2-cyanoacrylate compound and application thereof

Abstract

The invention discloses a 2-cyanoacrylate compound represented by a general formula (I): # imgabs0 #, wherein each substituent group is shown in the specification. The invention also discloses a preparation method and application of the 2-cyanoacrylate compound. The 2-cyanoacrylate compound is suitable for inhibiting fungaltoxin and pollution, and preventing and treating diseases caused by fungi.

Description

Technical Field

[0001] The invention belongs to the field of agricultural fungicides, and specifically relates to a 2-cyanoacrylate compound and an application thereof in preventing and controlling diseases caused by fungi and inhibiting fungal toxin pollution. Background Art

[0002] Wheat fusarium head blight is a common disease caused by Fusarium graminearum. It not only reduces wheat production on a large scale, but also seriously affects its quality, causing significant economic losses. It has become the primary disease affecting high and stable wheat production in my country. When Fusarium graminearum infects wheat, it produces deoxynivalenol (DON) toxin in wheat grains. The toxin has strong cytotoxicity, obvious embryotoxicity and teratogenicity, and widely contaminates wheat and its products, grain and oil food, and feed, etc., seriously threatening food safety, human and animal health. At present, 37 countries in the world have formulated relevant limit standards for DON toxins in food or grains. my country's national standard GB2761-2011 stipulates that the limit standard for DON toxins in grains and grain products is 1 mg / kg. Some existing fungicides, such as carbendazim, prochloraz, myclobutanil, and pyraclostrobin, although their use can reduce diseases, stimulate the production of DON toxins at the same time. Therefore, agricultural fungicides used to prevent and control wheat fusarium wilt are required to not only effectively control the fusarium wilt disease, but also reduce the DON toxin content in wheat grains.

[0003] 2-Cyanoacrylate compounds have been highly valued in the field of pesticide creation due to their herbicidal, antifungal, and anti-plant virus pesticide activities. For example, the representative fungicide cyanoacrylate can not only effectively prevent and treat diseases such as wheat fusarium head blight and rice seedling blight, but also effectively reduce the pollution of DON toxins.

[0004] Patent CN104068025B discloses the use of a cyanobacterium-butyl and prothioconazole combination in preventing and controlling fusarium head blight and fusarium head blight toxin contamination in crops. The combined use can significantly inhibit the formation of fusarium head blight toxins.

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

[0006]

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

[0008]

[0009] Patents CN115005213B, CN115005214B, and CN115039778B respectively disclose the use of a combination of triazoles, succinate dehydrogenase inhibitors, pyrrole fungicides, and compound CK5 in preventing and controlling crop diseases caused by Fusarium, but do not mention the inhibitory activity against the production of DON toxin by Fusarium. The structural formula of CK5 is shown below.

[0010] Summary of the invention

[0011] The present invention provides a 2-cyanoacrylate compound represented by the following formula (I):

[0012]

[0013] In the 2-cyanoacrylate compounds represented by the general formula (I) provided by the present invention, R1 and R2 are independently selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, cyano C1-C6 alkyl, hydroxy C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, halogenated 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] As a preferred embodiment, the substituents R1 and R2 are independently selected from hydrogen, C1-C3 alkyl, halogenated C1-C3 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C3 alkoxyC1-C3 alkyl, halogenated C1-C3 alkoxyC1-C3 alkyl.

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

[0016]

[0017]

[0018] As a more preferred embodiment, the 2-cyanoacrylate compound represented by the 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 the 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 described in Index Table 1 do not limit the scope of the present invention.

[0023] Index Table 1

[0024]

[0025]

[0026] The following Table 2 is the NMR data of some compounds described in Index Table 1. The compound numbers described in Table 2 correspond to the compound numbers described in Index Table 1, that is, the compound of compound number 1 described in Table 2 is consistent with the compound of compound number 1 described in Index Table 1. In Table 2, s is a singlet, d is a doublet, dd is a doublet, t is a triplet, td is a triplet of doublets, q is a quartet, and m is a multiplet.

[0027] Table 2 NMR data of compounds

[0028]

[0029]

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

[0031] (1) In an organic solvent, at a temperature of 0 to 150° C., p-fluorophenylacetonitrile is reacted with hydrazine hydrate to obtain a compound represented by 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 to 150° C., in the presence of a reducing agent, the compound represented by formula (II) reacts with an aldehyde to obtain a compound represented by 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 carbon, and hydrogen / Raney nickel; and the aldehyde is selected from at least one of formaldehyde, paraformaldehyde, acetaldehyde, and paraldehyde.

[0034]

[0035] (3) In an organic solvent at a temperature of 0 to 150° C., in the presence of a base, the compound represented by formula (III) reacts with an alkylating agent to obtain a compound represented by 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 base 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) In the presence of an acid at a temperature of 0 to 150° C., the compound represented by formula (IV) reacts with ethanol to obtain the compound represented by 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 to 150° C., in the presence of a base, the compound represented by formula (V) reacts with ethyl cyanoacetate to obtain the compound represented by 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). The 2-cyanoacrylate compound represented by general formula (I) is suitable for preventing and controlling fungal toxin pollution and fungal diseases.

[0042] When the 2-cyanoacrylate compound represented by the general formula (I) is used to inhibit fungal toxin contamination, the 2-cyanoacrylate compound represented by the general formula (I) is used to inhibit the contamination of at least one of the fungal toxins produced by Fusarium fungi, including deoxynivalenol (DON toxin), nivalenol, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, T-2 toxin, HT-2 toxin, neofusarium, monoacetoxyfusarium, fusarium, 15-acetoxyfusariumdiol, fusariumenone, T-2 tetraol and verrucosporin.

[0043] When the 2-cyanoacrylate compound represented by the general formula (I) is used to prevent and control fungal diseases, the 2-cyanoacrylate compound represented by the general formula (I) is used to prevent and control diseases caused by at least one of Fusarium graminearum, Fusarium moniliforme, Fusarium trilineatum, Fusarium nivalis, Fusarium pyrifolium, Fusarium pseudosporum, Fusarium equisetum, Fusarium solani, and Fusarium oxysporum.

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

[0045] The present invention also provides a pesticide preparation, which contains 0.001%-99.99% by weight of the 2-cyanoacrylate compound represented by the general formula (I). The pesticide preparation can be formulated into emulsifiable concentrates, suspensions, aqueous suspensions, microemulsions, (water) emulsions, powders, wettable powders, soluble powders, (water-dispersible) granules or capsules, etc.

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

[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, kaolin, montmorillonite and mica; white carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; amine salts such as ammonium sulfate and hexamethylenediamine. Liquid carriers include water and organic solvents. When water is used as a solvent or diluent, organic solvents can also be used as adjuvants or antifreeze additives. Suitable organic solvents include aromatic hydrocarbons such as benzene, xylene, toluene, etc.; chlorinated hydrocarbons such as chlorobenzene, vinyl chloride, chloroform, dichloromethane, etc.; aliphatic hydrocarbons such as petroleum fractions, cyclohexane, light mineral oil; alcohols such as isopropanol, butanol, ethylene glycol, glycerol and cyclohexanol, etc.; and their ethers and esters; and ketones such as acetone, cyclohexanone, dimethylformamide and N-methyl-pyrrolidone.

[0048] The carrier may also be a surfactant. Suitable surfactants may be emulsifiers, dispersants or wetting agents; they may be ionic or nonionic. Nonionic emulsifiers include polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty amines, and commercially available emulsifiers: Nongru 2201B, Nongru 0203B, Nongru 100 # 、Nongru 500 # 、Nongru 600 # 、Nongru 600-2 # 、Nongru 1601、Nongru 2201、Nongru NP-10、Nongru NP-15、Nongru 507 # 、Nongru OX-635、Nongru OX-622、Nongru OX-653、Nongru OX-667、Ningru 36 # Dispersants include sodium lignin sulfonate, pull-open powder, calcium lignin sulfonate, methyl naphthalene sulfonic acid formaldehyde condensate, etc. Wetting agents include sodium lauryl sulfate, sodium dodecylbenzene sulfonate, sodium alkyl naphthalene sulfonate, etc.

[0049] The present invention also provides a sterilization method, which comprises: preparing the above-mentioned pesticide preparation from the 2-cyanoacrylate compound represented by the general formula (I) and applying it to the pathogens to be controlled or the medium in which they grow. When the 2-cyanoacrylate compound represented by the general formula (I) is prepared into the pesticide preparation and applied to the pathogens to be controlled or the medium in which they grow, the application amount is 10 to 1000 grams per hectare.

[0050] The present invention has the following beneficial effects:

[0051] The present invention provides a novel 2-cyanoacrylate compound, which can effectively inhibit the mycotoxin pollution produced by Fusarium fungi and has good fungicidal activity against Fusarium fungi. Therefore, the compound can be used to prepare fungicides in the agricultural field, and has the advantages of high efficiency, safety and environmental friendliness. DETAILED DESCRIPTION

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

[0053] 1. 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 the reaction flask and heated under reflux for 8 h. After the reaction, water was added and EA was extracted three times. The organic phases were combined, dried over anhydrous MgSO4, filtered, and the filtrate was distilled under reduced pressure to obtain 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 (35 ml) containing 0.98 g NaBH3CN and 0.94 g ZnCl2 was added dropwise to a methanol solution (35 ml) containing 1.57 g intermediate 2a and 3.82 g 37% formaldehyde aqueous solution, and the mixture was stirred at room temperature overnight. After the reaction was completed, a 0.1 mol / L NaOH aqueous solution was added, and EA was extracted three times. The organic phases were combined, washed with water and a saturated NaCl aqueous solution in sequence, 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] 0.14 g NaH (60%) was added to a round-bottom flask, and DMF (5 ml) and 0.45 g intermediate 2b were added under ice bath, and stirred at room temperature for 15 min. 0.475 g iodomethane was added dropwise, and stirred at room temperature for 6 h. After the reaction was completed, water was added to quench the reaction, and EA was extracted three times. The organic phases were combined and 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 0.42 g 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, and stirred at room temperature for 6 h. After the reaction was completed, the mixture was concentrated under reduced pressure, neutralized by adding saturated NaHCO3 aqueous solution, extracted with EA three times, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated to obtain 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 heated at 100°C for 8 h. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography (eluent: EA:PE = 1:3) to obtain 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 (50 ml) 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 stirred at room temperature overnight. After the reaction was completed, a 0.1 N NaOH aqueous solution was added, and EA was extracted three times. The organic phases were combined, washed with water and a saturated NaCl aqueous solution in sequence, 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 NaH (60%) was added to a round-bottom flask, and DMF (6 ml) and 0.65 g intermediate 13b were added under ice bath, and stirred at room temperature for 15 min. 0.45 g ethyl bromide was added dropwise, and stirred at room temperature for 6 h. After the reaction was completed, water was added to quench the reaction, and EA was extracted three times. The organic phases were combined and 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 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, and stirred at room temperature for 6 h. After the reaction was completed, the mixture was concentrated under reduced pressure, neutralized by adding saturated NaHCO3 aqueous solution, extracted with EA three times, dried over anhydrous MgSO4, filtered, and the filtrate was concentrated to obtain 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 heated at 100°C for 8 h. After the reaction was completed, the solvent was removed under reduced pressure and separated by column chromatography (eluent: EA:PE = 1:3) to obtain 0.12 g of compound 13 with a yield of 40.0%.

[0083] 2. Preparation

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

[0085] Embodiment 3, wettable powder formulation

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

[0087] Embodiment 4, emulsifiable concentrate formula

[0088] Heat and stir 10% of compound (I) (Index Table 1), 5% of Nongru No. 500 (calcium salt), 5% of Nongru No. 602, 5% of N-methyl-2-pyrrolidone and 75% of xylene to obtain an emulsifiable concentrate.

[0089] Embodiment 5, granule formulation

[0090] 5% of compound (I) (Index Table 1), 1% of polyvinyl alcohol (PVA), 4% of sodium naphthalenesulfonate formaldehyde condensate (NMO) and 90% of clay are uniformly mixed and crushed, and then 20 parts of water are added to 100 parts of the mixture, kneaded, and made into 14-32 mesh granules using an extruder granulator, and dried to obtain granules.

[0091] Example 6, water dispersible granule formulation

[0092] 20% of compound (I) (Index Table 1), 4% of naphthalenesulfonate formaldehyde condensate, 1% of naphthalenesulfonate, 2% of white carbon black and 73% of kaolin are mixed and ground, and then water is added and kneaded, and then added into a granulator equipped with a screen of a certain specification for granulation. Then, it is dried and sieved (according to the range of the screen) to obtain a granular product.

[0093] Embodiment 7, aqueous suspension formulation

[0094] 20% of compound (I) (Index Table 1), 1% of fatty alcohol polyoxyethylene ether, 3% of rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, 1% of magnesium aluminum silicate, 0.4% of silicone defoamer, 5% of propylene glycol and deionized water (69.5%) are pre-mixed and then added to a sand mill for sand grinding. After filtering, a suspension mother liquor is obtained, and the prepared xanthan gum (0.1%) aqueous solution is added for shear mixing.

[0095] 3. Activity Test

[0096] The following are examples of biological activity assays using the compounds of the present invention. It should be noted that the present invention is not limited to the following examples.

[0097] Example 8: DON toxin inhibition test

[0098] The Fusarium graminearum strain was cultured in TBI medium at 28°C in the dark for 7 days, and then a certain concentration of the test compound was added and cultured for 24 hours. The filtrate was then filtered with filter paper, and the filtrate was used to determine the DON content. The mycelium on the filter paper was dried and weighed as an internal reference, and the DON content was detected using a DON assay reagent (Wisai Technology, Wis008) kit.

[0099] The present invention evaluates the DON toxin inhibitory effect of the numbered compounds described in Index Table 1. The results show that the compounds of the present invention have excellent inhibitory effect on the DON toxin produced by Fusarium graminearum. "μg / g dry mycelium" refers to micrograms of DON toxin / gram of dry mycelium. CK1-CK5, cyanothiocarb, and carbendazim are used as control agents, as follows:

[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, the DON toxin content after treatment with control agents CK1-CK5 was about 200-300 μg / g dry mycelium, the DON toxin content after treatment with control agent cyanothiocarb was 600 μg / g dry mycelium, and the DON toxin content after treatment with 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, the DON toxin content after treatment with control agents CK1-CK5 was about 800-1200 μg / g dry mycelium, the DON toxin content after treatment with the control agent cyanoacrylate 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 measurement test

[0103] The mycelium growth rate method was used to determine the inhibitory activity of the test compound on the test pathogen. The test pathogen was placed on a PDA plate. When the growth rate reached the logarithmic phase, a 0.5 cm diameter bacterial block was punched at the edge of the fresh colony with a hole puncher and inoculated onto a PDA plate containing a certain concentration of the test compound. At the same time, the bacterial block was inoculated into a PDA medium without the test drug as a control. Cultured in a 25°C incubator for 2-3 days, when the test pathogens grew all over the plate, photographed it, and the colony growth diameter was measured using the cross method. The mycelium 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 2 dishes each time. The test pathogen was Fusarium graminearum.

[0104] The present invention evaluates the in vitro fungicidal activity of the numbered compounds described in Index Table 1. The results show that the compounds of the present invention have good fungicidal activity against Fusarium graminearum. "mg / L" refers to milligrams of active substance per liter. CK1-CK5 and cyanothiocarb are used as control agents. The specific results are as follows:

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

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

Claims

1. A 2-cyanoacrylate compound represented by general formula (I): in: R1 and R2 are independently selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, cyanoC1-C6 alkyl, hydroxyC1-C6 alkyl, C1-C6 alkoxyC1-C6 alkyl, halogenated C1-C6 alkoxyC1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkenylC1-C6 alkyl, C2-C6 alkynyl, C2-C6 alkynylC1-C6 alkyl, aminoC1-C6 alkyl, C1-C6 alkylaminoC1-C6 alkyl, C1-C6 dialkylaminoC1-C6 alkyl.

2. The 2-cyanoacrylate compound according to claim 1, characterized in that: In the 2-cyanoacrylate compound represented by the general formula (I): R1 and R2 are independently selected from hydrogen, C1-C3 alkyl, halogenated C1-C3 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C3 alkyl, C1-C3 alkoxyC1-C3 alkyl, halogenated C1-C3 alkoxyC1-C3 alkyl.

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

4. The 2-cyanoacrylate compound of general formula (I) according to any one of claims 1 to 3, characterized in that: The preparation method of the 2-cyanoacrylate compound comprises the following steps: (1) In an organic solvent, p-fluorophenylacetonitrile reacts with hydrazine hydrate to obtain a compound represented by formula (II): (2) In an organic solvent, in the presence of a reducing agent, the compound represented by formula (II) reacts with an aldehyde to obtain a compound represented by formula (III): (3) In an organic solvent, in the presence of a base, the compound represented by formula (III) reacts with an alkylating agent to obtain a compound represented by formula (IV): (4) Under the action of an acid, the compound represented by formula (IV) reacts with ethanol to obtain a compound represented by formula (V): (5) In an organic solvent, in the presence of a base, the compound represented by formula (V) reacts with ethyl cyanoacetate to obtain a compound represented by formula (I):

5. The use of the 2-cyanoacrylate compound according to any one of claims 1 to 3, characterized in that: The 2-cyanoacrylate compound is used for inhibiting the contamination of fungal toxins.

6. The use of the 2-cyanoacrylate compound according to claim 5, characterized in that: The 2-cyanoacrylate compound is used for inhibiting the contamination of Fusarium fungus toxin.

7. The use of the 2-cyanoacrylate compound according to claim 6, characterized in that: The Fusarium fungal toxins include at least one of deoxynivalenol, nivalenol, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol, T-2 toxin, HT-2 toxin, neophytotoxin, monoacetoxyfusarium, fusarium alcohol, 15-acetoxyfusarium diol, fusarenone, T-2 tetraol or verrucosporin.

8. The use of the 2-cyanoacrylate compound according to claim 7, characterized in that: The Fusarium fungal toxin includes at least one of deoxynivalenol, nivalenol or 3-acetyldeoxynaphthalenol.

9. A pesticide preparation, characterized in that: The pesticide preparation contains 0.001%-99.99% by weight of the 2-cyanoacrylate compound represented by the general formula (I) according to any one of claims 1 to 3.

10. A sterilization method, characterized in that: The sterilization method comprises: applying the pesticide preparation according to claim 9 to the pathogens to be controlled or the growth medium, with the effective application amount being 10 to 1000 grams per hectare.

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