WO2020034992A1 - Fused heterocycle structure-containing compound, preparation method therefor and applications thereof, and fungicide - Google Patents

Abstract

The present invention relates to the field of agricultural fungicides. Disclosed are a fused heterocycle structure-containing compound, a preparation method therefor and applications thereof, and a fungicide. The fused heterocycle structure-containing compound has the structure as represented by formula (1), formula (2), or formula (3). The compound of the present invention provides excellent control effects with respect to plant diseases caused by various oomycetous pathogens such as Phytophthora infestans, Phytophthora capsica, Pythium ultimum, Phytophthora nicotianae, Phytophthora litchi, and Pseudoperonospora cubensis, is obviously better than conventional oomycosis control agent dimethomorph, and has great market development prospects.

Description

[Corrected 15.08.2019 according to Rule 26] Compounds containing fused heterocyclic structures, preparation methods and applications thereof, and bactericidal 剤 Technical field

The invention relates to the field of pesticide fungicides, in particular to a compound with a fused heterocyclic structure and a preparation method thereof, the application of the compound with a fused heterocyclic structure in preventing and controlling plant oomycetes, and the compound with a fused heterocyclic structure Application as a pesticide fungicide and a fungicide.

Background technique

Oomycetes are one of the important pathogens that cause plant diseases. They have a wide range of parasites, are highly destructive, harmful, and develop rapidly. They can harm most major cash crops such as potatoes, tomatoes, peppers, grapes, tobacco, and peppers. Wait. At the same time, the diseases caused by it are also difficult to prevent and control, thus causing great losses to agricultural production.

The main plant pathogens of oomycetes are Phytophthora infestans, Phytophthora capsici, Pythium ultimum, Phytophthora litchi, and Phytophthora cucumber. Phytophthora infestans is a typical pathogen, and the late potato blight caused by it has caused the famous Irish famine in history. Other plant pathogens can also cause severe disease occurrence. For example, Phytophthora capsici can easily cause diseases of pepper, tomato, eggplant and melons, and cucumber downy mildew caused by downy mildew of cucumbers.

The prevention and control of oomycete diseases is becoming increasingly difficult. At present, chemical control is still the simplest and most effective method in control measures. The main use of production is multi-site protective fungicides and single-site systemic fungicides. However, with the prolonged use of these fungicides and the long-term irrational use, many pathogenic bacteria have developed serious drug resistance. Therefore, the development of new non-cross-resistant oomycete fungicides has become an urgently needed development direction in this field.

Summary of the Invention

The object of the present invention is to provide a new compound with a condensed heterocyclic structure to achieve a good effect of controlling oomycete diseases, especially to achieve a good effect of controlling ooge disease at low concentrations.

To achieve the above object, in a first aspect, the present invention provides a compound having a fused heterocyclic structure or an agrochemically acceptable salt, hydrate, and solvate thereof, the compound having formula (1), formula (2), or The structure shown in formula (3),

In a second aspect, the present invention provides a method for preparing a fused heterocyclic structure-containing compound according to the first aspect, the method comprising: under a nucleophilic substitution reaction condition, combining the compound represented by formula (2-1) with A compound of formula (11), formula (21) or formula (31) undergoes a contact reaction,

In a third aspect, the present invention provides the use of the fused heterocyclic structure-containing compound or the agrochemically acceptable salts, hydrates, and solvates thereof described in the first aspect in controlling plant oomycete diseases.

In a fourth aspect, the present invention provides the use of the fused heterocyclic structure-containing compound or the agrochemically acceptable salts, hydrates, and solvates of the first aspect as pesticide fungicides.

In a fifth aspect, the present invention provides a fungicide, which is composed of an active ingredient and an excipient, and the active ingredient includes the compound having a thick heterocyclic structure according to the first aspect of the present invention or an agrochemically acceptable compound thereof. At least one of a salt, a hydrate, and a solvate.

The compound containing a fused heterocyclic structure or the agrochemically acceptable salts, hydrates and solvates thereof provided by the present invention can effectively control plant oomycete diseases.

The experiment of the present invention shows that the compound of the present invention has excellent control effect on plant diseases caused by various oomycete pathogens such as cucumber downy mildew, Phytophthora capsici, Phytophthora infestans, and the like, and is obviously better than the conventional oocyst disease control agent Acylmorpholine has good market development prospects.

Further, the compound provided by the present invention also has excellent control effects on plant diseases caused by oophyte pathogens such as Phytophthora infestans, Pythium ultimum, Phytophthora nicotianae, Phytophthora litchii and other pathogens.

In addition, due to various downy mildew pathogens such as cucumber downy mildew, Phytophthora capsici, and Phytophthora infestans, resistance to traditional medicines such as dimethomorph, cyanamide, and indoxasulfur has been developed. The compounds are effective in controlling mutant strains that are resistant to existing fungicides. Therefore, the compounds of the present invention are of great significance for the development of novel non-cross-resistant oomycete fungicides.

detailed description

The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and these ranges or values should be understood to include values close to these ranges or values. For numerical ranges, between the end values of each range, between the end values of each range and individual point values, and between the individual point values, one or more new numerical ranges can be obtained by combining each other. These values The scope should be considered to be specifically disclosed herein.

As mentioned above, the first aspect of the present invention provides a compound having a fused heterocyclic structure or an agrochemically acceptable salt, hydrate and solvate thereof, the compound having the formula (1), the formula (2) Or the structure shown by formula (3),

As mentioned above, the second aspect of the present invention provides a method for preparing the fused heterocyclic structure-containing compound according to the first aspect, which method comprises: under the conditions of a nucleophilic substitution reaction, converting formula (2-1) The compound shown is contacted with a compound represented by formula (11), formula (21) or formula (31),

Preferably, the nucleophilic substitution reaction is performed in the presence of a basic reagent and in an anhydrous environment.

Preferably, the alkaline reagent is at least one of sodium hydride, potassium carbonate, and cesium carbonate.

When the nucleophilic substitution reaction of the present invention is performed under basic conditions, the basic conditions may be provided by a solvent such as tetrahydrofuran.

Preferably, the contact reaction is performed in the presence of a solvent, and the solvent is preferably at least one selected from the group consisting of dichloromethane, tetrahydrofuran, N, N-dimethylformamide, acetonitrile, and acetone.

Preferably, the conditions of the contact reaction include: a reaction temperature of 0 to 60 ° C. and a reaction time of 2 to 48 h.

In the present invention, the compound represented by the formula (2-1) may be obtained from a commercial source, or may be synthesized by a method of the prior art according to a structural formula. The present invention exemplarily provides a method for preparing the compound represented by the formula (2-1) in the examples, and those skilled in the art should not be construed as limiting the present invention.

Preferably, in the second aspect of the present invention, the molar ratio of the compound represented by formula (2-1) to the compound represented by formula (11), formula (21) or formula (31) is 1: (1 To 3); more preferably 1: (1.2 to 2.4).

In the second aspect of the present invention, the product obtained after the contact reaction may also be subjected to post-treatment methods conventionally applied in the art to obtain a higher-purity product. For example, the post-treatment operation method includes: extraction , Washing, rotary evaporation, column chromatography, recrystallization and the like, the present invention is not particularly limited in this regard, as long as the aforementioned fused heterocyclic structure-containing compound of the present invention can be obtained.

As mentioned above, the third aspect of the present invention provides the fused heterocyclic structure-containing compound or the agrochemically acceptable salts, hydrates, and solvates thereof according to the first aspect in the control of plant oomycete diseases. application.

Preferably, the plant oomycete diseases include diseases caused by at least one of the pathogens, Phytophthora infestans, Phytophthora capsici, Phytophthora nicotianae, Phytophthora litchii, Phytophthora litchi, Phytophthora infestans and Downy mildew of cucumber .

It should be particularly noted that the structures represented by the foregoing formulae (1), (2), and (3) in the present invention each have an R configuration and an S configuration, and the inventors of the present invention found in research The compounds of formula (1), formula (2) and formula (3) have excellent bactericidal activity in R configuration, S configuration and racemic structure. In order to briefly explain the effects of the compounds of the present invention, in the following text of the present invention, unless otherwise specified, the racemates of the compounds of the present invention are used, and those skilled in the art should not understand the limit.

As mentioned above, the fourth aspect of the present invention provides the use of the fused heterocyclic structure-containing compound or the agrochemically acceptable salts, hydrates, and solvates thereof described in the first aspect as pesticide fungicides.

As mentioned above, the fifth aspect of the present invention provides a fungicide, which is composed of an active ingredient and an excipient, and the active ingredient includes the compound having a condensed heterocyclic structure according to the first aspect, or an agricultural product thereof. At least one of chemically acceptable salts, hydrates, and solvates.

Preferably, the content of the active ingredient is 1-99.9% by weight; more preferably, the content of the active ingredient is 5-95% by weight.

Preferably, the dosage form of the bactericide is at least one selected from the group consisting of emulsifiable concentrate, suspending agent, wettable powder, powder, granule, aqueous preparation, poison bait, mother liquor and mother powder.

In the present invention, the auxiliary materials may be various auxiliary materials conventionally used in the art, and may be, for example, surfactants, solvents, and the like.

Hereinafter, the present invention will be described in detail through examples.

In the following examples, unless otherwise specified, the various raw materials used are all commercially available and the purity is chemically pure.

Example 1

This example is used to illustrate a method for preparing a compound represented by formula (2-1).

(1) At 25 ° C, add 1,3-dichloroacetone (1mol) to 1L of 2M hydrochloric acid ether solution, and then add tert-butyl nitrite (1mol), continue the reaction at 25 ° C for 10h, and remove after the reaction is completed. Diethyl ether, after cooling, a crude product of the compound represented by formula (2-2) is obtained, and washed with 1-chlorobutane, filtered, and the filter cake is collected; and the filtrate is recrystallized, filtered, and the filter cake is dried to obtain formula (2) The compound represented by -2) was combined into two batches to obtain a pure product of the compound represented by formula (2-2).

(2) At 25 ° C, sodium bicarbonate (5 mol) was added to 1 L of a dichloromethane solution of the compound (1 mol) represented by the formula (2-2), and 2,6-difluorostyrene (1 mol) was added. Add slowly and continue to stir the reaction for 4h. After the reaction is complete, filter and remove the solvent from the filtrate to obtain the compound represented by formula (2-3), which can be directly used in the next reaction.

(3) The compound (1 mol), 4-aminothiocarbonyltetrahydropyridine-1 (2H) -tert-butyl formate (1.1 mol) and sodium bromide (0.1 mol) are sequentially represented It was added to 2.5L of acetone, and the reaction system was heated under reflux for 12h. After the reaction was completed, the acetone was removed, 2L of water was added, and the mixture was extracted with 500mL * 3 ethyl acetate. The organic phases were combined, dried and concentrated to obtain the formula (2-4). The crude product of the compound was further purified by column chromatography using an elution system formed of silica gel with petroleum ether and ethyl acetate, to finally obtain a pure compound of the formula (2-4);

(4) Add 100 mL of concentrated hydrochloric acid to a 500 mL methanol solution of the compound (0.5 mol) represented by the formula (2-4), and react at 25 ° C for 6 hours. After the reaction is completed, add 2M aqueous sodium hydroxide solution to adjust the pH to 7 to It was extracted with 500 mL * 5 of ethyl acetate, and the organic phases were combined, dried and concentrated to obtain a compound represented by the formula (2-5).

(5) Triethylamine (0.15 mol) is added to a 500 mL anhydrous dichloromethane solution of the compound (0.1 mol) represented by formula (2-5), the temperature is reduced to 0 ° C, and bromoacetyl bromide (0.12) is slowly added. mol), react at 25 ° C. for 3 h, and after the reaction is completed, add 1M hydrochloric acid solution to adjust pH = 3, extract with 200 mL * 2 dichloromethane, combine the organic phases, dry and concentrate to obtain the compound represented by formula (2-1).

Example 2

This example is for explaining a method for preparing a compound represented by formula (1).

At 0 ° C., sodium hydride (1.5 mmol) was added to a 10 mL DMF solution of the compound (1.2 mmol) represented by formula (11), and the reaction was carried out at 0 ° C. for 0.5 h, followed by the addition of formula (2-1). Compound (1 mmol) was reacted at 25 ° C for 6h. After completion of the reaction, the compound represented by formula (1) was obtained by extraction, washing, and concentration, and purification by column chromatography.

White solid, yield 89%, mp 128-130 ° C, ¹ H NMR (600 MHz, CDCl ₃ ) δ 8.51 (dd, J = 4.8, 1.6 Hz, 1 H), 8.06 (dd, J = 8.4, 1.6 Hz, 1 H ), 7.67 (s, 1H), 7.36–7.28 (m, 1H), 7.10 (dd, J = 8.4, 4.8Hz, 1H), 6.92 (t, J = 8.4Hz, 2H), 6.08 (dd, J = 12.0, 9.0 Hz, 1H), 5.39 (s, 2H), 4.62 (d, J = 13.8 Hz, 1H), 4.07 (d, J = 13.8 Hz, 1H), 3.81 (dd, J = 17.4, 12.0 Hz, 1H), 3.64 (dd, J = 17.4, 9.0 Hz, 1H), 3.37–3.26 (m, 2H), 3.02 (q, J = 7.8 Hz, 2H), 2.85 (t, J = 12.6 Hz, 1H), 2.23 (d, J = 13.8Hz, 1H), 2.16 (d, J = 13.8Hz, 1H), 1.90-1.75 (m, 2H), 1.41 (t, J = 7.8Hz, 3H). 13 C NMR (151MHz , CDCl ₃ ) δ174.36,165.09,162.04 (d, J = 5.1Hz), 160.37 (d, J = 5.1Hz), 152.17,151.48,148.44,146.99,144.98,130.51 (t, J = 6.1Hz), 129.85, 117.82, 116.01, 115.62 (t, J = 16.2 Hz), 114.64, 111.84, 111.69, 72.72, 48.14, 44.50, 41.81, 41.42, 40.21, 32.38, 31.73, 20.96, 13.23. HRMS calculated value C ₂₇ H ₂₆ F ₂ N ₆ O ₂ S [M + Na] ⁺ 537.18788. Found 537.18704.

The single crystal structure (CCDC 1943764) of the compound represented by formula (1) was further confirmed by X-ray crystal diffraction, as shown in FIG. 1.

Example 3

This example is for explaining a method for preparing a compound represented by formula (2).

At 0 ° C, sodium hydride (1.5 mmol) was added to a 10 mL DMF solution of the compound (1.2 mmol) represented by formula (21), the reaction was carried out at 0 ° C for 0.5 h, and then the formula (2-1) was added. Compound (1 mmol) was reacted at 25 ° C for 6h. After completion of the reaction, the compound represented by formula (2) is obtained by extraction, washing, and concentration, and purification by column chromatography.

White solid, yield 79%, mp165-166 ° C, ¹ H NMR (600MHz, DMSO-d ₆ ) δ 8.48 (s, 1H), 8.31 (d, J = 7.8 Hz, 1H), 8.04 (s, 1H ), 7.55--7.45 (m, 1H), 7.27--7.07 (m, 3H), 6.05--5.95 (m, 1H), 5.46 (d, J = 16.8 Hz, 1 H), 5.36 (d, J = 16.8 Hz, 1H), 4.35 (d, J = 13.2 Hz, 1H), 4.13 (d, J = 13.2 Hz, 1H), 3.91 (t, J = 14.4 Hz, 1H), 3.54 (dd, J = 17.4, 8.4 Hz, 1H), 3.36-3.24 (m, 3H), 2.81 (t, J = 12.6Hz, 1H), 2.10 (t, J = 16.2Hz, 2H), 1.78 (d, J = 14.4Hz, 1H), 1.57 ( t, J = 12.6 Hz, 1 H), 1.36 (d, J = 6.6 Hz, 6 H). ¹³ C NMR (101 MHz, DMSO-d ₆ ) δ 175.08, 165.16, 162.00 (d, J = 8.1 Hz), 159.52 (d , J = 8.1 Hz), 152.22, 151.37, 149.24, 148.36, 144.39, 131.45 (t, J = 11.1 Hz), 130.17, 119.93, 116.05, 115.69 (t, J = 16.2 Hz), 113.11, 112.36 (d, J = 6.1Hz), 112.16 (d, J = 6.1Hz), 112.13, 72.13, 48.09, 44.02, 41.27, 32.32, 31.88, 27.63, 22.04, 22.02. HRMS calculated value C ₂₈ H ₂₈ F ₂ N ₆ O ₂ S [ M + Na) ⁺ 573.18547. Found 573.18599.

Example 4

This example is for explaining a method for preparing a compound represented by formula (3).

At 0 ° C, sodium hydride (1.5 mmol) was added to a 10 mL DMF solution of the compound (1.2 mmol) represented by formula (31), and the reaction was carried out at 0 ° C for 0.5 h, followed by the addition of formula (2-1). Compound (1 mmol) was reacted at 25 ° C for 6h. After completion of the reaction, the compound represented by formula (3) was obtained by extraction, washing, and concentration, and purification by column chromatography.

White solid, yield 82%, mp 125-127 ° C, ¹ H NMR (600 MHz, CDCl ₃ ) δ 8.46 (d, J = 4.8 Hz, 1 H), 8.02 (d, J = 8.4 Hz, 1 H), 7.64 ( s, 1H), 7.30–7.20 (m, 1H), 7.05 (t, J = 6.6Hz, 1H), 6.89 (t, J = 8.4Hz, 2H), 6.05 (t, J = 10.8Hz, 1H), 5.30 (s, 2H), 4.57 (d, J = 13.8Hz, 1H), 4.02 (d, J = 13.8Hz, 1H), 3.78 (dd, J = 17.4, 12.0Hz, 1H), 3.61 (dd, J = 17.4, 9.0 Hz, 1H), 3.27 (q, J = 12.6, 12.0 Hz, 2H), 2.81 (t, J = 12.6 Hz, 1H), 2.21–2.08 (m, 3H), 1.85–1.70 (m, 2H), 1.10-0.98 (m, 4H ). 13 C NMR (101MHz, CDCl 3) δ174.34,165.04,162.42 (d, J = 8.1Hz), 159.94 (d, J = 8.1Hz), 152.14,151.50,148.59 , 146.81, 144.94, 130.48 (t, J = 11.1 Hz), 129.56, 117.81, 115.96, 115.58 (t, J = 16.2 Hz), 114.53, 111.81 (d, J = 6.1 Hz), 111.62 (d, J = 6.1 Hz), 111.60, 72.69 (t, J = 3.0 Hz), 48.05, 44.46, 41.75, 41.38, 40.15, 32.31, 31.70, 8.82, 7.37. HRMS calculated value C ₂₈ H ₂₆ F ₂ N ₆ O ₂ S (M + H) ⁺ 549.18788. Found 549.18843.

Test example 1: In vivo activity to inhibit downy mildew of cucumber (potted test)

The test and investigation methods refer to the SOP-SC-1098 cucumber downy mildew potted method in the “Fungicide Volume of Standard Operating Practices for Pesticide Biological Activity Test” prepared by Kang Zhuo and Gu Baogen.

The results are shown in Table 1.

Table 1

It can be known from Table 1 that the compound of the present invention has a good control effect on cucumber downy mildew, and the control effect is 100% at four dosage concentrations of 20 mg / L to 0.625 mg / L. Ethyl ketone is equivalent, especially the compound of formula (1). When the concentration is 0.208 mg / L, the control effect on cucumber downy mildew is still 100%. At the concentrations of 20 mg / L to 0.208 mg / L, the activities of the compounds of formula (1), formula (2) and formula (3) are better than those of the commercial fungicides dimethomorph and indoxacon.

Test Example 2: In Vitro Activity to Inhibit the Growth of Mycelium of Phytophthora capsici

The test method uses the microplate method to determine the biological activity in the pharmacy.

Inoculate the target bacteria in PDB or V8 juice liquid medium for 96 hours, shake them, collect fresh mycelia after filtration, then weigh 0.1g mycelia, put in 50mL of PDB liquid medium, and use a tissue masher The mycelium is mashed into small hypha segments to make a suspension of hypha segments, which are placed at 4 ° C for use.

The test agent was prepared into a 2,000 mg / L mother liquor with dimethyl sulfoxide, and then diluted to a concentration of 0.1 mg / L with sterile water, and stored at 4 ° C for use.

Add the spore suspension (hyphae suspension) and a series of gradient drug solutions prepared in advance to each microwell in an amount of 100 μl + 100 μl, and then place the 96-well microplate in a 25 ° C incubator and let it stand still. After incubation, the OD ₅₉₅ (absorbance at 595 nm) of each treatment was detected with a microplate reader after 3-4 days. Calculate the indoor virulence of the agent against the target bacteria. The test results are shown in Table 2.

Table 2

* 90% ≦ A ≦ 100%; 80% ≦ B <90%; 70% ≦ C <80%; 60% ≦ D <70%; E <60%.

It can be seen from Table 2 that the compound of the present invention has a good inhibitory effect on the mycelial growth of Phytophthora capsici. At a concentration of 0.1 mg / L, the inhibition rate is more than 90%, which is equivalent to that of the control agent fluorothiazolyl pyridone. ; Even at a low dosage of 0.005mg / L, the compound of the present invention inhibits the mycelial growth of Phytophthora capsici by more than 90%, which is better than fluorothiazolyl ethyl ketone, formula (2), formula (3) The compound shown is equivalent to fluorothiazolyl ketone, a control agent. .

Test Example 3: Field Activity Test for Cucumber Downy Mildew

This test refers to the "National Standard for Pesticides of the People's Republic of China" (GB / T 17980.26-2000) "Guidelines for Pesticide Field Application (I) Fungicides to Control Cucumber Downy Mildew". In this test, cucumber downy mildew was used as the target, Zengweiying green and dimethomorph were used as control agents, and the test crop was cucumber, variety Jinchun No. 4.

The group arrangement is arranged in random blocks, each area is about 15m ² , and each process is repeated twice. The stem and leaf spray method is used to spray. Each time, the blank control is first sprayed, and then the same drug is sprayed according to the first low concentration and then high concentration. The sprayer is cleaned 3 times in different drug treatment rooms, and then sprayed to each community. Spray evenly. The test was started when the cucumber plants reached the 10-leaf stage and grew well. Six days after the first application, a second application was carried out for a total of two applications.

Investigation was conducted on the 9th day after the second application. Ten cucumber plants with uniform growth were selected in each plot. The survey method used visual inspection method to visually observe the overall incidence of cucumber plants in the entire plot. The efficacy of the pesticide was estimated based on the size, number, and extent of the disease spots. The visual inspection criteria were as follows:

100%: no disease spots on the leaves, no disease on the plant;

90 to 100%: There are sporadic disease spots on the leaves, and the number of disease spots on the entire plant is 1-4, and the disease spots have not spread significantly.

80 to 90%: there are obvious lesions on the leaves, the number of lesions on the entire plant is 5 to 10, the lesions spread slightly but are not connected;

70 to 80%: the number of disease spots in the entire plant is 11 to 20, and the disease spots are obviously spread, with occasional patches of disease spots;

60 ～ 70%: The number of disease spots in the entire plant is about 20, the disease spots are obviously spread, and the disease spots are obviously continuous.

50-60%: The number of disease spots in the entire plant exceeds 20, and the disease spots spread in a large area;

Below 50%: Compare the incidence of the blank control, and estimate the efficacy of the agent by the number and size of the lesions.

The test results are listed in Table 3.

table 3

The results in Table 3 show that the compound represented by formula (1) has a better control effect on cucumber downy mildew; when the test dose is above 12.5 mg / L, its control effect can reach more than 80%, and the control agent fluorothiazolyl ethyl Compared with ketones, at the same test dose (12.5mg / L, 25mg / L), the control effect is better; the control agent dimethomorph is less effective against cucumber downy mildew. The compound represented by formula (1) is Both test doses were significantly better than dimethomorph.

The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, including the combination of various technical features in any other suitable manner. These simple modifications and combinations should also be regarded as the disclosure of the present invention. All belong to the protection scope of the present invention.

Claims (10)

A compound having a fused heterocyclic structure or an agrochemically acceptable salt, hydrate and solvate thereof, the compound having a structure represented by formula (1), formula (2) or formula (3),

A method for preparing a fused heterocyclic structure-containing compound according to claim 1, comprising: under a nucleophilic substitution reaction condition, combining a compound represented by formula (2-1) with formulas (11) and ( 21) or a compound represented by formula (31)

The method according to claim 2, wherein the nucleophilic substitution reaction is performed in the presence of a basic reagent and in an anhydrous environment; Preferably, the alkaline reagent is at least one of sodium hydride, potassium carbonate, and cesium carbonate. The method according to claim 2 or 3, wherein the conditions of the contact reaction include: a reaction temperature of 0 to 60 ° C and a reaction time of 2 to 48 h. Use of the compound having a fused heterocyclic structure according to claim 1 or an agrochemically acceptable salt, hydrate and solvate thereof in controlling plant oomycete disease. The use according to claim 5, wherein the plant oomycete disease includes Phytophthora infestans, Phytophthora capsici, Pythium ultimum, Phytophthora nicotianae, Phytophthora litchii, Phytophthora infestans and Downy mildew of cucumber Disease caused by at least one germ. Use of the compound having a fused heterocyclic structure according to claim 1 or an agrochemically acceptable salt, hydrate and solvate thereof as a pesticide fungicide. A bactericide comprising an active ingredient and an excipient, the active ingredient comprising the compound having a condensed heterocyclic structure according to claim 1, or an agrochemically acceptable salt, hydrate, and solvate thereof. At least one. The fungicide according to claim 8, wherein the content of the active ingredient is 1 to 99.9% by weight. The germicidal agent according to claim 9, wherein the dosage form of the germicidal agent is at least one selected from the group consisting of emulsifiable concentrate, suspending agent, wettable powder, powder, granule, aqueous solution, poison bait, mother liquor and mother powder.