Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms

Abstract

The present invention relates to a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, the plant pathogenic microorganisms are selected from fusarium pseudograminearum, fusarium flavum, fusarium oxysporum, fusarium graminearum, rice-green sclerotium, claviceps millettii, botrytis cinerea, phytophthora sojae, phytophthora capsici, phytophthora infestans, helminthosporium buergerianum, helminthosporium longibrachiatum, colletotrichum gloeosporioides, colletotrichum truncatum, pythium delicillium, puccinia striiformis and puccinia multiflora. The present invention relates to a method for producing a compound of formula (I), comprising applying a compound of formula (I) to a useful plant, its locus, or its propagation material. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the field of plant protection, and in particular relates to a method for controlling or preventing useful plants from being attacked by phytopathogenic microorganisms, in particular Fusarium sp., such as Fusarium umpseudograminearum, Fusarium graminearum, Ustilaginoideavirens, Claviceps sorghi, Fusarium culmorum, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Exserohilum turcicum, Helminthosporium maydis, Colletotrichum gloeosporioides, Colletotrichum truncatum, Pythium truncatum, and Pythium truncatum. delienseMeurs), Puccinia striiformis, Puccinia polysoraUnderw, Pseudoperonosporacubensis and Erysiphe cichoracearum. Background Art

[0002] Fusarium sp., such as Fusarium pseudograminearum, Fusarium culmorum, Fusarium graminearum, Fusarium avenaceum, Fusarium moniliforme, Fusarium culmorum and Fusarium acuminatum, is a fungal pathogen that causes wheat head blight and wheat stem rot on wheat, especially Fusarium graminearum. If not controlled, the thousand-grain weight of wheat will decrease, the germination rate will decrease, the germination potential will weaken, the flour yield will be low, the flour quality will be poor, the color will be dark, and the commercial value will be reduced. At the same time, the diseased wheat contains toxins such as vomiting toxins and estrogen-like toxins, which can cause acute poisoning after being eaten by humans and animals. Diseased wheat grains contain toxins such as deoxynivalenol and zearalenone, which can cause poisoning and miscarriage in pregnant livestock. It can also infect cereal crops such as barley (Hordeum vulgare), rice (Oryza sativa), and oats (Arena sativa).

[0003] Ustilaginoideavirens is a fungal disease that causes rice false smut. The disease occurs only in the panicle, harming some of the grains on the panicle. It first appears as a small yellowish-green fungus block at the joint of the glume, gradually expands, and finally wraps the entire glume, which is dark green or olive, and finally cracks and is covered with dark green powder. Rice false smut is a major disease of rice, distributed in rice-producing areas around the world. The general incidence rate is 3-5%, and severe cases can reach more than 30%. The yield reduction can reach 20-30%, and the smut toxins produced are harmful to humans and animals. If not controlled, rice false smut can cause serious plant losses and yield reductions, endangering the health of humans and animals.

[0004] Claviceps sorghi is a fungal disease of sorghum that causes ergot disease in sorghum. The disease initially manifests as dark green and slightly wrinkled symptoms on the ovary, with white mycelial stroma on the surface at the base of the ovary. Gradually, the disease spreads upward, transforming the ovary into the fungal stroma. Symptoms on the stroma surface appear 5-10 days after infection, and pink to light brown honeydew is secreted from the infected ovary. There are currently no effective control measures other than the use of disease-resistant varieties. If not controlled, sorghum ergot disease can cause serious plant losses and reduced yields.

[0005] Botrytis cinerea is a broad-host fungal pathogen that can cause gray mold on tomatoes, and can also cause sudden wilting, leaf fall, flower rot, fruit rot and cellar rot in seedlings, fruits and storage organs of eggplant, lettuce, spinach, cucumber, sweet pepper, strawberry, basella, kidney bean, lettuce and many other plants. If not controlled, Botrytis cinerea can cause serious plant losses and reduced yields.

[0006] Phytophthora sojae is an oomycete disease that causes soybean blight, which can infect soybeans at all growth stages. It usually develops more severely in wet and rainy weather conditions, has a short incubation period, has many reinfections, spreads rapidly, and causes large-scale death of the host. If not controlled, soybean blight can lead to serious soybean losses and yield reductions.

[0007] Phytophthora capsici is an oomycete pathogen that causes pepper blight. Pepper blight can occur in both the seedling and plant stages, with the disease mainly occurring in the plant stage. The pathogen can infect roots, stems, leaves, and fruits. It is a devastating disease in greenhouse pepper production. In severe cases, it often causes crop failure and can also harm crops such as tomatoes, eggplants, and melons. If not controlled, pepper blight can cause serious plant losses and reduced yields.

[0008] Phytophthora infestans is an oomycete pathogen that causes potato late blight on potatoes. The disease primarily attacks the stems, leaves and tubers of potatoes, but can also infect flower buds and berries. If not controlled, potato late blight can lead to severe plant losses and reduced yields.

[0009] Exserohilum turcicum is a fungal pathogen that infects corn and causes corn leaf blight. The pathogen produces a special cell structure, the appressorium, which uses turgor pressure and physical mechanical force to penetrate the epidermis of the host plant to complete its infection process and affect corn yield. If not controlled, corn leaf blight can cause serious plant losses and reduced yields.

[0010] Helminthosporium maydis is a fungal pathogen that causes corn leaf spot disease in corn. It mainly harms corn leaves, but can also affect sheaths, bracts, and ears. It can occur throughout the growth period of corn, with the disease being most severe during the tasseling and grain filling stages. If not controlled, corn leaf spot disease can lead to serious plant losses and reduced yields.

[0011] Colletotrichum gloeosporioides is a fungal pathogen that causes anthracnose on apples, primarily affecting the fruit, but also mosses and branches. In addition to apples, it can also infect a variety of fruit trees, including crabapples, pears, grapes, peaches, walnuts, hawthorns, persimmons, dates, chestnuts, citrus, litchis, and pears, as well as trees such as Robinia. If not controlled, apple anthracnose can lead to severe plant losses and reduced yields.

[0012] Colletotrichum truncatum is a fungal pathogen that causes anthracnose on soybeans. The disease can occur from the seedling stage to the mature stage, and cotyledons, leaves, petioles, stems, pods and seeds can all be affected. Soybean anthracnose is one of the important diseases in soybean producing areas around the world. If it is not controlled, it can cause serious soybean yield reduction.

[0013] Pythium deliense Meurs is an oomycete pathogen that causes cottony rot on peppers. This disease causes rot at the base of seedlings, constriction and sudden death. In the adult stage, it mainly harms the fruit. The diseased part of the fruit is brown and wet rot. When the humidity is high, a dense white flocculent mold layer grows on the diseased part. In severe cases, the entire fruit becomes sick and finally rots. If not controlled, cottony rot of pepper can cause serious plant losses and reduced yields.

[0014] Puccinia striiformis is a fungal pathogen that causes stripe rust on wheat. The disease can occur from the emergence of wheat to maturity, mainly affecting leaves, followed by leaf sheaths and stems, and also infecting spikes, husks and awns. Wheat stripe rust is one of the most important wheat diseases worldwide and an important biological disaster affecting China's wheat production safety. In epidemic years, it can cause a 40% reduction in wheat production or even a total crop failure.

[0015] Puccinia polysora Underw is a fungal pathogen that causes southern corn rust, which occurs primarily on corn leaves but can also infect sheaths, stems, and bracts. If not controlled, southern corn rust can cause severe plant losses and reduced yields.

[0016] Gymnosporangiumharaeanum Syd. is a fungal pathogen that causes rust on pear trees. It mainly harms leaves and new shoots. In severe cases, it also harms young fruits, petioles and fruit stalks. Pear rust is an important disease of pear trees. In severe years, the diseased leaf rate of pear trees in some pear orchards is more than 60%. If not controlled, pear rust can cause serious plant losses and reduced yields.

[0017] Pseudoperonospora cubensis is an oomycete pathogen that causes cucumber downy mildew. If left uncontrolled, cucumber downy mildew can lead to severe plant losses and reduced yields.

[0018] Erysiphe cichoracearum is a fungal pathogen that causes cucumber powdery mildew. It usually develops severely in the middle and late stages of growth, causing leaf dryness and even premature vine pulling. In addition to cucumbers, it can also harm zucchini, pumpkin, melon, etc. If not controlled, cucumber powdery mildew can lead to serious plant losses and reduced yields.

[0019] These diseases have an adverse effect on agricultural output, and therefore there is a need to provide effective alternatives to common practices to control or prevent these diseases in vegetables, fruits, and food plants. Therefore, the present invention further provides methods for controlling or preventing vegetables, fruits, and food plants from being infected by phytopathogenic microorganisms, which cause diseases such as wheat head blight, wheat stem base rot, rice false smut, tomato and strawberry gray mold, soybean phytophthora, pepper phytophthora, potato late blight, corn leaf spot, corn leaf spot, apple and grape anthracnose, pepper cotton rot, wheat stripe rust, corn southern rust, pear rust, cucumber downy mildew, and cucumber powdery mildew.

[0020] Patents CN113683509A and CN114890899A disclose a class of diphenyl ether ester compounds of formula (II) and their preparation methods, and disclose their use in preventing and controlling rice blast on rice. However, there are no reports on methods for preventing and controlling other plant diseases using diphenyl ether ester compounds of formula (II) specifically disclosed in patents CN113683509A and CN114890899A.

[0021]

[0022] Most pathogenic fungi or oomycetes rely on asexual conidia or zoospores to achieve infection and spread of diseases. If the spore germination of pathogens can be inhibited, the infection of plants by pathogenic microorganisms can be controlled or prevented. Summary of the invention

[0023] The technical solution of the present invention to solve the above technical problems is as follows:

[0024] The present invention provides a method for controlling or preventing useful plants from being infected by plant pathogenic microorganisms, wherein the plant pathogenic microorganisms are selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chlorophyllotoxin, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia streaky, Puccinia multihelix, Puccinia pear, Pseudocorhinus cubana and Powdery Mildew fowleri, wherein the method comprises applying a compound of formula (I) or an agrochemically active salt thereof to the plant, its locus, or its propagation material.

[0025]

[0026] Preferably, the useful plants are selected from wheat, barley, rice, sorghum, oats, tomatoes, strawberries, grapes, soybeans, peppers, potatoes, corn, apples, cucumbers, melons, okra, spinach, lettuce, asparagus, cabbage, carrots, onions, peppers, pears, peaches, walnuts, hawthorns, persimmons, dates, chestnuts, citrus, litchi, zucchini, pumpkins and cotton.

[0027] More preferably, the plant pathogenic microorganism is selected from the group consisting of Fusarium graminearum, Chloroblastoma oryzae, Claviceps miltiorrhiza, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium gloeosporioides, Pythium delhiii, Puccinia multiflora, Pseudocorhinus edulis, Fusarium oxysporum, Helminthosporium convexum, Colletotrichum flatheaded, Phytophthora infestans, Puccinia streaky spores, Puccinia pears and Powdery Mildew leucoderma, and the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

[0028] More preferably, wherein the plant pathogenic microorganism is Fusarium graminearum and the plant is wheat.

[0029] The present invention also provides a use of a compound of formula (I) or an agrochemically active salt thereof for controlling or preventing useful plants from being infected by phytopathogenic microorganisms, wherein the phytopathogenic microorganisms are selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chloroblastoma oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia streaky, Puccinia multihexaenoic, Puccinia gummyars, Pseudocorhinus cubanae and Powdery Mildew fowleri.

[0030] Preferably, the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

[0031] The present invention also provides a method for growing useful plants, which comprises treating the propagation material thereof with a compound of formula (I) or an agrochemically active salt thereof, for controlling or preventing the useful plants from being infected by plant pathogenic microorganisms, wherein the plant pathogenic microorganisms are selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Green sclerotium of rice, Claviceps miltiorrhiza, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia streaky, Puccinia multihexaenoic, Puccinia gummyars, Pseudocorhinus cubanae and Powdery Mildew fowleri.

[0032] Preferably, the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

[0033] The present invention also provides the use of a compound of formula (I) or an agrochemically active salt thereof in the preparation of a medicament for controlling or preventing useful plants from being infected by phytopathogenic microorganisms, wherein the phytopathogenic microorganisms are selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chloroblastoma oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia streaky, Puccinia multihexaenoic, Puccinia gracile, Pseudocorhinus cubanae and Powdery Mildew fowleri.

[0034] Preferably, the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

[0035] Therefore, the compounds of formula (I) provide an important new solution for farmers to control or prevent vegetables, fruits, and grain plants from being infected by diseases such as wheat ergot, rice false smut, sorghum ergot, wheat stem base rot, tomato and strawberry gray mold, soybean phytophthora, pepper phytophthora, potato late blight, corn leaf blight, corn leaf blight, apple and grape anthracnose, pepper cotton rot, wheat stripe rust, corn southern rust, pear rust, cucumber downy mildew, and cucumber powdery mildew.

[0036] The compound of formula (I) is obtained by optimizing and designing on the basis of the skeleton of the compound of formula (II), and the compound of formula (II) is an inhibitor designed based on the effector protein MoErs1 unique to rice blast fungus. This target does not exist in other plant pathogenic microorganisms, and the optimized compound of formula (I) has unpredictable control effects on diseases or pathogens with large differences. It is now unexpectedly found that the compound of formula (I) can effectively control or prevent useful plants from being infected by plant pathogenic microorganisms, especially plants infected by pseudo-graminearum Fusarium, yellow Fusarium, sharp spore Fusarium, graminearum Fusarium, rice green sclerotinia, sorghum ergot, gray Botrytis cinerea, soybean phytophthora, pepper phytophthora, infestation phytophthora, convex umbilical cord worm spore, long worm spore, gloeosporium anthracnose, flat-headed anthracnose, Delhi pythium, stripe rust, multi-pile rust, pear rust, Cuban pseudoperonospora and melon powdery mildew.

[0037] The compound of formula (I) can be used as such or in the form of its agrochemically active salt. Agrochemically active salts include base addition salts of inorganic bases and organic bases, such as potassium salts, sodium salts, ammonium salts, dimethylamine salts, isopropylamine salts, and the like.

[0038] As used herein, control or controlling includes protective, curative and eradicative treatment of phytopathogenic fungi.

[0039] Application to plants should be understood as meaning application to all parts and organs of the plant above and below the ground, such as buds, leaves, needles, stems, trunks, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. It also includes application to harvested materials and asexual and sexual propagation materials, such as cuttings, tubers, rhizomes, divisions and seeds.

[0040] Plant pathogenic fungi that can be controlled according to the present invention include:

[0041] Powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaeraleucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Erysiphenecator;

[0042] Rust pathogens, such as species of the genus Gymnosporangium, such as Gymnosporangium sabinae; species of the genus Hemileia, such as Hemileia vasterrix; species of the genus Phakopsora, such as Phakopsora pachyrhizi, Phakopsora meibomiae or Phakopsora euvitis; species of the genus Puccinia, such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; species of the genus Uromyces, such as Uromyces appendiculatus;

[0043] Leaf blotch and leaf wilt pathogens: for example, Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporum species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum spp. lindemuthanium; Corynespora species, such as Corynespora cassicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoefaw cettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Ustilaginoidea species, such as Ustilaginoideavirens; Claviceps species, such as Claviceps sorghi; Magnaporthe species, such as Magnaporthe grisea; Microdochium species, such as Microdochium nivale;Species of the genus Mycosphaerella, such as Zymoseptoriatritici, Mycosphaerellaarachidicola or Mycosphaerellafijiensis; species of the genus Phaeosphaeria, such as Phaeosphaerianodorum; species of the genus Pyrenophora, such as Pyrenophorateres or Pyrenophoratriticirepentis; species of the genus Ramularia, such as Ramularia singa. collo-cygni or Ramularia areola; species of the genus Rhynchosporium, such as Rhynchosporium secalis; species of the genus Septoria, such as Septoria apii or Septorialycopersii; species of the genus Stagonospora, such as Stagonosporanodorum; species of the genus Typhula, such as Typhula incarnata; species of the genus Venturia, such as Venturia inaequalis;

[0044] Ear or panicle diseases (including corn cobs) caused by pathogens such as Alternaria spp., such as Alternaria spp.; Aspergillus spp., such as Aspergillus flavus; Cladosporium spp., such as Cladosporium cladosporioides; Claviceps spp., such as Claviceps purpurea; Fusarium spp., such as Fusarium culmorum; Gibberella spp., such as Gibberella zeae; Monographella spp., such as Monographella nivalis; Aspergillus spp., such as wheat leaf spot fungus;

[0045] Fruit rot caused by pathogens such as Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Monilinia species, such as Monilinialaxa; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Rhizopus species, such as Rhizopus stolonifer; Sclerotinia species, such as Sclerotiniasclerotiorum; Verticilium species, such as Verticilium alboatrum;

[0046] Seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by pathogens such as Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochytalentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus graminis. sativus) (conidial forms: Drechslera, Bipolaris synonym: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Macrophomina species, such as Macrophomina phaseolina; Microdochium species, such as Microdochium nivale; Monographella species, such as Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Phytophthora species, such as Phytophthora nematodea. cactorum); species of the genus Pyrenophora, such as Pyrenophora graminea; species of the genus Pyricularia, such as Pyricularia oryzae; species of the genus Pythium, such as Pythium ultimum;Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septorianodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae;

[0047] Diseases of plant tubers caused by pathogens such as Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;

[0048] Diseases of soybean leaves, stems, pods and / or seeds caused by pathogens such as Alternaria leaf spot (Alternaria spec. atranstenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercosporakikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostachys raphis), and phyllostica leaf spot (Phyllostachys raphis). spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaeradiffusa), pyrenochaeta leaf spot (Pyrenochaetaglycines, rhizoctonia aerial), foliage and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae, Phakopsora euvitis), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), target spot (Corynespora cassiicola). .

[0049] Preferably, the plant pathogenic fungi are selected from the group consisting of: snow rot, botrytis cinerea, rice pear spore, ergot, soybean shell spore, kikuchi cercaria, soybean cercaria, solani, rust fungus, yam rust fungus, mountain bean spore, gramineous Bulbus graminis, single capsule powdery mildew, grape powdery mildew fungus, solanum chain spore, beet cercaria, grape black rot fungus (Guignardiabidwellii), gray large shell, snow mold microspore, wheat leaf blight fungus, fiji spherical cavity fungus, glumen spore, round core cavity fungus, thin wheat grass core cavity fungus, Singa column spore, white spot column spore, rye beak spore, apple black spot fungus, drupe chain sclerotinia and sclerotinia.

[0050] More preferably, the plant pathogenic fungi are selected from the group consisting of pseudo-Fusarium graminearum, yellow Fusarium, sharp spore Fusarium, Fusarium graminearum, green sclerotium of rice, Botrytis cinerea, soybean phytophthora, pepper phytophthora, infestation phytophthora, convex umbilical cord worm spore, long worm spore, gloeosporium anthracnose, flat-headed anthracnose, Delhi pythium, stripe rust, multi-pile rust, pear rust, Cuban false downy mildew and melon powdery mildew. Particularly preferred is wheat scab.

[0051] Useful plants include, but are not limited to:

[0052] Vegetables or vegetable plants: including but not limited to okra, spinach, lettuce, asparagus, cabbage, carrots, onions, peppers, hot peppers, bell peppers, cucumbers, corn, lettuce, asparagus, cabbage, tomatoes, squash, eggplant, and beets;

[0053] Fruits or fruit plants: including but not limited to grapes, apples, pears, peaches, hawthorns, persimmons, dates, citrus, cherries, strawberries, blueberries, oranges, lemons, grapefruits, plums, apricots, bananas, sugar cane and lychees;

[0054] Food grains or food plants: including but not limited to wheat, barley, rye, rice, oats, sorghum, soybeans and potatoes;

[0055] Oil crops: rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil plant, cocoa and peanut;

[0056] Other plants: turf, tobacco, nuts, coffee, tea, pepper, grapevines, hops, and latex plants;

[0057] Ornamental plants: flowers, shrubs, deciduous trees and conifers.

[0058] Plant pathogenic microorganisms include fungi that are resistant to other fungicides. A fungus that is "resistant" to a particular fungicide refers to a strain that is less sensitive to that fungicide, for example, than the expected sensitivity of the same species. The expected sensitivity can be measured using, for example, a strain that has not been previously exposed to the fungicide.

[0059] The above-mentioned method or purposes, preferably to plant crops, its place or its propagation material application.Preferably to the place of plant or the propagation material of plant application, more preferably to propagation material application.Application can be carried out according to any common application mode (for example leaf application, spray application, soil application, furrow irrigation application, seed treatment application etc.).

[0060] The compounds of formula (I) are preferably used for disease control at 1 to 500 g / ha, preferably 50-200 g / ha.

[0061] The compounds of formula (I) are suitable for use on any vegetable, fruit or food plant, including those useful plants which have been genetically modified to be resistant to active ingredients (such as herbicides) or those useful plants which have been genetically modified to produce biologically active compounds for controlling infection by phytopathogenic microorganisms.

[0062] Typically, the compounds of formula (I) are used in the form of a composition (eg, a formulation) containing a carrier. The compounds of formula (I) and their compositions can be used in different forms, such as aerosol sprays, capsule suspensions, cold atomization concentrates, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, hot atomization concentrates, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulv) liquids, ultra-low volume (ulv) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment and wettable powders.

[0063] The formulation typically comprises a liquid or solid carrier and optionally one or more commonly used formulation adjuvants, which may be solid or liquid adjuvants, for example, non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, adhesives and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors or other preparations that affect plant growth, and comprises combinations containing the compounds of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0064] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound according to the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound according to the invention together with one or more auxiliary agents. In the case of the solid compound according to the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0065] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric substance, the composition comprising a compound of formula (I) and the type of composition being chosen to be suitable for the intended purpose and the prevailing circumstances.

[0066] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of a compound of formula (I) and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, and in principle it is possible that 0 to 25% (especially 0.1% to 20%) of the composition is a surfactant (% means percentage by weight in each case). While for commercial products, concentrated compositions tend to be preferred, end users generally use diluted compositions with substantially lower concentrations of active ingredients.

[0067] Examples of leaf formulation types for use in premix compositions are:

[0068] GR: Granules

[0069] WP: Wettable Powder

[0070] WG: Water dispersible granules (powders)

[0071] SG: Water-soluble granules

[0072] SL: Soluble Concentrate

[0073] EC: Emulsifiable Concentrate

[0074] EW: Oil in water emulsion

[0075] ME: Microemulsion

[0076] SC: Aqueous Suspension Concentrate

[0077] CS: Aqueous Capsule Suspension

[0078] OD: Oil-based suspension concentrates, and

[0079] SE: aqueous suspension emulsion.

[0080] While examples of the types of seed treatment formulations useful in premix compositions are:

[0081] WS: Wettable powder for seed treatment slurry

[0082] LS: Solution for seed treatment

[0083] ES: Emulsion for seed treatment

[0084] FS: Suspension concentrate for seed treatment

[0085] WG: water dispersible granules, and

[0086] CS: aqueous capsule suspension.

[0087] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0088] For the properties of the formulation, the method of application (such as foliar application, spray application, atomization application, atomization application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the environment at the time. Tank mix compositions are generally prepared by diluting one or more premix compositions containing different pesticides and optionally additional adjuvants with a solvent (e.g., water).

[0089] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0090] Generally, tank-mix formulations for foliar or soil application contain 0.1% to 20%, especially 0.1% to 15%, of the desired ingredients and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0091] Typically, premix formulations for foliar application contain 0.1% to 99.9%, especially 1% to 95% of the desired ingredient and 99.9% to 0.1%, especially 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0092] Typically, tank-mix formulations for seed treatment applications contain 0.25% to 80%, especially 1% to 75%, of the desired ingredients and 99.75% to 20%, especially 99% to 25%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 40%, especially 0.5% to 30%, based on the tank-mix formulation.

[0093] Typically, premix formulations for seed treatment applications contain 0.5% to 99.9%, especially 1% to 95%, of the desired ingredients and 99.5% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0094] Whereas commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), the end user will typically use a diluted formulation (eg, a tank-mix composition).

[0095] Preferred seed treatment premix formulations are aqueous suspension concentrates. Conventional processing techniques and machines, such as fluidized bed technology, drum milling methods, rotostatic seed processors and drum coaters, can be used to apply the formulation to the seed. Other methods (such as spouted beds) may also be useful. The seeds may be pre-sized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compound of the present invention is particularly suitable for use in soil and seed treatment applications.

[0096] In general, the premix composition of the present invention contains 0.5% to 99.9%, in particular 1% to 95%, advantageously 1% to 50% by mass of the desired ingredients and 99.5% to 0.1%, in particular 99% to 5% by mass of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant (or adjuvant) may be a surfactant, in an amount of 0 to 50%, in particular 0.5% to 40%, by mass, based on the mass of the premix formulation.

[0097] Plants and plant cultivars treated with the compounds of formula (I) include plants and plant cultivars which are hybrid plants which already express the characteristic of heterosis or hybrid vigour, which generally results in greater yield, vigour, health and resistance to biotic and abiotic stresses.

[0098] Formula (I) compound can be advantageously used for treating transgenic plants, plant cultivars or plant parts that have received genetic material, which confer favorable and / or useful properties (properties) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention is combined with one or more recombinant traits or transgenic events or combinations thereof. For the purposes of this application, transgenic events are produced by inserting specific recombinant DNA molecules into specific locations (sites) of plant genome chromosomes. The insertion creates a new DNA sequence known as an "event", characterized in that the inserted recombinant DNA molecules and a certain amount of genomic DNA are adjacent to the two ends of the inserted DNA / flanking the two ends of the inserted DNA. This proterties or transgenic events include, but are not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, wherein the proterties are measured relative to plants lacking this proterties or transgenic events. Specific examples of such advantageous and / or useful properties (traits) are better plant growth, vigor, stress tolerance, stand growth ability, lodging resistance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated maturation, higher yield, higher quality and / or higher nutritional value of the harvested product, better storage life and / or processability of the harvested product, and increased resistance to animal and microbial pests (e.g. insects, arachnids, nematodes, mites, slugs and snails).

[0099] Among the DNA sequences encoding proteins which confer tolerance properties on these animal and microbial pests, in particular insects, mention will be made in particular of the genetic material consisting of the Bt protein encoding from Bacillus thuringiensis, which is widely described in the literature and is well known to those skilled in the art. Mention will also be made of proteins extracted from bacteria, such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). In particular, BtCry or VIP proteins including Cry1A, Cry1Ab, Cry1Ac, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof, as well as hybrids or combinations thereof, in particular Cry1F protein or hybrids derived from Cry1F protein (such as hybrid Cry1A-CrylF protein or toxic fragments thereof), Cry1A-type proteins or toxic fragments thereof, preferably Cry1Ac protein or hybrids derived from Cry1Ac protein (such as hybrid Cry1Ab-CrylAc protein) or Cry1Ab or Bt2 protein or toxic fragments thereof, Cry2Ae, Cry2Af or Cry2Ag protein or toxic fragments thereof, Cry1A.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton events, as described in Estruch et al. (1996), Proc Natl Acad Sci. Sci US A.28; 93 (11): 5389-94 or a toxic fragment thereof, a Cry protein described in WO2001 / 47952, an insecticidal protein from Xenorhabdus (such as described in WO98 / 50427), Serratia (especially from S. entomophila) or a Photorhabdus species strain, such as the Tc protein from Photorhabdus described in WO98 / 08932. In addition, the present invention also includes any variant or mutant of any of the above-mentioned proteins that differs from any of the above-mentioned sequences (especially the sequences of their toxic fragments) in some amino acids (1-10, preferably 1-5), or any variant or mutant of the above-mentioned protein fused with a transit peptide (such as a plastid transit peptide) or another protein or peptide.

[0100] The beneficial effect of the present invention is that the same compound has unpredictable control effects on diseases or pathogens with great differences. It has now been unexpectedly found that the compound of formula (I) has a good control or prevention effect on useful plants infected by plant pathogenic microorganisms. DETAILED DESCRIPTION

[0101] The present invention is described below in conjunction with examples, but the present invention is not limited thereto. In the art, simple replacements or improvements made by technicians to the present invention all belong to the technical solutions protected by the present invention. The endpoints and any values ​​of the ranges disclosed in this article are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be regarded as specifically disclosed in this article.

[0102] Several methods for preparing the compounds of formula (I) of the present invention have been disclosed in CN113683509A, which is incorporated herein by reference. The raw materials can be purchased from the market or can be prepared by methods known in the literature. It will be appreciated by those skilled in the art that other synthetic routes can also be used to synthesize the compounds of the present invention.

[0103] All plant pathogenic microorganisms in the biological examples were from strains stored at 4°C in the laboratory of the College of Plant Protection of Nanjing Agricultural University.

[0104] Water agar medium: add 20 g agar to 1000 mL of distilled water, stir to fully dissolve, divide into 200 mL Erlenmeyer flasks, sterilize at 121°C for 20 minutes, and set aside after cooling.

[0105] PDA medium (potato agar glucose medium): wash and peel 200g of potatoes, cut into small pieces, boil them in boiling water (boil for 30 minutes), filter with four layers of gauze, remove the residue, add 20g of glucose, then add 20g of agar, add double distilled water to make up to 1000mL, stir to fully dissolve, divide into 200mL Erlenmeyer flasks, sterilize at 121℃ for 20 minutes, cool and set aside.

[0106] V8 medium (10%): add 1g CaCO3 to 100mL V8 juice, centrifuge at 2500rpm for 5min, dilute the supernatant with double distilled water at a ratio of 1:9 (v / v). If preparing solid culture medium, add 15g agar powder to 1L diluted solution, sterilize at 121℃ for 20min, and cool for later use.

[0107] PDAG culture medium: Wash and peel 200g of potatoes, cut into small pieces, boil them in boiling water (boil for 30 minutes), filter with four layers of gauze, remove the residue, add 20g of mannitol, then add 20g of agar, make up to 1000mL with double distilled water, stir to fully dissolve, divide into 200mL Erlenmeyer flasks, sterilize at 121℃ for 20 minutes, and set aside after cooling.

[0108] Antibacterial concentration EC 50The values, toxicity regression equations and correlation coefficients were calculated by the DPS data processing system: the actual test concentration and the corresponding spore germination inhibition rate were input, quantitative biological machine value analysis was used, the measurements were converted into logarithmic units, and the lethal mortality value was set to 50 to obtain the required data.

[0109] The following examples are provided to facilitate further understanding of the preparation method of the present invention, and the specific substances, types and conditions used are determined to further illustrate the present invention and are not intended to limit its reasonable scope. All cited documents are incorporated by reference.

[0110] Preparation Example 1 (SC)

[0111] 10 parts of the compound of formula (I) (content> 95%), 6 parts of wetting agent SP-SC3266E, 4 parts of ethylene glycol, 0.35 parts of xanthan gum, 0.2 parts of kason, 0.2 parts of defoaming agent, 79.25 parts of water were uniformly mixed, sheared, stirred, and sand-milled to obtain an aqueous suspension concentrate with 10% of the active ingredient.

[0112] Biological Example 1: Fusarium graminearum (Wheat Gibberella) on wheat

[0113] The spore germination assay was performed as follows: 100 mg of the compound of formula (I) (content> 95%) was dissolved in 10 mL of DMSO to prepare a 10000 μg / mL stock solution; different doses of the stock solution were added to PDA medium, diluted to different concentrations as shown in Table 1, and the plates were inverted. The concentration of the conidia suspension was 1×10 5 / mL, and evenly spread it on plates of different concentrations with a coating rod. 50μL of spore suspension was dropped onto each PDA plate, and evenly spread with a sterilized glass rod, and inverted at 25°C to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reached about 95%, the investigation began, and all plates were placed at 0°C. During the investigation, 200 spores were counted in each field of view under a microscope (the field of view was not repeated), and the germination rate of each treatment (the number of germinated spores / 200) was recorded; the experiment was repeated three times and the average value was taken. The inhibition of spore germination by the compound of formula (I) is shown in Tables 1 and 2.

[0114] Table 1 Inhibition rate of spore germination of Fusarium graminearum by compounds of formula (I) (%)

[0115] 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 9.3 30.2 44.7 Carbendazim 7.3 23.3 36.2 Cyanostrobin 8.1 26.7 39.6

[0116] Table 2 Inhibitory activity of compounds of formula (I) against spore germination of Fusarium graminearum

[0117] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=3.6723+1.1824x 0.9997 13.2730 Carbendazim y=3.5377+1.0895x 0.9990 21.9896 Cyanostrobin y=3.5985+1.1305x 0.9999 17.3696

[0118] Biological Example 2: Botrytis cinerea (Tomato Gray Mold) on Tomatoes

[0119] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 3. The medium used for coating the spore suspension was water agar medium, and the concentration of the spore suspension was 1×10 5 / mL. Drop 50μL of spore suspension on each water agar medium plate, spread it evenly with a sterilized glass rod, invert and culture at 25℃, and track the spore germination process of the drug-free plate. When the spore germination rate of the drug-free plate reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment; the experiment is repeated three times and the average value is taken.

[0120] Table 3 Inhibition rate of spore germination of Botrytis cinerea by compounds of formula (I) (%)

[0121] 2 μg / mL 10 μg / mL 20 μg / mL Compound of formula (I) 10.6 39.3 60.5 Pyraclostrobin 22.6 56.1 72.9 Procymidone 17.1 48.3 69.2 Pyrimethanil 10.4 35.1 58.2

[0122] Table 4 Inhibitory activity of compounds of formula (I) against spore germination of Botrytis cinerea

[0123] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=3.2866+1.4937x 0.9982 14.029 Pyraclostrobin y=3.8326+1.3502x 0.9993 7.3212 Procymidone y=3.6005+1.4248x 0.9966 9.6007 Pyrimethanil y=3.2826+1.4287x 0.9936 15.9250

[0124] Biological Example 3: Phytophthora sojae (Phytophthora sojae) on soybeans

[0125] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a stock solution of 10000 μg / mL, and the drug concentration treatment was set as shown in Table 5. The medium used for coating the zoospore suspension was V8 medium, and the concentration of the spore suspension was 1×10 5 / mL. 50μL of spore suspension was dropped onto each V8 medium (10%) plate, spread evenly with a sterilized glass rod, and inverted at 25°C to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reached about 95%, the investigation began and all plates were placed at 0°C. During the investigation, 200 spores were counted in each field of view under a microscope (the field of view was not repeated), and the germination rate of each treatment was recorded; the experiment was repeated three times and the average value was taken.

[0126] Table 5 Inhibition rate of spore germination of fungi by compounds of formula (I) (%)

[0127] 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 30.1 46.2 50.1 Metalaxyl 9.2 31.6 53.3 Dimethomorph 60.2 89.3 96.1

[0128] Table 6 Inhibitory activity of compounds of formula (I) against spore germination of Phytophthora sojae

[0129] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=4.4865+0.5389x 0.9932 8.971 Metalaxyl y=3.6454+1.3769x 0.9941 9.6350 Dimethomorph y=5.2457+1.4870x 0.9988 0.6835

[0130] Biological Example 4: Phytophthora capsici (Phytophthora capsici) on peppers

[0131] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 7. The medium used for coating the zoospore suspension was V8 medium, and the concentration of the spore suspension was 1×10 5 / mL. 50μL of spore suspension was dropped onto each V8 medium (10%) plate, spread evenly with a sterilized glass rod, and inverted at 25°C to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reached about 95%, the investigation began and all plates were placed at 0°C. During the investigation, 200 spores were counted in each field of view under a microscope (the field of view was not repeated), and the germination rate of each treatment was recorded; the experiment was repeated three times and the average value was taken.

[0132] Table 7 Inhibition rate of spore germination of Phytophthora capsici by compounds of formula (I) (%)

[0133] 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 16.3 44.6 62.4 Metalaxyl 13.6 40.1 61.3 Dimethomorph 51.1 78.3 88.7

[0134] Table 8 Inhibitory activity of compounds of formula (I) against spore germination of Phytophthora capsici

[0135] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=4.0062+1.2828x 0.9986 5.9526 Metalaxyl y=3.8785+1.3552x 0.9953 6.7230 Dimethomorph y=5.0138+1.1650x 0.9977 0.9731

[0136] Biological Example 5: Phytophthora infestans (Phytophthora infestans) on potatoes

[0137] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 9. The medium used for coating the spore suspension was V8 medium, and the concentration of the spore suspension was 1×10 5 / mL. 50μL of spore suspension was dropped onto each V8 medium (10%) plate, spread evenly with a sterilized glass rod, and inverted at 25°C to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reached about 95%, the investigation began and all plates were placed at 0°C. During the investigation, 200 spores were counted in each field of view under a microscope (the field of view was not repeated), and the germination rate of each treatment was recorded; the experiment was repeated three times and the average value was taken.

[0138] Table 9 Inhibition rate of spore germination of Phytophthora infestans by compounds of formula (I) (%)

[0139] 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 12.6 34.7 54.1 Metalaxyl 9.8 32.6 52.3 Fluopyram 13.4 37.3 56.1 Dimethomorph 40.3 77.6 89.2

[0140] Table 10 Inhibitory activity of compounds of formula (I) against spore germination of Phytophthora infestans

[0141] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=3.8315+1.2181x 0.9942 9.1052 Metalaxyl y=3.6875+1.3250x 0.9965 9.7850 Fluopyram y=3.8737+1.2365x 0.9963 8.1443 Dimethomorph y=4.7483+1.4747x 0.9997 1.4814

[0142] Biological Example 6: Helminthosporium (Microsporum maydis) on corn

[0143] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 11. The medium used for coating the spore suspension was PDAG medium, and the concentration of the spore suspension was 1×10 5 / mL. Drop 50μL of spore suspension on each PDAG medium plate, spread it evenly with a sterilized glass rod, invert and culture at 25℃, and track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment; the experiment is repeated three times and the average value is taken.

[0144] Table 11 Inhibition rate of spore germination of Helminthosporium by compounds of formula (I) (%)

[0145]

[0146]

[0147] Table 12 Inhibitory activity of compounds of formula (I) against spore germination of Helminthosporium

[0148] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=4.6499+0.5106x 0.9989 4.850 Tebuconazole y=4.4263+0.6524x 0.9949 7.5753 Pyraclostrobin y=4.6859+1.0235x 0.9980 2.0273

[0149] Biological Example 7: Colletotrichum gloeosporioides (Apple Anthracnose) on Apples

[0150] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 13. The medium used for coating the spore suspension was PDA medium, and the concentration of the spore suspension was 1×10 5 / mL. Drop 50μL of spore suspension on each PDA medium plate, spread it evenly with a sterilized glass rod, invert and culture at 25℃, and track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment; the experiment is repeated three times and the average value is taken.

[0151] Table 13 Inhibition rate of spore germination of Colletotrichum gloeosporioides by compounds of formula (I) (%)

[0152] 2 μg / mL 10 μg / mL 20 μg / mL Compound of formula (I) 22.1 49.1 62.8 Prochloraz 19.8 45.2 59.9 Difenoconazole 37.2 65.1 77.9

[0153] Table 14 Inhibitory activity of compounds of formula (I) against spore germination of Colletotrichum gloeosporioides

[0154] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=3.8992+1.0905x 0.9998 10.2196 Prochloraz y=3.8156+1.0894x 0.9992 12.2249 Difenoconazole y=4.3378+1.0825x 0.9987 4.0897

[0155] Biological Example 8: Pythium delirium (Pepper Rot) on Peppers

[0156] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a stock solution of 10000 μg / mL, and the drug concentration treatment was set as shown in Table 15. The medium used for coating the spore suspension was water agar medium, and the concentration of the spore suspension was 1×10 5 / mL. 50μL of spore suspension was dropped onto each V8 medium (10%) plate, spread evenly with a sterilized glass rod, and inverted at 25°C to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reached about 95%, the investigation began and all plates were placed at 0°C. During the investigation, 200 spores were counted in each field of view under a microscope (the field of view was not repeated), and the germination rate of each treatment was recorded; the experiment was repeated three times and the average value was taken.

[0157] Table 15 Inhibition rate of spore germination of compounds of formula (I) against Pythium deliciosa (%)

[0158] 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 73.7 82.2 91.1 Fluoxazolidinone 45.6 66.2 76.2 Procymidone 43.6 58.5 71.2

[0159] Table 16 Inhibitory activity of compounds of formula (I) against spore germination of Pythium delhiensis

[0160]

[0161]

[0162] Biological Example 9: Pseudomonas graminearum and Fusarium erythrorhizium (wheat stem rot fungus) on wheat

[0163] The spore germination assay was used: 100 mg of the compound of formula (I) (content> 95%) was dissolved in 10 mL of DMSO to prepare a 10000 μg / mL stock solution; different doses of the stock solution were added to PDA medium, diluted to different concentrations as shown in the table, and the plates were inverted. The concentration of the conidia suspension was 1×10 5 / mL, and evenly spread it on plates of different concentrations with a spreading rod. Drop 50μL of spore suspension on each PDA plate, spread it evenly with a sterilized glass rod, and invert it at 25℃ to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment (number of germinated spores / 200); the experiment is repeated three times and the average value is taken.

[0164] The results showed that the compound of formula (I) had excellent antibacterial effect on Fusarium graminearum and Fusarium erythrorhizium.

[0165] Biological Example 10: Fusarium oxysporum (cotton wilt pathogen) on cotton

[0166] The spore germination assay was used: 100 mg of the compound of formula (I) (content> 95%) was dissolved in 10 mL of DMSO to prepare a 10000 μg / mL stock solution; different doses of the stock solution were added to PDA medium, diluted to different concentrations as shown in the table, and the plates were inverted. The concentration of the conidia suspension was 1×10 5 / mL, and evenly spread it on plates of different concentrations with a spreading rod. Drop 50μL of spore suspension on each PDA plate, spread it evenly with a sterilized glass rod, and invert it at 25℃ to track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment (number of germinated spores / 200); the experiment is repeated three times and the average value is taken.

[0167] The results showed that the compound of formula (I) had excellent antibacterial effect on Fusarium oxysporum

[0168] Biological Example 11: Helminthosporium umbellatum (Umbelliferae of Zea mays) on corn

[0169] The spore germination assay was used: the compound of formula (I) was diluted with DMSO to a 10000 μg / mL stock solution, and the drug concentration treatment was set as shown in Table 11. The medium used for coating the spore suspension was PDAG medium, and the concentration of the spore suspension was 1×10 5 / mL. Drop 50μL of spore suspension on each PDAG medium plate, spread it evenly with a sterilized glass rod, invert and culture at 25℃, and track the spore germination process of the drug-free plate (0μg / mL). When the spore germination rate of the drug-free plate (0μg / mL) reaches about 95%, start the investigation and place all plates at 0℃. During the investigation, count 200 spores in each field of view under a microscope (the field of view is not repeated), and record the germination rate of each treatment; the experiment is repeated three times and the average value is taken.

[0170] The results showed that the compound of formula (I) had an excellent antibacterial effect on Helicospora convexum.

[0171] summary:

[0172] From the above biological examples, it can be seen that the antibacterial activity of the compound of formula (I) against Fusarium graminearum is better than that of the commercial standard agents carbendazim and cyproconazole; the antibacterial activity against Botrytis cinerea is better than that of the commercial standard agent pyrimethanil; the antibacterial activity against Phytophthora sojae and Phytophthora capsici is better than that of the commercial standard agent metalaxyl; the antibacterial activity against Phytophthora infestans is comparable to that of the commercial standard agents metalaxyl and fluazifop; the antibacterial activity against Helminthosporium is better than that of the commercial standard agent tebuconazole; the antibacterial activity against Colletotrichum gloeosporioides is better than that of the commercial standard agent prochloraz; the antibacterial activity against Pythium deliciosa is better than that of the commercial standard agents fluazifop and procymidone. It can be seen that the compound of formula (I) has a significant inhibitory effect on the germination of most pathogenic fungi or oomycetes spores, and has the effect of controlling or preventing plants from being infected by pathogenic microorganisms.

[0173] Biological Example 12: Fusarium graminearum on wheat (causing wheat head blight)

[0174] In the spray chamber, wheat (cultivar Zhengmai 0943) at the flowering stage was sprayed with the compound of formula (I) prepared in Preparation Example 1 and the control agents (tebuconazole, cyanobacterium methyl and carbendazim). 5 The inoculated test plants were inoculated with a suspension of 20 seedlings / mL, with 20 seedlings in each control and treatment group. The inoculated test plants were cultured in a greenhouse at 25°C and 95% relative humidity. 7-14 days after the application of the pesticide, the number of diseased ears of each plant was counted, and the inhibition rate was calculated, inhibition rate = (the average number of diseased ears in the control group - the average number of diseased ears in the treatment group) / the average number of diseased ears in the control group.

[0175] Table 17 Inhibition rate of compounds of formula (I) on wheat scab (%)

[0176]

[0177]

[0178] Biological Example 13: Colletotrichum flatheadensis on soybeans (causing soybean anthracnose)

[0179] In a spray chamber, soybean (cultivar Hefeng 47) at the 3-leaf seedling stage was sprayed with the compound of formula (I) prepared in Preparation Example 1 and control agents (prochloraz, difenoconazole and carbendazim). 5 The inoculated test plants were inoculated with a suspension of 20 seedlings / mL, with 20 seedlings in each control and treatment group. The inoculated test plants were cultured in a greenhouse at 90% relative humidity, and when appropriate levels of lesions appeared on the untreated control plants (7-14 days after application), the leaf disease area was counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0180] Table 18 Inhibition rate of compounds of formula (I) on soybean anthracnose (%)

[0181] 0μg / mL 10 μg / mL 100 μg / mL 200 μg / mL 500 μg / mL Compound of formula (I) 0 21.6 53.3 69.8 87.6 Prochloraz 0 23.3 50.8 68.6 85.6 Difenoconazole 0 33.6 65.2 77.9 90.3 Carbendazim 0 13.9 41.3 62.1 76.2

[0182] Table 19 Inhibitory activity of compounds of formula (I) against soybean anthracnose

[0183] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=3.1245+1.0316x 0.9910 65.7711 Prochloraz y=3.1610+1.0243x 0.9815 62.4367 Difenoconazole y=3.5296+0.9896x 0.9910 30.6117 Carbendazim y=2.8067+1.0612x 0.9917 116.6434

[0184] Biological Example 14: Phytophthora infestans on potatoes (causing potato late blight)

[0185] In a spray chamber, potatoes (cultivar Favorita) at the seedling stage were sprayed with the compound of formula (I) prepared in Preparation Example 1 and the control agent (metalaxyl, fluopyram and dimethomorph). They were inoculated by dropping a suspension of zoospores (50 / μL) 24 hours after application, with 20 seedlings in each control and treatment group. The inoculated test plants were cultured in a greenhouse at 90% relative humidity, and when appropriate levels of lesions appeared on the untreated control plants (7-14 days after application), the leaf disease area was counted and the inhibition rate was calculated, inhibition rate = (leaf disease area of ​​the control group - leaf disease area of ​​the treatment group) / leaf disease area of ​​the control group.

[0186] Table 20 Inhibition rate of the compound of formula (I) on potato late blight (%)

[0187] 0μg / mL 0.2 μg / mL 1 μg / mL 2 μg / mL 4 μg / mL Compound of formula (I) 0 26.5 60.2 75.3 89.7 Metalaxyl 0 23.8 60.1 72.4 87.2 Fluopyram 0 29.1 63.4 77.8 91.3 Dimethomorph 0 16.8 42.8 58.3 72.9

[0188] Table 21 Inhibitory activity of compounds of formula (I) against potato late blight

[0189] Virulence regression equation Correlation coefficient <![CDATA[EC 50 (μg / mL)]]> Compound of formula (I) y=5.3221+1.4235x 0.9953 0.5939 Metalaxyl y=5.2474+1.3918x 0.9978 0.6641 Fluopyram y=5.4060+1.4345x 0.9950 0.5211 Dimethomorph y=4.8576+1.2019x 0.9989 1.3136

[0190] Biological Example 15: Puccinia striata on wheat (causing wheat stripe rust)

[0191] In a spray chamber, wheat (cultivar Zhengmai 0943) at the 3-leaf seedling stage was sprayed with the compound of formula (I) prepared in Preparation Example 1 and the control agent (pyraclostrobin and difenoconazole). By spraying spores (1×10 5 The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of disease appeared on untreated control plants (7-14 days after application), the leaf disease areas were counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0192] Table 22 Inhibition rate of compounds of formula (I) on wheat stripe rust (%)

[0193] 0μg / mL 0.2 μg / mL 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 0 26.5 62.9 78.3 89.7 Pyraclostrobin 0 23.8 61.1 76.4 87.2 Difenoconazole 0 29.1 63.4 80.8 91.3

[0194] Biological Example 16: Pseudocoperonospora edulis on cucumbers (causing cucumber downy mildew)

[0195] In a spray chamber, cucumber leaves (cultivar Huai'an) at the 4-leaf seedling stage were sprayed with the compound of formula (I) prepared in Preparation Example 1 and the control agents (cyazofamid, dimethomorph and carbendazim). The spores (1×10 5 The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of lesions appeared on untreated control plants (7-14 days after application), the leaf disease areas were counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0196] Table 23 Inhibition rate of compounds of formula (I) on cucumber downy mildew (%)

[0197] 0μg / mL 0.2 μg / mL 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 0 28.1 50.6 62.8 80.7 cyanazole 0 33.5 60.2 77.3 88.4 Dimethomorph 0 25.8 51.3 70.1 82.9 Carbendazim 0 21.6 40.7 56.3 68.4

[0198] Biological Example 17: Powdery mildew of cucumber (causing cucumber powdery mildew)

[0199] In the spray chamber, cucumber leaves (cultivar Huai'an cucumber) at the 4-leaf seedling stage were sprayed with the compound of formula (I) prepared in Preparation Example 1 and the control agents (tebuconazole, fluphenazine and carbendazim). Conidia (1×10 5The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of lesions appeared on untreated control plants (7-14 days after application), the leaf disease areas were counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0200] Table 24 Inhibition rate of the compound of formula (I) on cucumber powdery mildew (%)

[0201] 0μg / mL 0.2 μg / mL 1 μg / mL 5 μg / mL 10 μg / mL Compound of formula (I) 0 24.8 48.5 62.3 73.2 Tebuconazole 0 22.6 46.3 58.6 70.1 Fluorophenyl ether amide 0 33.9 56.2 70.1 81.3 Carbendazim 0 14.3 27.9 41.9 59.4

[0202] Biological Example 18: Pyrus pyrifolia on pear trees (causing pear pyrifolia)

[0203] In a spray chamber, the compound of formula (I) prepared in Preparation Example 1 and the control agent (pyraclostrobin and difenoconazole) were sprayed on leaves of pear trees of appropriate age, pear cultivar: Sucui No. 1. By spraying spores (1×10 5 The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of disease appeared on untreated control plants (7-14 days after application), the leaf disease area was counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0204] The results showed that the compound of formula (I) had excellent control effect on pear rust.

[0205] Biological Example 19: Rhizoctonia solani on rice (causing rice false smut)

[0206] In a spray chamber, the compound of formula (I) prepared in Preparation Example 1 and the control agent (tebuconazole and difenoconazole) were sprayed on rice ears of appropriate age. The rice cultivar was Liangyoupeijiu. The spores (1×10 5 The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of disease appeared on untreated control plants (7-14 days after application), the ear diseased area was counted and the inhibition rate was calculated, inhibition rate = (control group ear diseased area - treatment group ear diseased area) / control group ear diseased area.

[0207] The results showed that the compound of formula (I) had excellent protective effect against rice false smut.

[0208] Biological Example 20: Ergot fungus on sorghum (causing sorghum ergot disease)

[0209] In the spray chamber, the compound of formula (I) prepared in Preparation Example 1 and the control agent (pyraclostrobin and difenoconazole) were sprayed on the leaves of sorghum of appropriate age, sorghum cultivar: Liangnuo No. 1. By spraying spores (1×10 5 The inoculated test plants were cultured in a greenhouse at 25°C and 90% relative humidity, and when appropriate levels of disease appeared on untreated control plants (7-14 days after application), the leaf disease area was counted and the inhibition rate was calculated, inhibition rate = (control group leaf disease area - treatment group leaf disease area) / control group leaf disease area.

[0210] The results showed that the compound of formula (I) had excellent preventive effect on ergot disease in sorghum.

[0211] Biological Example 21

[0212] In 2023, a wheat field trial was conducted at Baimahu Farm in Huai'an City, Jiangsu Province, China to evaluate the effects of different compounds against wheat head blight caused by Fusarium graminearum. The compound of formula (I) was prepared into 10% SC in Formulation Example 1, 43% tebuconazole SC was purchased from Shandong Bainongsida Biotechnology Co., Ltd., 30% prothioconazole OD was purchased from Anhui Jiuyi Agriculture Co., Ltd., and 45% prochloraz EW was purchased from Zibo Hengsheng Pesticide Co., Ltd.

[0213] The spray was applied to the wheat ears at the early flowering stage using a boom sprayer with a flat fan nozzle. The first application was on April 22; the second application was on April 28. 180m per plot 2 , no repetition. Each treatment has a total of 180m 2 = 0.27 mu. Weather conditions during application: cloudy, maximum temperature 15℃, northeast wind level 4, gust level 7.

[0214] The disease occurred in early May, and the severity of the disease was assessed on May 18, 2023.

[0215] Methodology:

[0216] Sampling was conducted at 3 points in each plot, and 200 ears were surveyed at each point to investigate the severity and disease rate of each ear; the disease index and control effect were calculated.

[0217] Grading Standard:

[0218] Grade 0: No disease;

[0219] Level 1: The length of the lesion is less than 25% of the entire ear axis length;

[0220] Level 2: The length of the lesion accounts for 25-50% of the length of the entire ear axis;

[0221] Level 3: The length of the lesion accounts for 50-75% of the length of the entire ear axis;

[0222] Level 4: The length of the lesion accounts for more than 75% of the length of the entire ear axis.

[0223] Disease index = ∑ (number of diseased leaves at each level × relative level value) / (total number of panicles surveyed × 9) × 100

[0224] Control effect (%) = (blank control disease index - treatment area disease index) / blank control disease index × 100

[0225] Test location:

[0226] Experimental location sowing crop variety Resistance Status Huaian Baimahu Farm November 28, 2022 wheat Precious Wheat 3# Susceptible

[0227] Treatment List - Field Trial:

[0228]

[0229] Targets and crops in the trial:

[0230] common name Latin name Target Fusarium graminearum Fusarium graminearum crop wheat Triticum aestivumL.

[0231] Test layout:

[0232] Test Method Field trials Experimental Design Then complete block Area <![CDATA[180m 2 ]]>

[0233] Application details:

[0234] Date of application April 22, 2023, April 28, 2023 Application type Boom sprayer with flat fan nozzles Application method Spray on wheat ears in early flowering stage Slurry volume 450L / ha Treatment applied Medicinal water spray

[0235] Evaluation of prevention effectiveness:

[0236]

[0237] in conclusion:

[0238] The control effect of the compound of formula (I) on wheat scab, soybean anthracnose, potato late blight, wheat stripe rust, cucumber downy mildew and cucumber powdery mildew is better than or equivalent to the commercial standard agent. The compound of formula (I) shows very good activity against Fusarium graminearum on wheat at a rate of 150 g ai / ha, with a control effect of more than 65%, which is equivalent to the control effect of 180 g ai / ha tebuconazole and higher than the control effect of 300 g ai / ha prochloraz. Within 30 days after application, the compound of formula (I) shows a lasting control effect on wheat scab, which is equivalent to the lasting effect period of tebuconazole and prothioconazole, and is longer than prochloraz.

[0239] Biological Example 22: Effect of Compounds on Inhibiting DON Toxin Secreted by Fusarium graminearum on Wheat

[0240] Determination method of vomitoxin (DON):

[0241] The Elisa test kit used in the examples was purchased from Sevi Technology (Cat. No.: wsz0396):

[0242] 1 ELISA plate pre-coated with DON antigen (12 wells × 8 strips);

[0243] DON standard solution: 5 bottles (1mL / bottle), the contents are: 0ppb, 5ppb, 15ppb, 45ppb, 135ppb

[0244] 1x sample diluent: 1 bottle (50ml, use directly);

[0245] 10x concentrated washing solution: 1 bottle (40mL);

[0246] Enzyme marker: 1 bottle (7 mL);

[0247] Antibody working solution: 1 bottle (7 mL);

[0248] Color developing solution: 1 bottle (15mL);

[0249] Stop solution: 1 bottle (8 mL);

[0250] 2M H2SO4 (for adjusting sample pH): 1 bottle (2mL / bottle);

[0251] On May 22, 2023, wheat samples from each plot in Biological Example 21 were collected to measure the content of vomitoxin (DON) in the wheat grains to evaluate the effect of the compound in inhibiting the DON toxin secreted by Fusarium graminearum on wheat.

[0252] Sampling method:

[0253] The plot not treated with the drug in Biological Implementation 21 was used as the control group, and the plot treated with 10% SC of the compound of formula (I), 43% tebuconazole SC, 30% prothioconazole OD and 45% prochloraz EW was used as the treatment group. Samples were taken at 3 points in each plot, 200 ears were surveyed at each point, 10 g of wheat grains were collected from each ear, and crushed to pass through a 20-mesh sieve.

[0254] Detection method:

[0255] Take 1g of crushed sample, add 20mL of water and mix well, shake thoroughly for 3min, centrifuge at 4000rpm for 5min at room temperature, or filter with quantitative analysis filter paper, take 0.5mL of supernatant after centrifugation or filtrate after filtration and add it to 0.5mL of sample dilute solution for dilution and mix thoroughly. Adjust the pH value of the diluted liquid to between 6-8, and take 50μL of the diluted liquid for testing.

[0256] Take out the required reagents and microplates and place them at room temperature for more than 30 minutes. Liquid reagents must be shaken well before use, and the washing working solution must also be warmed up before use.

[0257] Number the samples and standards in the corresponding microwells, make 2 parallel wells for each sample and standard, and record the positions of the standard wells and sample wells. Add 50μL of standard / sample to the corresponding microwells, add 50μL / well of marker, and then add 50μL / well of antibody working solution, gently shake and mix, cover the plate with a cover film and bring to room temperature, and react in the dark for 15min. Carefully remove the cover film, wash thoroughly with washing working solution, 250μL / well, wash the plate 3 times, each time with an interval of 15s, pat dry with absorbent paper, add 100μL / well of color development solution, gently shake and mix, cover the plate with a cover film and bring to room temperature, and react in the dark for 5min. Add 50μL / well of stop solution, gently shake and mix, and set the microplate reader (Synergy H1, Biotek) to read the OD value of each well at 450nm.

[0258] Result analysis:

[0259] The average value (B) of the measured absorbance of the standard solution or sample is divided by the absorbance (B0) value of the first standard solution (0 standard) and then multiplied by 100% to obtain the percentage absorbance value.

[0260] Percent absorbance value (B / B0) × 100%

[0261] The standard curve is drawn with the logarithm of the standard concentration as the base 10 as the X-axis and the percentage absorbance as the Y-axis. The percentage absorbance of the sample is substituted into the standard curve, and the value corresponding to the sample is read from the standard curve as a power of 10 and multiplied by the dilution factor to obtain the amount of vomitoxin contained in the sample.

[0262] The results showed that the compound of formula (I) could inhibit the DON toxin secreted by Fusarium graminearum on wheat and reduce the DON toxin content in wheat grains.

Claims

1. A method for controlling or preventing useful plants from being infected by phytopathogenic microorganisms selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chlorotrichum oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delirium, Puccinia striatum, Puccinia multihelix, Puccinia pear, Pseudocorhinus cubana and Powdery Mildew icerariae, the method comprising applying to the plants, their loci, or their propagation materials a compound of formula (I), or an agrochemically active salt thereof, such as an alkali addition salt with an inorganic base or an organic base, more particularly a potassium salt, sodium salt, ammonium salt, dimethylamine salt, isopropylamine salt thereof:

2. The method according to claim 1, characterized in that The useful plants are selected from wheat, barley, rice, sorghum, oats, tomatoes, strawberries, grapes, soybeans, peppers, potatoes, corn, apples, cucumbers, melons, okra, spinach, lettuce, asparagus, cabbage, carrots, onions, peppers, pears, peaches, walnuts, hawthorns, persimmons, dates, chestnuts, citrus, litchis, zucchini, pumpkins and cotton.

3. The method according to claim 1, characterized in that The plant pathogenic microorganism is selected from the group consisting of Fusarium graminearum, Chloroblastoma oryzae, Claviceps sorghum, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium gloeosporioides, Pythium delhiii, Puccinia multiflora, Pseudocorhinus edulis, Fusarium oxysporum, Helminthosporium convexum, Colletotrichum flatheaded, Phytophthora infestans, Puccinia streaky spores, Puccinia pears and Powdery Mildew leucoderma, and wherein the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

4. The method according to claim 3, characterized in that The phytopathogenic microorganism is Fusarium graminearum or Chlorostiligosclerotium oryzae, and the useful plant is wheat or rice.

5. The method according to claims 1 to 4, characterized in that The compound of formula (I) is prepared into a drug in the form of one of emulsifiable concentrates, suspensions, wettable powders, dusts, granules, aqueous solutions, poison baits, mother solutions and mother powders; the content of the compound in the drug is 1 to 99.9999% by weight, preferably 10 to 80% by weight; when used in the drug, the effective dosage concentration is 0.1 ug / ml to 100 ug / ml, and the application amount is 1 to 500 g / ha, preferably 50-200 g / ha.

6. Use of a compound of formula (I) or an agrochemically active salt thereof for controlling or preventing useful plants from being infected by phytopathogenic microorganisms selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chloroblastoma oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia striatum, Puccinia multihelix, Puccinia pear, Pseudocorhinus cubanae and Powdery Mildew fowleri, Preferably, the agrochemically active salts are base addition salts such as inorganic bases and organic bases, more specifically potassium salts, sodium salts, ammonium salts, dimethylamine salts, isopropylamine salts thereof.

7. The use according to claim 6, wherein the plant is selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton.

8. The use according to claim 7, characterized in that The phytopathogenic microorganism is Fusarium graminearum or Chlorostiligosclerotium oryzae, and the useful plant is wheat or rice.

9. A method for growing useful plants, wherein the propagation material thereof is treated with a compound of formula (I) or an agrochemically active salt thereof to control or prevent infection of the useful plants by phytopathogenic microorganisms selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chloroblastoma oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia streaky, Puccinia multihelix, Puccinia pear, Pseudocorhinus cubanae and Powdery Mildew leucoderma; preferably, the plants are selected from the group consisting of wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton. Preferably, the agrochemically active salts are base addition salts such as inorganic bases and organic bases, more specifically potassium salts, sodium salts, ammonium salts, dimethylamine salts, isopropylamine salts thereof.

10. Use of a compound of formula (I) or an agrochemically active salt thereof in the preparation of a medicament for controlling or preventing useful plants from being infected by phytopathogenic microorganisms, wherein the phytopathogenic microorganisms are selected from the group consisting of Pseudomonas graminearum, Fusarium oxysporum, Fusarium graminearum, Chloroblastoma oryzae, Claviceps serrata, Botrytis cinerea, Phytophthora sojae, Phytophthora capsici, Phytophthora infestans, Helminthosporium convexum, Helminthosporium longum, Colletotrichum gloeosporioides, Colletotrichum flatheaded, Pythium delhiii, Puccinia striatum, Puccinia multihelix, Puccinia pear, Pseudocorhinus cubanae and Powdery Mildew fowleri, Preferably, the plant is selected from wheat, rice, sorghum, tomato, strawberry, soybean, pepper, potato, corn, apple, pear, cucumber and cotton; Preferably, the agrochemically active salts are base addition salts such as inorganic and organic bases, more specifically potassium, sodium, ammonium, dimethylamine, isopropylamine salts thereof.

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