2-cyano-3-disubstituted phenyl acrylate compound, preparation method thereof and application of 2-cyano-3-disubstituted phenyl acrylate compound in pesticide

Abstract

The invention belongs to the field of pesticides, and relates to a 2-cyano-3-disubstituted phenyl acrylate compound as well as a preparation method and application thereof in pesticides. Carrying out alcoholysis reaction on the benzonitrile compound a and a hydrogen chloride absolute ethyl alcohol solution to obtain an intermediate b; carrying out condensation reaction on the intermediate b and ethyl cyanoacetate under the action of alkali to obtain an intermediate c; the intermediate c and a substituted compound are subjected to a substitution reaction under the action of alkali and a catalyst, and the 2-cyano-3-disubstituted phenyl acrylate compound I is obtained. The 2-cyano-3-disubstituted phenylacrylate compound provided by the invention has good bactericidal activity, and has relatively high bactericidal activity on pathogenic bacteria of chlorosclerotium, fusarium, acrocyst, colletotrichum, cercospora, verticillium and black beancurd skin; the compound can be used for preparing bactericides in the fields of agriculture, horticulture, industry and the like, and has the advantages of broad spectrum, high efficiency, low toxicity and environmental friendliness.

Description

Technical Field

[0001] The invention belongs to the field of pesticides and relates to a 2-cyano-3-disubstituted phenyl acrylate compound and a preparation method thereof and application thereof in pesticides. Background Art

[0002] Acrylate derivatives have certain biological activities, and their structures have the potential for scalability and structural modification. Therefore, they are one of the current targets for the development of new pesticides, and a series of progress has been made in recent years.

[0003] Patent document CN1160318C discloses a class of 2-cyano-3-substituted phenyl acrylate compounds represented by the following general formula (A), which have preventive effects on various diseases caused by Fusarium such as wheat fusarium rust, among which the highest inhibition rate on wheat fusarium rust is 91.3% under 0.5 mg / mL conditions.

[0004]

[0005] Patent document CN101381326A discloses a class of 2-cyano 3-(substituted)amino-3-phenylacrylate compounds as shown in the following general formula (B), which have a control effect on Fusarium, and the highest inhibition rate of wheat fusarium under 2 μg / mL conditions is 100%.

[0006]

[0007] Patent document CN109879841B discloses a class of (Z)-3-imino-1-propenol compounds represented by the following general formula (C), which have a preventive and therapeutic effect on wheat fusarium rust that causes plant diseases and can reduce the production of wheat fusarium rust toxin (DON), wherein the highest inhibition rate of wheat fusarium rust under 1 mg / mL conditions is 91.8%.

[0008]

[0009] Patent document CN109867623B discloses a class of 3-pyridyl-3-amino-2-cyanoacrylate compounds as shown in the following general formula (D), which have a preventive and therapeutic effect on wheat fusarium head blight, wherein the highest inhibition rate of wheat fusarium head blight is 90.90% under 20 mg / L conditions.

[0010]

[0011] Patent document CN114790152A discloses a class of 2-cyanoacrylate compounds represented by the following general formula (E), which have a control effect on Fusarium fungi, wherein the highest inhibition rate against wheat fusarium head blight is 94.8% under the condition of 0.125 mg / L.

[0012]

[0013] Patent document CN115005214A discloses a fungicide composition, wherein the active ingredient thereof has a compound (ZJS178) of formula (F), which has a control effect on Fusarium fungi, wherein EC 50 The value is 0.0379μg / mL.

[0014]

[0015] Cyanostrobin, i.e. (Z)-2-cyano-3-amino-3-phenyl ethyl acrylate, is a successfully developed fungicide that has excellent control effects on some Fusarium crop diseases and can significantly reduce the toxins produced by these diseases that are extremely harmful to the human body. Cyanostrobin has a completely different mechanism of action from other fungicides, and its target is myosin-5. However, the spectrum of action of cyanostrobin is very narrow, and the dosage used does not reach a very efficient level. Therefore, the development of a broad-spectrum, efficient pesticide fungicide has important application value and economic value. Summary of the invention

[0016] The technical problem to be solved by the present invention is to provide a 2-cyano-3-disubstituted phenyl acrylate compound for preventing and treating crop diseases with broad spectrum and high efficiency in view of the deficiencies in the prior art.

[0017] The technical problem that the present invention needs to solve is to provide a method for preparing the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds.

[0018] The final technical problem to be solved by the present invention is to provide the application of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds in pesticides.

[0019] In order to solve the above technical problems, the technical solution adopted by the present invention is as follows:

[0020] The present invention discloses a 2-cyano-3-disubstituted phenyl acrylate compound, the structural formula of the 2-cyano-3-disubstituted phenyl acrylate compound is as shown in Formula I:

[0021]

[0022] wherein R1, R2, and R3 are independently selected from H, halogen, CN, NO2, or unsubstituted or substituted amino, hydroxyl, thiol, thiocyanate, C1-C 10 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl group, C3-C6 trialkylsilyl group, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0023] Wherein, R1, R2, and R3 are not H at the same time;

[0024] Wherein, when R1 and R3 are H, R2 is not a hydroxyl group;

[0025] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

[0026] In some embodiments, preferably, R1, R2, and R3 are independently selected from H, halogen, CN, NO2, or unsubstituted or substituted amino, hydroxyl, thiol, thiocyanate, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5 ...alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C3-C6 (alkyl)cycloalkylamino, C3-C6 (alkyl 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl group, C3-C6 trialkylsilyl group, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

[0027] In some embodiments, further preferably, the R1 is F or Cl; the R3 is H;

[0028] The R2 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

[0029] In some embodiments, more preferably, the R1 is F or Cl; the R3 is H;

[0030] The R2 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0031] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclic substitution.

[0032] In some embodiments, when the R1 is F or Cl, and the R3 is H, the structural formula of the 2-cyano-3-disubstituted phenyl acrylate compound is as follows:

[0033]

[0034] Table 1 lists further preferred compounds of the compound represented by formula I-1, but the compounds in Table 1 do not limit the scope of the present invention.

[0035] Table 1 Some preferred compounds of the compound represented by the structure of formula I-1

[0036]

[0037]

[0038]

[0039] In some embodiments, further preferably, said R2 is F or Cl; said R3 is H;

[0040] The R1 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

[0041] In some embodiments, more preferably, said R2 is F or Cl; said R3 is H;

[0042] The R1 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0043] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclic substitution.

[0044] In some embodiments, when the R2 is F or Cl, and the R3 is H, the structural formula of the 2-cyano-3-disubstituted phenyl acrylate compound is as follows:

[0045]

[0046] Table 2 lists further preferred compounds of the compound represented by formula I-2, but the compounds in Table 2 do not limit the scope of the present invention.

[0047] Table 2 Some preferred compounds of the compound represented by the structure of formula I-2

[0048]

[0049]

[0050]

[0051] In some embodiments, further preferably, said R3 is F or Cl; said R2 is H;

[0052] The R1 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

[0053] In some embodiments, further preferably, said R3 is F or Cl; said R2 is H;

[0054] The R1 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0055] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclic substitution.

[0056] In some embodiments, when the R3 is F or Cl and the R2 is H, the structural formula of the 2-cyano-3-disubstituted phenyl acrylate compound is as follows:

[0057]

[0058] Table 3 lists further preferred compounds of the compound represented by formula I-3, but the compounds in Table 3 do not limit the scope of the present invention.

[0059] Table 3 Some preferred compounds of the compound represented by the structure of formula I-3

[0060]

[0061]

[0062]

[0063] In some embodiments, most preferably, the 2-cyano-3-disubstituted phenyl acrylate compound is any one of the following structures:

[0064]

[0065] The following Table 4 is the NMR data of some compounds in Table 1, Table 2 and Table 3. The compound numbers in Table 4 correspond to the compound numbers in Table 1, Table 2 and Table 3, that is, the compound with compound number No. 1 in Table 4 is consistent with the compound with compound number No. 1 in Table 1; in Table 4, 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.

[0066] Table 4 NMR data of some compounds

[0067]

[0068]

[0069] The present invention further discloses pharmaceutically acceptable salts of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds.

[0070] Specifically, the pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenylacrylate compound is hydrochloride.

[0071] The present invention further discloses a method for preparing the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds, which includes the following three methods:

[0072] Method 1 is as follows:

[0073] In some embodiments, when the R1 is F or Cl and the R3 is H, the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-1 undergoes a first alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-1; the intermediate b-1 undergoes a first condensation reaction with ethyl cyanoacetate under the action of a first base to obtain an intermediate c-1; the intermediate c-1 undergoes a first substitution reaction with a substitution compound under the action of a second base and a first catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-1;

[0074]

[0075] Where X=-Br,-I

[0076] The substituted compound is an amine compound, an amide compound or an alcohol compound;

[0077] R2 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0078] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

[0079] In some embodiments, the molar ratio of the benzonitrile compound a-1 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the first alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the first base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-1 to ethyl cyanoacetate and the first base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the first condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The reaction time is 5 to 24 hours; the second base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the first catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the first catalyst is 1:1 to 10, preferably 1:1 to 5, and more preferably 1:2; the molar ratio of the intermediate c-1 to the substituted compound, the second base and the first catalyst is 1:1 to 10:1 to 10:1 to 20, preferably 1:1 to 5:1 to 5:1 to 10, more preferably 1:1 to 2:1 to 2:1 to 5, and even more preferably 1:2:2:3; the first substitution reaction has a reaction temperature of 100 to 180°C and a reaction time of 6 to 24 hours.

[0080] In some embodiments, preferably, the molar ratio of the benzonitrile compound a-1 to the anhydrous ethanol solution of hydrogen chloride is 1:10; the first alcoholysis reaction, the reaction temperature is -5 to 5°C, and the reaction time is 24 to 36 hours; the first base is an organic base; the organic base is triethylamine; the molar ratio of the intermediate b-1 to ethyl cyanoacetate and the first base is 1:1.1:1.2; the first condensation reaction, the reaction temperature is 70 to 100°C, and the reaction time is 6 to 12 hours; the second base is an inorganic base; the inorganic base is cesium carbonate; the first catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the first catalyst is 1:2; the molar ratio of the intermediate c-1 to the substituted compound, the second base, and the first catalyst is 1:2:2:3; the first substitution reaction, the reaction temperature is 100 to 140°C, and the reaction time is 24 hours.

[0081] Among them, the solvent used in the first alcoholysis reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous 1,2-dichloroethane. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0082] Among them, the solvent used in the first condensation reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous ethanol. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0083] Among them, the solvent used in the first substitution reaction is any one of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, or a combination thereof, preferably anhydrous dimethyl sulfoxide. The amount of the solvent used is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0084] Wherein, the first substitution reaction is carried out under the protection of an inert gas, preferably argon gas.

[0085] Method 2 is as follows:

[0086] In some embodiments, when the R2 is F or Cl and the R3 is H, the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-2 undergoes a second alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-2; the intermediate b-2 undergoes a second condensation reaction with ethyl cyanoacetate under the action of a third base to obtain an intermediate c-2; the intermediate c-2 undergoes a second substitution reaction with a substituted compound under the action of a fourth base and a second catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-2;

[0087]

[0088] Where X=-Br,-I

[0089] The substituted compound is an amine compound, an amide compound or an alcohol compound;

[0090] R1 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino;

[0091] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

[0092] In some embodiments, the molar ratio of the benzonitrile compound a-2 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the second alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the third base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-2 to ethyl cyanoacetate and the third base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the second condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The fourth base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the second catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the second catalyst is 1:1-10, preferably 1:1-5, and more preferably 1:2; the molar ratio of the intermediate c-2 to the substituted compound, the fourth base and the second catalyst is 1:1-10:1-10:1-20, preferably 1:1-5:1-5:1-10, more preferably 1:1-2:1-2:1-5, and even more preferably 1:2:2:3; the second substitution reaction has a reaction temperature of 100-180°C and a reaction time of 6-24h.

[0093] In some embodiments, preferably, the molar ratio of the benzonitrile compound a-2 to the anhydrous ethanol solution of hydrogen chloride is 1:10; the second alcoholysis reaction, the reaction temperature is -5 to 5°C, and the reaction time is 24 to 36 hours; the third base is an organic base; the organic base is triethylamine; the molar ratio of the intermediate b-2 to ethyl cyanoacetate and the third base is 1:1.1:1.2; the second condensation reaction, the reaction temperature is 70 to 100°C, and the reaction time is 6 to 12 hours; the fourth base is an inorganic base; the inorganic base is cesium carbonate; the second catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the second catalyst is 1:2; the molar ratio of the intermediate c-2 to the substituted compound, the fourth base, and the second catalyst is 1:2:2:3; the second substitution reaction, the reaction temperature is 100 to 140°C, and the reaction time is 24 hours.

[0094] Among them, the solvent used in the second alcoholysis reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous 1,2-dichloroethane. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0095] Among them, the solvent used in the second condensation reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous ethanol. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0096] Among them, the solvent used in the second substitution reaction is any one of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, or a combination thereof, preferably anhydrous dimethyl sulfoxide. The amount of the solvent used is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0097] Wherein, the second substitution reaction is carried out under the protection of an inert gas, preferably argon.

[0098] Method three is as follows:

[0099] In some embodiments, when the R3 is F or Cl and the R2 is H, the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-3 undergoes a third alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-3; the intermediate b-3 undergoes a third condensation reaction with ethyl cyanoacetate under the action of a fifth base to obtain an intermediate c-3; the intermediate c-3 undergoes a third substitution reaction with a substituted compound under the action of a sixth base and a third catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-3;

[0100]

[0101] Where Y=-Br,-I

[0102] The substituted compound is an amine compound, an amide compound or an alcohol compound;

[0103] R1 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino;

[0104] wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

[0105] In some embodiments, the molar ratio of the benzonitrile compound a-3 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the third alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the fifth base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-3 to ethyl cyanoacetate and the fifth base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the third condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The sixth base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the third catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the third catalyst is 1:1-10, preferably 1:1-5, and more preferably 1:2; the molar ratio of the intermediate c-3 to the substituted compound, the sixth base and the third catalyst is 1:1-10:1-10:1-20, preferably 1:1-5:1-5:1-10, more preferably 1:1-2:1-2:1-5, and even more preferably 1:2:2:3; the third substitution reaction has a reaction temperature of 100-180°C and a reaction time of 6-24h.

[0106] In some embodiments, preferably, the molar ratio of the benzonitrile compound a-3 to the anhydrous ethanol solution of hydrogen chloride is 1:10; the third alcoholysis reaction has a reaction temperature of -5 to 5°C and a reaction time of 24 to 36 hours; the fifth base is an organic base; the organic base is triethylamine; the molar ratio of the intermediate b-3 to ethyl cyanoacetate and the fifth base is 1:1.1:1.2; the third condensation reaction has a reaction temperature of 70 to 100°C and a reaction time of 6 to 12 hours; the sixth base is an inorganic base; the inorganic base is cesium carbonate; the third catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the third catalyst is 1:2; the molar ratio of the intermediate c-3 to the substituted compound, the sixth base and the third catalyst is 1:2:2:3; the third substitution reaction has a reaction temperature of 100 to 140°C and a reaction time of 24 hours.

[0107] Among them, the solvent used in the third alcoholysis reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous 1,2-dichloroethane. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0108] Among them, the solvent used in the third condensation reaction is any one or a combination of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, preferably anhydrous ethanol. The amount of the solvent is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0109] Among them, the solvent used in the third substitution reaction is any one of anhydrous ethanol, anhydrous toluene, anhydrous 1,2-dichloroethane, anhydrous acetonitrile, anhydrous acetone, anhydrous tetrahydrofuran, anhydrous dioxane, anhydrous N,N-dimethylformamide and anhydrous dimethyl sulfoxide, or a combination thereof, preferably anhydrous dimethyl sulfoxide. The amount of the solvent used is such that the materials in the reaction system are dissolved and the viscosity is moderate.

[0110] Wherein, the third substitution reaction is carried out under the protection of an inert gas, preferably argon.

[0111] Furthermore, the present invention discloses a pesticide preparation, which contains 0.1%-45% by weight of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compound or a pharmaceutically acceptable salt of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compound.

[0112] Specifically, the dosage form of the pesticide preparation is a suspension, a dispersible oil suspension, a dispersible liquid, a suspension seed coating, a tablet, a microemulsion, an aqueous solution, an emulsion, an emulsifiable concentrate, an aqueous suspension, a powder, a wettable powder, a soluble powder, a soluble liquid, a granule, a soluble granule, a water-dispersible granule, a capsule, a microcapsule, a microcapsule suspension or a nano preparation.

[0113] Specifically, the pesticide formulation contains agriculturally acceptable carriers and / or adjuvants.

[0114] The use of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds or the above-mentioned pharmaceutically acceptable salts of the 2-cyano-3-disubstituted phenyl acrylate compounds or the above-mentioned pesticide preparations in preventing and controlling fungal diseases of crops is also within the protection scope of the present invention.

[0115] Specifically, the fungal disease is caused by any one or more of the genera Chlorotrichum, Fusarium, Acrocystis, Colletotrichum, Cercospora, Verticillium and Sphaerocystis; the disease is any one or more of rice false smut, wheat fusarium wilt, rice seedling blight, banana wilt, wheat stem base rot, wheat take-all, strawberry anthracnose, apple anthracnose, grape anthracnose, osmanthus anthracnose, citrus anthracnose, rubber tree anthracnose, corn anthracnose, soybean anthracnose, onion anthracnose, pepper anthracnose, wolfberry anthracnose, mango anthracnose, camellia anthracnose, yam anthracnose, peanut brown spot, cotton wilt, and apple tree rot.

[0116] Specifically, the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compounds are applied to the pathogens to be controlled or the medium where they grow, and the dosage is 0.001-1000 g / hectare, preferably 1-1000 g / hectare, more preferably 5-750 g / hectare, further preferably 50-500 g / hectare, and most preferably 75-300 g / hectare.

[0117] Specifically, the pharmaceutically acceptable salt of the above-mentioned 2-cyano-3-disubstituted phenyl acrylate compound is applied to the pathogen to be controlled or the medium where it grows, and the dosage is 0.001 to 1000 g / hectare, preferably 1 to 1000 g / hectare, more preferably 5 to 750 g / hectare, further preferably 50 to 500 g / hectare, and most preferably 75 to 300 g / hectare.

[0118] Specifically, the above-mentioned pesticide preparation is applied to the pathogen to be controlled or the medium where it grows, and the dosage is 0.001-1000 g / hectare, preferably 1-1000 g / hectare, more preferably 5-750 g / hectare, further preferably 50-500 g / hectare, and most preferably 75-300 g / hectare, calculated as the 2-cyano-3-disubstituted phenylacrylate compound or the pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenylacrylate compound in the pesticide preparation.

[0119] Among the 2-cyano-3-disubstituted phenyl acrylate compounds prepared by the present invention, compound No. 1 and compound No. 2 have relatively high activity, and compound No. 1 and compound No. 2 have EC of the mycelial growth of wheat fusarium. 50 The EC values ​​of cyanothiocarb were 0.0153 μg / mL and 0.0077 μg / mL respectively, while the EC values ​​of cyanothiocarb were 0.0153 μg / mL and 0.0077 μg / mL respectively under the same concentration conditions. 50 It is 0.1419 μg / mL. Therefore, compounds No. 1, No. 2 and other compounds prepared by the present invention have the potential to be developed into ultra-high-efficiency pesticides.

[0120] Beneficial effects:

[0121] (1) The present invention provides a novel 2-cyano-3-disubstituted phenyl acrylate compound, which has a broad-spectrum and highly effective fungicidal activity, and has high fungicidal activity against pathogenic bacteria of the genera Chlorotrichum, Fusarium, Acrocystis, Anthracnose, Cercospora, Verticillium, and Sphaerotheca.

[0122] (2) The 2-cyano-3-disubstituted phenyl acrylate compounds provided by the present invention can be used to prepare fungicides in the fields of agriculture, horticulture and industry, and have the advantages of broad spectrum, high efficiency, low toxicity and environmental friendliness. BRIEF DESCRIPTION OF THE DRAWINGS

[0123] The present invention will be further described in detail below in conjunction with the accompanying drawings and specific embodiments, and the above and / or other advantages of the present invention will become more clear.

[0124] Figure 1 The H NMR spectrum of compound No.1 prepared in Example 1;

[0125] Figure 2 The carbon spectroscopy data of the compound No. 1 prepared in Example 1;

[0126] Figure 3 The H NMR spectrum of compound No.87 prepared in Example 2;

[0127] Figure 4The carbon spectroscopy data of compound No. 87 prepared in Example 2;

[0128] Figure 5 The H NMR spectrum of compound No.173 prepared in Example 3;

[0129] Figure 6 The carbon NMR spectrum of compound No. 173 prepared in Example 3;

[0130] Figure 7 The compounds prepared by the present invention have inhibitory effects on diseases caused by Chloroblastoma, Fusarium, Acrocystis and Colletotrichum;

[0131] Figure 8 The inhibitory effect of the compound prepared by the present invention on diseases caused by Anthrax and Cercospora;

[0132] Fig. 9 The compound prepared by the present invention has an inhibitory effect on diseases caused by Verticillium and Melanocorina. DETAILED DESCRIPTION

[0133] The present invention is further described in detail below in conjunction with examples and data, and the present invention is not limited to these specific embodiments. Those skilled in the art should recognize that the present invention encompasses all alternatives, improvements and equivalents that may be included within the scope of the claims. In the present invention, unless otherwise specified, all parts and percentages are weight units, and the equipment and raw materials used, etc. can be purchased from the market or are commonly used in this area. The methods in the following embodiments, unless otherwise specified, are conventional methods in this area.

[0134] (I) Preparation of compounds

[0135] Example 1

[0136] 1. Synthesis of No.1

[0137]

[0138] Compound a-1-1 (10.00mmol, 2.00g) was weighed and placed in a 50mL eggplant-shaped bottle, and anhydrous ethanol hydrogen chloride solution (100.0mmol, 8.50g, 8.00mol / L) and 10mL anhydrous 1,2-dichloroethane were added at 2°C, and the alcoholysis reaction was continued for 30h at 2°C with stirring. After the reaction, the reaction solution was concentrated and vacuum dried to obtain intermediate b-1-1, which was directly used in the next step without purification; intermediate b-1-1 (10.00mmol, 2.40g) was weighed and placed in a three-necked flask, 20mL anhydrous ethanol was added to dissolve, and the system was placed at 0°C, and triethylamine (Et3N, 12.00mmol, 1.20g) was slowly added dropwise to the system, the reaction temperature was controlled not to be higher than 5°C, and stirring was continued for 30min; then the temperature was slowly raised to 80°C for reflux, and ethyl cyanoacetate (11.00mmol, 1. 24g), after the addition was completed, reflux was carried out for condensation reaction, and the reaction degree was observed every 2h until the reaction was complete. The reaction time was 8h. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography to obtain intermediate c-1-1; intermediate c-1-1 (1.00mmol, 0.31g), L-proline (1.00mmol, 0.12g), CuI (2.00mmol, 0.38g), Cs2CO3 (2.00mmol, 0.65g) and methylamine hydrochloride (2.00mmol, 0.16g) were weighed and placed in a 25mL pressure bottle, replaced with argon, and then 5mL of anhydrous DMSO was added, and the substitution reaction was carried out at 120℃ for 24h, and the reaction was monitored by TLC; after the reaction was completed, the reaction solution was concentrated and separated by column chromatography (PE:DCM=1:1) to obtain product I-1-1, recorded as No.1; the nuclear magnetic spectrum of compound No.1 is shown in Figure 1 , NMR data carbon spectrum see Figure 2 .

[0139] 2. The preparation methods of compounds No. 2 to No. 86 (i.e. the compounds recorded in Index Table 1) are the same as the preparation method of "1. Synthesis of No. 1" in Example 1, wherein the preparation methods of compounds No. 2, No. 3, No. 4, No. 6 and No. 7 are as follows:

[0140] Synthesis of compound No.2: The preparation method is the same as the preparation method of "1. Synthesis of No.1" in Example 1, except that methylamine hydrochloride is replaced by ethylamine hydrochloride, and product I-1-2 is prepared, which is recorded as No.2.

[0141] Synthesis of compound No.3: The preparation method is the same as the preparation method of "1. Synthesis of No.1" in Example 1, except that methylamine hydrochloride is replaced by n-propylamine, thereby preparing product I-1-3, which is recorded as No.3.

[0142] Synthesis of compound No.4: The preparation method is the same as the preparation method of "1. Synthesis of No.1" in Example 1, except that methylamine hydrochloride is replaced by isopropylamine, thereby preparing product I-1-4, which is recorded as No.4.

[0143] Synthesis of compound No.6: The preparation method is the same as the preparation method of "1. Synthesis of No.1" in Example 1, except that methylamine hydrochloride is replaced by dimethylamine, so that product I-1-6 is prepared and recorded as No.6.

[0144] Synthesis of compound No.7: The preparation method is the same as the preparation method of "1. Synthesis of No.1" in Example 1, except that methylamine hydrochloride is replaced by cyclopropylamine, thereby preparing product I-1-7, which is recorded as No.7.

[0145] Example 2

[0146] 1. Synthesis of No.87

[0147]

[0148] Weigh compound a-2-87 (10.00mmol, 2.00g) and place it in a 50mL eggplant-shaped bottle, add anhydrous ethanol hydrogen chloride solution (100.0mmol, 8.50g, 8.00mol / L) and 10mL anhydrous 1,2-dichloroethane at 2°C, continue stirring at 2°C for alcoholysis reaction for 30h, and after the reaction, concentrate the reaction solution and vacuum dry to obtain intermediate b-2-87, which is directly used in the next step without purification; weigh intermediate b-2-87 (10.00mmol, 2.40g) and place it in a three-necked flask, add 20mL anhydrous ethanol to dissolve, place it at 0°C, slowly add triethylamine (Et3N, 12.00mmol, 1.20g) to the system, control the reaction temperature not higher than 5°C, and continue stirring for 30min; then slowly heat to 80°C and reflux, slowly add ethyl cyanoacetate (11.00mmol, 1.2 4g), after the addition was completed, the mixture was refluxed for condensation reaction, and the degree of reaction was observed every 2h until the reaction was complete. The reaction time was 8h. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography to obtain intermediate c-2-87; intermediate c-2-87 (1.00mmol, 0.31g), L-proline (1.00mmol, 0.12g), CuI (2.00mmol, 0.38g), Cs2CO3 (2.00mmol, 0.65g) and methylamine hydrochloride (2.00mmol, 0.16g) were weighed and placed in a 25mL pressure bottle, replaced with argon, and then 5mL of anhydrous DMSO was added, and the substitution reaction was carried out at 120℃ for 24h, and the reaction was monitored by TLC; after the reaction was completed, the reaction solution was concentrated and separated by column chromatography (PE:DCM=1:1) to obtain product I-2-87, recorded as No.87; the nuclear magnetic spectrum of compound No.87 is shown in Figure 3 , NMR data carbon spectrum see Figure 4 .

[0149] 2. The preparation methods of compounds No.88 to No.172 (i.e. the compounds recorded in Index Table 2) are the same as the preparation method of "1. Synthesis of No.87" in Example 2, wherein the preparation methods of compounds No.88, No.89 and No.92 are as follows:

[0150] Synthesis of compound No.88: The preparation method is the same as the preparation method of "1. Synthesis of No.87" in Example 2, except that methylamine hydrochloride is replaced by ethylamine hydrochloride, thereby preparing product I-2-88, which is recorded as No.88.

[0151] Synthesis of compound No.89: The preparation method is the same as the preparation method of "1. Synthesis of No.87" in Example 2, except that methylamine hydrochloride is replaced by n-propylamine, thereby preparing product I-2-89, which is recorded as No.89.

[0152] Synthesis of compound No.92: The preparation method is the same as the preparation method of "1. Synthesis of No.87" in Example 2, except that methylamine hydrochloride is replaced by dimethylamine, thereby preparing product I-2-92, which is recorded as No.92.

[0153] Example 3

[0154] 1. Synthesis of No.173

[0155]

[0156] Weigh compound a-3-173 (10.00mmol, 2.00g) and place it in a 50mL eggplant-shaped bottle, add anhydrous ethanol hydrogen chloride solution (100.0mmol, 8.50g, 8.00mol / L) and 10mL anhydrous 1,2-dichloroethane at 2°C, continue stirring at 2°C for alcoholysis reaction for 30h, and after the reaction, concentrate the reaction solution and vacuum dry to obtain intermediate b-3-173, which is directly used in the next step without purification; weigh intermediate b-3-173 (10.00mmol, 2.40g) and place it in a three-necked flask, add 20mL anhydrous ethanol to dissolve, place it at 0°C, slowly add triethylamine (Et3N, 12.00mmol, 1.20g) to the system, control the reaction temperature not higher than 5°C, and continue stirring for 30min; then slowly heat to 80°C and reflux, slowly add ethyl cyanoacetate (11.00mmol, 1.24 g), after the addition was completed, the mixture was refluxed for condensation reaction, and the degree of reaction was observed every 2 hours until the reaction was complete. The reaction time was 8 hours. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography to obtain intermediate c-3-173; intermediate c-3-173 (1.00mmol, 0.31g), L-proline (1.00mmol, 0.12g), CuI (2.00mmol, 0.38g), Cs2CO3 (2.00mmol, 0.65g) and methylamine hydrochloride (2.00mmol, 0.16g) were weighed and placed in a 25mL pressure bottle, replaced with argon, and then 5mL of anhydrous DMSO was added, and the substitution reaction was carried out at 120°C for 24h, and the reaction was monitored by TLC; after the reaction was completed, the reaction solution was concentrated and separated by column chromatography (PE:DCM=1:1) to obtain product I-3-173, recorded as No.173; the nuclear magnetic spectrum of compound No.173 is shown in Figure 5 , NMR data carbon spectrum see Figure 6 .

[0157] 2. The preparation methods of compounds No. 174 to No. 258 (i.e. the compounds recorded in Index Table 3) are the same as the preparation method of "1. Synthesis of No. 173" in Example 3, wherein the preparation methods of compounds No. 174, No. 175, No. 176, No. 179, and No. 180 are as follows:

[0158] Synthesis of compound No.174: The preparation method is the same as the preparation method of "1. Synthesis of No.173" in Example 3, except that methylamine hydrochloride is replaced by ethylamine hydrochloride, thereby preparing product I-3-174, which is recorded as No.174.

[0159] Synthesis of compound No.175: The preparation method is the same as the preparation method of "1. Synthesis of No.173" in Example 3, except that methylamine hydrochloride is replaced by n-propylamine, thereby preparing product I-3-175, which is recorded as No.175.

[0160] Synthesis of compound No.176: The preparation method is the same as the preparation method of "1. Synthesis of No.173" in Example 3, except that methylamine hydrochloride is replaced by isopropylamine, thereby preparing product I-3-176, which is recorded as No.176.

[0161] Synthesis of compound No.179: The preparation method is the same as the preparation method of "1. Synthesis of No.173" in Example 3, except that methylamine hydrochloride is replaced by cyclopropylamine, thereby preparing product I-3-179, which is recorded as No.179.

[0162] Synthesis of compound No.180: The preparation method is the same as the preparation method of "1. Synthesis of No.173" in Example 3, except that methylamine hydrochloride is replaced by isopentylamine, thereby preparing product I-3-180, which is recorded as No.180.

[0163] (II) Preparation of preparations

[0164] The following Examples 4 to 9 provide practical examples of preparing several fungicide formulations using Compound No. 2 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 percentages.

[0165] Example 4: Suspension formulation

[0166] 25% of compound No. 2, 35% of light calcium carbonate, 34% of diatomaceous earth, 1% of lauryl alcohol polyoxyethylene ether (JFC) and 5% of lignin sulfonate are uniformly mixed and crushed to obtain a suspension.

[0167] Example 5: Wettable powder formulation

[0168] 20% of compound No. 2, 38% of light calcium carbonate, 36% of diatomaceous earth, 1% of lauryl alcohol polyoxyethylene ether (JFC) and 5% of lignin sulfonate are uniformly mixed and crushed to obtain a wettable powder.

[0169] Example 6: Emulsifiable Concentrate Formulation

[0170] Heat and stir 15% of compound No. 2, 5% of N-methyl-2-pyrrolidone, 5% of Nongru No. 500 (calcium salt), 5% of Nongru No. 602 and 70% of xylene to obtain an emulsifiable concentrate.

[0171] Example 7: Water dispersible granule formulation

[0172] 30% of compound No.2, 2% of white carbon black, 1% of naphthalenesulfonate, 4% of naphthalenesulfonate formaldehyde condensate and 63% of kaolin are mixed and ground, and then water is added and kneaded, and then added into a granulator equipped with a certain specification of screen for granulation. Then, it is dried and sieved (according to the range of the screen) to obtain a granular product.

[0173] Example 8: Granule Formulation

[0174] 10% of compound No.2, 4% of sodium naphthalenesulfonate formaldehyde condensate (NMO), 1% of polyvinyl alcohol (PVA) and 85% 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.

[0175] Example 9: Aqueous Suspension Formulation

[0176] 30% of compound No. 2, 0.4% of silicone defoamer, 1% of magnesium aluminum silicate, 3% of rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, 1% of fatty alcohol polyoxyethylene ether, 5% of propylene glycol and deionized water (59.5%) 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 and sheared and mixed evenly.

[0177] (III) Determination of biological activity of compounds and field efficacy tests

[0178] Example 10: In vitro biological activity assay of compounds

[0179] The mycelium growth rate method was used to determine the antifungal activity of the target compound. The specific operation is as follows:

[0180] (1) The above-synthesized 2-cyano-3-disubstituted phenyl acrylate compounds (prepared in Examples 1 to 3) were dissolved in dimethyl sulfoxide (DMSO) to prepare a concentration of 10 4 The stock solution was then diluted to 10 μg / mL. 3μg / mL dilution; use a pipette to draw the dilution into the PDA culture medium, shake it quickly and evenly, and prepare a drug treatment group with a final concentration of 1μg / mL; use a PDA plate containing an equal volume of DMSO as a solvent control group; use an equal concentration of cyanoacrylate as a control drug group; "μg / mL" refers to micrograms of active substance per milliliter.

[0181] (2) The test pathogens were inoculated on PDA plates and cultured in a 25°C biochemical incubator until the logarithmic growth phase. A 5 mm diameter bacterial disc was punched out from the edge of the fresh colony using a cork hole puncher and inoculated on a PDA plate containing a certain concentration of the drug to be tested. At the same time, the bacterial blocks were inoculated into PDA culture medium without the drug to be tested and containing cyanothiocarb as a control group. The plates were cultured in the dark in a 25°C biochemical incubator until the control group without the drug to be tested was almost full of the plate. The colony diameter was measured by the cross method (minus the 5 mm bacterial disc diameter); the mycelium growth inhibition rate (MGIR) was calculated using the following formula:

[0182] MGIR% = [(CN) / C] × 100%;

[0183] Where C is the colony diameter of the control group, and N is the colony diameter of the treatment group. In this experiment, three replicates were set for each treatment, and the experiment was repeated three times.

[0184] (3) The pathogens tested were rice false smut (Chlorophytum spp.), wheat fusarium (Fusarium graminearum, Fusarium spp.), rice seedling blight (Fusarium moniliforme, Fusarium spp.), banana wilt (Fusarium oxysporum, Fusarium spp.), wheat stem rot (Pseudofusarium graminearum, Fusarium spp.), wheat take-all (Acrocystis spp.), strawberry anthracnose (Anthracnose spp.), apple anthracnose (Anthracnose spp.), grape anthracnose (Anthracnose spp.), osmanthus anthracnose (Anthracnose spp.), and citrus anthracnose (Anthracnose), rubber tree anthracnose (Anthracnose), corn anthracnose (Anthracnose), soybean anthracnose (Anthracnose), onion anthracnose (Anthracnose), pepper anthracnose (Anthracnose), wolfberry anthracnose (Anthracnose), mango anthracnose (Anthracnose), camellia anthracnose (Anthracnose), yam anthracnose (Anthracnose), peanut brown spot fungus (Cercosporium), cotton wilt fungus (Verticillium), apple tree rot fungus (Black Rot Shell).

[0185] (4) The present invention evaluated the in vitro fungicidal activity of the numbered compounds described in Index Tables 1 to 3 (prepared in Examples 1 to 3). Figure 7 , Figure 8 , Fig. 9 As shown, the experimental results show that: compared with the control agent cyanothiocarb, the compound prepared by the present invention not only has a high inhibitory activity on the hyphae growth of pathogenic bacteria of the genus Fusarium, but also significantly expands the control spectrum.

[0186] (5) In addition, as shown in Table 5, under low concentration conditions, some compounds of the present invention (prepared in Examples 1 to 3) have ultra-high inhibitory activity against the mycelial growth of wheat fusarium, and the inhibition rate is significantly higher than that of the control agent cyanocobalamin.

[0187] Table 5 Inhibitory activity of some compounds on the mycelial growth of wheat fusarium at lower concentrations

[0188]

[0189]

[0190] (6) As shown in Table 6, the effective medium concentration EC of some compounds (prepared in Examples 1 to 3) for inhibiting the growth of mycelium of wheat fusarium 50 , where the EC of compound No.1 is 50 The value is 0.0153 μg / mL, which is the EC value of the control agent cyanothiocarb. 50 The EC value of compound No.2 is 11 times higher than that of 50 The value is 0.0077 μg / mL, which is the EC value of the control agent cyanothiocarb. 50 The value was 54 times that of the control agent cyanothiocarb. This indicated that the inhibitory activity of compounds No. 1 and No. 2 on the mycelial growth of wheat fusarium was significantly higher than that of the control agent cyanothiocarb.

[0191] Table 6 EC of some compounds on mycelial growth of wheat fusarium 50 Determination of value

[0192] Drug Name Virulence regression curve <![CDATA[EC 50 (μg / mL)]]> Correlation coefficient Cyanostrobin y=7.2533+1.0765x 0.1419 0.9889 No.1 y=6.9856+1.0944x 0.0153 0.9998 No.2 y=7.2299+1.0553x 0.0077 0.9990

[0193] Example 11: Preventive effect of compound No. 2 on wheat scab under greenhouse conditions

[0194] Compound No. 2 (prepared in Example 1) was diluted with sterile water containing 0.2 v / v% Tween 20 to 5, 50, 250 and 500 μg / mL of drug solution, cyproconazole was diluted to the same concentration as a positive control, and sterile water containing 0.2 v / v% Tween 20 was used as a negative control. The middle section of wheat leaves with similar growth conditions were selected for marking, and different concentrations of drug solution were applied, and 6 replicates were set for each drug concentration. 3-4 hours after the application of the drug, the wild-type strain PH-1 of wheat fusarium graminearum was inoculated at the application site, and the bacteria were inoculated at the unapplied sites on both sides of the mark to determine the conductivity of the drug, and the inoculation site was wrapped with absorbent cotton to keep it moist. The wheat was placed at 21°C, with a photoperiod of 12h and a relative humidity of 90%. After 3 days, the length of the lesion was measured.

[0195] From the experimental data in Table 7, it can be seen that compound No. 2 has a protective effect on wheat fusarium head blight, and its control effect increases with the increase of the concentration of the agent. At the concentrations of 5μg / mL, 50μg / mL, 250μg / mL and 500μg / mL, the control effect in the upper, middle and lower areas of the leaves is better than that of the control agent cyanothiocarb.

[0196] Table 7 Preventive effect of compound No.2 on wheat scab

[0197]

[0198] Example 12: Field efficacy test of compound No. 2 against wheat scab

[0199] The wheat for the test was Yannong 1212, a variety susceptible to fusarium spores. The test site was located beside Longmiao Road, Gaoliangjian Street, Hongze District, Huai'an City. The test set up 5 treatments: ① 25% cyanothiocarb suspension 375g ai / ha; ② 25% No.2 suspension 75g ai. / ha; ③ 25% No.2 suspension 150g ai / ha; ④ 25% No.2 suspension 225g ai / ha; ⑤ clean water treatment (CK); the above 25% suspensions were all mass concentration ratios; the above 25% No.2 suspensions were prepared by Example 4.

[0200] Each treatment was first sprayed on April 25, 2023, and the second sprayed on May 1. The plot area is 2m×10m=20m 2 , randomized block arrangement, repeated 3 times. The test was conducted in accordance with the "Guidelines for Field Efficacy Tests of Pesticides Part 15: Fungicide Control of Wheat Fusarium Head Blight" (NY / T 1464.15). The disease survey was based on the "Technical Specifications for Wheat Fusarium Head Blight Monitoring and Reporting" (GB / T15796-2011). On May 19, 2023, the number of wheat fusarium head disease and the disease level of each ear were investigated. The disease index and prevention effect were calculated according to NY / T 1464.15. The calculation formula is as follows:

[0201]

[0202]

[0203] Table 8 Field efficacy of 25% No.2 suspension concentrate against wheat scab

[0204] Pharmacy Dosage (g ai / ha) Disease index Effectiveness% Clear water control / 3.49 0 25% Cyanoconazole SC 375 0.87 75.19 25% No.2 suspension 75 1.04 76.28 25% No.2 suspension 150 0.62 82.33 25% No.2 suspension 225 0.56 84.03

[0205] The experimental results are shown in Table 8. Compared with the control agent cyanothiocarb, the control effect of compound No. 2 at a lower dosage of 75 g ai. / ha is equivalent to that of the control agent 25% cyanothiocarb suspension at a dosage of 375 g ai / ha. As the dosage of compound No. 2 per hectare increases, its field control effect also gradually increases.

[0206] In summary, the results of indoor bioassay and field efficacy test of the compounds show that compared with the control agent cyanothiocarb, the compounds prepared by the present invention have significant inhibitory effects on wheat fusarium, biological activity has been significantly improved, and the inhibitory activity has been significantly improved. At the same time, 2-cyano-3-disubstituted phenyl acrylate compounds significantly expand the control spectrum, and have significant control effects on plant diseases caused by Chlorophytum, Fusarium, Acrocystis, Anthracnose, Cercospora, Verticillium, and Black Rot Cordyceps, while the control agent cyanothiocarb is only effective for plant diseases caused by wheat fusarium and rice seedling pathogen in Fusarium, and has no control effect or very poor effect on other diseases.

[0207] The present invention provides a 2-cyano-3-disubstituted phenyl acrylate compound and a preparation method thereof and a method and idea for the application in pesticides. There are many methods and approaches to realize the technical solution. The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the protection scope of the present invention. All components not specified in this embodiment can be realized by existing technologies.

Claims

1. A 2-cyano-3-disubstituted phenyl acrylate compound, characterized in that: The structural formula of the 2-cyano-3-disubstituted phenyl acrylate compound is shown in Formula I: wherein R1, R2, and R3 are independently selected from H, halogen, CN, NO2, or unsubstituted or substituted amino, hydroxyl, thiol, thiocyanate, C1-C 10 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl group, C3-C6 trialkylsilyl group, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; Wherein, R1, R2, and R3 are not H at the same time; Wherein, when R1 and R3 are H, R2 is not a hydroxyl group; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

2. The 2-cyano-3-disubstituted phenyl acrylate compound according to claim 1, characterized in that: The R1, R2, and R3 are independently selected from H, halogen, CN, NO2, or unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl group, C3-C6 trialkylsilyl group, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

3. The 2-cyano-3-disubstituted phenyl acrylate compound according to claim 2, characterized in that: The groups of R1, R2 and R3 include the following three situations: Case ①: R1 is F or Cl; R3 is H; The R2 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; Case ②: R2 is F or Cl; R3 is H; The R1 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; Case ③: R3 is F or Cl; R2 is H; The R1 is selected from unsubstituted or substituted C1-C4 alkylthio, C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino.

4. The 2-cyano-3-disubstituted phenyl acrylate compound according to claim 3, characterized in that: The groups of R1, R2 and R3 include the following three situations: Case ①: R1 is F or Cl; R3 is H; The R2 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclyl substitution; Case ②: R2 is F or Cl; R3 is H; The R1 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclyl substitution; Case ③: R3 is F or Cl; R2 is H; The R1 is selected from unsubstituted or substituted C1-C5 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C 10 Heterocyclic group, C3-C8 dialkylaminocarbonyl, C6-C 10 Aryl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C6 dialkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl or C2-C 10 Heterocyclic substitution.

5. The 2-cyano-3-disubstituted phenyl acrylate compound according to claim 1, characterized in that: The 2-cyano-3-disubstituted phenyl acrylate compound is any one of the following structures:

6. The pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenyl acrylate compound according to claim 1, characterized in that: The pharmaceutically acceptable salt is hydrochloride.

7. The method for preparing the 2-cyano-3-disubstituted phenyl acrylate compound according to claim 1, characterized in that: There are three methods: Method 1 is: the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-1 undergoes a first alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-1; the intermediate b-1 undergoes a first condensation reaction with ethyl cyanoacetate under the action of a first base to obtain an intermediate c-1; the intermediate c-1 undergoes a first substitution reaction with a substitution compound under the action of a second base and a first catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-1; Where X=-Br,-I The substituted compound is an amine compound, an amide compound or an alcohol compound; R2 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclyl substitution; Method 2 is: the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-2 undergoes a second alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-2; the intermediate b-2 undergoes a second condensation reaction with ethyl cyanoacetate under the action of a third base to obtain an intermediate c-2; the intermediate c-2 undergoes a second substitution reaction with a substitution compound under the action of a fourth base and a second catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-2; Where X=-Br,-I The substituted compound is an amine compound, an amide compound or an alcohol compound; R1 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4 dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclyl substitution; Method three is: the preparation method of the 2-cyano-3-disubstituted phenyl acrylate compound comprises the following steps: a benzonitrile compound a-3 undergoes a third alcoholysis reaction with an anhydrous ethanol solution of hydrogen chloride to obtain an intermediate b-3; the intermediate b-3 undergoes a third condensation reaction with ethyl cyanoacetate under the action of a fifth base to obtain an intermediate c-3; the intermediate c-3 undergoes a third substitution reaction with a substitution compound under the action of a sixth base and a third catalyst to obtain a 2-cyano-3-disubstituted phenyl acrylate compound I-3; Where Y=-Br,-I The substituted compound is an amine compound, an amide compound or an alcohol compound; R1 is selected from unsubstituted or substituted amino, hydroxyl, mercapto, thiocyano, C1-C6 alkylthio, C1-C6 alkylamino, C1-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C5-C 10 Bicyclic, C2-C 10 heterocyclic group, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl, benzyl, phenoxy, C1-C6 alkoxy, C1-C4 haloalkoxy, C2-C6 alkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C6-C 10 Arylamino, C1-C4 alkylcarbonylamino, (C1-C4 alkyl)(C1-C4 alkylcarbonyl)amino, C1-C4 alkylsulfonylamino, (C1-C4 alkyl)(C1-C4 alkylsulfonyl)amino, C1-C4 10 Arylsulfonylamino, C3-C 10 Cycloalkylsulfonylamino or C1-C4dialkylaminosulfonylamino; wherein the substitution is selected from hydroxy, halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C1-C4 haloalkyl, C2-C4 haloalkenyl, C2-C4 haloalkynyl, C3-C6 halocycloalkyl, C1-C6 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkoxycarbonyl, C2-C6 alkylcarbonyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C3-C6 (alkyl)cycloalkylamino, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C1-C6 alkoxycarbonylamino, C3-C6 trialkylsilyl, phenyl, halogenated phenyl, benzyl, phenoxy or C2-C 10 Heterocyclic substitution.

8. The preparation method according to claim 7, characterized in that: In method 1: the molar ratio of the benzonitrile compound a-1 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the first alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the first base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-1 to ethyl cyanoacetate and the first base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the first condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The reaction time is 5 to 24 hours; the second base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the first catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the first catalyst is 1:1 to 10, preferably 1:1 to 5, and more preferably 1:2; the molar ratio of the intermediate c-1 to the substituted compound, the second base and the first catalyst is 1:1 to 10:1 to 10:1 to 20, preferably 1:1 to 5:1 to 5:1 to 10, more preferably 1:1 to 2:1 to 2:1 to 5, and even more preferably 1:2:2:3; the first substitution reaction has a reaction temperature of 100 to 180°C and a reaction time of 6 to 24 hours; In method 2: the molar ratio of the benzonitrile compound a-2 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the second alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the third base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-2 to ethyl cyanoacetate and the third base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the second condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The reaction time is 5 to 24 hours; the fourth base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the second catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the second catalyst is 1:1 to 10, preferably 1:1 to 5, and more preferably 1:2; the molar ratio of the intermediate c-2 to the substituted compound, the fourth base and the second catalyst is 1:1 to 10:1 to 10:1 to 20, preferably 1:1 to 5:1 to 5:1 to 10, more preferably 1:1 to 2:1 to 2:1 to 5, and more preferably 1:2:2:3; the second substitution reaction has a reaction temperature of 100 to 180°C and a reaction time of 6 to 24 hours; In method three: the molar ratio of the benzonitrile compound a-3 to the anhydrous ethanol solution of hydrogen chloride is 1:5-20, preferably 1:8-15, and more preferably 1:10; the third alcoholysis reaction, the reaction temperature is -10-25°C, and the reaction time is 24-96h; the fifth base is an organic base or an inorganic base; the organic base is triethylamine, pyridine, 1,8-diazabicyclo-bicyclo (5,4,0)-7-undecene, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is sodium carbonate, potassium carbonate or sodium hydroxide; the molar ratio of the intermediate b-3 to ethyl cyanoacetate and the fifth base is 1:1-5:1-10, preferably 1:1-2:1-5, and more preferably 1:1.1:1.2; the third condensation reaction, the reaction temperature is 70-150°C, and the reaction time is The sixth base is an organic base or an inorganic base; the organic base is triethylamine, lithium diisopropylamide or N,N-diisopropylethylamine; the inorganic base is cesium carbonate, potassium carbonate, potassium phosphate or sodium hydroxide; the third catalyst is L-proline and cuprous iodide; the molar ratio of L-proline to cuprous iodide in the third catalyst is 1:1-10, preferably 1:1-5, and more preferably 1:2; the molar ratio of the intermediate c-3 to the substituted compound, the sixth base and the third catalyst is 1:1-10:1-10:1-20, preferably 1:1-5:1-5:1-10, more preferably 1:1-2:1-2:1-5, and even more preferably 1:2:2:3; the third substitution reaction has a reaction temperature of 100-180°C and a reaction time of 6-24h.

9. A pesticide formulation, characterized in that: The pesticide preparation contains 0.1%-45% by weight of the 2-cyano-3-disubstituted phenyl acrylate compound according to claim 1 or a pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenyl acrylate compound according to claim 6.

10. The pesticide formulation according to claim 9, characterized in that The dosage form of the pesticide preparation is a suspension, a dispersible oil suspension, a dispersible liquid, a suspension seed coating, a tablet, a microemulsion, an aqueous solution, an emulsion, an emulsifiable concentrate, an aqueous suspension, a powder, a wettable powder, a soluble powder, a soluble liquid, a granule, a soluble granule, a water-dispersible granule, a capsule, a microcapsule, a microcapsule suspension or a nano preparation.

11. The pesticide formulation according to claim 9, characterized in that: The pesticide preparation comprises agriculturally acceptable carriers and / or adjuvants.

12. Use of the 2-cyano-3-disubstituted phenylacrylate compound according to claim 1, the pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenylacrylate compound according to claim 6, or the pesticide preparation according to claim 9 in preventing and controlling fungal diseases of crops.

13. The use according to claim 12, characterized in that: The fungal diseases are diseases caused by any one or more of the genera Chlorotrichum, Fusarium, Acrocystis, Colletotrichum, Cercospora, Verticillium and Sphaerocarp; the diseases are any one or more of rice false smut, wheat fusarium wilt, rice seedling blight, banana wilt, wheat stem base rot, wheat take-all, strawberry anthracnose, apple anthracnose, grape anthracnose, osmanthus anthracnose, citrus anthracnose, rubber tree anthracnose, corn anthracnose, soybean anthracnose, onion anthracnose, pepper anthracnose, wolfberry anthracnose, mango anthracnose, camellia anthracnose, yam anthracnose, peanut brown spot, cotton wilt and apple tree rot.

14. The use according to claim 12, characterized in that: The 2-cyano-3-disubstituted phenylacrylate compound according to claim 1 or the pharmaceutically acceptable salt of the 2-cyano-3-disubstituted phenylacrylate compound according to claim 6 or the pesticide preparation according to claim 9 is applied to the pathogen to be controlled or the medium in which it grows, and the dosage is 0.001 to 1000 g / hectare, preferably 1 to 1000 g / hectare, more preferably 5 to 750 g / hectare, further preferably 50 to 500 g / hectare, and most preferably 75 to 300 g / hectare.

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