Phenyl-substituted tetrazolinone compound and use thereof

Abstract

The present invention pertains to the technical field of pesticides, and relates in particular to a phenyl-substituted tetrazolinone compound and a use thereof. The compound is represented by Formula I: where Q represents a heterocyclic group; X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 each independently represent hydrogen, halogen, alkyl, alkenyl, or the like; and R represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, or the like. The compound has excellent fungicidal activity.

Description

A phenyl-substituted tetrazolinone compound and its application Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a phenyl-substituted tetrazolinone compound and its applications. 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 WO2013162072A1 which discloses tetrazolinone compounds and their applications as fungicides, 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 phenyl-substituted tetrazolinone compound and its applications. The compound exhibits excellent bactericidal activity.

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

[0005] A phenyl-substituted tetrazolinone compound as shown in Formula I:

[0006] Where Q represents a heterocyclic group;

[0007] X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, nitro, cyano, cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11 , -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, trialkylsilyl, cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11 At least one substituent is an alkyl, alkenyl, or alkynyl group;

[0008] R represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl;

[0009] n represents 0, 1, or 2;

[0010] The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced;

[0011] R 11 Each of the following can independently represent hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl, or alkynyl groups substituted with at least one group selected from halogen, hydroxyl, alkoxy, cycloalkyl, cycloalkenyl, cyano, or alkoxycarbonyl: alkyl, alkenyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

[0012] In one specific embodiment, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, nitro, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11 , -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, triC1-C8 alkylsilyl, C3-C8 cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11The C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group is substituted with at least one substituent.

[0013] R represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkylthio-C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl.

[0014] n represents 0, 1, or 2;

[0015] 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, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced;

[0016] R 11 Each of the following can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, cyano, or C1-C8 alkoxycarbonyl: substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, or 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.

[0017] In another specific embodiment, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, nitro, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11, -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11 The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is substituted with at least one substituent.

[0018] R represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl.

[0019] n represents 0, 1, or 2;

[0020] 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 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced;

[0021] R 11Each of the following independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, cyano, or C1-C6 alkoxycarbonyl, and is a phenyl group substituted with at least one of the following groups: halogen, hydroxyl, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, phenyl, or is substituted with at least one of the following groups: 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.

[0022] 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, in the compound term "cycloalkylalkyl," the alkyl 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, 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. 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, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0023] 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

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] Another embodiment of this application is a method for preparing the phenyl-substituted tetrazolinone compound, comprising the following steps:

[0030] (1) Compound II reacts with Compound III to prepare Compound I. The chemical reaction equation is as follows:

[0031] Or (2) Compound I is prepared by coupling reaction of compound IV and compound V, and the chemical reaction equation is as follows:

[0032] Where Hal and Z represent halogens; P represents... The definitions of substituents Q, R, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 are as described above.

[0033] In one specific embodiment, the reaction (1) is carried out in the presence of a solvent.

[0034] In one specific embodiment, the reaction (2) is carried out in the presence of a solvent and a base.

[0035] In another specific embodiment, a base is added during the reaction (1).

[0036] In another specific embodiment, a catalyst is added during the reaction (2).

[0037] In one specific embodiment, the solvent for the reaction (1) is selected from at least one of N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, 1,4-dioxane, tetrahydrofuran, or ethyl acetate.

[0038] In one specific embodiment, the solvent for reaction (2) is an organic solvent / water, wherein the organic solvent is selected from at least one of N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, 1,4-dioxane, tetrahydrofuran or ethyl acetate.

[0039] In one specific embodiment, the base in reactions (1) and (2) is selected from at least one of inorganic or organic bases, such as NaH, KH, K2CO3, Na2CO3, Cs2CO3, NaHCO3, K3PO4, NaOH, KOH, KOAc, NaOAc, t-BuOK, EtONa, NaOMe, triethylamine, pyridine, etc.

[0040] In one specific embodiment, the catalyst for the reaction is selected from [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride [PdCl2(dppf)], [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride dichloromethane complex [Pd(dppf)Cl] 2· At least one of [CH2Cl2], palladium acetate [Pd(OAc)2], palladium dichloride of bis(triphenylphosphine) [(PPh3)2PdCl2] or tetra(triphenylphosphine)palladium [Pd(PPh3)4].

[0041] Another embodiment of this application is a bactericidal composition comprising a biologically effective amount of a compound of formula I.

[0042] In one specific embodiment, it also includes a formulation adjuvant.

[0043] In another specific embodiment, other active ingredients are also included.

[0044] Another embodiment of this application is the use of the compound of Formula I or the above-described fungicidal composition in the control of plant pathogenic fungi. This use includes protecting plants from plant pathogenic microorganisms or treating plants infected by plant pathogenic microorganisms, wherein the use comprises applying the compound of Formula I or a composition containing said compound to soil, plants, parts of plants, leaves, and / or roots.

[0045] The compounds of this application can be applied as compounds or as formulations containing said compounds using any of the various known techniques. For example, said compounds can be applied to the roots or leaves of plants to control various fungi without compromising the commercial value of the plants. The substances can be applied in any commonly used formulation type, such as as solutions, powders, wetting powders, flowable concentrates, or emulsifiable concentrates.

[0046] Preferably, the compounds of this application are applied in formulation form, said formulation comprising one or more compounds of Formula I and a botanically acceptable carrier. The concentrated formulation may be dispersed in water or other liquids for application, or the formulation may be a dust or granules that can be applied immediately without further processing. The formulation may be prepared according to methods commonly used in the field of agricultural chemistry.

[0047] This application contemplates the use of all media through which the one or more compounds can be formulated for delivery and use as fungicides. Typically, the formulation is applied as an aqueous suspension or emulsion. The suspension or emulsion can be prepared from water-soluble, water-suspendable, or emulsifiable formulations, which are generally referred to as wettable powders when the water-soluble, water-suspendable, or emulsifiable formulation is a solid; or as emulsifiable oils, aqueous suspensions, or suspension concentrates when the water-soluble, water-suspendable, or emulsifiable formulation is a liquid. It is readily understood that any substance capable of incorporating these compounds can be used, provided that the desired use is achieved without significantly impairing the activity of these compounds as antifungal agents.

[0048] Wettable powders that can be pressed into water-dispersible particles comprise a homogeneous mixture (intimate mixture) of one or more compounds of Formula I, an inert carrier, and a surfactant. The concentration of the compound in the wettable powder, by weight of the total wettable powder, can range from about 10 wt% to about 90 wt%, more preferably from about 25 wt% to about 75 wt%. In the preparation of the wettable powder formulation, the compound can be mixed with any finely pulverized solid, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite, diatomaceous earth, refined silicates, etc. In this operation, the finely pulverized carrier and surfactant are typically blended with and ground with the compound.

[0049] The emulsifiable concentrate of Formula I can be contained in a suitable liquid at a conventional concentration, for example, from about 1 wt% to about 50 wt%, based on the total weight of the emulsifiable concentrate. The compound can be dissolved in an inert support, which is a mixture of a water-miscible solvent or a water-immiscible organic solvent and an emulsifier. The emulsifiable concentrate can be diluted with water and oil to form a spray mixture in the form of an oil-in-water emulsion. Useful organic solvents include the aromatic fractions of petroleum, particularly the high-boiling cycloalkane and alkene fractions, such as heavy aromatic naphtha. Other organic solvents may also be used, such as terpene solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.

[0050] The emulsifiers that can be advantageously used in this application can be readily determined by those skilled in the art and include a variety of nonionic emulsifiers, anionic emulsifiers, cationic emulsifiers, and amphoteric emulsifiers, or blends of two or more emulsifiers. Examples of nonionic emulsifiers used to prepare the emulsifiable concentrates include polyalkylene glycol ethers, and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines, or fatty acids with ethylene oxide or propylene oxide, such as ethoxylated alkylphenols and carboxylic acid esters dissolved in polyols or polyoxyethylenes. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include oil-soluble salts of alkyl aryl sulfonic acids (e.g., calcium salts), oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphorylated polyglycol ethers.

[0051] Representative organic liquids that can be used in the preparation of the emulsifiable concentrates of the compounds of this application are aromatic liquids such as xylene and propylbenzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkylamides of various fatty acids, especially dimethylamides and diol derivatives of fatty glycols such as n-butyl ether, ethyl ether or methyl ether of diethylene glycol, methyl ether of triethylene glycol, petroleum fractions or hydrocarbons such as mineral oils, aromatic solvents, paraffin oils, etc.; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil, etc.; esters of the above vegetable oils; etc. Mixtures of two or more organic liquids can also be used in the preparation of the emulsifiable concentrate. Organic liquids include xylene and propylbenzene fractions, with xylene being the most preferred in some cases. Surfactant dispersants are typically used in liquid formulations, and the amount of the surfactant dispersant is from 0.1 to 20 wt% based on the total weight of the dispersant and one or more compounds. The formulation may also contain other compatible additives, such as plant growth regulators and other bioactive compounds used in agriculture.

[0052] Aqueous suspensions comprise suspensions of one or more water-insoluble compounds of formula I dispersed in an aqueous medium, with a concentration of about 1 wt% to about 50 wt% by weight of the total aqueous suspension. The suspension is prepared by finely grinding one or more of the compounds, and vigorously mixing the ground compounds into a medium composed of water and surfactants selected from the same type described above. Other components, such as inorganic salts and synthetic or natural gums, may also be added to increase the density and viscosity of the aqueous medium.

[0053] Compounds of Formula I can also be applied in granular form, particularly for application to soil. By total weight, the granular formulation typically contains about 0.5 wt% to about 10 wt% of the compound dispersed in an inert carrier, which is wholly or mostly composed of coarsely pulverized inert material, such as attapulgite, bentonite, diatomaceous earth, clay, or similar inexpensive materials. The formulation is typically prepared by dissolving the compound in a suitable solvent and applying it to a granular carrier pre-formed to a suitable particle size (ranging from about 0.5 to about 3 mm). The suitable solvent is one in which the compound is substantially or completely soluble. The formulation can also be prepared by forming the carrier, compound, and solvent into a paste or ointment, then crushing and drying to obtain the desired granular particles.

[0054] Powders containing compound I can be prepared by homogenizing one or more of the compounds in powder form with a suitable powdery agricultural carrier, such as kaolin clay, crushed volcanic rock, etc. The powder may suitably contain about 1% to about 10% of the compounds by weight.

[0055] The formulation may additionally contain co-active surfactants to enhance the deposition, wetting, and penetration of the compound onto target crops and microorganisms. These co-active surfactants may optionally be used as a component of the formulation or as a tank mixture. The amount of the co-active surfactant is typically from 0.01 to 1.0 vol% by water spray volume, preferably 0.05 to 0.5 vol%. Suitable co-active surfactants include, but are not limited to, ethoxylated nonylphenol, ethoxylated synthetic alcohols or ethoxylated natural alcohols, sulfosuccinates or sulfosuccinates, ethoxylated organosiloxanes, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrates (mineral oil (85%) + emulsifier (15%)); nonylphenol ethoxylates; benzyl cocoyl dimethyl quaternary ammonium salts; blends of petroleum hydrocarbons, alkyl esters, organic acids, and anionic surfactants; C9-C 11 Alkyl polyglycosides; phosphorylated alcohol ethoxylates; natural primary alcohols (C 12 -C 16 Ethoxylated compounds; di-sec-butylphenol EO-PO block copolymers; polysiloxane-methyl-terminated compounds; nonylphenol ethoxylated compounds + urea ammonium nitrate; emulsified methylated seed oils; tridecyl alcohol (synthetic) ethoxylated compounds (8EO); tallow amine ethoxylated compounds (15EO); PEG (400) dioleate-99. The formulations may also comprise oil-in-water emulsions, such as those disclosed in U.S. Patent Application Serial No. 11 / 495,228, the contents of which are incorporated herein by reference.

[0056] The formulation may optionally include a combination containing other pesticide compounds. These additional pesticide compounds may be fungicides, insecticides, herbicides, nematicides, acaricides, arthropodicides, fungicides, or combinations thereof, which are compatible with the compound of this application in the chosen application medium and do not antagonize the activity of the compound of this application. Therefore, in the described embodiments, the other pesticide compounds are used as supplementary toxins for the same or different pesticide uses. The Formula I compound and the pesticide compound may typically be present in combination in a weight ratio of 1:100 to 100:1.

[0057] The compounds of this application can also be combined with other fungicides to form fungicidal mixtures and synergistic mixtures thereof. The fungicidal compounds of this application are typically applied in combination with other fungicides to control a wider range of undesirable diseases. When applied in combination with other fungicides, the compounds claimed in this application can be formulated together with other fungicides, mixed with other fungicide containers, or applied sequentially with other fungicides. 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 octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide 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, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fl uxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, furaidazole, furaxyl, furamepyr, 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, mancozebMandipropamid, Maneb, Mefenoxam, Mepanipyrim, Mepronil, Meptyl-dinocap, Mercuric chloride, Mercuric oxide, Mercurous chloride, Metalaxyl, Metalaxyl-M, Metam, Metam-ammonium, Metam-potassium, Metam-sodium, Metconazole, Methasulfocarb, Methyl iodide, Methyl isothiocyanate isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofuronamide, oleic acid (fatty acid), orysastrobin, 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, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, piraclostrobin, piratostrobin, piraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenol 2-phenyl phenoxide), sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, wood tar oil), tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin,Triflumizole, Triforine, Triticonazole, Validamycin, Valifenalate, Valiphenal, Vinclozolin, Zineb, Ziram, Zoxamide, Candida oleophila, 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, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury)sulfate, bis(tributyltin)oxide, buthiobate, cadmium calcium copper zinc chromate Sulfate), Carbamorph, Cyanide Acetonide (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, Dibutyl nitrate Noterbon, Dipyrithione, Ditalimfos, Dodicin, Drazoxolon, EBP, ESBP, Etaconazole, Ethylhexidine, Ethirim, Fenaminosulfonate, Fenapanil, Fenitropan, FluotrimazoleFurcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, propiconazole (ICIA0858), isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric acid anhydride anhydride, myclozolin, N-3,5-dichlorophenylsuccinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), octachlorophenone (OCH), phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride Hydrochloride, Pyracarbolid, Pyridinitril, Pyroxychlor, Pyroxyfur, 5-acetyl-8-hydroxyquinoline; 5-acetyl-8-hydroxyquinoline sulfate, Quinazamid, Quinconazole, Rabenzazole, Salicylanilide, SSF-109 (azoxystrobin)Sulforubber, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trihlamide, urethane, zarilamid, and any combination thereof.

[0058] Furthermore, the compounds described in this application can be combined with other insecticides, including insecticides, nematicides, acaricides, arthropod icides, fungicides, or combinations thereof, wherein the other insecticides are compatible with the compounds of this application in the chosen application medium and do not antagonize the activity of the compounds of this application to form insecticidal mixtures and synergistic mixtures thereof. The fungicidal compounds of this application can be applied in combination with one or more other insecticides to control a wider range of undesirable pests. When applied in combination with other insecticides, the compounds claimed in this application can be formulated together with other insecticides, mixed with other insecticide canisters, or applied sequentially with other insecticides.

[0059] Furthermore, the compounds described in this application can be combined with herbicides that are compatible with and do not antagonize the activity of the compounds in the chosen application medium to form insecticidal mixtures and synergistic mixtures thereof. The fungicidal compounds of this application are typically applied in combination with one or more herbicides to control a wider range of undesirable plants. When applied in combination with a herbicide, the claimed compounds can be formulated together with the herbicide, mixed with a herbicide container, or applied sequentially with the herbicide.

[0060] Another embodiment of this application is a method for preventing and controlling harmful fungi. It involves treating fungi, or materials, plants, soil, or seeds to be protected from fungal invasion, with a compound of Formula I or the above-described fungicidal composition.

[0061] The compounds have been found to have significant antifungal activity, particularly for agricultural applications. Many of these compounds are especially effective for agricultural crops and horticultural plants.

[0062] Those skilled in the art will understand that the efficacy of the compound against the aforementioned fungi establishes the compound's general utility as a fungicide.

[0063] The compound exhibits broad-spectrum activity against fungal pathogens. Exemplary pathogens may include, but are not limited to, the following disease initiators: wheat leaf blotch (Zymoseptoria tritici), wheat brown rust (Puccinia triticina), wheat stripe rust (Puccinia striiformis), apple scab (Venturia inaequalis), grape powdery mildew (Uncinula necator), barley scald (Rhynchosporium secalis), rice blast (Pyricularia oryzae), and soybean rust. Soybean rust (Phakopsorapachyrhizi), wheat glume blotch (Leptosphaerianodorum), wheat powdery mildew (Blumeria graminis f.sp.tritici), barley powdery mildew (Blumeria graminis f.sp.hordei), cucurbit powdery mildew (Erysiphe cichoracearum), cucurbit anthracnose (Colletotrichum lagenarium), beet leaf spot (Cercospora beticola), tomato early blight. Tomato (Alternaria solani) and barley spot disease (Cochliobolus sativus)The exact amount of active ingredient applied depends not only on the specific active ingredient applied but also on the desired action, the species and growth stage of the fungus being controlled, and the plant part or other product that will come into contact with the compound. Therefore, all compounds and formulations containing the compound may not be equally effective or effective against the same species of fungus at similar concentrations.

[0064] The compound is applied to plants in a disease-inhibiting and botany-acceptable amount. The term "disease-inhibiting and botany-acceptable amount" refers to the amount of a compound that kills or inhibits plant diseases (to which control is desired) but is not obviously toxic to the plant. This amount is typically from about 0.1 to about 1000 ppm (parts per million), preferably 1 to 500 ppm. The exact concentration of the desired compound varies depending on the fungal disease being controlled, the type of formulation used, the method of application, the specific plant species, climatic conditions, etc. Suitable application rates are typically from about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g / m²). 2 Within the range of ).

[0065] It will be apparent to those skilled in the art that any range or desired value given herein can be extended or modified without losing the desired effect. Detailed Implementation

[0066] 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.

[0067] 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. Specific compound structures and corresponding compound information are shown in Tables 1-2. 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.

[0068] Table 1. Compound Structures

[0069] Table 2 Compounds 1 H NMR values

[0070] 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.

[0071] 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.

[0072] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0073] 1. Synthesis of Compound 1

[0074] Compound 1-1 (400 mg, 1 mmol) was dissolved in DMF, and NaH (200 mg, 5 eq) was added at room temperature. After half an hour, compound 1-2 (920 mg, 5 eq) was added, and the reaction was carried out overnight at room temperature. The reaction was completed under LCMS control. EA and water were added to the system for extraction. The aqueous phase was extracted twice with EA. The organic phases were combined and washed three times with a large amount of brine. The organic phase was dried and concentrated, and then purified in normal phase to obtain colorless oil product 1 (200 mg, yield 44%).

[0075] 2. Synthesis of Compound 5

[0076] Compound 1-1 (600 mg, 1.54 mmol) was weighed and dissolved in DMF. Then, compound NaH (184.8 mg, 4.62 mmol) was added under ice bath conditions, and the mixture was allowed to react at room temperature for half an hour. Then, compound 5-1 (914.8 mg, 4.62 mmol) was added under ice bath conditions, and the mixture was allowed to react at room temperature for 2 hours. The reaction was monitored by LCMS until complete. The system was poured into water, extracted with ethyl acetate, and the organic phase was washed 4-5 times with saturated brine. The organic phase was concentrated and purified under normal phase to give compound 5 (white oil, 350 mg, yield 49.5%).

[0077] 3. Synthesis of Compound 56

[0078] Compound 1 (100 mg, 0.22 mmol) was dissolved in 5 mL of N,N-dimethylformamide, and N-chlorosuccinimide (3 eq) was added. The reaction was carried out overnight at 50 °C. The reaction was completed under LCMS control. Ethyl acetate and water were added to the system for extraction. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 56 (80 mg, 93%) was purified by mixing with normal phase.

[0079] 4. Synthesis of Compound 75

[0080] (1) Compound 75-1 (2 g, 8.8 mmol) was dissolved in 20 mL of N,N-dimethylformamide, sodium hydrogen (3 eq) and 3-iodooxetane (2 eq) were added, and the reaction was carried out overnight at room temperature. The reaction was completed under LCMS control. Ethyl acetate and water were added to the system for extraction. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 75-2 (2.1 g, 84%) was obtained by normal phase purification.

[0081] (2) Compound 75-2 (2.1 g, 7.4 mmol) was dissolved in 20 mL of dry tetrahydrofuran under nitrogen protection. 1.1 eq of n-butyllithium was added dropwise at -78 °C. After half an hour, 1.1 eq of dimethyl disulfide was added dropwise. The reaction was allowed to proceed overnight at room temperature. The reaction was completed under LCMS control. Ethyl acetate and water were added to the system for extraction. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 75-3 (1.1 g, 59%) was obtained by normal-phase purification.

[0082] (3) Compound 75-3 (1.1 g, 4.4 mmol) was dissolved in dichloromethane, and m-chloroperoxybenzoic acid (3 eq) was added. The reaction was carried out overnight at room temperature. The reaction was completed under LCMS control. Dichloromethane and water were added to the system for extraction. The aqueous phase was extracted twice with dichloromethane. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 75-4 (200 mg, 59%) was obtained by normal phase purification.

[0083] (4) Compound 75-4 (200 mg, 0.7 mmol) was dissolved in a mixed solvent of 5 mL dioxane and 2 mL water. 75-5 (1 eq), potassium carbonate (3 eq), and 1,1'-bis(diphenylphosphine)ferrocene palladium chloride (0.02 eq) were added. The mixture was evacuated and reacted overnight at 100 °C. The reaction was completed under LCMS control. Ethyl acetate and water were added to the system for extraction. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 75 (50 mg, 13%) was purified by mixing with normal phase.

[0084] 5. Synthesis of Compound 81

[0085] Compound 63 (synthetic reference 75, 150 mg, 0.3 mmol) was dissolved in a mixed solvent of 5 mL toluene and 1 mL water. Cyclopropylboronic acid (1 eq), potassium phosphate (3 eq), palladium acetate (0.1 eq), and tricyclohexylphosphine (0.1 eq) were added. The reaction was carried out overnight at 100 °C under nitrogen protection. The reaction was completed under LCMS control. Ethyl acetate and water were added to the system for extraction. The aqueous phase was extracted twice with ethyl acetate. The organic phases were combined and washed three times with brine. The organic phase was dried and concentrated. The product 81 (70 mg, 36%) was purified by mixing with normal phase.

[0086] Bioactivity evaluation (bactericidal activity test - pot method):

[0087] The agent was dissolved in dimethyl sulfoxide and diluted with 0.1% Tween 80 aqueous solution to different concentrations. Each concentration treatment was repeated three times. The experiment included a solvent control without the agent and a water treatment as blank controls. The solution was sprayed evenly onto the leaf surface until completely wetted, and then allowed to air dry before use.

[0088] Asian rust of soybean and blast of rice: The experimental targets were Phakopsora pachyrhizi Syd. and Magnaphorthe oryza, both cultured in live pots. Spores were collected from the surface of soybean and rice leaves using a 0.1% Tween 80 aqueous solution and prepared into suspensions (concentration 4 x 10⁻⁶ spores per ml). 5 1 x 10 6 (1 spore), store at 4℃ for later use. Spray the fresh spore suspension onto the leaf surface. For the protective test, inoculate 24 hours after treatment. After inoculation, place in dark conditions with relative humidity above 90% and temperature around 25℃ for disease development. After 24 hours, alternate between light and dark for 12 hours each.

[0089] Cucumber powdery mildew: The experimental target was selected from cucurbit monothecia [Sphaerotheca cucurbitae (Jacz.) ZYZhao] cultured on live potted plants or detached leaves. Diseased and spore-producing cucumber leaves were removed, and after shaking off the excess powder, the leaves were gently tapped with a glass rod to evenly distribute the cucumber powdery mildew spores onto the test material. Protective experiments were conducted 24 hours after treatment with the fungicide. After inoculation, the plants were placed at approximately 25°C and cultured under alternating light and dark conditions for 12 hours each.

[0090] Based on the disease incidence in the blank control group (disease level 9), the inoculated leaves were graded. The following grading method was used:

[0091] Level 0: No disease;

[0092] Grade 1: The area of ​​lesions accounts for less than 5% of the total leaf area;

[0093] Grade 3: The lesion area accounts for 6% to 10% of the total leaf area;

[0094] Level 5: The lesion area accounts for 11% to 25% of the total leaf area;

[0095] Level 7: The lesion area accounts for 26% to 50% of the total leaf area;

[0096] Level 9: The lesion area accounts for more than 50% of the total leaf area.

[0097] Based on the survey data, the disease index and prevention and control effects of each treatment were calculated.

[0098] The disease index is calculated according to formula (1), and the result is rounded to two decimal places: X={(∑(Ni xi)) / (N x 9)}x 100………………………………………(1)

[0099] In the formula: X—disease index; Ni—number of diseased leaves at each level; i—relative level value; N—total number of leaves surveyed.

[0100] The control effect is calculated according to formula (2): P={(CK-PT) / CK}x 100………………………………………(2)

[0101] In the formula: P—prevention and control effect, in percentage (%); CK—disease index of blank control; PT—disease index of drug treatment.

[0102] Table 3. Results of control using representative compounds Note: N represents no data; control compound A: Reference compound B:

[0103] Furthermore, numerous tests have revealed that the compounds and 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 phenyl-substituted tetrazolinone compound as shown in Formula I: in, Q represents a heterocyclic group; X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, nitro, cyano, cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11 , -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, trialkylsilyl, cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11 At least one substituent is an alkyl, alkenyl, or alkynyl group; R represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl or heterocyclic alkyl; n represents 0, 1, or 2; The aforementioned cycloalkyl, heterocyclic, or aryl groups are optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced; R 11 Each of the following can independently represent hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl, or alkynyl groups substituted with at least one group selected from halogen, hydroxyl, alkoxy, cycloalkyl, cycloalkenyl, cyano, or alkoxycarbonyl: alkyl, alkenyl, phenyl, or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy.

2. The phenyl-substituted tetrazolinone compound according to claim 1, characterized in that, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, nitro, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11 , -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, triC1-C8 alkylsilyl, C3-C8 cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11 The C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl group substituted with at least one substituent; R represents hydrogen, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, C1-C8 alkoxy-C1-C8 alkyl, C1-C8 alkylthio-C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl. n represents 0, 1, or 2; 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, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced; R 11 Each of the following can independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, cyano, or C1-C8 alkoxycarbonyl: substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, phenyl, or 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 phenyl-substituted tetrazolinone compound according to claim 1 or 2, characterized in that, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, nitro, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 11 , -O(CO)R 11 , -(CO)R 11 -(CO)OR 11 , -S(O) n R 11 , -N(R 11 )2, or selected from cyano, halogen, triC1-C6 alkylsilyl, C3-C6 cycloalkyl, heterocyclic, aryl, -O(CO)R 11 -N(R) 11 )2、-OR 11 -(CO)R 11 -S(O) n R 11 or-(CO)OR 11 The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is substituted with at least one substituent. R represents hydrogen, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkylthio-C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl. n represents 0, 1, or 2; 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 alkynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 alkynyl, -OR 11 -SR 11 -(CO)R 11 -(CO)OR 11 -N(R) 11 )2、-(CO)N(R 11 )2、-(CS)N(R 11 )2、-(SO)R 11 or -(SO2)R 11 At least one group in it is replaced; R 11 Each of the following can independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, cyano or C1-C6 alkoxycarbonyl, phenyl, or phenyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, phenyl, or 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 phenyl-substituted tetrazolinone compound according to any one of claims 1-3, comprising the following steps: (1) Compound II reacts with Compound III to prepare Compound I. The chemical reaction equation is as follows: Or (2) Compound I is prepared by coupling reaction of compound IV and compound V, and the chemical reaction equation is as follows: in, Hal and Z represent halogens; P represents The definitions of substituents Q, R, X1, X2, X3, X4, R1, R2, R3, R4, R5, and R6 are as described in any one of claims 1-3; Preferably, reaction (1) is carried out in the presence of a solvent, and reaction (2) is carried out in the presence of a solvent and a base; more preferably, a base is added during reaction (1), and a catalyst is added during reaction (2); even more preferably, the solvent for reaction (1) is selected from at least one of N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, 1,4-dioxane, tetrahydrofuran, or ethyl acetate, and the solvent for reaction (2) is an organic solvent / water, wherein the organic solvent is selected from N, At least one of N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, 1,4-dioxane, tetrahydrofuran, or ethyl acetate, wherein the base in reactions (1) and (2) is selected from at least one of inorganic or organic bases, and / or the catalyst for the reaction is selected from at least one of [1,1'-bis(diphenylphosphine)ferrocene]palladium(II) dichloride, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride dichloromethane complex, palladium acetate, bis(triphenylphosphine)palladium dichloride, or tetra(triphenylphosphine)palladium.

5. A bactericidal composition, characterized in that, It contains at least one of the phenyl-substituted tetrazolinone compounds according to any one of claims 1-3 in a biologically effective amount; preferably, it further includes a formulation adjuvant; more preferably, it further includes other active ingredients.

6. Use of the phenyl-substituted tetrazolinone compound as described in any one of claims 1-3 or the fungicidal 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 phenyl-substituted tetrazolinone compound as described in any one of claims 1-3 or a fungicidal composition as described in claim 5.

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