Hydrazide compounds taking syringic acid as a lead, and preparation method and application thereof

Abstract

The application discloses a kind of hydrazine compounds with eugenol as lead and its preparation method and application, and the biological activity test result shows that all compounds are excellent, broad-spectrum antibacterial activity to the plant pathogenic fungi tested.The inhibition effect of most target compounds on plant pathogenic fungi is better than that of positive control rynaxapyr, and the antibacterial effect of compound 11 on rhizoctonia solani, fusarium graminearum, alternaria solani, phoma exigua var. horii and phoma sorghicola is the best, and the EC 50 Values are 0.258 μg / mL, 0.679 μg / mL, 0.424 μg / mL, 0.384 μg / mL and 0.975 μg / mL respectively; for the gossypium gossypium, the antibacterial effect of compound 12 is the best, and the EC 50 Value is 0.989 μg / mL; followed by compound 11, and the EC 50 Value is 1.248 μg / mL.The hydrazine compounds prepared with eugenol as lead have excellent, broad-spectrum and high-efficiency anti-plant pathogenic microorganism activity, and can be used for preventing and treating plant diseases caused by plant pathogenic microorganisms.

Description

Technical Field

[0001] This invention belongs to the field of pesticide creation, specifically relating to a class of acylhydrazide compounds led by syringic acid, their preparation methods, and applications. Background Technology

[0002] Plant diseases not only reduce crop yields, but toxins also accumulate in food, affecting food security and ultimately endangering human and animal health. Diseases caused by plant pathogenic fungi account for approximately 70-80% of all plant diseases. Pesticides, as substances with special biological activity, control and regulate the growth, development, and reproduction of various agricultural pests, thus playing a role in disease prevention and control. Ensuring the yield and safety of global food and cash crops, they are an indispensable production material in modern agriculture. According to relevant data, ceasing pesticide use would lead to a 30% reduction in crop yields and a 50-70% increase in agricultural product prices, while using pesticides can mitigate unnecessary losses. However, due to the ban on highly toxic pesticides and pesticide resistance, we are forced to continuously develop new, highly efficient, low-toxicity, and low-residue green pesticides.

[0003] Chemically active ingredients extracted from natural products or their derivatives are widely used in various fields such as medicine and pesticides. Chemical synthesis technology enables the expansion of the scale and variety of natural product research, allowing for structural modification and optimization of natural products to improve their efficacy and reduce toxicity, thus facilitating the development of higher-quality drugs led by natural products. Furthermore, highly active small-molecule pesticides synthesized from natural products not only effectively control pests and diseases, but also possess broad application prospects and significant ecological importance in agricultural production due to their diverse active ingredients, environmental friendliness, safety for non-target organisms, and potential health benefits.

[0004] Syringic acid (SA), chemical name: 3,5-dimethoxy-4-hydroxybenzoic acid, is a high-value natural phenolic acid with a variety of biological activities and wide applications. It is commonly found in fruits, vegetables and herbs and has antioxidant, anti-inflammatory, anti-angiogenic, anti-glycation, anti-hyperglycemic, neuroprotective and memory-enhancing activities.

[0005]

[0006] Meanwhile, acylhydrazides (-CO-NH-NH-) possess excellent bactericidal, insecticidal, and anti-inflammatory biological activities, making them a current research hotspot. Commercially available acylhydrazide-containing pesticides include the insecticides chlorpyrifos (RH-5849) and tebufenozide. This invention uses syringic acid as a lead compound and introduces an acylhydrazide structure through chemical synthesis to synthesize a series of novel syringic acid derivatives containing acylhydrazide structures. The biological activity of the target compounds is then tested, aiming to create compounds with even higher activity. Summary of the Invention

[0007] The purpose of this section is to outline some aspects of embodiments of the present invention and to briefly describe some preferred embodiments. Simplifications or omissions may be made in this section, as well as in the abstract and title of this application, to avoid obscuring the purpose of these documents; however, such simplifications or omissions should not be construed as limiting the scope of the invention.

[0008] In view of the problems existing in the above and / or prior art, the present invention is proposed.

[0009] Therefore, the object of the present invention is to overcome the shortcomings of the prior art and provide a class of acylhydrazide compounds led by syringic acid.

[0010] To solve the above-mentioned technical problems, the present invention provides the following technical solution: the general structural formula of the syringohydrazide compound is shown in formula (I):

[0011]

[0012] Wherein, R is selected from one or more of any substituted or unsubstituted alkyl, any substituted or unsubstituted alkenyl, any substituted or unsubstituted alkynyl, any substituted or unsubstituted cycloalkyl, any substituted or unsubstituted aryl, any substituted or unsubstituted benzyl, and any substituted or unsubstituted heteroaryl.

[0013] As a preferred embodiment of the syringic acid derivative containing the acylhydrazine structure described in this invention, wherein: R is selected from one or more of the following: phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl, 2-fluoro-4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,3,5,6-tetrafluorophenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 3,4-dimethylphenyl, and 4-methoxyphenyl.

[0014] The term "alkyl" as used in this invention refers to branched and straight-chain saturated hydrocarbon groups having a specific number of carbon atoms. For example, "C1-C10 alkyl" (or alkylene) refers to C1, C2, C3, C4, C5, C6, C7, C8, C9, and C10 alkyl groups. Additionally, "C1-C6 alkyl" indicates an alkyl group having 1 to 6 carbon atoms. Alkyl groups can be unsubstituted or substituted, such that one or more of their hydrogen atoms are replaced by other chemical groups. Examples of alkyl groups include, but are not limited to, methyl (Me), ethyl (Et), propyl (such as n-propyl and isopropyl), butyl (such as n-butyl, isobutyl, tert-butyl), pentyl (such as n-pentyl, isopentyl, neopentyl), and the like.

[0015] The term "alkenyl" as used in this invention refers to hydrocarbons that have either straight-chain or branched structures and possess one or more carbon-carbon double bonds present at any stable point in the chain. For example, "C2-C6 alkenyl" (or alkenylidene) is intended to include C2, C3, C4, C5, and C6 alkenyl groups. Examples of alkenyl groups include, but are not limited to, vinyl, 1-propenyl, 2-propenyl, 2-butenyl, 3-butenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 2-methyl-2-propenyl, 4-methyl-3-pentenyl, and their analogues.

[0016] The term "alkynyl" as used in this invention refers to hydrocarbons that have either straight-chain or branched structures and possess one or more carbon-carbon triple bonds that occur at any stable point in the chain. For example, "C2-C6 alkynyl" (or ynylene) is intended to include C2, C3, C4, C5, and C6 alkynyl groups; such as ethynyl, propynyl, butynyl, pentylyl, hexynyl, and their analogues.

[0017] In this invention, "substituted" refers to the substitution of any one or more hydrogen atoms on a specified atom or group by a selected specified group, provided that the substitution does not exceed the general valence of the specified atom. Unless otherwise specified, substituents are named to the central structure. For example, it can be understood that when (cycloalkyl)alkyl is a possible substituent, the connection point of the substituent to the central structure is in the alkyl moiety. Cyclic double bonds used herein are double bonds formed between two adjacent ring atoms (e.g., C=C, C=N, or N=N). When substitution is mentioned, especially polysubstitution, it refers to the substitution of multiple substituents at various positions on a specified group, such as difluorophenyl referring to 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, and 3,5-difluorophenyl.

[0018] Combinations of substituents and / or variables are permitted only when these combinations produce stable compounds or useful synthetic intermediates. A stable compound or stable structure implies that the compound is sufficiently stable to be isolated from the reaction mixture with useful purity, subsequently formulated to form an effective therapeutic agent. Preferably, the compound does not currently contain N-halogens, S(O)₂H, or S(O)H groups.

[0019] In this invention, "aryl" refers to a monocyclic or bicyclic aromatic hydrocarbon group having 6 to 12 carbon atoms in the ring moiety, such as phenyl and naphthyl, each of which may be substituted.

[0020] The term "halogen" or "halogen atom" as used in this invention refers to fluorine, chlorine, bromine, and iodine.

[0021] In this invention, "halogenated alkyl" refers to a substituted alkyl group having one or more halogen substituents. For example, "halogenated alkyl" includes monohalogenated, dihalogenated, trihalogenated, tetrahalogenated, trifluoromethyl, and trifluoromethoxy; even if the halogen in the haloalkyl group is specifically defined as fluorine, chlorine, bromine, or iodine, it still refers to a substituted alkyl group having one or more fluorine, chlorine, bromine, or iodine substituents.

[0022] In this invention, "heteroaryl" refers to substituted and unsubstituted aromatic 5- or 6-membered monocyclic groups, 9- or 10-membered bicyclic groups, and 11- to 14-membered tricyclic groups, having at least one heteroatom (O, S, or N) in at least one ring, wherein the heteroatom-containing ring preferably has 1, 2, or 3 heteroatoms selected from O, S, and N. Each ring of the heteroatom-containing heteroaryl may contain one or two oxygen or sulfur atoms and / or 1 to 4 nitrogen atoms, provided that the total number of heteroatoms in each ring is 4 or less, and each ring has at least one carbon atom. The fused ring completing the bicyclic and tricyclic groups may contain only carbon atoms and may be saturated, partially saturated, or unsaturated. Nitrogen and sulfur atoms may optionally be oxidized, and nitrogen atoms may optionally be quaternized. Bicyclic or tricyclic heteroaryl groups must include at least one fully aromatic ring, and the other fused rings may be aromatic or non-aromatic. The heteroaryl group may be attached to any available nitrogen or carbon atom in any ring. Where valence permits, if the other ring is a cycloalkyl or heterocyclic ring, it may optionally be substituted with O (oxygen).

[0023] C1-C10 alkyl refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and their isomers; C1-C10 alkoxy refers to methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy and their isomers; C2-C5 alkenyl refers to vinyl, propenyl, allyl, butenyl, pentenyl and their isomers.

[0024] When referring to substituents as alkenyl, alkynyl, alkyl, halogen, aryl, heteroaryl, alkoxy, cycloalkyl, hydroxyl, amino, mercapto, or phosphinyl, or when these substituents specifically refer to a particular alkenyl, alkynyl, alkyl, halogen, aryl, heteroaryl, alkoxy, cycloalkyl, hydroxyl, amino, mercapto, or phosphinyl group, it refers to one to three of the aforementioned substituents. For example, methylphenyl refers to a phenyl group with one to three methyl-substituted groups.

[0025] As a preferred embodiment of the syringic acid-led hydrazide compound of the present invention, wherein: the compound has a structural formula as shown in Formulas 1-28:

[0026]

[0027] Another objective of this invention is to overcome the shortcomings of the prior art and provide a method for preparing a class of acylhydrazine compounds led by syringic acid.

[0028] To solve the above-mentioned technical problems, the present invention provides the following technical solution, and the synthesis route is as follows:

[0029]

[0030] Another object of the present invention is to provide a class of pharmaceutical compositions for the prevention and control of agricultural pests and diseases.

[0031] As a preferred embodiment of the pharmaceutical composition for controlling agricultural pests and diseases according to the present invention, the pharmaceutical composition comprises an acylhydrazine compound or its stereoisomer, its salt or its solvent compound, and agriculturally acceptable adjuvants, fungicides, insecticides or herbicides.

[0032] As a preferred embodiment of the pharmaceutical composition for preventing and controlling agricultural pests and diseases according to the present invention, the dosage form of the pharmaceutical composition includes one of emulsifiable concentrate, powder, wettable powder, granules, aqueous solution, suspension concentrate, ultra-low volume spray, soluble powder, microcapsule, fumigant, water emulsion or water-dispersible granules.

[0033] Another object of the present invention is to provide an application of a pharmaceutical composition in the prevention and control of agricultural pests and diseases, comprising applying the pharmaceutical composition to the harmful substance or its living environment.

[0034] A preferred embodiment of the pharmaceutical composition for controlling agricultural pests and diseases according to the present invention includes one of the following: *Thanatephorus cucumeris* (Tc), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Colletotrichum fructicola* (Cf), *Colletotrichum gloeosporioides* (Cg), and *Colletotrichum sublineol* (Cs).

[0035] The beneficial effects of this invention compared to existing technologies are as follows: Preliminary bioactivity test results show that almost all compounds exhibit excellent and broad-spectrum antifungal activity against the six plant pathogenic fungi tested. Among them, most target compounds showed better inhibitory effects against plant pathogenic fungi than the positive control cyazofamid, with compounds 11 and 12 showing the most significant effects. Furthermore, compounds exhibiting excellent antifungal activity against plant pathogenic fungi are observed when the hydrazide is attached with different substituted phenyl groups. According to the tested antifungal activity data, compound 11 showed the best antifungal effect against *Thanatephorus cucumeris* (Tc), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Colletotrichum fructicola* (Cf), and *Colletotrichum sublineol* (Cs), with its EC50 value being [missing data]. 50 The values ​​were 0.258 μg / mL, 0.679 μg / mL, 0.424 μg / mL, 0.384 μg / mL, and 0.975 μg / mL, respectively; Compound 12 showed the best antibacterial effect against *Colletotrichum gloeosporioides* (Cg), with an EC50 value of 0.258 μg / mL, 0.679 μg / mL, 0.424 μg / mL, 0.384 μg / mL, and 0.975 μg / mL. 50 The value was 0.989 μg / mL; followed by compound 11, EC 10. 50 The value was 1.248 μg / mL.

[0036] In summary, hydrazide compounds prepared using syringic acid as a lead have excellent, broad-spectrum, and highly efficient antimicrobial activity against plant pathogens and can be used to prevent and control plant diseases caused by plant pathogens.

[0037] The hydrazide compounds led by syringic acid proposed in this invention have a good inhibitory effect on plant pathogenic fungi, providing an important scientific basis for the research and development and creation of new pesticides. Detailed Implementation

[0038] To make the above-mentioned objects, features and advantages of the present invention more apparent and understandable, the specific embodiments of the present invention will be described in detail below with reference to the examples in the specification.

[0039] Many specific details are set forth in the following description in order to provide a full understanding of the invention. However, the invention may also be practiced in other ways different from those described herein, and those skilled in the art can make similar extensions without departing from the spirit of the invention. Therefore, the invention is not limited to the specific embodiments disclosed below.

[0040] Secondly, the term "one embodiment" or "embodiment" as used herein refers to a specific feature, structure, or characteristic that may be included in at least one implementation of the present invention. The phrase "in one embodiment" appearing in different places in this specification does not necessarily refer to the same embodiment, nor is it a single or selective embodiment that is mutually exclusive with other embodiments.

[0041] Unless otherwise specified, all raw materials used in this invention are commercially available.

[0042] Example 1: Preparation of the target compound N'-(2-chlorophenyl)-4-hydroxy-3,5-dimethoxybenzoylhydrazine

[0043] 1 mmol syringic acid, 1.5 mmol 2-chlorophenylhydrazine hydrochloride, 1.5 mmol EDCI, 1.5 mmol HOBt and 3 mmol triethylamine were added to a round-bottom flask, and 5 mL dichloromethane was added as a solvent. The mixture was then placed at room temperature and reacted overnight. The reaction progress was monitored by TLC.

[0044] After the reaction was complete, the solvent was removed by vacuum distillation. 50 mL of ethyl acetate was added, and the mixture was washed once each with 30 mL of 5% hydrochloric acid, 10% sodium bicarbonate solution, and saturated ammonium chloride solution. The organic phase was dried over anhydrous sodium sulfate. The organic phase was concentrated by vacuum distillation and purified by column chromatography (eluent: PE / EA = 10 / 1 to PE / EA = 2 / 1) to obtain the target compound N'-(2-chlorophenyl)-4-hydroxy-3,5-dimethoxybenzoylhydrazine, a brown solid, in a yield of 65.7%.

[0045] Example 2: Preparation of the target compound N'-(2-fluorophenyl)-4-hydroxy-3,5-dimethoxybenzoylhydrazine

[0046] 1 mmol syringic acid, 1.5 mmol 2-fluorophenylhydrazine hydrochloride, 1.5 mmol EDCI, 1.5 mmol HOBt and 3 mmol triethylamine were added to a round-bottom flask, and 5 mL dichloromethane was added as a solvent. The mixture was then placed at room temperature and reacted overnight. The reaction progress was monitored by TLC.

[0047] After the reaction was complete, the target compound was purified by filtration. The specific method is as follows: filtration was performed, followed by washing with dichloromethane, 5% hydrochloric acid, 10% sodium bicarbonate solution, saturated ammonium chloride solution, and purified water in sequence. The resulting solid was then dried to obtain the target compound N'-(2-fluorophenyl)-4-hydroxy-3,5-dimethoxybenzoylhydrazine, a brown solid with a yield of 77.7%.

[0048] The structure, molecular formula, 1H NMR, 1C NMR, and fluorine NMR data, as well as the physicochemical properties of the target products, are shown in Tables 1 and 2.

[0049] Table 1 shows the 1H, 1C, and fluorine NMR spectra of some compounds.

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Table 2 Physicochemical properties of the target compounds

[0058] Compound numbering Color / Status Yield Melting point 1 brown solid 77.7％ 177.9-179.1℃ 2 White solid 74.8％ 193.0-194.7℃ 3 Yellow solid 82.6％ 191.7-193.7℃ 4 brown solid 65.7％ 240.8-241.5℃ 5 White solid 63.5％ 153.9-155.2℃ 6 brown solid 56.7％ 191.5-193.0℃ 7 White solid 87.2％ 248.8-250.2℃ 8 White solid 84.2％ 137.0-138.4℃ 9 brown solid 89.3％ 193.5-194.8℃ 10 brown solid 86.0％ 190.0-191.5℃ 11 White solid 67.8％ 155.8-156.7℃ 12 White solid 78.3％ 208.5-210.3℃ 13 White solid 73.1％ 185.7-187.0℃ 14 White solid 56.8％ 227.5-228.8℃ 15 White solid 54.3％ 215.4-217.1℃ 16 White solid 66.9％ 222.6-223.9℃ 17 White solid 74.9％ 169.3-171.6℃ 18 White solid 78.0％ 191.7-193.3℃ 19 White solid 85.0％ 216.7-2183℃ 20 White solid 76.6％ 176.2-178.0℃ 21 Yellow solid 57.0％ 228.8-229.3℃ 22 White solid 69.7％ 214.6-216.8℃ 23 brown solid 88.3％ 219.1-221.4℃ 24 brown solid 82.2％ 206.1-208.4℃ 25 White solid 82.0％ 178.0-179.5℃ 26 White solid 73.3％ 192.0-193.5℃ 27 brown solid 66.8％ 196.7-198.4℃ 28 White solid 32.4％ 131.0-132.1℃

[0059] Example 3:

[0060] Syringic acid-led hydrazides have shown good bioactivity against plant pathogenic fungi. Examples of their activity against *Thanatephorus cucumeris* (Tc), *Fusarium graminearum* (Gz), *Alternaria solani* (As), *Colletotrichum fructicola* (Cf), *Colletotrichum gloeosporioides* (Cg), and *Colletotrichum sublineol* (Cs) are given below.

[0061] The mycelial growth rate method, also known as the toxic medium method, is one of the routine methods for determining the toxicity of fungicides. The main principle is to mix the test agent with a culture medium and measure the toxicity of the agent by the rate at which colonies grow on the toxic medium. In this example, *Thanatephorus cucumeris* (Tc), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Colletotrichum fructicola* (Cf), *Colletotrichum gloeosporioides* (Cg), and *Colletotrichum sublineol* (Cs) were used as test subjects, with DMSO (dimethyl sulfoxide) as a blank control.

[0062] The specific procedures are as follows: 1) Weigh an appropriate amount of the test compound according to the test concentration, dissolve it in DMSO (the amount should not exceed 1% of the final toxic medium), then add an aqueous solution containing 0.1% Tween 20 to make up to 10 mL, pour it into 90 mL of melted PDA medium, mix well, and then pour it into 9 petri dishes for later use; 2) Sterilize the punch (with an inner diameter of 0.5 cm) by flame, and after it cools, punch holes in the hyphae near the edge of the pre-activated strain, and use an inoculation needle to place the hyphae facet to the center of the toxic medium. After treatment, place them uniformly at 25℃ for incubation; 3) After the colony diameter of the control group grows to 5.5-6.0 cm, use the cross-cross method to determine the colony diameter of the control group and each drug treatment group; 4) Calculate the inhibition rate (%) using the following formula:

[0063] Inhibition rate I% = (CT) / (C-0.5)×100%;

[0064] Where C is the colony diameter of the control group, T is the colony diameter of the drug-treated group, and 0.5 is the diameter of the inoculated mycelium.

[0065] EC 50 Median effective concentration (MEC) is an important indicator for evaluating the sensitivity of plant pathogens to compounds, and it is also a crucial parameter for setting compound concentrations when studying the mechanism of action of compounds. In concentration gradient experiments, five appropriate concentrations were set using the two-fold dilution method. Finally, the inhibition rate of the agent against the plant pathogen and the agent concentration were converted into logarithmic values, and the toxicity curve was obtained through regression analysis using SPSS software to calculate the EC50. 50 .

[0066] The embodiments of the present invention are provided to illustrate the technical solutions of the present invention, but the content of the embodiments is not limited thereto. The experimental results are shown in Tables 3 and 4.

[0067] Table 3. Inhibitory activity of the target compounds against some plant pathogenic fungi (25 μg / mL)

[0068]

[0069]

[0070] Note: "-" indicates that it has not been tested.

[0071] Bioactivity tests showed that all compounds exhibited excellent and broad-spectrum antifungal activity against the six plant pathogenic fungi tested. Most of the target compounds showed better inhibitory effects against plant pathogenic fungi than the positive control, boscalid, with compounds 11 and 12 showing the most significant effects. Furthermore, compounds exhibiting superior antifungal activity against plant pathogenic fungi were observed when the hydrazide was substituted with different phenyl groups.

[0072] Table 4 shows the EC50 values ​​of some target compounds against pathogens such as rice sheath blight.

[0073]

[0074]

[0075]

[0076]

[0077] According to the tested antibacterial activity data, compound 11 showed the best antibacterial effect against *Thanatephorus cucumeris* (Tc), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Colletotrichum fructicola* (Cf), and *Colletotrichum sublineol* (Cs), with its EC... 50 The values ​​were 0.258 μg / mL, 0.679 μg / mL, 0.424 μg / mL, 0.384 μg / mL, and 0.975 μg / mL, respectively; Compound 12 showed the best antibacterial effect against *Colletotrichum gloeosporioides* (Cg), with an EC50 value of 0.258 μg / mL, 0.679 μg / mL, 0.424 μg / mL, 0.384 μg / mL, and 0.975 μg / mL. 50 The value was 0.989 μg / mL; followed by compound 11, EC 10. 50 The value was 1.248 μg / mL.

[0078] In summary, hydrazide compounds prepared using syringic acid as a lead have excellent, broad-spectrum, and highly efficient antimicrobial activity against plant pathogens and can be used to prevent and control plant diseases caused by plant pathogens.

[0079] The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

[0080] The above are merely preferred embodiments of this application, but the scope of protection of this application is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in this application should be included within the scope of protection of this application. Therefore, the scope of protection of this application should be determined by the scope of the claims.

Claims

1. A hydrazide compound led by syringic acid, characterized in that: Hydrazide compounds based on syringic acid are selected from the group consisting of: 。 2. The method for preparing a syringic acid-led hydrazide compound according to claim 1, characterized in that: comprising the steps of: wherein when R is 2-fluorophenyl, it is a method for preparing compound 1; when R is 3-fluorophenyl, it is a method for preparing compound 2; when R is 4-fluorophenyl, it is a method for preparing compound 3; when R is 2-chlorophenyl, it is a method for preparing compound 4; when R is 3-chlorophenyl, it is a method for preparing compound 5; when R is 4-chlorophenyl, it is a method for preparing compound 6; when R is 2-bromophenyl, it is a method for preparing compound 7; when R is 3-bromophenyl, it is a method for preparing compound 8; when R is 4-bromophenyl, it is a method for preparing compound 9; when R is 4-iodophenyl, it is a method for preparing compound 10; when R is 2,4-difluorophenyl, it is a method for preparing compound 11; when R is 3,4-difluorophenyl, it is a method for preparing compound 12; when R is 2-fluoro-4-chlorophenyl, it is a method for preparing compound 13; when R is 2,4-dichlorophenyl, it is a method for preparing compound 14; when R is 3,4-dichlorophenyl, it is a method for preparing compound 15; when R is 2,3,5,6-tetrafluorophenyl, it is a method for preparing compound 16; when R is 2-trifluoromethylphenyl, it is a method for preparing compound 17; when R is 3-trifluoromethylphenyl, it is a method for preparing compound 18; when R is 4-trifluoromethylphenyl, it is a method for preparing compound 19; when R is 4-trifluoromethoxyphenyl, it is a method for preparing compound 20; when R is 2-nitrophenyl, it is a method for preparing compound 21; when R is phenyl, it is a method for preparing compound 22; when R is 2-methylphenyl, it is a method for preparing compound 23; when R is 3-methylphenyl, it is a method for preparing compound 24; when R is 4-methylphenyl, it is a method for preparing compound 25; when R is 3,4-dimethylphenyl, it is a method for preparing compound 26; when R is 4-methoxyphenyl, it is a method for preparing compound 27; when R is tert-butyl, it is a method for preparing compound 28. The composition comprises the compound as claimed in any one of claims 1-2 and an agriculturally acceptable adjuvant, bactericide, insecticide, herbicide and antiviral agent.

3. A composition characterized in that: The dosage form of the composition comprises one of emulsifiable concentrate, powder, wettable powder, granule, aqueous agent, suspension, ultra-low volume spray, soluble powder, microcapsule, smoke agent, emulsion in water or water dispersible granule.

4. The composition of claim 3, wherein: The agricultural pests and diseases comprise diseases caused by pathogenic microorganisms of Rhizoctonia solani, Gibberella zeae, Alternaria solani, Colletotrichum gloeosporioides, Glomerella cingulata or Cercospora kikuchii.

5. The use of a compound according to any one of claims 1 to 2 or a composition according to claim 3 for controlling pests in agriculture. ​

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