Hydrazide compound taking syringic acid as pilot as well as preparation method and application of hydrazide compound

Abstract

The invention discloses a hydrazide compound taking syringic acid as a lead as well as a preparation method and application of the hydrazide compound, and a biological activity test result shows that all the compounds have excellent and broad-spectrum antibacterial activity on tested plant pathogenic fungi. Wherein the inhibition effect of most target compounds on plant pathogenic fungi is superior to that of positive control boscalid, the compound 11 has the best antibacterial effect on rhizoctonia solani, fusarium graminearum, alternaria solani, colletotrichum frutescens and colletotrichum sorghum, and EC50 values of the compound 11 are respectively 0.258 [mu] g / mL, 0.679 [mu] g / mL, 0.424 [mu] g / mL, 0.384 [mu] g / mL and 0.975 [mu] g / mL; for colletotrichum gloeosporioides, the compound 12 has the best antibacterial effect, and the EC50 value of the compound 12 is 0.989 mu g / mL; and secondly, a compound 11 with an EC50 value of 1.248 [mu] g / mL. The hydrazide compound prepared by taking syringic acid as a lead has excellent, broad-spectrum and efficient plant pathogenic microorganism resisting activity, and can be used for preventing and treating plant diseases caused by plant pathogenic microorganisms.

Description

Technical Field

[0001] The invention belongs to the field of pesticide creation, and specifically relates to a class of hydrazide compounds with syringic acid as the leader, and a preparation method and application thereof. Background Art

[0002] Plant diseases not only lead to a decrease in crop yields, but also toxins accumulate in food, affecting food security, and further endangering the health of humans and animals. Diseases caused by plant pathogenic fungi account for about 70-80% of plant diseases. Pesticides, as substances with special biological activity, can control and regulate the growth, development and reproduction of various agricultural pests, thereby playing a role in preventing and controlling diseases to ensure the yield and safety of global food and cash crops. They are indispensable means of production for modern agriculture. According to relevant data, stopping the use of pesticides will lead to a 30% decrease in crop yields and a 50-70% increase in agricultural product prices, while the use of pesticides can recover unnecessary losses. However, due to the prohibition of highly toxic pesticides and drug resistance, we are forced to continue to develop new green pesticides with high efficiency, low toxicity and low residue.

[0003] Active chemical ingredients extracted from natural products or derivatives of natural products 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, and can structurally modify and optimize natural products, thereby improving their efficacy and reducing toxicity, etc., which helps to develop better quality natural product-led drugs. In addition, highly active pesticide small molecules synthesized from natural products can not only effectively control pests and diseases, but also have broad application prospects and important ecological significance in agricultural production due to their diverse active ingredients, environmental friendliness, safety to non-target organisms, and potential health-care activities.

[0004] Syringic acid (SA), chemical name: 3,5-dimethoxy-4-hydroxybenzoic acid, is a high-value natural phenolic acid with multiple biological activities and a wide range of uses. 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] At the same time, hydrazide (-CO-NH-NH-) compounds have good biological activities such as bactericidal, insecticidal and anti-inflammatory, and are one of the current research hotspots. Commercialized pesticides containing hydrazide include insecticides such as hydrazide (RH-5849) and fenbuconazole. The present invention takes syringic acid as a guide, introduces the hydrazide structure by chemical synthesis, synthesizes a series of novel syringic acid derivatives containing hydrazide structure, and tests the biological activity of the target compound to create a more active compound. Summary of the invention

[0007] The purpose of this section is to summarize some aspects of embodiments of the present invention and briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section and the specification abstract and the invention title of this application to avoid blurring the purpose of this section, the specification abstract and the invention title, and such simplifications or omissions cannot be used to limit the scope of the present invention.

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

[0009] Therefore, the purpose of the present invention is to overcome the deficiencies in the prior art and provide a class of hydrazide compounds with syringic acid as the lead.

[0010] In order to solve the above technical problems, the present invention provides the following technical solution: the general structural formula of the syringoyl hydrazide compound is as shown in formula (I):

[0011]

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

[0013] As a preferred embodiment of the syringic acid derivative containing a hydrazide structure of the present invention, wherein: the R is selected from one or more of 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] "Alkyl" mentioned in the present invention refers to a branched and straight chain saturated hydrocarbon group 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. In addition, for example, "C1-C6 alkyl" refers to an alkyl group having 1 to 6 carbon atoms. The alkyl group may be non-substituted or substituted so that one or more of its 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 "alkenyl" mentioned in the present invention is a hydrocarbon that includes both a straight chain or a branched structure and has one or more carbon-carbon double bonds that appear at any stable point in the chain. For example, "C2-C6 alkenyl" (or alkenylene) is intended to include C2, C3, C4, C5 and C6 alkenyl. Examples of alkenyl 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 the like.

[0016] The "alkynyl" mentioned in the present invention is a hydrocarbon including a straight chain or branched structure, and has one or more carbon-carbon triple bonds appearing at any stable point in the chain. For example, "C2-C6 alkynyl" (or alkynylene) is intended to include C2, C3, C4, C5 and C6 alkynyl; such as ethynyl, propynyl, butynyl, pentynyl, hexynyl and the like.

[0017] The term "substituted" as used herein refers to any one or more hydrogen atoms on a designated atom or group being substituted with a selected designated group, provided that the general valence of the designated atom is not exceeded. If not otherwise specified, the substituent is named to the central structure. For example, it is understood that when (cycloalkyl) alkyl is a possible substituent, the point of attachment of the substituent to the central structure is in the alkyl portion. The ring double bond used herein is a double bond formed between two adjacent ring atoms (such as C=C, C=N or N=N). When referring to substitution, especially polysubstitution, it refers to multiple substituents replacing at various positions on the designated group, such as difluorophenyl refers 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 permissible only if such combinations result in stable compounds or useful synthetic intermediates. A stable compound or stable structure implies that the compound is sufficiently stable when isolated in a useful purity from a reaction mixture to be formulated into an effective therapeutic agent. Preferably, the present compounds do not contain N-halogen, S(O)2H or S(O)H groups.

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

[0020] The "halogen" or "halogen atom" mentioned in the present invention refers to fluorine, chlorine, bromine and iodine.

[0021] The "haloalkyl" mentioned in the present invention refers to a substituted alkyl group having one or more halogen substituents. For example, "haloalkyl" includes monohalo, dihalo, trihalo, tetrahalo, trifluoromethyl and trifluoromethoxy; even if the halo in the haloalkyl group is clearly defined as fluorine, chlorine, bromine, or iodine, it also refers to a substituted alkyl group having one or more fluorine, chlorine, bromine, or iodine substituents.

[0022] The "heteroaryl" mentioned in the present invention 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, and 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 from 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 rings completing the bicyclic and tricyclic groups may contain only carbon atoms and may be saturated, partially saturated or unsaturated. The nitrogen and sulfur atoms may be optionally oxidized and the nitrogen atoms may be optionally quaternized. The bicyclic or tricyclic heteroaryl must include at least one fully aromatic ring, and the nitrogen and other fused rings may be aromatic or non-aromatic. The heteroaryl group may be connected on any available nitrogen or carbon atom of any ring. If the other ring is a cycloalkyl or heterocyclic ring, it is additionally optionally substituted with O (oxygen) when valence permits.

[0023] C1-C10 alkyl refers to methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and isomers thereof; C1-C10 alkoxy refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyl, heptyl, octyloxy, nonyloxy, decyloxy and isomers thereof; C2-C5 alkenyl refers to ethenyl, propenyl, allyl, butenyl, pentenyl and isomers thereof.

[0024] When a substituent is referred to as alkenyl, alkynyl, alkyl, halogen, aryl, heteroaryl, alkoxy, cycloalkyl, hydroxyl, amino, mercapto, phosphino, or when these substituents are specifically alkenyl, alkynyl, alkyl, halogen, aryl, heteroaryl, alkoxy, cycloalkyl, hydroxyl, amino, mercapto, phosphino, it refers to one to three of the above substituents. For example, methylphenyl refers to phenyl substituted with one to three methyl groups.

[0025] As a preferred embodiment of the hydrazide compound with syringic acid as the lead in the present invention, the structural formula of the compound is one of Formulas 1-28:

[0026]

[0027] Another object of the present invention is to overcome the deficiencies in the prior art and provide a method for preparing hydrazide compounds using syringic acid as a precursor.

[0028] In order to solve the above technical problems, the present invention provides the following technical solutions, and the synthesis route is as follows:

[0029]

[0030] Another object of the present invention is to provide a pharmaceutical composition for preventing and controlling agricultural pests and diseases.

[0031] As a preferred embodiment of the pharmaceutical composition for controlling agricultural pests and diseases described in the present invention, the pharmaceutical composition comprises a hydrazide compound or its stereoisomer, or a salt or a solvent compound thereof, and an agriculturally acceptable adjuvant, fungicide, insecticide or herbicide.

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

[0033] Another object of the present invention is to provide an application of a pharmaceutical composition in preventing and controlling agricultural pests and diseases, including applying the pharmaceutical composition to harmful substances or their living environment.

[0034] As a preferred embodiment of the pharmaceutical composition for controlling agricultural pests and diseases described in the present invention, it includes: one of rice sheath blight fungus (Thanatephorus cucumeris, Tc), wheat fusarium rust fungus (Gibberella zeae, Gz), solanum chain spore fungus (Alternaria solani, As), fruit thorn spore fungus (Colletotrichum fructicola, Cf), gloeosporioides (Colletotrichum gloeosporioides, Cg) and sorghum thorn spore fungus (Colletotrichum sublineol, Cs).

[0035] Compared with the prior art, the present invention has the following beneficial effects: Preliminary biological activity test results show that almost all compounds exhibit excellent and broad-spectrum antibacterial activity against the six plant pathogenic fungi tested. Among them, the inhibitory effects of most target compounds on plant pathogenic fungi are better than those of the positive control boscalid, with 11 and 12 being the most significant. In addition, when the hydrazide is connected to differently substituted phenyl groups, the compounds have excellent anti-plant pathogenic fungi activity. According to the tested antibacterial activity data, compound 11 has the best antibacterial effect against rice sheath blight (Thanatephorus cucumeris, Tc), wheat fusarium (Gibberella zeae, Gz), Alternaria solani (As), fruit spiny spore (Colletotrichum fructicola, Cf), and sorghum spiny spore (Colletotrichum sublineol, Cs), and its EC 50 The values ​​were 0.258μg / mL, 0.679μg / mL, 0.424μg / mL, 0.384μg / mL and 0.975μg / mL, respectively; for Colletotrichum gloeosporioides (Cg), compound 12 had the best antibacterial effect, and its EC 50 The value was 0.989 μg / mL; followed by compound 11, EC 50 The value is 1.248μg / mL.

[0036] In general, hydrazide compounds prepared with syringic acid as the precursor have excellent, broad-spectrum and high-efficiency anti-plant pathogenic microorganism activity and can be used to prevent and control plant diseases caused by plant pathogenic microorganisms.

[0037] The acylhydrazide compounds with syringic acid as the lead proposed in the present invention have a good inhibitory effect on plant pathogenic fungi, and provide an important scientific basis for the research and development and creation of new pesticides. DETAILED DESCRIPTION

[0038] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are described in detail below in conjunction with the embodiments of the specification.

[0039] In the following description, many specific details are set forth to facilitate a full understanding of the present invention, but the present invention may also be implemented in other ways different from those described herein, and those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present 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 term "in one embodiment" that appears in different places in this specification does not necessarily refer to the same embodiment, nor does it refer to a separate or selective embodiment that is mutually exclusive with other embodiments.

[0041] The raw materials used in the present invention are all commercially available unless otherwise specified.

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

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

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

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

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

[0047] After the reaction is completed, the target compound is filtered and purified. The specific method is as follows: filter, wash with dichloromethane, 5% hydrochloric acid, 10% sodium bicarbonate solution, saturated ammonium chloride solution and purified water in sequence, and then dry the obtained solid to obtain the target compound N'-(2-fluorophenyl)-4-hydroxy-3,5-dimethoxybenzoic acid hydrazide as a brown solid with a yield of 77.7%.

[0048] The structure, molecular formula, H NMR spectrum, C NMR spectrum and F NMR spectrum data, and physical and chemical properties of the target products are shown in Tables 1 and 2.

[0049] Table 1 H NMR, C NMR and F NMR data of some compounds

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Table 2 Physicochemical properties of target compounds

[0058] Compound No. Color / State 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] Embodiment 3:

[0060] Hydrazide compounds led by syringic acid showed good biological activity against plant pathogenic fungi. The following takes the activity against rice sheath blight (Thanatephorus cucumeris, Tc), wheat fusarium rust (Gibberellazeae, Gz), solanum chain spore fungus (Alternaria solani, As), fruit thorn spore fungus (Colletotrichum fructicola, Cf), gloeosporioides (Colletotrichum gloeosporioides, Cg) and sorghum thorn spore fungus (Colletotrichum sublineol, Cs) as examples.

[0061] The mycelium growth rate method is also called the toxic medium method, which is one of the conventional methods for determining the toxicity of fungicides. The main principle is to mix the test agent with the culture medium, and measure the toxicity of the agent by the growth rate of the colony on the toxic culture medium. In this embodiment, rice sheath blight (Thanatephorus cucumeris, Tc), wheat fusarium (Gibberella zeae, Gz), solanum chain spore (Alternaria solani, As), fruit thorn spore (Colletotrichum fructicola, Cf), gloeosporioides (Colletotrichum gloeosporioides, Cg) and sorghum thorn spore (Colletotrichum sublineol, Cs) are used as test objects, and DMSO (dimethyl sulfoxide) is used as a blank control.

[0062] The specific operation is as follows: 1) according to the test concentration, weigh an appropriate amount of the compound to be tested, dissolve it with DMSO (the amount should not exceed 1% of the final poisonous medium), then add an aqueous solution containing 0.1% Tween 20 to make the volume 10mL, pour it into 90mL of melted PDA medium, mix well and pour it into 9 culture dishes for use; 2) Sterilize the puncher (with an inner diameter of 0.5cm), and after cooling, punch the hyphae at the edge of the pre-activated strain, and use an inoculation needle to stick its hyphae surface to the center of the poisonous medium. After the treatment is completed, place it uniformly at 25°C for culture; 3) After the colony diameter of the control group grows to 5.5-6.0cm, the colony diameter of the control group and each drug treatment group is determined by the cross method; 4) The inhibition rate (%) is calculated using the following formula:

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

[0064] Among them, 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 bacterial cake.

[0065] EC 50 Median effective concentration (MEC) is an important indicator for evaluating the sensitivity of plant pathogens to compounds. It is also an important parameter for setting compound concentration when studying the mechanism of action of compounds. In the concentration gradient experiment, the two-fold dilution method was used to set 5 appropriate concentrations. Finally, the inhibition rate of the agent on plant pathogens and the concentration of the agent were converted into logarithmic values. The toxicity curve was obtained through regression analysis using SPSS software, and the EC was calculated. 50 .

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

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

[0068]

[0069]

[0070] Note: “-” means not tested

[0071] The results of biological activity tests showed that all compounds showed excellent and broad-spectrum antifungal activity against the six plant pathogenic fungi tested. Among them, most of the target compounds had better inhibitory effects on plant pathogenic fungi than the positive control boscalid, with 11 and 12 being the most significant. In addition, when the hydrazide was connected to different substituted phenyl groups, the compounds had excellent anti-plant pathogenic fungi activity.

[0072] Table 4 EC50 values ​​of some target compounds against rice sheath blight and other pathogens

[0073]

[0074]

[0075]

[0076]

[0077] The antibacterial activity data showed that compound 11 had the best antibacterial effect against rice sheath blight (Thanatephoruscucumeris, Tc), wheat fusarium (Gibberella zeae, Gz), solanum chain spore (Alternariasolani, As), fruit thorn spore (Colletotrichum fructicola, Cf), sorghum thorn spore (Colletotrichum sublineol, Cs), and its EC 50 The values ​​were 0.258μg / mL, 0.679μg / mL, 0.424μg / mL, 0.384μg / mL and 0.975μg / mL, respectively; for Colletotrichum gloeosporioides (Cg), compound 12 had the best antibacterial effect, and its EC 50 The value was 0.989 μg / mL; followed by compound 11, EC 50 The value is 1.248μg / mL.

[0078] In general, hydrazide compounds prepared with syringic acid as the precursor have excellent, broad-spectrum and high-efficiency anti-plant pathogenic microorganism activity and can be used to prevent and control plant diseases caused by plant pathogenic microorganisms.

[0079] The embodiments described above are only descriptions of the preferred modes of the present invention, and are not intended to limit the scope of the present invention. Without departing from the design spirit of the present invention, various modifications and improvements made to the technical solutions of the present invention by ordinary technicians in this field should all fall within the protection scope determined by the claims of the present invention.

[0080] The above are only preferred specific implementations of the present application, but the protection scope of the present application is not limited thereto. Any changes or substitutions that can be easily thought of by a person skilled in the art within the technical scope disclosed in the present application should be included in the protection scope of the present application. Therefore, the protection scope of the present application should be based on the protection scope of the claims.

Claims

1. A class of hydrazide compounds with syringic acid as the lead, characterized in that: The compound has a structure shown in the following general formula (I): In the formula, R is selected from one or more of optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkenyl, optionally substituted or unsubstituted alkynyl, optionally substituted or unsubstituted cycloalkyl, optionally substituted or unsubstituted aryl, optionally substituted or unsubstituted benyl, and optionally substituted or unsubstituted heteroaryl.

2. The hydrazide compound with syringic acid as the lead according to claim 1, characterized in that: The R is selected from one or more of 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.

3. The hydrazide compound with syringic acid as the lead according to claim 1, characterized in that: The hydrazide compound or its stereoisomer or its salt or its solvate with syringic acid as the leading compound is selected from the following compounds:

4. A method for preparing a hydrazide compound or a stereoisomer thereof or a salt thereof or a solvate thereof with syringic acid as the lead according to any one of claims 1 to 3, characterized in that: The steps include:

5. A composition, characterized in that: The composition comprises the compound according to any one of claims 1 to 4 or its stereoisomer or its salt or solvate and an agriculturally usable adjuvant, fungicide, insecticide, herbicide and antiviral agent.

6. The composition according to claim 5, characterized in that: The dosage form of the composition includes one of emulsifiable concentrate, powder, wettable powder, granule, aqueous solution, suspension, ultra-low volume spray, soluble powder, microcapsule, smoke agent, aqueous emulsion or water-dispersible granule.

7. Use of the compound according to any one of claims 1 to 4, or its stereoisomer, or its salt, or its solvate, or the composition according to claim 5 in preventing and controlling agricultural pests and diseases.

8. Use of the compound or its stereoisomer, or its salt or solvate or composition as claimed in claim 7, characterized in that: The agricultural pests and diseases are plant bacterial or fungal diseases.

9. Use of the compound or its stereoisomer, or its salt or solvate or composition as claimed in claim 8, characterized in that: The agricultural pests and diseases include diseases caused by pathogenic microorganisms such as rice sheath blight, wheat fusarium, solanum serrata, fruit spiny colletotrichum, gloeosporium and sorghum spiny colletotrichum.

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