BRPI0921930B1 - COMPOSITION AND METHOD FOR CONTROL OF PLANT DISEASES, SEED TREATMENT AGENT AND COMBINED USE - Google Patents

Description

Report of the Invention Patent for "COMPOSITION AND METHOD FOR CONTROL OF PLANT DISEASES, SEED TREATMENT AGENT AND COMBINED USE" *.

Technical Field The present invention relates to a plant disease control composition and a method for plant disease control. Background Art α-substituted phenylacetic acid compounds (see, for example, WO 95 / 27,693) and etaboxam (see, for example, KR-B-0124552) are conventionally known as active ingredients of plant disease control agents. . However, there is still a need for higher active agents for plant disease control.

Disclosure of the Invention An object of the present invention is to provide a plant disease control composition and method for plant disease control and so on, with excellent control effect for plant diseases. The present invention provides a plant disease control composition and method for plant disease control, with a better plant disease control effect by combining a compound represented by the following formula (1) with etaboxam.

Specifically, the present invention has the following embodiments.

[1] A plant disease control composition comprising as active ingredients a compound represented by formula (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 ethaboxam;

[2] The composition according to [1], which has a weight ratio of the compound represented by formula (1) to ethaboxam within the range of 0.01: 1 to 200: 1;

[3] A seed treatment agent comprising as active ingredients the compound represented by the formula (1) of [1] and etaboxam;

[4] A plant seed treated with effective amounts of the compound represented by the formula (1) of [1] and etaboxam;

[5] A method for the control of plant diseases comprising applying to a plant or place where a plant is grown effective amounts of the compound represented by the formula (1) of [1] and etaboxam; and [6] The combined use for plant disease control of the compound represented by the formula (1) of [1] and etaboxam; and so on. The composition according to the present invention exhibits an excellent control effect for plant diseases.

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

Specific examples of the compound represented by formula (1) are shown.

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

The compound represented by formula (1) may have isomers, such as stereoisomers, as optical isomers based on asymmetric carbon atoms, and tautomers, and any isomer may be contained and used alone or in admixture of any ratio of isomers herein. invention. The compound represented by formula (1) may be in the form of a solvate (e.g. hydrate) and it may be used in the form of a solvate in the present invention. The compound represented by formula (1) may be in the form of a crystalline 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 report WO95 / 27693. Such compounds may be synthesized, for example, by a method described in the report.

Etaboxam for use in the plant disease control composition according to the present invention in combination with the compound represented by formula (1) is a compound described in KR-B-0124552 and may be obtained from commercial agents or prepared using are well known methods.

In the plant disease control composition according to the present invention, the weight ratio of the compound represented by the formula (1) to etaboxam is typically in the range 0.01: 1 to 200: 1, preferably 0.025: 1. at 125: 1. When used as a dusting powder, the range from 0.05: 1 to 125: 1 is more preferable, and when used as a seed treatment agent, the range from 0.025: 1 to 100: 1 is most preferable. The plant disease control composition according to the present invention may be a simple mixture of the compound represented by formula (1) and etaboxam. Alternatively, the plant disease control composition is typically produced by mixing the compound represented by formula (1) and etaboxam with an inert carrier, and adding to the mixture a surfactant and other necessary adjuvants so that the mixture can be mixed. formulated into an oily agent, an emulsion, a fluid agent, a wetting powder, a granulated wetting powder, a powdered agent, a granular agent and so on. The aforementioned plant disease control composition may be used as a seed treatment agent of the present invention as is or with other inert ingredients.

In the plant disease control composition according to the present invention, the total amount of the compound represented by formula (1) and etaboxam is typically in the range 0.1 to 99% by weight, preferably 0.2 to 90% by weight.

Examples of the solid carrier used in the formulation include fine powders or granules such as minerals such as kaolin clay, attapulgite clay, bento-nite, 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 methylnaphthalene; alcohols, such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether; ketones such as acetone, cyclohexanone and isophorone; vegetable oils such as soybean oil and cottonseed oil; petroleum aliphatic hydrocarbons, esters, dimethyl sulfoxide, acetonitrile and water.

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

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

Rice diseases: blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), root rot (Rhizoctonia solani) and ear and stem rot (Gibberella fujikuroi).

Wheat diseases: powdery mildew (Erysiphe graminis), fusariose (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), linear rust (Puccinia striiformis, P. graminis, P. recondita), pink rot (Micro-nectriella nivale) , Typhula (Typhula sp.) rust, charcoal (Ustilago triti-cí), fetid charcoal (Tilletia caries), crazy bed (Pseudocercosporella herpo-trichoides), leaf spot (Mycosphaerella graminicola), melanosis (Stago-nospora nodorum) yellow (Pyrenophora tritici-repentis).

Barley diseases: powdery mildew (Erysiphe graminis), gibberella (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), linear rust (Puccinia striiformis, P. graminis, P. hordei), charcoal (Ustilago nu-da), scalding (Rhynchosporium secalis), reticular spot (Pyrenophora teres), rot (Cochliobolus sativus), helminthsporiose (Pyrenophora gra-minea) and root rot (Rhizoctonia solani).

Corn diseases: common charcoal (Ustilago maydis), leaf spot (Cochliobolus heterostrophus), zoned spot (Gloeocercospora sor-ghi), southern leaf blight (Puccinia polysora), gray leaf spot (Cercos-pora zeae-maydis) and root rot (Rhizoctonia solani).

Citrus diseases: melanosis (Diaporthe citri), wart (Elsi-noe fawcetti), green mold (Penicillium digitatum, P. italicum) and brown rot (Phytophthora parasitica, Phytophthora citrophthora).

Apple diseases: Inflorescence drought (Monilinia mali), Cancer (Waltz ceratosperma), Powdery mildew (Podosphaera leucotricha), Alternaria spot (Alternaria alternata pathotype apple), Wart (Venturia inaequa-lis), Black flower (Colletotrichum acutatum) rot (Phytophtora cac-torum), spot (Diplocarpon mali) and ring rot (Botryosphaeria be-rengeriana).

Pear diseases: wart (Venturia nashicola, V. pirina), black spot (Alternaria alternata Japanese pear pathotype), linear rust (Gymnosporangium haraeanum) and fruit rot by phytophthora (Phytophtora cactorum);

Peach diseases: brown rot (Monilinia fructicola), wart (Cladosporium carpophilum) and phomopsis rot (Phomop-sis sp.).

Grape diseases: anthracnose (Elsinoe ampelina), mature grape rot (Glomerella cingulata), powdery mildew (Uncinula necator), linear rust (Phakopsora ampelopsidis) black rot (Guignardia bidwellii) and vine mildew (Plasmopara viticola).

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

Pumpkin diseases: Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), Gummy stem crest (Mycosphaerella melonis), Fusarium wilt (Fusarium oxysporum), Mellow (Pseudo-peronospora cubensis), Phytophthora and Phytophthora rot seedling wilt (Pythium sp.);

Tomato diseases: black spot (Alternaria solani), leaf mold (Cladosporium fulvum) and tomato blight (Phytophthora infestans).

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

Cruciferous vegetable diseases: Alternaria spot (Alternaria japonica), white spot (Cercosporella brassicae), hernia (Plasmodiopho-ra brassicae) and downy mildew (Peronospora parasitica).

Chive diseases: linear rust (Puccinia allii) and downy mildew (Peronospora destructor).

Soybean diseases: leaf cropping (Cercospora kikuchii), squid (Elsinoe glycines), stem cancer (Diaporthe phaseolorum var. Soybean), septoria leaf spot (Septoria glycines), frogeye spot (Cercospora sojina ), linear rust (Phakopsora pachyrhizi), soybean root rot (Phytophthora soye) and root rot (Rhizoctonia solani).

Bean diseases: anthracnose (Colletotrichum lindemthianum).

Peanut diseases: leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola) and gray mold (Sclerotium rolfsií).

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

Potato diseases: black spot (Alternaria solani), potato mildew (Phytophthora infestans), pink rot (Phytophthora erythrosap-tica) and powdery scab (Spongospora subterranean f. Sp. Subterranean).

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

Tea diseases: reticular mangra (Exobasidium reticulatum), white wart (Elsinoe leucospila), gray mangra (Pestalotiopsis sp.) And anthracnose (Colletotrichum theae-sinensis).

Tobacco diseases: leaf spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina) and gumose (Phytophthora nicotianae).

Rapeseed diseases: sclerotin rot (Sclerotinia sclerotio-rum) and root rot (Rhizoctonia solani).

Cotton diseases: root rot (Rhizoctonia solani).

Beet diseases: leaf spot by Cercospora (Cercospora beticola), leaf mangrove (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris) and root rot by Aphanomyces (Apha nomyces cochlioides).

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

Chrysanthemum and asteraceous plant diseases: downy mildew (Bremia lac-tucae), leaf mangrove (Septoria chrysanthemi-indici) and white linear rust (Puccinia horiana).

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

Japanese radish disease: Alternaria spot (Alternaria brassicicola).

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

Banana disease: Banana tree black sigatoka (Mycosphaerel-la fijiensis, Mycosphaerelia musicola).

Sunflower disease: downy mildew (Plasmopara halstedii).

Seed diseases or diseases in the early stages of plant growth caused by Aspergillus spp, Penicillium spp, Fusarium spp, Gibberella spp, Tricoderma spp, Thielaviopsis spp, Rhizo-pus spp, Mucorspp, Corticium spp, Phoma spp, Rhizoctonia spp. and Diplo-day spp.

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

Examples of the diseases for which a high control effect is expected among the above include root rot (Rhizoctonia solani) of wheat, maize, rice, soybean, cottonseed rape, sugar beet and grass, wilting and rot of wheat root, barley, maize, rice, sorghum, soybean, cotton, rapeseed, sugar beet and grass caused by Pythium spp. (Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum), seed diseases and diseases in the early stages of wheat, maize, cotton, soybean, rapeseed and grass growth caused by Fusarium spp, pink powder (Microdochium nivale), root rot (Rhizoctonia solani), gibberella (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale) and crazy bedrock (Pseudocercosporella herpotrichoides) from wheat, citrus diseases: melanose (Diaporthe citri) and verrinoose (ci) ), leaf growth (Cercospora. kikuchii), linear rust (Phakopsora pachyrhizi) and soybean root rot (Phytophthora soye), soybean gum (Phytophthora nicotianae), root rot (Rhizoctonia solani) of cotton, root rot (Rhizoctonia solani) and sclerotinic rot (Sclerotinia scle-rotiorum) of rapeseed, anthracnose (Elsinoe ampelina), ripe grape rot (Glomerella cingulata), powdery mildew (Uncinula nec actor), black rot (Guignardia bidwellii) and gray grape mold (Botrytis cinerea), dollar spot (Sclerotinia homeocarpa) and brown grass spot (Rhizoctonia solani), wart (Venturia nashicola, V. pirina), dried inflorescences (Monilinia ma-li), wart (Venturia inaequalis), powdery mildew (Podosphaera leucotricha), spot (Diplocarpon maii) and apple ring rot (Botryosphaeria berengeriana), brown rot (Monilinia fructicola) and phomopsis rot (Pho- peach mopsis sp.), early leaf spot (Cercospora arachidicola), peanut, gray mangrove (Pestalotiopsis sp.) and tea anthracnose (Colletotrichum theae-sinensis), leaf spot by Cercospora (Cercospora beticola), leaf mangor cucumber (Thanateph) , root rot (Thanatephorus cucumeris) and root rot by Aphanomyces (Aphanomyces cochlioides) of sugar beet, Banana tree (Mycosphaerella fijiensis, Mycos-phaerella musicola) banana, brusone (Magnaporthe g risea) and ear and stem rot (Gibberella fujikuroi) from rice, pumpkin root rot (Rhizoctonia solani), sunflower vine (Plasmopara halstedii) mildew, potato mildew (Phytophthora infestans) and late blight (Rhizoctonia solani) ) of potato, gray mold (Botrytis cinerea) and sclerotin rot (Sclerotinia sclerotiorum) from other crops.

Examples of diseases that are expected to have a particularly high control effect among the above include root rot (Rhizoctonia solani) of wheat, maize, rice, soybean, cottonseed rape, sugar beet and grass, seedling wilting and wheat root rot. , barley, corn, rice, sorghum, soybean, cotton, rapeseed, sugar beet and grass caused by Pythium spp. (Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum), seed diseases and diseases in the early stages of wheat, corn, cotton, soybean, rapeseed and grass growth caused by Fusarium spp., Soybean root rot (Phytophthora soye) From Soybean, Gummy Bean (Phytophthora nicotianae) From Tobacco, Sunflower From Vine (Plasmopara halstedii) From Sunflower, Potato Mildew (Phytophthora infes-tans) And Potato, Root Rot By Aphanomyces cochli-o ) of beet.

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

Plant diseases can be controlled by applying effective amounts of the compound represented by formula (1) and etaboxam to a plant or the place where a plant is grown. As a plant which is subject to application, one may include plant stem and leaves, plant seed, plant bulbs. Here, bulb means a bulb, corm, rhizome, stem tuber, root tuber and rhizophore.

When conducting application to plant diseases, the plant or the soil where the plant is grown, the compound represented by formula (1) and etaboxam may be applied separately during the same period, but are typically applied as a composition for the plant. plant disease control of the present invention from the point of view of simplicity of application. The control method of the present invention includes treating the stem and leaves of a plant, treating the place where the plant is grown, such as soil, treating seeds, such as seed sterilization / seed coating, and bulb treatment. , like sets of potatoes.

As a stem and leaf treatment of a plant in the control method of the present invention, specifically, for example, it may include application to the surface of the plant, such as stem and leaf spraying and stem spraying.

As a soil treatment in the control method of the present invention, for example, it may include soil spraying, mixing with the soil, perfusion of a liquid agent into the soil (irrigation of a liquid agent, injection into the soil, dripping of a soil). liquid agent), and examples of the site to be treated include a planting hole, a furrow, the periphery of the planting hole, the periphery of the planting furrow, the entire surface of the growing 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 creating the seedlings, the tray for creating the seedlings, the seedbed. Treatment may be carried out before spreading, at the time of spreading, immediately after spreading, during the seedling rearing period, before definitive planting, at the time of permanent planting and in the period of growth after permanent 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 irrigation facilities (irrigation pipe, irrigation pipe, sprinkler and others), mixed in the soaking liquid between the grooves or mixed in a culture medium in water. Alternatively, the irrigation liquid and active ingredients may be premixed and, for example, used for treatment by an appropriate irrigation method, including the above-mentioned irrigation method and other methods such as spraying and soaking. The treatment of a seed in the control method of the present invention is, for example, a method for treating a seed, bulb or other to be protected against plant diseases with a plant disease control composition of the present invention. and specific examples thereof include a spray treatment wherein a suspension of the plant disease control composition of the present invention is atomized and sprayed onto the seed surface or bulb surface; greasing treatment, wherein a wetting powder, emulsion, fluid or other agent of the plant disease control composition of the present invention as it is or plus a small amount of water is applied to the seed surface or surface. of the bulb; dipping treatment wherein the seed is dipped in a solution of the plant disease control composition of the present invention for a certain period of time; film coating treatment and pellet coating treatment.

When a plant or the soil for growing a plant is treated with the compound represented by formula (1) and etaboxam, the amount for treatment may be changed depending on the type of plant to be treated, the type and the frequency of occurrence. diseases to be controlled, the form of formulation, the treatment period, the weather conditions and so on, but the total amount of the compound represented by the formula (1) and etaboxam (hereinafter called the amount of the active ingredients) by 10,000 m2 is typically from 1 to 5,000 g and preferably from 2 to 400 g. The emulsion, wetting powder, fluid agent or the like is typically diluted with water and then sprayed 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, rice fields, lawns and orchards, or on non-agricultural land. The present invention can be used to control diseases on agricultural land for cultivating the following "plants" and others without adversely affecting the plant and so on.

Examples of crops are as follows: crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, beets, rapeseed, sunflower, sugar cane, tobacco, and others; vegetables: solanaceous vegetables (eggplant, tomato, pepper, pepper, potato, and others), cucurbitaceous vegetables (cucumber, moranga, courgette, watermelon, melon, pumpkin, and others), cruciferous vegetables (Japanese radish, white turnip, root horseradish, cabbage, Chinese cabbage, cabbage, mustard leaf, broccoli, cauliflower and others), asteraceous vegetables (burdock, ordinary pampilho, artichoke, lettuce, and others), lily vegetables (green onion, onion, garlic and asparagus), sweet vegetables (carrots, parsley, celery, parsnips, and others), kenopodiac vegetables (spinach, chard, and others), lamia vegetables (white perilla, mint, basil, and others), strawberry, sweet potato, Dioscorea japonica, colocasia, and others, flowers, foliage plants, grasses, fruits: fruit (apple, pear, japanese pear, chinese quince, quince, and others), fleshy fruit with pits (peach, plum, nectarine, japanese plum, cherry, apricot, plum raisin, and others), citrus fruits ina satsuma, orange, lime, lemon, tangerine, and others), nuts (nuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, and others), berries (blueberries, blueberries, blackberries, raspberries, and others) ), grape, persimmon, olive, Japanese plum, banana, coffee, date, coconut, and others, trees, and fruit trees; tea, mulberry, flowering plants, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo biloba, lilac, maple, oak, poplar, olaia, liquidambar formosa-na, rossio maple, zelkova, japanese arborvita , spruce, tsuga, juniper, pine, picea and Taxus cuspidate), and others.

The above-mentioned "plants" include plants to which resistance to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapir or tifensulfuron methyl, EPSP synthetase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, Acetyl-CoA carboxylase, such as setoxyidim, PPO inhibitors, such as flumioxazin, and herbicides such as bromoxynil, dicamba, 2,4-D, and others, were conferred by a classical crossover method or genetic engineering technique.

Examples of a "plant" resisted by a classic mating method include ALS imidazolinone inhibitor herbicide-resistant rapeseed, wheat, sunflower and rice, such as imazetapyr, which are already commercially available under the product name Clearfield (brand name). registered). Similarly, there is soybean which has been conferred resistance to ALS sulfonylurea inhibitor herbicides such as tifensulfuron-methyl by a classic cross-breeding method which is already commercially available under the name STS soy product. Likewise, examples which have been conferred resistance to acetyl CoA carboxylase inhibitors, such as trione oxime, or aryloxy phenoxypropionic acid herbicides by a classical mating method include SR maize. The plant conferred resistance to acetyl CoA carboxylase inhibitors 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 from ace-til-CoA carboxylase resistant to 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 this variation of acetyl-CoA carboxylase into a plant by genetic engineering technology or by introducing a resistance-giving variation. in a plant acetyl CoA carboxylase. In addition, plants resistant to acetyl CoA carboxylase inhibitors or ALS or other inhibitors may be generated by introducing a site-directed amino acid substitution variation into an acetyl CoA carboxylase gene or the plant ALS gene by introduction of a nucleic acid into which a base substitution variation represented in Chimera-plasty Technique (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318) has been introduced into a plant cell.

Examples of a plant that has been endowed by genetic engineering technology include glyphosate resistant corn, soybean, cottonseed rape and beet, which are already commercially available under the product name of RoundupReady (trademark), AgrisureGT, and others. . Similarly, there is corn, soy, cotton and rapeseed that are made glufosinate resistant by genetic engineering technology, a type that is already commercially available under the product name of LibertyLink (trademark). A bromoxynil resistant cotton taken by genetic engineering technology is also commercially available under the product name BXN.

The aforementioned "plants" include genetically modified crops produced using genetic engineering techniques which, for example, are capable of synthesizing selective toxins such as those known in the genus Bacillus.

Examples of toxins expressed in these genetically modified crops include: Bacillus ce-reus or Bacillus popilliae insecticidal proteins; δ-endotoxins such as CrylAb, CrylAc, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringi-ensis; 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 fungal toxins; plant lectin; agglutinin; protease inhibitors, such as a trypsin inhibitor, a serine protease inhibitor, patatin, cystatin, or a papain inhibitor; ribosome inactivating proteins (RIPs) such as lycin, maize RIP, abrina, lufine, saporin or brydine; steroid metabolizing enzymes such as 3-hydroxysteroid oxidase, ecdiesteroid-UDP-glucosyl 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 synthetase; bi-benzyl synthetase; chitinase; and glucanase.

Toxins expressed in these genetically modified crops 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. These hybrid toxins are produced from a new combination of different domains of these proteins using a genetic engineering technique. As a partially deleted toxin, CrylAb is known, which comprises deletion of part of an amino acid sequence. A modified toxin is produced by substituting one or multiple amino acids for natural toxins.

Examples of such toxins and genetically engineered 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, and others.

The toxins contained in these genetically engineered plants are capable of conferring resistance, particularly to insect pests belonging to Coleoptera, Hemiptera, Diptera, Lepidoptera and Nematodes, to the plants.

Genetically engineered plants comprising one or multiple insect pest-resistant genes expressing one or multiple toxins are already known, and some of these genetically engineered plants are already on the market. Examples of such genetically engineered plants include YieldGard (a trademark). corn to express CrylAb toxin), YieldGard Rootworm (trademark) (a variety of corn to express Cry3Bb1 toxin), YieldGard Plus (trademark) (a variety of corn to express CrylAb and Cry3Bb1 toxins), Herculex I (trademark) ( a variety of maize to express phosphinothricin N-acetyl transferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (trademark) (a cotton variety to express CrylAc toxin), Bollgard I (trademark) (one cotton variety to express toxin CrylAc), Bollgard II (trademark) (a cotton variety to express toxin inas CrylAc and Cry2Ab), VIPCOT (trademark) (a variety of cotton to express VIP toxin), NewLeaf (trademark) (a variety of potato to express Cry3A toxin), NatureGard (trademark), Agrisu-re (trademark) ) GT Advantage (GA21 glyphosate resistant trait), A-grisure (registered trademark) CB Advantage (corn borer (CB) trait Bt11), and Protecta (registered trademark).

The aforementioned "plants" also include crops produced using a genetic engineering technique that have the ability to generate selectively acting antipathogenic substances.

One PR protein and others are known as antipathogenic substances (PRPs, EP-A-0 392 225). Such antipathogenic substances and genetically modified crops that generate them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191, and others.

Examples of such antipathogenic substances expressed in genetically modified crops include: ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (KP1, KP4 and KP6 and other toxins, which are produced by viruses, are known); stilbene synthetase; bibenzyl synthetase; chitinase; glucanase; a PR protein; and antipathogenic substances generated by microorganisms such as an antibiotic peptide, a hetero ring antibiotic, a plant disease resistance-associated protein factor (which is called a plant disease resistant gene and is described in WO 03/000906 ). Such antipathogenic substances and genetically engineered plants producing such substances are described in EP-A-0392225, W095 / 33818, EP-A-0353191, and others. The aforementioned "plant" includes plants to which advantageous characters, such as improved characters for oily material ingredients or enhanced amino acid content characters, have been conferred by genetic engineering technology. Examples include reduced VIS linolenic soybean (trademark) with reduced linolenic content or high lysine (high oil) corn (increased lysine or oil corn).

Also included are cumulative varieties in which a plurality of advantageous characters are combined, such as the above-mentioned classic herbicide characters, herbicide tolerance genes, weed resistance genes, antipathogenic substance producing genes, characters improved for oily material ingredients or characters with enhanced amino acid content.

Examples Although the present invention is more specifically described by way of formulation examples, seed treatment examples and test examples to follow, the present invention is not limited to the following examples. In the following examples, part represents part by weight unless particularly indicated otherwise. 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 Cahn-Ingold-Prelog order rule, and is represented by the following formula (1a). Compound (1b) is a compound represented by formula (1), wherein X 1 is a methyl group, X 2 is a methylamino group, and X 3 is a 2,5-dimethylphenyl group, and the compound is a racemic body and represented by the following formula (1b) Formulation Example 1 2.5 parts of compound (1a) or compound (1b), 1.25 parts of etaboxam, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecyl benzene sulfonate are completely mixed and 76.25 parts xylene to obtain the respective emulsions.

Formulation Example 2 Five (5) parts of compound (1a) or compound (1b), 5 parts of etaboxam, 35 parts of a mixture of hydrated silicon dioxide and a polyoxyethylene alkyl ether sulfate ammonium 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 fluid formulations.

Formulation Example 3 Five (5) parts of compound (1a) or compound (1b), 10 parts etaboxam, 1.5 parts sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts 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 magnesium aluminum silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is homogenized by stirring to obtain the respective fluid formulations.

Formulation Example 4 Five (5) parts of compound (1a) or compound (1b), 20 parts of etaboxam, 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, 35 parts of an aqueous solution containing 0.05 parts xanthan gum and 0.1 parts magnesium aluminum silicate are added to the resulting mixture, and 10 parts propylene glycol are also added thereto. The obtained mixture is homogenized by stirring to obtain the respective fluid formulations.

Formulation example 5 Forty (40) parts compound (1a) or compound (1b), 5 parts etaboxam, 5 parts propylene glycol (manufactured by Nacalai Tesque), 5 parts SoprophorFLK (manufactured by Rhodia Nikka), 0 , 2 part of an antiform emulsion C (manufactured by Dow Cornhoing), 0.3 part of proxx GXL (manufactured by Arch Chemicals) and 49.5 parts of ion exchange water are mixed to give a crude suspension. 150 parts of glass globules (diameter = 1 mm) are added to 100 parts of the suspension, and the suspension is crushed for 2 hours while cooling with cooling water. After trituration, the resultant is filtered to remove the glass globules, and the respective fluid formulations are obtained.

Formulation Example 6 Fifty (50) parts compound (1a) or compound (1b), 0.5 parts etaboxam, 38.5 parts NN kaolin clay (manufactured by Ta-kehara Chemical Industrial), 10 parts MorwetD425 and 1.5 parts Mor-werEFW (manufactured by Akzo Nobel Corp.) are mixed to obtain a premix A1. This premix is ground with a jet mill to obtain the respective powders.

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

Formulation Example 8 One (1) part compound (1a) or compound (1b), 40 parts etaboxam, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide they are completely ground and mixed to obtain the respective humectable powders.

Formulation Example 9 One (1) part compound (1a) or compound (1b), 2 parts etaboxam, 87 parts kaolin clay and 10 parts talc are thoroughly ground and mixed to obtain the respective powders.

Formulation Example 10 Two (2) parts compound (1a) or compound (1b), 0.25 parts etaboxam, 14 parts polyoxyethylene styrylphenyl ether, 6 parts calcium dodecyl benzene sulfonate and 77.75 parts xylene are thoroughly mixed to obtain the respective emulsions.

Formulation Example 11 Ten (10) parts of compound (1a) or compound (1b), 2.5 parts of etaboxam, 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 magnesium aluminum silicate are added to the crushed solution, and 10 parts propylene glycol are also added thereto. The obtained mixture is homogenized by stirring to obtain the respective fluid formulations.

Formulation Example 12 One (1) part compound (1a) or compound (1b), 20 parts etaboxam, 1 part synthetic hydrated silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 47 parts of kaolin clay are ground and mixed, and the resulting mixture is added with water and completely kneaded, and then subjected to granulation and drying to obtain the respective granules.

Formulation Example 13 Forty (40) parts compound (1a) or compound (1b), 1 part etaboxam, 3 parts calcium lignin sulfonate, 2 parts sodium lauryl sulfate and 54 parts synthetic hydrated silicon oxide They are completely ground and mixed to obtain the respective removable powders.

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

Seed Treatment Example 2 A fluid formulation prepared as in formulation example 2 is used for greasing treatment in an amount of 50 mL per 10 kg of dried rapeseed using a rotary seed treatment machine (seed coating). , produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 3 A fluid formulation prepared as in formulation example 3 is used for greasing treatment in an amount of 40 mL per 10 kg of dried corn seed using a rotary seed treatment machine (seed coating). , produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 4 Five (5) parts of a fluid formulation prepared as in formulation example 4,5 parts of BPD6135 pigment (manufactured by Sun Chemical) and 35 parts of water are mixed to prepare a mixture. The mixture is used for greasing treatment in an amount of 60 mL per 10 kg of dried rice seeds using a rotary seed treatment machine (seed coating produced by Hans-UIrich Hege GmbH) to obtain treated seeds. .

Seed Treatment Example 5 A powdered agent prepared as in formulation example 5 is used for powder coating treatment 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 1 is used for greasing treatment in an amount of 500 ml per 100 kg of dried beet seed using a rotary seed treatment machine (seed coating, produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed treatment example 7 A fluid formulation prepared as in formulation example 2 is used for greasing treatment in an amount of 50 mL per 10 kg of dried soybean seeds using a rotary seed treatment machine (seed coating). , produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 8 A fluid formulation prepared as in formulation example 3 is used for greasing treatment in an amount of 50 mL per 10 kg of dried wheat seeds using a rotary seed treatment machine (seed coating). , produced by Hans-UIrich Hege GmbH) to obtain treated seeds.

Seed treatment example 9 Five (5) parts of a fluid formulation prepared as in formulation example 4, 5 parts BPD6135 pigment (manufactured by Sun Chemical) and 35 parts water are mixed, and the resulting mixture is used for treatment. by greasing in an amount of 70 mL per 10 kg of potato tuber pieces using a rotary seed treatment machine (seed coating produced by Hans-Ulrich Hege GmbH) to obtain treated seeds.

Seed treatment example 10 Five (5) parts of a fluid formulation prepared as in formulation example 4, 5 parts BPD6135 pigment (manufactured by Sun Chemical) and 35 parts water are mixed, and the resulting mixture is used for treatment. by greasing in an amount of 70 mL per 10 kg of sunflower seeds using a rotary seed treatment machine (seed coater, produced by Hans-ülrich Hege GmbH) to obtain treated seeds.

Seed Treatment Example 11 A powder prepared as in formulation example 6 is used for powder coating treatment in an amount of 40 g per 10 kg of dried cotton seeds to obtain treated seeds.

Test Example 1 A plastic pot was filled with sandy soil, and then tomato (Patio) spread. The tomato was allowed to grow in a greenhouse for 20 days. A wetting powder of compound (1b) and a wetting powder of etaboxam were respectively diluted with water and then tank-mixed to prepare tank-mixed liquids containing compound (1b) and etaboxam at a predetermined concentration. The tank-mixed liquids were subjected to foliage application so that they could sufficiently adhere to the leaves of the tomato plants mentioned above. After application to the foliage, the plants were air dried. Thereafter, a suspension of Phytophthora infestans, the tomato mildew pathogen, was sprayed onto the leaf surface of tomato plants to inoculate the pathogen. They were placed at 20 to 22 ° C under high humidity for one night after inoculation, grown in a greenhouse for 5 days and after that the control effect was verified.

By comparison, the respective humectable powders described above were diluted with water to a predetermined concentration to prepare the liquids of compound (1b) and an etaboxam liquid, respectively, and were subjected to a similar disease control test. To calculate the control value, the incidence of disease was also determined in case the plants had not been treated with the agent. The relative incidence of disease in each treated area was determined as the incidence of disease in the area, considering that the incidence of disease in the untreated area was 100, and the control value was calculated by Equation 1 based on the incidence. of disease thus determined. Results are shown in Table 2. "Equation 1"; Control value = 100 (A - B) / AA: Incidence of plant disease in untreated area B: Incidence of plant disease in treated area Generically, the expected control value for the case where data two types of compounds active ingredient are mixed and used for treatment, the so-called control value expectation is calculated with the following Colby calculation equation. "Equation2"; E = X + Y- (XxY) / 100 X: Control value (%) when active ingredient compound A is used for treatment in M ppm or M g per 100 kg of seeds Y: Control value (%) when active ingredient compound B is used for treatment at N ppm or N g per 100 kg of seeds E: Control value (%) expected for case active ingredient A compound at M ppm or M g per 100 kg of seeds and the active ingredient compound B in N ppm or N g per 100 kg of seeds are mixed and used for treatment (hereinafter referred to as "control value expectation") "Synergistic effect (%) "= (Actual Control Value) x 100 / (Control Value Expectation) Table 2 Test Example 2 An acetone solution of compound (1b) and an acetone solution of etaboxam were mixed to prepare mixed liquids containing compound ( 1b) and etaboxam at a predetermined concentration. These mixed liquids were adhered to the surface of cucumber seeds (Sagamihanjiro) and allowed to stand overnight to obtain treated seeds. A plastic pot was filled with sandy soil, and the treated seeds were scattered over it. Then the seeds were covered with sandy soil that had been mixed with a medium bran on which Pythium ultimum, the pathogen of cucumber seedling wilt, was grown. They were irrigated and allowed to grow at 18 ° C under humidity for 13 days and after that the control effect was verified. Disease incidence was calculated by Equation 3, and the control value was calculated by Equation 1 based on disease incidence.

By comparison, acetone solutions containing compound (1b) at the predetermined concentration and an acetone solution containing etaboxam at the predetermined concentration were prepared and subjected to similar tests. "Equation 3" Disease Incidence = (Number of nonemerging seedlings and number of seedlings where disease development has been observed) x 100 / (Total number of seeds disseminated) Results are shown in Table 3.

Table 3_________________ Test Example 3 A plastic pot was filled with sandy soil, and grape (Bago A) was then disseminated. The grape was grown in a greenhouse for 40 days. A wetting powder of compound (1b) and a wetting powder of etaboxam were respectively diluted with water and then tank-mixed to prepare tank-mixed liquids containing compound (1b) and etaboxam at a predetermined concentration. The tank mixed liquids were subjected to foliage application so that they could sufficiently adhere to the underside of the above mentioned grape plant leaves. After application to the foliage, the plants were air dried. After that, an aqueous suspension of Plasmopara viticola sporangia, a pathogen from vine mildew, was sprayed onto grape plants to inoculate the pathogen. They were placed at 23 ° C under high humidity for one day after inoculation, grown in a greenhouse at 23 ° C for 5 days. After that, the grape plants were placed at 23 ° C under high humidity for one day, and the infected area was verified.

By comparison, the respective humectable powders described above were diluted with water to a predetermined concentration to prepare the liquids of compound (1b) and an etaboxam liquid, respectively, and were subjected to a similar disease control test. To calculate the control value, the incidence of disease was also determined in case the plants had not been treated with the agent. The relative incidence of disease in each treated area was determined as the incidence of disease in the area, considering that the incidence of disease in the untreated area was 100, and the control value was calculated by Equation 1 based on the incidence. of disease thus determined. The results are shown in Table 4. Industrial Applicability In accordance with the present invention, a composition for the control of highly active plant diseases and a method for effectively controlling plant diseases can be provided.

Claims (4)

1, A composition for the control of plant diseases, characterized in that it comprises, as active ingredients, a compound represented by the formula (1): wherein X1 represents a methyl group; X 2 represents a methylamino group; and X 3 represents a 2,5-dimethylphenyl group; and etaboxam, which has a weight ratio of the compound represented by formula (1) to etaboxam within the range of 1: 2 to 125: 1. Seed treatment agent, characterized in that it comprises, as active ingredients, the compound represented by the formula (1) as defined in claim 1 and etaboxam, which has a weight ratio of the compound represented by the formula (1) to etaboxam within the range of 1: 2 to 125: 1. Method for the control of plant diseases, characterized in that it comprises applying to a plant or the place where a plant is grown effective amounts of the compound represented by formula (1) as defined in claim 1 and 3. etaboxam, which has a weight ratio of the compound represented by the formula {1} to etaboxam within the range of 1: 2 to 125: 1. Combined use of the compound represented by formula (1) as defined in claim 1 and etaboxam, which has a weight ratio of the compound represented by formula (1) to etaboxam within the range 1: 2 to 125: 1, characterized by fact that is in the control of plant diseases.