychus citri, Panonychus caglei, Panonychus ulmi), Allonychus(Allonychus bambusae, Allonychus wuyinicus), Stigmaeopsis(Stigmaeopsis celarius, Stigmaeopsis nanjingensis), Mononychellus(Mononychellus georgicus), Acanthonychus (Acanthonychus jiangfengensis), Acanthonychus jiangfengensis (Amphitetranychus viennensis), Sonotetranychus (Sonotetranychus neosalix), Xinella (Xinella huangshanensis), Yunonychus (Yunonychus daliensis), Neotetranychus (Neotetranychus lek),Eurytetranychus (Eurytetranychus glycyrrhizae, Eurytetranychus wuyishanensis), Aponychus (Aponychus aequilibris, Aponychus corpuzae), Eutetranychus (Eutetranychus orientalis, Eutetranychus xianensis), Stylophoronychus (Stylophoronychus baghensis), Eurytetranychoides (Eurytetranychoides japonicus), Tenuipalpoides (Tenuipalpoides hastata and Tenuipalpoides zizyphus), Bryobia (Bryobia borealis and Bryobia exserta), Sinobryobia (Sinobryobia chinensis), Petrobia (Petrobia (Petrobia) xinjiangensis, Petrobia (Tetranychina) zachvatkini), Tetranycopsis (Tetranycopsis hystriciformis and Tetranycopsis spiraeae), Aplonobia (Aplonobia alkalisalinae), Mesobryobia (Mesobryobia terpoghossiani), Dolichonobia (Dolichonobia altaensis).
[031] Additionally, the pests mentioned are selected from Frankliniella intonsa, Thrips tabaci Lindeman, Taeniothrips distalis Karn, Stenchaeotothrips biformis, Thrips hawaiiensis Morgan, Thrips palmi Karny, Frankliniella occidentalis, Thrips japonicus Bagnall, Thrips serratus Kobus, Frankliniella tenuicornis Uzel, Scirtothrips dorsalis Hood, Heliothrips haemorrhoidalis Bouche, Scirtothrips dorsalis Hood, Scolothrips sexmaculatus Pergande, Cnaphalocrocis Petition 870250038759, dated 13 / 05 / 2025, p. 145 / 208 / 61 medinalis, Spodoptera exigua, Spodoptera litura, Carposina sasakii, Helicoverpa armigera, Plutella xylostella, Diaphania indica, Maruca testulalis Geyer, Bemisia tabaci Gennadius, Trialeurodes vaporariorum, Aleurocanthus spiniferus, Dialeurodes citri Ashm, Bemisia myricae Kuwana, Aleurocybotus indicus, Aleurodicus dispersus, Oligonychus baipisongis, Oligonychus karamatus, Oligonychus rubicundus, Cerambycidae, Coccinellidae, Lampyridae, Scarabaeidae, Mylabris phalerata, Allomyrina dichotoma, Buprestidae, Melyridae, Scarabaeidae, Lucanidae, Elateridae, Dytiscidae, Sitophilus oryzae, Harmonia axyridis, Eotetranychus albus, Eotetranychus bailae, Eotetranychus camelliae, Tetranychus neocaledonicus, Tetranychus phaselus, Tetranychus urticae, Tetranychus cinnabarinus, Schizotetranychus baltazarae, Schizotetranychus bambusae, Schizotetranychus elongatus, Mixonychus (Bakerina) aestiva, Mixonychus (Mixonychus) ganjuis, Panonychus citri,Panonychus caglei, Allonychus bamboosae, Allonychus wuyinicus, Stigmaeopsis celarius, Mononychellus georgicus, Acanthonychus jiangfengensis, Amphitetranychus viennensis.,
[032] Among them, the mentioned fungus is a fungus.
[033] In a specific example of the invention, the fungus is the rice blast disease fungus. The rice blast disease fungus can cause rice blast, which damages the seedling, leaves, panicle, node, etc.
[034] The term control mentioned in the invention includes, but is not limited to, the arbitrary death of insect eggs, hatching control, inhibition / interference with insect egg activity, and hatching prevention, etc. Hatching prevention refers to preventing or delaying the birth of larvae from eggs.
[035] The term death mentioned in the invention refers to the permanent loss of the ability of insect eggs to grow and hatch.
[036] The term fungicide mentioned in the invention refers to the direct killing or inhibition of the growth of plant pathogens, including fungi and bacteria. The fungicide includes protective fungicide and systemic fungicide. The protective fungicide acts directly upon contact with the pathogen on the external surface or on the surface of the plant, killing or inhibiting the pathogen so that it cannot enter the plant, thus protecting the plant against the threat of the pathogen. The systemic fungicide can Petition 870250038759, dated 05 / 13 / 2025, page 146 / 208 / 61 to be absorbed by the plant and carried to the site of fungal infection to destroy the fungi.
[037] In the invention, when used, the sulfonate ester compound is formulated into an agricultural product for use, and the agricultural product also includes one or more dispersants, wetting agents, binding agents, surface agents, stabilizers, solvents, etc.
[038] Suitable surface-active agents may be selected by technicians according to the needs of use. Examples of surfactants that may be used in some embodiments of the present application include, among others, ethoxylated castor oil, sodium lauryl sulfate, saponin, 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 in question is a non-ionic surfactant. In some embodiments, the surfactant in question is an ionic surfactant. The selection of a suitable surfactant depends on the relevant application and conditions of use, and suitable surfactants are known to those skilled in the art.
[039] In the present invention, dosage forms of said compositions include, but are not limited to, emulsifiable oil, soluble powders, soluble granules, soluble liquids, dispersible liquids, aqueous emulsions, microemulsions, microencapsulated suspensions, liquids for seed treatment and aerosols, etc.
[040] Emulsifiable oil is a type of pesticide formulation that consists of a higher concentration of the active ingredient dissolved in a solvent, plus an emulsifier in the liquid. It is usually diluted into a stable emulsion with large amounts of water and then dispersed with a sprayer; low-volume to ultra-low-volume spraying is also possible. It can be used directly or diluted in water and sprayed.
[041] Wettable powder is a very fine dry agent obtained by mixing and grinding the original drug product, filler, surfactant and other additives. Petition 870250038759, dated 05 / 13 / 2025, pp. 147 / 208 / 61
[042] Concentrated suspensions refer to formulations in which the solid active ingredient is uniformly dispersed in water in the form of particles smaller than 4 micrometers. The international code for this type of formulation is SC. These particles are fine, generally with a diameter between 0.1 and 3 micrometers, and have a high suspension rate. Concentrated suspensions are divided into two types: aqueous suspensions and oil suspensions. An aqueous suspension uses water as the suspension medium, while an oil suspension uses oil as the suspension medium without water. Commonly used oils are vegetable oils, such as corn oil and canola oil. The suspension can be completely free of organic solvents, making it a good formulation for processing original solid medication. Suspensions are mixtures of solid and liquid powders suspended in water that need to be well shaken before use, then diluted with water and sprayed.Suspensions are easy to transport and dilute, can be sprayed evenly, and have good adhesion and retention properties.
[043] The powder is the original powder or the powder prepared with the addition of certain diluents. It can be sprayed directly with a simple duster, which is highly efficient, with low adherence to the crop, little residue and less prone to damage caused by medications.
[044] Granules, or granulated products, are a solid dosage form obtained by mixing and granulating the original drug with a carrier, adhesive, dispersant, wetting agent, stabilizer, and other additives. Their performance requirements are primarily fineness, uniformity, storage stability, hardness, and disintegration. Granules are the solid form with the largest particle size, with diameters between 300 and 1700 μm, and have the advantages of being easy to use, having low external dispersion, and long-lasting effectiveness.
[045] The aqueous solvent is a solvent of the active ingredient, where the pharmaceutical agent is uniformly dispersed in water in the form of ions or molecules, the concentration of the pharmaceutical agent depends on the solubility of the active ingredient in water, generally being its maximum solubility, at the time of use, it is diluted with water.
[046] In the invention, the sulfonate ester compound can be combined with the Petition 870250038759, dated 05 / 13 / 2025, page 148 / 208 / 61 most insecticides, acaricides, fungicides and other agricultural formulations available on the market for use, obtaining a synergistic effect.
[047] Furthermore, when using the sulfonate ester compound for pest egg control and / or killing and / or fungicide, the concentration of the sulfonate ester compound should not be less than 0.1 ppm. Moreover, the concentration of the sulfonate ester compound should not be less than 1 ppm.
[048] Among them, the application concentration of the sulfonate ester compound is 0.1 to 10000 ppm, it can also be 0.1 to 500 ppm, 0.1 to 200 ppm, 0.1 to 100 ppm, 0.1 to 50 ppm, 1 to 500 ppm, 1 to 200 ppm, 1 to 100 ppm, 1 to 50 ppm, 1 to 10 ppm, 1 to 5 ppm, 2 to 200 ppm, 2 to 100 ppm, 2 to 50 ppm, 2 to 10 ppm, 3 to 200 ppm, 3 to 100 ppm, 3 to 50 ppm, 3 to 10 ppm, 4 to 200 ppm, 4 to 100 ppm, 4 to 50 ppm, 4 to 10 ppm, 10 to 1000 ppm. Specifically, it is possible to choose, but is not limited to: 0.1 ppm, 0.2 ppm, 0.3 ppm, 0.4 ppm, 0.5 ppm, 0.6 ppm, 0.7 ppm, 0.8 ppm, 0.9 ppm, 1 ppm, 1.1 ppm, 1.2 ppm, 1.3 ppm, 1.4 ppm, 1.5 ppm, 1.6 ppm, 1.7 ppm, 1.8 ppm, 1.9 ppm, 2.0 ppm, 2.5 ppm, 3 ppm, 3.5 ppm, 4 ppm, 4.5 ppm, 5 ppm, 5.5 ppm, 6 ppm, 6.5 ppm, 7 ppm, 7.5 ppm, 8 ppm, 8.5 ppm, 9 ppm, 9.5 ppm, 10 ppm, 11 ppm, 12 ppm, 13 ppm, 14 ppm, 15 ppm, 20 ppm, 25 ppm, 30 ppm, 35 ppm, 40 ppm, 45 ppm, 50 ppm, 100 ppm, etc.
[049] Furthermore, when the sulfonate ester compound is used for the control and / or killing of insect eggs, the application concentration of the sulfonate ester compound is 0.1 to 500 ppm; when the sulfonate ester compound is used as a fungicide, the application concentration of the sulfonate ester compound is 10 to 1000 ppm.
[050] The present invention also provides a pesticide composition of formula (I) as the active substance.
[051] In the present invention, the said pesticide compound includes dispersants, wetting agents, binding agents, surface-active agents, stabilizers, solvents, etc.
[052] In the present invention, the said pesticide compound may also be combined with other products, including, but not limited to, one or more insecticides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers Petition 870250038759, dated 05 / 13 / 2025, page 149 / 208 / 61 or compounds that have equivalent functions but have not yet been commercialized. This may generate additional advantages and effects. For example, other insecticides may include flupyradifurone, cypermethrin, acetamiprid, teflubenzuron, thiamethoxam, spirotetramat, spiromesifen, clothianidin, chlorantraniliprole, lambdacyhalothrin, flubendiamide, cyazypyr, deltamethrin, flupyradifurone, thiacloprid, sulfoxaflor, abamectin, chlorantraniliprole, bifenthrin, cyantraniliprole, flubendiamide, flufenoxuron, emamectin benzoate, trifloxysulfuron, sulfoxaflor, malathion, indoxacarb, dinotefuran, disulfoton, fipronil, permethrin, hexaflumuron, fluacrypyrim, among others.
[053] In one embodiment of the present application, the said pesticide compound includes a mixture of a Zingiber officinale rhizome extract and a Kaempferia rhizome extract, the Zingiber officinale rhizome extract: Kaempferia rhizome extract = 7:3, wherein the ginger rhizome extract is Zingiber officinale rhizome extracted with ethanol: ethyl acetate = 1~4:1; said Kaempferia rhizome extract is the volatile oil of Kaempferia rhizome. The mixing ratio between the ginger and galangal combination and the compound of formula (A) can be (200-500):(0.1-1). Experimental studies have shown that the combined use of these two components presents a synergistic effect, which allows for a reduction in the concentration of the active components.
[054] In this application, the terms include or comprise are interpreted in their open sense, that is, they mean that the presence of the mentioned characteristics, elements, steps or components is specified, but does not exclude the existence or addition of other characteristics, elements, steps or components.
[055] In some embodiments, the compounds mentioned above are applied outdoors or applied to plants, agricultural areas and / or buildings, both indoors and outdoors. In some embodiments, the compounds mentioned above are applied to surfaces inside houses, dwellings or buildings. In some embodiments, the compounds mentioned above are applied to mattresses, sheets, fabrics, suitcases / briefcases, carpets, painted or unpainted hard surfaces, wood, floors, Petition 870250038759, dated 05 / 13 / 2025, pages 150 / 208 / 61 furniture and / or buildings.
[056] In some implementation forms, the compounds mentioned above are formulated in an application form suitable for the specific application, which include, but are not limited to, liquids, emulsions, solids, waxes, powders, fumigants, aqueous suspensions, oily dispersions, pastes, powders, dust, emulsifiable concentrates, aerosols, wood fillers, varnishes, wood treatments or furniture oils, detergents, drywall mixtures, incense candles, joint filler compounds, crack and crevice fillers, sealants, and treatments for mattresses and mattress covers. Suitable application forms may be chosen and formulated by field technicians using methods known in the field. In different usage scenarios, the compounds mentioned above may have various application forms, and may be used directly, diluted, or concentrated.Furthermore, they can also be used as: protective oil for wood or furniture, laundry detergent, gel or paste applied to the target area, oily emulsion, part of a mixture for drywall dusting materials, filler for cracks or fissures or other sealing materials, foam, part of joint filler, incense or candle mist, aerosol or insecticide spray, treatment for mattresses or mattress covers. In some cases, these mixtures can be used in domestic or commercial environments, in dispersed form, to combat pest and fungal eggs. Additionally, they can also be used in agricultural or outdoor environments for pest and fungal egg control.
[057] The solvent used in the above product or compound may also be chosen from water, ketone, alcohol, aldehyde, ether, ester or carboxylic acid, and may include non-aromatic ketone, non-aromatic alcohol, non-aromatic aldehyde, non-aromatic ester, non-aromatic carboxylic acid, aromatic alcohol, aryl-alkyl alcohol, aromatic aldehyde, aryl-alkyl ketone, aryl-aromatic ketone, aromatic carboxylic acid, aryl-alkyl ester, aryl-aromatic ester, aryl-alkyl ether, aryl-aromatic ether and / or combinations thereof.
[058] In some embodiments, the solvent may include ethanol, isopropanol, benzyl, acetone, phenyl acetone, water, citric acid, lactic acid, Petition 870250038759, dated 05 / 13 / 2025, p. 151 / 208 / 61 glycerol, castor oil, benzoic acid, carbonate, ethoxylated alcohol, ethoxylated amide, glycerides, butanol, 1-propanol, hexanol, other alcohols, dimethyl ether, polyethylene glycol, among others.
[059] The benefits of the invention are: the invention provides the application of chiral and isomeric sulfonate ester compounds in the inhibition of insect eggs; these chiral and isomeric sulfonate ester compounds have a strong inhibitory effect on insect eggs, especially on eggs of thripid pests, mites and whiteflies; these compounds can be used as insecticides or ovicides, have a high research value in pesticides and have a broad application prospect in the field of pesticide science. DESCRIPTION OF THE APPENDIX
[060] Figure 1 is the chromatogram of the separation of the mixture of compounds 1 and 1' from column IG.
[061] Figure 2 is the chromatogram of the separation of the R enantiomer of compounds 1 and 1' from column IG.
[062] Figure 3 is the chromatogram of the S enantiomer separation of compounds 1 and 1' from the IG column.
[063] Figure 4 is the chromatogram of the first peak separated from the R enantiomer on the IG column.
[064] Figure 5 is the chromatogram of the second peak separated from the R enantiomer on the IG column.
[065] Figure 6 is the chromatogram of the third peak separated from the R enantiomer on the IG column.
[066] Figure 7 is the chromatogram of the separated fourth peak of the R enantiomer on the IG column.
[067] Figure 8 is the chromatogram of the first peak separated from the S enantiomer on the IG column.
[068] Figure 9 is the chromatogram of the second peak separated from the S enantiomer on the IG column.
[069] Figure 10 is the chromatogram of the third peak separated from the enantiomer Petition 870250038759, dated 05 / 13 / 2025, page 152 / 208 / 61 S in the IG column
[070] Figure 11 is the chromatographic peak of the first separated peak of the S enantiomer of compounds 1 and 1' on the IG column, using an AS column for separation. SPECIFIC IMPLEMENTATION
[071] To make the objectives, technical solutions and advantages of the invention clearer and more understandable, the following examples are provided to illustrate the invention in more detail. It should be understood that the specific examples described here serve only to explain the invention and should not be considered as limitations of the invention. Furthermore, unless specifically indicated, all reagents, raw materials and other test materials used in the examples below can be commercially acquired or synthesized, grown or cultivated according to the methods described in this text or known methods. For experimental conditions not listed, they are also readily obtainable by skilled professionals.
[072] When a numeric range is provided, it is understood that all intermediate values (up to one-tenth of the unit of the lower limit, unless the context explicitly indicates otherwise) and any other values or intervals specified within that range are included in the implementation forms of this application. The upper and lower limits of these smaller ranges may be defined independently to create smaller numeric intervals, and it should be understood that these smaller intervals are included in the implementation forms of this application, subject to any limits explicitly excluded within the specified range.
[073] Unless otherwise specified, all technical and scientific terms used in this document have the same meaning as the common skill terms in the field to which the application belongs. Methods and materials similar or equivalent to those described in this text may also be used in the practice or testing of the implementation methods of this application. Petition 870250038759, dated 05 / 13 / 2025, pp. 153 / 208 20 / 61 Example 1: Synthesis of compounds Sl and Sl' S-1 ST Step 1:
[074] Add phenol-2,4-dichloride (500 mg, 3.1 mmol), R-propanol epoxy (356 mg, 6.1 mmol), DMF (12 mL) and cesium carbonate (4.0 g, 12.3 mmol) to a reaction flask, heat to 100 degrees Celsius and reflux. Monitor the reaction by TLC. After the reaction is complete, concentrate the mixture and dissolve the residue in water (10 mL) and ethyl acetate (50 mL). Separate the phases, extract the aqueous phase with ethyl acetate (50 mL x 2), combine the organic phases, wash with saturated saline water, dry with anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain compounds iii-1 and iii-1' (total of 511 mg, colorless and transparent liquid). Step 2: THE o+Cl Cl iv-1
[075] Add dichloro thiosulfate (415 mg, 3.5 mmol) to a reaction flask, dissolve in 15 mL of dichloromethane and stir in an ice bath at 0°C. Slowly add the mixture of compounds iii-1 and iii-1' (511 mg, 2.3 mmol). After the addition, allow the reaction to stand at room temperature for 10 hours, monitoring the reaction by Petition 870250038759, dated 05 / 13 / 2025, pages 154 / 208 21 / 61 TLC until completion, concentrate the reaction solution under vacuum to obtain a yellowish oil, which is the crude product of compounds v-1 and ν-Γ, for further use. Step 3: the v-1' S-1'
[076] Add compound vi-1 (224 mg, 3.5 mmol) to a reaction flask, add triethylamine (349 mg, 3.5 mmol) and stir in an ice bath at 0°C. Slowly add the mixture of compounds v-1 and v-1' (690 mg, 2.3 mmol). After addition, allow the reaction to stand at room temperature for 6 hours, monitor the reaction by TLC until completion, add 100 mL of water to the reaction solution, extract with dichloromethane (30 mL x 3), wash with saturated saline water, collect the organic phase, dry with anhydrous sodium sulfate, concentrate under vacuum and purify by column chromatography to obtain the mixture of compounds S-1 and S-1' (501 mg, colorless and transparent liquid). Example 2: Synthesis of compounds Rl and R-Γ R-1 R-Γ
[077] Replace R-propanol epoxy in Step 1 of Example 1 with S-propanol epoxy and follow the synthesis method of Example 1 to obtain the mixture of compounds R1 and R1' (515 mg, colorless and transparent liquid). Example 3: Synthesis of compounds S-19 and S-19' Petition 870250038759, dated 05 / 13 / 2025, pp. 155 / 208 22 / 61 iii-19'
[078] Following step 1 of synthesis example 1, replacing the R-propanol epoxide with R1,2-butanol epoxide, the mixture of target compounds iii-19 and iii19' is obtained.
[079] Step 2: Identical to Step 2 of Example 1.
[080] Step 3: Identical to Step 3 of Example 1.
[081] After synthesis, the target compound S-19, S-19' (523 mg, colorless and transparent liquid) was obtained. Example 4: Synthesis of compounds R-19 and R-19' R-19
[082] Replace R-propanol epoxy in Step 1 of Example 1 with Sl,2-butanol epoxide and follow the synthesis method of Example 1 to obtain the mixture of compounds R-19 and R-19' (507 mg, colorless and transparent liquid). Example 5: Chiral separation of compounds S1, S-1', R1, R-Γ, 10,10', S19, S-19', R-19 and R-19'
[083] 1. Experimental Method Petition 870250038759, dated 05 / 13 / 2025, pp. 156 / 208 / 61
[084] 1.1 Separation of chemical compounds
[085] Initially, it is believed that the sulfonate ester compounds 1-9, Γ-9' 1924 and 19'-24' have two chiral centers. Using chiral raw materials for synthesis and then performing separation, Equipment: Shimadzu high-pressure preparation liquid chromatography, model LC20AR; Chiral column: CHIRALPAK® IG normal phase chiral column, CHIRALPAK® AS normal phase chiral column, 4.6 mm ID x 250 mm, diameter: 5 µm. Mobile phase: Hexane:isopropanol = 95:5.
[086] The mixture of compounds 1 and 1' (S configuration) is separated into 3 components using the IG column, and the mixture of compounds 1 and 1' (R configuration) is separated into 4 components using the IG column. By separating the 7 components obtained using the AS column, it is found that the first peak of the S configuration of compounds 1 and 1' contains 2 components. After a further separation, a total of 8 components are obtained.
[087] In the synthesis of compound 1, the first reaction produces two products, iii-1 and iii-1', due to the difference in the ring-opening position, which leads to the difference in the position of the methyl group. These two products can be separated using chiral preparation chromatography. Equipment: Shimadzu high-pressure preparation liquid chromatograph, model LC20AR; Chiral column: CHIRALPAK® IG normal-phase chiral column, 4.6 mm ID x 250 mm, diameter: 5 µm. Mobile phase: Hexane:isopropanol = 90:10. (Separations of iii-4, iii-4' and other compounds use identical conditions)
[088] 1.2 Determination of the absolute configuration of compounds
[089] 1.2.1 Proton spectrum test of the compound
[090] 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 a group and the lone pair of electrons of sulfur are on the same side, the group is shielded, the chemical shift decreases and moves towards the high field. If a group is on the same side as the oxygen atom, the group is unshielded, the chemical shift increases and moves towards the low field. According to this result, the analysis of nuclear magnetic spectroscopy (NMR) data from the separated compounds allows us to infer their configuration. Petition 870250038759, dated 05 / 13 / 2025, pages 157 / 208 24 / 61 absolute.
[091] 1-(R,R):XH NMR (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,90 (td, J = 6,6, 4,1 Hz, 1H), 4,62 (dd, J = 5,1, 3,1 Hz, 1H), 4,53 - 4,45 (m, 1H), 4,37 - 4,10 (m, 2H), 3,98 (qd, J = 10,0, 5,4 Hz, 2H), 1,39 (d, J = 6,5 Hz, 3H) ppm.
[092] 1-(R,S):XH NMR (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,6 Hz, 1H), 6,85 (d, J = 8,8 Hz, 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, 4,1 Hz, 1H), 1,32 (d, J = 6,3 Hz, 3H) ppm.
[093] 1-(S,R):XH NMR (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,6 Hz, 1H), 6,85 (d, J = 8,8 Hz, 1H), 4,64 - 4,55 (m, 1H), 4,55 - 4,38 (m, 2H), 4,24 4,11 (m, 3H), 4,04 (dd, J = 11,2, 4,1 Hz, 1H), 1,32 (d, J = 6,3 Hz, 3H) ppm.
[094] 1-(S,S):XH NMR (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,90 (td, J = 6,6, 4,1 Hz, 1H), 4,62 (dd, J = 5,1, 3,1 Hz, 1H), 4,56 - 4,45 (m, 1H), 4,37 - 4,10 (m, 2H), 3,98 (qd, J = 10,0, 5,4 Hz, 2H), 1,39 (d, J = 6,5 Hz, 3H) ppm. Petição 870250038759, de 13 / 05 / 2025, pág. 158 / 208 / 61
[095] 1’-(S,R) : 1H NMR (400 MHz, CDCI3) δ 7,30 (d, J = 2,5 Hz, 1H), 7.11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,88 (pd, J = 6,4, 4,4 Hz, 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, 6,3 Hz, 1H), 3,93 (dd, J = 10,0, 4,3 Hz, 1H), 1,43 (d, J = 6,5 Hz, 3H) ppm.
[096] 1-(S,S): 1H NMR (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,90 (td, J = 6,6, 4,1 Hz, 1H), 4,62 (dd, J = 5,1, 3,1 Hz, 1H), 4,53 - 4,45 (m, 1H), 4,37 - 4,10 (m, 2H), 3,98 (qd, J = 10,0, 5,4 Hz, 2H), 1,39 (d, J = 6,5 Hz, 3H) ppm.
[097] 1-(R,R): 1H RMN (400 MHz, CDCI3) δ 7,31 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,90 (td, J = 6,6, 4,1 Hz, 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, 5,4 Hz, 2H), 1,39 (d, J = 6,5 Hz, 3H) ppm.
[098] 1’-(R,S) : 1H NMR (400 MHz, CDCI3) δ 7,30 (d, J = 2,5 Hz, 1H), 7,11 (dd, J = 8,8, 2,5 Hz, 1H), 6,76 (d, J = 8,8 Hz, 1H), 4,88 (td, J = 6,4, 4,3 Hz, 1H), 4,65 - 4,57 (m, 1H), 4,50 (td, J = 3,9, 3,3, 1,5 Hz, 1H), 4,32 - 4,12 (m, 2H), 4,01 (dd, J = 10,0, 6,3 Hz, 1H), 3,93 (dd, J = 10,0, 4,3 Hz, 1H), 1,43 (s, 3H) ppm.
[099] S-10: 1H NMR (400 MHz, CDCI3) δ 7.44 (d, J = 1.4 Hz, 1H), 7.27 - 7.25 (m, 1H), 7.10 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 2.9 Hz, 1H), 4.75 (t, J = 2.9 Hz, 1H), 4.42 (s, 2H), 3.97 (t, J = 2.9 Hz, 1H), 3.90 (t, J = 2.9 Hz, 1H), 1.51 (s, 6H) ppm.
[100] R-10: 1H NMR (400 MHz, CDCI3) δ 7.46 (d, J = 1.4 Hz, 1H), 7.31 - 7.27 (m, 1H), 7.18 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 7.2 Hz, 1H), 4.75 (t, J = 7.3 Hz, 1H), 4.30 (s, 2H), 4.01 - 3.03 (m, 2H), 1.47 (s, 6H) ppm.
[101] S-10’: 1H NMR (400 MHz, CDCI3) δ 7.54 (d, J = 1.4 Hz, 1H), 7.32 (dd, J = 7.5, 1.4 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 3.2 Hz, 1H), 4.75 (t, J = 3.2 Hz, 1H), 4.14 (s, 2H), 4.10 (t, J = 3.2 Hz, 1H), 4.04 (t, J = 3.2 Hz, 1H), 1.47 (s, 6H) ppm.
[102] R-10’: 1H NMR (400 MHz, CDCI3) δ 7.58 (d, J = 1.4 Hz, 1H),7.34 - 7.30 (m, 1H), 7.19 (d, J = 7.5 Hz, 1H), 4.91 (t, J = 2.9 Hz, 1H), 4.78 (t, J = 2.9 Hz, 1H), 4.13 (s, 2H), 3.95 - 3.88 (m, 2H), 1.45 (s, 6H) ppm.
[103] 19-(R,R):1H NMR (400 MHz, CDCI3) δ 7.47-7.43 (m, 1H), 7.29 (dd, J = 7.5, 1.4 Hz, 1H), 7.16 (d, J = 7.5 Hz, 1H), 4.94-4.88 (m, 2H), 4.75 (t, J = 3.0 Hz, 1H), 4.40 Petição 870250038759, de 13 / 05 / 2025, pág. 159 / 208 / 61 4.36 (m, 1H), 3.96-3.93 (m, 1H) 3.86-3.82 (m, 2H),1.55-1.48 (m, 2H), 0.99 (t, J = 6.8 Hz, 3H) ppm.
[104] 19-(R,S): 1H NMR (400 MHz, CDCI3) δ 7.41 (d, J = 1.4 Hz, 1H), 7.26-7.22 (m, 1H), 7.06 (d, J = 7.5 Hz, 1H), 5.12-5.08 (m, 1H), 4.87 (t, J = 2.8 Hz, 1H), 4.75 (t, J = 2.8 Hz, 1H), 4.24-4.20 (m, 1H), 4.06 - 3.90 (m, 2H), 3.86 (t, J = 2.8 Hz, 1H), 1.83 - 1.61 (m, 1H), 1.50-1.46 (m, 1H), 0.99 (t, J = 6.7 Hz, 3H) ppm.
[105] 19-(S,R): 1H NMR (400 MHz, CDCI3) δ 7.41 (d, J = 1.4 Hz, 1H), 7.29-7.25 (m, 1H), 7.07 (d, J = 7.4 Hz, 1H), 5.11-5.05 (m, 1H), 4.87 (t, J = 2.9 Hz, 1H), 4.75 (t, J = 2.9 Hz, 1H), 4.56-4.48 (m, 1H), 4.00 - 3.69 (m, 3H), 1.55-1.47 (m, 2H), 0.98 (t, J = 6.7 Hz, 3H) ppm.
[106] 19-(S,S): 1H NMR (400 MHz, CDCI3) δ 7.46 (d, J = 1.4 Hz, 1H), 7.33-7.27 (m, 2H), 5.11-5.06 (m, 1H), 4.87 (t, J = 3.5 Hz, 1H), 4.75 (t, J = 3.5 Hz, 1H), 4.33-4.30 (m, 1H), 4.10 - 3.82 (m, 3H), 1.67 - 1.41 (m, 2H), 0.98 (t, J = 6.7 Hz, 3H) ppm.
[107] 19’-(S,S): 1H NMR (400 MHz, CDCI3) δ 7.55 (d, J = 1.4 Hz, 1H), 7.35-7.32 (m, 1H), 7.16 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 2.8 Hz, 1H), 4.75 (t, J = 2.9 Hz, 1H), 4.24 3.97 (m, 2H), 3.88 - 3.39 (m, 3H), 1.96 - 1.51 (m, 2H), 0.99 (t, J = 6.7 Hz, 3H) ppm.
[108] 19’-(S,R): 1H NMR (400 MHz, CDCI3) δ 7.54 (d, J = 1.4 Hz, 1H), 7.32 (dd, J = 7.5, 1.4 Hz, 1H), 7.18 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 2.9 Hz, 1H), 4.75 (t, J = 2.9 Hz, 1H), 4.27 - 4.04 (m, 2H), 4.03 - 3.79 (m, 3H), 1.91 - 1.58 (m, 2H), 0.98 (t, J = 6.7 Hz, 3H) ppm.
[109] 19’-(R,R): 1H NMR (400 MHz, CDCI3) δ 7.55 (d, J = 1.5 Hz, 1H), 7.34-7.31 (m, 1H), 7.19 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 3.1 Hz, 1H), 4.75 (t, J = 3.1 Hz, 1H), 4.314.27(m, 1H), 4.20 - 3.95 (m, 3H), 3.85-3.81 (m, 1H), 1.89 - 1.72 (m, 1H), 1.71 - 1.54 (m, 1H), 0.99 (t, J = 6.7 Hz, 3H) ppm.
[110] 19'-(R,S): 1H NMR (400 MHz, CDCI3) δ 7.54 (d, J = 1.4 Hz, 1H), 7.32 (dd, J = 7.5, 1.4 Hz, 1H), 7.18-7.16 (m, 1H), 4.87 (t, J = 2.9 Hz, 1H) 0.97 (t, J = 6.7 Hz, 3H) ppm.
[111] 1.2.2 Determination of the specific rotation of the compound
[112] Using chloroform as a solvent, with a concentration of 1 Petition 870250038759, dated 05 / 13 / 2025, pp. 160 / 208 27 / 61 mg / mL, measure the specific rotation at 25 degrees Celsius, with the following specific data: 1-(S,R): [a]25D = -10.00 1-(S,S): [a]25D =-9.00 1-(R,R): [a]25D = +10.00 1-(R,S): [a]25D = +10.00 l'-(R,S): [a]25D =-8.00 l'-(R,R): [a]25D =+41.00 l'-(S,R): [a]25D = +7.00 l'-(S,S): [a]25D = -38.00 S-10: [a]25D =-12.00 R-10: [a]25D =+11.00 S-10': [a]25D =-7.00 R-10': [a]25D =+6.00 19-(R,R): [a]25D =+37.00 19-(R,S): [a]25D =-10.00 19-(S,R): [a]25D =+11.00 19-(S,S): [a]25D =-38.00 19'-(R,R): [a]25D =+9.00 19'-(R,S): [a]25D = +11.00 19'-(S,R): [a]25D =-12.00 19'-(S,S): [a]25D =-8.00
[113] According to the specific rotation results, they are consistent with the absolute configuration inferred by the NMR analysis. Therefore, the product configuration must be correct. Example 6: Synthesis of compound 1 Petition 870250038759, dated 05 / 13 / 2025, pp. 161 / 208 28 / 61 Step 1: I-1 ii-1 iii-1
[114] Add phenol-2,4-dichloride (1 g, 6.2 mmol) to a reaction flask, dissolve in 20 mL of DMF, add propanol epoxy (722 mg, 7.6 mmol) and cesium carbonate (8 g, 24.8 mmol), and carry out the reaction in an oil bath at 100°C. After 6 hours, monitor the reaction by TLC until completion, add 100 mL of water, extract with ethyl acetate (30 mL x 3), wash with saturated saline water, collect the organic phase, dry with anhydrous sodium sulfate, concentrate under vacuum and purify by chromatography, including chiral preparation (Equipment: Shimadzu high-pressure preparation liquid chromatograph, model LC20AR; Chiral column: CHIRALPAK® IG normal phase chiral column, 4.6 mm ID x 250 mm, diameter: 5 µm; Mobile phase: Hexane:isopropanol = 90:10) to obtain Chemical Compound iii-1 (781 mg, colorless and transparent liquid).
[115] Add dichloro thiosulfate (293 mg, 2.5 mmol) to a reaction flask, dissolve in 20 mL of dichloromethane and stir in an ice bath at 0°C. Slowly add Chemical Compound iii-1' (356 mg, 1.6 mmol). After addition, allow the reaction to stand at room temperature for 10 hours, monitor the reaction by TLC until completion, concentrate the reaction solution under vacuum to obtain a yellowish oil, which is the crude product of compounds v-1, for further use. Step 3: Petition 870250038759, dated 05 / 13 / 2025, pages 162 / 208 29 / 61
[116] Add compound vi-1 (123 mg, 1.9 mmol) to a reaction flask, add triethylamine (243 mg, 2.4 mmol) and stir in an ice bath at 0°C. Slowly add chemical compound v-1 (480 mg, 1.6 mmol). After addition, allow the reaction to stand at room temperature for 6 hours, monitor the reaction by TLC until completion, add 100 mL of water to the reaction solution, extract with dichloromethane (30 mL x 3), wash with saturated saline, collect the organic phase, dry with anhydrous sodium sulfate, concentrate under vacuum and purify by column chromatography to obtain compound 1 (423 mg, oily substance).
[117] 2.9 Hz, 1H), 4.64 - 4.54 (m, 1H), 4.51 - 4.46 (m, 1H), 4.14 - 4.10 (m, 1H), 3.95 (t, J = 2.8 Hz, 1H), 3.88 (t, J = 2.9 Hz, 1H), 1.40 (d, J = 5.7 Hz, 3H) ppm.
[118] HRMS (ESI) Calc. For CiiHi4CI2FO4SNa+[M+Na]+352.9768; Found: 352.9789, 354.9773 Example 7: Synthesis of Chemical Compound 1'
[119] Synthesis of compound iii-Γ according to Step 6 of Example 1, followed by chiral preparation to obtain the target compound iii-Γ.
[120] Step 2: Identical to Step 2 of Example 1.
[121] Step 3: Identical to Step 3 of Example 1.
[122] After synthesis, the target compound 1' (423 mg, colorless liquid and Petition 870250038759, dated 05 / 13 / 2025, pp. 163 / 208 30 / 61 transparent).
[123] XH NMR (400 MHz, CDCl3) 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, 6.3 Hz, 1H), 4.02 (dd, J = 10.0, 4.3 Hz, 1H), 1.52 (d, J = 6.5 Hz, 3H) ppm.
[124] HRMS (ESI) Calcd. For CiiHi4Cl2FO4SNa+[M+Na]+352.9768; Found: 352.9786, 354.9758. Example 8: Synthesis of compound 10 Step 1: I-1 iii-10
[125] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-10.
[126] Step 2: Identical to Step 2 of Example 1.
[127] Step 3: Identical to Step 3 of Example 1.
[128] After synthesis, target compound 10 (685 mg, colorless and transparent liquid) was obtained.
[129] 1H NMR (400MHz, CDCI3) δ 7.46 (d, J = 1.4Hz, 1H), 7.29 (dd, J = 7.5, 1.4Hz, 1H), 7.18 (d, J = 7.5Hz, 1H), 4.87 (t, J = 7.2Hz, 1H), 4.75 (t, J = 7.3 Hz, 1H), 4.30 (s, 2H), 4.03 - 3.03 (m, 2H), 1.47 (s, 6H) ppm.
[130] HRMS (ESI) Calc. For Ci2Hi6CI2FO4S+[M+H]+345.0125; Found:345.0143. Example 9: Synthesis of compound 10' 10' Petition 870250038759, dated 05 / 13 / 2025, pp. 164 / 208 31 / 61 iii-10'
[131] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-10.
[132] Step 2: Identical to Step 2 of Example 1.
[133] Step 3: Identical to Step 3 of Example 1.
[134] After synthesis, target compound 10 (311 mg, colorless and transparent liquid) was obtained.
[135] 1H NMR (400 MHz, CDCI3) δ 7.62 (d, J = 1.4 Hz, 1H), 7.29 - 7.27 (m, 1H), 7.16 (d, J = 7.5 Hz, 1H), 4.87 (t, J = 2.9 Hz, 1H), 4.75 (t, J = 2.9 Hz, 1H), 4.13 (s, 2H), 4.04 (t, J = 2.9 Hz, 1H), 3.97 (t, J = 2.9 Hz, 1H), 1.37 (s, 6H).
[136] HRMS (ESI) Calc. For Ci2Hi6Cl2FO4S+[M+H]+345.0125; Found:345.0126. Example 10: Synthesis of compound 19 Step 1: i-1 ii-19 iii-19
[137] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-19.
[138] Step 2: Identical to Step 2 of Example 1.
[139] Step 3: Identical to Step 3 of Example 1.
[140] After synthesis, target compound 19 (692 mg, colorless and transparent liquid) was obtained. Petition 870250038759, dated 05 / 13 / 2025, pp. 165 / 208 32 / 61
[141] 4.39-4.34 (m, 1H), 3.99-3.77 (m, 3H), 1.56-1.43 (m, 2H), 0.99 (t, J = 6.8 Hz, 3H) ppm.
[142] HRMS (ESI) Calc. For Ci2Hi5O4CI2FS+[M+H]+344.0052; Found:344.0026. Example 11: Synthesis of compound 19' 19' Step 1: iii-19'
[143] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-19'.
[144] Step 2: Identical to Step 2 of Example 1.
[145] Step 3: Identical to Step 3 of Example 1.
[146] After synthesis, target compound 19' (309 mg, colorless and transparent liquid) was obtained.
[147] 1H NMR (400 MHz, CDCI3) δ 7.55 (d, J = 1.4 Hz, 1H), 7.32 (dd, J = 7.5, 1.4 Hz, 1H), 7.21-7.17 (m, 1H), 4.87 (t, J = 3.1 Hz, 1H), 4.75 (t, J = 3.1 Hz, 1H),4.61-4.57 (m, 1H), 4.25 - 3.88 (m, 4H), 1.80-1.75 (m, 1H)), 1.71 - 1.54 (m, 1H), 0.96 (t, J = 6.7 Hz, 3H) ppm.
[148] HRMS (ESI) Calc. For Ci2Hi5O4CI2FS+[M+H]+344.0052; Found:344.0071. Example 14: Synthesis of compound 22' Petition 870250038759, dated 05 / 13 / 2025, pp. 166 / 208 33 / 61 Step 1: iii-22
[149] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-22.
[150] Step 2: Identical to Step 2 of Example 1.
[151] Step 3: Identical to Step 3 of Example 1.
[152] After synthesis, target compound 22 (671 mg, colorless and transparent liquid) was obtained.
[153] 1H NMR (400 MHz, CDCl3) 5.34 (m, 1H), 5.25 - 5.12 (m, 2H), 4.87 (t, J = 3.0 Hz, 1H), 4.75 (t, J = 3.0 Hz, 1H), 4.39 (dd, J = 12.5, 2.4 Hz, 1H), 4.13 4.02 (m, 2H), 3.99 (t, J = 3.0 Hz, 1H) ppm.
[154] HRMS (ESI) Calcd. For Ci2Hi3O4Cl2FS+[M+H]+341.9896; Found:341.9857. Example 15: Synthesis of compound 22' 22' Step 1: I-1 iii-22'
[155] According to Step 1 of Example 6, followed by chiral preparation to obtain target compound iii-22'.
[156] Step 2: Identical to Step 2 of Example 1.
[157] Step 3: Identical to Step 3 of Example 1.
[158] After synthesis, the target compound 22' (297 mg, colorless and transparent liquid) was obtained. Petition 870250038759, dated 05 / 13 / 2025, pp. 167 / 208 34 / 61
[159] 1H NMR (400 MHz, CDCl3) 5.15 (m, 2H), 4.87 (t, J = 3.0 Hz, 1H), 4.75 (t, J = 3.0 Hz, 1H), 4.54 - 4.50 (m, 1H), 4.14 (dd, J = 12.5, 5.1 Hz, 1H), 3.75 (dd, J = 12.4, 5.0Hz, 1H), 3.65 (t, J = 3.0 Hz, 1H), 3.59 (t, J = 3.0 Hz, 1H) ppm.
[160] HRMS (ESI) Calc. For C^HisCUCbFS* [M+H]+341.9896; Found:341.9903. Example 16: Synthesis of compound 25 Step 1: I ii-25 iii-25
[161] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-22'.
[162] Step 2: Identical to Step 2 of Example 1.
[163] Step 3: Identical to Step 3 of Example 1.
[164] After synthesis, target compound 25 (703 mg, colorless and transparent liquid) was obtained. Example 17: Synthesis of compound 28 Step 1:
[165] According to Step 1 of Example 6, followed by chiral preparation to obtain the target compound iii-28.
[166] Step 2: Identical to Step 2 of Example 1. Petition 870250038759, dated 05 / 13 / 2025, pp. 168 / 208 / 61
[167] Step 3: Identical to Step 3 of Example 1.
[168] After synthesis, target compound 28 (671 mg, colorless and transparent liquid) was obtained.
[169] The remaining compounds were synthesized according to the synthesis methods mentioned above, and the structure of all compounds is presented in Table 1. Table 1 Código R1 R2 R3 R3’ R4 R4’ R5 1 2-Cl 4-Cl CH3 H H H CH2CH2F 1’ 2-Cl 4-Cl H H CH3 H CH2CH2F 2 2-Cl 4-Cl CH3 H H H CH2CH2Cl 2’ 2-Cl 4-Cl H H CH3 H CH2CH2Cl 3 2-Cl 4-Cl CH3 H H H CH2CH2Br 3’ 2-Cl 4-Cl H H CH3 H CH2CH2Br 4 3-Cl 5-Cl CH3 H H H CH2CH2F 4’ 3-Cl 5-Cl H H CH3 H CH2CH2F 5 3-Cl 5-Cl CH3 H H H CH2CH2Q 5’ 3-Cl 5-Cl H H CH3 H CH2CH2Q 6 3-Cl 5-Cl CH3 H H H CH2CH2Br 6’ 3-Cl 5-Cl H H CH3 H CH2CH2Br 7 2-Cl 5-Cl CH3 H H H CH2CH2F 7’ 2-Cl 5-Cl H H CH3 H CH2CH2F 8 2-Cl 5-Cl CH3 H H H CH2CH2Cl 8’ 2-Cl 5-Cl H H CH3 H CH2CH2Q 9 2-Cl 5-Cl CH3 H H H CH2CH2Br 9’ 2-Cl 5-Cl H H CH3 H CH2CH2Br 10 2-Cl 4-Cl H H CH3 CH3 CH2CH2F 10’ 2-Cl 4-Cl CH3 CH3 H H CH2CH2F 11 2-Cl 4-Cl H H CH3 CH3 CH2CH2Cl 11’ 2-Cl 4-Cl CH3 CH3 H H CH2CH2Cl 12 2-Cl 4-Cl H H CH3 CH3 CH2CH2Br 12’ 2-Cl 4-Cl CH3 CH3 H H CH2CH2Br 13 3-Cl 5-Cl H H CH3 CH3 CH2CH2Br 13’ 3-Cl 5-Cl CH3 CH3 H H CH2CH2F 14 3-Cl 5-Cl H H CH3 CH3 CH2CH2F 14’ 3-Cl 5-Cl CH3 CH3 H H CH2CH2Q 15 3-Cl 5-Cl H H CH3 CH3 CH2CH2Cl 15’ 3-Cl 5-Cl CH3 CH3 H H CH2CH2Br 162-Cl 5-Cl H H CH3 CH3 CH2CH2Br 16’ 2-Cl 5-Cl CH3 CH3 H H CH2CH2F 17 2-Cl 5-Cl H H CH3 CH3 CH2CH2F Petição 870250038759, de 13 / 05 / 2025, pág. 169 / 208 / 61 17’ 2-Cl 5-Cl CH3 CH3 H H CH2CH2Cl 18 2-Cl 5-Cl H H CH3 CH3 CH2CH2Cl 18’ 2-Cl 5-Cl CH3 CH3 H H CH2CH2Br 19 2-Cl 4-Cl H H CH2CH3 H CH2CH2F 19’ 2-Cl 4-Cl CH2CH3 H H H CH2CH2F 20 3-Cl 5-Cl H H CH2CH3 H CH2CH2F 20’ 3-Cl 5-Cl CH2CH3 H H H CH2CH2F 21 2-Cl 5-Cl H H CH2CH3 H CH2CH2F 21’ 2-Cl 5-Cl CH2CH3 H H H CH2CH2F 22 2-Cl 4-Cl H H CH=CH2 H CH2CH2F 22’ 2-Cl 4-Cl CH=CH2 H H H CH2CH2F 23 3-Cl 5-Cl H H CH=CH2 H CH2CH2F 23’ 3-Cl 5-Cl CH=CH2 H H H CH2CH2F 24 2-Cl 5-Cl H H CH=CH2 H CH2CH2F 24’ 2-Cl 5-Cl CH=CH2 H H H CH2CH2F 25 2-Cl 4-Cl CH2CH2F 26 3-Cl 5-Cl CH2CH2F 27 2-Cl 5-Cl CH2CH2F 28 2-Cl 4-Cl H H H H CH2CH2F 29 3-Cl 5-Cl H H H H CH2CH2F 30 2-Cl 5-Cl H H H H CH2CH2F Example of Experiment 1: Effect 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, compound 1' S-10, R-10, R-10', 10, 10', 19-(S,S), 19(S,R), 19-(R,R), 19-(R,S) 19'-(S,S) 19'-(S,R) 19'-(R,R) 19'-(R,S), 19 and 19' on the hatching of Tetranychus cinnabarinus (red mite) eggs
[170] 1. Experimental Method
[171] (1) Preparation of leaves with eggs: Transfer 20 adult females of Tetranychus cinnabarinus to a 2.0 cm diameter honeycomb leaf disc (with moistened filter paper at the bottom), cover it with a lidded culture dish to maintain humidity and culture it. Remove the adult females within 36 hours and examine the egg leaf disc under a microscope for counting.
[172] (2) Initial egg count: Count the eggs on each leaf disc before treatment with the compost, using a microscope. Perform two replicates for each treatment. Petition 870250038759, dated 05 / 13 / 2025, pages 170 / 208 / 61
[173] (3) Treatment with compounds: Immerse the leaf discs with mite eggs in clean water for 10 seconds, remove and cultivate maintaining moisture, with at least 3 repetitions per treatment.
[174] (4) Cultivation and observation: Place the treated mite eggs and leaf discs under normal cultivation conditions. After 5 days of treatment, begin investigating the hatching of mite eggs.
[175] Note: It is necessary to control the temperature and humidity conditions in the incubator after treatment, avoiding excessive temperature variations and the formation of condensation that could wet and drown the eggs. In addition, strong lighting should be ensured in the environment, but direct light on the leaves should be avoided.
[176] (5) Investigation result: Regularly, samples from each treatment group were hydrated to maintain moisture and observe egg hatching. On the seventh day after treatment application, the number of eggs hatched in each group was recorded. The results were noted in an original logbook. Depending on the requirements of the experiment and the characteristics of the agent used, the investigation time may be shortened or extended.
[177] Research index:
[178] @ Record the number of hatched eggs in each treatment.
[179] @ Photograph to check if damage occurred to the pea leaf disc due to treatment.
[180] @ Record the developmental stage of mite eggs and larval behavior, such as delayed or stopped development, difficulty hatching, or abnormal behavior after hatching, such as fighting after hatching.
[181] (6) Calculation Method: Based on the research data, calculate the effectiveness of each treatment using the following formula, keeping the results to two decimal places.
[182] Egg hatching rate (%) = Number of hatched eggs / Total number of eggs treated * 100
[183] Control effectiveness (%) = (Egg hatching rate in the control zone - Petition 870250038759, dated 05 / 13 / 2025, pp. 171 / 208 / 61 (Egg hatching rate in the treated zone) / (Egg hatching rate in the control zone) * 100
[184] The experimental design is shown in Figure 2. Table 2 Experimental design Treatment Code Experiment Treatment Experiment Concentration (mg / mL) Application Method Application Period T1 Chemical Compound 1 1 Leaf Butterfly / T2 Chemical Compound 1 0.5 T3 Chemical Compound 1 0.25 T4 1-(S,S) 1 T5 1-(S,S) 0.5 T6 1-(S,S) 0.25 T7 1-(S,R) 1 T8 1-(S,R) 0.5 T9 1-(S,R) 0.25 T10 1-(R,R) 1 T11 1-(R,R) 0.5 T12 1-(R,R) 0.25 T13 1-(R,S) 1 T14 1-(R,S) 0.5 T15 1-(R,S) 0.25 T16 Chemical Compound 1' 1 T17 Chemical compound 1' 0.5 T18 Chemical compound 1' 0.25 T19 1'-(S,S) 1 T20 1'-(S,S) 0.5 T21 1'-(S,S) 0.25 T22 1'-(S,R) 1 T23 1'-(S,R) 0.5 T24 1'-(S,R) 0.25 Petition 870250038759, dated 05 / 13 / 2025, page 172 / 208 / 61 T25 1'-(R,R) 1 T26 1'-(R,R) 0.5 T27 1'-(R,R) 0.25 T28 1'-(R,S) 1 T29 1'-(R,S) 0.5 T30 1'-(R,S) 0.25 T31 Chemical compound 10 1 T32 Chemical compound 10 0.5 T33 Chemical compound 10 0.25 T34 S-10 1 T35 S-10 0.5 T36 S-10 0.25 T37 R-10 1 T38 R-10 0.5 T39 R-10 0.25 T40 Chemical compound 10' 1 T41 Chemical compound 10' 0.5 T42 Chemical compound 10' 0.25 T43 S-10' 1 T44 S-10' 0.5 T45 S-10' 0.25 T46 R-10' 1 T47 R-10' 0.5 T48 R-10' 0.25 T49 Chemical compound 19 1 T50 Chemical compound 19 0.5 T51 Chemical compound 19 0.25 T52 19-(S,S) 1 T53 19-(S,S) 0.5 Petition 870250038759, dated 05 / 13 / 2025, page 173 / 208 / 61 T54 19-(S,S) 0.25 T55 19-(S,R) 1 T56 19-(S,R) 0.5 T57 19-(S,R) 0.25 T58 19-(R,R) 1 T59 19-(R,R) 0.5 T60 19-(R,R) 0.25 T61 19-(R,S) 1 T62 19-(R,S) 0.5 T63 19-(R,S) 0.25 T64 Chemical compound 19' 1 T65 Chemical compound 19' 0.5 T66 Chemical compound 19' 0.25 T67 19'-(S,S) 1 T68 19'-(S,S) 0.5 T69 19'-(S,S) 0.25 T70 19'-(S,R) 1 T71 19'-(S,R) 0.5 T72 19'-(S,R) 0.25 T73 19'-(R,R) 1 T74 19'-(R,R) 0.5 T75 19'-(R,R) 0.25 T76 19'-(R,S) 1 T77 19'-(R,S) 0.5 T78 19'-(R,S) 0.25 T79 Comparison of solvents / T80 Clear water /
[185] 2. The result of the experiment
[186] The results are presented in Table 3. The compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), as well as the compounds 1 and 1', S-10, S-10', 10, 10', 19-(S, R), Petition 870250038759, dated 05 / 13 / 2025, pp. 174 / 208 / 61 19-(R,S), 19'-(S,S), 19'-(R,R), 19 and 19' demonstrated excellent inhibitory activity on the hatching of Tetranychus cinnabarinus (red mite) eggs at a concentration of 1 ppm. Table 3 Treatment Basic number of eggs before treatment Number of unhatched eggs 7 days after treatment Hatching rate (%) Replication 1 Replication 2 Replication 1 Replication 2 Replication 1 Replication 2 T1 53 61 53 60 0.00 1.64 T2 62 47 42 29 32.58 38.30 T3 72 53 20 17 72.22 67.92 T4 75 68 75 68 0.00 0.00 T5 70 72 70 65 0.00 9.72 T6 57 59 28 36 50.88 38.98 T7 78 64 76 64 2.56 0.00 T8 51 64 33 44 35.29 31.25 T9 47 46 19 11 59.57 76.09 T10 56 62 56 62 0.00 0.00 T11 47 72 45 68 4.26 5.56 T12 66 51 36 28 45.45 45.10 T13 64 45 61 42 4.69 6.67 T14 71 49 40 25 43.66 48.98 T15 51 68 13 14 74.51 76.47 T16 47 59 47 58 0.00 1.69 T17 61 45 42 31 36.24 31.11 T18 53 72 16 21 69.81 70.83 T19 55 41 46 35 16.36 14.63 T20 58 75 42 66 27.59 12.00 T21 48 46 17 14 64.58 69.57 T22 69 78 69 78 0.00 0.00 T23 45 62 41 60 8.89 3.23 T24 49 58 28 32 42.86 44.83 T25 67 75 50 69 25.37 8.00 T26 57 63 36 40 36.84 36.51 T27 46 45 14 8 69.57 82.22 T28 62 42 62 42 0.00 0.00 T29 80 80 79 76 1.25 5.00 T30 48 96 22 68 54.17 29,17 T31 81 78 80 78 1.23 0.00 T32 69 63 47 41 31.88 34.92 T33 73 56 24 20 67.12 64.29 T34 78 84 78 84 0.00 0.00, Petition 870250038759, dated 05 / 13 / 2025, pages 175 / 208 / 61 T35 65 59 62 57 4.62 3.39 T36 81 67 49 39 39.51 41.79 T37 74 64 68 60 8.11 6.25 T38 48 62 28 36 42.67 41.94 T39 56 77 15 20 73.21 74.03 T40 76 68 75 66 1.32 2.94 T41 68 83 47 58 30.88 30.12 T42 82 57 27 17 67.07 70.18 T43 59 84 59 84 0.00 0.00 T44 88 49 81 46 7.95 6.12 T45 76 65 44 37 42.11 43.77 T46 59 67 54 62 8.47 7.46 T47 63 71 36 39 42.86 45.07 T48 81 56 21 13 74.07 T53 67 76.79 61 53 48 20.90 21.31 T54 58 73 20 22 65.52 69.86 T55 60 68 60 68 0.00 0.00 T56 78 57 74 54 5.13 5.26 T57 62 57 35 31 43.55 45.61 T58 47 66 40 55 14.89 16.67 T59 69 50 44 34 36.23 36.00 T60 72 75 18 18 75.00 76.00 T61 59 67 59 67 0.00 0.00 T62 48 56 47 54 2.08 3.57 T63 63 58 38 34 39.68 41.38 T64 53 63 52 63 1.89 0.00 T65 72 61 47 40 34.72 34.43 T66 47 71 14 19 70.21 73.24 T67 56 49 56 49 0.00 0.00 T68 70 56 66 54 5.71 3.57 T69 49 73 29 44 40.82 39.73 T70 68 54 68 53 0.00 1.85 T71 57 61 37 41 35,09 32.79 T72 73 65 23 20 68.49 69.23 T73 57 69 57 69 0.00 0.00 T74 52 67 49 64 5.77 4.48 T75 71 49 39 27 45.07 44.90 T76 50 62 47 58 6.00 6.45 T77 71 69 38 38 46.48 44.93 T78 64 70 19 20 70.31 71.43, Petition 870250038759, dated 05 / 13 / 2025, pp. 176 / 208 / 61 T79 73 55 3 2 95.89 96.36 T80 81 82 1 2 98.16 Example Experiment 1: Effect 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', S10, S-10', 10, 10', 19-(S,R), 19-(R,S), 19'-(S,S), 19'-(R,R), 19 and 19' on the hatching of thrips eggs.
[187] This experiment adopts the method described in the technical section of Example Experiment 1, primarily using the leaf disc method to explore the effect 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), 1, 1', S-10, S-10', 10, 10', 19-(S, R), 19-(R,S), 19'-(S,S), 19'-(R,R), 19 and 19', as well as compounds 1 and 1', on the inhibition of thrips egg hatching. The concentration of the chemical compound is 100 ppm.
[188] The results presented in Table 4. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), as well as compounds 1, 1', S-10, S-10', 10, 10', 19-(S, R), 19-(R,S), 19'-(S,S), 19'-(R,R), 19 and 19' demonstrated strong inhibitory activity on thrips egg hatching at a concentration of 100 ppm. Table 4 Treatment Basic number of eggs before treatment Number of larvae hatched 5 days after treatment Hatching rate (%) Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Chemical compound 1 77 127 92 0 2 0 0.00 1.57 0.00 1-(S,S) 83 105 138 0 0 0 0.00 0.00 0.00 1-(S,R) 141 96 107 17 8 11 12.06 8.33 10.28 1-(R,R) 125 110 128 0 0 0 0.00 0.00 0.00 1-(R,S) 94 133 88 9 12 7 9.57 9.02 7.95 Chemical compound 1' 142 87 103 0 0 1 0.00 0.00 0.97 1'-(S,S) 78 123 106 11 18 17 14.10 14.63 16.04 1'-(S,R) 99 135 121 0 0 0 0.00 0.00 0.00 1'-(R,R) 146 86 105 18 11 15 12.68 12.79 14.29 1'-(R,S) 104 145 97 0 0 0 0.00 0.00 0.00 S-10 85 109 112 0 0 0 0.00 0.00 0.00 R-10 98 131 117 15 19 17 15.31 14.50 14.53 Petition 870250038759, dated 05 / 13 / 2025, pages 177 / 208 / 61 Chemical compound 10 101 92 109 1 0 0 0.99 0.00 0.00 S-10' 133 86 102 0 0 0 0.00 0.00 0.00 R-10' 122 93 136 17 14 19 13.93 15.05 13.97 Chemical compound 10' 118 129 91 0 2 0 0.00 1.55 0.00 Chemical compound 19 113 120 98 0 1 0 0.00 0.83 0.00 19-(S,S) 125 108 96 18 15 11 14.4 13.89 11.46 19-(S,R) 117 92 134 0 0 0 0.00 0.00 0.00 19-(R,R) 95 104 115 12 14 15 12.63 13.46 13.04 19-(R,S) 87 125 109 0 0 0 0.00 0.00 0.00 Chemical compound 19' 105 87 135 1 1 0 0.95 1.15 0.00 19'-(S,S) 114 132 97 0 0 0 0.00 0.00 0.00 19'-(S,R) 117 126 84 11 13 8 9.40 10.32 9.52 19'-(R,R) 141 86 92 0 0 0 0.00 0.00 0.00 19'-(R,S) 133 98 103 12 9 9 9.02 9.18 8.74 Comparison of solvents 129 93 117 124 92 113 97.21 Clear water 118 96 93 117 94 91 98.31 Example Experiment 3: Effect 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', S10, R-10, S-10', R-10', compound 10, compound 10', compound 19-(S,S), 19(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), compound 19 and compound 19' on the hatching of Tetranychus urticae eggs.
[189] This experiment adopts the method described in the technical section of Example Experiment 1, primarily using the leaf disk method to explore the effect of chemical 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), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', compound 10, compound 10', compound 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), compound 19 and compound 19' on inhibiting the hatching of eggs of Tetranychus urticae. The concentration of the chemical compound is 5 ppm.
[190] The results presented in Table 5. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', compound Petition 870250038759, dated 05 / 13 / 2025, pp. 178 / 208 / 61 Compounds 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated strong inhibitory activity on the hatching of Tetranychus urticae eggs. Table 5 Treatment Basic number of eggs before treatment Number of larvae hatched 5 days after treatment Hatching rate (%) Replication 1 Replication 2 Replication 1 Replication 2 Replication 1 Replication 2 Chemical compound 1 106 77 1 1 0.94 1.30 1-(S,S) 83 76 0 0 0.00 0.00 1-(S,R) 92 74 10 9 10.87 12.16 1-(R,R) 103 85 0 0 0.00 0.00 1-(R,S) 78 63 11 88 14.10 12.70 Chemical compound 1' 64 101 0 2 0.00 1.98 1'-(S,S) 63 74 13 12 20.63 16.22 1'-(S,R) 95 68 0 0 0.00 0.00 1'-(R,R) 67 83 12 16 17.91 19.28 1'-(R,S) 91 69 0 0 0.00 0.00 S-10 88 76 0 0 0.00 0.00 R-10 72 93 13 15 18.06 16.13 Chemical compound 10 103 74 2 1 1.94 1.35 S-10' 69 85 0 0 0.00 0.00 R-10' 79 96 14 16 17.72 16.67 Chemical compound 10' 85 91 1 1 1.18 1.10 Chemical compound 19 87 92 0 1 0.00 1.09 19-(S,S) 103 95 18 14 17.48 14.74 19-(S,R) 94 98 0 0 0.00 0.00 19-(R,R) 89 106 16 19 17.98 17.92 19-(R,S) 78 96 0 0 0.00 0.00 Chemical compound 19' 88 104 1 2 1.14 1.92 19'-(S,S) 100 99 0 0 0.00 0.00 Petition 870250038759, dated 05 / 13 / 2025, pages 179 / 208 / 61 19'-(S,R) 111 87 12 10 10.81 11.49 19'-(R,R) 95 98 0 0 0.00 0.00 19'-(R,S) 79 83 10 11 12.66 13.25 Comparison of solvents 59 76 56 74 92.29 Clear water 74 82 73 80 98.11 Example of Experiment 4: Effect 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', S10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' on the hatching of Panonychus citri eggs.
[191] This experiment adopts the method described in the technical part of Example Experiment 1, using mainly the leaf disc method to explore the effect of chemical compound 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'(S,R), 1'-(R,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' on the hatching of Panonychus citri eggs. The concentration of the chemical compound is 1 ppm.
[192] The results are presented in Table 6. Compounds 1-(S,S), 1(R,R), 1'-(S,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated excellent inhibitory activity on the hatching of Panonychus citri eggs. Table 6 Treatment Basic number of eggs before treatment Number of larvae hatched 5 days after treatment Hatching rate (%) Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Chemical compound 1 122 87 133 1 1 2 0.82 1.15 1.50 1-(S,S) 142 98 77 0 0 0 0.00 0.00 0.00 1-(S,R) 103 87 132 6 5 8 5.83 5.75 6.06 1-(R,R) 131 102 89 0 0 0 0.00 0.00 0.00 Petition 870250038759, dated 05 / 13 / 2025, pages 180 / 208 / 61 1-(R,S) 98 143 86 7 12 7 7.14 8.39 8.14 Chemical compound 1' 107 132 78 1 2 0 0.93 1.52 0.00 1'-(S,S) 129 81 108 19 13 18 14.73 16.05 16.67 1'-(S,R) 104 133 80 0 0 0 0.00 0.00 0.00 1'-(R,R) 72 99 127 6 7 7 8.33 7.07 5.51 1'-(R,S) 132 94 107 0 0 0 0.00 0.00 0.00 S-10 123 109 96 0 0 0 0.00 0.00 0.00 R-10 114 92 135 11 9 14 9.65 9.78 10.37 Chemical compound 10 99 81 117 1 0 0 1.01 0.00 0.00 S-10' 89 125 106 0 0 0 0.00 0.00 0.00 R-10' 136 97 104 14 10 10 10.29 10.31 9.62 Chemical compound 10' 112 137 109 0 1 1 0.00 0.73 0.92 Chemical compound 19 125 106 94 0 0 0 0.00 0.00 0.00 19-(S,S) 119 101 86 12 10 9 10.08 9.90 10.47 19-(S,R) 102 98 125 0 0 0 0.00 0.00 0.00 19-(R,R) 133 107 84 10 9 7 7.52 8.41 8.33 19-(R,S) 92 123 114 0 0 0 0.00 0.00 0.00 Chemical compound 19' 89 98 116 0 0 0 0.00 0.00 0.00 19'-(S,S) 127 113 98 0 0 0 0.00 0.00 0.00 19'-(S,R) 94 107 119 9 11 12 9.57 10.28 10.08 19'-(R,R) 132 79 108 0 0 0 0.00 0.00 0.00 19'-(R,S) 115 96 94 12 10 9 10.43 10.42 9,57 Comparison of solvents 103 101 107 98 97 103 95.82 Clear water 99 102 98 96 99 96 97.33 Example Experiment 5: Effect 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', S10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' on the hatching of Aleurocybotus indicus eggs.
[193] This experiment adopts the method described in the technical section of Example Experiment 1, primarily using the leaf disk method for Petition 870250038759, dated 05 / 13 / 2025, page. 181 / 208 / 61 explore the effect of chemical compound 1-(S,S), 1-(S,R), 1-(R,R), 1-(R,S), 1'-(S,S), 1'(S,R), 1'-(R,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' on the inhibition of Aleurocybotus indicus egg hatching. The concentration of the chemical compound is 10 ppm.
[194] The results presented in Table 7. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', 10, 10', 19(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated strong inhibitory activity on the hatching of Aleurocybotus indicus eggs. Table 7 Treatment Basic number of eggs before treatment Number of larvae hatched 5 days after treatment Hatching rate (%) Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Chemical compound 1 89 133 112 0 2 0 0.00 1.50 0.00 1-(S,S) 87 96 131 0 0 0 0.00 0.00 0.00 1-(S,R) 114 128 105 11 12 11 9.65 9.38 10.48 1-(R,R) 149 121 94 0 0 0 0.00 0.00 0.00 1-(R,S) 88 135 121 7 10 9 7.95 7.41 7.44 Chemical compound 1' 107 79 88 2 0 1 1.87 0.00 1.14 1'-(S,S) 132 105 78 20 17 12 15.15 16.19 15.38 1'-(S,R) 94 141 89 0 0 0 0.00 0.00 0.00 1'-(R,R) 129 91 106 18 14 14 13.95 15.38 13.21 1'-(R,S) 110 96 128 0 0 0 0.00 0.00 0.00 S-10 102 92 104 0 0 0 0.00 0.00 0.00 R-10 143 138 121 14 13 12 9.79 9.42 9.92 Chemical compound 10 132 107 124 1 0 2 0.76 0.00 1.61 S-10' 81 128 136 0 0 0 0.00 0.00 0.00 R-10' 133 88 128 13 9 13 9.77 10.23 10.16 Chemical compound 10' 99 103 95 2 1 1 2.02 0.97 1.05 Chemical compound 19 96 112 109 0 0 0 0.00 0.00 0,00, Petition 870250038759, dated 05 / 13 / 2025, pp. 182 / 208 / 61 19-(S,S) 89 133 114 11 16 14 12.36 12.03 12.28 19-(S,R) 78 102 95 0 0 0 0.00 0.00 0.00 19-(R,R) 92 98 125 11 10 14 11.96 10.20 11.20 19-(R,S) 102 113 108 0 0 0 0.00 0.00 0.00 Chemical compound 19' 115 86 99 0 0 0 0.00 0.00 0.00 19'-(S,S) 107 126 134 0 0 0 0.00 0.00 0.00 19'-(S,R) 95 127 98 10 13 10 10.53 10.24 10.20 19'-(R,R) 84 93 135 0 0 0 0.00 0.00 0.00 19'-(R,S) 126 117 87 13 11 10 10.32 9.40 11.49 Comparison of solvents 129 93 112 127 90 109 97.51 Clear water 118 91 86 117 89 85 98.85 Example Experiment 6: Effect 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', S10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' on the hatching of Spodoptera litura eggs.
[195] 1. Experiment solution
[196] (1) Egg paper preparation: Cut the eggs into small pieces, each containing about 60 eggs. Submerge each piece, along with the oviposition paper, in a previously prepared test solvent for 10 minutes (The concentration of the chemical compound is 500 ppm). Remove and use absorbent paper to remove the excess solution that adheres to the oviposition paper and the eggs.
[197] (2) Cultivation: Each egg piece was placed in a glass tube (5.0 cm high and 2.5 cm in diameter, the same dimensions apply below). The tube was sealed with a plastic sheet perforated with an insect pin and placed in an artificial climate chamber with a temperature of (24 ± 1) °C, relative humidity of (80 ± 10)% and a photoperiod cycle of L:D = 12:12 for cultivation, when the eggs are about to hatch, add Ricinus communis leaves (about 3 cm in diameter) so that the newly hatched larvae can feed;
[198] (3) Note: Check and record the number of hatched and unhatched eggs Petition 870250038759, dated 05 / 13 / 2025, page 183 / 208 / 61 hatchlings in each block of eggs, and calculate the hatching rate of the eggs according to the formula. Each treatment was performed with three repetitions.
[199] (4) Investigation result: Regularly, samples from each treatment group were hydrated to maintain moisture and observe egg hatching. On the fourth day after treatment application, the number of hatched eggs in each group was recorded. The results were noted in an original logbook. Depending on the requirements of the experiment and the characteristics of the agent used, the investigation time may be shortened or extended.
[200] Research index:
[201] @ Record the number of hatched eggs in each treatment.
[202] @ Record the developmental stage of Spodoptera litura eggs and the behavior of the larvae, such as delays or stops in the development of Spodoptera litura eggs and other abnormal phenomena.
[203] (5) Calculation Method: Based on the research data, calculate the effectiveness of each treatment using the following formula, keeping the results to two decimal places.
[204] Egg hatching rate (%) = Number of hatched eggs / Total number of eggs treated * 100
[205] Control effectiveness (%) = (Egg hatching rate in the control zone / Egg hatching rate in the treated zone) / Egg hatching rate in the control zone) * 100
[206] 2. The result of the experiment
[207] The results of the experiment are shown in Table 8. The compounds 1-(S,S), 1-(R,R), 1'-(S,R) 1'-(R,S), S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated good inhibitory activity on the hatching of Spodoptera litura eggs at a concentration of 500 ppm. Table 8 Treatment: Basic number of eggs before treatment; Number of larvae hatched 4 days after treatment; Hatching rate (%) Petition 870250038759, dated 05 / 13 / 2025, pp. 184 / 208 / 61 Repetition 1 Repetition 2 Repetition 3 Repetition 1 Repetition 2 Repetition 3 Repetition 1 Repetition 2 Repetition 3 Chemical compound 1 58 63 62 34 38 37 41.38 39.68 40.42 1-(S,S) 59 65 58 45 48 46 23.73 26.15 20.69 1-(S,R) 61 65 58 23 24 23 62.30 63.08 60.34 1-(R,R) 63 57 59 47 45 45 22.39 21.05 23.73 1-(R,S) 67 57 58 25 22 23 64.18 61.40 60.34 Chemical compound 1' 59 62 64 35 37 39 40.68 40.32 39.06 1'-(S,S) 62 58 56 22 21 19 64.52 63.79 66.07 1'-(S,R) 61 63 57 44 46 45 27.87 26.98 21.05 1'-(R,R) 55 56 59 21 20 22 61.82 64.29 62.71 1'-(R,S) 60 64 59 43 48 47 28.33 25.00 20.34 S-10 56 70 62 44 54 47 21.43 22.86 24.19 R-10 69 53 58 27 19 22 60.87 64.15 62.07 Chemical compound 10 63 61 57 37 36 33 41.27 40.98 42.11 S-10' 59 64 60 46 50 47 22.03 21.88 21.67 R-10' 55 58 66 21 22 24 61.82 62.07 63.64 Chemical compound 10' 64 62 59 38 36 34 40.63 41.94 42.37 Chemical compound 19 51 63 57 36 44 40 29.41 30.16 29.82 19-(S,S) 60 58 55 30 28 27 50.00 51.72 50.91 19-(S,R) 57 65 52 48 55 44 15.79 15.38 15.38 19-(R,R) 59 62 63 29 30 31 50.85 51.61 50.79 19-(R,S) 64 59 60 54 50 50 15.63 15.25 16.67 Chemical compound 19' 58 56 64 39 38 41 32.76 32.14 35.94 19'-(S,S) 57 66 53 47 53 43 17.54 19.70 18.87 19'-(S,R) 56 62 67 26 29 31 53.57 53.23 53.73 19'-(R,R) 57 59 68 47 49 55 17.54 16.95 19.12 19'-(R,S) 61 65 54 30 32 27 51.67 50.77 50.00 Comparison of solvents 58 61 63 54 57 58 92.87 Clear water 57 62 59 55 60 56 96.06 Example of Experiment 7: Effect 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', S10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19' Petition 870250038759, dated 05 / 13 / 2025, page. 185 / 208 / 61 (S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' in the hatching of Harmonia axyridis eggs.
[208] 1. Experiment solution
[209] Harmonia axyridis egg cards (containing approximately 20 eggs per card) were purchased from Jiyuan Baiyun Industrial Co., Ltd., Henan Province. The number of eggs in the cards was counted as the baseline before treatment. Five egg cards constitute one treatment, and each treatment is performed with three replicates. The egg cards were immersed in a 100 ppm pesticide solution for 30 seconds, removed, dried, and then cultured under humid conditions. Place the treated mite eggs and leaf discs at 27°C for culture. After 4 days of treatment, begin investigating the hatching of Harmonia axyridis eggs. Calculate the control efficacy using the following formulas.
[210] Egg hatching rate (%) = Number of hatched eggs / Total number of eggs treated * 100
[211] Control effectiveness (%) = (Egg hatching rate in the control zone / Egg hatching rate in the treated zone) / Egg hatching rate in the control zone) * 100
[212] 2. The result of the experiment
[213] The results presented in Table 9. Compounds 1-(S,S), 1-(R,R), 1'-(S,R), 1'-(R,S), as well as compounds 1 and 1', S-10, R-10, S-10', R-10', 10, 10', 19(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated a strong inhibitory activity on the hatching of Harmonia axyridis eggs. Table 9 Treatment Basic number of eggs before treatment Number of larvae hatched 4 days after treatment Hatching rate (%) Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Replicate 1 Replicate 2 Replicate 3 Chemical compound 1 112 94 99 7 6 6 6.25 6.38 6.06 1-(S,S) 106 88 93 0 0 0 0.00 0.00 0.00 Petition 870250038759, dated 05 / 13 / 2025, pages 186 / 208 / 61 1-(S,R) 108 99 102 13 14 14 12.04 14.14 13.73 1-(R,R) 92 110 101 0 0 0 0.00 0.00 0.00 1-(R,S) 111 88 95 11 9 10 9.91 10.23 10.53 Chemical compound 1' 102 96 106 6 4 7 5.88 4.17 6.60 1'-(S,S) 92 98 107 18 19 21 19.57 19.39 18.69 1'-(S,R) 101 105 94 0 0 0 0.00 0.00 0.00 1'-(R,R) 88 95 111 15 16 18 17.05 16.84 16.22 1'-(R,S) 93 87 109 0 0 0 0.00 0.00 0.00 S-10 112 98 136 0 0 0 0.00 0.00 0.00 R-10 125 84 101 15 10 13 12.00 11.90 12.87 Chemical compound 10 99 78 126 4 3 7 4.04 3.85 5.56 S-10' 94 107 116 0 0 0 0.00 0.00 0.00 R-10' 133 102 94 17 14 12 12.78 13.73 12.77 Chemical compound 10' 87 95 122 5 5 6 5.75 5.26 4.92 Chemical compound 19 92 110 96 3 5 4 3.26 4.45 4.17 19-(S,S) 95 103 104 13 15 16 13.68 14.56 15.38 19-(S,R) 107 100 98 0 0 0 0.00 0.00 0.00 19-(R,R) 97 104 102 14 15 14 14.43 14.42 13.73 19-(R,S) 102 105 98 0 0 0 0.00 0.00 0.00 Chemical compound 19' 89 96 108 4 5 7 4.49 5.21 6.48 19'-(S,S) 95 97 103 0 0 0 0.00 0.00 0.00 19'-(S,R) 96 107 112 10 10 11 10.42 9.35 9.82 19'-(R,R) 112 104 94 0 0 0 0.00 0.00 0.00 19'-(R,S) 107 95 92 11 10 9 10.28 10.53 9.78 Comparison of solvents 89 112 91 86 107 87 95.92 Clear water 95 107 104 92 104 100 96.73. Example of Experiment 8: Initial screening effect of the fungicidal activity (against the rice blast pathogen) 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, compound 1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19'
[214] 1. Experiment solution
[215] Experimental Materials: Culture medium, activated microorganisms, Petition 870250038759, dated 05 / 13 / 2025, pp. 187 / 208 / 61 sterilized water, 96-well plates and multichannel pipette.
[216] Rapid Screening System (200 μL): Culture medium (150 μL) + Pesticide (40 μL) + Microorganisms (10 μL).
[217] Experiment Steps: Pesticide preparation, addition of culture medium and pesticide, preparation of microorganism suspension and detection
[218] (1) Pesticide preparation: Prepare the pesticide with a final concentration of 100 ppm. Transfer the pesticide solution to 1.5 mL centrifuge tubes for later use.
[219] (2) Use a multichannel pipette to add the culture medium and pesticide to the 96-well plate.
[220] (3) Preparation of the Microorganism Suspension: Remove a Petri dish with Add 15 mL of sterile water to the Petri dish. Use a pipette tip to slide over the surface of the mycelia, causing the mycelia to break and dissolve in the sterile water. Remove 10 μL of the mycelial suspension and observe under a microscope to ensure that there are at least 10 mycelia in the field of view. For bacterial cultures with OD600 = 1.0, dilute 1000 times to obtain the inoculation suspension; for oomycetes oocysts, ensure a minimum concentration of 1x10⁵ / mL. Pyricularia oryzae culture (fungus causing rice blast),
[221] (4) Detection: Measure the DO (optical absorbance) of fungi at 450 nm and bacteria at 600 nm, recording the initial data as 0 hours. After a period of cultivation, record the growth data and calculate the growth inhibition rate using the following formula:
[222] Inhibition rate (%) = ((OD control (72h)-OD control (0h))-(OD treatment (72h)-OD treatment (0h)) / (OD control (72h)-OD control (0h))x100
[223] 2. The result of the experiment
[224] The results of the experiment are presented in Table 10. 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), as well as compounds 1,1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' demonstrated a significant inhibition rate against the rice explosion fungus (Pyricularia oryzae) a Petition 870250038759, dated 05 / 13 / 2025, p. 188 / 208 / 61 at a concentration of 100 ppm. In particular, compounds 1-(S,S), 1-(R,R), 1'-(R,S), 1'-(S,R), compound 1, 1', S-10, R-10, S-10', R-10', 10, 10', 19-(S,S), 19-(S,R), 19-(R,R), 19-(R,S), 19'-(S,S), 19'-(S,R), 19'-(R,R), 19'-(R,S), 19 and 19' showed an inhibition rate greater than 90%. Table 10 Code Rice blast inhibition rate (%) Average inhibition rate (%) Repetition 1 Repetition 2 Repetition 3 Chemical compound 1 96.34 95.11 94.82 95.42 1-(S,S) 99.38 95.02 97.64 97.35 1-(S,R) 87.32 82.96 78.48 82.92 1-(R,R) 99.41 99.12 98.34 98.96 1-(R,S) 75.86 83.08 86.80 81.91 Chemical compound 1' 95.78 98.76 88.30 94.28 1'-(S,S) 84.82 83.06 76.44 81.44 1'-(S,R) 95.80 102.01 99.85 99.22 1'-(R,R) 84.82 83.06 86.71 84.86 1'-(R,S) 100.26 99.74 100.26 100.09 S-10 98.63 99.72 97.51 98.62 R-10 81.97 83.68 81.92 82.52 Chemical compound 10 93.89 94.52 94.36 94.26 S-10' 100.03 99.64 98.27 99.31 R-10' 82.71 81.95 83.14 82.60 Chemical compound 10' 94.01 95.16 93.77 94.31 Chemical compound 19 97.23 95.14 94.35 95.57 19-(S,S) 86.52 83.17 84.38 84.69 19-(S,R) 100.10 99.34 99.87 99.77 19-(R,R) 81.29 83.56 83.45 82.77 19-(R,S) 99.73 100.15 100.24 100.04 Chemical compound 19' 91.33 93.48 92.95 92.59 19'-(S,S) 97.41 96.58 97.29 97.09 19'-(S,R) 86.44 85.97 86.28 86.23 19'-(R,R) 96.97 97.35 97.26 97,19 19'-(R,S) 85.69 86.41 86.27 86.12, Example Experiment 9: Effect of sulfonate ester compounds on Petition 870250038759, dated 05 / 13 / 2025, pp. 189 / 208 / 61 hatching of Tetranychus cinnabarinus (red mite) eggs
[225] 1. Experimental Method
[226] This experiment adopts the method described in the technical section of Example Experiment 1, using mainly the leaf disc method to explore the effect of compounds 1 to 30 and compounds 1' to 30' on the hatching of Panonychus citri (orange mite) eggs. The concentration of the chemical compound is 100 ppm.
[227] 2. The result of the experiment
[228] The results of the experiment are presented in Table 11. The egg hatching rates for chemical compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 1', 2', 3', 4', 5', 6', 7', 8' and 9' were all below 15%, demonstrating good acaricidal activity against mite eggs. Table 11 Treatment | Basic number of eggs before treatment | Number of unhatched eggs 7 days after treatment | Hatching rate (%) | Replicate 1 | Replicate 2 | Replicate 3 | Replicate 1 | Replicate 2 | Replicate 3 | Replicate 1 | Replicate 2 | Replicate 3 | Chemical compound 1 | 142 | 95 | 107 | 142 | 95 | 107 | 0.00 | 0.00 | 0.00 | Chemical compound 2 | 133 | 88 | 103 | 132 | 87 | 101 | 0.76 | 1.14 | 1.94 | Chemical compound 3 | 116 | 78 | 108 | 105 | 67 | 99 | 9.48 | 14.10 | 8.33 | Chemical compound 4 | 87 | 137 | 112 | 99 | 127 | 106 | 8.05 | 7.30 Chemical compound 5 82 126 93 75 113 83 8.54 10.32 10.75 Chemical compound 6 98 134 102 84 115 89 14.29 14.18 12.75 Chemical compound 7 102 135 87 94 124 81 7.84 8.15 6.90 Chemical compound 8 96 118 133 83 107 121 13.54 9.32 9.02 Chemical compound 9 108 112 89 93 96 76 13.89 14.29 14.61 Chemical compound 10 121 89 104 121 89 104 0.00 0.00 0.00 Petition 870250038759, dated 05 / 13 / 2025, pages 190 / 208 / 61 Quupoll compound 134 98 122 132 97 121 1.49 1.02 0.82 Quupoll compound12 123 79 136 112 71 124 8.94 10.13 8.82 Quupoll compound13 92 113 144 87 105 136 5.43 7.08 5.56 Quiuup compound14 78 107 141 71 99 128 8.97 7.48 9.22 Quiuup compound15 94 123 111 82 106 95 12.77 13.82 14.41 Quiuupo compound16 111 135 92 103 124 85 7.21 8.15 7.61 Chemical compound 17 99 128 133 86 115 121 13.13 10.16 9.02 Chemical compound 18 112 141 89 98 122 76 12.50 13.48 14.61 Chemical compound 19 122 92 98 122 92 98 0.00 0.00 0.00 Chemical compound 20 78 86 105 71 77 95 8.97 10.47 9.52 Chemical compound 21 93 106 99 81 91 85 12.90 14.15 14.14 Chemical compound 22 114 105 127 114 105 127 0.00 0.00 0.00 Chemical compound 23 92 109 111 87 103 105 5.43 5.50 5.41 Chemical compound 24 89 97 122 84 91 113 5.62 6.19 7.38 Chemical compound 25 103 98 135 103 98 135 0.00 0.00 0.00 Chemical compound 26 117 86 92 109 79 84 6.84 8.14 8.70 Chemical compound 27 125 92 107 110 80 94 12.00 13.04 12.14 Chemical compound 28 129 104 93 129 104 93 0.00 0.00 0.00 Chemical compound 29 133 84 115 126 79 108 5.26 5.95 6.09 Chemical compound 30 87 116 127 76 101 110 12.64 12.93 13.39 Chemical compound 1' 138 86 112 138 86 112 0.00 0.00 0.00 Chemical compound 2' 89 132 111 89 130 110 0.00 1.52 0.90 Compound 123 129 76 112 117 68 8.94 9.30 10.53. Petition 870250038759, dated 05 / 13 / 2025, pages 191 / 208 / 61 Chemical Compound 3' Chemical Compound 4' 141 110 92 126 101 86 10.64 8.18 6.52 Chemical Compound 5' 84 98 133 76 88 119 9.52 10.20 10.53 Chemical Compound 6' 108 136 97 93 117 84 13.89 13.97 13.40 Chemical Compound 7' 115 107 144 106 98 134 7.83 8.41 6.94 Chemical Compound 8' 78 97 128 70 88 115 10.26 9.28 10.16 Chemical Compound 9' 92 115 132 79 98 112 14.13 14.78 15.15 Chemical compound 10' 95 126 142 95 126 142 0.00 0.00 0.00 Chemical compound 11' 87 123 111 87 121 110 0.00 1.63 0.90 Chemical compound 12' 113 131 77 103 119 69 8.85 9.16 10.39 Chemical compound 13' 131 100 95 117 92 86 10.69 8.00 9.47 Chemical compound 14' 92 107 137 83 96 123 9.78 10.28 10.22 Chemical compound 15' 118 136 95 112 117 82 13.55 13.97 13.68 Chemical compound 16' 122 131 114 112 119 103 8.20 9.16 9.65 Chemical compound 17' 79 99 128 70 90 115 11.39 9.09 10.16 Chemical compound 18' 93 115 141 80 98 122 13.98 14.78 13.48 Chemical compound 19' 108 119 91 108 119 91 0.00 0.00 0.00 Chemical compound 20' 140 106 83 127 97 76 9.29 8.49 8.43 Chemical compound21' 88 95 114 77 83 100 12.50 12.63 12.28 Comparison of solvents 94 85 106 6 2 8 94.57 Clear water 81 121 93 5 6 3 95.21 Example 10
[229] A mixture of ginger and galangal was prepared with a ratio of 7:3 between ginger extract and galangal volatile oil, and a Petition 870250038759, dated 05 / 13 / 2025, pp. 192 / 208 / 61 combined formulation with compounds 1, 10 and 19. Based on the test method of example 1, the leaf disc method was used to evaluate the control effect on Tetranychus cinnabarinus eggs.
[230] The ginger extract was obtained by extraction with a mixed solvent of ethyl acetate and ethanol in a 1:4 ratio.
[231] Bliss, based on the concept of independent combined action that he proposed, considers that the theoretical mortality rate P, when using an insecticide or acaricide in combination, can be calculated by the following formula:
[232] P = Pm+Pn(1-Pm)
[233] Pm is the target mortality rate when the first active component is used at concentration m (%); Pn is the target mortality rate when the second active component is used at concentration n (%).
[234] If the actual mortality rate of the target, after mixing the two active components at certain concentrations, is greater than the theoretical mortality rate P, then the mixture of the two active components, at the established concentrations, is considered to have a synergistic effect. Otherwise, there is an antagonistic effect.
[235] The experimental results are shown in Table 12. Compounds 1, 10 and 19, combined with the ginger and galangal mixture, show a synergistic effect in controlling Tetranychus cinnabarinus eggs. Table 12 Code Treatment Concentration (mg / L) Efficacy of Tetranychus cinnabarinus egg control (%) Theoretical efficacy (%) Synergistic effect 1 Mixture of Zingiber officinale and Kaempferia galanga (T1) 500 35.38 / / 2 200 15.24 / / 3 Chemical compound 1 (T2) 0.3 52.19 / / 4 0.2 33.58 / / Petition 870250038759, dated 05 / 13 / 2025, pages 193 / 208 / 61 5 0.1 17.12 / / 6 Chemical compound 10(T3) 0.5 68.12 / / 7 0.2 20.79 / / 8 0.1 11.45 / / 9 Chemical compound 19(T4) 0.25 48.73 / / 10 0.2 36.14 / / 11 0.1 20.57 / / 12 T1:T2=500:0.3 500+0.3 76.21 69.11 Yes 13 T1:T2=500:0.2 500+0.2 65.84 57.08 Yes 14 T1:T2=500:0.1 500+0.1 52.11 46.44 Yes 15 T1:T2=200:0.3 200+0.3 67.83 59.48 Yes 16 T1:T2=200:0.2 200+0.2 51.26 43.70 Yes 17 T1:T2=200:0.1 200+0.1 40.32 29.75 Yes 18 T1:T3=500:0.5 500+0.5 85.74 79.40 Yes 19 T1:T3=500:0.2 500+0.2 54.26 48.81 Yes 20 T1:T3=500:0.1 500+0.1 48.15 42.78 Yes 21 T1:T3=200:0.5 200+0.5 79.06 72.98 Yes 22 T1:T3=200:0.2 200+0.2 40.18 32.86 Yes 23 T1:T3=200:0.1 200+0.1 30.64 24.95 Yes 24 T1:T4=500:0.25 500+0.25 73.12 66.87 Yes 25 T1:T4=500:0.2 500+0.2 65.03 58.73 Yes 26 T1:T4=500:0.1 500+0.1 52.44 48.67 Yes 27 T1:T4=200:0.25 200+0.25 61.52 56.54 Yes 28 T1:T4=200:0.2 200+0.2 50.19 45.87 Yes 29 T1:T4=200:0.1 200+0.1 40.01 32.68 Yes
[236] The examples mentioned above serve only to illustrate the Petition 870250038759, dated 05 / 13 / 2025, p. 194 / 208 / 61. The principle and benefits of the present invention should not be used to restrict it. Anyone familiar with the art may modify or alter the examples mentioned above without violating the spirit and scope of the present invention. Therefore, all equivalent modifications and alterations made by someone with common technical knowledge in the field, without deviating from the spirit and technical ideas disclosed by the present invention, should still be covered by the claims of the present invention. Petition 870250038759, dated 05 / 13 / 2025, pp. 195 / 208
Claims
1 / 6 CLAIMS 1) SULFONATE COMPOUNDS characterized by structure conforming to formula (A) or its mesomers, racemes, stereoisomeric isomers and pharmaceutically acceptable salts: OR ' / ^4 R p rro o 2 XjJ r3 r4' Ri (A) Where: R1 and R2 are independently selected from hydrogen, halogen, substituted or unsubstituted C1-C1 alkyl, substituted or unsubstituted C1-C1 alkyl, C2-C1 alkyl carbonyl, C2-C1 alkyl carbonyl and C1-C1 alkyl carbonyl; R3, R4, and R4 are independently selected from hydrogen and C1-C5 alkyl, C1-C5 alkenyl; or, R3, R3', R4, R4' and the C to which they are attached form a five-membered cycloalkyl heterocyclic; Rs is selected from either halogen or substituted or unsubstituted C1-C10 alkyl. 2) SULFONATE COMPOUNDS according to claim 1, or their mesomers, racemes, stereoisomeric isomers and pharmaceutically acceptable salts, characterized in that the C1-C5 alkyl group is selected from methyl and ethyl; the C1-C5 alkyn group is selected from vinyl; the five-membered cycloalkanyl heterocyclic group is selected from ^0^. 3) SULFONATE COMPOUNDS according to claim 1, the sulfite compound or its mesomer, racemic, stereoisomeric isomer, acceptable pharmaceutical salt, characterized in that the compound's structure is selected from one of the following: Petition 870250038759, dated 05 / 13 / 2025, pp. 197 / 208 2 / 6 4) SULFONATE COMPOUNDS according to claim 1, sulfonate compounds or their mesomers, racemic compounds, stereoisomeric isomers and pharmaceutically acceptable salts, characterized in that group R5 is selected from ethyl fluorinated, ethyl brominated, ethyl dorado, ethyl 2,2-difluorinated and ethyl 2,2-dichlorinated; R1 and R2 are independently selected from H, F, Cl, Br; 5) SULFONATE COMPOUNDS according to claim 1, sulfonate compounds or their mesomers, racemic, stereoisomeric isomers and pharmaceutically acceptable salts, characterized in that R5 is -CH2CH2F; R1 > R2 is Cl. 6) SULFONATE COMPOUNDS according to claim 1, sulfonate compounds or their mesomers, racemic, stereoisomeric isomers and pharmaceutically acceptable salts, characterized by the compound being selected from the following compounds: Petition 870250038759, dated 13 / 05 / 2025, pp. 198 / 208 3 / 6 ο Cl θ' ο 18' Petition 870250038759, dated 13 / 05 / 2025, pp. 199 / 208 4 / 6 7) METHOD FOR CONTROLLING AND / OR KILLING INSECT EGGS OR FUNGICIDE, characterized by the use of a compound according to any of claims 1 to 6 applied to pest eggs and / or fungi. 8) METHOD FOR CONTROLLING AND / OR KILLING INSECT EGGS OR FUNGICIDE according to claim 7, characterized by the compound being selected from one of the following compounds or a mixture of two or more: Petition 870250038759, dated 05 / 13 / 2025, page 200 / 208 5 / 6 O ol 19' 9) METHOD FOR CONTROLLING AND / OR KILLING INSECT EGGS OR FUNGICIDE according to claim 7, characterized by pest eggs being produced by insects of the orders Thysanoptera, Hemiptera, Lepidoptera, Coleoptera, Arachnoidea, arachnids of the families Tetranychidae, Tarsonemidae, Eriophyidae, Tenuipalpidae, Phytoseiidae, Ascidae or Prostigmata; and fungi including fungi and bacteria. 10) METHOD FOR CONTROL AND / OR DEATH OF INSECT EGGS OR FUNGICIDE according to claim 7, characterized in that said pests are selected from Frankliniella intonsa, Thrips tabaci Lindeman, Taeniothrips distalis Karn, Stenchaeotothrips biformis, Thrips hawaiiensis Morgan, Thrips palmi Karny, Frankliniella occidentalis, Thrips japonicus Bagnall, Thrips serratus Kobus, Frankliniella tenuicornis Uzel, Scirtothrips dorsalis Hood, Heliothrips haemorrhoidalis Bouche, Scirtothrips dorsalis Hood, Scolothrips sexmaculatus Pergande, Cnaphalocrocis medinalis, Spodoptera exigua, Spodoptera litura, Carposina sasakii, Helicoverpa armigera, Plutella xylostella, Diaphania indica, Maruca testulalis Geyer, Bemisia tabaci Gennadius, Trialeurodes vaporariorum, Aleurocanthus spiniferus, Dialeurodes citri Ashm, Bemisia myricae Kuwana, Aleurocybotus indicus, Aleurodicus dispersus, Oligonychus baipisongis, Oligonychus karamatus, Oligonychus rubicundus, Cerambycidae, Coccinellidae,Lampyridae, Scarabaeidae, Mylabris phalerata, Allomyrina dichotoma, Buprestidae, Melyridae, Scarabaeidae, Lucanidae, Elateridae, Dytiscidae, Sitophilus oryzae, Harmonia axyridis, Eotetranychus albus, Eotetranychus Petition 870250038759, of 05 / 13 / 2025, p. 201 / 208 6 / 6 bailae, Eotetranychus camelliae, Tetranychus neocaledonicus, Tetranychus phaselus, Tetranychus urticae, Tetranychus cinnabarinus, Schizotetranychus baltazarae, Schizotetranychus bambusae, Schizotetranychus elongatus, Mixonychus (Bakerina) aestiva, Mixonychus (Mixonychus) ganjuis, Panonychus citri, Panonychus caglei, Allonychus bambusae, Allonychus wuyinicus, Stigmaeopsis celarius, Mononychellus georgicus, Acanthonychus jiangfengensis, Amphitetranychus viennensis; The bacterium in question is the causal agent of rice blast., 11) “METHOD FOR CONTROLLING AND / OR KILLING INSECT EGGS OR FUNGICIDE” according to claim 7, characterized in that the concentration of the sulfonate compound applied is at least 0.1 ppm. 12) “METHOD FOR CONTROLLING AND / OR KILLING INSECT EGGS OR FUNGICIDE” according to claim 7, characterized by including one or more adjuvants such as dispersants, wetting agents, binders, emulsifiers, stabilizers and solvents. 13) “METHOD” according to claim 12 characterized in that the pharmaceutical form of the product is an emulsion, suspension, wettable powder, powder, granule, solution, broth or mother powder. 14) “PESTICIDE COMPOUND”, characterized by containing the compound of formula (I) as the active substance. 15) “PESTICIDE COMPOUND” according to claim 14, characterized by comprising a mixture of a Zingiber officinale rhizome extract and a Kaempferia rhizome extract, the Zingiber officinale rhizome extract: Kaempferia rhizome extract = 7:3, wherein the ginger rhizome extract is Zingiber officinale rhizome extracted with ethanol: ethyl acetate = 1~4:1; said Kaempferia rhizome extract is the volatile oil of Kaempferia rhizome. Petition 870250038759, dated 05 / 13 / 2025, pp. 202 / 208