Pleuromutilin compound and use thereof

Abstract

The present invention belongs to the technical field of pesticides and specifically relates to a pleuromutilin compound, a preparation method therefor, and an antimicrobial composition and use thereof. The compound is represented by general formula I, where R1 represents alkyl, alkenyl, or alkynyl, and R1 is not methyl; R2 represents hydrogen, halogen, alkyl, alkenyl, alkynyl, or alkoxy; R8 represents hydrogen, alkyl, alkenyl, or alkynyl; and R3, R4, R5, R6, and R7 each independently represent hydrogen, halogen, alkyl, alkenyl, or the like. The compound exhibits good control activity against various fungi and bacteria.

Description

Pleurotin compounds and their applications Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a truncated pleurotin compound and its application. Background Technology

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term residues. Therefore, despite the large number of known fungicides, there is a need to develop new pest control agents with low toxicity and low residue. Summary of the Invention

[0003] To address the aforementioned problems in the prior art, this invention provides a truncated pleurotin compound and its applications. The compound exhibits good preventative and therapeutic activity against fungi and bacteria.

[0004] The technical solution adopted in this invention is as follows:

[0005] A truncated pleurotin compound, as shown in general formula I:

[0006] Wherein, R1 represents alkyl, alkenyl or alkynyl, and R1 is not methyl;

[0007] R2 represents hydrogen, halogen, alkyl, alkenyl, alkynyl, or alkoxy.

[0008] R8 represents hydrogen, alkyl, alkenyl, or alkynyl;

[0009] R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2;

[0010] The aforementioned "cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R;

[0011] R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl group substituted with at least one group selected from halogen, hydroxyl, alkoxy, amino, alkylamino, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0012] In one specific embodiment, R1 represents a C2-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

[0013] R2 represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C1-C8 alkoxy.

[0014] R8 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

[0015] R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R) )2; The C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR or -(CO)N(R)2;

[0016] The aforementioned “C3-C8 cycloalkyl”, “heterocyclic” or “aryl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R;

[0017] R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, amino, C1-C8 alkylamino, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

[0018] In another specific embodiment, R1 represents a C2-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

[0019] R2 represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy.

[0020] R8 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

[0021] R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R) )2; The C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR or -(CO)N(R)2;

[0022] The aforementioned “C3-C6 cycloalkyl”, “heterocyclic” or “aryl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R;

[0023] R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0024] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. Alkyl groups are, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. The alkynyl group is, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position within each unsaturated group. The cycloalkyl group is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, the cycloalkenyl group is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where double bonds can be in any position. The halogen is fluorine, chlorine, bromine, or iodine.

[0025] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0026] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0027] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0028] Compounds of Formula I, in their respective free or salt forms, and where appropriate, their tautomers, may exist as one of the possible isomers or as mixtures thereof, for example, as pure isomers, such as enantiomers and / or diastereomers, or as mixtures of isomers, such as mixtures of enantiomers, such as racemic mixtures, diastereomer mixtures, or racemic mixtures, depending on the number of asymmetric carbon atoms present in the molecule, their absolute and relative configurations, and / or on the configuration of the non-aromatic double bonds present in the molecule; the present invention relates to these pure isomers and also to all possible mixtures of isomers and should be understood in this sense in each of the above and below, even if stereochemical details are not specifically mentioned in each case. The present invention therefore covers all such isomers and tautomers and mixtures thereof in all proportions, together with isotopic forms, such as deuterated compounds.

[0029] In another embodiment, Formula I is also understood to include their salts or hydrates. Exemplary salts include, but are not limited to, hydrochlorides, hydrobroms, and hydroiodates.

[0030] Those skilled in the art will also understand that, unless otherwise stated, additional substitutions are permitted, provided that the chemical bonding and strain energy rules are satisfied and the product still exhibits bactericidal activity.

[0031] Another embodiment of this application is a method for preparing the truncated pleurotin compound, comprising the following steps:

[0032] The compound of general formula II is reacted with the compound of general formula III to prepare the compound of general formula I, and the reaction equation is as follows:

[0033] The definitions of substituents R1, R2, R3, R4, R5, R6, R7, and R8 are as described above.

[0034] In one specific embodiment, the reaction is carried out in the presence of a base and a solvent.

[0035] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA, etc.

[0036] In another specific embodiment, the solvent is an organic solvent / water, wherein the organic solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0037] Another embodiment of this application is the use of the compound of formula I for protecting plants from plant pathogens or for treating plants affected by plant pathogens, said use including applying the compound of formula I or a composition containing said compound to soil, plants, parts of plants, leaves, and / or roots.

[0038] Another embodiment of this application is a composition for protecting plants from plant pathogenic microorganisms and / or treating plants infected by plant pathogenic microorganisms, said composition comprising a compound of formula I and a botanically acceptable carrier substance.

[0039] The present invention further relates to a crop protection composition for controlling unwanted microorganisms, particularly unwanted fungi and bacteria, comprising an effective and non-phytotoxic amount of the active ingredient of the invention. These are preferably fungicidal compositions comprising agriculturally suitable adjuvants, solvents, carriers, surfactants, or extenders.

[0040] In the context of this invention, "control of harmful microorganisms" refers to a reduction in the infection rate of harmful microorganisms compared to untreated plants, as a measure of bactericidal efficacy. Preferably, this reduction is 25-50% compared to untreated plants (100%), more preferably 40-79%, and even more preferably, the infection rate of harmful microorganisms is completely suppressed (70-100%). This control can be therapeutic, i.e., used to treat infected plants, or protective, used to protect plants that have not yet been infected.

[0041] "Effective but non-phytotoxic amount" refers to the amount of the composition of the present invention that is satisfactory enough to control or completely eliminate fungal / bacterial diseases of plants without causing any significant phytotoxic symptoms. In general, this application rate can vary over a relatively wide range. It depends on several factors, such as the fungus / bacterium being controlled, the plant, climatic conditions, and the composition of the present invention.

[0042] Suitable organic solvents include all polar and nonpolar organic solvents commonly used for pharmaceutical purposes. Preferably, the solvents are selected from ketones, such as methyl isobutyl ketone and cyclohexanone; amides, such as dimethylformamide and alkylcarboxylic acid amides, such as N,N-dimethyldecylamide and N,N-dimethyloctylamide; cyclic solvents, such as N-methylpyrrolidone, N-octylpyrrolidone, N-dodecylpyrrolidone, N-octylcaprolactam, N-dodecylcaprolactam and butyrolactone; strongly polar solvents, such as dimethyl sulfoxide; aromatic hydrocarbons, such as xylene, Solvesso®; mineral oils, such as petroleum solvent oils, petroleum; alkylbenzenes and spindle oils; esters, such as propylene glycol monomethyl ether acetate, dibutyl adipate, hexyl acetate, heptyl acetate, tributyl citrate and dibutyl phthalate; and alcohols, such as benzyl alcohol and 1-methoxy-2-propanol.

[0043] According to the present invention, the carrier is a natural or synthetic, organic or inorganic substance, which is mixed or combined with the active ingredient to obtain better applicability, particularly for application to plants or plant parts or seeds. The carrier may be solid or liquid, is generally inert, and should be suitable for use in agriculture.

[0044] Useful solid or liquid carriers include, for example, ammonium salts and natural rock dusts such as kaolin, clay, talc, chalk, quartz, palygorskite, montmorillonite, or diatomaceous earth, and synthetic rock dusts such as finely dispersed silica, alumina, and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral oils and vegetable oils, and their derivatives. Mixtures of the aforementioned carriers may also be used.

[0045] Suitable solid fillers and carriers include inorganic particles with an average particle size of 0.005-20 micrometers, preferably 0.02-10 micrometers, such as carbonates, silicates, sulfates and oxides, such as ammonium sulfate, ammonium phosphate, urea, calcium carbonate, calcium sulfate, magnesium sulfate, magnesium oxide, aluminum oxide, silica, so-called fine-particle silica, silica gel, natural or synthetic silicates, and aluminosilicates and plant products such as cereal flour, wood flour / wood chips and cellulose powder.

[0046] Useful solid carriers for granulation include, for example, crushed and graded natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, as well as synthetic granules of inorganic and organic powders, and granules of organic matter such as sawdust, coconut shells, corn cobs, and tobacco stems.

[0047] Useful liquefied gas propellants or carriers are those liquids that are gaseous at standard temperatures and pressures, such as aerosol propellants like halogenated hydrocarbons, as well as butane, propane, nitrogen, and carbon dioxide.

[0048] Thickeners, such as carboxymethyl cellulose, can be used in the formulation, as well as natural and synthetic polymers in powder, granule, or latex form, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, or other natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Further additives may include mineral oils and vegetable oils.

[0049] If the extender used is water, organic solvents, for example, can be used as co-solvents. Useful liquid solvents include: aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalenes; chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzenes, vinyl chlorides, or dichloromethane; aliphatic hydrocarbons such as cyclohexane or paraffins; mineral oil fractions, mineral oils, and vegetable oils; alcohols such as butanol or diols and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; highly polar solvents such as dimethylformamide and dimethyl sulfoxide; and water.

[0050] Suitable surfactants (auxiliaries, emulsifiers, dispersants, protective colloids, wetting agents, and binders) include all common ionic and nonionic substances, such as ethoxylated nonylphenols, polyalkylene glycol ethers of linear or branched alcohols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, reaction products of fatty acid amines with ethylene oxide and / or propylene oxide, as well as fatty acid esters, alkyl sulfonates, alkyl sulfates, alkyl ether sulfates, alkyl ether phosphates, aryl sulfates, ethoxylated arylalkylphenols, such as tristyryl-phenol-ethoxylated compounds, and ethoxylated and propoxylated arylalkylphenols such as sulfated or phosphorylated arylalkylphenol-ethoxylated and -ethoxy- and -propoxylated compounds. Further examples are natural and synthetic water-soluble polymers such as lignin sulfonates, gelatin, gum arabic, phospholipids, starch, hydrophobically modified starch, and cellulose derivatives, particularly cellulose esters and cellulose ethers; further, polyvinyl alcohol, polyvinyl acetate, polyvinylpyrrolidone, polyacrylic acid, polymethacrylic acid, and copolymers of (meth)acrylic acid and (meth)acrylates; further, copolymers of methacrylic acid and methacrylates neutralized with alkali metal hydroxides; and condensation products of optionally substituted naphthalene sulfonates with formaldehyde. The presence of a surfactant is necessary if one of the active ingredients and / or one of the inert carriers is insoluble in water and when applied in water. The surfactant is present in a proportion of 5-40% by weight of the composition of the invention.

[0051] Dyes, such as inorganic pigments like iron oxide, titanium dioxide, and Prussian blue, and organic dyes like alizarin dyes, azo dyes, and metal phthalocyanine dyes, as well as micronutrients like iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts, and zinc salts, can also be used.

[0052] Defoamers that may be present in formulations include, for example, silicone emulsions, long-chain alcohols, fatty acids and their salts, as well as fluorinated organic substances and mixtures thereof.

[0053] Examples of thickeners are polysaccharides, such as xanthan gum or magnesium aluminum silicate (veegum), silicates, such as palygorskite, bentonite, and fine-grained silica.

[0054] Other auxiliary ingredients may also be present, if appropriate, such as protective colloids, adhesives, glues, thickeners, thixotropic substances, penetrants, stabilizers, chelating agents, and complexing agents. In general, the active ingredient may be combined with any solid or liquid additives commonly used for formulation purposes.

[0055] The active ingredients or compositions of the present invention may be used in this manner, or, depending on their specific physical and / or chemical properties, in their formulation or in the form of preparation thereof, such as aerosols, capsule suspensions, cold fog concentrators, warm fog concentrators, encapsulated granules, fine granules, flowable concentrates for seed treatment, ready-to-use solutions, pulverizable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, large granules, microparticles, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible solutions, gases ( Under pressure, gas generating products, foaming agents, pastes, pesticide-coated seeds, suspension concentrates, suspension emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble and water-dispersible granules or tablets, water-soluble and water-dispersible powders for seed treatment, wettable powders, natural and synthetic substances impregnated with active ingredients, as well as microcapsules in polymeric substances and in coating materials for seeds, and ULV cold fog and warm fog formulations.

[0056] The compositions of this invention include not only ready-to-use formulations that can be applied to plants or seeds using suitable equipment, but also commercial concentrates that must be diluted with water before use. Conventional applications include, for example, spraying a solution obtained by dilution in water, applying it after dilution in oil, applying it directly without dilution, seed treatment, or soil application of granules.

[0057] The compositions and formulations of the present invention generally contain 0.05-99% by weight, 0.01-98% by weight, preferably 0.1-95% by weight, more preferably 0.5-90% by weight, and most preferably 10-70% by weight of the active ingredient. For specific applications, such as for the protection of wood and derived timber products, the compositions and formulations of the present invention generally contain 0.0001-95% by weight, preferably 0.001-60% by weight of the active ingredient.

[0058] The content of the active ingredient in the application form prepared from commercially available formulations can vary within a wide range. The concentration of the active ingredient in the application form is generally 0.000001-95% by weight, preferably 0.0001-2% by weight.

[0059] The formulations mentioned can be prepared in ways known per se, such as by mixing the active ingredient with at least one conventional extender, solvent or diluent, adjuvant, emulsifier, dispersant, and / or binder or fixative, wetting agent, waterproofing agent, if appropriate, drying agent and UV stabilizer, and if appropriate, dyes and pigments, defoamers, preservatives, inorganic and organic thickeners, binders, gibberellins, and further processing aids and water. Depending on the type of formulation to be prepared, further processing steps may be necessary, such as wet milling, dry milling, and granulation.

[0060] The active ingredients of this invention may exist as such or as mixtures with other (known) active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners, and / or chemical pheromones, in their (commercial) formulations and in use forms prepared from these formulations. Examples of known fungicides, insecticides, acaricides, nematicides, and bactericides are disclosed in the 17th edition of the Pesticide Manual.

[0061] Other fungicides may include: 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, and Bacillus subtilis strain QST713. QST713), benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl compounds, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, lime sulfur. Polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper tanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid.Cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion), diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base Freebase), edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide Hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorphFluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, triethylamine Fosetyl, Fosetyl-aluminium, Fuberidazole, Furalaxyl, Furametpyr, Guazatine, Guazatine acetates, Sodium tetrasulfide (GY-81), Hexachlorobenzene, Hexaconazole, Hymexazol, Imazalil, Imazalil sulfate sulfate), imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isothiazine, kasugamycin, kasugamycin hydrochloride hydrate), kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxideMercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofuronamide, oleic acid (fatty acid) Acid), Oxysastrobin, Oxadixyl, Oxine-copper, Oxpoconazole fumarate, Oxycarboxin, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentachlorophenol, Pentachlorophenyl laurate, Penthiopyrad, Phenylmercuryacetate, Phosphonic acid, Phthalide, Picoxystrobin, Polyoxin B, Polyoxins, Polyoxorim, Potassium bicarbonate, Potassium hydroquinoline sulfate), allylbenzazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb,Proquinazid, prothioconazole, piraclostrobin, pirametostrobin, piraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutriasachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate Bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, wood tar, tebuconazole, tebufloquin, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triad... imenol), triazoloxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophilaThe fungus causing wilt (Fusarium oxysporum), *Gliocladium* spp., *Phlebiopsis gigantea*, *Streptomyces griseoviridis*, *Trichoderma* spp., (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate hydrate), 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate Silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanate, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzalkonium chloride; benzamacril-isobutyl benzamacrilBenzamorf, binapacryl, bis(methylmercury)sulfate, bis(tributyltin)oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, cufraneb, copper hydrazine sulfate Sulfate), Copper chloride (cuprobam), Cycloafuramid, Cypendazole, Cyprofuram, Decafentin, Dichloronaphthoquinone, Dichlozoline, Diclobutrazol, Dimethirimol, Diocton, Dinosulfon, Dinoterbon, Dipyrithione, Ditalimfos, Dodicin, Drazoxolon, E. coli BP), ESBP, eticonazole, etem, ethirim, fenaminosulf, fenapanil, finitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, propiconazole (ICIA0858),Isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenylsuccinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel di(dimethyldithiocarbamate) Bis(dimethyldithiocarbamate), octachlorophenone (OCH), phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, piracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylamide e), azoxystrobin (SSF-109), sulfadiazine (sultropen), tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trihlamide,Urbacid, Zarilamid, and any combination thereof.

[0062] The treatment of plants and plant parts by the active ingredients or compositions of the present invention is carried out directly by conventional treatment methods or by acting on their surrounding environment, habitat, or storage space, such as by impregnation, spraying, atomization, irrigation, evaporation, dusting, spraying, sowing, foaming, spraying, spreading, watering (impregnation), drip irrigation, and in the case of propagation materials, especially seeds, by dry seed treatment, wet seed treatment, slurry treatment, crusting, coating with one or more coatings, etc. The active ingredients can also be spread by ultra-low volume methods or injected into the soil by injecting the active ingredient formulation or the active ingredient itself.

[0063] The active ingredients or compositions of the present invention have strong antimicrobial activity in crop protection and material protection, and can be used to control unwanted microorganisms such as fungi and bacteria.

[0064] The present invention also relates to a method for controlling unwanted microorganisms, characterized in that the active ingredient of the invention is applied to plant pathogenic fungi, plant pathogenic bacteria and / or their habitats.

[0065] Fungicides are used in crop protection to control pathogenic fungi in plants. They are characterized by excellent efficacy against a broad spectrum of plant-pathogenic fungi, including soil-borne pathogens, particularly members of the following classes: Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (Syn. Fungiimperfecti). Some fungicides are systemically active and can be used as foliar, seed-treating, or soil fungicides for plant protection. Furthermore, they are suitable for controlling fungi, especially those infecting wood or plant roots.

[0066] Fungicides can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[0067] Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include:

[0068] Diseases caused by powdery mildew pathogens, such as species of the genus *Blumeria*, such as *Blumeria graminis*; species of the genus *Podosphaera*, such as *Podosphaera leucotricha*; species of the genus *Sphaerotheca*, such as *Sphaerotheca fuliginea*; and species of the genus *Uncinula*, such as *Uncinula necator*.

[0069] Diseases caused by rust pathogens include species of the genus *Gymnosporangium*, such as *Gymnosporangium sabinae*; species of the genus *Hemileia*, such as *Hemileia vastatrix*; species of the genus *Phakopsora*, such as *Phakopsora pachyrhizi* and *Phakopsora meibomiae*; species of the genus *Puccinia*, such as *Puccinia recondite*, *P. triticina*, *P. graminis*, or *P. striiformis*; and species of the genus *Uromyces*, such as *Uromyces appendiculatus*.

[0070] Diseases caused by pathogens of the Oomycetes class, such as species of Albugo, such as Algubo candida; species of the genus Bremia, such as Bremia lactucae; species of the genus Peronospora, such as Peronospora pisi or P. brassicae; species of the genus Phytophthora, such as Phytophthora infestans; species of the genus Plasmopara, such as Plasmopara viticola; species of the genus Pseudoperonospora, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; and species of the genus Pythium, such as Pythium ultimum.

[0071] Leaf spot and leaf blight are caused by pathogens such as: *Alternaria* species, for example, *Alternaria solani* (tomato early blight); *Cercospora* species, for example, *Cercospora beticola* (spinach brown spot); *Cladiosporum* species, for example, *Cladiosporium cucumerinum*; *Cochliobolus* species, for example, *Cochliobolus sativus* (conidial form: *Drechslera*, synonyms: *Helminthosporium*, *Cochliobolus miyabeanus*); *Colletotrichum* species, for example, *Colletotrichum lindemuthanium*; and *Cycloconium* species, for example, *Cycloconium* (olive fowl spot). oleaginum); species of gummosis fungi (Diaporthe), such as *Diaporthe citri*; species of *Elsinoe*, such as *Elsinoe fawcettii*; species of *Gloeosporium*, such as *Gloeosporium laeticolor*; species of *Glomerella*, such as *Glomerella cingulata*; species of *Guignardia*, such as *Guignardia bidwelli*; species of *Leptosphaeria*, such as *Leptosphaeria maculans* and *Leptosphaeria nodorum*; species of *Magnaporthe*, such as *Magnaporthe* (rice blast fungus). grisea); Pythium species, such as Microdochium nivale; Mycosphaerella species, such as Mycosphaerella graminicola, M. arachidicola and M.fijiensi; species of the genus *Phaeosphaeria*, such as *Phaeosphaeria nodorum*; species of the genus *Pyrenophora*, such as *Pyrenophora teres*, *Pyrenophora tritici repentis*; species of the genus *Ramularia*, such as *Ramularia collo-cygni*, *Ramularia areola*; species of the genus *Rhynchosporium*, such as *Rhynchosporium secalis*; species of the genus *Septoria*, such as *Septoria apii*, *Septoria lycopersii*; species of *Typhula*, such as *Typhula incarnata*; species of the genus *Venturia*, such as *Venturia aubergine*. (inaequalis);

[0072] Root and stem diseases caused by pathogens such as: Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Rhizoctonia species, such as Rhizoctonia solani; rice sheath rot caused by Sarocladium oryzae; Sclerotium disease caused by Sclerotium oryzae; Tapesia species, such as Tapesia acuformis; and Thieviopsis species, such as Thieviopsis basicola.

[0073] Ear and inflorescence diseases (including corn cob diseases) are caused by the following pathogens: Alternaria species, such as Alternaria spp.; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; and Septoria species, such as Septoria nodorum.

[0074] Diseases caused by smut fungi include species of the genus *Sphacelotheca*, such as *Sphacelotheca reiliana*; species of the genus *Tilletia*, such as *Tilletia caries*, *T. controversa*; species of *Urocystis*, such as *Urocystis occulta*; and species of the genus *Ustilago*, such as *Ustilago nuda*, *U. nuda tritici*.

[0075] Fruit rot can be caused by pathogens such as Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species, such as Penicillium expansum and P. purpurogenum; Sclerotinia species, such as Sclerotinia sclerotiorum; and Verticilium species, such as Verticilium alboatrum.

[0076] Seed and soil-borne rot, mold, wilting, decay, and damping-off are caused by pathogens such as: species of the genus *Alternaria*, for example, *Alternaria brassicicola*; species of the genus *Aphanomyces*, for example, *Aphanomyces euteiches*; species of the genus *Ascochyta*, for example, *Ascochyta lentis*; species of the genus *Aspergillus*, for example, *Aspergillus flavus*; species of the genus *Cladosporium*, for example, *Cladosporium herbarum*; and species of the genus *Cochliobolus*, for example, *Cochliobolus granatum*. Caused by *Sativus* (conidial form: *Drechslera*, *Bipolaris*; synonym: *Helminthosporium*); species of the genus *Colletotrichum*, such as *Colletotrichum coccodes*; species of the genus *Fusarium*, such as *Fusarium culmorum*; species of the genus *Gibberella*, such as *Gibberella zeae*; species of the genus *Macrophomina*, such as *Macrophomina phaseolina*; species of the genus *Monographella*, such as *Monographella nivalis*; species of the genus *Penicillium*, such as *Penicillium expansum*; species of the genus *Phoma*, such as *Phoma nigra*. Caused by: *Lingam*; species of the genus *Phomopsis*, such as *Phomopsis sojae*; species of the genus *Phytophthora*, such as *Phytophthora cactorum*; species of the genus *Pyrenophora*, such as *Pyrenophora graminea*; species of the genus *Pyricularia*, such as *Pyricularia oryzae*.Species of the genus *Pythium*, such as *Pythium ultimum*; species of the genus *Rhizoctonia*, such as *Rhizoctonia solani*; species of the genus *Rhizopus*, such as *Rhizopus oryzae*; species of the genus *Sclerotium*, such as *Sclerotium rolfsii*; species of the genus *Septoria*, such as *Septoria nodorum*; species of the genus *Typhula*, such as *Typhula incarnata*; and species of the genus *Verticillium*, such as *Verticillium dahliae*.

[0077] Cancer, gall and wilting diseases caused by the following pathogens: for example, species of the genus *Nectria*, such as *Nectria galligena*.

[0078] Wilt caused by species of the genus *Monilinia*, such as *Monilinia laxa*;

[0079] Leaf blister or leaf curl disease can be caused by pathogens such as: species of Exobasidium, such as Exobasidium vexans; species of Taphrina, such as Taphrina deformans.

[0080] Decay diseases of woody plants caused by the following pathogens: for example, Esca caused by *Phaemoniella clamydospora*, *Phaeoacremonium aleophilum*, and *Fomitiporia mediterranea*; grape dyeback caused by *Eutypa lata*; Ganoderma diseases caused by *Ganoderma boninense*; and Rigidoporus diseases caused by *Rigidoporus lignosus*.

[0081] Flower and seed diseases, such as those caused by Botrytis diseases, such as Botrytis cinerea;

[0082] Rhizomatous diseases are caused by the following pathogens: for example, species of the genus Rhizoctonia, such as Rhizoctonia solani; species of the genus Helminthosporium, such as Helminthosporium solani.

[0083] For example, clubroot disease caused by species of the genus Plasmodiophora, such as Plasmodiophora brassicae;

[0084] Diseases caused by the following bacterial pathogens: for example, species of Xanthomonas, such as Xanthomonas campestris pv. oryzae, the pathogen that causes bacterial blight of rice; species of Pseudomonas, such as Pseudomonas syringae pv. lachrymans; and species of Erwinia, such as Erwinia amylovora.

[0085] The following soybean diseases can be preferentially controlled:

[0086] Fungal diseases affecting leaves, stems, pods, and seeds, such as Alternaria leaf spot (Alternaria spec.atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), peach leaf spot and blight (Cercospora kikuchii), leaf blight of the genus *Choanephora* (Choanephora infundibulifera trispora (Syn.)), leaf spot of *Dactuliophora* (Dactuliophora glycines), downy mildew of soybean (Peronospora manshurica), leaf blight of *Drechslera* (Drechslera glycini), and frog-eye disease (Cercospora glycines). Soybean leaf spot (Leptosphaerulina trifolii), soybean leaf spot (Phyllosticta sojaecola), pod and stem wilt (Phomopsis sojae); powdery mildew (Microsphaera diffusa), spinosa leaf spot (Pyrenochaeta glycines), aboveground leaf blight, leaf blight and damping-off (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), black spot (Sphaceloma glycines), leaf blight (Stemphylium botryosum), target spot (Corynespora). cassiicola).

[0087] Fungal diseases affecting the roots and stem base, such as those caused by the following fungi, include: black root rot (Calonectria crotalariae), anthracnose (Macrophomina phaseolina), Fusarium wilt or wilting, root rot, and pod and root collar rot caused by fungi such as Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti, Mycoleptodiscus root rot, Neocosmospora (infecting Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), and stem canker (Diaporthe phaseolorum). Phytophthora megasperma (var. caulivora), Phytophthora megasperma (var. caulivora), Phytophthora gregata (var. gregata), Pythium aphanidermatum (var. aphanidermatum), Pythium irregulare (var. ir. loc. loc. loc. loc. debaryanum), Pythium myriotylum (var. loc. loc. ultimum), Rhizoctonia solani (var. loc ...

[0088] The fungicidal compositions of the present invention can be used for the treatment or protection / preventive control of plant pathogenic fungi / bacteria. The present invention also relates to methods for the treatment and protection of plant pathogenic fungi / bacteria using the active ingredients or compositions of the present invention, by applying said active ingredients or compositions to seeds, plants or plant parts, fruits, or soil in which the plants grow.

[0089] The fact that plants have good tolerance to the active ingredient at the concentrations required to control plant diseases allows for treatment of the above-ground parts of the plant, propagating stems and seeds, as well as the soil.

[0090] According to the present invention, all plants and plant parts can be processed. Plants refer to all plants and plant populations, such as desired and undesirable wild plants, cultivated plants, and plant varieties (whether or not protected by the rights of plant varieties or plant breeders). Cultivated plants and plant varieties can be plants obtained through conventional propagation and breeding methods, which can be aided or supplemented by one or more of the following biotechnological methods, for example: using double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers, or utilizing bioengineering and genetic engineering methods. Plant parts refer to all above-ground and underground parts as well as plant organs, such as buds, leaves, flowers, and roots, including, for example, leaves, needle-like leaves, stems, trunks, flowers, fruit bodies, fruits, and seeds, as well as roots, bulbs, and rhizomes. Crops, as well as asexual and sexual propagation materials, such as cuttings, bulbs, rhizomes, stolons, and seeds, are also considered plant parts.

[0091] The active ingredients of this invention, when well tolerated by plants, exhibit favorable warm-blooded toxicity and good environmental tolerance, making them suitable for protecting plants and plant organs to increase harvest yield and improve the quality of harvested material. They can be preferably used as crop protection compositions. They are active against normally sensitive and resistant species, as well as against all or some developmental stages.

[0092] The plants that can be processed according to the present invention include the following major crop plants: corn, soybean, alfalfa, cotton, sunflower, Brassica oilseeds, such as Brassica napus (e.g., Corona rape), Brassica rapa, B. juncea (e.g., field mustard) and Brassica carinata, Arecaceae (e.g., oil palm, coconut), rice, wheat, sugar beets, sugarcane, oats, rye, barley, millet and sorghum, triticale, flax, nuts, grapes and vines, and various fruits and vegetables from various plant groups, such as Rosaceae (e.g., pome fruits, such as apples and pears, but also nut fruits, such as apricots, cherries, almonds, plums and peaches, and berry fruits, such as strawberries, Trichoderma, red and blackcurrants and currants), Ribesioidae. Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp. (e.g., olive trees), Actinidaceae sp., Lauraceae sp. (e.g., avocados, cinnamon, camphor), Musaceae sp. (e.g., banana trees and other plants), Rubiaceae sp. (e.g., coffee), Theaceae sp. (e.g., tea), Sterculiaceae sp., Rutaceae sp. (e.g., lemons, oranges, tangerines, and grapefruits); Solanaceae sp. (e.g., tomatoes, potatoes, peppers, chili peppers, eggplants, tobacco), Liliaceae sp., Compositae (e.g., lettuce, artichoke, and chicory—including root chicory, endive, or common chicory), Apiaceae (e.g., carrots, cilantro, celery, and root celery), Cucurbitaceae (e.g., cucumbers—including cucumbers, squash, watermelons, gourds, and honeydew melons), Alliaceae (e.g., onions and leeks), Cruciferae (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, turnips, radishes, wasabi, watercress, and Chinese cabbage), and Leguminosae (e.g., legumes).(e.g., peanuts, peas, lentils, and legumes—such as common beans and broad beans); Chenopodiaceae sp. (e.g., Swiss chard, forage beets, spinach, beetroot); Linaceae sp. (e.g., cannabis), Cannabeacea sp. (e.g., cannabis), Malvaceae sp. (e.g., okra, cacao), Papaveraceae (e.g., poppy), Asparagaceae (e.g., asparagus); useful and ornamental plants in gardens and woodlands include turf, lawn, grasses, and stevia rebaudiana, as well as genetically modified types of these plants in each case.

[0093] When the active ingredient of this invention is used as a bactericide, the application rate can vary over a relatively wide range, depending on the application type. The application rate of the active ingredient of this invention is:

[0094] • When treating plant parts such as leaves: 0.1-10000 g / ha, preferably 10-1000 g / ha, more preferably 10-800 g / ha, and even more preferably 50-300 g / ha (the application rate can be reduced even when applied by watering or drip irrigation, especially when using inert substrates such as rock wool or perlite).

[0095] • In the case of seed treatment: 2-200g / 100kg of seeds, preferably 3-150g / 100kg of seeds, more preferably 2.5-25g / 100kg of seeds, and even more preferably 2.5-12.5g / 100kg of seeds;

[0096] • In the case of soil treatment: 0.1-10000 g / ha, preferably 1-5000 g / ha.

[0097] The active ingredients or compositions of the present invention can therefore be used to protect plants from the aforementioned pathogens for a period of time after treatment. The period of protection generally extends to 1-28 days, preferably 1-14 days, more preferably 1-10 days, most preferably 1-7 days, or up to 200 days after seed treatment, following treatment with the active ingredients.

[0098] It will be apparent to those skilled in the art to understand the teachings of this document that any range or desired value given herein can be extended or modified without losing the desired effect. Detailed Implementation

[0099] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0100] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. The specific compound structures and corresponding compound information are shown in Table 1. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0101] Table 1. Compound structures and their properties 1 H NMR

[0102] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0103] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown in the table below are either commercially available or can be easily prepared by those skilled in the art.

[0104] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0105] 1. Synthesis of Compound 2

[0106] (1) Compound 2-1 (100.00 g, 264.19 mmol, 1 eq) was dissolved in DCE, and triethylamine (32.08 g, 317.03 mmol, 1.1 eq) and pyridine (4.18 g, 52.84 mmol, 0.2 eq) were added. TsCl (55.40 g, 290.61 mmol, 1.1 eq) was slowly added under ice bath. The mixture was brought to room temperature and reacted overnight. The reaction was monitored by LC-MS until complete. DCE was then removed by rotary evaporation. The residue was adjusted to pH 4 by adding dilute hydrochloric acid, and extracted with water and EA. The organic phases were combined, dried over anhydrous sodium sulfate, and EA was removed. The mixture was then purified by slurrying with a solvent of DCM:PE = 1:50 to obtain product 2-2 (white solid, 97.02 g, yield 68.92%).

[0107] (2) In a 250 mL single-necked flask, compound 2-2 (5 g, 1.0 eq, 9.39 mmol) was dissolved in 50 mL of methanol, and sodium borohydride (1.78 g, 5 eq, 46.93 mmol) was added. The mixture was stirred at room temperature for 24 hours until the reaction was completed. The reaction solution was poured into 200 mL of saturated ammonium chloride aqueous solution, and the pH was adjusted to 6 with dilute hydrochloric acid. Ethyl acetate was added and extracted twice (200 mL x 2). The organic phase was collected and concentrated under reduced pressure to obtain crude product 2-3 (3.8 g, yield 75%).

[0108] (3) In a 100 mL single-necked flask, compound 2-3 (0.5 g, 1.0 eq, 0.94 mmol) was dissolved in 5 mL of ethyl acetate. Potassium iodide (0.28 g, 1.5 eq, 1.4 mmol) was added, and the mixture was stirred at 70 °C for half an hour. A mixed aqueous solution of 2-4 (0.17 g, 1.5 eq, 1.4 mmol) and sodium hydroxide (0.06 g, 1.5 eq, 1.4 mmol) was added, and the mixture was reacted overnight at 70 °C. After the reaction was completed, the reaction solution was poured into 20 mL of water, and 10 mL x 2 of ethyl acetate was added for extraction. The organic phase was collected, concentrated under reduced pressure, mixed with silica gel, and separated by normal phase column chromatography (PE:EA = 5:1) to obtain compound 2 (0.13 g, purity 99%, yield 28%).

[0109] Bioactivity evaluation:

[0110] Bactericidal activity test - turbidimetric method

[0111] The compound reagent was dissolved in DMSO, and diluted with 0.1% Tween 20 solution. Different mass concentrations were set according to the reagent activity, with three replicates for each treatment group. Each concentration maintained an equal volume of DMSO, and a DMSO blank control was set up at the highest dose. Additionally, a blank reagent control and a DMSO inoculation control were set up, with three replicates for each control group. Under aseptic conditions, sterile NB medium was quantitatively added to sterile shaking tubes for later use. Quantitative amounts of the reagent solution were sequentially pipetted from low to high concentrations and added to the aforementioned shaking tubes, and thoroughly mixed. The control treatment was the same.

[0112] Under aseptic conditions, a quantitative amount of the cultured bacterial solution was taken and added to the above-mentioned shaking tubes containing the reagent, and then placed in a constant temperature shaker at 30°C and 180 rpm for incubation.

[0113] The bacterial culture in the control shake tubes was cultured to the logarithmic growth phase (OD = 0.6-0.8), and the OD values ​​of each treatment and the control were investigated. Based on the investigation results, the inhibition rate of each treatment concentration against the tested target bacteria was calculated according to formulas (1) and (2), in percentage (%). D = D1 - D2…………………………………………(1)

[0114] In the formula:

[0115] D—OD value of the post-treatment bacterial solution;

[0116] D1—OD value of the bacterial solution treated with the agent;

[0117] D2—OD value of blank drug control.

[0118] In the formula:

[0119] I—Inhibition rate;

[0120] D0—OD value of the control bacterial suspension after correction;

[0121] D t — OD value of the post-treatment bacterial solution.

[0122] Table 2. Representative results of bactericidal activity tests (2DAA)

[0123] Note: N represents no data.

[0124] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit good control activity against various fungi and bacteria, including those belonging to the Ascomycetes, Basidiomycetes, Deuteromycetes, and Oomycetes, and thus possess certain commercial value.

Claims

1. A truncated pleurotin compound, as shown in general formula I: in, R1 represents alkyl, alkenyl, or alkynyl, and R1 is not methyl; R2 represents hydrogen, halogen, alkyl, alkenyl, alkynyl, or alkoxy. R8 represents hydrogen, alkyl, alkenyl, or alkynyl; R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2; The aforementioned "cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl group substituted with at least one group selected from halogen, hydroxyl, alkoxy, amino, alkylamino, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The truncated pleurotin compound according to claim 1, characterized in that, R1 represents a C2-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R2 represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, or C1-C8 alkoxy. R8 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R) )2; The C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR or -(CO)N(R)2; The aforementioned "C3-C8 cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, amino, C1-C8 alkylamino, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenylC1-C8 alkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

3. A truncated pleurotin compound according to claim 1 or 2, characterized in that, R1 represents C2-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R2 represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C1-C6 alkoxy. R8 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R3, R4, R5, R6, and R7 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R) )2; The C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(COR), -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR or -(CO)N(R)2; The aforementioned "C3-C6 cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, amino, C1-C6 alkylamino, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, heterocyclic, phenyl, benzyl, or phenyl, benzyl or heterocyclic substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy; Preferably, the compound is selected from any one of the compounds in Table 1 of the specification.

4. A method for preparing the truncated pleurotin compound according to any one of claims 1-3, comprising the following steps: The compound of general formula II is reacted with the compound of general formula III to prepare the compound of general formula I, and the reaction equation is as follows: The substituents R1, R2, R3, R4, R5, R6, R7, and R8 are defined as described in any one of claims 1-3; Preferably, the reaction is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of organic or inorganic bases; the solvent is an organic solvent / water, and the organic solvent is selected from at least one of DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

5. A fungicidal and / or bactericidal composition comprising a truncated pleurotin compound as described in any one of claims 1-3; preferably, further comprising other active ingredients.

6. Use of the truncated pleurotin compound as described in any one of claims 1-3, or the composition as described in claim 5, in the control of plant pathogenic fungi and / or bacteria.

7. A method for preventing harmful fungi and / or bacteria, comprising treating fungi and / or bacteria or materials, plants, soil or seeds to be protected against fungal and / or bacterial invasion with an effective amount of a truncated pleurotin compound as described in any one of claims 1-3, or a composition as described in claim 5.

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