Alkenyl-substituted tellurium organic compound, preparation method and application of alkenyl-substituted tellurium organic compound in resisting phytopathogen

Abstract

The invention belongs to the field of organic synthesis and particularly relates to an alkenyl-substituted tellurium organic compound as well as a preparation method and application thereof. The alkenyl-substituted tellurium organic compound provided by the invention is prepared according to the following steps: preparing a metal rod as an anode and a carbon rod as a cathode, adding an alkenyl compound, tellurium elementary substance powder, sulfinate, an alkali reagent and an electrolyte into a mixed solvent in a protective gas atmosphere to form a reaction system, and carrying out an electrified stirring reaction to obtain the alkenyl-substituted tellurium organic compound. The target tellurium organic compound is obtained. According to the technical scheme, a new thought is provided for a synthetic methodology for preparing the alkenyl-substituted tellurium organic compound, and a novel tellurium organic lead compound is provided for creation of novel green pesticides.

Description

Technical Field

[0001] The present invention belongs to the field of organic synthesis, and particularly relates to an alkenyl-substituted tellurium organic compound, a preparation method thereof, and an application in resisting plant pathogens. Background Art

[0002] Tellurium compounds are currently widely used in many fields such as medicine, pesticides, chemistry, and materials. Scientific researchers have conducted extensive research on such compounds, their preparation methods, and applications. For example, the existing literature (P. Mampuys et al. Thiosulfonates as Emerging Reactants: Synthesis and Applications[J]. Adv.Synth. Catal . 2020, 362, 3 – 64) has reported many examples of synthesizing chalcogen organic compounds through traditional organic synthesis methods. However, the existing technology (Cristina W. Nogueira et al. Organoselenium and Organotellurium Compounds: Toxicology and Pharmacology[J]. Chem. Rev. 2004, 104, 6255−6285.) has some drawbacks, such as toxic reagents, harsh reaction conditions, and limitations on organosulfur / organoselenium precursors. Moreover, the existing technology is mostly limited to the synthesis of organosulfur / organoselenium compounds, and the preparation method of tellurium organic compounds is still not common because reagents such as metal catalysts, acids, and organolithium are likely to break the carbon-tellurium bond formed during the reaction process.

[0003] The electrochemical functionalization of alkenes represents a key approach to alkene derivatization and the construction of molecular complexity. A large amount of synthetic work is dedicated to developing and expanding the electrochemical functionalization methods of alkenes. However, there are few reports on the electrochemical functionalization of alkenes involving simple chalcogens (sulfur, selenium, or tellurium) to obtain alkenyl chalcogens. In the 21st century, the importance of organic tellurium compounds has become increasingly obvious because of their unique properties and various known and potential applications. The existing applications of tellurium in biology, materials, and medicine are becoming more and more extensive, and its chemical structure is shown as follows, such as , Moreover, two-dimensional tellurium nanosheets can be used as a novel optical material in the preparation of nonlinear optical devices. The titanium coating functionalized with tellurium nanorods has stronger antibacterial properties. Tellurium nanowires can also serve as inorganic nano-prodrugs, reacting with hydrogen peroxide in cells for good selective treatment of tumors. The redox characteristics brought about by the excellent oxygen-carrying function are one of the important reasons why elemental tellurium can participate in many organic reactions. However, there is little research on organotellurium compounds in the aspect of combating plant pathogens, especially the effects against plant pathogens (Botrytis cinerea, Rhizoctonia solani) have not been reported in the literature. Therefore, there is an urgent need to develop an organotellurium compound with good performance against plant pathogenic fungi. Selectively introducing tellurium atoms or tellurium-containing structures into organic molecules can significantly change their physical, chemical, and biological properties. Therefore, there is an urgent need to develop reaction conditions that are mild and environmentally friendly to obtain organotellurium molecules using elemental tellurium as the tellurium source, and to discover and develop small molecule alkenyl-substituted organotellurium compounds for innovative lead structures of new pesticides.

[0004] Both Botrytis cinerea and Rhizoctonia solani belong to plant pathogens. Among them, Botrytis cinerea belongs to Deuteromycotina and has strong pathogenicity. It is one of the nine most harmful spoilage diseases in the world. It occurs in most countries such as China, the UK, France, Egypt, the US, and New Zealand, and can infect more than 500 kinds of plants such as fruits, vegetables, and flowers, such as strawberries, grapes, greenhouse tomatoes, and greenhouse roses. Currently, commonly used fungicides on the market include chlorothalonil, thiophanate-methyl, azoxystrobin, lime sulfur, Bordeaux mixture, zineb, etc. Although chemical fungicides have the advantages of quick effect and low cost, long-term use gradually causes the pathogens to develop drug resistance and pollutes the environment at the same time. It is reported that Botrytis cinerea already belongs to a pathogen with a high risk of resistance and is known to have developed resistance to fungicides with different mechanisms of action such as amino acid methyl esters, benzimidazoles, phenylpyrimidines, dicarboximides, and benzopyrroles. Rhizoctonia solani Kühn belongs to the fungal kingdom, Basidiomycota, Basidiomycetes, Rhizoctonia. Its sexual state is Thanatephorus cucumeris in Basidiomycota, but the sexual state is generally difficult to find, and it is mostly the asexual state of Rhizoctonia solani in the field. As an important soil-borne pathogenic fungus, this kind of fungus has a very wide host range and can infect more than 260 kinds of plants in 43 families, including crops such as rice, corn, soybeans, and potatoes, causing serious plant diseases and having a huge impact on agricultural production. Rhizoctonia solani is the pathogen of sheath blight of rice and sheath blight of corn, and mainly overwinters in the soil in the form of sclerotia and spreads in the soil, field weeds, and field seedlings through irrigation the next year. The occurrence of sheath blight of rice and sheath blight of corn seriously reduces the yield and quality of rice and corn, usually reducing crop yields by 10%-30%, and may be as high as 50%-70% in severe cases. Chemical control is still the most extensive and effective method for controlling Rhizoctonia solani diseases. There are many bactericidal pesticides for controlling this disease on the market, including hexaconazole, jinggangmycin, thifluzamide suspension, benzyl propiconazole triadimefon, and hekuling powder. However, with the long-term use of chemical agents, the pathogens have developed drug resistance, and the long-term use of pesticides has a greater impact on environmental pollution. Therefore, it is urgent to develop environmentally friendly and highly efficient green chemical pesticides.

[0005] In the process of creating green chemical pesticides, the research on green synthetic process flows is a crucial link. Due to the advantages of green and sustainable synthesis, electrochemistry has received extensive attention from researchers in academia and industry. Since the discovery of the Kolbe anodic oxidation reaction in 1848, electrochemistry has developed into an important applied technology. Organic electrochemistry synthesis uses electrons as reagents and realizes the reduction and oxidation of substances through the gain and loss of electrons. It can avoid using traditional oxidants / reductants in conventional chemical reactions and is characterized by being green, environmentally friendly, and mild. It is regarded as the representative of "green and sustainable" chemistry. Organic electrochemistry synthesis is to synthesize organic compounds by using electrochemical oxidation or reduction methods. Compared with organic synthesis, organic electrochemistry synthesis has unique advantages: such as being achieved through the gain and loss of electrons by reactants on the electrode, without the need to add redox reagents; it can be carried out at normal temperature and pressure, with mild reaction conditions and low requirements for reaction equipment; the electrode reaction and rate can be conveniently controlled by adjusting the electrode potential and current density. This greatly simplifies the reaction steps, reduces the consumption of substances and the occurrence of side reactions, and is very consistent with the principles of atom economy and green chemistry. Therefore, it has very important research significance to synthesize a series of novel organic active small molecule compounds by using an organic electrochemistry catalytic system in the process of creating green chemical pesticides. Summary of the Invention

[0006] In view of this, the technical problem to be solved by the present invention is to design an alkenyl-substituted tellurium organic compound, an alkenyl-substituted tellurium organic compound and its novel electrocatalytic three-component reaction for the selective mono-functionalization of olefins, a preparation method of a tellurium organic compound using elemental tellurium as a tellurium source, an alkenyl-substituted tellurium organic compound and its application. The designed and prepared alkenyl-substituted tellurium organic compound of the present invention not only conforms to the concept of green synthesis, but also provides new possibilities for the efficient formation of a variety of novel tellurium organic compounds; in addition, the designed and prepared alkenyl-substituted tellurium organic compound of the present invention also exhibits obvious anti-plant pathogenic fungus activity, especially against Botrytis cinerea and Rhizoctonia solani. At a concentration of 100 mg / L, the tellurium organic compounds (A-12, A-18, A-19) have EC 50 values that are superior to the control commercial drug azoxystrobin (EC 50 value = 17.1 μg / mL), providing a novel tellurium organic lead compound and its efficient synthesis method for the creation of novel green pesticides. Moreover, the preparation method is simple and easy to implement, with mild conditions, no need for transition metals, external oxidants / reductants, strong controllability, can be carried out at normal temperature and pressure, good functional group compatibility and easy to scale up, and is more conducive to the popularization and application of industrial production.

[0007] To achieve this purpose, the present invention adopts the following technical solutions: The present invention provides a tellurium organic compound substituted with alkenyl groups, which is prepared by an electrochemical synthesis method, that is, the present invention provides an electrochemical synthesis method for a tellurium organic compound substituted with alkenyl groups.

[0008] The present invention provides a tellurium organic compound substituted with alkenyl groups, having any one of the structures shown in formulas (A-1) to (A-23): 。

[0009] The present invention provides a preparation method for a tellurium organic compound substituted with alkenyl groups, which is an electrochemical synthesis method, that is, the present invention provides an electrochemical synthesis method for a preparation method of a tellurium organic compound substituted with alkenyl groups.

[0010] The present invention provides a preparation method for a tellurium organic compound substituted with alkenyl groups, comprising the following steps: Equip a metal rod as the anode and a carbon rod as the cathode. Under the atmosphere of a protective gas, an alkenyl compound, tellurium elemental powder, sulfinate, base reagent, and electrolyte are subjected to an electrified stirring reaction to obtain a tellurium organic compound substituted with alkenyl groups having any one of the structures of formulas (A-1) to (A-23).

[0011] Preferably, in the step, the molar ratio of the alkenyl compound to the tellurium elemental powder and the sulfinate is 1:(1-1.6):(1-1.8).

[0012] Preferably, in the step, the alkenyl compound is one of p-methylstyrene, styrene, p-methoxystyrene, p-chlorostyrene, p-methylcyanostyrene, m-methylstyrene, o-methylstyrene, m-chlorostyrene, o-chlorostyrene, 2-vinylnaphthalene, 2-vinylthiophene, 1-vinyl-1H-1,2,4-triazole, p-divinylbenzene, 1-phenyl-1,3-butadiene.

[0013] Preferably, in the step, the sulfinate is one of sodium p-toluenesulfinate, sodium 4-methoxyphenylsulfinate, sodium p-chlorophenylsulfinate, sodium p-fluorophenylsulfinate, sodium thiophene-2-sulfinate, sodium pyrimidine-2-sulfinate, sodium naphthalene-2-sulfinate, sodium ethylsulfinate, sodium cyclohexylsulfinate, sodium cyclopropylsulfinate.

[0014] Preferably, in the step, the electrolyte is one of ammonium iodide, potassium iodide, sodium iodide, lithium bromide, tetrabutylammonium iodide, ammonium bromide, and tetrabutylammonium bromide; the molar ratio of the alkenyl compound to the electrolyte is 1:(1-1.6).

[0015] Preferably, in the step, the base reagent is one of sodium carbonate, cesium carbonate, sodium bicarbonate, calcium hydroxide, and triethylamine; the molar ratio of the alkenyl compound to the base reagent is 1:(1-2.5).

[0016] Preferably, in the step, the protective gas includes nitrogen and / or argon.

[0017] Preferably, in the step, the reaction is carried out in a mixed solvent, and the mixed solvent for the reaction is one of water and acetonitrile, water and dimethyl sulfoxide, water and tetrahydrofuran, water and N,N-dimethylformamide, and water and dichloromethane.

[0018] Preferably, in the step, the temperature of the reaction is 10~30 °C; the constant current intensity of the reaction is 5~30 mA; the stirring speed of the reaction is 400~1000 r / min; the reaction time is 3~12 h.

[0019] The present invention provides an alkenyl-substituted tellurium organic compound, and the application of the alkenyl-substituted tellurium organic compound prepared by a preparation method of the alkenyl-substituted tellurium organic compound in anti-plant pathogens such as Botrytis cinerea and Rhizoctonia solani.

[0020] Compared with the prior art, the present invention provides an alkenyl-substituted tellurium organic compound. The chemical structure of the alkenyl-substituted tellurium organic compound provided by the present invention is shown in Formulas (A-1) to (A-23). The alkenyl-substituted tellurium organic compound provided by the present invention is a novel tellurium organic compound, which enriches the structural diversity of tellurium organic compounds. The present invention also provides a preparation method of the alkenyl-substituted tellurium organic compound. The preparation method provided by the present invention includes the following steps: configuring a metal rod as the anode and a carbon rod as the cathode, and adding an alkenyl compound, tellurium elemental powder, sulfinate, base reagent, and electrolyte into a mixed solvent under a protective gas atmosphere to form a reaction system, and performing an electrified stirring reaction to obtain an alkenyl-substituted tellurium organic compound with the structure of Formulas (A-1) to (A-23). The method provided by the present invention is a preparation method of a tellurium organic compound using an alkenyl compound, tellurium elemental powder, and sulfinate as starting materials, a brand-new electrocatalytic three-component reaction for the selective mono-functionalization of olefins, and using elemental tellurium as the tellurium source, and finally preparing an alkenyl-substituted tellurium compound. The preparation method provided by the present invention is a newly designed reaction path, which provides a new idea for broadening the synthetic methodology of alkenyl-substituted tellurium organic compounds; and the raw materials used in this method have low cost and wide sources, the reaction conditions are mild and efficient, and it can be carried out under normal temperature and pressure without adding transition metals, oxidation reducers, and acid reagents, and the product added value increases significantly, having a wide range of application scenarios. The tellurium organic compound prepared by the present invention exhibits obvious anti-plant pathogen activity, especially suitable for the activity against Botrytis cinerea and Rhizoctonia solani, providing a novel tellurium organic lead compound and its efficient synthesis method for the creation of new green pesticides. Description of the Drawings

[0021] The present invention will be further described below with reference to the drawings and embodiments.

[0022] Figure 1 Chemical structural formula of the alkenyl-substituted tellurium organic compound prepared in Examples 1 to 23 of the present invention.

[0023] Figure 2 Possible reaction mechanism diagram for the electrochemically synthesized alkenyl-substituted tellurium organic compound of the present invention.

[0024] Figure 3 High-resolution mass spectrum of p-methylbenzaldehyde in Comparative Example 1 of the present invention. Detailed implementation manners

[0025] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts shall fall within the protection scope of the present invention.

[0026] The present invention provides an alkenyl-substituted tellurium organic compound, which is prepared by an electrochemically synthetic method, that is, the present invention provides an electrochemically synthetic method for preparing an alkenyl-substituted tellurium organic compound.

[0027] The present invention provides an alkenyl-substituted tellurium organic compound having any one of the structures shown in Formulas (A-1) to (A-23): .

[0028] The alkenyl-substituted tellurium organic compound provided by the present invention is a novel type of tellurium organic compound, which enriches the structural diversity of alkenyl-substituted tellurium organic compounds.

[0029] The present invention provides a preparation method for an alkenyl-substituted tellurium organic compound, which is an electrochemically synthetic method, that is, the present invention provides a preparation method for an electrochemically synthesized alkenyl-substituted tellurium organic compound.

[0030] The present invention also provides a preparation method for an alkenyl-substituted tellurium organic compound, comprising the following steps: Equip a metal rod as the anode and a carbon rod as the cathode, and carry out an electrified stirring reaction on the alkenyl compound, tellurium elemental powder, sulfite, base reagent and electrolyte under a protective gas atmosphere to obtain an alkenyl-substituted tellurium organic compound having any one of the structures shown in Formulas (A-1) to (A-23).

[0031] In the preparation method provided by the present invention, the reaction equation involved in the steps is as follows: , where Het is preferably or or or or, R is preferably 4-H or 4-CH 3 or 4-OCH 3 or 4-Cl or 4-CN or 3-CH 3 or 2-CH 3 or 3-Cl or 2-Cl, R 1 is preferably or or or or or or or or 。

[0032] In the preparation method provided by the present invention, in the step, the molar ratio of the alkenyl compound, tellurium elemental powder, and sulfite is preferably 1: (1 to 1.6): (1 to 1.8), and specifically can be 1:1:1, 1:1.05:1.1, 1:1.2:1.24, 1:1.3:1.36, 1:1.37:1.42, 1:1.4:1.55, 1:1.5:1.62, 1:1.58:1.72, or 1:1.6:1.8.

[0033] In the preparation method provided by the present invention, in the step, the alkenyl compound is preferably one of p-methylstyrene, styrene, p-methoxystyrene, p-chlorostyrene, p-methylcyanostyrene, m-methylstyrene, o-methylstyrene, m-chlorostyrene, o-chlorostyrene, 2-vinylnaphthalene, 2-vinylthiophene, 1-vinyl-1H-1,2,4-triazole, p-divinylbenzene, 1-phenyl-1,3-butadiene.

[0034] In the preparation method provided by the present invention, in the step, the sulfite is preferably one of sodium p-toluenesulfinate, sodium 4-methoxyphenylsulfinate, sodium p-chlorophenylsulfinate, sodium p-fluorophenylsulfinate, sodium thiophene-2-sulfinate, sodium pyrimidine-2-sulfinate, sodium naphthalene-2-sulfinate, sodium ethylsulfinate, sodium cyclohexylsulfinate, or sodium cyclopropylsulfinate.

[0035] In the preparation method provided by the present invention, in the step, the electrolyte is preferably one of ammonium iodide, potassium iodide, sodium iodide, lithium bromide, tetrabutylammonium iodide, ammonium bromide, and tetrabutylammonium bromide; the molar ratio of the alkenyl compound to the electrolyte is preferably 1: (1 to 1.6), and specifically can be 1:1, 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1:1.5, or 1:1.6.

[0036] In the preparation method provided by the present invention, in the step, the alkali reagent is preferably one of sodium carbonate, cesium carbonate, sodium bicarbonate, calcium hydroxide and triethylamine; the molar ratio of the alkenyl compound to the alkali reagent is 1:(1-2.5).

[0037] In the preparation method provided by the present invention, in the step, the protective gas preferably includes nitrogen and / or argon.

[0038] In the preparation method provided by the present invention, in the step, the reaction is carried out in a mixed solvent, and the mixed solvent for the reaction is preferably one of water and acetonitrile, water and dimethyl sulfoxide, water and tetrahydrofuran, water and N,N-dimethylformamide, and water and dichloromethane.

[0039] In the preparation method provided by the present invention, in the step, the temperature of the reaction is specifically preferably 10-30 °C; the constant current intensity of the reaction is specifically preferably 5-30 mA; the rotation speed of the stirring reaction is specifically preferably 400-1000 r / min; the reaction time is specifically preferably 3-12 h. In the present invention, the reaction is an electro-stirring reaction, preferably monitoring the reaction degree by thin-layer chromatography to determine the end time of the reaction and stop energizing, and after the reaction is completed, post-treatment is carried out. The reaction mixture is diluted with ethyl acetate, washed and extracted with a saturated sodium chloride solution, dried with sodium sulfate to remove water, the solvent is removed by vacuum distillation, and the mixture is rapidly separated by silica gel column chromatography using petroleum ether and ethyl acetate as eluents, and the solvent is removed by rotary evaporation to obtain an alkenyl-substituted tellurium organic compound with any one of the structures of formula (A-1)-(A-23).

[0040] Other point values within the above numerical ranges can be selected and will not be elaborated one by one here.

[0041] In the present invention, the alkenyl-substituted tellurium organic compound or the alkenyl-substituted tellurium organic compound prepared by the preparation method of the alkenyl-substituted tellurium organic compound can be applied in anti-plant pathogens, and is particularly suitable for the activities against Botrytis cinerea and Rhizoctonia solani.

[0042] The method provided by the present invention uses an alkenyl compound, tellurium powder, and a sulfite as starting materials. A novel electrocatalytic three-component reaction is used for the selective mono-functionalization of olefins, and it is a preparation method of an organotellurium compound using elemental tellurium as a tellurium source. An alkenyl-substituted tellurium compound is finally prepared; this method is a newly designed reaction path, providing new ideas for broadening the synthetic methodology of alkenyl-substituted organotellurium compounds; moreover, the raw materials used in this method have low costs, wide sources, high reaction efficiency, and significantly increased product added value, and have a wide range of application scenarios. The organotellurium compound prepared by the present invention exhibits obvious anti-plant pathogenic bacterium activity, especially suitable for the activity against Botrytis cinerea and Rhizoctonia solani, providing a novel organotellurium lead compound and its efficient synthesis method for the creation of new green pesticides.

[0043] To prove the feasibility of the method provided by the present invention, we designed a control reaction experiment. Under standard conditions, in the absence of an alkenyl compound, the reaction between a sulfite and tellurium powder does not produce the intermediate sulfonyl tellurium salt, indicating that this salt does not participate in this transformation; in the absence of tellurium powder, a trace amount of alkenyl sulfone compound was observed as a by-product; using ethylene-1,1-diphenyl as a trapping reagent, sulfonyl and iodine radicals were detected by high-resolution mass spectrometry (HRMS); ditelluride was observed by gas chromatography-mass spectrometry (GC-MS), indicating that sulfonyl tellurium radicals may be generated during the reaction process.

[0044] The possible reaction mechanism of the preparation method provided by the present invention is as Figure 2 shown: First, the sulfite is anodically oxidized to a sulfonyl radical, and at the same time, the electrolyte will anodically oxidize to generate a halogen radical; subsequently, tellurium powder reacts with the sulfonyl radical to generate a sulfonyl tellurium radical intermediate, which participates in the addition reaction of the alkenyl compound, and finally obtains an alkenyl-containing organotellurium compound through the elimination of hydrogen halide; and according to the principle of charge conservation, the cathode will reduce the solvent water.

[0045] For clarity, the following will be described in detail through the following examples and comparative examples; in the following examples of the present invention, the synthetic routes involved are as follows: , where Het is preferably or or or or , R is preferably 4-H or 4-CH 3 or 4-OCH 3 or 4-Cl or 4-CN or 3-CH 3 or 2-CH 3 or 3-Cl or 2-Cl, R 1 is preferably or or or or or or or or 。

[0046] For all raw materials of the present invention, there are no special restrictions on their sources, and they can be purchased on the market or prepared by conventional methods well-known to those skilled in the art.

[0047] To complete and refine the overall technical solution of the present invention, the above-mentioned alkenyl-substituted tellurium organic compounds, preparation methods and applications may specifically include the following content.

[0048] Example 1 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.3 mol of sodium carbonate and 0.3 mol of ammonium iodide to water and acetonitrile to form a reaction system. Apply a constant current of 10 mA, keep the temperature of the reaction system at 25 °C, stir at 550 r / min, react for 12 h, monitor the reaction progress by thin-layer chromatography to determine the end point time of the reaction, stop energizing, and perform post-treatment after the reaction is completed. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 3 times with 0.83 mol of supersaturated saline solution, dry and remove water with 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-tellurium-(4-methylstyryl)4-methylbenzenesulfonate; Yield: 42%, HRMS (ESI) m / z: [M+H] + Calcd for:C 16 H 17 O 2 STe + 402.9933; Found: 402.9933. The chemical structural formula is as follows: 。

[0049] Example 2 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, 0.3 mol of an alkenyl compound, 0.36 mol of tellurium powder, 0.36 mol of sulfinate, 0.3 mol of cesium carbonate, and 0.3 mol of potassium iodide were added to water and dimethyl sulfoxide to form a reaction system. A constant current of 10 mA was applied, and the temperature of the reaction system was maintained at 15 °C. The reaction mixture was stirred at 450 r / min and reacted for 5 h. The reaction progress was monitored by thin-layer chromatography to determine the end point of the reaction and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted 3 times with 0.83 mol of supersaturated sodium chloride solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-p-Styryl 4-methylbenzenesulfonate; Yield: 53%, HRMS (ESI) m / z: [M+H] + Calcd for: C 15 H 15 O 2 STe + 388.9777; Found: 388.9779. The chemical structural formula is as follows: .

[0050] Example 3 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, 0.3 mol of an alkenyl compound, 0.39 mol of tellurium powder, 0.39 mol of sulfinate, 0.3 mol of sodium bicarbonate, and 0.3 mol of sodium iodide were added to water and tetrahydrofuran to form a reaction system. A constant current of 15 mA was applied, and the temperature of the reaction system was maintained at 17 °C. The reaction mixture was stirred at 500 r / min and reacted for 6 h. The reaction progress was monitored by thin-layer chromatography to determine the end point of the reaction and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted 2 times with 0.83 mol of supersaturated sodium chloride solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-Telluro-(4-methoxystyryl) 4-methylbenzenesulfonate; Yield: 60%, HRMS (ESI) m / z: [M+H] + Calcd for: C 16 H 17 O 3 STe +418.9882; Found: 418.9884. The chemical structural formula is as follows: .

[0051] Example 4 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.42 mol of tellurium powder, 0.42 mol of sulfite, 0.3 mol of calcium hydroxide, and 0.3 mol of lithium bromide to water and N,N-dimethylformamide to form a reaction system. Apply a constant current of 17 mA, maintain the temperature of the reaction system at 16 °C, stir while energizing at 600 r / min, react for 8 h, monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, carry out post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 2 times with 0.83 mol of supersaturated brine solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-telluro-(4-chlorostyryl)4-methylbenzenesulfonate; Yield: 61%, HRMS (ESI) m / z: [M+H] + Calcd for: C 15 H 14 ClO 2 STe + 422.9387; Found: 422.9385. The chemical structural formula is as follows: .

[0052] Example 5 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of an alkenyl compound, 0.45 mol of tellurium powder, 0.42 mol of sulfite, 0.3 mol of triethylamine, and 0.3 mol of tetrabutylammonium iodide to water and dichloromethane to form a reaction system. Apply a constant current of 20 mA, maintain the temperature of the reaction system at 18 °C, stir while energizing at 650 r / min, react for 9 h, monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, carry out post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 3 times with 0.83 mol of supersaturated brine solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain a white solid of ( E)-Telluro-(4-cyanostyryl)4-methylbenzenesulfonate; Yield: 60%, HRMS (ESI) m / z: [M+H] + Calcd for: C 16 H 14 NO 2 STe + 413.9729; Found: 413.9725. The chemical structural formula is as follows: 。

[0053] Example 6 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 moles of the alkenyl compound, 0.39 moles of tellurium powder, 0.42 moles of sulfite, 0.525 moles of sodium carbonate, and 0.39 moles of ammonium iodide to water and acetonitrile to form a reaction system. Apply a constant current of 8 mA, maintain the temperature of the reaction system at 10 °C, stir at 700 r / min, react for 3 h, monitor the reaction progress by thin-layer chromatography to determine the end point time of the reaction, stop energizing, and perform post-treatment after the reaction is completed. Dilute the reaction mixture with 0.57 moles of ethyl acetate, wash and extract 2 times with 0.83 moles of supersaturated sodium chloride solution, dry and remove water with 0.1 moles of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-Telluro-(3-methylstyryl)4-methylbenzenesulfonate; Yield: 43%, HRMS (ESI) m / z: [M+H] + Calcd for:C 16 H 17 O 2 STe + 402.9933; Found: 402.9936. The chemical structural formula is as follows: 。

[0054] Example 7 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, 0.3 mol of an alkenyl compound, 0.48 mol of tellurium powder, 0.54 mol of sulfinate, 0.75 mol of sodium carbonate, and 0.48 mol of ammonium iodide were added to water and acetonitrile to form a reaction system. A constant current of 18 mA was applied, and the temperature of the reaction system was maintained at 25 °C. The mixture was stirred while being electrified at 650 r / min for 12 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted 3 times with 0.83 mol of supersaturated saline solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(2-methylstyryl)4-methylbenzenesulfonate; Yield: 60%, HRMS (ESI) m / z: [M+H] + Calcd for:C 16 H 17 O 2 STe + 402.9933; Found: 402.9934. The chemical structural formula is as follows: .

[0055] Example 8 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfinate, 0.525 mol of cesium carbonate, and 0.39 mol of potassium iodide were added to the solvents water and dimethyl sulfoxide to form a reaction system. A constant current of 5 mA was applied, and the temperature of the reaction system was maintained at 20 °C. The mixture was stirred while being electrified at 400 r / min for 3 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted 2 times with 0.83 mol of supersaturated saline solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(3-chlorostyryl)4-methylbenzenesulfonate; Yield: 68%, HRMS (ESI) m / z: [M+H] + Calcd for:C 15 H 14 ClO 2 STe +422.9387; Found: 422.938. The chemical structural formula is as follows: .

[0056] Example 9 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfinate, 0.75 mol of cesium carbonate, and 0.48 mol of potassium iodide to water and tetrahydrofuran to form a reaction system. Apply a constant current of 30 mA, maintain the temperature of the reaction system at 30 °C, stir while electrifying at 1000 r / min, react for 12 h, monitor the reaction progress by thin-layer chromatography, stop electrifying at the determined end point time of the reaction. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 3 times with 0.83 mol of supersaturated sodium chloride solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-telluro-(2-chlorostyryl)4-methylbenzenesulfonic acid; Yield: 54%, HRMS (ESI) m / z: [M+H] + Calcd for:C 15 H 14 ClO 2 STe + 422.9387; Found: 422.9383. The chemical structural formula is as follows: .

[0057] Example 10 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfinate, 0.525 mol of sodium bicarbonate, and 0.39 mol of sodium iodide to water and N,N-dimethylformamide to form a reaction system. Apply a constant current of 17 mA, maintain the temperature of the reaction system at 20 °C, stir while electrifying at 700 r / min, react for 8 h, monitor the reaction progress by thin-layer chromatography, stop electrifying at the determined end point time of the reaction. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 3 times with 0.83 mol of supersaturated sodium chloride solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E)-Telluro-(2-(naphthalen-2-yl)vinyl)4-methylbenzenesulfonate; Yield: 65%, HRMS (ESI) m / z: [M+H] + Calcd for: C 19 H 17 O 2 STe + 438.9933; Found: 438.9936. The chemical structural formula is as follows: 。

[0058] Example 11 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of the alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfinate, 0.75 mol of sodium bicarbonate, and 0.48 mol of sodium iodide to water and dichloromethane to form a reaction system. Apply a constant current of 30 mA, maintain the temperature of the reaction system at 30 °C, stir while energizing at 1000 r / min, react for 12 h, monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction, stop energizing, and perform post-treatment after the reaction is completed. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract it 2 times with 0.83 mol of supersaturated sodium chloride solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-Telluro-(2-(thiophen-2-yl)vinyl)4-methylbenzenesulfonate; Yield: 62%, HRMS (ESI) m / z: [M+H] + Calcd for: C 13 H 13 O 2 S 2 Te + 394.9341; Found: 394.9346. The chemical structural formula is as follows: 。

[0059] Example 12 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.525 mol of calcium hydroxide, and 0.39 mol of lithium bromide were added to a reaction system composed of water and dimethyl sulfoxide. A constant current of 17 mA was applied, and the temperature of the reaction system was maintained at 20 °C. The reaction mixture was stirred while being electrified at 700 r / min for 8 h. The reaction progress was monitored by thin-layer chromatography to determine the end point time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted twice with 0.83 mol of supersaturated saline solution, dried with 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(2-(1H-1,2,4-triazol-1-yl)vinyl)4-methylbenzenesulfonate; Yield: 50%, HRMS (ESI) m / z: [M+H] + Calcd for: C 11 H 12 N 3 O 2 STe + 379.9634; Found: 379.9636. The chemical structural formula is as follows: .

[0060] Example 13 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.75 mol of calcium hydroxide, and 0.48 mol of lithium bromide were added to a reaction system composed of water and tetrahydrofuran. A constant current of 30 mA was applied, and the temperature of the reaction system was maintained at 30 °C. The reaction mixture was stirred while being electrified at 1000 r / min for 12 h. The reaction progress was monitored by thin-layer chromatography to determine the end point time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted twice with 0.83 mol of supersaturated saline solution, dried with 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain telluro, telluro'-((1 E ,1' E )-1,4-phenylenebis(ethene-2,1-diyl))bis(4-methylbenzenesulfonate); Yield: 62%, HRMS(ESI) m / z: [M+H] +Calcd for: C 24 H 23 O 4 S 2 Te 2 + 698.9084; Found: 698.9085. The chemical structural formula is as follows: .

[0061] Example 14 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfinate, 0.525 mol of triethylamine, and 0.39 mol of tetrabutylammonium iodide to a reaction system composed of water and N,N-dimethylformamide. Apply a constant current of 18 mA, keep the temperature of the reaction system at 20 °C, stir while electrifying at 700 r / min for 8 h. Monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop electrifying. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract it 3 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain tellurium-((1 E ,3 E )-4-phenylbut-1,3-dien-1-yl)4-methylbenzenesulfonate; Yield: 48%, HRMS (ESI) m / z: [M+H] + Calcd for: C 17 H 17 O 2 STe + 414.9933; Found: 414.9936. The chemical structural formula is as follows: .

[0062] Example 15 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfite, 0.75 mol of triethylamine, and 0.39 mol of tetrabutylammonium iodide were added to a reaction system composed of water and dichloromethane. A constant current of 30 mA was applied, and the temperature of the reaction system was maintained at 30 °C. The mixture was stirred while being energized at 1000 r / min for 12 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted twice with 0.83 mol of supersaturated saline solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was quickly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(4-methylstyryl)4-methoxybenzenesulfonate; Yield: 74%, HRMS (ESI) m / z: [M+H] + Calcdfor: C 16 H 17 O 3 STe + 418.9882; Found: 418.9885. The chemical structural formula is as follows: 。

[0063] Example 16 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfite, 0.525 mol of sodium carbonate, and 0.39 mol of ammonium bromide were added to a reaction system composed of water and acetonitrile. A constant current of 15 mA was applied, and the temperature of the reaction system was maintained at 18 °C. The mixture was stirred while being energized at 700 r / min for 9 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted three times with 0.83 mol of supersaturated saline solution, dried over 0.1 mol of sodium sulfate to remove water, and the solvent was removed by distillation under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was quickly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(4-methylstyryl)4-chlorobenzenesulfonylethyl benzoate; Yield: 67%, HRMS (ESI) m / z: [M+H] + Calcd for:C 15 H 14 ClO 2 STe +422.9387; Found: 422.9384. The chemical structural formula is as follows: .

[0064] Example 17 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfite, 0.75 mol of sodium carbonate, and 0.48 mol of ammonium bromide to a reaction system composed of water and dimethyl sulfoxide. Apply a constant current of 8 mA, maintain the temperature of the reaction system at 25 °C, stir while electrifying at 750 r / min, react for 9 h, monitor the reaction progress by thin-layer chromatography, stop electrifying at the determined reaction end time, and perform post-treatment after the reaction is completed. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 2 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-telluro-(4-methylstyryl)4-fluorobenzenesulfonate; Yield: 60%, HRMS (ESI) m / z: [M+H] + Calcd for:C 15 H 14 FO 2 STe + 406.9683; Found: 406.9685. The chemical structural formula is as follows: .

[0065] Example 18 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfite, 0.525 mol of cesium carbonate, and 0.39 mol of tetrabutylammonium bromide to a reaction system composed of water and tetrahydrofuran. Apply a constant current of 9 mA, maintain the temperature of the reaction system at 23 °C, stir while electrifying at 620 r / min, react for 11 h, monitor the reaction progress by thin-layer chromatography, stop electrifying at the determined reaction end time, and perform post-treatment after the reaction is completed. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 2 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 8:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E)-Telluro-(4-methylstyryl)thiophene-2-sulfonate; Yield: 48%, HRMS (ESI) m / z: [M+H] + Calcd for: C 13 H 13 O 2 S 2 Te + 394.9341; Found: 394.9343. The chemical structural formula is as follows: .

[0066] Example 19 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of the alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfite, 0.75 mol of cesium carbonate, and 0.48 mol of tetrabutylammonium bromide to water and N,N-dimethylformamide to form a reaction system. Apply a constant current of 11 mA, keep the temperature of the reaction system at 26 °C, stir while energizing, at 640 r / min, react for 10 h. Monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, carry out post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract it 2 times with 0.83 mol of supersaturated sodium chloride solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, use petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-Telluro-(4-methylstyryl)pyrimidine-2-sulfoethyl propionate; Yield: 62%, HRMS (ESI) m / z: [M+H] + Calcd for: C 13 H 13 N 2 O 2 STe + 390.9682; Found: 390.9684. The chemical structural formula is as follows: .

[0067] Example 20 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.525 mol of calcium hydroxide, and 0.39 mol of tetrabutylammonium bromide were added to water and dichloromethane to form a reaction system. A constant current of 13 mA was applied, and the temperature of the reaction system was maintained at 18 °C. The mixture was stirred while being electrified at 500 r / min for 11 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted twice with 0.83 mol of supersaturated sodium chloride solution, dried with 0.1 mol of sodium sulfate to remove water, and the solvent was removed by vacuum distillation. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(4-methylstyryl)naphthalene-2-sulfonate; Yield: 50%, HRMS (ESI) m / z: [M+H] + Calcd for: C 19 H 17 O 2 STe + 438.9933; Found: 438.9937. The chemical structural formula is as follows: .

[0068] Example 21 An undivided three-necked reaction flask was equipped with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.75 mol of calcium hydroxide, and 0.48 mol of tetrabutylammonium bromide were added to water and dichloromethane to form a reaction system. A constant current of 12 mA was applied, and the temperature of the reaction system was maintained at 28 °C. The mixture was stirred while being electrified at 580 r / min for 13 h. The reaction progress was monitored by thin-layer chromatography to determine the end time of the reaction, and then the power supply was stopped. After the reaction was completed, post-treatment was carried out. The reaction mixture was diluted with 0.57 mol of ethyl acetate, washed and extracted twice with 0.83 mol of supersaturated sodium chloride solution, dried with 0.1 mol of sodium sulfate to remove water, and the solvent was removed by vacuum distillation. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, the mixture was rapidly separated by silica gel column chromatography, and the solvent was removed by rotary evaporation to obtain ( E )-telluro-(4-methylstyryl)ethyl sulfonate; Yield: 62%, HRMS (ESI) m / z: [M+H] + Calcd for:C 11 H 15 O 2 STe +340.9777; Found: 340.9773. The chemical structural formula is as follows: .

[0069] Example 22 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an argon atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.525 mol of triethylamine, and 0.39 mol of lithium bromide to water and dimethyl sulfoxide to form a reaction system. Apply a constant current of 15 mA, maintain the temperature of the reaction system at 22 °C, stir while energizing, at 490 r / min, react for 13 h. Monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 2 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E )-telluro-(4-methylstyryl)cyclohexanesulfonate; Yield: 61%, HRMS (ESI) m / z: [M+H] + Calcd for:C 15 H 21 O 2 STe + 395.0246; Found: 395.0245. The chemical structural formula is as follows: .

[0070] Example 23 Equip an undivided three-necked reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a nitrogen atmosphere, add 0.3 mol of an alkenyl compound, 0.3 mol of tellurium elemental powder, 0.3 mol of sulfinate, 0.75 mol of triethylamine, and 0.48 mol of lithium bromide to water and dichloromethane to form a reaction system. Apply a constant current of 30 mA, maintain the temperature of the reaction system at 30 °C, stir while energizing, at 590 r / min, react for 12 h. Monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract 2 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure. Using petroleum ether and ethyl acetate (volume ratio 7:1) as the eluent, quickly separate the mixture by silica gel column chromatography, and rotary evaporate to remove the solvent to obtain ( E)-Telluro-(4-methylstyryl)cyclopropanesulfonate; Yield: 57%, HRMS (ESI) m / z: [M+H] + Calcd for: C 12 H 15 O 2 STe + 352.9777; Found: 352.9774. The chemical structural formula is as follows: 。

[0071] Comparative Example 1 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under an air atmosphere, add 0.3 mol of the alkenyl compound, 0.3 mol of tellurium powder, 0.3 mol of sulfite, 0.3 mol of sodium carbonate, and 0.3 mol of ammonium iodide to water and acetonitrile to form a reaction system. Apply a constant current of 10 mA, keep the temperature of the reaction system at 25 °C, stir while energizing at 550 r / min, react for 12 h, monitor the reaction progress by thin-layer chromatography to determine the end time of the reaction and stop energizing. After the reaction is completed, perform post-treatment. Dilute the reaction mixture with 0.57 mol of ethyl acetate, wash and extract it 3 times with 0.83 mol of supersaturated saline solution, dry and remove water using 0.1 mol of sodium sulfate, distill off the solvent under reduced pressure, and perform high-resolution mass spectrometry testing. From Figure 3 it can be seen that the tellurium-containing organic compound with alkenyl substitution was not obtained, but the p-methylbenzaldehyde compound after oxidation of the alkenyl compound was obtained. HRMS (ESI) calcd for C 8 H 9 O [M+H] + : 121.0289, found: 121.0294.

[0072] Comparative Example 2 Equip an undivided three-neck reaction flask with a magnesium rod as the anode and a carbon rod as the cathode. Under a protective gas atmosphere, add 0.3 mol of the alkenyl compound, 0.3 mol of biphenylditelluride, 0.3 mol of sulfite, 0.3 mol of sodium carbonate, and 0.3 mol of ammonium iodide to water and acetonitrile to form a reaction system. Apply a constant current of 10 mA, keep the temperature of the reaction system at 25 °C, stir while energizing at 550 r / min, and stop the reaction after 12 h. Take the reaction solution for high-resolution mass spectrometry testing, and the results show that the tellurium-containing organic compound with alkenyl substitution was not obtained.

[0073] Application Example 1 At a concentration of 100 μg / mL, the inhibitory effect of alkenyl-substituted tellurium organic compounds on the plant pathogenic fungus Botrytis cinerea was tested, and the commercial drug azoxystrobin was used as a positive control. The antifungal activity of alkenyl-substituted tellurium organic compounds against B. cinerea was evaluated by the mycelial growth rate method. The compound to be tested was dissolved in dimethyl sulfoxide, and the test substance was added to the sterile molten potato dextrose agar medium cooled to 60 - 65 °C in a sterile laminar flow hood to prepare a concentration of 100 μg / mL. 5 mL of the above-mentioned mixed medium was poured into a sterile petri dish with a diameter of 6 cm, and then 4 mm of the plant pathogenic fungus was inoculated. A sterile molten potato dextrose agar medium containing 100 μg / mL concentration of dimethyl sulfoxide in water was used as a control. Each treatment included three replicates. After the control petri dish was completely covered with fungal mycelium, the diameter of the mycelial growth was measured, and the inhibition percentage relative to the control was calculated using the following formula: I (%) = (C - T) / (C - d) × 100, where d is the diameter of the cut fungus (4 mm), I is the inhibition rate (%), and C and T represent the average colony diameters of the mycelia of the control and the treatment, respectively. The median effective concentration (EC 50 ) value was statistically estimated by Probit analysis using the Probit package of SPSS version 17.0 software. Each experiment was repeated three times. All the tested compounds had a purity greater than 95% and showed inhibitory effects on B. cinerea (see Table 1). Among them, the target compounds A-4, A-11, A-12, A-18, and A-19 showed inhibition rates exceeding 79% against B. cinerea at a concentration of 100 mg / L, which was significantly higher than that of the control agent azoxystrobin (78.5%). The EC 50 values of A-12, A-18, and A-19 against B. cinerea were 14.2 μg / mL, 16.8 μg / mL, and 17.0 μg / mL, respectively, which were better than those of the control drug azoxystrobin (EC 50 value = 17.1 μg / mL).

[0074] Application Example 2 At a concentration of 100 μg / mL, the inhibitory effect of the alkenyl-substituted tellurium organic compound of the present invention on the plant pathogenic fungus Rhizoctonia solani was tested, and the commercial drug azoxystrobin was used as a positive control. The antifungal activity of the alkenyl-substituted tellurium organic compound against Rhizoctonia solani was evaluated by the mycelial growth rate method. The compound to be tested was dissolved in dimethyl sulfoxide, and the test substance was added to the sterile molten potato dextrose agar medium cooled to 60-65 °C in a sterile laminar flow hood to prepare a concentration of 100 μg / mL. 5 mL of the above-mentioned mixed medium was poured into a sterile petri dish with a diameter of 6 cm, and then 4 mm of the plant pathogenic fungus was inoculated. The sterile molten potato dextrose agar medium containing 100 μg / mL of dimethyl sulfoxide in water was used as a control. Each treatment included three replicates. After the control petri dish was completely covered with fungal mycelium, the diameter of the mycelial growth was measured, and the inhibition percentage relative to the control was calculated using the following formula: I (%) = (C - T) / (C - d) × 100, where d is the diameter of the cut fungus (4 mm), I is the inhibition rate (%), and C and T represent the average colony diameters of the mycelium of the control and the treatment, respectively. The median effective concentration (EC 50 ) value was statistically estimated by Probit analysis using the Probit package of SPSS version 17.0 software. Each experiment was repeated three times. All the tested compounds had a purity greater than 95% and showed inhibitory effects on Rhizoctonia solani (see Table 1). At a concentration of 100 μg / mL, the inhibition rates of A-4, A-11, A-12, A-18, and A-19 against Rhizoctonia solani were 85.9%, 87.4%, 91.4%, 90.6%, and 89.2%, respectively, which were better than those of the control commercial agent azoxystrobin (85.3%), showing good inhibitory activity. The EC 50 values of A-12, A-18, and A-19 against Rhizoctonia solani were 8.3, 10.4, and 10.2 μg / mL, respectively, which were better than those of the control agent azoxystrobin (EC 50 value = 10.6 μg / mL).

[0075] Table 1 In vitro antifungal activities of the tested compounds at 100 μg / mL

[0076] The above are only the preferred embodiments of the present invention. It should be noted that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and refinements can be made, and these improvements and refinements should also be regarded as the protection scope of the present invention.

Claims

1. An alkenyl-substituted tellurium organic compound, characterized in that: It has any structure as shown in formula (A-1) to (A-23): 。 2. A method for preparing an alkenyl-substituted tellurium organic compound as claimed in claim 1, characterized in that: The following steps are involved: A metal rod is used as an anode and a carbon rod is used as a cathode. In a protective gas atmosphere, an olefin compound, tellurium powder, sulfinate, alkaline reagent and electrolyte are stirred and reacted to obtain an olefin-substituted tellurium organic compound of any structure of formula (A-1) to (A-23).

3. The preparation method according to claim 2, characterized in that: In the steps, the molar ratio of the alkenyl compound to the tellurium powder and the sulfinate is 1:(1-1.6):(1-1.8).

4. The preparation method according to claim 2, characterized in that: In the step, the alkenyl compound is one of p-methylstyrene, styrene, p-methoxystyrene, p-chlorostyrene, p-cyanostyrene, m-methylstyrene, o-methylstyrene, m-chlorostyrene, o-chlorostyrene, 2-vinylnaphthalene, 2-vinylthiophene, 1-vinyl-1H-1,2,4-triazole, p-divinylbenzene, and 1-benzene-1,3-butadiene.

5. The preparation method according to claim 2, characterized in that: In the step, the sulfinate is one of sodium p-toluenesulfinate, sodium 4-methoxybenzenesulfinate, sodium p-chlorobenzenesulfinate, sodium p-fluorobenzenesulfinate, sodium thiophene-2-sulfinate, sodium pyrimidine-2-sulfinate, sodium naphthalene-2-sulfinate, sodium ethylsulfinate, sodium cyclohexylsulfinate, and sodium cyclopropylsulfinate.

6. The preparation method according to claim 2, characterized in that: In the step, the electrolyte is one of ammonium iodide, potassium iodide, sodium iodide, lithium bromide, tetrabutylammonium iodide, ammonium bromide and tetrabutylammonium bromide; and the molar ratio of the olefinic compound to the electrolyte is 1:(1-1.6).

7. The preparation method according to claim 2, characterized in that: In the step, the alkaline reagent is one of sodium carbonate, cesium carbonate, sodium bicarbonate, calcium hydroxide and triethylamine; and the molar ratio of the alkenyl compound to the alkaline reagent is 1: (1-2.5).

8. The preparation method according to claim 2, characterized in that: In the step, the reaction is carried out in a mixed solvent, and the mixed solvent is one of water and acetonitrile, water and dimethyl sulfoxide, water and tetrahydrofuran, water and N,N-dimethylformamide, and water and dichloromethane.

9. The preparation method according to claim 2, characterized in that: In the step, the reaction temperature is 10-30° C., the constant current intensity of the reaction is 5-30 mA, and the reaction time is 3-12 h.

10. Use of the alkenyl-substituted tellurium organic compound according to claim 1 or the alkenyl-substituted tellurium organic compound prepared by the preparation method according to any one of claims 2 to 9 in resisting plant pathogens; The anti-plant pathogenic bacteria is selected from Botrytis cinerea or Rhizoctonia solani.

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