Substituted pyrazole compound containing pyrimidine and use thereof

Abstract

The present invention belongs to the technical field of pesticides and specifically relates to a substituted pyrazole compound containing pyrimidine and a use thereof. The compound is represented by general formula I: where Q represents an aryl group or a heterocyclic group; Y1 and Y2 each independently represent hydrogen, alkyl, or the like; R1 and R2 each independently represent hydrogen, halogen, nitro, or the like; R3 represents hydrogen, alkyl, or the like; R4, R5, R6, and R7 each independently represent hydrogen, alkyl, or halogenated alkyl; and R8 and R9 each independently represent hydrogen, halogen, cyano, alkyl, or the like. The described compound exhibits good control activity against fungi, etc.

Description

Pyrimidine-containing substituted pyrazole compounds and their applications Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a pyrimidine-containing substituted pyrazole 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 persistence. In this context, despite the existence of numerous known fungicides, such as WO2016184378A1 which discloses a pyrimidine-containing substituted pyrazole compound and its application as a fungicide, there is still 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 pyrimidine-containing substituted pyrazole compound and its applications. The compound exhibits good control activity against fungi and other pathogens.

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

[0005] A pyrimidine-containing substituted pyrazole compound, as shown in general formula I:

[0006] Where Q represents aryl or heterocyclic group;

[0007] Y1 and Y2 independently represent hydrogen, alkyl, cycloalkyl, aryl, and -OR, respectively. 10 ,-alkylene-OR 10 -(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom form a heterocyclic group with N at the 1-position;

[0008] R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or substituted -CH=CH-CH=CH-;

[0009] R3 represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10OR-alkylene- 10 ;

[0010] R4, R5, R6, and R7 independently represent hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, or haloynyl, respectively.

[0011] R8 and R9 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ;

[0012] The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced;

[0013] R 10 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0014] In one specific embodiment, Y1 and Y2 independently represent hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, aryl, and -OR, respectively. 10 -(C1-C8 alkylene)-OR 10 -(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom can form a 5-8 membered heterocyclic group with N at the 1-position;

[0015] R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or halogenated -CH=CH-CH=CH-;

[0016] R3 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10 OR -(C1-C8 alkylene)-OR 10 ;

[0017] R4, R5, R6, and R7 independently represent hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, or halo-C2-C8 alkynyl, respectively.

[0018] R8 and R9 independently represent hydrogen, 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, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ;

[0019] The aforementioned C3-C8 cycloalkyl, heterocyclic, or aryl groups are optionally 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, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced;

[0020] R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group 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.

[0021] In another specific embodiment, Y1 and Y2 independently represent hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, and -OR, respectively. 10 -(C1-C6 alkylene)-OR 10-(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom form a 5-6 membered heterocyclic group with an N atom at the 1-position (e.g., unsubstituted or substituted by at least one group selected from halogens, alkyl groups, or haloalkyl groups). );

[0022] R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or halogenated -CH=CH-CH=CH-;

[0023] R3 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10 OR -(C1-C6 alkylene)-OR 10 ;

[0024] R4, R5, R6, and R7 independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, or halo-C2-C6 alkynyl, respectively.

[0025] R8 and R9 independently represent hydrogen, 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, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ;

[0026] The aforementioned C3-C6 cycloalkyl, heterocyclic, or aryl groups are optionally 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, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R10 or -N(R) 10 At least one group in )2 is replaced;

[0027] R 10 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group 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.

[0028] 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. For example, the compound term "-alkylene-OR". 10 "The alkylene group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, 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, the alkenyl group is, 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." -yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, 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 in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, where double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0029] 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

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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.

[0034] Those skilled in the art will also understand that, unless otherwise stated, additional substitutions are permitted, provided that the rules of chemical bonding and strain energy are satisfied and the product still exhibits antifungal activity.

[0035] Another embodiment of this application is a method for preparing the pyrimidine-containing substituted pyrazole compound, comprising the following steps:

[0036] (1) The compound represented by general formula II is reacted with the compound represented by general formula III or its salt (such as hydrochloride) to prepare the compound represented by general formula I. The reaction equation is as follows:

[0037] (2) Alternatively, when Y1 and Y2 are not both H, then... The intermediate was subjected to a substitution reaction to yield compound I.

[0038] In one specific embodiment, (3) the compound represented by general formula V is prepared by reacting the compound represented by general formula VI with the compound represented by general formula VII or a salt thereof (such as hydrochloride), and the reaction equation is as follows:

[0039] Here, Hal and Hal' represent halogens independently, and the substituents Q, R1, R2, R3, R4, R5, R6, R7, R8, R9, Y1, and Y2 are defined as described above.

[0040] In one specific embodiment, both steps (1) and (3) are carried out in the presence of a solvent and a base.

[0041] In another specific embodiment, the solvent is selected from at least one of toluene, DMF, DME, DMA, methanol, ethanol, diethyl ether, dichloroethane, DMSO, dioxane, tetrahydrofuran, dichloromethane, or ethyl acetate.

[0042] In another specific embodiment, the base is selected from at least one of inorganic bases (such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KHCO3, KF, CsF, KI, NaI, K3PO4, K2HPO4, NaOH, KOH, NaH, KH, etc.) or organic bases (such as pyrazole, triethylamine, DIEA, potassium trimethylsilanol, AcOK, AcONa, MeONa, EtONa, t-BuONa, etc.).

[0043] The present invention also provides an intermediate, as shown in Formula II, III or V.

[0044] 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.

[0045] 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.

[0046] The present invention further relates to a crop protection composition for controlling unwanted microorganisms, particularly unwanted fungi, 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.

[0047] 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 fungicidal efficacy. This reduction is preferably 25-50% compared to untreated plants (100%), more preferably 40-79%, and even more preferably, complete inhibition (70-100%) of harmful microorganism infection. The control can be therapeutic, i.e., used to treat infected plants, or protective, used to protect plants that have not yet been infected.

[0048] "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 diseases in 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 being controlled, the plant, climatic conditions, and the composition of the present invention.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] Examples of thickeners are polysaccharides, such as xanthan gum or magnesium aluminum silicate (veegum), silicates, such as palygorskite, bentonite, and fine-grained silica.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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 oleophila.The 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.

[0069] In one specific embodiment, the other active ingredient (active ingredient B) is selected from at least one of the following: ethirimol [23947-60-6], benomyl [220899-03-6], Fluopyram [1228284-64-7], Fluopyram [907204-31-3], Prothioconazole [178928-70-6], Difenoconazole [119446-68-3], Tebuconazole [107534-96-3], Fluopyram [133855-98-8], Propiconazole [60207-90-1], Hexaconazole [79983-71-4], Chlorpyrifos [1417782-03-6], cyproconazole [94361-06-5], cyazofamid [88671-89-0], tebuconazole [83657-24-3], triadimefon [43121-43-3], fenbendazole [76674-21-0], isothiazamide [875915-78-9], chlorpyrifos [902760-40-1], prochloraz [67747-09-5] Trifluopyridine [1460292-16-3], Fluopyram [658066-35-4], Azoxystrobin [131860-33-8], Pyraclostrobin [175013-18-0], Cyazofamid [117428-22-5], Azoxystrobin [143390-89-0], Azoxystrobin [141517-21-7], Iprodione [32809-16-8], Iprodione [24096-53-5], Fludioxonil [131341-86-1], Fluazinam [79622-59-6], Fluopyram [861647-84-9], Pyraclostrobin [881685-58-1], Iprodione [36734-1] 9-7], pyrimethanil [53112-28-0], azoxystrobin [121552-61-2], fluopyram [239110-15-7], cyazofamid [120116-88-3], fluthiazopyr [1003318-67-9], azoxystrobin [865318-97-4], cymoxanil [57966-95-7], mancozeb [8018-01-7], zineb [12122-67-7], thiamethoxam [3052252-63-5], cymoxanil hydrochloride [25606-41-1], metalaxyl [57837-19-1], dimethomorph [110488-70-5], fluopyram [2118 [67-47-9], Dimethomorph [374726-62-2], Metalaxyl [70630-17-0], Oxadiazon [131807-57-3], Azoxystrobin [915410-70-7], Chlorothalonil [1897-45-6], Captan [133-06-2], Mancozeb [3566-10-7], Propineb [12071-83-9], Mancozeb [9006-42-2], Thiram [137-26-8], Hymexazol [10004-44-1], Polyoxin [11113-80-7], Kasugamycin [861228-39-9], Kasugamycin [6980-18-3], Ningnanmycin [156410-09-2], Amino oligosaccharide [148411-57-8], Chitosan [9012-76-4], Aluminum tris(ethylphosphonate) [39148-24-8], Copper quinoline [10380-28-6], Bordeaux mixture [8011-63-0], Copper succinate [604797-07-1], Copper sulfate calcium [129107-12-6], Tricyclazole [41814-78-2], Isoprothiolane [115852-48-7], Isoprothiolane [26087-47-8], Isoprothiolane [50512-35-1], Trifluthoxam [911499-62-2], Allylbenzylthiazide [27605-76-1] Carbendazim [10605-21-7], Thiophanate-methyl [23564-05-8],

[0070] Most of the active ingredients mentioned above are referred to in the text by their so-called “generic name,” the relevant “ISO generic name,” or, in some cases, another “generic name.” If the name is not a “generic name,” the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “traditional name,” “compound name,” or “development code” is used, or if neither of these names nor a “generic name” is used, an “alternative name” is used.

[0071] In each combination, the mass ratio of any two components is chosen to provide a desired, for example, synergistic effect. Generally, this mass ratio will vary depending on the specific components and the amount of each component present in the combination. Generally, in this invention, the mass ratio of active ingredient A (compound of formula I) to active ingredient B can be 1:2000–100:1, 1:1600–50:1, 1:1200–20:1, 1:800–10:1, 1:400–1:1, 1:320–1:2, 1:200–1:2.5, 1:160–1:4, 1:100–1:5, 1:80–1:8, 1:40–1:10, or 1:32–1:20. These mixing ratios are understood to include, on the one hand, a mass ratio, and on the other hand, a molar ratio.

[0072] 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.

[0073] 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.

[0074] 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 and / or their habitats.

[0075] 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.

[0076] Fungicides can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[0077] Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include:

[0078] 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*.

[0079] 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*.

[0080] 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.

[0081] 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);

[0082] 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.

[0083] 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.

[0084] 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*.

[0085] 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.

[0086] 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*.

[0087] Cancer, gall and wilting diseases caused by the following pathogens: for example, species of the genus *Nectria*, such as *Nectria galligena*.

[0088] Wilt caused by species of the genus *Monilinia*, such as *Monilinia laxa*;

[0089] 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.

[0090] 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*.

[0091] Flower and seed diseases, such as those caused by Botrytis diseases, such as Botrytis cinerea;

[0092] 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.

[0093] For example, clubroot disease caused by species of the genus Plasmodiophora, such as Plasmodiophora brassicae.

[0094] The following soybean diseases can be preferentially controlled:

[0095] 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).

[0096] 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 ...

[0097] The fungicidal compositions of the present invention can be used for the treatment or protection / preventive control of plant pathogenic fungi. The present invention also relates to a method of treatment and protection against plant pathogenic fungi by using the active ingredients or compositions of the present invention, wherein said active ingredients or compositions are applied to seeds, plants or plant parts, fruits or soil in which the plants grow.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] When the active ingredient of this invention is used as a fungicide, the application rate can vary over a relatively wide range, depending on the type of application. The application rate of the active ingredient of this invention is:

[0103] • 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).

[0104] • 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;

[0105] • In the case of soil treatment: 0.1-10000 g / ha, preferably 1-5000 g / ha.

[0106] 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.

[0107] 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

[0108] 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.

[0109] 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.

[0110] Table 1. Compound structures and their properties 1 H NMR

[0111] 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.

[0112] 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 below are either commercially available or can be easily prepared by those skilled in the art.

[0113] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0114] 1. Synthesis of Compound 1

[0115] (1) Guanidine hydrochloride (5.9 g, 62 mmol) and potassium tert-butoxide (13.9 g, 123 mmol) were dissolved in 100 ml of n-butanol. The mixture was heated to 120 °C and reacted for 15 min. Then, the mixture was cooled to 60 °C and compound 1-1 (10 g, 62 mmol) was slowly added dropwise and the mixture was reacted overnight. After the reaction was completed under controlled conditions, the mixture was cooled to room temperature and filtered. The pH of the mother liquor was adjusted to about 5 with acetic acid. The n-butanol was then removed by a pump to obtain a yellow crude compound 1-2 (15.0 g, 100%).

[0116] (2) 15 ml of phosphorus oxychloride was added to compound 1-2 (15.0 g, 62 mmol) under ice bath conditions. The mixture was heated to 115 °C and reacted for 30 min, with the reaction controlled to complete. The mixture was cooled to room temperature and poured into an ice bath of sodium bicarbonate to adjust the pH to alkaline. The mixture was extracted three times with ethyl acetate. The combined organic phases were washed three times with saturated sodium chloride solution, dried, and concentrated. Silica gel column chromatography yielded a pale yellow solid, compound 1-3 (4.1 g, 38%).

[0117] (3) Compounds 1-3 (4.1 g, 23 mmol) were dissolved in 60 ml of DMF and stirred until homogeneous. Then, NCS (3.4 g, 26 mmol) was added, and the mixture was stirred at room temperature for 1 h. The reaction was monitored to ensure completeness. Water was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed three times with saturated sodium chloride solution, dried, and concentrated. Silica gel column chromatography yielded a white solid compound 1-4 (3.2 g, 65%).

[0118] (4) Using a single-necked flask, dissolve 1-5 (2.50 g, 14.2 mmol) in tert-butanol, add potassium tert-butoxide (4.80 g, 42.6 mmol) while stirring, lower the temperature to 0°C, then add methyl propargylate (1.20 g, 14.2 mmol), raise the temperature to 65°C, and react for 16 hours. Monitor the reaction for completeness, stir the reaction solution and pass it through a column to obtain 1.29 g of a yellow oily substance 1-6 (yield: 40%).

[0119] (5) Using a single-necked flask, dissolve 1-6 (1.29 g, 5.60 mmol) in tetrahydrofuran, cool to 0 °C, add N-(tert-butyloxycarbonyl)ethanolamine (0.90 g, 5.60 mmol), then add triphenylphosphine (8.40 mmol), then add diisopropyl azodicarbonate (8.40 mmol), and react at room temperature for 16 hours, with the reaction under intermediate control. Once the reaction is complete, stir the reaction mixture and pass it through a column to obtain 0.73 g of a yellow oily substance (yield: 35%).

[0120] (6) Using a single-necked flask, 1-7 (0.73 g, 1.9 mmol) was dissolved in 1,4-dioxane, and 2 M hydrochloric acid / 1,4-dioxane solution (4.0 mmol) was added. The mixture was reacted at room temperature for 16 hours. After monitoring the reaction to ensure it was complete, the reaction solution was evaporated to dryness to give 480 mg of 1-8 as a yellow solid (yield: 80%).

[0121] (7) Compounds 1-4 (150 mg, 0.7 mmol), compounds 1-8 (193 mg, 0.7 mmol), and potassium carbonate (296 mg, 2.4 mmol) were dissolved in 20 mL of DMF. After stirring, the mixture was heated to 80 °C and reacted for 2 h, with complete reaction as monitored. The mixture was then cooled to room temperature, water was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed three times with saturated sodium chloride solution, dried, and concentrated. Silica gel column chromatography yielded a pale yellow solid, compound 1 (85 mg, 27%).

[0122] 2. Synthesis of Compound 23

[0123] At room temperature, compound 23-1 (4.3 g, 20.2 mmol) was dissolved in 20 mL of toluene under nitrogen protection. Compound 23-2 (6.6 g, 24.2 mmol) and triethylamine (8.2 g, 80.8 mmol) were added to the reaction solution. The mixture was stirred at room temperature to 110 °C for 2 hours. After the reaction was completed, water was added, and the mixture was extracted three times with EA. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and purified by normal phase mixing to give compound 23 (white solid, 4 g, 45%).

[0124] 3. Synthesis of compounds 57 and 61

[0125] (1) At room temperature, compound 61-1 (4 g, 17.45 mmol) was dissolved in 40 mL of THF. N-Boc-ethanolamine (4.22 g, 26.18 mmol), triphenylphosphine (9.1 g, 34.9 mmol), and DIAD (7.05 g, 26.18 mmol) were added continuously with stirring. After the addition was complete, the mixture was stirred overnight at room temperature. After the reaction was monitored by LCMS, the mixture was extracted several times with water and EA. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and purified by normal phase mixing to obtain compound 61-2 (yellow oil, 2 g, 31%).

[0126] (2) At room temperature, compound 61-2 (2.0 g, 5.37 mmol) was dissolved in 20 mL HCl / EA and stirred for 3 h. The reaction was then monitored by LCMS to indicate the end of the reaction. The reaction solution was concentrated to remove the organic solvent, yielding crude compound 61-3 (white solid, 1.3 g, 89%).

[0127] (3) Compound 61-3 (600 mg, 2.2 mmol) was dissolved in 10 mL of DMF, and then compounds 1-4 (510 mg, 2.42 mmol) and K2CO3 (910 mg, 6.6 mmol) were added sequentially. After the addition was complete, the mixture was stirred overnight at 80 °C. After the reaction was complete, water was added, and the mixture was extracted three times with EA. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, mixed, and purified under normal phase to obtain compound 61 (white solid, 500 mg, 51%).

[0128] (4) At room temperature, compound 61 (150 mg, 0.34 mmol) was dissolved in 5 mL of DCM, followed by the slow addition of acetyl chloride (32 mg, 0.4 mmol) and triethylamine (103 mg, 1.02 mmol). The reaction was allowed to proceed overnight at room temperature. After the reaction was monitored by LCMS, the mixture was extracted three times with DCM. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and purified by normal phase mixing under cyclone drying. Compound 57 (white solid, 85 mg, 52%) was obtained.

[0129] 4. Synthesis of Compound 72

[0130] (1) Compounds 1-4 (500 mg, 2.39 mmol), cuprous chloride (475 mg, 4.80 mmol), and copper chloride (643 mg, 4.80 mmol) were dissolved in 30 mL MeCN. 368 mg, 3.58 mmol of tert-butyl nitrite was added under ice bath conditions. The reaction was allowed to proceed overnight at room temperature. After complete reaction under controlled conditions, the mixture was dried, concentrated, and mixed. Silica gel column chromatography yielded a pale yellow oily compound 72-1 (185 mg, 34%).

[0131] (2) Compound 72-1 (185 mg, 0.81 mmol), compound 1-8 (219 mg, 0.81 mmol), and potassium carbonate (328 mg, 2.43 mmol) were dissolved in 30 mL of DMF, heated to 80 °C, and reacted overnight. Complete reaction was monitored under intermediate control. The mixture was extracted three times with water and ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated, and mixed. Silica gel column chromatography yielded a pale yellow oily compound 72-2 (200 mg, 53%).

[0132] (3) Compound 72-2 (150 mg, 0.32 mmol) was dissolved in 10 mL of DMF. Potassium carbonate (134 mg, 0.97 mmol) and 1,2,4-triazole (22 mg, 0.32 mmol) were added sequentially with stirring at room temperature. The mixture was then transferred to an oil bath and reacted for 3 h. After the reaction was complete, the reaction solution was extracted three times with EA. The organic phases were combined, washed with saturated brine, concentrated, mixed with silica gel, and purified by column chromatography to obtain a white solid compound 72 (140 mg, 87%).

[0133] Bioactivity evaluation:

[0134] Bactericidal activity test - potted plant method:

[0135] The pesticide was prepared by dissolving dimethyl sulfoxide and diluting it with a 0.1% Tween 80 aqueous solution to different concentrations. The solution was sprayed evenly onto the leaf surface until completely wetted, and then allowed to air dry naturally before use. A blank control (treatment without pesticide) was included. Three controls were set up for each pesticide.

[0136] Inoculation for cucumber downy mildew, cucumber powdery mildew, and wheat leaf rust: The experimental targets should be *Sphaerotheca cucurbitae* (Jacz.) ZYZhao and *Pseudoperonospora cubensis* (Berk. et Curt.) Rostov., cultured on live potted cucumbers or detached leaves; and *Puccinia recondita*, cultured on live potted wheat or detached leaves. Diseased and spore-producing cucumber or wheat leaves should be removed, and after shaking off excess powder, the leaves should be gently tapped with a glass rod to evenly distribute powdery mildew spores onto the test material. Protective experiments should be conducted 24 hours after treatment. After inoculation, the leaves should be placed at approximately 25°C and cultured under alternating light and dark conditions for 12 hours each. Results should be collected after 10 days, and the control efficacy of each treatment should be calculated.

[0137] Cucumber target spot disease inoculation: Protective testing was conducted 24 hours after pesticide treatment. Culture medium was added to a petri dish already contaminated with *Corynespora cassiicola* (Berk. & M.A. Curtis) CTWei spores. Surface spores were gently scraped off, filtered through four layers of gauze, and a concentration of 5 × 10⁻⁶ was prepared. 5 ~1×10 6 A spore suspension of 1 spore / mL was prepared and sprayed onto cucumber seedlings. The inoculated material was then transferred to an incubator or artificial climate chamber for incubation in complete darkness. The control effect was assessed after 7 days.

[0138] Inoculation for wheat scab, rice blast, and potato late blight: Protective tests were conducted 24 hours after pesticide treatment. The test targets should be *Fusarium graminearum*, *Magnaporthe oryzae*, or *Phytophthora infestans* cultured in living pots or on detached leaves. In a petri dish already contaminated with spores, culture medium was added, and surface spores were gently scraped off. After filtration through four layers of gauze, a concentration of 1×10⁻⁶ was prepared. 5 ~5×10 5 A spore suspension of 1 spore / mL was prepared and sprayed onto the host material using a sprayer. The inoculated material was then transferred to an incubator or artificial climate chamber for incubation in complete darkness. The control effect was assessed after 5 days.

[0139] Based on the disease incidence in the blank control group (disease level 9), the inoculated leaves were graded. The following grading method was used:

[0140] Level 0: No disease;

[0141] Grade 1: The area of ​​lesions accounts for less than 5% of the total leaf area;

[0142] Grade 3: The lesion area accounts for 6% to 10% of the total leaf area;

[0143] Level 5: The lesion area accounts for 11% to 25% of the total leaf area;

[0144] Level 7: The lesion area accounts for 26% to 50% of the total leaf area;

[0145] Level 9: The lesion area accounts for more than 50% of the total leaf area.

[0146] Based on the survey data, the disease index and prevention and control effects of each treatment were calculated.

[0147] The disease index is calculated using a formula, and the result is rounded to two decimal places:

[0148] X={(∑(Ni xi)) / (N x 9)}x 100

[0149] In the formula: X—disease index; Ni—number of diseased leaves at each level; i—relative level value; N—total number of leaves surveyed.

[0150] The prevention and control effect is calculated using the formula:

[0151] In the formula: P—prevention and control effect, in percentage (%); CK—disease index of blank control; PT—disease index of drug treatment.

[0152] Representative test results are listed in Table 2.

[0153] Table 2. Representative bactericidal activity test results

[0154] Note: N represents no data; control compound A: Composition activity test:

[0155] Experimental diseases: cucumber powdery mildew, sunflower sclerotinia stem rot, cucumber downy mildew, rice blast, and cucumber anthracnose.

[0156] Dissolve each of the above active components or compositions in acetone (the volume ratio of acetone to spray volume is equal to or less than 0.05), dilute with water containing 0.1% Tween 80, and prepare a test solution of the required concentration. Separately prepare a test solution of the composition according to the set ratio. Using a crop sprayer, spray the test solution onto uniform host plants (not inoculated or treated with other drugs before application) grown in a greenhouse. Inoculate the plants with the disease 24 hours later. Based on the characteristics of the disease, inoculate diseased plants requiring temperature and humidity control and place them in a climate chamber for cultivation. After the disease has fully infected the plants, transfer them to a greenhouse for further cultivation. After the control group has fully developed the disease, conduct a disease survey and record the total number of leaves, the number of diseased leaves, and the disease severity.

[0157] Disease classification method:

[0158] Grade 0: The entire plant is disease-free;

[0159] Grade 1: Lesions cover less than 5% of the total leaf area;

[0160] Grade 3: Lesions cover 6-10% of the entire leaf area;

[0161] Grade 5: Lesions cover 11-20% of the entire leaf area;

[0162] Grade 7: Lesions cover 21-50% of the entire leaf area;

[0163] Level 9: The lesion area covers more than 50% of the entire leaf area.

[0164] The observed efficacy (C) of the active ingredient or composition obs The following formulas are commonly used for pesticide efficacy evaluation (corrected control efficacy calculation formula): Disease index = ∑(number of diseased leaves at each level × relative level value) / (total number of surveys × 9) × 100 Observation efficacy (%) = (control disease index - treatment disease index) / control disease index × 100

[0165] An efficacy of "0" indicates that the infection level of the treated crop is the same as that of the untreated control crop; an efficacy of "100" indicates that the treated crop is not infected.

[0166] The intended potency of the composition (C) expThe effect was determined using the Abbott method (see Liu Xuemin et al., Synergistic Effect of Mixed Fungicides, Pesticide Science and Management, 2002, 23(5), 12-15). exp =X + Y – XY / 100

[0167] In the formula, X: the efficacy of active component A at a concentration of a;

[0168] Y: The efficacy of active component B at a concentration of b.

[0169] The synergistic effect of the composition was observed using efficacy (C). obs ) and expected effectiveness (C exp The ratio (synergistic ratio) is used for evaluation. When the ratio (synergistic ratio) > 1, the composition exhibits a synergistic effect; when the ratio (synergistic ratio) = 1, the composition exhibits an additive effect; when the ratio (synergistic ratio) < 1, the composition exhibits an antagonistic effect.

[0170] Table 3. Evaluation of the synergistic effect of the composition on cucumber powdery mildew.

[0171] Table 4. Evaluation of the synergistic effect of the composition on sunflower sclerotinia stem rot.

[0172] Table 5. Evaluation of the synergistic effect of the composition on cucumber downy mildew.

[0173] Table 6. Evaluation of the synergistic effect of the composition on rice blast disease.

[0174] Table 7. Evaluation of the synergistic effect of the composition on cucumber anthracnose.

[0175] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit good control activity against various fungi, including those belonging to the Ascomycetes, Basidiomycetes, Deuteromycetes, and Oomycetes, and thus possess certain commercial value.

Claims

1. A pyrimidine-containing substituted pyrazole compound, as shown in general formula I: in, Q represents aryl or heterocyclic group; Y1 and Y2 independently represent hydrogen, alkyl, cycloalkyl, aryl, and -OR, respectively. 10 ,-alkylene-OR 10 -(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom form a heterocyclic group with N at the 1-position; R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or substituted -CH=CH-CH=CH-; R3 represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10 OR-alkylene- 10 ; R4, R5, R6, and R7 independently represent hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, or haloynyl, respectively. R8 and R9 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ; The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each of these groups independently represents hydrogen, alkyl, haloalkyl, phenyl, or a phenyl group substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

2. The pyrimidine-containing substituted pyrazole compound according to claim 1, characterized in that, Y1 and Y2 independently represent hydrogen, C1-C8 alkyl, C3-C8 cycloalkyl, aryl, and -OR, respectively. 10 -(C1-C8 alkylene)-OR 10 -(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom can form a 5-8 membered heterocyclic group with N at the 1-position; R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or halogenated -CH=CH-CH=CH-; R3 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10 OR -(C1-C8 alkylene)-OR 10 ; R4, R5, R6, and R7 independently represent hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 alkynyl, or halo-C2-C8 alkynyl, respectively. R8 and R9 independently represent hydrogen, 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, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ; The aforementioned C3-C8 cycloalkyl, heterocyclic, or aryl groups are optionally 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, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, phenyl, or a phenyl group 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. The pyrimidine-containing substituted pyrazole compound according to claim 1 or 2, characterized in that, Y1 and Y2 independently represent hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, aryl, and -OR, respectively. 10 -(C1-C6 alkylene)-OR 10 -(CO)R 10 or-(CO)OR 10 Alternatively, Y1 and Y2 together with the attached N atom form a 5-6 membered heterocyclic group with an N atom at the 1-position (e.g., unsubstituted or substituted by at least one group selected from halogens, alkyl groups, or haloalkyl groups). )； R1 and R2 independently represent hydrogen, halogen, nitro, amino, carboxyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, and -OR, respectively. 10 or -SR 10 Or R1 and R2 are connected together to form unsubstituted or halogenated -CH=CH-CH=CH-; R3 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl, C1-C6 alkyl, acyl chloride, and -(CO)OR. 10 -(CO)N(R) 10 )2、-OR 10 OR -(C1-C6 alkylene)-OR 10 ; R4, R5, R6, and R7 independently represent hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, or halo-C2-C6 alkynyl, respectively. R8 and R9 independently represent hydrogen, 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, aryl, heterocyclic, and -OR, respectively. 10 -SR 10 or-(CO)OR 10 ; The aforementioned C3-C6 cycloalkyl, heterocyclic, or aryl groups are optionally 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, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each of these groups independently represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, phenyl, or a phenyl group 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 a pyrimidine-containing substituted pyrazole compound as described in any one of claims 1-3, comprising the following steps: (1) The compound of general formula II is reacted with the compound of general formula III or its salt to prepare the compound of general formula I. The reaction equation is as follows: (2) Alternatively, when Y1 and Y2 are not both H, then... The intermediate undergoes a substitution reaction to yield compound I; Optionally, (3) the compound represented by general formula V is prepared by reacting the compound represented by general formula VI with the compound represented by general formula VII or a salt thereof (such as hydrochloride), and the reaction equation is as follows: Wherein, Hal and Hal' independently represent halogens, and the definitions of substituents Q, R1, R2, R3, R4, R5, R6, R7, R8, R9, Y1, and Y2 are as described in any one of claims 1-3; Preferably, the reactions in steps (1) and (3) are carried out in the presence of a solvent and a base; more preferably, the solvent is selected from at least one of toluene, DMF, DME, DMA, methanol, ethanol, diethyl ether, dichloroethane, DMSO, dioxane, tetrahydrofuran, dichloromethane or ethyl acetate, and the base is selected from at least one of inorganic base or organic base.

5. A fungicidal composition comprising a pyrimidine-containing substituted pyrazole compound (active ingredient A) as described in any one of claims 1-3; preferably, further comprising other active ingredient B; more preferably, said other active ingredient B is selected from at least one of the following: ethirimol, benzoyl permethrin, ... Fluopyram, fluopyram, prothioconazole, difenoconazole, tebuconazole, fluopyram, propiconazole, hexaconazole, chlorfluazuron, cyproconazole, tebuconazole, triadimefon, fenpyroximate, isopyram, chlorpyrifos, prochloraz Trifluopyridine, Fluopyram, Azoxystrobin, Pyraclostrobin, Cyazofamid, Azoxystrobin, Oxystrobin, Iprodione, Iprodione, Fludioxonil, Fluazinam, Fluazinam, Pyraclostrobin, Iprodione, Pyrimethanil, Azoxystrobin Cyazofamid, Cymoxanil, Fluopyram, Fluopyram, Fluopyram, Mancozeb, Zineb, Thiopyram, Cymoxanil Hydrochloride, Metalaxyl, Dimethomorph, Fluopyram, Dimethomorph Acetylpyridaben, Metalaxyl, Oxadiazon, Azoxystrobin, Chlorothalonil, Captan, Mancozeb, Propineb, Mancozeb, Thiram, Oxyphenidyl, Polyoxin, Kasugamycin, Kasugamycin, Ningnanmycin, Aminooligosaccharin, Chitosan, Aluminum Trisphosphonate, Copper Quinoline, Bordeaux mixture, Copper Succinate, Copper Calcium Sulfate, Tricyclazole, Isoprothiolane, Isoprothiolane, Isoprothiolane, Trimethoprim, Allylfenoxam Carbendazim, Thiophanate-methyl, More preferably, the weight ratio of active ingredient A to B is 1:2000-100:1, 1:1600-50:1, 1:1200-20:1, 1:800-10:1, 1:400-1:1, 1:320-1:2, 1:200-1:2.5, 1:160-1:4, 1:100-1:5, 1:80-1:8, 1:40-1:10, or 1:32-1:

20.

6. Use of the pyrimidine-containing substituted pyrazole 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.

7. A method for controlling harmful fungi, comprising treating fungi or materials, plants, soil or seeds to be protected against fungal invasion with an effective amount of a pyrimidine-containing substituted pyrazole compound as described in any one of claims 1-3, or a composition as described in claim 5.

8. An intermediate as described in formula II, III or V of claim 4.

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