2-cyanoacrylate compound and use thereof

Abstract

The application discloses a 2-cyanoacrylate compound represented by a general formula (I): each substituent is shown in the specification. The application also discloses a preparation method and application of the 2-cyanoacrylate compound. The 2-cyanoacrylate compound is suitable for inhibiting mycotoxins and preventing diseases caused by pollution fungi.

Description

Technical Field

[0001] This invention belongs to the field of agricultural fungicides, specifically relating to a 2-cyanoacrylate compound and its application in preventing fungal diseases and inhibiting fungal toxin contamination. Background Technology

[0002] Fusarium head blight, a common disease caused by Fusarium graminearum, not only causes large-scale yield reductions in wheat but also severely affects its quality, resulting in significant economic losses. It has become the leading disease affecting high and stable wheat yields in my country. While infecting wheat, Fusarium graminearum produces deoxynivalenol (DON) toxin in wheat grains. This toxin has strong cytotoxicity, significant embryotoxicity, and teratogenic effects, widely contaminating wheat and its products, grain and oil products, and feed, seriously threatening food safety and human and animal health. Currently, 37 countries worldwide have established relevant limits for DON toxin in food or grains. my country's national standard GB2761-2011 stipulates a limit of 1 mg / kg for DON toxin in grains and grain products. Some existing fungicides, such as carbendazim, prochloraz, azoxystrobin, and pyraclostrobin, while reducing disease, simultaneously stimulate the production of DON toxin. Therefore, agricultural fungicides used to control wheat scab must not only effectively control the disease but also reduce the DON toxin content in wheat grains.

[0003] 2-Cyanoacrylate compounds have been highly valued in pesticide development due to their herbicidal, antifungal, and antiviral activities. For example, the fungicide cyazofamid can effectively control diseases such as wheat scab and rice bakanae disease, and also effectively reduce DON toxin contamination.

[0004] Patent CN104068025B discloses the application of a combination of cyazofamid and prothioconazole in the prevention and control of Fusarium head blight and Fusarium head blight toxin contamination in crops. The combination can significantly inhibit the formation of Fusarium head blight toxin.

[0005] Patent CN109730068A discloses the application of 2-cyano-3-amino-3-phenyl acrylate compounds and their compositions, represented by the following general formula (A), in inhibiting cereal mycotoxin contamination, which can reduce the content of cereal mycotoxins.

[0006]

[0007] Patent CN114790152A discloses a class of 2-cyanoacrylate compounds as shown in the following general formula (B) and specific compounds CK1-CK4. These compounds have good bactericidal activity against Fusarium fungi, but do not mention their inhibitory activity against the production of DON toxin by Fusarium.

[0008]

[0009] Patents CN115005213B, CN115005214B, and CN115039778B disclose the application of combinations of triazole fungicides, succinate dehydrogenase inhibitors, pyrrole fungicides, and compound CK5 in the prevention and control of crop diseases caused by Fusarium. However, they do not mention the inhibitory activity against DON toxin produced by Fusarium. The structural formula of CK5 is shown below.

[0010] Summary of the Invention

[0011] This invention proposes 2-cyanoacrylate compounds represented by formula (I):

[0012]

[0013] In the 2-cyanoacrylate compounds represented by general formula (I) provided by the present invention, R1 and R2 are independently selected from hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, cyano-C1-C6 alkyl, hydroxy-C1-C6 alkyl, C1-C6 alkoxy-C1-C6 alkyl, halo-C1-C6 alkoxy-C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkenyl-C1-C6 alkyl, C2-C6 alkynyl, C2-C6 alkynyl-C1-C6 alkyl, amino-C1-C6 alkyl, C1-C6 alkylamino-C1-C6 alkyl, and C1-C6 dialkylamino-C1-C6 alkyl.

[0014] In a preferred manner, the substituents R1 and R2 are independently selected from hydrogen, C1-C3 alkyl, halo-C1-C3 alkyl, C3-C6 cycloalkyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C3 alkyl, C1-C3 alkoxy-C1-C3 alkyl, and halo-C1-C3 alkoxy-C1-C3 alkyl.

[0015] In a preferred embodiment, the 2-cyanoacrylate compound represented by the above general formula (I) is selected from at least one of the compounds shown in the following structural formulas.

[0016]

[0017]

[0018] As a more preferred embodiment, the 2-cyanoacrylate compound represented by general formula (I) is selected from at least one of the following compounds:

[0019]

[0020] As a further preferred embodiment, the 2-cyanoacrylate compound represented by general formula (I) is selected from at least one of the following compounds.

[0021]

[0022] Index Table 1 lists typical compounds represented by general formula (I), but the typical compounds listed in Index Table 1 do not limit the scope of the present invention.

[0023] Index Table 1

[0024]

[0025]

[0026] Table 2 below shows the NMR data of some of the compounds mentioned in Index Table 1. The compound numbers in Table 2 correspond to the compound numbers in Index Table 1; that is, compound number 1 in Table 2 is the same as compound number 1 in Index Table 1. In Table 2, s represents a singlet, d represents a doublet, dd represents a doublet, t represents a triplet, td represents a triplet-doublet, q represents a quartet, and m represents a multiplet.

[0027] Table 2 NMR data of compounds

[0028]

[0029]

[0030] The present invention also provides a method for preparing 2-cyanoacrylate compounds represented by general formula (I), the method comprising the following steps:

[0031] (1) In an organic solvent, p-fluorophenylacetonitrile reacts with hydrazine hydrate at a temperature of 0–150 °C to obtain the compound shown in formula (II), wherein the organic solvent is selected from at least one of methanol, ethanol, toluene, dichloromethane, acetonitrile, acetone, tetrahydrofuran, dioxane, N,N-dimethylformamide and dimethyl sulfoxide.

[0032]

[0033] (2) In an organic solvent, at a temperature of 0–150 °C, under the action of a reducing agent, the compound shown in formula (II) reacts with an aldehyde to obtain the compound shown in formula (III), wherein the organic solvent is selected from at least one of water, methanol, ethanol, toluene, dichloromethane, acetonitrile, acetone, tetrahydrofuran, dioxane, N,N-dimethylformamide, and dimethyl sulfoxide; the reducing agent is selected from at least one of sodium borohydride, potassium borohydride, sodium cyanoborohydride, borane, hydrogen / palladium on carbon, and hydrogen / Raney nickel; and the aldehyde is selected from at least one of formaldehyde, paraformaldehyde, acetaldehyde, and metaldehyde.

[0034]

[0035] (3) In an organic solvent, at a temperature of 0–150 °C, under the action of an alkali, the compound shown in formula (III) reacts with an alkylating agent to obtain the compound shown in formula (IV), wherein the organic solvent is selected from at least one of methanol, ethanol, toluene, dichloromethane, acetonitrile, acetone, tetrahydrofuran, dioxane, N,N-dimethylformamide, and dimethyl sulfoxide; the alkali is selected from at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, sodium hydride, sodium methoxide, and sodium ethoxide; and the alkylating agent is selected from at least one of fluoroalkanes, bromoalkanes, iodoalkanes, alkyl carbonates, and alkyl sulfates.

[0036]

[0037] (4) Under the action of acid, at a temperature of 0 to 150°C, the compound shown in formula (IV) reacts with ethanol to obtain the compound shown in formula (V), wherein the acid is selected from at least one of concentrated hydrochloric acid, hydrogen chloride gas and acetyl chloride.

[0038]

[0039] (5) In an organic solvent, at a temperature of 0–150 °C, under the action of a base, the compound shown in formula (V) reacts with ethyl cyanoacetate to give the compound shown in formula (I), wherein the organic solvent is selected from at least one of benzene, toluene, xylene, ethanol, acetone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, and N-methylpyrrolidone; and the base is selected from at least one of sodium carbonate, potassium carbonate, cesium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, triethylamine, diisopropylethylamine, and pyridine.

[0040]

[0041] The present invention also provides an application of a 2-cyanoacrylate compound represented by general formula (I), which is suitable for preventing and inhibiting mycotoxin contamination and fungal diseases.

[0042] When the 2-cyanoacrylate compound represented by general formula (I) is used to inhibit mycotoxin contamination, the 2-cyanoacrylate compound represented by general formula (I) is used to inhibit contamination by at least one of the following mycotoxins produced by Fusarium fungi: deoxynivalenol (DON toxin), novofusarenol, 3-acetyldeoxyfusarenol, 15-acetyldeoxynivalenol, T-2 toxin, HT-2 toxin, solanacetic acid fusarenol, monoacetyloxyfusarenol, fusarenol, 15-acetyloxyfusarenyldiol, falconenone, T-2 tetraol, and verrucosporaol.

[0043] When the 2-cyanoacrylate compound represented by general formula (I) is used to control fungal diseases, the 2-cyanoacrylate compound represented by general formula (I) is used to control diseases caused by at least one of Fusarium graminearum, Fusarium moniliforme, Fusarium trifidum, Fusarium noctuida, Fusarium pyrifolium, Fusarium pseudobranchii, Fusarium equisetifolium, Fusarium solanum, and Fusarium oxysporum.

[0044] When the 2-cyanoacrylate compound represented by general formula (I) is used to control fungal diseases, the 2-cyanoacrylate compound represented by general formula (I) is used to control at least one of the following diseases: Fusarium head blight, seedling blight, wilt, root rot, stem rot, and ear rot.

[0045] The present invention also provides a pesticide formulation containing 0.001%-99.99% by weight of a 2-cyanoacrylate compound of general formula (I). The pesticide formulation can be formulated as an emulsifiable concentrate, suspension concentrate, aqueous suspension, microemulsion, (aqueous) emulsion, powder, wettable powder, soluble powder, (water-dispersible) granules, or capsules, etc.

[0046] The pesticide formulation provided by the present invention, in addition to containing 0.001%-99.99% by weight of the 2-cyanoacrylate compound represented by general formula (I), may further contain an agriculturally acceptable carrier.

[0047] The carrier can be solid or liquid. Suitable solid carriers include natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as kaolinite, montmorillonite, and mica; white carbon black, calcium carbonate, and light calcium carbonate; calcium sulfate; limestone; sodium sulfate; and amine salts such as ammonium sulfate and hexamethylethylenediamine. Liquid carriers include water and organic solvents. When water is used as a solvent or diluent, organic solvents can also be used as auxiliaries or antifreeze additives. Suitable organic solvents include aromatic hydrocarbons such as benzene, xylene, and toluene; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, chloroform, and dichloromethane; aliphatic hydrocarbons such as petroleum fractions, cyclohexane, and light mineral oils; alcohols such as isopropanol, butanol, ethylene glycol, glycerol, and cyclohexanol; their ethers and esters; and ketones such as acetone, cyclohexanone, dimethylformamide, and N-methylpyrrolidone.

[0048] The carrier can also be a surfactant. Suitable surfactants can be emulsifiers, dispersants, or wetting agents; they can be ionic or nonionic. Examples of nonionic emulsifiers include polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty amines, and commercially available emulsifiers such as Agricultural Emulsion 2201B, Agricultural Emulsion 0203B, and Agricultural Emulsion 100. # 500g of agricultural dairy products # 600g of agricultural dairy products # 600-2 Agricultural Milk # Agricultural Milk 1601, Agricultural Milk 2201, Agricultural Milk NP-10, Agricultural Milk NP-15, Agricultural Milk 507 # Agricultural Milk OX-635, Agricultural Milk OX-622, Agricultural Milk OX-653, Agricultural Milk OX-667, Ningru 36 # Dispersants include sodium lignosulfonate, dispersing agents, calcium lignosulfonate, and methylnaphthalenesulfonic acid formaldehyde condensate. Wetting agents include sodium lauryl sulfate, sodium dodecylbenzenesulfonate, and sodium alkylnaphthalenesulfonate.

[0049] The present invention also provides a method for sterilization, the method comprising: preparing a pesticide formulation from a 2-cyanoacrylate compound of general formula (I) and applying it to the pathogen to be controlled or its growth medium. When the pesticide formulation from the 2-cyanoacrylate compound of general formula (I) is applied to the pathogen to be controlled or its growth medium, the application rate is 10 to 1000 grams per hectare.

[0050] The beneficial effects of this invention are as follows:

[0051] This invention provides a novel 2-cyanoacrylate compound that effectively inhibits mycotoxin contamination produced by Fusarium fungi and exhibits excellent fungicidal activity against Fusarium fungi. Therefore, this compound can be used to prepare fungicides in the agricultural field, offering advantages such as high efficiency, safety, and environmental friendliness. Detailed Implementation

[0052] The present invention will be further described below with reference to specific embodiments, but the invention is not limited to these specific embodiments. Those skilled in the art should recognize that the present invention covers all alternatives, improvements, and equivalents that may be included within the scope of the claims.

[0053] I. Compound Preparation

[0054] Example 1: Synthesis of Compound 2

[0055] Step 1: Synthesis of intermediate 2a

[0056]

[0057] 5.0 g of p-fluorobenzonitrile, 5.2 g of hydrazine hydrate, and 30 mL of ethanol were added to a reaction flask, and the mixture was heated under reflux for 8 h. After the reaction was complete, water was added, and the mixture was extracted three times with EA. The organic phases were combined, dried over anhydrous MgSO4, filtered, and the filtrate was distilled under reduced pressure to give 4.0 g of intermediate 2a, with a yield of 60%.

[0058] Step 2: Synthesis of intermediate 2b

[0059]

[0060] At room temperature, a methanol solution containing 0.98 g NaBH3CN and 0.94 g ZnCl2 was added dropwise to a 35 ml methanol solution containing 1.57 g intermediate 2a and 3.82 g 37% formaldehyde aqueous solution, and the mixture was stirred overnight at room temperature. After the reaction was complete, a 0.1 mol / L NaOH aqueous solution was added, and the mixture was extracted three times with EA. The organic phases were combined, washed successively with water and saturated NaCl aqueous solution, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated and separated by column chromatography (eluent: EA:PE = 1:8) to obtain 0.45 g intermediate 2b, with a yield of 24.2%.

[0061] Step 3: Synthesis of intermediate 2c

[0062]

[0063] Add 0.14 g of NaH (60%) to a round-bottom flask, then add 5 ml of DMF and 0.45 g of intermediate 2b under ice bath conditions, and stir at room temperature for 15 min. Add 0.475 g of iodomethane dropwise, and stir at room temperature for 6 h. After the reaction is complete, quench the reaction with water, extract three times with EA, combine the organic phases, wash once with water, dry with anhydrous MgSO4, filter, concentrate the filtrate, and separate by column chromatography (eluent: EA:PE = 1:4) to obtain 0.42 g of intermediate 2c, with a yield of 85.3%.

[0064] Step 4: Synthesis of intermediate 2d

[0065]

[0066] 1.0 g of anhydrous ethanol and 0.2 g of intermediate 2c were added to a round-bottom flask. 1.08 g of acetyl chloride was added dropwise under ice bath conditions, and the mixture was stirred at room temperature for 6 h. After the reaction was complete, the mixture was concentrated under reduced pressure, neutralized with saturated NaHCO3 aqueous solution, extracted three times with EA, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated to give 0.25 g of intermediate 2d, with a yield of 99.0%.

[0067] Step 5: Synthesis of Compound 2

[0068]

[0069] 0.25 g of intermediate 2d, 1.28 g of ethyl cyanoacetate, 0.12 g of triethylamine, and 6 mL of anhydrous ethanol were added to a pressure tube and the mixture was heated to 100 °C for 8 h. After the reaction was completed, the mixture was desolvated under reduced pressure and separated by column chromatography (eluent: EA:PE = 1:3) to give 0.11 g of compound 2, with a yield of 33.8%.

[0070] Example 2: Synthesis of Compound 13

[0071] Step 1: Synthesis of intermediate 13b

[0072]

[0073] At room temperature, a methanol solution containing 1.26 g NaBH3CN and 1.37 g ZnCl2 was added dropwise to a methanol solution (50 ml) containing 2.0 g intermediate 2a and 6.62 g 40% acetaldehyde aqueous solution, and the mixture was stirred overnight at room temperature. After the reaction was complete, 0.1 N NaOH aqueous solution was added, and the mixture was extracted three times with EA. The combined organic phases were washed successively with water and saturated NaCl aqueous solution, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated and separated by column chromatography (eluent: EA:PE = 1:8) to obtain 0.65 g intermediate 13b, with a yield of 22.8%.

[0074] Step 2: Synthesis of intermediate 13c

[0075]

[0076] 0.17 g of NaH (60%) was added to a round-bottom flask, followed by 6 ml of DMF and 0.65 g of intermediate 13b under ice bath conditions. The mixture was stirred at room temperature for 15 min. Then, 0.45 g of bromoethane was added dropwise, and the mixture was stirred at room temperature for 6 h. After the reaction was complete, the reaction was quenched with water, extracted three times with EA, and the combined organic phases were washed once with water, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated and separated by column chromatography (eluent: EA:PE = 1:4) to obtain 0.68 g of intermediate 13c, with a yield of 91.1%.

[0077] Step 3: Synthesis of intermediate 13d

[0078]

[0079] 1.0 g of anhydrous ethanol and 0.2 g of intermediate 13c were added to a round-bottom flask. 0.87 g of acetyl chloride was added dropwise under ice bath conditions, and the mixture was stirred at room temperature for 6 h. After the reaction was complete, the mixture was concentrated under reduced pressure, neutralized with saturated NaHCO3 aqueous solution, extracted three times with EA, dried over anhydrous and MgSO4-free conditions, filtered, and the filtrate was concentrated to give 0.24 g of intermediate 13d, with a yield of 99.2%.

[0080] Step 4: Synthesis of Compound 13

[0081]

[0082] 0.24 g of intermediate 13d, 1.03 g of ethyl cyanoacetate, 0.09 g of triethylamine, and 6 mL of anhydrous ethanol were added to a pressure tube and the mixture was heated to 100 °C for 8 h. After the reaction was completed, the mixture was desolvated under reduced pressure and separated by column chromatography (eluent: EA:PE = 1:3) to give 0.12 g of compound 13, with a yield of 40.0%.

[0083] II. Formulation Preparation

[0084] Examples 3 to 7 below provide practical examples of the formulation of several bactericide formulations using the compound (I) of the present invention as the active ingredient. It should be noted that the present invention is not limited to the scope of the examples below. In these formulation examples, all "%" refer to weight percentage.

[0085] Example 3: Wettable Powder Formulation

[0086] 10% of compound (I) (index table 1) and 5% of lignin sulfonate (M) q 1%, 1% lauryl alcohol polyoxyethylene ether (JFC), 40% diatomaceous earth and 44% light calcium carbonate are uniformly mixed and pulverized to obtain a wettable powder.

[0087] Example 4, Emulsifiable Concentrate Formulation

[0088] The emulsifiable concentrate is prepared by heating and stirring 10% of compound (I) (index table 1), 5% of agricultural emulsion No. 500 (calcium salt), 5% of agricultural emulsion No. 602, 5% of N-methyl-2-pyrrolidone and 75% of xylene until homogeneous.

[0089] Example 5, Granule Formulation

[0090] Mix 5% of compound (I) (index table 1), 1% of polyvinyl alcohol (PVA), 4% of sodium naphthalene sulfonate formaldehyde condensate (NMO) and 90% of clay evenly, pulverize, then add 20 parts of water to this 100 parts mixture, knead, and use an extruder to make 14-32 mesh granules, dry, and obtain granules.

[0091] Example 6: Formulation of water-dispersible granules

[0092] 20% of compound (I) (index table 1), 4% naphthalene sulfonate formaldehyde condensate, 1% naphthalene sulfonate, 2% silica, and 73% kaolin are mixed and pulverized. Water is then added and kneaded, followed by granulation in a granulator equipped with a sieve of a specific size. The granules are then dried and sieved (according to the sieve size range) to obtain the final granular product.

[0093] Example 7: Formulation of aqueous suspension agent

[0094] 20% of compound (I) (index table 1), 1% fatty alcohol polyoxyethylene ether, 3% rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, 1% magnesium aluminum silicate, 0.4% organosilicon defoamer, 5% propylene glycol and deionized water (69.5%) are premixed evenly, then added to a sand mill for sand milling, filtered to obtain a suspension mother liquor, and then added to a prepared xanthan gum (0.1%) aqueous solution and sheared and mixed evenly.

[0095] III. Activity Test

[0096] Examples of bioactivity assays using compounds of the present invention are given below. It should be noted that the present invention is not limited to the examples described below.

[0097] Example 8: Test for Inhibition of DON Toxin

[0098] Fusarium graminearum strains were cultured in TBI medium at 28°C in the dark for 7 days. After adding a certain concentration of the test compound, the culture was carried out for 24 hours. The mixture was then filtered through filter paper, and the filtrate was used to determine the DON content. The mycelia on the filter paper were dried and weighed as an internal control. The DON content was detected using a DON assay kit (Wis008).

[0099] This invention evaluated the inhibitory effect of the compounds listed in Index Table 1 on DON toxin. The results showed that the compounds of this invention have excellent inhibitory effects on DON toxin produced by Fusarium graminearum. "μg / g dry mycelium" refers to each microgram of DON toxin per gram of dry mycelium. CK1-CK5, cyazofamid, and carbendazim were used as control agents, as detailed below:

[0100] At a concentration of 0.5 mg / L, the DON toxin content after treatment with compounds 1, 2, 11, and 12 was less than 100 μg / g dry mycelium, while the DON toxin content after treatment with control agents CK1-CK5 was approximately 200-300 μg / g dry mycelium, the DON toxin content after treatment with the control agent cyazofamid was 600 μg / g dry mycelium, and the DON toxin content after treatment with the control agent carbendazim was 6800 μg / g dry mycelium.

[0101] At a concentration of 0.25 mg / L, the DON toxin content after treatment with compounds 1 and 2 was less than 400 μg / g dry mycelium, while the DON toxin content after treatment with control agents CK1-CK5 was approximately 800-1200 μg / g dry mycelium, the DON toxin content after treatment with the control agent cyazofamid was 1600 μg / g dry mycelium, and the DON toxin content after treatment with the control agent carbendazim was 7000 μg / g dry mycelium.

[0102] Example 9: Indoor Activity Assay Test

[0103] The inhibitory activity of the test compound against the test pathogen was determined using the mycelial growth rate method. The test pathogen was placed on a PDA plate. Once the growth rate reached the logarithmic phase, 0.5 cm diameter mycelial blocks were punched at the edge of fresh colonies and inoculated onto a PDA plate containing a certain concentration of the test compound. Simultaneously, mycelial blocks were inoculated onto PDA medium without the test compound as a control. The plates were incubated at 25°C for 2-3 days. After the test pathogen had completely covered the plate, photographs were taken, and the colony diameter was measured using the cross-sectional method. The mycelial growth inhibition rate (MGIR) was calculated using the following formula: MGIR% = [(CN) / C] × 100%, where C is the colony diameter of the control group and N is the colony diameter of the treated group. The experiment was repeated twice, with two plates per replicate. The test pathogen was *Fusarium graminearum*.

[0104] This invention evaluated the in vitro bactericidal activity of the compounds listed in Index Table 1. The results showed that the compounds of this invention have excellent bactericidal activity against Fusarium graminearum. "mg / L" refers to milligrams of active ingredient per liter. CK1-CK5 and cyazofamid were used as control agents, as detailed below:

[0105] At a concentration of 0.125 mg / L, compounds 1, 2, 3, 11, and 12 all exhibited a greater than 90% inhibition rate against the mycelial growth of Fusarium graminearum, comparable to the activity of the control agents CK1-CK5, and significantly higher than that of the control agent cyazofamid.

[0106] At a concentration of 0.0625 mg / L, compounds 1 and 2 both exhibited a greater than 90% inhibition rate on the mycelial growth of Fusarium graminearum, comparable to the control agents CK4 and CK5, slightly higher than the control agents CK1-CK3, and significantly higher than the control agent cyazofamid.

Claims

1. A 2-cyanoacrylate compound represented by general formula (I): in: R1 and R2 are independently selected from hydrogen and C1-C6 alkyl groups.

2. The 2-cyanoacrylate compound according to claim 1, characterized by: In the 2-cyanoacrylate compounds represented by general formula (I): R1 and R2 are independently selected from hydrogen and C1-C3 alkyl groups.

3. The 2-cyanoacrylate compound according to claim 2, characterized by: The 2-cyanoacrylate compounds represented by general formula (I) are selected from at least one of the following compounds:

4. A method for preparing a 2-cyanoacrylate compound according to any one of claims 1-3 of general formula (I), comprising the following steps: (1) In an organic solvent, p-fluorophenylacetonitrile reacts with hydrazine hydrate to give the compound shown in formula (II): (2) In an organic solvent, under the action of a reducing agent, the compound shown in formula (II) reacts with an aldehyde to give the compound shown in formula (III): (3) In an organic solvent, under alkaline conditions, the compound shown in formula (III) reacts with an alkylating agent to give the compound shown in formula (IV): (4) Under acidic conditions, the compound shown in formula (IV) reacts with ethanol to give the compound shown in formula (V): (5) In an organic solvent, under alkaline conditions, the compound shown in formula (V) reacts with ethyl cyanoacetate to give the compound shown in formula (I):

5. Use of a 2-cyanoacrylate compound according to any one of claims 1 to 3, characterized in that: The 2-cyanoacrylate compounds are used to inhibit mycotoxin contamination.

6. The use of the 2-cyanoacrylate compound according to claim 5, characterized in that: The 2-cyanoacrylate compounds are used to inhibit contamination by Fusarium toxins.

7. The use of the 2-cyanoacrylate compound according to claim 6, characterized in that: The falcin fungal toxin is at least one of the following: deoxynivalenol, novofusarenol, 3-acetyldeoxyfusarenol, 15-acetyldeoxynivalenol, T-2 toxin, HT-2 toxin, neosolaniformis falcinol, monoacetyloxyfusarenol, vesicarcinol, 15-acetyloxyfusarenil diol, falcinone, T-2 tetraol, or verrucosporinol.

8. The use of the 2-cyanoacrylate compound according to claim 7, characterized in that: The falcatella toxin is at least one of deoxynivalenol, novofusarenol, or 3-acetyldeoxyfusarenol.

9. A pesticidal formulation, characterized by: The pesticide formulation contains 0.001% to 99.99% by weight of a 2-cyanoacrylate compound of any one of the general formulas (I) of claims 1-3.

10. A method of disinfecting, characterized by: The sterilization method includes applying the pesticide formulation of claim 9 to the pathogens or growth medium that need to be controlled, with an effective application rate of 10 to 1000 grams per hectare.

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