Alpha, beta-unsaturated amides or hydrazides containing a carbonyl structure, and preparation method and application thereof

Abstract

The present application relates to the technical field of pharmaceutical chemistry, and particularly relates to an alpha, beta-unsaturated amide or hydrazide compound containing a carbonyl structure, a preparation method and application. The present application mainly prepares the alpha, beta-unsaturated amide or hydrazide compound containing a carbonyl structure. The compound has a novel structure, and has a good inhibitory effect on plant pathogenic fungi, and particularly has a good inhibitory effect on plant pathogenic fungi such as grape colletotrichum, rice sheath blight, brassica sclerotinia, wheat scab, tomato early blight, tobacco brown spot and eggplant fusarium wilt. The compound has outstanding advantages in the prevention and treatment of plant fungal diseases.

Description

Technical Field

[0001] This invention relates to the field of medicinal chemistry, specifically to a compound containing a carbonyl α,β-unsaturated amide or acyl hydrazine structure, its preparation method, and its application. Background Technology

[0002] Plant fungal diseases can cause crop yield reduction and quality degradation, resulting in serious economic losses. Furthermore, some fungi secrete toxic factors that are harmful to humans and animals. Common plant fungal diseases include rapeseed sclerotinia stem rot, wheat scab, tomato early blight, blueberry root rot, grape canker, rice sheath blight, tobacco red spot, and eggplant verticillium wilt, which can cause symptoms such as wilting, rotting, and necrosis in crops, severely impacting the yield and quality of crops and cash crops. However, the long-term use or overuse of traditional fungicides has led to problems such as drug resistance and environmental pollution. Therefore, there is an urgent need to develop novel fungicides with high activity, high selectivity, novel mechanisms of action, and environmental friendliness.

[0003] Currently, structural modification of natural products is one of the important strategies for discovering novel green fungicides. Tryptophan, a natural product containing an indole ring structure, exists in the mammalian brain and some plants, playing a role in neuroregulation. Tryptophan and its derivatives have a variety of biological activities, including antibacterial, anti-migraine, anti-acetylcholinesterase, vasodilator, and antiarrhythmic effects. For example, in 2021, Sheng et al. designed and synthesized a series of tryptophan derivatives and measured their antifungal activity, finding that most compounds exhibited good antibacterial activity [J]. European Journal of Medicinal Chemistry, 2021, 222: 113563; in 2023, Sheng et al. prepared a new series of tryptophan derivatives and evaluated their antifungal activity, with most compounds showing significant antibacterial activity [J]. Journal of Medicinal Chemistry, 2023, 66: 9040-9056. Furthermore, α,β-unsaturated amides or acylhydrazides, due to their α,β-unsaturated carbonyl fragments, can react with active electrophilic groups present in DNA, RNA, or certain important enzymes via Michael addition reactions, forming Michael adducts that cause DNA molecule breakage or inactivation. On the other hand, many natural products and highly active compounds possess excellent biological activity and clinical application potential precisely because they contain this special structure. Therefore, to find natural lead compounds with highly efficient antibacterial activity, this invention mainly uses tryptamine, 3-(aminomethyl)indole, aniline, and phenethylamine as bases to synthesize a series of α,β-unsaturated amides or acylhydrazides containing carbonyl structures, which exhibit good biological activity against plant pathogenic microorganisms. Summary of the Invention

[0004] One of the objectives of this invention is to provide a class of α,β-unsaturated amides or hydrazides containing a carbonyl group, or their stereoisomers, salts, or solvates.

[0005] Another object of the present invention is to provide intermediate compounds for preparing the above-mentioned compounds or their stereoisomers, their salts or their solvates, and methods thereof.

[0006] Another object of the present invention is to provide a composition containing the above-mentioned compound or its stereoisomer, its salt or its solvate.

[0007] Another object of the present invention is to provide the use of the above-mentioned compound or its stereoisomer, its salt or its solvate, or the composition thereof.

[0008] Another object of the present invention is to provide a method for preventing and controlling agricultural diseases using the above-mentioned compound or its stereoisomer, its salt or its solvate, or the composition thereof.

[0009] To achieve the above objectives, the present invention adopts the following technical solution:

[0010] A compound containing a carbonyl group, an α,β-unsaturated amide or an acylhydrazine, or a stereoisomer thereof, a salt thereof, or a solvate thereof, having a structure as shown in general formula (I):

[0011]

[0012] in,

[0013] R1 is selected from tryptophan, 3-(aminomethyl)indole, aniline, and phenylethylamine.

[0014] R2 is selected from one or more of hydrogen, deuterium, alkyl (either substituted or unsubstituted), alkenyl (either substituted or unsubstituted), alkynyl (either substituted or unsubstituted), aryl (either substituted or unsubstituted), benzyl (either substituted or unsubstituted), aniline (either substituted or unsubstituted), and heteroaryl (either substituted or unsubstituted).

[0015] Preferably, R2 is selected from one or more of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted benzyl, substituted or unsubstituted aniline, and substituted or unsubstituted heteroaryl; preferably, R is selected from one or more of hydrogen, deuterium, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, substituted or unsubstituted C6-C15 aryl, substituted C6-C15 benzyl, substituted C6-C15 aniline, and substituted or unsubstituted C6-C10 heteroaryl, wherein the substitution refers to being substituted by a C1-C6 alkyl, C2-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy, substituted or unsubstituted C6-C15 aryl, substituted C6-C15 benzyl, substituted C6-C15 aniline, and substituted or unsubstituted C6-C10 heteroaryl, wherein the substitution refers to being substituted by a C1-C6 alkyl, C2-C6 alkyl, C2-C6 alkyl, C2-C15 ... One or more of 1-C6 alkoxy, amino, hydroxyl, halogen, nitro, and trifluoromethyl are substituted; more preferably, R is selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1,1-dimethyl, 1,5-dimethylhexyl, 1,1-diethanolyl, propenyl, allyl, methoxy, ethoxy, propoxy, butoxy, substituted or unsubstituted phenyl, substituted or unsubstituted aniline, and substituted benzyl, wherein the substitution refers to being substituted by one or more of C1-C6 alkyl, C1-C6 alkoxy, amino, hydroxyl, halogen, nitro, and trifluoromethyl; most preferably, R2 is selected from:

[0016]

[0017] Most preferably, the compound or its stereoisomer, its salt or its solvate, etc., are selected from the following specific compounds:

[0018]

[0019] The present invention also provides a method for preparing various compounds containing carbonyl structures, α,β-unsaturated amides or acylhydrazides, or their stereoisomers, salts, or solvates, characterized by comprising the following steps:

[0020]

[0021] R1 and R2 are as described above.

[0022] The present invention also provides a composition comprising the said compound or its stereoisomer, its salt or its solvate, and agriculturally usable adjuvants or fungicides, insecticides or herbicides; preferably, the formulation of the composition is selected from emulsifiable concentrates (EC), powders (DP), wettable powders (WP), granules (GR), aqueous solutions (AS), suspensions (SC), ultra-low volume sprays (ULV), soluble powders (SP), microcapsules (MC), fumigants (FU), emulsions (EW), and water-dispersible granules (WG).

[0023] The compound or its stereoisomer, its salt or its solvate, or the composition thereof can be used to prevent and control agricultural diseases. Preferably, the agricultural disease is a plant fungal disease; more preferably, the agricultural disease is rapeseed sclerotinia stem rot, wheat scab, tomato early blight, grape canker, rice sheath blight, tobacco red spot disease, or eggplant verticillium wilt.

[0024] This invention also provides a method for preventing and controlling agricultural diseases, wherein the compound or its stereoisomer, its salt or its solvate, or the composition thereof acts on a harmful substance or its living environment; preferably, the agricultural disease is a plant fungal disease; more preferably, the agricultural disease is a disease caused by sclerotinia rot of rapeseed, scab of wheat, early blight of tomato, grape canker, rice sheath blight, tobacco red spot disease, verticillium wilt of eggplant, *Colletotrichum cankeri*, *Colletotrichum gloeosporioides ...

[0025] The present invention also provides a method for protecting plants from agricultural diseases, comprising the method steps of contacting the plant with the compound or its stereoisomer, its salt or its solvate, or the composition thereof.

[0026] The term "alkyl" as used here refers to both branched and straight-chain saturated hydrocarbon groups having a specific number of carbon atoms. For example, "C 1-10 Alkyl (or alkylene) refers to C1, C2, C3, C4, C5, C6, C7, C8, C9, and C10 alkyl groups. Additionally, for example, "C 1-6 "Alkyl" means 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.

[0027] "Alkenyl" refers to hydrocarbons that include both straight-chain and branched structures and have one or more carbon-carbon double bonds that appear at any stable point in the chain. For example, "C 2-6 The term "alkenyl" (or "alkenylidene") aims 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.

[0028] "Alkyne" refers to hydrocarbons that can be either straight-chain or branched and have one or more carbon-carbon triple bonds that appear at any stable point in the chain. For example, "C 2-6 The purpose of "alkynyl" (or ynylene) is to include C2, C3, C4, C5 and C6 alkynyl groups; such as ethynyl, propynyl, butynyl, pentylyl, hexynyl and their analogues.

[0029] The term "substituted" as used herein refers to the substitution of any one or more hydrogen atoms on a specified atom or group by a chosen 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 point of connection of the substituent to the central structure is within the alkyl moiety. Cyclic double bonds as 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 dichlorophenyl referring to 1,2-dichlorophenyl, 1,3-dichlorophenyl, 1,4-dichlorophenyl, and 2,4-dichlorophenyl.

[0030] Combinations of substituents or variables are permitted only when these combinations yield 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.

[0031] The term "aryl" refers to a monocyclic or bicyclic aromatic hydrocarbon group, such as phenyl and naphthyl, having 6 to 12 carbon atoms in the ring moiety, each of which can be substituted.

[0032] The term "halogen" or "halogen atom" refers to chlorine, bromine, fluorine, and iodine.

[0033] The term "haloalkyl" refers to a substituted alkyl group having one or more halogen substituents. For example, "haloalkyl" includes mono, bis, and trifluoromethyl groups; even if the halogen in a haloalkyl group is explicitly 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.

[0034] The term "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 a 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 rings 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. Heteroaryl groups 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).

[0035] Exemplary monocyclic heteroaryl groups include pyrrole, pyrazolyl, pyrazolinyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, furanyl, thiophenyl, oxadiazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, and their analogues.

[0036] Exemplary bicyclic heteroaryl groups include indole, spirochetone, benzodioxazolyl, benzoxazolyl, benzothiophene, quinolinyl, tetrahydroisoquinolinyl, isoquinolinyl, benzimidazolyl, benzofuranyl, indoleazinyl, benzofuranyl, chromone, coumarinyl, benzofuranyl, cinolinyl, quinoxalinyl, indazole, pyrrolopyridyl, fluoropyridyl, dihydroisoindole, tetrahydroquinolinyl, and their analogues.

[0037] Unless otherwise stated, the compounds of this invention are understood to include both their free state and their salts. The term "salt" means an acidic and / or basic salt formed from inorganic and / or organic acids and bases.

[0038] Preferably, 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.

[0039] 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.

[0040] By adopting the above technical solutions, this invention synthesizes a series of α,β-unsaturated amides or hydrazides containing carbonyl structures, based on tryptamine, 3-(aminomethyl)indole, aniline, and phenethylamine compounds. It has been found that this series of compounds exhibits good inhibitory effects against plant pathogenic fungi, showing good inhibitory effects against pathogenic fungi [such as *Botryosphaeria dothidea* (Bd), *Rhizoctonia solani* (Rs), *Sclerotinia clerotiorum* (Ss), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Alternaria alternata* (Aa), and *Verticillium dahliae* (Vd)], providing an important scientific basis for the research and development of new pesticides. Detailed Implementation

[0041] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0042] Unless otherwise specified, the technical means used in the embodiments are conventional means well known to those skilled in the art. All raw materials and solvents used in the embodiments are commercially available products.

[0043] Example 1: Preparation of Intermediate 1

[0044] Maleic anhydride (1 g, 10.2 mmol) was added to 15 mL of dichloromethane and stirred at room temperature for 10 min. Then, tryptophan (1.63 g, 10.2 mmol) was slowly added and stirred overnight. The mixture was filtered to obtain a pale yellow solid, with a yield of 90%.

[0045] Other intermediates were synthesized from maleic anhydride using 3-(aminomethyl)indole, aniline, and phenethylamine as raw materials, respectively, following the steps in Example 1.

[0046] Example 2: Target compound N 1 -(2-(1H-indol-3-yl)ethyl)-N 4 Intermediate 1 (0.5 g, 1.94 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.44534 g, 2.32 mmol), and 1-hydroxybenzotriazole (0.15695 g, 1.16 mmol) were added to a 50 mL round-bottom flask. 10 mL of dichloromethane was added as a solvent, along with triethylamine (0.23508 g, 2.32 mmol). The mixture was stirred at room temperature for 30 min, and then 4-methoxyaniline (0.47683 g, 3.87 mmol) was added until intermediate 1 was completely reacted. The reaction mixture was extracted with water (20 mL) and separated, then extracted with dichloromethane (30 mL × 2). The organic layer was dried over anhydrous Na₂SO₄ and evaporated under vacuum. The target compound was separated and purified by column chromatography using CH₂Cl₂ and CH₃OH (200:1; V / V) as eluents. The target compound 1, a yellow liquid, was finally obtained with a yield of 70.1%.

[0047] Other target compounds were synthesized using appropriate starting materials or substituents, following the steps in Example 2.

[0048] The structures and 1H and 1C NMR spectra of the synthesized carbonyl-containing α,β-unsaturated amides or hydrazides are shown in Table 1, and their physicochemical properties are shown in Table 2.

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

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] Table 2 Physicochemical properties of the target compounds

[0062]

[0063]

[0064] Pharmacological Example 1:

[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 the compound concentration when studying the mechanism of action of target 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 in vitro tests for resistance to pathogenic fungi were conducted using the mycelial growth rate inhibition method to assess the antibacterial activity of the synthesized target compounds against plant pathogenic fungi such as *Botryosphaeria dothidea* (Bd), *Rhizoctonia solani* (Rs), *Sclerotinia sclerotiorum* (Ss), *Gibberella zeae* (Gz), *Alternaria solani* (As), *Alternaria alternata* (Aa), and *Verticillium dahliae* (Vd) on PDA medium. Weigh the target compound to be tested using a 0.01 g / mL balance. Dissolve it in 20 times the volume of DMSO until completely dissolved. The concentration of the stock solution after complete dissolution is 50 μg / mL. Take the corresponding volume of the stock solution at the corresponding concentration and transfer it to a 2 mL centrifuge tube. Add DMSO to balance to a final volume of 1 mL. Transfer the solution to a 15 mL sterile centrifuge tube in an aseptic workbench. Add 9 mL of Tween-20 water and shake thoroughly to mix. Pour the mixture into the culture medium and mix well. Dispense the mixture evenly into 9 petri dishes and let it cool for later use. In an aseptic workbench, use a sterile punch (5 mm) to make mycelial discs (5 mm in diameter) from normally growing colonies. Place the mycelial discs upside down in the center of the culture medium using an inoculation loop and incubate at 28 °C for 3-7 days. When the control group colonies grow to a diameter of 5.0-7.0 cm, measure the diameter twice using a ruler using the cross-hatching method. Calculate the colony diameter using the average value. We initially selected a concentration of 50 μg / mL for the screening test. ECMO was only performed when the target compound at this concentration showed an inhibition rate greater than 80% against the corresponding pathogen. 50 The mycelial growth inhibition rate was calculated using the following formula. Azoxystrobin, dimethomorph, and cyazofamid were used as control agents in the test. The calculation formula is as follows:

[0067] Inhibition rate (%) = (C1-C2) / (C1-0.5)×100 Where:

[0068] C1 is the control colony diameter, i.e., the colony diameter of the DMSO treatment (i.e., CK);

[0069] C2 represents the diameter of the treated colonies, i.e., the diameter of the colonies treated with the drug.

[0070] 0.5 is the diameter of the mother mycelium cake.

[0071] PDA medium formulation: potato, agar powder, glucose, magnesium sulfate, potassium dihydrogen phosphate, vitamin B1, natural pH, sterilized (120℃, 30min). 1000mL potato broth: Peel and wash potatoes, shred them, weigh 200g, and boil in 1L of secondary water until the potato shreds can be easily crushed with fingers. Filter through gauze. Weigh 20g of agar powder into a beaker, add a small amount of cold water to disperse, and pour into the boiling potato solution. Cook until the agar powder dissolves, stirring constantly and rapidly. Weigh 20g of glucose, 1.5g of magnesium sulfate, 3.0g of potassium dihydrogen phosphate, and 10mg of vitamin B1, add to the filtrate, stir to dissolve, add secondary water to 1L, maintain natural pH, and while still hot, dispense 90mL into 200mL Erlenmeyer flasks. Seal with a semi-permeable filter membrane and autoclave at 120℃ for 30min.

[0072] The embodiments of this invention are provided to illustrate the technical solutions of this invention, but the content of the embodiments is not limited thereto. The experimental results of the target compound are shown in Tables 3 and 4.

[0073] Table 3. Inhibitory activities of all target compounds against seven plant pathogenic fungi (50 μg / mL)

[0074]

[0075]

[0076] As shown in Table 3, most compounds exhibited good antifungal activity against the seven tested plant pathogenic fungi in the in vitro experiments. Compound 28 showed significant antifungal activity against *Rhizoctonia solani*, with an inhibition rate of 100% at 50 μg / mL, significantly superior to commercial fungicides such as pyraclostrobin (81.8%), dimethomorph (54.2%), and cyazofamid (70.6%). Compounds 29 and 35 also demonstrated excellent antifungal activity against the aforementioned seven fungi. To further investigate the antifungal activity of the highly active compounds, ECMO studies were conducted on the target compounds in Table 3 with inhibition rates greater than or equal to 80%. 50 The values ​​were determined, and the results are shown in Table 4.

[0077] Table 4. EC50 of the highly active compounds of this invention against seven plant pathogenic fungi. 50

[0078]

[0079]

[0080]

[0081] As shown in Table 4, compound 35 exhibits excellent antibacterial activity against all seven fungi mentioned above, with its EC50 concentration against all seven fungi being [missing information].50 The concentration ranges from 0.34 to 7.38 μg / mL, especially against Sclerotinia sclerotinia, the causal agent of rapeseed rot (EC). 50 =0.34 μg / mL), exhibiting significant antibacterial activity, which is significantly superior to the commercial drug cyazofamid (EC). 50 =16.6 μg / mL); compounds 25, 29, 33 and 35 all exhibited excellent activity against Staphylococcus aureus, with EC50 values ​​of 16.6 μg / mL. 50 The concentration ranged from 1.89 to 3.15 μg / mL, which was superior to that of the commercial azoxystrobin (EC). 50 =3.19 μg / mL) and cyazofamid (EC) 50 =3.74 μg / mL); Compounds 29 and 35 showed significant antibacterial activity against Tobacco Star Bacterium, with EC50 of 3.74 μg / mL. 50 The concentrations were 1.98 and 1.49 μg / mL, respectively, significantly superior to the commercial drug cyazofamid (EC). 50 =10.5 μg / mL).

[0082] Therefore, it can be seen that such compounds have great research potential and can be used to prepare pesticides against pathogenic fungi in plants.

[0083] 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.

Claims

1. A carbonyl-containing structure α , β -An unsaturated amide or hydrazide compound, characterized in that: selected from the group consisting of: 。 2. A composition characterized in that The compound according to claim 1, and an agriculturally acceptable adjuvant or bactericide, insecticide or herbicide.

3. A composition according to claim 2, wherein: The dosage form of the composition is selected from the group consisting of emulsifiable concentrate, powder, wettable powder, granule, aqueous agent, suspension, ultra-low volume spray, soluble powder, microcapsule, smoke agent, emulsion, water dispersible granule.

4. Use of a compound according to claim 1 or a composition according to claim 2 for controlling plant diseases in agriculture, characterized in that: The plant fungal disease is caused by E. necator, M. grisea, G. zeae, T. gamsii, P. brassicae, A. alternata, wherein the compound for E. necator is compound 4, 11, 15, 16, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35; the compound for M. grisea is compound 4, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35; the compound for G. zeae is compound 2, 3, 4, 10, 11, 12, 13, 14, 15, 16, 21, 22, 25, 26, 28, 29, 32, 33, 34, 35; the compound for T. gamsii is compound 1, 2, 3, 4, 5, 9, 10, 11, 12, 15, 16, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35; the compound for P. brassicae is compound 3, 4, 11, 16, 21, 22, 23, 24, 25, 26, 35, 37, 38, 39; the compound for A. alternata is compound 3, 4, 15, 16, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35; the compound for V. albo-atrum is compound 3, 4, 9, 10, 11, 12, 13, 14, 15, 16, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35.

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