Phenylamidine compound and use thereof

Abstract

The present invention relates to the technical field of pesticides, and specifically to a phenylamidine compound and a use thereof. The compound is as shown in formula I, in which X represents O, S or CH2; M represents C-R5 or N; Q represents N(Y)2 or a N-1 heterocyclic group; Y independently represents hydrogen, alkyl, haloalkyl or the like; R1 and R2 each independently represent hydrogen, cyano, halogen, alkyl or the like; R3, R4, and R5 each independently represent hydrogen, halogen, cyano, nitryl or the like; and R6 represents halogen, OR, S(O)nR or the like. The compound has excellent fungicidal and bactericidal effects.

Description

Phenyl amidine compounds and use thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a phenyl amidine compound and use thereof. BACKGROUND

[0002] In recent years, due to the long-term use of pest control agents such as insecticides or fungicides, pests have become resistant and difficult to control by the existing use of insecticides or fungicides. In addition, some of the known pest control agents are highly toxic, or some destroy the ecological system through their long-term residual properties. In this case, although a large number of fungicides are known, such as WO2016039459A1 discloses phenyl amidine compounds and their use as fungicides, there is still a need to develop new pest control agents with low toxicity and low residual properties. SUMMARY

[0003] To solve the above problems existing in the prior art, the present application provides a phenyl amidine compound and use thereof. The compound has excellent fungicidal effect.

[0004] The technical scheme adopted by the present application is as follows:

[0005] A phenyl amidine compound or salt thereof, as shown in general formula I:

[0006] X represents O, S or CH2;

[0007] M represents C-R5 or N;

[0008] Q represents N(Y)2 or a heterocyclic group at position 1;

[0009] Y independently represents hydrogen, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclic group, heterocyclic group alkyl or -OR7;

[0010] R1, R2 independently represent hydrogen, cyano, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -OR7 or -S(O) m R7;

[0011] R3, R4, R5 independently represent hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, -N(R7)2, -OR7 or -S(O) m R7; wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted with at least one group selected from halogen or -OR7;

[0012] R6 represents halogen, OR, S(O)n R or OS(O)2R;

[0013] R7each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl;

[0014] m represents 0, 1 or 2;

[0015] n represents 0, 1 or 2;

[0016] R each independently represents hydrogen, alkyl or haloalkyl;

[0017] the aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2 or -O-alkylene-(CO)OR 10 ;

[0018] R 10 each independently represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl.

[0019] In one embodiment, Q represents N(Y)2or a 5- or 6-membered heterocyclyl group at position 1 N;

[0020] Y each independently represents hydrogen, cyano, C1-C8alkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, aryl, arylC1-C8alkyl, heterocyclyl, heterocyclylC1-C8alkyl or -OR7;

[0021] R1, R2each independently represents hydrogen, cyano, halogen, C1-C8alkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl, haloC2-C8alkynyl, -OR7or -S(O) m R7;

[0022] R3, R4, R5each independently represents hydrogen, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, -N(R7)2, -OR7or -S(O) mR7; wherein said "C1-C8alkyl", "C2-C8alkenyl" or "C2-C8alkynyl" is optionally substituted with at least one group selected from halogen or -OR7;

[0023] R7independently of one another represent hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C1-C8haloalkyl, C2-C8haloalkenyl, C2-C8haloalkynyl, C3-C8cycloalkyl, C3-C8cycloalkenyl, aryl or heterocyclyl;

[0024] m represents 0, 1 or 2;

[0025] R independently of one another represent hydrogen, C1-C8alkyl or haloC1-C8alkyl;

[0026] The aforementioned "C3-C8cycloalkyl", "C3-C8cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, haloC3-C8cycloalkyl, C3-C8cycloalkyl substituted with C1-C8alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2or -O-(C1-C8alkylene)-(CO)OR 10 ;

[0027] R 10 independently of one another represent hydrogen, C1-C8alkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl or haloC2-C8alkynyl.

[0028] In another embodiment, Q represents N(Y)2,

[0029] Y independently of one another represent hydrogen, cyano, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, aryl, arylC1-C6alkyl, heterocyclyl, heterocyclylC1-C6alkyl or -OR7;

[0030] R1, R2each independently represents hydrogen, cyano, halogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR7or -S(O)mR7; m R7;

[0031] R3, R4, R5each independently represents hydrogen, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, -N(R7)2, -OR7or -S(O)mR7; m R7; wherein said "C1-C6alkyl", "C2-C6alkenyl" or "C2-C6alkynyl" is optionally substituted with at least one group selected from halogen or -OR7;

[0032] R7each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, aryl or heterocyclyl;

[0033] m represents 0, 1 or 2;

[0034] R each independently represents hydrogen, C1-C6alkyl or haloC1-C6alkyl;

[0035] The aforementioned "C3-C6cycloalkyl", "C3-C6cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, haloC3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, -OR7, -SR7, -N(R7)2, -C(O)R7, -C(O)OR7, -C(O)N(R7)2, -S(O)mR7, -S(O)mOR7, -S(O)mN(R7)2, -N(R7)C(O)R7, -N(R7)C(O)OR7, -N(R7)C(O)N(R7)2, -N(R7)S(O)mR7or -O-(C1-C6alkylene)-(CO)OR7; 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2or -O-(C1-C6alkylene)-(CO)OR 10 ;

[0036] R 10 each independently represents hydrogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl or haloC2-C6alkynyl.

[0037] In the definition of the compounds of the general formulae above and in all the formulae below, the professional terms used, whether used alone or in a compound word, stand for the following substituents: Alkyl groups having more than two carbon atoms can be straight-chain or branched. As in the compound word "O-alkylene-(CO)OR 10 " the alkylene can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. Alkyl groups are, for example, C1 alkyl - methyl; C2 alkyl - ethyl; C3 alkyl - propyl, such as n-propyl or isopropyl; C4 alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5 alkyl - pentyl, such as n-pentyl; C6 alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, 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 is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bonds can be in any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bonds can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0038] Unless specifically stated otherwise, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0039] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and that the description includes instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is either unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood as meaning that the group is substituted with one or more, identical or different, groups selected from those mentioned. In addition, the same or different substituents contained in the same or different substituent groups are each selected independently of the others, either identically or differently. The same applies to ring systems formed from different atoms and elements. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0040] In addition, unless specifically limited otherwise, the term "substituted with at least one group" as used herein means substituted with, for example, 1, 2, 3, 4, or 5 groups; groups not labeled with a specific position of attachment (including heterocyclyl, aryl, etc.) can be attached at any position, including attachment to a C or N; if substituted, substituents can also be substituted at any position, as long as the rules of valency are followed. For example, a heteroaryl group substituted with 1 methyl group may represent etc.

[0041] The compounds of formula I, in each case in free form or in salt form, and where appropriate the tautomers thereof, can exist in one of the possible isomers or as a mixture of these, for example in the form of pure isomers, such as antipodes and / or diastereomers, or as isomer mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemate mixtures, depending on the number of asymmetric carbon atoms present in the molecule, the absolute and relative configuration, and / or depending on the configuration of non-aromatic double bonds present in the molecule; the application relates to these pure isomers and also to all possible isomer mixtures and should be interpreted in each case in this sense, even if stereochemical details are not mentioned in each case. The application thus encompasses all such isomers and tautomers and mixtures thereof in all proportions, together with isotopic forms, for example deuterated compounds.

[0042] In another embodiment, formula I is also understood to include their salts or hydrates. Exemplary salts include, but are not limited to: hydrochlorides, hydrobromides, and hydroiodides.

[0043] It will also be understood by the person skilled in the art that, unless otherwise indicated, additional substitution is permitted, provided that the rules of chemical bonding and strain energy are satisfied and the product still exhibits fungicidal activity.

[0044] Another embodiment of the present application is a method for preparing the phenyl amidine compound or salt thereof, comprising the following steps:

[0045] (1) reacting compound III with compound II to obtain compound I, and the chemical reaction equation is as follows:

[0046] Alternatively, (2) when X represents O or S, reacting compound IV with compound V to obtain compound I, and the reaction equation is as follows:

[0047] wherein L represents halogen, and the definitions of substituents R1, R2, R3, R4, R6, X, M and Q are as described above.

[0048] In one specific embodiment, the reaction (1) is carried out in the presence of a catalyst and a solvent.

[0049] In another specific embodiment, the catalyst is selected from at least one of oxalyl chloride, thionyl chloride or phosphorus oxychloride.

[0050] In another specific embodiment, the solvent is selected from at least one of benzene, toluene, dichloromethane, dichloroethane, acetonitrile, methanol, ethanol, diethyl ether, tetrahydrofuran or 1,4-dioxane.

[0051] In one specific embodiment, the reaction (2) is carried out in the presence of a base and a solvent.

[0052] In another specific embodiment, the solvent is selected from at least one of N,N-dimethylformamide, acetonitrile, diethyl ether, dimethyl sulfoxide, dichloromethane or dichloroethane.

[0053] In another specific embodiment, the base is selected from at least one of an inorganic base (such as potassium carbonate, sodium carbonate, NaH, KH, KOH, NaOH, cesium carbonate, etc.) or an organic base (such as potassium tert-butoxide, sodium tert-butoxide, sodium ethoxide, etc.).

[0054] In addition, another embodiment of the present application is a fungicidal composition comprising a biologically effective amount of the compound of formula I; preferably, in one specific embodiment, further comprising a formulation aid; and in another specific embodiment, further comprising other effective ingredients.

[0055] Another embodiment of the present application is the use of the compound of formula I or the above-mentioned fungicidal composition for controlling phytopathogenic fungi. For protecting plants from attack by phytopathogenic microorganisms or for treating plants that have been attacked by phytopathogenic microorganisms, the use comprises applying the compound of formula I or the composition containing the compound to the soil, the plants, parts of the plants, the leaves, and / or the roots.

[0056] The compounds of the present application can be applied as the compound or as a formulation containing the compound by any of a variety of known techniques. For example, the compounds can be applied to the roots or foliage of a plant to control a variety of fungi without destroying the commercial value of the plant. The substances can be applied in the form of any of the formulation types customarily used, for example, as a solution, dust, wettable powder, flowable concentrate or emulsifiable concentrate.

[0057] Preferably, the compounds of the present application are applied in the form of a formulation comprising one or more compounds of Formula I and a phytologically acceptable carrier. Concentrated formulations can be dispersed in water or other liquids for application, or the formulation can be a dust or granule which can be applied without further treatment. The formulations can be prepared according to methods commonly used in the agrochemical art.

[0058] The present application contemplates the use of all vehicles by which the one or more compounds can be formulated for delivery and use as fungicides. Typically, the formulations are applied in the form of an aqueous suspension or emulsion. The suspension or emulsion can be prepared from water-soluble, water-suspendable or emulsifiable formulations, which are often referred to as wettable powders when they are solids or emulsifiable concentrates, aqueous suspensions or suspension concentrates when they are liquids. It will be readily understood that any agent by which these compounds can be incorporated can be used, provided that the desired utility is obtained without significant impairment of the activity of these compounds as antifungal agents.

[0059] Wettable powders, which can be compressed into water dispersible granules, comprise an intimate mixture of one or more compounds of Formula I, an inert carrier and surfactants. The concentration of the compound in the wettable powder can range from about 10 wt% to about 90 wt%, more preferably from about 25 wt% to about 75 wt%, based on the total weight of the wettable powder. In the preparation of wettable powder formulations, the compound can be compounded with any finely divided solid, such as prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite, diatomaceous earth, purified silicates, and the like. In the operation, the finely divided carrier and surfactants are usually blended and ground with the compound.

[0060] Emulsions of the compounds of Formula I can comprise the compound in a conventional concentration in a suitable liquid, for example from about 1 wt% to about 50 wt%, based on the total weight of the emulsion. The compound can be dissolved in an inert carrier which is a mixture of a water-miscible solvent or a water-immiscible organic solvent and an emulsifying agent. The emulsion 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 aromatic fractions of petroleum, especially high-boiling naphthenic and olefinic fractions, such as heavy aromatic naphthas. Other organic solvents can also be used, such as terpene solvents including rosin derivatives, aliphatic ketones such as cyclohexanone, and complex alcohols such as 2-ethoxyethanol.

[0061] Emulsifiers that can be advantageously employed in the present application can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers. Examples of nonionic emulsifiers for use in preparing the emulsions include polyalkylene glycol ethers, and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide, such as ethoxylated alkyl phenols and carboxylic acid esters solubilized with a polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and salts of fatty amines. Anionic emulsifiers include oil-soluble salts (e.g., calcium salts) of alkyl aryl sulfonic acids, oil-soluble salts of sulfated polyglycol ethers, and suitable salts of phosphated polyglycol ethers.

[0062] Representative organic liquids that can be employed in the preparation of emulsions of the compounds of the present application are aromatic liquids such as xylene and propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, especially dimethyl amides of aliphatic glycols and glycol derivatives such as the n-butyl, ethyl or methyl ether of diethylene glycol, the methyl ether of triethylene glycol, petroleum distillate or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oil, and the like; 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, and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids can also be employed in the preparation of the emulsions. The organic liquids include xylene and propyl benzene fractions, with xylene being the most preferred in some cases. A surface active dispersant is generally employed in the liquid formulation, and the amount of the surface active dispersant is 0.1 to 20 wt% based on the total weight of the dispersant and one or more compounds. The formulation can also contain other compatible additives such as plant growth regulators and other biologically active compounds used in agriculture.

[0063] Aqueous suspensions include a suspension of one or more water-insoluble compounds of Formula I dispersed in an aqueous vehicle, at a concentration of from about 1 wt% to about 50 wt%, based on the total weight of the aqueous suspension. The suspension is prepared by finely grinding one or more of the compounds and vigorously mixing the ground compound into a vehicle consisting of water and a surfactant selected from the same classes of surfactants described above. Other ingredients such as inorganic salts and synthetic or natural gums can also be added to increase the density and viscosity of the aqueous vehicle.

[0064] The compounds of Formula I can also be applied as granular formulations, which are particularly useful for application to soil. The granular formulations generally contain from about 0.5 wt% to about 10 wt% of the compound dispersed in an inert carrier, based on the total weight of the granular formulation, the inert carrier consisting entirely or mostly of a rough, crushed inert material such as attapulgite, bentonite, kieselguhr, clay or similar inexpensive material. The formulation is generally prepared by dissolving the compound in a suitable solvent in which the compound is substantially or completely soluble, and applying it to a granular carrier which has been previously prepared to the proper particle size (ranging from about 0.5 to about 3 mm). A suitable solvent is one in which the compound is substantially or completely soluble. The formulation can also be prepared by making a paste or dough of the carrier and compound and solvent, then crushing and drying to the desired granular size.

[0065] Powders containing the compounds of Formula I can be prepared by intimately mixing powdered one or more of the compounds with a suitable dusty agricultural carrier such as kaolin clay, ground volcanic rock or the like. The powders can suitably contain from about 1% to about 10% of the compound, based on the total weight of the powder.

[0066] The formulations can additionally contain auxiliary surfactants to enhance the deposition, wetting and penetration of the compound onto the target crop and microorganism. These auxiliary surfactants can optionally be used as components of the formulation or as tank mixes. The amount of the auxiliary surfactant is generally from 0.01 to 1.0 volume percent, preferably 0.05 to 0.5 volume percent, based on the volume of the water spray. Suitable auxiliary surfactants include, but are not limited to, ethoxylated nonyl phenol, ethoxylated synthetic or natural alcohols, sulfosuccinates or sulfonates, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyl dimethyl quaternary ammonium salt; blends of petroleum hydrocarbon, alkyl esters, organic acids and anionic surfactants; C9-C 11 alkyl polyglycoside; phosphated alcohol ethoxylate; natural primary alcohols (C 12 -C 16) ethoxylate; di-sec-butyl phenol EO-PO block copolymer; polysiloxane-methyl blocked; nonyl phenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8 EO); tallow amine ethoxylate (15 EO); PEG (400) dioleate-99. The formulations can also include oil-in-water emulsions such as those disclosed in U.S. Patent Application Serial No. 11 / 495,228, the disclosure of which is incorporated herein by reference.

[0067] The formulations can optionally include combinations with other pesticidal compounds. The additional pesticidal compounds can be fungicides, insecticides, herbicides, nematicides, miticides, arthropodicides, bactericides, or combinations thereof, which are compatible with the compounds of the application in the medium chosen for application and do not antagonize the activity of the compounds of the application. Thus, in the embodiments, the other pesticidal compounds are used as supplemental toxicants for the same or different pesticidal use. The compounds of the formula I and the pesticidal compounds can generally be present in a combination in a weight ratio of 1 : 100 to 100: 1.

[0068] The compounds of the present application can also be combined with other fungicides to form fungicidal mixtures and their synergistic mixtures. The fungicidal compounds of the present application are often 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 the present application can be formulated together with other fungicides, tank mixed with other fungicides, or applied sequentially with other fungicides. The other fungicides can include: 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxy quinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Burgundy mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium Minitans, copper hydroxide, copper oxychloride, copper sulfate, coumoxystrobin, cyflufenamid, cymoxanil, cyprodinil, cyproconazole, cytosine, dichlofluanid, diclomezni, diclomezni, dicloran, diethofencarb, dimethomorph, dimethomorph, dimethomorph, dimethomorph, dithianon, dodine, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine 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free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodine free acid, dodcopper octanoate, 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, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, ferbam, ferimzone, fluazinam, fludioxonil, flufenoxuron, flusilazole, flutriafol, folpet, formaldehyde, formetoxam, fosetyl, fosetyl-aluminum, fthalin, fuberidazole, furalaxyl, guazatine, guazatine-acetate, hexachlorobenzene, hexythiazox, hymexazol, imazalil, imazalil-sulfate, imibenconazole, iminoctad, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isothioicarb, kasugamycin, kasugamycin-hydrochloridehydrate, kresoxim-methyl, mancopper, maneb, mefenoxam, mepronil, meptyldinocap, mercuric chloride, mercury hemisulfate, metiram, metiram-zinc, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrophenide, nitro- oxydine, nitro- oxydinil, octhilinone, ofurace, organomercury, oxamadol, oxolinic acid, oxy-carboxin, peat, pencycuron, pentachlorphenole, pentachlorophenole-sodiumsalz, penthrinite, penthiopyrad, phenazine, phenazine-1-carboxylate, phenamacril, phenisopham, phthalide, picoxystrobin, piperalin, polycarbamate, polyoxine, potassium hydroxyde, potassium sodium copper chloride, probenazole, procymidon, propamocarb, propineb, propiconazole, propomocarb hydrochloride, proquinazid, protrifenbute, pyracarbolid, pyraclostrobin, pyrametostrobin, pyramoxystrobin, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quaternary ammonium compounds, quinoxyfen, quintozene, rabenzazole, reclavine, reclorine, spiroxamine, silthiofam, sodium dehydroacetic acid, sodium-2,3-dihydro-3, 3-dimethyl-2H-inden-1-one, sodium-2-mercaptobenzothiazole, sulfur, sulfuric acid, SYP-ZC051, tebufloquin, tecloftalam, tecloftalam-sodiumsalz, tecloftalam-zincsalz, tebufenpyrad, tebufloquin, tecloftalam,fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb,precis, proquinazid, propamocarb, propineb, propionic acid (fatty acid), propionibacterium cerevicum, propionylethylglycine betaine, propyzamid, proquinazid, prothioconazole, prothiocarb, protoporphyrinogen-IX oxidase inhibitors, protoporphyrinogen oxidase inhibitors, pyraclostrobin, pyrametostrobin, pyramoxystrobin, pyraziflumid, pyridaben, pyridinitr, pyridyl-1,3,5-triazines, pyriftalid, pyrimethanil, pyrithiobac-ethyl, pyroquilon, pyroxasulfone, pyrusia, pyrusulfola, pyrusulfola, quaternary ammonium compounds, quaternary phosphorus compounds, quinomethionid, quinoxyfen, quinoclamine, quinoxyfen, quinoclamine, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinoclamine, quinomethionid, quinoxyfen, quinprochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrif enox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenyl phenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, 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, 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, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanateme, 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, CECA, Chlobenthiazone, Chloraniformethan, Chlorfenazole, Chlorquinox, Climbazole, Copper bis(3-phenylsalicylate), Copper zinc chromate, Cufraneb, Cupric hydrazinium sulfate, Cuprobam, Cyclafuramid, Cypendazole, Cyprofuram, Decafentin, Dichlone, Dichlozoline, Diclobutrazol, Dimethirimol, Dinocton, Dinosulfon, Dinoterbon, Dipyrithione, Ditalimfos, Dodicin, Drazoxolon, EBP, ESBP, Etaconazole, Etem, Ethirim, Fenaminosulf, Fenapanil, Fenitropan, Fluotrimazole, Furcarbanil, Furconazole, Furconazole-cis,furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICI A0858, isopamphos, isovaledione, mebenil, mearbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenylsuccinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen,Thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trihlamide, urethane, zarilamid, and any combinations thereof.

[0069] In addition, the compounds described herein can be combined with other pesticides, including insecticides, nematicides, miticides, arthropodicides, fungicides or combinations thereof, which are compatible with the compounds of the present application in the medium selected for application and do not antagonize the activity of the compounds of the present application to form pesticidal mixtures and their synergistic mixtures. The fungicidal compounds of the present application can be applied in conjunction with one or more other pesticides to provide control of a wider range of undesirable pests. When applied in conjunction with other pesticides, the compounds claimed herein can be formulated together with the other pesticides, tank mixed with the other pesticides, or applied sequentially with the other pesticides. Common insecticides include, but are not limited to: 1,2-dichloropropane, abamectin, acephate, acetamiprid, acethion, acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb, aldoxycarb, aldrin, allethrin, allosamidin, allyxycarb, alpha-cypermethrin, alpha-ecdysone, alpha-endosulfan, amidithion, aminocarb, amiton, amiton oxalate, amitraz, anabasine, athidathion, azadirachtin, azamethiphos, azinphos-ethyl, azinphos-methyl, azothoate, barium hexafluorosilicate, barthrin, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin, beta-cypermethrin, bifenthrin, bioallethrin, bioethanomethrin, bioresmethrin, biopermethrin,bistrifluron, borax, boric acid, bromfenvinfos, bromocyclen, bromo-DDT, bromophos, bromophos-ethyl, bufencarb, buprofezin, butacarb, butathiofos, butocarboxim, butonate, butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide, camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbontetrachloride, carbophenothion, carbosulfan, cartap, cartap hydrochloride, chlorantraniliprole, chlorbicyclen, chlordane, chlordecone, chlordimeform, chlordimeform hydrochloride, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroform, chloropicrin, chlorphoxim, chlorprazophos, chlorpyrifos, chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I, cinerin II, cinerins, cismethrin, cloethocarb, closantel,thiamethoxam, copper acetoarsenite, copper arsenate, copper naphthenate, copper oleate, coumaphos, coumithoate, crotamiton, crotoxyphos, crufomate, cryolite, cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyclethrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin, cyromazine, cythioate, DDT, decarbofuran, deltamethrin, demephion, demephion-O, demephion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos, diatomaceous earth, diazinon, dicapthon, dichlofenthion, dichlorvos, dicresyl, dicrotophos, dicyclanil, dieldrin, diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate, dimethrin,Methylvinphos, Dimetilan, Dinex, Dinex-diclexine, Dinoprop, Dinosam, Dinotefuran, Diofenolan, Dioxabenzofos, Dioxacarb, Dioxathion, Disulfoton, Dithicrofos, d-limonene, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, Doramectin, Ecdysterone, Emamectin, Emamectin benzoate, EMPC, Empenthrin, Endosulfan, Endothion, Endrin, EPN, Epofenonane, Eprinomectin, Esdepalléthrine, Esfenvalerate, Etaphos, Ethiofencarb, Ethion, Ethiprole, Ethoate-methyl, Ethoprophos, Ethyl formate, Ethyl-DDD, 1,2-Dibromoethane, 1,2-Dichloroethane, Ethylene oxide, Etofenprox, Etrimfos, EXD, Famphur, Fenamiphos, Fenazaflor, Fenchlorphos, Fenethacarb, Fenfluthrin, Fenitrothion, Fenobucarb, Fenoxacrim, Fenoxycarb, Fenpirithrin, Fenpropathrin,fensulfothion, fenthion, fenthion-ethyl, fenvalerate, fipronil, flonicamid, flubendiamide, flucofuron, flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox, fluvalinate, fonofos, formetanate, formetanate hydrochloride, formothion, formparanate, formparanate hydrochloride, fosmethilan, fospirate, fosthietan, furathiocarb, furethrin, gamma-cyhalothrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD, heptachlor, heptenophos, heterophos, hexaflumuron, HHDN, hydramethylnon, hydrogen cyanide, hydroprene, hyquincarb, imidacloprid, imiprothrin, indoxacarb, iodomethane, IPSP, isazofos, isobenzan, isocarbophos, isodrin, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane, isothioate, isoxathion, ivermectin, jasmolin I,jasmolin II, jodfenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan, kinoprene, lambda-cyhalothrin, lead arsenate, lepimectin, leptophos, lindane, lirimfos, lufenuron, lythidathion, malathion, malonoben, mazidox, mecarbam, mecarphon, menazon, mephosfolan, mercurous chloride, mesulfenfos, metaflumizone, methacrifos, methamidophos, methidathion, methiocarb, methocrotophos, methomyl, methoprene, emthoxychlor, methoxyfenozide, methyl bromide, methyl isothiocyanate, methyl chloroform, methylenechloride, metofluthrin, metolcarb, metoxadiazone, mevinphos, mexacarbate, milbemectin, milbemycinoxime, mipafox, mirex, molosultap, monocrotophos, monomehypo, monosultap, morphothion, moxidectin, naftalofos, naled,naphthalene, nicotine, nifluridide, nitenpyram, nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl, oxydemeton-methyl, oxydeprofos, oxydisulfoton, para-dichlorobenzene, parathion, parathion-methyl, penfluron, pentachlorophenol, permethrin, phenkapton, phenothrin, phenthoate, phorate, phosalone, phosfolan, phosmet, phosnichlor, phosphamidon, phosphine, phoxim, phoxim-methyl, pirimetaphos, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassium arsenite, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, primidophos, profenofos, profluralin, promacyl, promecarb, propaphos, propetamphos, propoxur, prothidathion, prothiofos, prothoate, protrifenbute, pyraclofos, pyrafluprole, pyrazophos,pyresmethrin, pyrethrin I, pyrethrin II, pyrethrins, pyridaben, pyridalyl, pyridaphenthion, pyrifluquinazon, pyrimidifen, pyrimithate, pyriprole, pyriproxyfen, quassia, quinalphos, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, ryania, sabadilla, schradan, selamectin, silafluofen, silica gel, sodium arsenite, sodium fluoride, sodium hexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad, spiromesifen, spirotetramat, sulcofuron, sulcofuron-sodium, sulfluramid, sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, tau-fluvalinate, tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, tefluthrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane, tetrachlorvinphos, tetramethrin,tetramethylfluthrin, theta-cypermethrin, thiacloprid, thiamethoxam, thicrofos, thiocarboxime, thiocyclam, thiocyclam oxalate, thiodicarb, thiofanox, thiometon, thiosultap, thiosultap-disodium, thiosultap-monosodium, thuringiensin, tolfenpyrad, tralomethrin, transfluthrin, transpermethrin, triarathene, triazamate, triazophos, trichlorfon, trichlormetaphos-3, trichloronat, trifenofos, triflumuron, trimethacarb, triprene, vamidothion, vaniliprole, XMC, xylylcarb, zeta-cypermethrin, zolaprofos, and any combination thereof.

[0070] In addition, the compounds described herein can be combined with herbicides that are compatible with the compounds of the present application in the medium selected for application and do not antagonize the activity of the compounds of the present application to form insecticidal mixtures and their synergistic mixtures. The fungicidal compounds of the present application are generally applied in combination with one or more herbicides to control a wider range of undesirable plants. When applied in combination with herbicides, the compounds claimed herein can be formulated together with the herbicide, tank mixed with the herbicide, or applied sequentially with the herbicide. Common herbicides include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 3,4-DA; 2,4-DB; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate, bensulfuron, bensulide, bentazone, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop,thiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin,Cinosulfuron, Cisanilide, Clethodim, Cliodinate, Clodinafop, Clofop, Clomazone, Clomeprop, Cloprop, Cloproxydim, Clopyralid, Cloransulam, CMA, Copper sulfate, CPMF, CPPC, Credazine, Cresol, Cumyluron, Cyanatryn, Cyanazine, Cycloate, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop, Cyperquat, Cyprazine, Cyprazole, Cypromid, Daimuron, Dalapon, Dazomet, Delachlor, Desmedipham, Desmetryn, Di-allate, Dicamba, Dichlobenil, Dichloralurea, Dichlormate, 2,4-Dichlorprop, Dichlorprop-P, Dichlofop, Diclosulam, Diethamquat, Diethatyl, Difenopenten, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimexano, Dimidazon, Dinitramine, Dinofenate,Dinoprop, Dinosam, Dinoseb, Dinoterb, Diphenamid, Dipropetryn, Diquat, Disul, Dithiopyr, Diuron, DMPA, DNOC, DSMA, EBEP, Eglinazine, Endothal, Epronaz, EPTC, Erbon, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethidimuron, Ethiolate, Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etinofen, Ethnipromid, Etobenzanid, EXD, Fenasulam, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fenoxasulfone, Fenteracol, Fenthiaprop, Fentrazamide, Fenuron, Ferrous sulfate, Flamprop, Flamprop-M, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-P, Fluazolate, Flucarbazone, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenican, Flufenpyr, Flumetsulam, Flumezin, Flumiclorac, Flumioxazin, Flumipropyn, Fluometuron, Fluorodifen, Fluoroglycofen, Fluoromidine,Fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, furyloxyfen, glufosinate, glufosinate-P, glyphosate, halosafen, halosulfuron, haloxydine, haloxyfop, quizalofop-P (haloxyfop-P), hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indicarb indanofan), indaziflam, iodobonil, iodomethane, iodosulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocillin, isomethiozin, isoruron, nitrogen, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, methylarsenic acid (MAA), monam (monammonium acrylate), 2,4-D, MCPA-thioethyl, 2,4-DB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, monosodium methylarsenate (MSMA),naphthalene propylamine (naproanilide), napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, octhilinone (OCH), orbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, quinoclamine, quinonamid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid,sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, tridiphane, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate, and xylachlor.

[0071] Another embodiment of the present application is a method for controlling harmful fungi. This comprises treating the fungi or the materials, plants, soil or seeds to be protected from fungal attack with a compound of formula I or the fungicidal compositions described above.

[0072] It has been found that the compounds have remarkable fungicidal action, in particular for agricultural use. A number of the compounds are particularly effective for use on agricultural crops and horticultural plants.

[0073] Those skilled in the art will appreciate that the efficacy of the compounds against the aforementioned fungi establishes the general utility of the compounds as fungicides.

[0074] The compounds have a broad range of activity against fungal pathogens. Exemplary pathogens can include, but are not limited to, the causing agents of wheat leaf blotch (Zymoseptoria tritici), wheat brown rust (Puccinia triticina), wheat stripe rust (Puccinia striiformis), scab of apple (Venturia inaequalis), powdery mildew of grapevine (Uncinula necator), barley scald (Rhynchosporium secalis), blast of rice (Pyricularia oryzae), rust of soybean (Phakopsora pachyrhizi), glume blotch of wheat (Leptosphaeria nodorum), powdery mildew of wheat (Blumeria graminis f. sp. tritici), powdery mildew of barley (Blumeria graminis f. sp. hordei), powdery mildew of cucurbits (Erysiphe cichoracearum), Anthracnose of cucurbits (Colletotrichum lagenarium), leaf spot of beet (Cercospora beticola), early blight of tomato (Alternaria solani), and spot blotch of barley (Cochliobolus sativus).The exact amount of active substance to be applied depends not only on the particular active substance to be applied, but also on the particular action to be achieved, the fungal species to be controlled and its growth stage, and the part of the plant or other objects to be contacted with the compound. Thus, all compounds and formulations containing the compounds can not be equally effective at similar concentrations or against the same species of fungi.

[0075] The compounds are effective for use on plants in fungicidally and phytologically acceptable amounts. The term "fungicidally and phytologically acceptable amount" means the amount of the compound which kills or inhibits (as desired) the growth of unwanted fungi but is not significantly toxic to plants. This amount is generally from about 0.1 to about 1000 ppm (parts per million), preferably 1 to 500 ppm. The exact concentration of the desired compound will vary with the fungal disease to be controlled, the type of formulation employed, the method of application, the particular plant species, the climatic conditions, etc. Suitable application rates will generally be in the range of about 0.10 to about 4 pounds per acre (about 0.01 to 0.45 grams per square meter, g / m 2 ) of the active ingredient.

[0076] It will be apparent to those skilled in the art that any of the ranges or desired values given herein can be extended or modified without loss of generality. DETAILED DESCRIPTION

[0077] The following examples are intended to illustrate the application and should not be construed as limiting the application in any way. The scope of the patent protection sought is defined by the claims.

[0078] In view of the economics and versatility of the compounds, we have preferably synthesized a number of compounds, among which some are selected and listed in Table 1 below. The structures of the specific compounds and the corresponding compound information are shown in Table 1 and Table 2. The compounds in Table 1 are only for better illustrating the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0079] Table 1 Compound Structure

[0080] Table 2 Compound 1 H NMR Values

[0081] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be purchased from vendors or can be prepared by known methods in the literature or as illustrated. Those skilled in the art will appreciate that other synthetic routes can be used to practice the application. Although specific starting materials and conditions are given in the following examples, other similar starting materials and conditions can be easily determined by those skilled in the art to be within the scope of the application. In addition, the synthetic methods described below can be further modified using conventional chemistry known to those skilled in the art, as disclosed herein. For example, protecting groups can be added to appropriate groups during the course of the reactions, etc.

[0082] The following examples of the methods are provided to further illustrate the preparation of the compounds of the present application, the specific materials, amounts and conditions used are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds described below can be purchased from vendors or can be readily prepared by one of ordinary skill in the art.

[0083] Representative compounds are prepared as follows, other compounds are prepared by analogous methods, which are not described in detail.

[0084] 1. Synthesis of compound 2

[0085] Compound 2-2 (1.3 g, 14.6 mmol) was dissolved in dichloromethane under ice bath condition, then oxalyl chloride (2.23 g, 17.5 mmol) was added slowly, after 0.5 h stirring, compound 2-1 (1.5 g, 5.9 mmol) in dichloromethane was added dropwise. The reaction was continued for 2 h, LCMS was used to monitor the reaction completion. The reaction was poured into water, extracted with dichloromethane, dried over sodium sulfate, concentrated under reduced pressure, the residue was purified by reverse phase to give a light yellow solid, the solid was washed with saturated NaHC03solution for several times, the organic phase was dried and concentrated to give compound 2 (light yellow oil, 1.2 g, 63%).

[0086] 2. Synthesis of compound 59

[0087] Compound 2-2 (0.4 g, 2.5 eq) was weighed in a round bottom flask, dissolved in 5 mL dichloromethane, oxalyl chloride (0.58 g, 0.4 mL, 2.5 eq) was added dropwise under ice bath, the reaction was continued for 30 min, compound 59-1 (0.5 g, 1.0 eq) dissolved in dichloromethane was added dropwise under ice bath, the reaction was continued for 30 min. The reaction was directly rotary evaporated, slurry in dichloromethane and ethyl acetate to give white solid 59 (0.34 g, purity 96%, yield 54%).

[0088] 3. Synthesis of compound 82

[0089] Compound 82-1 (600 mg, 2.92 mmol) and 82-2 (528 mg, 3.50 mmol) were dissolved in 10 ml of N,N-dimethylformamide, NaH (350 mg, 8.76 mmol) was added at 0 °C, and the temperature was raised to 80 °C and stirred for 6 h. The reaction was monitored by LCMS. The reaction was quenched by water, diluted with ethyl acetate, and the organic phase was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography to give compound 82 (550 mg, 44%) as a white solid.

[0090] 4. Synthesis of compound 36

[0091] N,N-dimethylformamide (120 mg, 1.17 mmol) was dissolved in 5 mL of dichloromethane solution under ice bath condition, then oxalyl chloride (150 mg, 1.17 mmol) was added slowly, after stirring for 0.5 h, compound 2-1 (200 mg, 0.78 mmol) in dichloromethane was added dropwise. Continue to stir for 1 h, the reaction was monitored by LCMS. The reaction was poured into water, extracted with dichloromethane, the organic phase was washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography to give compound 36 (90 mg, 34%).

[0092] 5. Synthesis of compound 87

[0093] (1) Compound 87-1 (3.5 g, 10.1 mmol) was dissolved in 100 mL of toluene, then 3-mercapto propionic acid ethyl ester (1.5 g, 11.1 mmol), bis(2-diphenylphosphinophenyl) ether (1.6 g, 3.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol) and potassium carbonate (4.2 g, 30.3 mmol) were added, the system was replaced with nitrogen three times, and the temperature was raised to 100 °C and reacted overnight. The next day, the reaction was monitored by LCMS. The filtrate was concentrated and purified by normal phase to give compound 87-2 (2.5 g, 62.5%).

[0094] (2) Compound 87-2 (2.5 g, 6.3 mmol) was dissolved in 30 mL of tetrahydrofuran, and compound potassium tert-butoxide (2.1 g, 18.8 mmol) was added under ice bath condition, and the temperature was raised to room temperature and reacted overnight. The next day, the reaction was monitored by LCMS. The system was poured into water, extracted with ethyl acetate, the organic phase was concentrated, and purified by normal phase to give compound 87-3 (1.7 g, 90.7%).

[0095] (3) Compound 87-3 (1.7 g, 5.7 mmol) was dissolved in 20 mL of N,N- dimethylformamide, and then compound iodomethane (1.2 g, 8.5 mmol) and potassium carbonate (2.4 g, 17.1 mmol) were added, and the reaction was carried out at 80°C overnight. The next day, the reaction was monitored by LCMS. The system was poured into water, and extracted with ethyl acetate. The organic phase was washed with saturated brine 4-5 times, and the organic phase was concentrated and purified by normal phase to obtain compound 87-4 (1.5 g, 84.3%).

[0096] (4) Compound 87-4 (1.5 g, 4.7 mmol) was dissolved in 20 mL of dichloromethane, and then compound meta-chloroperoxybenzoic acid (580 mg, 3.8 mmol) was added under ice bath, and the reaction was carried out at room temperature for 2 hours. The reaction was monitored by LCMS. The system was poured into water, and extracted with dichloromethane. The concentrated normal phase was purified to obtain compound 87-5 (820 mg, 52.0%).

[0097] (5) Compound 87-5 (820 mg, 2.5 mmol) was dissolved in a mixed solvent of ethanol (12 mL) and water (3 mL), and then iron powder (560 mg, 10.0 mmol) and ammonium chloride (688 mg, 12.5 mmol) were added, and the reaction was carried out at 80°C overnight. The next day, the reaction was monitored by LCMS. The system was filtered and concentrated, and purified by normal phase to obtain compound 87-6 (500 mg, 67.1%).

[0098] (6) Compound 2-2 (500 mg, 1.7 mmol) was dissolved in 5 mL of dichloromethane, and then compound oxalyl chloride (630 mg, 5.0 mmol) was added under ice bath. After stirring for 10 minutes under ice bath, compound 87-6 (370 mg, 4.2 mmol) was added, and the reaction was continued for half an hour. The reaction was monitored by LCMS. The system was poured into water, and extracted with dichloromethane. The concentrated normal phase was purified to obtain compound 87 (60 mg, 9.8%).

[0099] 6. Synthesis of compound 105

[0100] (1) Compound 105-1 (2000 mg, 8.13 mmol) was dissolved in acetonitrile (20 mL) at room temperature, and cuprous chloride (956 mg, 9.76 mmol), copper chloride (1297 mg, 9.76 mmol) and tert-butyl nitrite (1256 mg, 12.2 mmol) were added successively. After completion of the addition, the mixture was stirred at room temperature for 2 h. After completion of the reaction, water was added, and the mixture was extracted with ethyl acetate three times. The combined organic phase was washed with saturated brine once, dried, concentrated, and purified by normal phase to obtain compound 105-2 (1600 mg, 74%).

[0101] (2) Compound 105-2 (1600 mg, 6.04 mmol) was dissolved in 1,2-dichloroethane (20 mL) under ice bath conditions, and boron tribromide (2984 mg, 12.08 mmol) was slowly added. After completion of the addition, the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, poured into ice water, and extracted with dichloromethane three times. The combined organic phase was washed with saturated brine once, dried, concentrated, and purified by normal phase to obtain compound 105-3 (1400 mg, 92%).

[0102] (3) Compound 105-3 (1400 mg, 5.58 mmol) was dissolved in 20 mL of a solvent mixture of ethanol / water (4 / 1) at room temperature, and iron powder (937 mg, 16.74 mmol) and ammonium chloride (887 mg, 16.74 mmol) were added successively. After completion of the addition, the mixture was heated to 80°C and stirred for 2 h. After completion of the reaction, the mixture was filtered through celite, and the filtrate was concentrated to remove ethanol. The mixture was extracted with ethyl acetate three times, and the combined organic phase was washed with saturated brine once, dried, and concentrated to obtain crude compound 105-4 (1400 mg, 114%).

[0103] (4) Compound 105-4 (250 mg, 1.13 mmol) was dissolved in 10 mL of N,N-dimethylformamide at room temperature, and 3,4-difluorobenzonitrile (157 mg, 1.13 mmol) and potassium carbonate (468 mg, 3.39 mmol) were added successively. After completion of the addition, the mixture was heated to 60°C and stirred overnight. After completion of the reaction, water was added, and the mixture was extracted with ethyl acetate three times. The combined organic phase was washed with saturated brine three times, dried, concentrated, and purified by normal phase to obtain crude compound 105-5 (300 mg, 78%).

[0104] (5) Under ice-bath condition, compound 2-2 (115 mg, 1.32 mmol) was dissolved in dichloromethane (10 mL), oxalyl chloride (221 mg, 1.76 mmol) was added slowly, stirred for 30 min under ice-bath, concentrated to remove solvent and residual oxalyl chloride, dissolved in 10 mL dichloromethane, stirred under ice-bath, compound 105-5 (300 mg, 0.88 mmol) in dichloromethane was added dropwise slowly, after addition, stirred for 1 h. After completion of reaction, solvent was removed by concentration, washed with ethyl acetate for 3 times, adjusted to weak alkaline with aqueous sodium bicarbonate solution, extracted with ethyl acetate, combined organic phase was washed with saturated brine for 1 time, dried and concentrated, and then purified by normal phase to obtain compound 105 (200 mg, 55%).

[0105] Biological activity evaluation:

[0106] The dimethyl sulfoxide was selected as the solvent, and the solvent was diluted with 0.1% Tween 80 aqueous solution to different concentrations. Each concentration was treated with 3 replicates, and a solvent without the agent was used as a control. The liquid was evenly sprayed on the leaf surface until the whole was wet, and the liquid was naturally dried for standby after the liquid was naturally dried.

[0107] The test targets were Puccinia polysora Unodrew., Colletotrichum orbiculare Arx., and Sphaerotheca cucurbitae cultured on living pot plants. The spores on the surface of soybean and cucumber leaves were washed with 0.1% Tween 80 aqueous solution, and a suspension was prepared (the concentration was 4x10 5 6 spores per milliliter). The fresh spore suspension was sprayed on the leaf surface, and the protective test was inoculated 24 h after the agent was treated. After inoculation, the leaves were placed in a dark environment with a relative humidity of more than 90% and a temperature of about 25°C. After 24 h, the leaves were cultured alternately under light and in the dark for 12 h each.

[0108] According to the disease condition of the blank control (when the disease reached level 9), the inoculated leaves were graded. The following grading method was used:

[0109] 0: no disease;

[0110] 1: the disease spot area accounted for less than 5% of the whole leaf area;

[0111] 3: the disease spot area accounted for 6% to 10% of the whole leaf area;

[0112] 5: the disease spot area accounted for 11% to 25% of the whole leaf area; ​

[0113] 7 grade: the area of disease spot accounts for 26% to 50% of the whole leaf area;

[0114] 9 grade: the area of disease spot accounts for more than 50% of the whole leaf area.

[0115] According to the investigation data, the disease index and the control effect of each treatment are calculated.

[0116] The disease index is calculated according to formula (1), and the calculation result is kept to two decimal places: X = {(∑(Ni x i)) / (N x 9)}x 100 …………………………………………(1)

[0117] In the formula: X - disease index; Ni - the number of leaves of each grade; i - the relative grade value; N - the total number of investigation leaves.

[0118] The control effect is calculated according to formula (2): P = {(CK-PT) / CK}x 100 …………………………………………(2)

[0119] In the formula: P - control effect, unit: percentage (%); CK - disease index of blank control; PT - disease index of chemical treatment.

[0120] Table 3 control results of representative compounds Note: N represents no data; control compound A:

[0121] Meanwhile, it is found through many tests that the compounds and the compositions have good control activity on different kinds of fungi such as basidiomycetes and deuteromycetes, and have certain commercial value.

Claims

1. A phenyl amidine compound represented by the following formula I: ###0001### or a salt thereof. wherein, X represents O, S or CH2; M represents C-R5or N; Q represents N(Y)2or a 5- or 6-membered heterocyclic group having a nitrogen at the 1-position; Y independently represents hydrogen, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclic group, heterocyclic group alkyl or -OR7; R1, R2each independently represents hydrogen, cyano, halogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -OR7or -S(O)mR7; m R7; R3, R4, R5each independently represents hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, -N(R7)2, -OR7or -S(O)mR7; R6represents hydrogen, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, -N(R7)2, -OR7or -S(O)mR7; R7represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heterocyclyl or heterocyclylalkyl; m represents 0, 1 or 2; and n represents 0, 1, 2, 3 or 4. m R7; wherein said "alkyl", "alkenyl" or "alkynyl" is R6represents halogen, OR, S(O) n R or OS(O)2R; R7independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclic group; m represents 0, 1 or 2; n represents 0, 1 or 2; R independently represents hydrogen, alkyl or haloalkyl; The foregoing "cycloalkyl", "cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, haloalkenyl, haloalkynyl, halocycloalkyl, cycloalkyl substituted with alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2 or -O-alkylene-(CO)OR 10 . R 10 each independently represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, or haloalkynyl.

2. The phenyl amidine compound or salt thereof according to claim 1, wherein Q represents N(Y)2or a 5- or 6-membered heterocyclic group having a nitrogen at the 1-position; Y independently represents hydrogen, cyano, C1-C8 alkyl, haloC1-C8 alkyl, C2-C8 alkenyl, haloC2-C8 alkenyl, C2-C8 alkynyl, haloC2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclic group, heterocyclic groupC1-C8 alkyl or -OR7; R1, R2independently represent hydrogen, cyano, halogen, Ci-C8alkyl, halo-Ci-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C2-C8alkynyl, halo-C2-C8alkynyl, -OR7or -S(O)mR7; m R7; R3, R4, and R5 independently represent hydrogen, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, -N(R7)2, -OR7, or -S(O), respectively. m R7; wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted with at least one group selected from halogen or -OR7; R7independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 haloalkyl, C2-C8 haloalkenyl, C2-C8 haloalkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl or heterocyclic group; m represents 0, 1 or 2; R independently represents hydrogen, C1-C8 alkyl or haloC1-C8 alkyl; The aforementioned "C3-C8cycloalkyl", "C3-C8cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one radical selected from oxo, halogen, cyano, nitro, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C8cycloalkyl, halogeno-C1-C8alkyl, halogeno-C2-C8alkenyl, halogeno-C2-C8alkynyl, halogeno-C3-C8cycloalkyl, C3-C8cycloalkyl substituted with C1-C8alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2or -O-(C1-C8alkylene)-(CO)OR 10 ; R 10 each independently represents hydrogen, C1-C8alkyl, haloC1-C8alkyl, C2-C8alkenyl, haloC2-C8alkenyl, C2-C8alkynyl or haloC2-C8alkynyl.

3. The phenyl amidine compound or salt thereof according to claim 1 or 2, wherein Q represents N(Y)2, Y independently represents hydrogen, cyano, C1-C6 alkyl, haloC1-C6 alkyl, C2-C6 alkenyl, haloC2-C6 alkenyl, C2-C6 alkynyl, haloC2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclic group, heterocyclic groupC1-C6 alkyl or -OR7; R1, R2independently represent hydrogen, cyano, halogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR7or -S(O)mR7; m R7; R3, R4, and R5 independently represent hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, -N(R7)2, -OR7, or -S(O), respectively. m R7; wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally substituted with at least one group selected from halogen or -OR7; R7independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 haloalkyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl or heterocyclic group; m represents 0, 1 or 2; R independently represents hydrogen, C1-C6 alkyl or haloC1-C6 alkyl; The foregoing "C3-C6cycloalkyl", "C3-C6cycloalkenyl", "heterocyclyl" or "aryl" is optionally substituted with at least one group selected from oxo, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C6cycloalkyl, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, halogenated C3-C6cycloalkyl, C3-C6cycloalkyl substituted with C1-C6alkyl, -OR 10 , -SR 10 , -(CO)OR 10 , -(SO2)R 10 , -N(R 10 )2or -O-(C1-C6alkylene)-(CO)OR 10 ; R 10 each independently represents hydrogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl or haloC2-C6alkynyl; Preferably, the compound is selected from any one of Table 1 of the specification.

4. A method for producing a phenyl amidine compound or salt thereof according to any one of claims 1 to 3, comprising the steps of: (1) Compound III is reacted with compound II to produce compound I, and the chemical reaction equation is as follows: Alternatively, (2) when X represents O or S, compound IV and compound V are reacted to produce compound I, the reaction being as follows: wherein, L represents halogen, and the definitions of the substituents R1, R2, R3, R4, R6, X, M and Q are as described in any one of claims 1 to 3.

5. The method for producing a phenyl amidine compound or salt thereof according to claim 4, wherein The reaction (1) is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is selected from at least one of oxalyl chloride, thionyl chloride or phosphorus oxychloride; preferably, the solvent is selected from at least one of benzene, toluene, dichloromethane, dichloroethane, acetonitrile, methanol, ethanol, diethyl ether, tetrahydrofuran or 1,4-dioxane; and / or The reaction (2) is carried out in the presence of a base and a solvent; preferably, the solvent is selected from at least one of N,N-dimethylformamide, acetonitrile, diethyl ether, dimethyl sulfoxide, dichloromethane or dichloroethane; preferably, the base is selected from at least one of an inorganic base or an organic base.

6. A fungicidal composition, characterized by, comprising a biologically effective amount of at least one of the phenylamidines according to any one of claims 1 to 3 or salts thereof; preferably, further comprising formulation adjuvants; more preferably, further comprising other active ingredients.

7. Use of the phenylamidines according to any one of claims 1 to 3 or salts thereof, or the fungicidal composition according to claim 6 for controlling phytopathogenic fungi.

8. A method for controlling harmful fungi, comprising treating the fungi or materials, plants, soil or seeds to be protected from fungal attack with an effective amount of the phenylamidines according to any one of claims 1 to 3 or salts thereof, or the fungicidal composition according to claim 6.

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