BRPI0921831B1 - Composition, method and combined use for controlling plant diseases, as well as seed treatment agent - Google Patents

Description

Report of the Invention Patent for "COMPOSITION, METHOD AND COMBINED USE TO CONTROL PLANT DISEASES, AS A SEED TREATMENT AGENT".

TECHNICAL FIELD

The present invention relates to a composition for controlling plant diseases and a method for controlling plant diseases. BACKGROUND ART

Α-Substituted phenylacetic acid compounds (see, for example, Patent Document 1) and azol compounds (see, for example, Non-Patent Document 1) are conventionally known as active ingredients of agents for controlling plant diseases. Nevertheless, there is a continuing need for higher active agents to control plant diseases.

Patent Document 1: WO 95 / 27,693 Non-Patent Document 1: "The Pesticide Manual-14th edition" published by BCPC, ISBN: 1901396142 DESCRIPTION OF THE INVENTION

PROBLEMS TO BE SOLVED BY INVENTION

An object of the present invention is to provide a composition for controlling plant diseases and a method for controlling plant diseases, having excellent control effect for plant diseases, and so on.

MEANS FOR SOLVING PROBLEMS The present invention provides a composition for controlling plant diseases and a method for controlling plant diseases, having an improved control effect for plant diseases by combining a compound represented by the following formula (1) with a compound. of specific azol.

Specifically, the present invention considers the following constitutions.

[1] A plant disease control composition comprising, as active ingredient, a compound represented by formula (1): [Formula 1] (1) wherein X 1 represents a methyl group, a difluoromethyl group or an ethyl group; X 2 represents a methoxy group or a methylamino group; and X 3 represents a phenyl group, a 2-methylphenyl group or a 2,5-dimethylphenyl group; and at least one azol compound selected from the group consisting of bromuconazole, cyproconazole, diphenoconazole, fembuconezole, fluquinconazole, hexaconazole, imibenconazole, ipconazole, miclobutanil, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole;

[2] The composition according to [1], wherein the azole compound is at least one azole compound selected from the group consisting of bromuconazole, diphenoconazole, fluquinconazole, ipconazole, protioconazole, tetraconazole, triticonazole and metconazole;

[3] The composition according to [1] or [2], which has a weight ratio of the compound represented by formula (1) to at least one azol compound falling within the range 0.0125: 1 to 500 :1;

[4] A seed treatment agent comprising as active ingredient the compound represented by the formula (1) of [1] and at least one azole compound selected from the group consisting of bromuconazole, cyproconazole, diphenoconazole, fembuconazole, fluquinconazole, hexaconazole, imibenconazole, ipconazole, myclobutanil, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole;

[5] A plant seed treated with effective amounts of the compound represented by the formula (1) of [1] and at least one azole compound selected from the group consisting of bromuconazole, cyproconazole, diphenoconazole, fembuconazole, fluquinconazole, hexaconazole, imibenconazole, ipconazole, myclobutanyl, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole;

[6] A method for controlling plant diseases comprising applying to a plant or a place where a plant is allowed to cultivate effective amounts of the compound represented by the formula (1) of [1] and at least one azol compound selected from from the group consisting of bromuconazole, cyproconazole, diphenoconazole, fembuconazole, fluquinconazole, hexaconazole, imibenconazole, ipconazole, myclobutanil, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole; and [7] Combined use for controlling plant diseases of the compound represented by the formula (1) of [1] and at least one azole compound selected from the group consisting of bromuconazole, cyproconazole, diphenoconazole, fembuconazole, fluquinconazole, hexaconazole, imibenconazole, ipconazole, myclobutanyl, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole; and so on.

ADVANTAGE OF THE INVENTION The composition according to the present invention exhibits an excellent control effect for plant diseases.

BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by formula (1) for use in the plant disease control composition according to the present invention is described.

Examples of the compound represented by formula (1) include the following compounds.

A compound in which X1 is a methyl group, a difluoromethyl group or an ethyl group in formula (1); a compound in which X1 is a methyl group in formula (1); a compound in which X 2 is a methoxy group or a methylamino group in formula (1); a compound in which X1 is a methyl group and X2 is a methoxy group in formula (1); a compound in which X1 is a methyl group and X2 is a methylamino group in formula (1); a compound in which X 3 is a phenyl group, a 2-methylphenyl group or a 2,5-dimethylphenyl group in formula (1); a compound in which X 3 is a phenyl group or a 2,5-dimethylphenyl group in formula (1); a compound in which X1 is a methyl group, X2 is a methoxy group, and X3 is a 2,5-dimethylphenyl group in formula (1); a compound in which X1 is a methyl group, X2 is methylmino group, and X3 is a phenyl group in formula (1); and a compound in which X 1 is a methyl group, X 2 is methyl mino group, and X 3 is a 2,5-dimethylphenyl group in formula (1).

Next, specific examples of the compound represented by formula (1) are shown.

In the compound represented by formula (1), X1, X2, X3 are one of the combinations of substituents shown in table 1.

[Table 1] The compound represented by formula (1) may have isomers such as stereoisomers such as optical isomers based on an asymmetric carbon atom and tautomers, and any isomer may be contained and may be used alone or in a mixture of any isomer ratio in the present invention. The compound represented by formula (1) may be in a form of a solvate (e.g. hydrate) and may be used in a form of a solvate in the present invention. The compound represented by formula (1) may be in a form of a crystal form and / or an amorphous form, and may be used in any form in the present invention. The compound represented by formula (1) is a compound described in leaflet WO95 / 27693. For example, these compounds may be synthesized by a method described in the leaflet.

Next, the azol compound for use in the plant disease control composition according to the present invention in combination with the compound represented by the formula (1) is at least one azol compound selected from the group consisting of bromuco- nazole, cyproconazole, diphenoconazole, fembuconazole, fluquinconazole, hexaco-nazole, imibenconazole, ipconazole, myclobutanil, protioconazole, simeconazole, tetraconazole, triticonazole and metconazole. All azol compounds included in this group are well known compounds, such as those described in "The Pesticide Manual - 14th edition" published by BCPC, ISBN: 1901396142, pp, 121, 263, 323, 430, 503, 566, 596, 613, 736, 895, 953, 1007, 1088 and 689. These compounds may be obtained from commercial agents or prepared using well known methods. The azole compound is preferably bromuconazole, diphenoconazole, fluquinconazole, ipconazole, protioconazole, tetraconazole, triticonazole and metconazole.

In the composition for controlling plant diseases according to the present invention, the weight ratio of the compound represented by formula (1) to the azol compound, for example any one of bromuconazole, diphenoconazole, fluquinconazole, ipconazole, protioconazole, tetracone- zol, triticonazole and metconazole are typically in the range of 0.0125: 1 to 500: 1, preferably 0.025: 1 to 100: 1. Also, when used as a dusting powder, the range from 0.025: 1 to 40: 1 is more preferable, and when used as a seed treatment agent, the range from 0.25: 1 to 100: 1 is more preferable. preferable. The plant disease control composition according to the present invention may be a simple mixture of the compound represented by formula (1) and the azol compound. Alternatively, the plant disease control composition is typically made by mixing the compound represented by formula (1) and the azol compound with an inert carrier, and adding a surfactant and other adjuvants as necessary to the mixture. that the mixture may be formulated as an oil agent, an emulsion, a flowable agent, a wetting powder, a granulated wetting powder, a powdering agent, a granulating agent and so on. The aforementioned plant disease control composition may be used as the seed treating agent of the present invention in any form or added with other inert ingredients.

In the plant disease control composition according to the present invention, the total amount of the compound represented by the formula (1) and the azole compound, for example any one of bromucozazole, diphenoconazole, fluquinconazole, ipconazole, protioconazole, tetraconazole Triticonazole and metconazole are typically in the range of 0.1 to 99 wt%, preferably 0.2 to 90 wt%.

Examples of the solid carrier used in the formulation include fine powders or granules such as minerals such as kaolin clay, ata-pulgite clay, bentonite, montmorillonite, acidic white clay, pyrophyllite, talc, diatomaceous earth and calcite; natural organic materials such as corn husk powder and nutshell powder; synthetic organic materials such as urea; salts such as calcium carbonate and ammonium sulfate; synthetic inorganic materials such as synthetic hydrated silicon oxide; and as a liquid carrier, aromatic hydrocarbons such as xylene, alkylbenzene and methyl naphthalene; alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol ether; ketones such as acetone, cyclohexanone and iso-forone; vegetable oil such as soybean oil and cottonseed oil; petroleum aliphatic hydrocarbon, esters, dimethyl sulfoxide, acetonitrile and water.

Examples of the surfactant include anionic surfactants such as alkyl sulfate ester salts, alkylarylsulfonate salts, dialkyl sulfosucinate salts, polyoxyethylene ether alkylaryl phosphate ester salts, lignosulfonate salts and naphthalene sulfonate formaldehyde polycondensates; and nonionic surfactants such as polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers and sorbitan fatty acid esters and cationic surfactants such as alkyltrimethyl ammonium salts.

Examples of other formulation aids include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, polysaccharides such as gum arabic, alginic acid and salt thereof, CMC (carboxymethyl cellulose), xanthan gum, inorganic materials such as magnesium silicate aluminum and alumina solution, preservatives, coloring agents and stabilizing agents such as PAP (acid phosphate isopropyl) and BHT. The composition for controlling plant diseases according to the present invention is effective for the following plant diseases.

Rice diseases: blast (Magnaporthe grísea), Helminthosporium leaf spot (Cocliobolus miyabeanus), sheath plant pest (Rhizoctonia solani) and bakanae disease (Gibberella fujikuroi).

Wheat diseases: powdery mildew (Erysiphe graminis), pest of Fusarium head plants (Fusaríum graminearum, F., avenace-rum, F., culmorum, Microdochium nivale), rust (Puccinia stríiformis, P., graminis, P. , recondita), pink snow mold (Micronectríella nivale), Typhula snow pest (Typhula sp.), loose alfonsia (Ustilago trítici), jellyfish (Tilletia caries), ocellus (Pseudocercosporella herpotrichoides), leaf pustule (Mycosphaerella) graminicola), glume pustule (Stagonospora no-dorum) and yellow spot (Pyrenophora tritici-repentis).

Barley diseases: powdery mildew (Erysiphe graminis), Fusarium head pest (Fusarium graminearum, F., avena-cerum, F., culmorum, Microdochium nivale), rust (Puccinia strififormis, P., graminis, P. , hordei), loose alfonsia (Ustilago nudá), scalding (Rhyn-chosporium secalis), liquid pustule (Pyrenophora teres), spot pustule (Cochliobolus sativus), leaf stripe (Pyrenophora graminea) and rotting Rhizoctonia solani (Rhizoctonia solani) .

Corn diseases: alfonsia (Ustilago maydis), brown spot (Cochliobolus heterostrophus), copper spot (Gloeocercospora sorghi), southern plant pest (Puccinia polysora), gray leaf spot (Cer-cospora zeae-maydis) Rhizoctonia (Rhizoctonia solani).

Citrus plant diseases: melanosis (Diaporthe citri), crust (Elsinoe fawcetti), penicillium rot (Penicillium digitatum, P., italicum) and brown rot (Phytophthora parasitica, Phytophthora citrophthora).

Apple diseases: flowering plant pests (Monilinia mali), cancer (Waltz ceratosperma), powdery mildew (Podosphaera leuco-tricha), Alternaria leaf spot (Alternaria apple patotype), crust (Venturia inaequalis) , bitter rot (Colletotrichum acuta-tum), crown rot (Phytophthora cactorum), pustule (Diplocarpon mali) and ring rot (Botryosphaeria berengeriana).

Pear diseases: crust (Venturia nashicola, V., pirina), black spot (Alternaria altemata Japanese pear pathotype), plant pest (Gymnosporangium haraeanum) and Phytophtora (Phytophthora cactorum) fruit rot;

Peach diseases: brown rot (Monilinia fructicola), crust (Cladosporium carpophilum) and phomopsis rot (Phomopsis sp.).

Grape diseases: anthracnose (Elsinoe ampelina), mature rot (Glomerella cingulata), powdery mold (Uncinula necator), plant pest (Phakopsora ampelopsidis), black rot (Guignardia bidwellii) and fuzzy mold (Plasmopara viticola).

Japanese persimmon diseases: anthracnose (Gloeosporium kaki) and leaf spot (Cercospora kaki, Mycosphaerella nawae).

Gourd diseases: anthracnose (Colletotríchum lagenarium), powdery mildew (Sphaerotheca fuliginea), goose mollusc pest (Mycosphaerella melonis), Fusarium wilt (Fusaríum oxysporum), puverulent mold (Pseudthora dephoraphora pusudophora) sp.), decay (Pythium sp.) and decay of Rhizoctonia (Rhizoctonia solani) ', Tomato diseases: early plant pest (Alternaria solani), leaf mold (Cladosporíum fulvum) and late plant pest (Phytophthora infestans).

Eggplant diseases: brown spot (Phomopsis vexans) and powdery mildew (Erysiphe cichoracearum).

Cruciferous vegetable diseases: Alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae), crooked root (Plasmodiophora brassicae) and puverulent mold (Peronospora parasitica).

Welsh onion diseases: plant pests (Puccinia allii) and puverulent mold (Peronospora destructor).

Soybean diseases: purple seed spot (Cercospora kikuchi-i), sphaceloma scad (Elsinoe gyycinas), plant pod and stem pest (Diaporthe phaseolorum var. Soybean), septoria brown spot (Septoria gyycinas), eye spot frog (Cercospora sojina), rust (Phakopsora pachyrhizi), brown stem rot (Phytophthora soyae) and Rhizoctonia rot (Rhizoctonia solani).

Kidney bean diseases: anthracnose (Colletotríchum Hndemthianum).

Peanut diseases: leaf spot (Cercospora persona-ta), brown leaf spot (Cercospora arachidicola) and southern plant pest (Sclerotium rolfsii).

Garden pea diseases: powdery mildew (Erysiphe pisi) and root rot (Fusarium solani f. Sp. Pisi).

Potato diseases: early plant pest (Alternaria solani), late plant pest (Phytophthora infestans), pink putrefaction (Phytophthora erythroseptica) and powdery crust (Spongospora subterranean f. Sp. Subterranean).

Strawberry diseases: powdery mildew (Sphaerotheca humuh) and anthracnose (Glomerella cingulata).

Tea diseases: liquid bubble pest (Exobasidi-reticulatum), white crust (Elsinoe leucospila), gray pest (Pestalotiopsis sp.) And anthracnose (Colletotríchum theae-sinensis).

Tobacco diseases: brown spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotríchum taba-cum), downy mildew (Peronospora tabacina) and black stalk (Phytoph-thora nicotianae).

Rapeseed diseases: sclerotinia rot (Sclerotinia sclerotiorum) and Rhizoctonia rot (Rhizoctonia solani).

Cotton diseases: Rhizoctonia rot (Rhizoctonia solani).

Beet diseases: Cercospora leaf spot (Cer-cospora beticola), plant leaf pest (Thanatephorus cucumerís), root rot (Thanatephorus cucumerís) and Apha-nomyces (Aphanomyces coclioides) root rot.

Rose diseases: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa) and downy mildew (Peronospora sparsa).

Diseases of the asteraceous and chrysanthemum plants: fuzzy mold (Bremia lactucae), plant leaf pest (Septoría chrysanthemi-indici) and white plant pest (Puccinia horíana).

Diseases of the various groups: diseases caused by Pythium spp. (Pythium aphanidermatum, Pythium debaríanum, Pythium graminicola, Pythium irregulare, Pythium ultimum), gray mold (Botrytis cinerea) and Sclerotinia rot (Sclerotinia sclerotiorum).

Japanese radish disease: Alternaria leaf spot (Alternaria brassicicola).

Turfgrass diseases: dollar spot (Sclerotinia homeocarpa) and brown patch and large patch (Rhizoctonia solani).

Banana disease: sigatoka (Mycosphaerella fijiensis, Mycos-phaerella musicola).

Sunflower disease: shaggy mold (Plasmopara halstedii).

Seed diseases or diseases in the early stages of plant growth caused by Aspergillus genus, Penicillium genus, Fusarium genus, Gibberella genus, Trichoderma genus, Thielaviopsis genus, Rhizopus genus, Mucor genus, Corticium genus, Phoma genus, Rhizoctonia genus and Diplodia genre.

Viral diseases of various plants mediated by the genus Polymixa or the genus Olpidium and so on.

Plant diseases can be controlled by applying effective amounts of the compound represented by formula (1) and the compound (s) of azole to plant pathogens or to a place where plant pathogens live or to a place (plant , soil) where plant pathogens may inhabit.

Plant diseases can be controlled by applying effective amounts of the compound represented by formula (1) and the azole compound (s) to a plant or a place where a plant is allowed to grow. Just like a plant, which is the object of application, plant stem and leaves, plant seed, plant bulbs can be included. Here the bulb means a bulb, corm, rhizome, stem tuber, root tuber and rhizophore.

When application is conducted for plant diseases, to a plant or soil where the plant is allowed to grow, the compound represented by formula (1) and azol compound (s) may be applied separately during the same period. however, they are typically applied as a plant disease control composition of the present invention from the point of view of simplicity of application. The control method of the present invention includes treatment of a plant's stem and leaves, treatment of where the plant is allowed to grow, such as soil, seed treatment such as seed / seed coating sterilization and bulb treatment such as Potato sets.

As well as treating stem and leaf of a plant in the control method of the present invention, specifically, for example, application to the plant surface such as stem and leaf spraying and stem spraying may be included.

As well as soil treatment in the control method of the present invention, for example spraying on soil, mixing with soil, perfusion of a liquid agent into the soil (irrigation of a liquid agent, injection into the soil, dripping of an agent net) may be included, and examples of the place to be treated include a planting hole, a furrow, a planting hole peripheral, a planting furrow peripheral, the entire surface of the crop area, the parts between the soil and the plant, the area between the roots, the area under the trunk, the main furrow, the growing soil, the box for growing seedlings, the tray for growing seedlings, the sowing. The treatment may be carried out before spreading, at the time of spreading, immediately after spreading, during the growth period of the seedlings, before planting, at the time of planting and at the time of planting after planting. In the above-mentioned soil treatment, the active ingredients may be applied to the plant at the same time, or solid fertilizer such as paste fertilizer containing the active ingredients may be applied to the soil. The active ingredients may be mixed in the irrigation liquid, and, for example, may be injected into the irrigation facilities (irrigation pipe, irrigation pipe, sparger, etc.), mixed in the flood liquid between the furrows, or mixed in a water culture medium. Alternatively, the irrigation liquid and active ingredients may be previously mixed and, for example, used for treatment by an appropriate irrigation method, including the above-mentioned irrigation method and other methods such as spreading and flooding. Treatment of a seed in the control method of the present invention is, for example, a method for treating a seed, a bulb or the like, to be protected from plant diseases with a plant disease control composition of the present invention and specific examples. thereof include a spray treatment in which a suspension of the plant disease control composition of the present invention is atomized and sprayed onto the seed surface or the bulb surface; covering treatment in which a wetting powder, emulsion, flowable agent or the like, of the plant disease control composition of the present invention in any form or added with a small amount of water is applied to the seed surface or bulb surface ; dipping treatment in which the seed is immersed in a solution of the composition for controlling plant diseases of the present invention for a certain period of time; film coating treatment and pellet coating treatment.

When a plant or soil for growing a plant is treated with the compound represented by the formula (1) and the azole compound, for example any of bromuconazole, diphenoconazole, fluquinconazole, ipconazole, protioconazole, tetraconazole, triticonazole and metconazole, for treatment can be changed depending on the species of plant to be treated, the species and frequency of occurrence of the diseases to be controlled, form of formulation, treatment period, climatic condition and so on, but the total amount of compound represented by formula (1) and the azol compound (hereinafter the amount of active ingredients) per 10,000 m2 is typically 1 to 5000 g and preferably 2 to 200 g. The emulsion, wettable powder, flowable agent or the like is typically diluted with water, and then spread for treatment. In this case, the concentration of the active ingredients is typically in the range of 0.0001 to 3 wt% and preferably 0.0005 to 1 wt%. Powdered agent, granule agent or the like is typically used for undiluted treatment.

In seed treatment, the amount of active ingredients applied is typically in the range of 0.001 to 20 g, preferably 0.01 to 5 g per 1 kg of seeds. The control method of the present invention may be used on agricultural land such as fields, wetlands, lawns and orchards or on non-agricultural land. The present invention may be used to control diseases on agricultural land to further cultivate the "plant" and the like without adversely affecting the plant and so on.

Examples of crops are as follows: crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanuts, buckwheat, beets, rapeseed, sunflower, sugar cane, tobacco, etc. .; vegetables: solanaceous vegetables (eggplant, tomato, sweet pepper, pepper, potato, etc.), cucurbit vegetables (cucumber, pumpkin, zucchini, watermelon, melon, pumpkin, etc.), cruciferous vegetables (Japanese radish, white turnip, horseradish) spicy, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, crown daisy, artichoke, lettuce, etc.), lily vegetables (green onion, onion , garlic and asparagus), sweet vegetables (carrot, parsley, celery, flan, etc.), Kenopodiac vegetables (spinach, Swiss chard, etc.), lamiac vegetables (Perilla frutescens, mint, basil, etc.), strawberry, potato sweet, Diosco-reajaponica, colocasia, etc., flowers, foliage plants, turfgrasses, fruits: fruit (apple, pear, Japanese pear, Chinese quince, quince, etc.), fleshy stone fruits (peach, plum, nectari-na, Prunus mume, cherryfruit, apricot, prune, etc.), citrus fruits (Citrus unshiu, l orange, lemon, rime, grapefruit, etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc. ), grape, kakifruit, olive, Japanese plum, banana, coffee, date, coconuts, etc., other than fruit trees; tea, blackberry, flowering plant, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo biloba, lilac, maple, quercus, poplar, hola, liquidambar formosana, maple tree, zelcova, japanese tree-life, firwood , hemlock, juniper, Pinus, Picea and Taxus cuspidate), etc.

The "above mentioned plants" include plants to which resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr or typhenesulfurone methyl, EPSP synthetase inhibitors such as glyphosate, glutamine synthase inhibitors such as glyphosinate, acetyl CoAcarboxylase such as setoxyidim, PPO inhibitors such as flumioxazine and herbicides such as bromoxynil, dicamba, 2,4-D, etc. was conferred by a classical breeding method or genetic engineering technique.

Examples of a "plant" in which resistance has been conferred by a classical breeding method include rapeseed, wheat, sunflower, and rice resistant to imidazolinone ALS-inhibiting herbicides such as imazetapyr, which are already commercially available under a Clearfield product name. (trademark). Similarly, there is soybean in which resistance to sulfonylurea ALS-inhibiting herbicides such as typhenesulfurone-methyl has been conferred by a classical breeding method that is already commercially available under a product name of STS soy bean. Similarly, examples in which resistance to acetyl CoAcarboxylase inhibitors such as trione oxime or aryloxyphenoxypropionic acid herbicides was conferred by a classical breeding method include SR corn. The plant in which resistance to acetyl CoAcarboxylase inhibitors has been conferred is described in Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA), vol. 87, pp. 7175-7179 (1990). A variation of acetyl-CoA carboxylase resistant to an acetyl-CoA carboxylase inhibitor is reported in Weed Science, vol. 53, pp. 728-746 (2005) and a plant resistant to acetyl-CoA carboxylase inhibitors can be generated by introducing a gene of such a variation of acetyl-CoA carboxylase into a plant by genetic engineering technology, or by introducing a variation that confers resistance in a plant to acetyl-CoA carboxylase. In addition, plants resistant to acetyl CoA carboxylase inhibitors or ALS inhibitors or the like may be generated by introducing a site-directed amino acid substitution variation into an acetyl CoA carboxylase gene or the ALS gene of plant by introducing a nucleic acid into which a base substitution variation represented by the Chimeraplasty Technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) was introduced into a plant cell.

Examples of a plant in which resistance has been conferred by genetic engineering technology include corn, soybean, cottonseed rape, glyphosate resistant beet, which is already commercially available under a product name of RoundupReady (trademark), AgrisureGT, etc. Similarly, there is corn, soy, cotton and rapeseed, which are made glyphosinate resistant by genetic engineering technology, a type that is already commercially available under a product name of LibertyLink (trademark). Genetically engineered bromoxynil-resistant cotton is also commercially available under a BXN product name.

The aforementioned "plants" include genetically modified crops produced using such genetic engineering techniques that, for example, can synthesize selective toxins as known in the genus Bacillus.

Examples of toxins expressed in such genetically modified cultures include: Bacillus cereus or Bacillus popilliae insecticidal proteins; δ-endotoxins such as CrylAb, CrylAc, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus turingiensis; insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; animal generated toxins, such as scorpion toxin, spider toxin, bee toxin or insect specific neurotoxins; mold fungus toxins; plant lectin; agglutinin; protease inhibitors such as a trypsin inhibitor, a serine protease inhibitor, patatin, cystatin, or a papain inhibitor; ryosomal inactivation (RIP) proteins such as lycin, maize RIP, abrina, lufine, saporin, or briodine; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdiesteroid-UDP-glycosyl transferase or cholesterol oxidase; an ecdisone inhibitor; HMG-COA reductase; ion channel inhibitors such as a sodium channel inhibitor or calcium channel inhibitor; juvenile hormone esterase; a diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; and glycanase.

In addition, toxins expressed in such genetically modified cultures also include: δ-endotoxin hybrid protein toxins such as CrylAb, Cry1Ac, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, and insecticide proteins such as VIP1, VIP2, VIP3 or VIP3A; partially deleted toxins; and modified toxins. Such hybrid toxins are produced from a new combination of the different domains of such proteins using a genetic engineering technique. As well as a partially deleted toxin, CrylAb comprising deletion of a portion of an amino acid sequence has been known. A modified toxin is produced by substituting one or multiple amino acids for natural toxins.

Examples of such toxins and genetically modified plants capable of synthesizing such toxins are described in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878, WO 03/052073, etc.

The toxins contained in such genetically modified plants may confer resistance particularly to insect pests belonging to Coleoptera, Hemiptera, Diptera, Lepidoptera and Nematodes to the plants.

In addition, genetically modified plants comprising one or multiple insecticide-resistant genes expressing one or multiple toxins were already known, and some of such genetically modified plants were already on the market. Examples of such genetically modified plants include YieldGard (trademark) (a variety of corn to express CrylAb toxin), YieldGard Rootworm (trademark) (a variety of corn to express Cry3Bb1), YieldGard Plus (trademark) corn to express CrylAb and Cry3Bb1 toxins), Herculex I (trademark) (a variety of corn to express phosphinothricin N-acetyl transferase (PAT) to confer resistance to Cry1Fa2 toxin and glyphosinate), NuCOTN33B (trademark) CrylAc toxin-expressing cotton), Bollgard I (trademark) (a variety of CrylAc toxin-expressing cotton), Bollgard II (trademark) (a variety of CrylAc and Cry2Ab toxin-expressing cotton), VIPCOT (trademark) variety of cotton to express VIP toxin), NewLeaf (trademark) (a variety of potato to express Cry3A toxin), NatureGard (trademark) Agrisure (trademark) GT Advantage (glyphosate resistant characteristic GA21), Agrisure (trademark) CB Advantage (corn borer feature (CB) Bt11) and Protecta (trademark).

The aforementioned "plants" also include crops produced using a genetic engineering technique that is capable of generating antipathogenic substances that have selective action.

A PR protein and the like were known as such antipathogenic substances (PRPs, EP-A-0 392 225). Such antipathogenic substances and genetically modified cultures which generate them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191, etc.

Examples of such antipathogenic substances expressed in genetically modified cultures include: ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (toxins KP1, KP4 and KP6, etc., which are produced by viruses, have been known); stilbene synthase; bibenzyl synthase; chitinase; glycanase; a PR protein; and antipathogenic substances generated by microorganisms, such as a peptide antibiotic, an antibiotic having a hetero ring, a protein factor associated with plant disease resistance (which is called a plant disease resistant gene and is described in WO 03/000906). These antipathogenic substances and genetically modified plants producing such substances are described in EP-A-0392225, W095 / 33818, EP-A-0353191, etc. The above-mentioned "plant" includes plants in which advantageous qualities such as improved qualities in oily material ingredients or qualities that have enhanced amino acid content have been conferred genetically modified technology. Examples of these include VISTIVE (trademark) low linolenic soybean, which has reduced linolenic content) or high lysine (high oil content) corn (lysine or increased oil content).

In addition, cell varieties are also included, wherein a plurality of advantageous qualities such as the qualities of the classic herbicide mentioned above or herbicide tolerance genes, harmful insecticide resistance genes, antipathogenic substance producing genes, improved quality in terms of quality. Oily material or quality ingredients that have enhanced amino acid content are combined.

In the case of spray treatment a high control effect is expected in particular for plant diseases occurring in wheat, citrus plant, soybean, kidney beans, cotton, rapeseed, grape, turfgrass, pear, peach, apple, peanut. , tea, beets, bananas, rice or gourd among the above. Examples of which a particularly high control effect of the present invention is expected for plant diseases among the diseases that occur in these plants, include pink snow mold (Microdochi-an nivale), Rhizoctonia rot (Rhizoctonia solani), plant pest. Fusarium head (Fusaríum graminearum, F., avenacerum, F., culmorum, Microdochium nivale) and wheat ocelo (Pseudocercosporella herpotrichoi-des), citrus diseases: melanose (Diaporthe citrí) and crust (Elsinoe fawcetti), seed spot purples (Cercospora kikuchii), soybean plant pests (Phakopsora pachyrhizi), cotton Rhizoctonia (Rhizoctonia solani) rot, Rhizoctonia solani rot, and sclerotinia rot (Sclerotinia sclerotiorum) from nose-colza antr (nose-colza) Elsinoe ampelina), mature putrefaction (Glomerella cingulata), powdery mold (Uncinula necator), black putrefaction (Guignardia bidwellii) and grape gray mold (Botrytis cinerea) , dollar spot (Sclerotinia homeocarpa) and turfgrass brown patch (Rhizoctonia solani), pear crust (Venturia nashicola, V., pirina), flowering pest (Monilinia mali), crust (Venturia inaequalis), powdery mold (Podosphaera) leucotricha), pustule (Diplocarpon mah) and apple ring (Botryosphaeria berengeriana) putrefaction, brown rot (Monilinia fructicola) and peach rot (Phomopsis sp.), peanut early leaf spot (Cercospora arachi-dicola), Gray plant pest (Pestalotiopsis sp.) and tea antrac-nose (Colletotríchum theae-sinensis), Cercospora leaf spot (Cercospora beticola), Plant leaf pest (Thanatephorus cucu-meris) and Root putrefaction (Thanatephorus cucumerís) ), banana sigato-ka (Mycosphaerella fijiensis, Mycosphaerella musicola), rice blast (Magnaporthe grisea) and rice bakanae (Gibberella fujikuroi), Rhizoctonia (Rhizoctonia solam) rot gourd, gray mold (Botrytis cinerea) and rot of Sclerotinia (Sclerotinia sclerotiorum) from other cultures.

In the case of seed treatment, a high control effect is expected in particular for plant diseases occurring in maize, sorghum, rice, rapeseed, soybean, potato, sugar beet, cotton among the above. Among plant diseases that occur in these plants, plant diseases in which particularly high effects are expected include, Rhizoctonia rot, diseases caused by Pythium spp. and diseases caused by Fusarium spp.

EXAMPLES Hereinafter, the present invention will be described more specifically by way of formulation examples, seed treatment formulation examples, and test examples. However, the present invention is not limited to the following examples. In the following examples, the part represents part by weight unless otherwise noted in particular. Compound (1a) is a compound represented by formula (1), wherein X1 is a methyl group, X2 is a methylamino group, and X3 is a 2,5-dimethylphenyl group and the compound has an R-type steric structure according to with the rule in the order Cahn-Ingold-Prelog, and represented by the following formula (1a).

[Formula 2] (la) Compound (1b) is a compound represented by formula (1), wherein X1 is a methyl group, X2 is a methylamino group, and X3 is a 2,5-dimethylphenyl group and the compound is a racemic body and represented by the following formula (1b).

[Formula 3] (lb) Formulation example 1 2.5 parts of compound (1a) or compound (1b), 1.25 parts of bromuconazole, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of do-decyl benzene sulfonate of calcium and 76.25 parts of xylene are thoroughly mixed to obtain the respective emulsions.

Formulation example 25 Parts of compound (1a) or compound (1b), 5 parts of di-phenoconazole, 35 parts of a mixture of white carbon and a polyoxyethylene ammonium alkyl sulfate salt (weight ratio 1: 1) and 55 parts of water are mixed, and the mixture is finely milled according to a wet milling method to obtain the respective flowable agents.

Formulation Example 3 5 parts of compound (1a) or compound (1b), 10 parts of fluquinconazole, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and the mixture is subjected to fine grinding according to a wet grinding method. Thereafter, 45 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective fluids.

Formulation Example 45 Parts of compound (1a) or compound (1b), 20 parts of protioconazole, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and the mixture is subjected to fine grinding according to a wet grinding method. Thereafter, 45 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective flowable formulations.

Formulation example 5 40 parts Compound (1a) or compound (1b), 5 parts t-traconazole, 5 parts propylene glycol (manufactured by Nacalai Tesque), 5 parts SoprophorFLK (manufactured by Rhodia Nikka), 0, 2 parts of an antiform C emulsion (manufactured by Dow Corning), 0.3 parts of proxx GXL (manufactured by Arch Chemicals) and 49.5 parts of ion exchange water are mixed to obtain a volume suspension. 150 parts of glass beads ((diameter = 1 mm) are placed in 100 parts of the suspension, and the suspension is ground for 2 hours while cooled with a cooling water. Once ground, the resultant is filtered to remove the glass beads and their fluids were obtained.

Formulation Example 6 50 parts Compound (1a) or compound (1b), 0.5 parts triticonazole, 38.5 parts NN kaolin clay (manufactured by Takehara Chemical Industrial), 10 parts MorwetD425 and 1.5 parts MorwerEFW (manufactured by Akzo Nobel Corp.) are mixed to obtain a premix of Al. This premix was ground with a jet mill to obtain the respective powders.

Formulation Example 7 1 Part compound (1a) or compound (1b), 4 parts bro-muconazole, 1 part synthetic hydrated silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 62 parts Kaolin clay is completely ground and mixed, and the resulting mixture is added with water and thoroughly kneaded, then granulated and dried to obtain the respective granules.

Formulation Example 8 1 Part of compound (1a) or compound (1b), 40 parts di-phenoconazole, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide are completely ground and mixed to obtain their wettable powders.

Formulation Example 9 1 Part compound (1a) or compound (1b), 2 parts flu-quinconazole, 85 parts kaolin clay and 10 parts talc are thoroughly ground and mixed to obtain the respective powders.

Formulation example 10 2 parts Compound (1a) or compound (1b), 0.25 parts protioconazole, 14 parts polyoxyethylene styrylphenyl ether, 6 parts calcium do-decyl benzene sulfonate and 77.75 parts xylene are thoroughly mixed to obtain the respective emulsions.

Formulation example 11 10 parts of compound (1a) or compound (1b), 2.5 parts of tetraconazole, 1.5 parts of sorbitan trioleate, 30 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are subjected to Fine grinding according to a wet grinding method. Thereafter, 47.5 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the milled solution, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective fluids.

Formulation example 12 1 part Compound (1a) or compound (1b), 20 parts tri-thiconazole, 1 part synthetic hydrated silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 47 parts Kaolin clay is ground and mixed, and the resulting mixture is added with water and thoroughly kneaded, then granulated and dried to obtain the respective granules.

Formulation example 13 40 Parts of compound (1a) or compound (1b), 1 part ip-conazole, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide are completely ground and mixed to obtain their wettable powders.

Formulation example 14 2.5 parts of compound (1a) or compound (1b), 1.25 parts of metconazole, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of dodecyl benzene sulfonate and 76.25 parts of xylene are thoroughly mixed to obtain the respective emulsions.

Formulation example 15 5 parts of compound (1a) or compound (1b), 5 parts of ip-conazole, 35 parts of a mixture of white carbon and a polyoxyethylene ammonium alkyl sulfate salt (weight ratio 1: 1) and 55 parts of water are mixed, and the mixture is subjected to fine grinding according to a wet grinding method to obtain the respective flowable agents. Formulation example 16 5 parts of compound (1a) or compound (1b), 10 parts of metconazole, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and the mixture is subjected to fine grinding according to a wet grinding method. Thereafter, 45 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective fluids.

Formulation example 17 5 parts of compound (1a) or compound (1b), 20 parts ip-conazole, 1.5 parts sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts polyvinyl alcohol are mixed, and the mixture is finely milled according to a wet milling method. Thereafter, 45 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective flowable formulations.

Formulation example 18 40 parts Compound (1a) or compound (1b), 5 parts metconazole, 5 parts propylene glycol (manufactured by Nacalai Tesque), 5 parts SoprophorFLK (manufactured by Rhodia Nikka), 0.2 parts of an antiform emulsion C (manufactured by Dow Corning), 0.3 part proxx GXL (manufactured by Arch Chemicals) and 49.5 parts ion exchange water are mixed to obtain a volume suspension. 150 parts of glass beads ((diameter = 1 mm) are placed in 100 parts of the suspension and the suspension is milled for 2 hours while being cooled with a cooling water. After grinding, the resultant is filtered to remove the glass beads and their fluids were obtained.

Formulation Example 19a 50 parts Compound (1a) or compound (1b), 0.5 parts ipconazole, 38.5 parts NN kaolin clay (manufactured by Takehara Chemical Industrial), 10 parts MorwetD425 and 1.5 parts MorwerEFW (manufactured by Akzo Nobel Corp.) are mixed to obtain a premix of Al. This premix was ground with a jet mill to obtain the respective powders.

Formulation Example 19b 1 part Compound (1a) or compound (1b), 4 parts metconazole, 1 part synthetic hydrated silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 62 parts Kaolin clay is completely ground and mixed, and the resulting mixture is added with water and completely kneaded, then granulated and dried to obtain the respective granules.

Formulation Example 20 1 Part of compound (1a) or compound (1b), 40 parts ip-conazole, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide are completely ground and mixed to obtain their wettable powders.

Formulation Example 21 1 Part compound (1a) or compound (1b), 2 parts metconazole, 85 parts kaolin clay and 10 parts talc are thoroughly ground and mixed to obtain the respective powders.

Formulation example 22 2 parts of compound (1a) or compound (1b), 0.25 parts of ipconazole, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of dodecyl benzene sulfonate and 77.75 parts of xylene are completely mixed to obtain their emulsions.

Formulation example 23 10 parts of compound (1a) or compound (1b), 2.5 parts of metconazole, 1.5 parts of sorbitan trioleate, 30 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are subjected to Fine grinding according to a wet grinding method. Thereafter, 47.5 parts of an aqueous solution containing 0.05 parts Xanthan gum and 0.1 parts aluminum magnesium silicate are added to the milled solution, and 10 parts propylene glycol are also added thereto. The obtained mixture is mixed by stirring to obtain the respective fluids.

Formulation example 24 1 part Compound (1a) or compound (1b), 20 parts ip-conazole, 1 part synthetic hydrated silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 47 parts Kaolin clay is ground and mixed, and the resulting mixture is added with water and thoroughly kneaded, then granulated and dried to obtain the respective granules.

Formulation Example 25 40 Parts of compound (1a) or compound (1b), 1 part metconazole, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide are completely ground and mixed to obtain their wettable powders.

Seed Treatment Example 1 An emulsion prepared as in Formulation Example 1 is used for covering treatment in an amount of 500 ml per 100 kg of dried sorghum seeds using a rotary seed treatment machine (seed dresser, produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 2 A flowable prepared as in Formulation Example 16 is used for covering treatment in an amount of 50 ml per 10 kg of dried rapeseed seeds using a seed dresser produced by Hans-Hansen. UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 3 A flowable prepared as in Formulation Example 17 is used for mulching treatment in an amount of 40 ml per 10 kg of dried corn seeds using a seed dresser produced by Hans -UIrich Hege GmbH) to obtain treated seeds.

Seed treatment example 45 parts of a flowable agent prepared as in Formulation Example 18, 5 parts of BPD6135 pigment (manufactured by Sun Chemical) and 35 parts of water are mixed to prepare a mixture. The mixture is used for covering treatment in an amount of 60 ml per 10 kg of dried rice seeds using a seed dresser produced by Hans-UIrich Hege GmbH to obtain treated seeds.

Seed Treatment Example 5 A powdered agent prepared as in Formulation Example 19a is used for treating powder coating in an amount of 50 g per 10 kg of dried corn seeds to obtain treated seeds. Seed Treatment Example 6 An emulsion prepared as in Formulation Example 22 is used for covering treatment in an amount of 500 ml per 100 kg of dried beet seeds using a seed dresser produced by Hans -UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 7 A flowable prepared as in Formulation Example 23 is used for covering treatment in an amount of 50 ml per 10 kg of dried soybean seeds using a seed dresser produced by Hans -UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 8 A granule agent prepared as in Formulation Example 24 is used for covering treatment in an amount of 50 ml per 10 kg of dried wheat seeds using a seed dresser produced Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed treatment example 95 parts of a wettable powder prepared as in Formulation Example 25, 5 parts of BPD6135 pigment (manufactured by Sun Chemical) and 35 parts of water are mixed, and the resulting mixture is used for top coat treatment. 70 ml per 10 kg of potato tuber pieces using a seed dresser (produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 10 A wettable powder prepared as in Formulation Example 20 is used for treating powder coating in an amount of 40 g per 10 kg of dried cottonseed to obtain treated seed. Example Test 1 A plastic pot was loaded with sandy soil, and cucumber (Sagamihanjiro) was then disseminated. The cucumber was allowed to grow in a greenhouse for 12 days. A wettable powder of compound (1b) and a commercially available metconazole formulation (Caramba (trademark) produced by BASF) were respectively diluted with water and then tank mixed to prepare tank mixed liquids containing compound (1b) and metconazole. at predetermined concentration. Tank mixed liquids have been subjected to foliage application such that they can be sufficiently adhered to the leaves of the aforementioned cucumber plants. After completion of foliage application, the plants were air dried. Thereafter, a PDA nutrient medium containing Botrytis cinerea spores, a cucumber gray mold pathogen, was placed on the leaf surface of cucumber plants. They were placed at 12 ° C under high humidity for 6 days after inoculation, and after that the control effect was checked. The diameter of the infected area on the plants to which the agents had been sprayed was determined as the disease incidence at the time of check, and the control value was calculated by Equation 1 based on the disease incidence thus determined.

As a comparison, the respective humectable powders described above were diluted with water at the predetermined concentration to prepare a liquid compound, (1b) and a liquid metconazole respectively, and they were subjected to similar disease control testing. In addition, to calculate the control value, disease incidence was also determined in the event that plants were not treated with the agent.

The results are shown in table 2.

"Equation 1"; Control value = 100 (A - B) / AA: Incidence of plant disease or acreage in untreated area B: Incidence of plant disease or acreage in treated area Generally, the expected control value for the case where, Since the two types of active ingredient compounds are mixed and used for treatment, the so-called control value expectation is calculated from the following Colby equation. "Equation 2"; X: Control value (%) when active ingredient compound A is used for treatment in M ppm, M g per 100 kg of seeds or M g per 1 hectare Y: Control value (%) when treatment compound active ingredient B is used for treatment in N ppm, N g per 100 kg of seeds or N g per 1 hectare E: Expected control value (%) if compound of active ingredient A in M ppm, in M g per 100 kg of seeds or M g per 1 hectare and composed of active ingredient B in N ppm, N g per 100 kg of seeds or N g per 1 hectare are mixed and used for treatment (hereinafter " Control Value Expectation ")" Synergistic Effect (%) "= (Actual Control Value) x 100 / (Control Value Expectation) [Table 2] Test Example 2 Mixed liquids containing a compound acetone solution (1b ) and a metconazole acetone solution were prepared. These mixed liquids were used to treat cucumber (Sagamihanjiro) seed dressing using a seed dresser (Hans Dresser, produced by Hans-UIrich Hege GmbH) to obtain treated seeds. The treated seeds were left untouched overnight and then spread into the soil loaded with a plastic pot and covered with soil containing Rhizoctonia solani, a cucumber rotting pathogen, which was grown in a bran medium. They were allowed to grow in a greenhouse at the same time as irrigated and the number of un sprouted seeds was inspected on the seventh day after spreading, and disease incidence was calculated by Equation 3. The control value was calculated by Equation 1 above. mentioned, based on the incidence of the disease. As a comparison, acetone solutions containing compound (1b) and metconazole respectively at the predetermined concentration were prepared and subjected to similar tests.

The results are shown in table 3. "Equation 3"; Disease incidence = (Number of seeds not sprouted) x 100 / (Total number of seeds spread) [Table 3] ________________________________________________________ Example Test 3 A plastic pot was loaded with sandy soil, and cucumber (Sagamihanjiro) was then disseminated. The cucumber was allowed to grow in a greenhouse for 12 days. A wettable powder of compound (1b) and a commercially available ipconazole formulation (Tec-hlead wettable powder produced by Kureha Corporation) were respectively diluted with water and then tank mixed to prepare tank mixed liquids containing compound (1b). and ipconazole in predetermined concentration. The tank mixed liquids have been subjected to foliage application such that they can be sufficiently adhered to the leaves of the aforementioned cucumber plants. After completion of foliage application, the plants were air dried. Thereafter, a PDA nutrient medium containing Botrytis cinerea spores, a cucumber gray mold pathogen, was placed on the leaf surface of cucumber plants. They were placed at 12 ° C under high humidity for 6 days after inoculation, and after that the control effect was checked. The diameter of the infected area in the plants on which the agents had been sprayed was determined as the disease incidence at the time of check and the control value was calculated by Equation 1 above based on the disease incidence thus determined.

As a comparison, the respective humectable powders described above were diluted with water at a predetermined concentration to prepare a compound, (1b) liquid and a liquid ipconazole respectively, and they were subjected to similar disease control testing. In addition, to calculate the control value, disease incidence was also determined in the event that plants were not treated with the agent.

Results are shown in table 4.

[Table 4] Example Test 4 An acetone solution of compound (1b) and an acetone solution of ipconazole was mixed to prepare mixed liquids containing compound (1b) and ipconazole at a predetermined concentration. These mixed liquids were used for cucumber (Sagamihanjiro) seed dressing treatment using a seed dresser (Hans Dresser, produced by Hans-UIrich Hege GmbH) to obtain the treated seeds. The treated seeds were left untouched overnight and then dispersed in soil loaded in a plastic pot and covered with soil containing Rhizoctonia solani, cucumber pathogen rot, which was grown in a bran medium. They were allowed to grow in a greenhouse while irrigated and the number of un sprouted seeds was checked on the seventh day after the spread and incidence of the disease were calculated by Equation 3 above. The control value was calculated by Equation 1 above based on disease incidence. To calculate the control value, disease incidence was also determined in the event that plants were not treated with the agent.

As a comparison, acetone solutions containing compound (1b) and ipconazole respectively at the predetermined concentration were prepared and subjected to similar tests.

[Table 5] ____________________________i___________________________ Example Test 5 A plastic pot was loaded with sandy soil, and grass (Bent Grass Penncross) was then disseminated. The grass was allowed to grow in a greenhouse for 20 days. A wettable powder of compound (1b) and a commercially available metconazole formulation (Caramba (trademark) produced by BASF) were diluted respectively with water and then tank mixed to prepare tank mixed liquids containing compound (1b) and metconazole at a predetermined concentration. Tank mixed liquids have been subjected to foliage application such that they can be sufficiently adhered to the leaves of the aforementioned grass plants. After completion of foliage application, the plants were air dried. After that, bran medium containing Rhizoctonia solani mycelium, pathogen of brown grass patch, was sprayed onto the planted area. They were placed at 12 ° C-23 ° C under high humidity for 10 days after inoculation, and after that the control effect was checked. The diameter of the infected area in the planted area into which the agents had been sprayed was determined when the disease incidence at check time and the control value were calculated by Equation 1 above based on the disease incidence determined.

As a comparison, respective wettable powders described above were diluted with water at predetermined concentration to prepare a compound as a comparison, (1b) liquid and a liquid metconazole respectively and they were subjected to similar disease control testing. In addition, to calculate the control value, disease incidence was also determined in the event that plants were not treated with the agent.

Results are shown in table 6.

[Table 61 ________________i_________________________________________ INDUSTRIAL APPLICABILITY

In accordance with the present invention, a composition for controlling plant diseases having high activity, and a method for effectively controlling plant diseases may be provided.

Claims (5)

Plant disease control composition, characterized in that it comprises as active ingredients a compound represented by the formula (1b): [Formula 1b] (Ib) and an azol compound selected from the group consisting of: ipconazole, and metconazole, wherein the weight ratio of the compound represented by formula (1b) to an azol compound is in the range 1: 0.01 to 1: 15.5. Composition according to Claim 1, characterized in that it has a weight ratio of the compound represented by the formula (1b) to an azol compound which is in the range from 01: 1 to 1: 4. Seed treatment agent, characterized in that it comprises as active ingredients the compound represented by the formula (1b) as defined in claim 1 and an azol compound selected from the group consisting of ipconazole and metconazole in that the weight ratio of the compound represented by formula (1b) to an azole compound is in the range of 1: 0.01 to 1: 15.5. A method for controlling plant diseases, characterized in that it comprises applying to a plant or a place where a plant is allowed to cultivate effective amounts of the compound represented by formula (1b) as defined in claim 1 and a compound of azol selected from the group consisting of ipconazole and metconazole, wherein the weight ratio of the compound represented by formula (1b) to an azol compound is in the range 1: 0.01 to 1: 15.5. Combined use, characterized in that it is for controlling plant diseases of the compound represented by formula (1b) as defined in claim 1 and an azol compound selected from the group consisting of ipconazole and metconazole, wherein the ratio in The weight of the compound represented by formula (1b) for an azol compound is in the range 1: 0.01 to 1: 15.5.