2-CYANOACRYLATE COMPOUND, AND PREPARATION METHOD THEREFOR AND USE THEREOF

Abstract

The present invention discloses a 2-cyanoacrylate compound and use thereof in controlling a fungal disease of a crop, and belongs to the field of fungicides. The 2-cyanoacrylate compound has a structural formula shown in a formula (I), has excellent fungicidal activity, particularly has a very highly fungicidal activity on Fusarium species, and is suitable for controlling a fungal disease of a crop. Therefore, the compound may be used for preparing a fungicide in the fields of agriculture, horticulture, and the like, and is highly efficient, low in toxicity, and environmentally friendly.

Claims

1. A 2-cyanoacrylate compound, having a structural formula shown in a formula (I), ##STR00021## wherein X is independently selected from NR.sub.1R.sub.2, N?CR.sub.3R.sub.4, and N?NR.sub.5; in the NR.sub.1R.sub.2, R.sub.1 and R.sub.2 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.10 alkyl, halogenated C.sub.1-C.sub.10 alkyl, C.sub.3-C.sub.10 cycloalkyl, halogenated C.sub.3-C.sub.10 cycloalkyl, C.sub.3-C.sub.10 cycloalkyl C.sub.1-C.sub.6 alkyl, cyano C.sub.1-C.sub.10 alkyl, C.sub.1-C.sub.10 alkoxy, halogenated C.sub.1-C.sub.10 alkoxy, hydroxyl C.sub.1-C.sub.10 alkyl, C.sub.1-C.sub.10 alkoxy C.sub.1-C.sub.6 alkyl, halogenated C.sub.1-C.sub.10 alkoxy C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10 alkenyl C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.10 alkynyl, C.sub.2-C.sub.10 alkynyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.10 alkylamino, C.sub.1-C.sub.10 dialkylamino, halogenated C.sub.1-C.sub.10 alkylamino, halogenated C.sub.1-C.sub.10 dialkylamino, amino C.sub.1-C.sub.10 alkyl, C.sub.1-C.sub.10 alkylamino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.10 dialkylamino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.10 alkylcarbonyl, C.sub.1-C.sub.10 alkoxycarbonyl, C.sub.1-C.sub.10 alkylaminocarbonyl, C.sub.1-C.sub.10 dialkylaminocarbonyl, C.sub.1-C.sub.10 alkylsulfonyl, C.sub.1-C.sub.10 alkoxysulfonyl, and C.sub.1-C.sub.10 alkylaminosulfonyl; or the structure of the NR.sub.1R.sub.2 is in a cyclization form: ##STR00022## wherein R.sub.6 and R.sub.7 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.10 alkyl, halogenated C.sub.1-C.sub.10 alkyl, C.sub.3-C.sub.10 cycloalkyl, halogenated C.sub.3-C.sub.10 cycloalkyl, C.sub.1-C.sub.10 alkoxy, halogenated C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.10 alkylamino, C.sub.1-C.sub.10 dialkylamino, halogenated C.sub.1-C.sub.10 alkylamino, and halogenated C.sub.1-C.sub.10 dialkylamino; m is an integer of 1-4; R.sub.3, R.sub.4, and R.sub.5 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.10 alkyl, halogenated C.sub.1-C.sub.10 alkyl, C.sub.3-C.sub.10 cycloalkyl, halogenated C.sub.3-C.sub.10 cycloalkyl, C.sub.1-C.sub.10 alkoxy, halogenated C.sub.1-C.sub.10 alkoxy, C.sub.1-C.sub.10 alkylamino, C.sub.1-C.sub.10 dialkylamino, halogenated C.sub.1-C.sub.10 alkylamino, and halogenated C.sub.1-C.sub.10 dialkylamino; L is an integer of 1-5; and Y is independently selected from hydrogen, C.sub.1-C.sub.10 alkyl, halogenated C.sub.1-C.sub.10 alkyl, and C.sub.3-C.sub.10 cycloalkyl, or one of the following structures shown in Y.sub.1 to Y.sub.3: ##STR00023## n is an integer of 1-10.

2. The 2-cyanoacrylate compound according to claim 1, wherein in the NR.sub.1R.sub.2, the R.sub.1 and the R.sub.2 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.6 alkyl, halogenated C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl, cyano C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, halogenated C.sub.1-C.sub.6 alkoxy, hydroxyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, halogenated C.sub.1-C.sub.6 alkoxy C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkenyl C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkynyl, C.sub.2-C.sub.6 alkynyl C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkylamino, C.sub.1-C.sub.6 dialkylamino, halogenated C.sub.1-C.sub.6 alkylamino, halogenated C.sub.1-C.sub.6 dialkylamino, amino C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6 alkylamino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 dialkylamino C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkylcarbonyl, C.sub.1-C.sub.6 alkoxycarbonyl, C.sub.1-C.sub.6 alkylaminocarbonyl, C.sub.1-C.sub.6 dialkylaminocarbonyl, C.sub.1-C.sub.6 alkylsulfonyl, C.sub.1-C.sub.6 alkoxysulfonyl, and C.sub.1-C.sub.6 alkylaminosulfonyl; or when the structure of the NR.sub.1R.sub.2 is in a cyclization form, the R.sub.6 and the R.sub.7 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.6 alkyl, halogenated C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, halogenated C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylamino, C.sub.1-C.sub.6 dialkylamino, halogenated C.sub.1-C.sub.6 alkylamino, and halogenated C.sub.1-C.sub.6 dialkylamino; the m is an integer of 1-3; the R.sub.3, the R.sub.4, and the R.sub.5 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.6alkyl, halogenated C.sub.1-C.sub.6 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6 alkoxy, halogenated C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6 alkylamino, C.sub.1-C.sub.6 dialkylamino, halogenated C.sub.1-C.sub.6 alkylamino, and halogenated C.sub.1-C.sub.6 dialkylamino; the L is an integer of 1-4; and the Y is independently selected from hydrogen, C.sub.1-C.sub.6 alkyl, halogenated C.sub.1-C.sub.6 alkyl, and C.sub.3-C.sub.6 cycloalkyl, or one of structures shown in Y.sub.1 to Y.sub.3, wherein n is an integer of 1-6.

3. The 2-cyanoacrylate compound according to claim 2, wherein in the NR.sub.1R.sub.2, the R.sub.1 and the R.sub.2 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.3 alkyl, cyano C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, halogenated C.sub.1-C.sub.3 alkoxy, hydroxyl C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkoxy C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkenyl C.sub.1-C.sub.3 alkyl, C.sub.2-C.sub.3 alkynyl, C.sub.2-C.sub.3 alkynyl C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkylamino, C.sub.1-C.sub.3 dialkylamino, halogenated C.sub.1-C.sub.3 alkylamino, halogenated C.sub.1-C.sub.3 dialkylamino, amino C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3 alkylamino C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 dialkylamino C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 alkoxycarbonyl, C.sub.1-C.sub.3 alkylaminocarbonyl, C.sub.1-C.sub.3 dialkylaminocarbonyl, C.sub.1-C.sub.3 alkylsulfonyl, C.sub.1-C.sub.3 alkoxysulfonyl, and C.sub.1-C.sub.3 alkylaminosulfonyl; or when the structure of the NR.sub.1R.sub.2 is in a cyclization form, the R.sub.6 and the R.sub.7 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.3 alkoxy, halogenated C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 alkylamino, C.sub.1-C.sub.3 dialkylamino, halogenated C.sub.1-C.sub.3 alkylamino, and halogenated C.sub.1-C.sub.3 dialkylamino; the m is an integer of 1-2; the R.sub.3, the R.sub.4, and the R.sub.5 are independently selected from hydrogen, hydroxyl, amino, C.sub.1-C.sub.3alkyl, halogenated C.sub.1-C.sub.3 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.3 alkoxy, halogenated C.sub.1-C.sub.3 alkoxy, C.sub.1-C.sub.3 alkylamino, C.sub.1-C.sub.3 dialkylamino, halogenated C.sub.1-C.sub.3 alkylamino, and halogenated C.sub.1-3 dialkylamino; the L is an integer of 1-3; and the Y is independently selected from hydrogen, C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkyl, and C.sub.3-C.sub.6 cycloalkyl, or one of structures shown in Y.sub.1 to Y.sub.3, wherein the n is an integer of 1-3.

4. The 2-cyanoacrylate compound according to claim 3, wherein the X is independently selected from the NR.sub.1R.sub.2; the R.sub.1 and the R.sub.2 are independently selected from hydrogen, C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkyl, C.sub.3-C.sub.6 cycloalkyl, halogenated C.sub.3-C.sub.6 cycloalkyl, C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.3 alkyl, cyano C.sub.1-C.sub.3 alkyl, hydroxyl C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkoxy C.sub.1-C.sub.3 alkyl, amino C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkylamino C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 dialkylamino C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkylcarbonyl, C.sub.1-C.sub.3 alkoxycarbonyl, C.sub.1-C.sub.3 alkylaminocarbonyl, and C.sub.1-C.sub.3 dialkylaminocarbonyl; or the structure of the NR.sub.1R.sub.2 is in a cyclization form: ##STR00024## and the R.sub.6 is independently selected from hydrogen, C.sub.1-C.sub.3 alkyl, halogenated C.sub.1-C.sub.3 alkyl, C.sub.3-C.sub.6 cycloalkyl, and halogenated C.sub.3-C.sub.6 cycloalkyl; the m is an integer of 1-2; the L is an integer of 1-2; and the Y is independently selected from hydrogen, C.sub.1-C.sub.3 alkyl, and halogenated C.sub.1-C.sub.3 alkyl, or one of structures shown in Y.sub.1 to Y.sub.2, wherein the n is an integer of 1-2.

5. The 2-cyanoacrylate compound according to claim 4, wherein the compound is selected from at least one of the compounds shown in the following structural formulas, ##STR00025## ##STR00026## ##STR00027##

6. A preparation method for the 2-cyanoacrylate compound according to claim 1, wherein the X in a structure of the compound is NR.sub.1R.sub.2, the L is 1, and the preparation method comprises the following steps: (1) reacting a compound with a structural formula shown in (A) with an amino protecting group reagent to generate an intermediate B in an organic solvent at a temperature of 0-100? C.; ##STR00028## (2) reacting the intermediate B with a reducing reagent to generate an intermediate C in an organic solvent at a temperature of 0-100? C., wherein the reducing reagent is selected from at least one of iron powder, zinc powder, stannous chloride, hydrogen/palladium carbon, hydrogen/raney nickel, sodium hydrosulfite, and hydrazine hydrate; (3) reacting the intermediate C with R.sub.1X and R.sub.2X to generate an intermediate D through a two-step reaction in an organic solvent and in the presence of an alkali at a temperature of 0-100? C., wherein the alkali is selected from at least one of an organic alkali and an inorganic alkali; and the R.sub.1X and the R.sub.2X are selected from at least one of an alkylation reagent, an acylation reagent, and a sulfonylation reagent; and (4) reacting the intermediate D with a deprotection reagent to generate the 2-cyanoacrylate compound in an organic solvent at a temperature of 0-100? C., wherein the deprotection reagent is at least one of deprotection reagents aiming at an amino protecting group; and the organic solvent in steps (1)-(4) is at least one selected from methanol, ethanol, toluene, dichloromethane, acetonitrile, acetone, tetrahydrofuran, dioxane, N,N-dimethylformamide, and dimethylsulfoxide.

7. A method controlling a fungal disease of a crop comprising the step of applying the 2-cyanoacrylate compound of claim 1.

8. The method according to claim 7, wherein the fungal disease of a crop is a disease caused by at least one of Fusarium, Bremia, Alternaria, Gaeumannomyces, Ustilago, Aspergillus, Ascochyta, Botrytis, and Rhizoctonia.

9. The method according to claim 7, wherein the 2-cyanoacrylate compound is applied at an amount of 10-1,000 g/hectare.

10. A pesticide formulation, comprising 0.001%-99.99% by weight of the 2-cyanoacrylate compound according to claim 1.

Description

DETAILED DESCRIPTION OF THE EMBODIMENTS

[0064] The present invention will be further illustrated in conjunction with specific examples, the present invention is not limited to these specific embodiments. It will be appreciated by those skilled in the art that the present invention covers all alternatives, modifications and equivalents as may be comprised within the scope of the claims.

[0065] In the present invention, unless otherwise specified, all the parts and percentages are in weight, all the used equipment, raw materials, and the like may be commercially available or commonly used in the industry. The methods in the examples are all conventional in the art, unless otherwise specified.

I. Compound Preparation

Example 1: Synthesis of Compound 3

Step 1: Synthesis of Intermediate 3b

[0066] ##STR00015##

[0067] 7.0 g of a raw material 3a and 150 mL of dichloromethane were added to a reaction flask, 11.7 g of di-tert-butyl dicarbonate was added in an ice bath, then 6.0 g of triethylamine and 3.3 g of DMAP were slowly added, and the materials were continuously stirred in an ice bath for 0.5 hour, heated to room temperature, and then stirred for 5 hours. After a reaction, 1 M hydrochloric acid was added to the reaction solution, and an organic phase was separated and then washed once each with pure water and a saturated salt solution. The organic phase was dried over anhydrous Na.sub.2SO.sub.4 and concentrated to obtain 9.6 g of an intermediate 3b, and the crude product was directly used in a next reaction without further purification.

Step 2: Synthesis of Intermediate 3c

[0068] ##STR00016##

[0069] 9.6 g of the intermediate 3b, 120 mL of ethanol, and 24 mL of water were added into a reaction flask, the reaction mixture was heated to 90? C. 3.7 g of iron powder and 12 mL of a saturated ammonium chloride solution were then added, and the reaction was continued for 4 hours. After the reaction was finished, the reaction mixture was filtered through diatomite. The filtrate was concentrated. Water was added and the mixture was extracted with ethyl acetate for three times. The organic phases were combined, and the combined organic phase was concentrated and separated by a column chromatography (an eluent was ethyl acetate and petroleum ether at a volume ratio of 1:2) to obtain 4.5 g of an intermediate 3c with a yield of 51.1%.

Step 3: Synthesis of Intermediate 3d

[0070] ##STR00017##

[0071] 0.19 g of sodium hydride was added to 20 mL of tetrahydrofuran in an ice bath, then 1.0 g of the intermediate 3c was added and the materials were heated to room temperature and stirred for 30 minutes. Then 0.38 g of iodoethane was added, and the materials were stirred at room temperature overnight. After the reaction was finished, water was added to quench the reaction and the mixture was extracted with ethyl acetate for three times. The organic phases were combined, and the combined organic phase was concentrated and separated by a column chromatography (an eluent was ethyl acetate and petroleum ether at a volume ratio of 1:5) to obtain 0.52 g of an intermediate 3d with a yield of 48.1%.

Step 4: Synthesis of Compound 3

[0072] ##STR00018##

[0073] 0.52 g of the intermediate 3d and 20 mL of tetrahydrofuran were added to a reaction bottle, the hydrogen chloride gas which was prepared by adding concentrated sulfuric acid into sodium chloride was slowly bubbled into a reaction solution for 1 hour. Then the reaction mixture was stirred at room temperature overnight. After the reaction, a saturated sodium bicarbonate aqueous solution was added and the mixture was extracted with ethyl acetate twice. The organic phases were combined, and the combined organic phase was concentrated and separated by a column chromatography (an eluent was ethyl acetate and petroleum ether at a volume ratio of 1:2) to obtain 0.35 g of a compound 3 with a yield of 93.3%.

Example 2: Synthesis of Compound 11

Step 1: Synthesis of Intermediate 11d

[0074] ##STR00019##

[0075] 0.19 g of sodium hydride was added to 20 mL of tetrahydrofuran in an ice bath, then 1.0 g of the intermediate 3c was added, and the materials were heated to room temperature and stirred for 30 minutes. Then 2.07 g of iodoethane was added, and the materials were heated 60? C. to react for 24 hours. After the reaction, water was added to quench the reaction and the mixture was extracted with ethyl acetate for three times. The organic phases were combined, and the combined organic phase was concentrated and separated by a column chromatography (an eluent was ethyl acetate and petroleum ether at a volume ratio of 1:2) to obtain 0.66 g of an intermediate 11d with a yield of 56.4%.

Step 2: Synthesis of Compound 1

[0076] ##STR00020##

[0077] 0.66 g of the intermediate 11d and 20 mL of dichloromethane were added to a reaction flask, 1.5 mL of trifluoroacetic acid was added dropwise under an ice bath, and the materials were stirred at room temperature overnight. After the reaction was finished, a saturated sodium bicarbonate aqueous solution was added and the mixture was extracted with ethyl acetate twice. The organic phases were combined, and the combined organic phase was concentrated and separated by a column chromatography (an eluent was ethyl acetate and petroleum ether at a volume ratio of 1:1) to obtain 0.45 g of a compound 11 with a yield of 91.8%.

II. Formulation Preparation

[0078] Practical examples of processing and preparing several fungicide formulations using the compound (I) of the present invention as an active substance are given in examples 3 to 7 below. 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.

Example 3: Wettable Powder Formulation

[0079] 15% of a compound (I) (index tables 1 and 2), 5% of a lignosulfonate (Mq), 1% of polyoxyethylene lauryl ether (JFC), 40% of diatomaceous earth, and 44% of light calcium carbonate were uniformly mixed and crushed to obtain a wettable powder.

Example 4: Missible Oil Formulation

[0080] 10% of a compound (I) (index tables 1 and 2), 5% of Nongru 500 (calcium salt), 5% of Nongru 602, 5% of N-methyl-2-pyrrolidone, and 75% of xylene were heated and stirred uniformly to obtain a missible oil.

Example 5: Granule Formulation

[0081] 5% of a compound (I) (index tables 1 and 2), 1% of polyvinyl alcohol (PVA), 4% of a sodium naphthalenesulfonate formaldehyde condensate (NMO), and 90% of clay were mixed uniformly and crushed, 20 parts of water was added to 100 parts of the mixture, the materials were kneaded and prepared into a 14-32-mesh granule using an extruding granulator, and the granule was dried.

Example 6: Water Dispersible Granule Formulation

[0082] 20% of a compound (I) (index tables 1 and 2), 4% of a naphthalenesulfonate formaldehyde condensate, 1% of a naphthalenesulfonate, 2% of white carbon black, and 73% of kaolin were mixed and crushed, then water was added, the materials were kneaded, and the kneaded materials were fed into a granulator equipped with a sieve having a certain specification for granulation. Then the granule was dried and sieved (according to a range of the sieve) to obtain a granular product.

Example 7: Water Suspension Formulation

[0083] 20% of a compound (I) (index tables 1 and 2), 1% of fatty alcohol-polyoxyethylene ether, 3% of rosin block polyoxyethylene ether polyoxypropylene ether sulfonate, 1% of magnesium aluminum silicate, 0.4% of an organic silicon defoamer, 5% of propylene glycol, and 69.5% of deionized water were mixed uniformly in advance, then the mixture was added into a sand grinder for sand grinding and filtered to obtain a suspension mother solution, a prepared xanthan gum (0.1%) water solution was added, and the materials were sheared and mixed uniformly.

III. Activity Test

[0084] An example of a biological activity assay using the compound of the present invention is given below. It should be noted that the present invention is not limited to the scope of the following example.

Example 8: Antifungal Activity Measurement Test

[0085] An inhibitory activity of the compound to be tested against a test pathogen was measured by using a mycelial growth rate method. The test pathogen was placed on a PDA plate. After growth rate of the pathogen reached a logarithmic phase, a fungal plug with a diameter of 0.5 cm was punched using a puncher on an edge of a fresh fungus colony and inoculated on the PDA plate containing a certain concentration of a drug to be tested. Meanwhile, the fungus plug inoculated on a PDA plate without a drug to be tested was used as a control. The inoculated PDA plates were cultured in a 25? C. incubator for 2-3 days. When the test pathogen grew to the edge of the plate, the plates were examined. A colony growth diameter was measured using a cross method. A mycelial growth inhibition rate (MGIR) was calculated by the following formula: MGIR %=[(C?N)/C]x100%, wherein C is a colony diameter of a control group, and N is a colony diameter of a treated group. The experiment was repeated twice with 2 replicated dishes each time. The test pathogens included wheat scab fungi (Fusarium graminearum and Fusarium asiaticum), melon Fusarium wilt pathogen (Fusarium oxysporum), banana Fusarium wilt pathogen (Fusarium oxysporum), rice bakanae disease pathogen (Fusarium moniliforme), gray mold pathogen, and rice blast pathogen.

[0086] The present invention evaluated an in-vitro fungicidal activity of the numbered compounds in index tables 1-3. The result showed that: the compound of the present invention had highly fungicidal activity and particularly had excellent fungicidal activity against Fusarium fungi. mg/L refers to each mg of active matter per liter. Phenamacril was used as a control agent. The results were specifically as follows:

[0087] The compounds 1, 2, 3, 4, 7, 8, 11, 14, 15, 16, 17, 20, 25, 26, 27, 28, 34, 35, 36, and 37 at a concentration of 0.5 mg/L exhibited greater than 90% of MGIR against the scab pathogen, and the MGIR of phenamacril at the same concentration against the scab pathogen was about 70%. Consistently, under a concentration of 0.25 mg/L, the mycelial growth inhibition rates of compounds 2, 3, 4, 7, 8, 11, 14, 15, 16, and 17 against the scab pathogen were all greater than 90% and obviously higher than that of the control agent phenamacril. Moreover, under a concentration of 0.125 mg/L, the mycelial growth inhibition rates of compounds 2, 3, 7, and 11 against the scab pathogen were all greater than 90%, that are obviously higher than that of phenamacril. The mycelial growth inhibition rate of each compound was shown in the table below.

TABLE-US-00005 TABLE 5 Mycelial growth inhibition rate of compound Compound No. 0.5 mg/L 0.25 mg/L 0.125 mg/L 1 90.2 ? 4.3% 81.2 ? 6.3% 65.5 ? 4.3% 2 99.6 ? 1.3% 95.2 ? 1.8% 90.6 ? 7.6% 3 99.8 ? 3.3% 95.4 ? 7.7% 91.6 ? 2.8% 4 96.5 ? 5.5% 90.5 ? 2.7% 84.3 ? 3.8% 7 99.9 ? 3.0% 96.8 ? 5.7% 94.8 ? 6.1% 8 98.5 ? 2.5% 91.7 ? 3.3% 88.3 ? 4.5% 11 99.9 ? 3.0% 95.3 ? 7.1% 92.2 ? 3.4% 14 96.5 ? 5.6% 90.7 ? 1.3% 85.3 ? 3.3% 15 95.5 ? 2.5% 90.5 ? 3.3% 84.2 ? 4.5% 16 95.2 ? 4.5% 90.2 ? 4.4% 82.3 ? 2.5% 17 94.2 ? 4.5% 90.3 ? 5.7% 81.4 ? 5.5% 20 90.1 ? 1.9% 79.8 ? 1.5% 60.2 ? 2.3% 25 92.3 ? 3.3% 85.1 ? 4.3% 75.3 ? 6.8% 26 92.5 ? 4.0% 84.6 ? 2.3% 77.2 ? 5.5% 27 91.2 ? 4.3% 84.2 ? 2.9% 76.7 ? 7.0% 28 92.8 ? 5.0% 85.3 ? 3.3% 74.4 ? 3.8% 34 92.2 ? 6.3% 84.9 ? 5.4% 74.1 ? 2.3% 35 93.4 ? 4.3% 85.8 ? 1.8% 76.6 ? 3.3% 36 93.5 ? 4.8% 85.4 ? 3.9% 75.2 ? 3.3% 37 92.2 ? 5.4% 84.8 ? 7.1% 73.9 ? 5.5% Phenamacril 69.7 ? 7.7% 36.1 ? 5.0% 21.1 ? 2.3% (control agent)

[0088] In addition, compounds 2, 3, 7, and 11 also showed a good fungicidal activity on a part of a phenamacril-resistant scab pathogen. Under a concentration of 2 mg/L, the mycelial growth inhibition rates of compounds 2, 3, 7, and 11 on type-I myosin S217A, M375A, F419A, and I581A mutant strains were all greater than 60%, and the mycelial growth inhibition rates of the control agent phenamacril against these strains were only 1.2%, 25%, 19%, and 33% respectively.

[0089] Compounds 2, 3, 7, and 11 had a highly fungicidal activity against the melon Fusarium wilt pathogen, the banana Fusarium wilt pathogen, and the rice bakanae disease pathogen. Under a concentration of 1 mg/L, the mycelial growth inhibition rates of compounds 2, 3, 7, and 11 against these pathogens were all greater than 90%, and the mycelial growth inhibition rate of the control agent phenamacril on these pathogens were all 25%.