CN114773328A - Oxadiazole-containing thioether and sulfone compound, stereoisomer thereof, salt thereof or solvate thereof, preparation method, composition and application - Google Patents

Oxadiazole-containing thioether and sulfone compound, stereoisomer thereof, salt thereof or solvate thereof, preparation method, composition and application Download PDF

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CN114773328A
CN114773328A CN202210613076.6A CN202210613076A CN114773328A CN 114773328 A CN114773328 A CN 114773328A CN 202210613076 A CN202210613076 A CN 202210613076A CN 114773328 A CN114773328 A CN 114773328A
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oxadiazole
salt
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杨松
王方
刘洪武
吴志兵
柳立伟
周翔
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Guizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G13/00—Protecting plants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

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Abstract

The invention discloses a compound containing oxadiazole thioether and sulfone, a stereoisomer, a salt or a solvate thereof, a preparation method, a composition and application, wherein the compound has a general formula structure as follows:

Description

Oxadiazole-containing thioether and sulfone compound, stereoisomer thereof, salt thereof or solvate thereof, preparation method, composition and application
Technical Field
The invention relates to the technical field of pharmaceutical chemistry, in particular to a compound containing oxadiazole thioether and sulfone, a stereoisomer thereof, a salt thereof or a solvate thereof, a preparation method, a composition and application thereof.
Background
In recent years, plant fungi and bacteria seriously affect the yield and quality of global crops, and plant fungal diseases directly cause the yield reduction and the quality reduction of the crops, thereby bringing huge economic loss to farmers. For example, rice is one of the most important crops in China, and provides a food source for more than half of the population. The rice bacterial blight is one of the most destructive bacterial diseases of rice, and has a great negative effect on the yield of economic crops. Wherein, the agricultural loss caused by bacterial diseases such as rice bacterial blight, citrus canker pathogen, kiwi canker pathogen and the like reaches hundreds of millions of dollars every year. At present, the long-term use of traditional bactericides such as bismerthiazol and thiacetone not only has poor control effect, but also increases the drug resistance of pathogens. Therefore, the development of an agricultural fungicide having high efficiency and safety is urgently required.
Oxadiazole derivatives have been reported in the literature to exhibit a broad spectrum of biological activities, such as: antibacterial, antifungal, insecticidal, herbicidal, plant growth regulating, antitumor, and antiinflammatory etc. According to the earlier work of the center, the oxadiazole compound shows better anti-plant pathogen activity. The nitrogen-containing heterocyclic compounds have the characteristics of structural diversity and biological activity diversity, and attract extensive attention in the fields of medicinal chemistry, pesticide chemistry and organic chemistry. On the other hand, molecules containing sulfone skeletons show biological activities such as sterilization, disinsection, antivirus and the like.
Disclosure of Invention
In order to search for an efficient bactericidal active compound, the invention takes an oxadiazole structure as a connecting chain, synthesizes a series of oxadiazole sulfone compounds with novel structures, tests the biological activity of the oxadiazole sulfone compounds, and provides an important scientific basis for research, development and creation of new pesticides.
The invention provides a compound containing oxadiazole thioether and sulfone, a stereoisomer, a salt or a solvate thereof, wherein the compound has a general structure as follows:
Figure BDA0003672559900000021
the general structure of the intermediate compound for preparing the compound containing oxadiazole thioether and sulfone, the stereoisomer thereof, the salt thereof or the solvate thereof is as follows:
Figure BDA0003672559900000022
wherein,
each R is independently selected from one or more of hydrogen, optionally substituted or unsubstituted alkyl, amino, ester, hydrazino, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkoxy, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted heteroaryl, optionally substituted or unsubstituted benzyl, optionally substituted or unsubstituted alpha-methyl-benzyl; or R1And R2Are connected to form an optionally substituted 5-to 10-membered ring or a ring containing heteroatoms, said heteroatoms being one or more of N, O, S;
preferably, R is independently one or more selected from hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy, C5-C10 aryl and C5-C10 heteroaryl;
preferably, each R is independently selected from hydrogen
Figure BDA0003672559900000023
Figure BDA0003672559900000024
Preferably, the intermediate compound and the target compound are each selected from the following compounds:
Figure BDA0003672559900000025
Figure BDA0003672559900000031
the second purpose of the invention is to provide a preparation method of oxadiazole-containing thioether and sulfone compounds, stereoisomers thereof, salts thereof or solvates thereof, which comprises the following steps:
Figure BDA0003672559900000032
the preparation method comprises the following steps:
step 1: preparation of intermediate pyran-4-carboxylic acid methyl ester
Pyran-4-carboxylic acid (44.0mmol) and H2SO4(2.5mL) and CH3OH (50mL) was added to a 100mL round-bottomed flask and heated at 80 ℃ under reflux for 2.5 h. The reaction is terminated and the excess CH is removed by vacuum distillation3OH, extracted with ethyl acetate (100mL), washed with water (2X 50mL), over anhydrous Na2SO4Drying, desolventizing, and performing column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a white oil in 88.8% yield.
And 2, step: preparation of intermediate pyran-4-yl hydrazine
In a 25mL single neck round bottom flask, pyran-4-carboxylic acid methyl ester (14.0mmol), 3mL hydrazine hydrate, and 2mL CH were added3OH, and reacting at room temperature for 20 hours. Removal of excess CH by vacuum distillation3OH, extracted with ethyl acetate (50mL), washed with water (2X 20mL), over anhydrous Na2SO4Drying, desolventizing, and performing column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a white oil in 59.7% yield.
And 3, step 3: preparation of intermediate 5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole-2-thiol
In a 50mL three-necked round-bottomed flask, intermediate pyran-4-carbonyl hydrazine (3.30mmol) and KOH (6.6mmol) were added, and the mixture was dissolved in 30mL of ethanol. After stirring for 10min, 8.2mmol of CS2 were addedReaction at 85 ℃ for 1d, then quench with water (20mL) and CH2Cl2V/V (50mL) gave a white solid in 49.2% yield.
And 4, step 4: preparation of target compound 2- (methylthio) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole
5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole-2-thiol (3.3mmol), KOH (6mL) and DMF (10mL) were added to a 25mL round-bottomed flask, reacted at room temperature for 6H, desolventized, and column Chromatographed (CH)2Cl2:CH3OH 50:1, V/V) to give a white solid in 46.8% yield.
And 5: preparation of target compound 2- (methylsulfonyl) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole
In a 30mL single neck round bottom flask, 0.19mmol of ammonium molybdate was dissolved in 30% hydrogen peroxide, stirred in ice bath for 10min, and then 2- (methylthio) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole (1.1mmol) in ethanol (2mL) was added dropwise and reacted at room temperature for 8H. Water (20mL) and ethyl acetate (50 mL). Desolventizing and column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a yellow solid in 43.5% yield.
A third object of the present invention is to provide a composition comprising: the compound containing oxadiazole thioether and sulfone, stereoisomer thereof, salt thereof or solvate thereof, and agriculturally usable auxiliary agents, bactericides, insecticides or herbicides.
Preferably, the formulation of the composition is selected from Emulsifiable Concentrate (EC), Dust (DP), Wettable Powder (WP), Granules (GR), Aqueous Solution (AS), Suspension Concentrate (SC), ultra low volume spray (ULV), Soluble Powder (SP), Microcapsules (MC), smoke (FU), aqueous Emulsion (EW), water dispersible granules (WG).
The fourth purpose of the invention is to provide the application of the oxadiazole-containing thioether and sulfone compound, the stereoisomer thereof, the salt thereof or the solvate thereof, or the composition in controlling agricultural pests or protecting plants from the agricultural pests; wherein the agricultural pest comprises: plant leaf blight and plant canker, wherein the agricultural plant diseases and insect pests are rice bacterial leaf blight, tobacco bacterial wilt, cucumber bacterial leaf blight, konjak bacterial leaf blight, citrus canker, kiwi canker, grape canker, tomato canker, apple canker, cucumber botrytis cinerea, pepper fusarium wilt pathogen, sclerotinia sclerotiorum, wheat fusarium graminearum and potato late blight.
A fifth object of the present invention is to provide a method for controlling agricultural pests, comprising: the compound containing oxadiazole thioether and sulfone, its stereoisomer, its salt or its solvate, or the composition is made to act on harmful substances or their living environment.
A sixth object of the present invention is to provide a method for protecting a plant from an agricultural pest, comprising: a method step of contacting the above oxadiazole-containing thioether and sulfone compounds, their stereoisomers, salts or solvates thereof, or the above composition.
Further, the relevant description is as follows:
the term "substituted" as used herein means that any one or more hydrogen atoms on the designated atom or group is replaced with the designated group of choice, provided that the general valence of the designated atom is not exceeded. Substituents are named to the central structure if not otherwise stated. For example, it is understood that when (cycloalkyl) alkyl is a possible substituent, the point of attachment of the substituent to the central structure is in the alkyl moiety. As used herein, a cyclic double bond is a double bond formed between two adjacent ring atoms (e.g., C-C, C-N or N-N). When referring to substitution, especially polysubstitution, it is meant that the multiple substituents are substituted at various positions on the indicated radical, e.g., dichlorobenzyl means 2, 3-dichlorobenzyl, 2, 4-dichlorobenzyl, 2, 5-dichlorobenzyl, 2, 6-dichlorobenzyl, 3, 4-dichlorobenzyl and 3, 5-dichlorobenzyl.
Combinations of substituents and variables are permissible only if such combinations result in stable compounds or useful synthetic intermediates. A stable compound or stable structure implies that the compound is sufficiently stable to be isolated in useful purity from the reaction mixture and subsequently formulated to form an effective therapeutic agent.
The term "heteroaryl" refers to substituted and unsubstituted aromatic 5 or 6 membered monocyclic groups, 9-or 10-membered bicyclic groups, and 11 to 14 membered tricyclic groups having at least one heteroatom (O, S or N) in at least one ring, said heteroatom containing ring preferably having 1, 2 or 3 heteroatoms selected from O, S and N. The heteroatom-containing heteroaryl groups can contain one or two oxygen or sulfur atoms per ring and/or from 1 to 4 nitrogen atoms, provided that the total number of heteroatoms in each ring is 4 or less and each ring has at least one carbon atom. The fused rings completing the bicyclic and tricyclic groups may contain only carbon atoms and may be saturated, partially saturated, or unsaturated. The nitrogen may optionally be oxidized and quaternized. Bicyclic or tricyclic heteroaryl groups must include at least one fully aromatic ring, and the other fused rings may be aromatic or non-aromatic. The heteroaryl group may be attached at any available nitrogen or carbon atom of any ring.
Exemplary monocyclic heteroaryl groups include pyrrolyl, pyrazolyl, pyrazolinyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, furanyl, thienyl, oxadiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, and the like.
Exemplary bicyclic heteroaryls include indolyl, benzothiazolyl, benzodioxolyl, benzoxazolyl, benzothienyl, quinolinyl, tetrahydroisoquinolinyl, isoquinolinyl, benzimidazolyl, benzofuranyl, indolizinyl, benzofuranyl, chromonyl, coumarinyl, benzofuranyl, cinnolinyl, quinoxalinyl, indazolyl, pyrrolopyridyl, fluoropyridinyl, dihydroisoindolyl, tetrahydroquinolinyl, and the like.
The compounds of the invention are understood to include the free form and salts thereof, unless otherwise indicated. The term "salt" means an acid and/or base salt formed from an inorganic and/or organic acid and a base. In addition, the term "salt" may include zwitterions (inner salts), such as when the compound of formula I contains a basic moiety, such as an amine or pyridine or imidazole ring, and an acidic moiety, such as a carboxylic acid. Pharmaceutically acceptable (i.e., non-toxic, physiologically acceptable) salts are preferred, such as acceptable metal and amine salts, wherein the cation does not contribute significantly to the toxicity or biological activity of the salt. However, other salts may be useful, such as separation or purification steps in the preparation process, and are therefore included within the scope of the present invention.
Preferably, C1-C10Alkyl refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, and isomers thereof; c2-C5Alkenyl refers to ethenyl, propenyl, allyl, butenyl, pentenyl, and isomers thereof.
When reference is made to substituents being alkenyl, alkyl, aryl, benzyl, cycloalkyl, or where these substituents are specifically one to three of the above substituents being alkenyl, alkyl, aryl, benzyl, cycloalkyl in particular. For example, fluorobenzyl refers to a benzyl group substituted with one to three fluorine groups.
Compared with the prior art, the invention has the beneficial effects that:
the invention takes pyranoformic acid as a starting material, introduces heterocyclic compounds into the system, synthesizes a series of oxadiazole thioether and sulfone compounds, finds that the compounds have good inhibition effect on pathogenic plant bacteria, has good inhibition effect on pathogenic bacteria such as Xanthomonas oryzae pv. oryzae, Xoo, Citrus canker (Xanthomonas axanopodus pv. citri, Xac) and Actinidia chinensis canker (Pseudomonas syringae pv. actin, Psa) and the like, and provides important scientific basis for research and development of new pesticides.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below:
example 1: preparation of intermediate methyl pyran-4-carboxylate
Pyran-4-carboxylic acid (44.0mmol) and H2SO4(2.5mL) and CH3OH (50mL) was added to a 100mL round-bottomed flask and heated at 80 ℃ under reflux for 2.5 h. The reaction is terminated and the excess CH is removed by vacuum distillation3OH, extracted with ethyl acetate (100mL), washed with water (2X 50mL), over anhydrous Na2SO4Drying, desolventizing, and performing column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a white oil in 88.8% yield.
Example 2: preparation of intermediate pyran-4-yl hydrazine
In a 25mL single neck round bottom flask, pyran-4-carboxylic acid methyl ester (14.0mmol), 3mL hydrazine hydrate, and 2mL CH were added3OH, and reacting at room temperature for 20 hours. Excess CH is removed by vacuum distillation3OH, extracted with ethyl acetate (50mL), washed with water (2X 20mL), over anhydrous Na2SO4Drying, desolventizing, and performing column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a white oil in 59.7% yield.
Example 3: preparation of intermediate 5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole-2-thiol
In a 50mL three-necked round-bottomed flask, intermediate pyran-4-carbonyl hydrazine (3.30mmol) and KOH (6.6mmol) were added, and the mixture was dissolved in 30mL of ethanol. After stirring for 10min, 8.2mmol of CS2 was added and the reaction was carried out at 85 ℃ for 1d, then quenched with water (20mL) and CH2Cl2V/V (50mL) gave a white solid in 49.2% yield.
Example 4: preparation of target compound 2- (methylthio) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole
5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole-2-thiol (3.3mmol), KOH (6mL) and DMF (10mL) were added to a 25mL round-bottomed flask, reacted at room temperature for 6H, desolventized, and column Chromatographed (CH)2Cl2:CH3OH 50:1, V/V) to give a white solid in 46.8% yield.
Example 5: preparation of target compound 2- (methylsulfonyl) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole
In a 30mL single neck round bottom flask, 0.19mmol of ammonium molybdate was dissolved in 30% hydrogen peroxide and stirred in ice bath for 10min, then 2- (methylthio) -5- (tetrahydro-2H-pyran-4-yl) -1,3, 4-oxadiazole (1.1mmol) in ethanol (2mL) was added dropwise and reacted at room temperature for 8H. Water (20mL) and ethyl acetate (50 mL). Desolventizing and column Chromatography (CH)2Cl2:CH3OH 30:1, V/V) to give a yellow solid in 43.5% yield.
Other compounds of interest were synthesized using the corresponding starting materials or substituents, according to the procedures described in the examples above.
The structure, nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the synthesized oxadiazole-containing thioether and sulfone compound are shown in table 1, and the physicochemical properties are shown in table 2.
TABLE 1 NMR Hydrogen and carbon spectra data for compounds of the present application
Figure BDA0003672559900000081
Figure BDA0003672559900000091
Figure BDA0003672559900000101
TABLE 2 physicochemical Properties of the Compounds of the present application
Figure BDA0003672559900000102
Figure BDA0003672559900000111
Pharmacological example 1:
EC50(mean effective conjugation) is an important index for evaluating the sensitivity of plant pathogenic bacteria to compounds, and is also an action mechanism of target compoundsThe concentration of the compound was an important parameter to set at the time of the study. In the concentration gradient experiment, proper 5 concentrations are set by a double dilution method, finally the inhibition rate of the medicament on plant pathogenic bacteria and the medicament concentration are converted into paired numerical values, a toxicity curve is obtained through SPSS software regression analysis, and EC is calculated50。
Testing the effective medium concentration EC of target compound on plant pathogenic bacteria by adopting turbidity method50The test subjects were rice bacterial blight (Xoo), citrus canker (Xac) and kiwi canker (Psa). DMSO was dissolved in the medium as a blank control. Putting rice bacterial blight bacteria (bacterial blight pathogenic bacteria in M210 solid culture medium) into NB culture medium, and performing shake culture in constant temperature shaking table at 28 deg.C and 180rpm to logarithmic phase for use; the citrus canker germs (on M210 solid medium) are placed into NB medium and shake-cultured in a constant temperature shaker at 28 ℃ and 180rpm until logarithmic growth phase for later use. 5mL of toxic NB liquid culture medium with different concentrations (examples: 100,50,25,12.5, 6.25. mu.g/mL) of the medicament (compound) is added into a test tube, 40. mu.L of NB liquid culture medium containing plant-pathogenic bacteria is respectively added, and the test tube is shaken in a constant temperature shaking table at 28 ℃ and 180rpm, wherein the bacterial blight pathogenic bacteria of rice are cultured for 36h, the citrus canker pathogenic bacteria are cultured for 48h, and the kiwifruit canker pathogenic bacteria are cultured for 36 h. The OD was measured on a spectrophotometer using the bacterial solutions of the respective concentrations595Value, and additionally determining the OD of the corresponding concentration of the sterilized NB-containing liquid medium595The value is obtained.
Corrected OD value-bacteria-containing medium OD value-sterile medium OD value
Percent inhibition is [ (OD value of control medium liquid OD value after correction-OD value of medium containing toxin corrected)/OD value of control medium liquid OD value after correction ] × 100
The examples of the present invention are given to illustrate the technical means of the present invention, but the contents of the examples are not limited thereto, and the experimental results of the target compounds are shown in table 3.
TABLE 3
Figure BDA0003672559900000112
Figure BDA0003672559900000121
As can be seen from Table 3, in the in vitro test, some of the compounds of interest showed good inhibitory activity against plant pathogenic bacteria (e.g., bacterial blight of rice, canker citrus and kiwifruit canker). Compound 11 has excellent inhibitory activity against rice bacterial blight, EC50 is 1.19mg L-1(ii) a Can be used for preparing pesticide for resisting plant pathogenic bacteria.
The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. An oxadiazole-containing thioether and sulfone compound, a stereoisomer, a salt or a solvate thereof, wherein the general structure of the compound is as follows:
Figure FDA0003672559890000011
wherein,
r is one or more independently selected from hydrogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl and optionally substituted or unsubstituted heteroaryl; or a plurality of R are connected to form an optionally substituted 5-10 membered ring or a ring containing heteroatoms, wherein the heteroatoms are one or more of N, O, S.
2. The oxadiazole thioether and sulfone compound, the stereoisomer thereof, the salt thereof, or the solvate thereof according to claim 1, wherein the intermediate compound for preparing the oxadiazole thioether and sulfone compound, the stereoisomer thereof, the salt thereof, or the solvate thereof has a general structure of:
Figure FDA0003672559890000012
3. the oxadiazole-containing thioether and sulfone compound of claim 1 or 2, a stereoisomer thereof, a salt thereof or a solvate thereof,
r is independently selected from one or more of hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy, C5-C10 aryl and C5-C10 heteroaryl.
4. The oxadiazole-containing thioether and sulfone compound, the stereoisomer thereof, the salt thereof or the solvate thereof according to claim 2, wherein the intermediate compound and the target compound are each selected from the group consisting of:
Figure FDA0003672559890000013
Figure FDA0003672559890000021
5. a process for preparing a compound containing oxadiazole thioether and sulfone, or a stereoisomer thereof, or a salt or solvate thereof according to any one of claims 1 to 4, which comprises the steps of:
Figure FDA0003672559890000022
6. a composition, comprising: the oxadiazole-containing thioether and sulfone compound, the stereoisomer thereof, the salt thereof or the solvate thereof according to any one of claims 1 to 4, and an agriculturally acceptable adjuvant, bactericide, insecticide or herbicide.
7. The composition of claim 6, wherein the composition is in a dosage form selected from the group consisting of Emulsifiable Concentrates (EC), Dusts (DP), Wettable Powders (WP), Granules (GR), Aqueous Solutions (AS), Suspensions (SC), ultra low volume sprays (ULV), Soluble Powders (SP), Microcapsules (MC), smoke agents (FU), aqueous Emulsions (EW), water dispersible granules (WG).
8. Use of an oxadiazole-containing thioether and sulfone compound according to any one of claims 1 to 4, a stereoisomer thereof, a salt thereof, or a solvate thereof, or a composition according to any one of claims 6 to 7 for controlling an agricultural pest or protecting a plant from an agricultural pest; wherein the agricultural pests and diseases are plant leaf blight and plant canker.
9. A method of controlling an agricultural pest, comprising: applying the oxadiazole-containing thioether and sulfone compound according to any one of claims 1 to 4, a stereoisomer thereof, a salt thereof, or a solvate thereof, or the composition according to any one of claims 6 to 7 to a harmful substance or its living environment; wherein the agricultural pests and diseases are plant leaf blight and plant canker.
10. A method for protecting a plant from an agricultural pest comprising: method step of contacting a plant with an oxadiazole containing thioether and sulfone compound according to any of claims 1-4, a stereoisomer thereof, a salt thereof or a solvate thereof, or a composition according to any of claims 6-7.
CN202210613076.6A 2022-05-31 2022-05-31 Oxadiazole-containing thioether and sulfone compound, stereoisomer thereof, salt thereof or solvate thereof, preparation method, composition and application Pending CN114773328A (en)

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