WO2014013842A1 - 植物病害防除組成物およびその用途 - Google Patents
植物病害防除組成物およびその用途 Download PDFInfo
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- WO2014013842A1 WO2014013842A1 PCT/JP2013/067160 JP2013067160W WO2014013842A1 WO 2014013842 A1 WO2014013842 A1 WO 2014013842A1 JP 2013067160 W JP2013067160 W JP 2013067160W WO 2014013842 A1 WO2014013842 A1 WO 2014013842A1
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- Prior art keywords
- present
- compound
- composition
- carboxamide compound
- formula
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- PDPWCKVFIFAQIQ-UHFFFAOYSA-N Cc1ccc(C)c(OCc2c(C(C(NC)=O)OC)cccc2)c1 Chemical compound Cc1ccc(C)c(OCc2c(C(C(NC)=O)OC)cccc2)c1 PDPWCKVFIFAQIQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
Definitions
- the present invention relates to a plant disease control composition and its use.
- Patent Documents 1 and 2 Conventionally, many compounds have been developed and put into practical use for controlling plant diseases (see, for example, Patent Documents 1 and 2).
- An object of the present invention is to provide a composition having an excellent control effect against plant diseases.
- the plant disease control composition of the present invention (hereinafter referred to as the present composition) has the formula (I) [Wherein, R 1 and R 2 represent the same meaning as described above. ]
- a carboxamide compound represented by the following (hereinafter referred to as the present carboxamide compound) and formula (A) (Hereinafter referred to as the present compound (A)).
- the present carboxamide compound is, for example, a compound described in International Publication No. 86/02641 pamphlet and International Publication No. 92/12970 pamphlet, and can be produced by the methods described therein.
- the present carboxamide compound has one asymmetric carbon, and the formula (IR) based on the asymmetric carbon [Wherein, R 1 and R 2 represent the same meaning as described above. ]
- S-form represented by the formula, but in the present invention, any enantiomeric ratio can be used for the present carboxamide compound.
- the present carboxamide compound include the following.
- a carboxamide compound represented by the formula (1) (hereinafter referred to as the present carboxamide compound (1)); A carboxamide compound represented by the formula (1R) (hereinafter referred to as the present carboxamide compound (1R)); A carboxamide compound represented by the formula (2) (hereinafter referred to as the present carboxamide compound (2)); A carboxamide compound represented by the formula (2R) (hereinafter referred to as the present carboxamide compound (2R)); A carboxamide compound represented by the formula (3) (hereinafter referred to as the present carboxamide compound (3)); A carboxamide compound represented by the formula (3R) (hereinafter referred to as the present carboxamide compound (3R)); A carboxamide compound represented by the formula (4) (hereinafter referred to as the present carboxamide compound (4)); as well as, A carboxamide compound represented by the formula (5) (hereinafter referred to as the present carboxamide compound (5)).
- a carboxamide compound represented by the formula (1) (her
- This compound (A) is a known compound and is described in, for example, International Publication No. 02/10101 pamphlet. This compound (A) is compoundable by a well-known method.
- this compound (A) has one asymmetric carbon, and R isomer based on the asymmetric carbon (the following formula (A1)) Indicated by ) And S form (the following formula (A2) Indicated by Both enantiomers of) are present, but in the present invention, those having an arbitrary enantiomeric ratio can be used for the present compound (A).
- the enantiomer can be synthesized by the method described in WO 02/10101.
- the composition of the present invention may be a mixture of the present carboxamide compound and the present compound (A) itself, but the present composition is usually prepared by mixing the present carboxamide compound, the present compound (A) and an inert carrier. Accordingly, surfactants and other formulation adjuvants are added to formulate oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like. Such a preparation can be used as a plant disease control agent as it is or with addition of other inactive ingredients.
- the present composition contains the present carboxamide compound and the present compound (A) in a total amount of usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight. .
- solid carriers used in formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut shell powder, etc.
- Natural organic materials synthetic organic materials such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular materials made of synthetic inorganic materials such as synthetic silicon hydroxide, etc.
- liquid carriers include, for example, xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, 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 fats Group hydrocarbon , Esters, dimethyl sulfoxide, acetonitrile and water.
- surfactants include anionic interfaces such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like.
- Nonionic surfactants such as activators and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
- adjuvants for preparation examples include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol Inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.
- water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol Inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.
- composition of the present invention is also prepared by formulating the present carboxamide compound and the present compound (A) by the above-described method, and then diluting with water as necessary to prepare a formulation containing the present carboxamide compound and the present compound ( It can also be prepared by mixing a preparation containing A) or a diluted solution thereof.
- composition of the present invention can be used to protect plants from plant diseases.
- Examples of plant diseases for which the composition of the present invention has a controlling effect include the following.
- Rice diseases rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuruoi).
- Wheat diseases powdery mildew (Erysiphe graminis), red mold disease (Fusarium gramaminerum, F. avenacerum, F. culmorum, Microdochium nitrid, red rust (Puccinia isp.
- Ustilago nuda Ustilago nuda
- cloud disease Rhynchosporium secalis
- reticular disease Pyrenophora teres
- spot disease Cochliobolus sativus
- leafy leaf disease Pyrenophora graminea
- Rhizonia a Diseases of corn: smut (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrohus), leprosy (Gloeocercospora sorgi), southern rust (Puccinia polysora), gray leaf spot disease Rhizoctonia solani due to seedling.
- Oyster diseases Anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae). Diseases of cucurbits: Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella meloniis), vine warp (Fusarium oxysporum), por disease (u) ), Seedling blight (Pythium sp.); Diseases of tomato: Alternaria solani, leaf mold (Cladosporium fulvum), plague (Phytophthora infestans).
- Pea disease powdery mildew (Erysiphe pisi). Potato diseases: Alternaria solani, Phytophthora infestans, Sputum rot septica, Spongosporia subteranean f. Strawberry disease: powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella singulata). Tea diseases: net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), ring spot disease (Pestalotiosis sp.), Anthracnose (Colletotrichum theae-sinensis).
- Tobacco disease Alternaria longipes, powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), epidemic (Phytophyti. Rapeseed diseases: Sclerotinia sclerotiorum, Rhizoctonia solani, and Rhizoctonia solani. Cotton disease; Rhizoctonia solani caused by Rhizoctonia spp. Diseases of sugar beet: brown spot disease (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides).
- Rose diseases black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), downy mildew (Peronospora sparsa).
- Diseases of chrysanthemum and asteraceae vegetables downy mildew (Bremia lactucae), brown spot disease (Septoria chrysanthemi-indici), white rust (Puccinia horiana).
- Diseases of various crops Diseases caused by Pythium spp.
- Aspergillus genus Penicillium genus, Fusarium genus, Gibberella genus, Tricoderder genus, Thielaviopsis genus, Rhizopus genus, Mucor genus, Corticium genus, Phoma genus, Rhizoctonia genus Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
- Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
- Vegetables Eggplant vegetables (eggplant, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelon, melon, squash, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, USA Bowfish, etc.), red crustacean vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yam, taros, etc.
- Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
- the above-mentioned plant may be a plant imparted with resistance by genetic recombination technology.
- soybean diseases that are expected to have particularly high efficacy include Rhizoctonia solani, purpura (Cercospora kikuchii), brown spot ( Septoriaglycines, Corynespora caicicola, Rust (Phakopsora pachyrhizi), Sclerotinia sclerotiorum, Spot disease (Cercospora sojina) Etc.
- composition comprising the present carboxamide compound (1) and the present compound (A); A composition comprising the present carboxamide compound (1R) and the present compound (A); A composition comprising the present carboxamide compound (2) and the present compound (A); A composition comprising the present carboxamide compound (2R) and the present compound (A); A composition comprising the present carboxamide compound (3) and the present compound (A); A composition comprising the present carboxamide compound (3R) and the present compound (A); A composition comprising the present carboxamide compound (4) and the present compound (A); A composition comprising the present carboxamide compound (5) and the present compound (A);
- a composition comprising the present carboxamide compound (1) and the present compound (A) in a weight ratio of the present carboxamide compound (1) / the present compound (A) 0.1 / 1 to 10/1;
- a composition comprising the present carboxamide compound (1R) and the present compound (A) in a weight ratio of the present carboxamide compound (1) / the present compound (A) 0.1 / 1 to 10/1;
- a composition comprising the present carboxamide compound (2) and the present compound (A) at a weight ratio of the present carboxamide compound (2) / the present compound (A) 0.1 / 1 to 10/1;
- a composition comprising the present carboxamide compound (2R) and the present compound (A) in a weight ratio of the present carboxamide compound (2) / the present compound (A) 0.1 / 1 to 10/1;
- a composition comprising the present carboxamide compound (3) and the present compound (A) in a weight ratio of the present carboxamide compound (3) / the present compound (A) 0.1 / 1 to 10/1;
- the plant disease control method of the present invention (hereinafter referred to as the present invention control method) is carried out by treating an effective amount of the present carboxamide compound and the present compound (A) on the plant or the soil where the plant is cultivated.
- Such plants include, for example, plant foliage, plant seeds and plant bulbs.
- a bulb means here a bulb, a bulb, a rhizome, a tuber, a tuberous root, and a root support body.
- the present carboxamide compound and the present compound (A) may be separately treated in the same period on the plant or the soil where the plant is cultivated, but the composition of the present invention is usually used from the viewpoint of simplicity during the treatment. It is processed as a thing.
- examples of the treatment method of the present carboxamide compound and the present compound (A) include foliage treatment, soil treatment, root treatment and seed treatment.
- foliage treatment examples include a method of treating the surface of a plant being cultivated by foliage spraying and tree trunk spraying.
- soil treatment include soil application, soil mixing, and chemical irrigation into soil.
- root treatment examples include a method of immersing the whole plant or root in a chemical solution containing the present carboxamide compound and the present compound (A), and the present carboxamide compound, the present compound (A) and a solid carrier. And a method of attaching the solid preparation to the root of a plant.
- seed treatment includes, for example, treatment of the seed or bulb of a plant to be protected from plant diseases, and specifically, for example, a seed of a suspension of the composition of the present invention is made into a mist.
- Immersion treatment for immersing seeds for a certain period of time, film coating treatment for film-coating the seed surface by mixing the composition of the present invention and a polymer, pellets for mixing the composition of the present invention and powder and forming the seeds into a pellet A coating process is mentioned.
- the treatment amount of the present carboxamide compound and the present compound (A) is the kind of plant to be treated, the kind and occurrence frequency of the plant disease to be controlled, the formulation form, the treatment time, the treatment method, the treatment place.
- the total amount of the present carboxamide compound and the present compound (A) is usually 1 to 1000 m 2. It is 500 g, preferably 2 to 200 g, more preferably 10 to 100 g.
- the amount of the present carboxamide compound and the present compound (A) treated in the seed treatment is the total amount of the present carboxamide compound and the present compound (A), and is usually 0.001 to 10 g, preferably 0, per 1 kg of seed. .01 to 1 g.
- Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying.
- the concentration of the present carboxamide compound and the present compound (A) is the total concentration of the present carboxamide compound and the present compound (A), and is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight. It is. Powders, granules, etc. are usually processed without dilution.
- Reference production example 1 (R) -1,1,3-trimethyl-4-aminoindane (optical purity 99% ee) 0.15 g, triethylamine 0.13 g, 4-dimethylaminopyridine 5 mg, and THF 1 mL were added under ice cooling.
- Reference production example 5 Racemic 1,1,3-trimethyl-4-aminoindane (300 g), D-tartaric acid (128 g) and methanol (260 ml) were mixed and incubated at 70 ° C. for 1 hour. Subsequently, the mixture was allowed to cool to room temperature, and about 0.1 g of seed crystals were mixed and left for 2 days. The produced solid was filtered off and washed with methanol. The obtained solid was recrystallized five times from methanol to obtain 100 g of 1,1,3-trimethyl-4-aminoindane D-tartrate.
- a part represents a weight part.
- Formulation Example 1 2.5 parts of any of the present carboxamide compounds (1) to (5), 1.25 parts of the present compound (A), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and xylene Each formulation is obtained by thoroughly mixing 76.25 parts.
- Formulation Example 2 2 parts of any of the present carboxamide compounds (1) to (5), 8 parts of the present compound (A), 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and Each formulation is obtained by mixing 55 parts of water and pulverizing with a wet pulverization method.
- Formulation Example 3 28.5 parts of an aqueous solution containing 5 parts of any of the present carboxamide compounds (1) to (5), 10 parts of the present compound (A), 1.5 parts of sorbitan trioleate and 2 parts of polyvinyl alcohol. After mixing and pulverizing by a wet pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is added and stirred. Mix to obtain each formulation.
- Formulation Example 4 1 part of any one of the present carboxamide compounds (1) to (5), 4 parts of this compound (A), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay After pulverizing and mixing, adding water and kneading well, each formulation is obtained by granulating and drying.
- Formulation Example 5 12.5 parts of any of the present carboxamide compounds (1) to (5), 37.5 parts of this compound (A), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
- Formulation Example 6 A formulation is obtained by thoroughly pulverizing and mixing 3 parts of any of the present carboxamide compounds (1) to (5), 2 parts of the present compound (A), 85 parts of kaolin clay and 10 parts of talc.
- Test example 1 Using a rotary seed processing machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), 100 g of a cyclohexanone solution containing a predetermined weight of the test compound was applied to 10 g of soybean (variety; natto small grains) seeds.
- soybean varietyer
- soil contaminated with Rhizoctonia solani was packed in a plastic pot, seeds treated with the test compound were sown, and cultivated in a glass greenhouse for 20 days.
- the presence or absence of Rhizotonia solani disease caused by Rhizoctonia spp. was observed in seedlings sprouting from various offsprings, and the disease incidence was determined by the following formula (1).
- the soybean seeds that were not subjected to the above-described smearing treatment were cultivated in the same manner as the treated section (this is referred to as “untreated section”). And the disease incidence was calculated
- the carboxamide compound represented by the formula (I) used in Test Example 1 and the compound represented by the formula (A) used in Test Example 1 were both racemic mixtures.
- the efficacy of the treated area was determined by the following formula (2) from the disease incidence of the treated area and the untreated area. The results are shown in [Table 1] and [Table 2].
- the plants were air-dried, and one day later, they were spray-inoculated with an aqueous suspension (about 10,000 / ml) of summer spore of soybean rust (Phakopsora pachyrhizi). After inoculation, it was first placed at 20 to 23 ° C under high humidity for 1 day, and further cultivated in a greenhouse for 10 days (this is referred to as a treatment zone). Thereafter, the lesion area of soybean rust (Phakopsora pachyrhizi) was investigated. On the other hand, soybeans were cultivated in the same manner as in the treated group except that the diluted solution of the test compound was not sprayed on the foliage (this is referred to as the untreated group).
- the lesion area of soybean rust (Phakopsora pachyrhizi) was investigated in the same manner as in the treatment section.
- the carboxamide compound represented by the formula (I) used in Test Example 2 and the compound represented by the formula (A) used in Test Example 2 were both racemic mixtures.
- the efficacy of the treated area was determined by the following formula (3) from the lesion areas of the treated area and the untreated area. The results are shown in [Table 3] and [Table 4].
- Test example 3 Using a rotary seed processor (seed dresser, manufactured by Hans-Ulrich Hege GmbH), 100 g of a cyclohexanone solution containing a predetermined weight of the test compound is applied to 10 g of soybean (variety; natto grains) seeds.
- soybean variety; natto grains
- a treatment zone soil contaminated with Rhizoctonia solani
- seeds treated with the test compound are sown and cultivated in a glass greenhouse for 20 days (this is referred to as a treatment zone).
- the soybean seeds that have not been subjected to the above-described smearing treatment are cultivated in the same manner as the treated section (this is referred to as an untreated section). Then, the disease incidence is obtained in the same manner as in the treatment area.
- the carboxamide compound represented by the formula (I) used in Test Example 3 is a mixture of R form: S form 80:20 to 100: 0, more preferably R form: S form 95: 5 to 99: 1. Is used.
- the compound represented by the formula (A) used in Test Example 3 is a racemic mixture.
- the efficacy of the treated area is determined from the incidence of each of the treated area and the untreated area by the following formula (5). As a result, high efficacy can be obtained in the treatment section treated with the present composition.
Abstract
Description
すなわち、本発明は以下の通りである。
[1] 式(I)
〔式中、
R1は水素原子又はメチル基を表し、
R2はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
で示されるカルボキサミド化合物と式(A)で示される化合物とを含有する植物病害防除組成物。
式(A):
[3] 式(I)
〔式中、
R1は水素原子又はメチル基を表し、
R2はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
で示されるカルボキサミド化合物と式(A)で示される化合物との有効量を、植物又は植物を栽培する土壌に処理する工程を含む植物病害防除方法。
式(A):
[4] カルボキサミド化合物と式(A)で示される化合物との重量比が、カルボキサミド化合物/式(A)で示される化合物=0.1/1~10/1である[3]記載の植物病害防除方法。
[5] 植物又は植物を栽培する土壌が、ダイズ又はダイズを栽培する土壌である[3]又は[4]記載の植物病害防除方法。
〔式中、R1及びR2は前記と同じ意味を表す。〕
で示されるカルボキサミド化合物(以下、本カルボキサミド化合物と記す。)と式(A)
で示される化合物(以下、本化合物(A)と記す。)とを含有する。
〔式中、R1及びR2は前記と同じ意味を表す。〕
で示されるR体と、
式(I−S)
〔式中、R1及びR2は前記と同じ意味を表す。〕
で示されるS体の両エナンチオマーが存在するが、本発明では任意のエナンチオマー比であるものを本カルボキサミド化合物に用いることができる。
式(1)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(1)と記す。);
式(1R)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(1R)と記す。);
式(2)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(2)と記す。);
式(2R)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(2R)と記す。);
式(3)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(3)と記す。);
式(3R)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(3R)と記す。);
式(4)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(4)と記す。);
及び、
式(5)で示されるカルボキサミド化合物(以下、本カルボキサミド化合物(5)と記す。)。
で示される。)及びS体(下記式(A2)
で示される。)の両エナンチオマーが存在するが、本発明では任意のエナンチオマー比であるものを本化合物(A)に用いることができる。
該エナンチオマーは、国際公開第02/10101号パンフレットに記載の方法により合成することができる。
本発明組成物には、本カルボキサミド化合物及び本化合物(A)が合計で、通常0.1~99重量%、好ましくは0.2~90重量%、より好ましくは1~80重量%含有される。
界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルアリールスルホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエチレンアルキルアリールエーテルリン酸エステル塩、リグニンスルホン酸塩、ナフタレンスルホネートホルムアルデヒド重縮合物等の陰イオン界面活性剤及びポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルポリオキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル等の非イオン界面活性剤、及びアルキルトリメチルアンモニウム塩等の陽イオン界面活性剤が挙げられる。
その他の製剤用補助剤としては、例えばポリビニルアルコール、ポリビニルピロリドン等の水溶性高分子、アラビアガム、アルギン酸及びその塩、CMC(カルボキシメチルセルロ−ス)、キサンタンガム等の多糖類、アルミニウムマグネシウムシリケート、アルミナゾル等の無機物、防腐剤、着色剤及びPAP(酸性リン酸イソプロピル)、BHT等の安定化剤が挙げられる。
イネの病害:いもち病(Magnaporthe grisea)、ごま葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)。
コムギの病害:うどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenacerum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P. graminis、P. recondita)、紅色雪腐病(Micronectriella nivale)、雪腐小粒菌核病(Typhula sp.)、裸黒穂病(Ustilago tritici)、なまぐさ黒穂病(Tilletia caries)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Mycosphaerella graminicola)、ふ枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici−repentis)。
オオムギの病害:うどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenacerum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P.graminis、P.hordei)、裸黒穂病(Ustilago nuda)、雲形病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)。
トウモロコシの病害:黒穂病(Ustilago maydis)、ごま葉枯病(Cochliobolus heterostrophus)、ひょう紋病(Gloeocercospora sorghi)、南方さび病(Puccinia polysora)、グレイリーフスポット病(Cercospora zeae−maydis) 、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)。
リンゴの病害:モニリア病(Monilinia mali)、腐らん病(Valsaceratosperma)、うどんこ病(Podosphaera leucotricha)、斑点落葉病(Alternaria alternata apple pathotype)、黒星病(Venturia inaequalis)、炭そ病(Colletotrichum acutatum)、疫病(Phytophthora cactorum)。
ナシの病害:黒星病(Venturia nashicola, V. pirina)、黒斑病(Alternaria alternata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum)、疫病(Phytophthora cactorum);
モモの病害:灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、フォモプシス腐敗病(Phomopsis sp.)。
ブドウの病害:黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata)、うどんこ病(Uncinula necator)、さび病(Phakopsora ampelopsidis)、ブラックロット病(Guignardia bidwellii)、べと病(Plasmopara viticola)。
カキの病害:炭そ病(Gloeosporium kaki)、落葉病(Cercospora kaki, Mycosphaerella nawae)。
ウリ類の病害:炭そ病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Mycosphaerella melonis)、つる割病(Fusarium oxysporum)、べと病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.);
トマトの病害:輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、疫病(Phytophthora infestans)。
ナスの病害:褐紋病(Phomopsis vexans)、うどんこ病(Erysiphe cichoracearum)。
アブラナ科野菜の病害:黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根こぶ病(Plasmodiophora brassicae)、べと病(Peronospora parasitica)。
ネギの病害:さび病(Puccinia allii)、べと病(Peronospora destructor)。
インゲンの病害:炭そ病(Colletotrichum lindemthianum)。
ラッカセイの病害:黒渋病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii)。
エンドウの病害:うどんこ病(Erysiphe pisi)。
ジャガイモの病害:夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、緋色腐敗病(Phytophthora erythroseptica)、粉状そうか病(Spongospora subterranean f. sp. subterranea)。
イチゴの病害:うどんこ病(Sphaerotheca humuli)、炭そ病(Glomerella cingulata)。
チャの病害:網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭そ病(Colletotrichum theae−sinensis)。
タバコの病害:赤星病(Alternaria longipes)、うどんこ病(Erysiphe cichoracearum)、炭そ病(Colletotrichum tabacum)、べと病(Peronospora tabacina)、疫病(Phytophthora nicotianae)。
ナタネの病害:菌核病(Sclerotinia sclerotiorum)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)。
ワタの病害;リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)。
テンサイの病害:褐斑病(Cercospora beticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黒根病(Aphanomyces cochlioides)。
バラの病害:黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa)、べと病(Peronospora sparsa)。
キクおよびキク科野菜の病害:べと病(Bremia lactucae)、褐斑病(Septoria chrysanthemi−indici)、白さび病(Puccinia horiana)。
種々の作物の病害:ピシウム属菌によって引き起こされる病害(Pythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulare, Pythium ultimum)、灰色かび病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum)。
ダイコンの病害:黒斑病(Alternaria brassicicola)。
シバの病害:ダラースポット病(Sclerotinia homeocarpa)、ブラウンパッチ病およびラージパッチ病(Rhizoctonia solani)。
バナナの病害:シガトカ病(Mycosphaerella fijiensis、Mycosphaerella musicola)。
ヒマワリの病害:べと病(Plasmopara halstedii)。
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、およびDiplodia属菌等によって引き起こされる、各種作物の種子病害または生育初期の病害。
Polymixa属またはOlpidium属等によって媒介される各種作物のウイルス病。
農作物;トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等、
野菜;ナス科野菜(ナス、トマト、ピーマン、トウガラシ、ジャガイモ等)、ウリ科野菜(キュウリ、カボチャ、ズッキーニ、スイカ、メロン、スカッシュ等)、アブラナ科野菜(ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等)、キク科野菜(ゴボウ、シュンギク、アーティチョーク、レタス等)、ユリ科野菜(ネギ、タマネギ、ニンニク、アスパラガス)、セリ科野菜(ニンジン、パセリ、セロリ、アメリカボウフウ等)、アカザ科野菜(ホウレンソウ、フダンソウ等)、シソ科野菜(シソ、ミント、バジル等)、イチゴ、サツマイモ、ヤマノイモ、サトイモ等、
花卉、
観葉植物、
シバ、
果樹;仁果類(リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等)、核果類(モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等)、カンキツ類(ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等)、堅果類(クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等)、液果類(ブルーベリー、クランベリー、ブラックベリー、ラズベリー等)、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
果樹以外の樹;チャ、クワ、花木、街路樹(トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ)等。
また、これらの作物に発生する植物病害のうち、特に高い効力が期待されるダイズの病害としては、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)、紫斑病(Cercospora kikuchii)、褐紋病(Septoriaglycines)、褐色輪紋病(Corynespora caciicola)、さび病(Phakopsora pachyrhizi)、菌核病(Sclerotinia sclerotiorum)、斑点病(Cercospora sojina);
等が挙げられる。
本カルボキサミド化合物(1)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とエタボキサムと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とメタラキシルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とクロチアニジンと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とイミダクロプリドと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とイプコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とメトコナゾールと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)と4−オキソ−4−[(2−フェニルエチル)アミノ]−酪酸と本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とトルクロホスメチルと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とクロチアニジンとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(2R)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(3R)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(4)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(5)とイミダクロプリドとエタボキサムとメタラキシルMと本化合物(A)とを含有する組成物;
本カルボキサミド化合物(1R)と本化合物(A)とを本カルボキサミド化合物(1)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(2)と本化合物(A)とを本カルボキサミド化合物(2)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(2R)と本化合物(A)とを本カルボキサミド化合物(2)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(3)と本化合物(A)とを本カルボキサミド化合物(3)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(3R)と本化合物(A)とを本カルボキサミド化合物(3)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(4)と本化合物(A)とを本カルボキサミド化合物(4)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物;
本カルボキサミド化合物(5)と本化合物(A)とを本カルボキサミド化合物(5)/本化合物(A)=0.1/1~10/1の重量比で含有する組成物。
かかる土壌処理としては、例えば、土壌散布、土壌混和及び土壌への薬液潅注が挙げられる。
かかる根部処理としては、例えば、本カルボキサミド化合物と本化合物(A)とを含有する薬液に植物の全体又は根部を浸漬する方法、及び、本カルボキサミド化合物と本化合物(A)と固体担体とを含有する固体製剤を植物の根部に付着させる方法が挙げられる。
かかる種子処理としては、例えば、植物病害から保護しようとする植物の種子又は球根への本発明組成物の処理が挙げられ、詳しくは、例えば本発明組成物の懸濁液を霧状にして種子表面若しくは球根表面に吹きつける吹きつけ処理、本発明組成物の水和剤、乳剤若しくはフロアブル剤に少量の水を加える若しくはそのままで、種子又は球根に塗布する塗沫処理、本発明組成物の溶液に一定時間種子を浸漬する浸漬処理、本発明組成物とポリマーを混和して種子表面をフィルムコートするフィルムコート処理、本発明組成物と粉体を混和し種子を核としてペレット状に成形するペレットコート処理が挙げられる。
乳剤、水和剤、フロアブル剤等は通常水で希釈して散布することにより処理する。この場合、本カルボキサミド化合物及び本化合物(A)の濃度は、本カルボキサミド化合物及び本化合物(A)の合計での濃度で、通常0.0005~2重量%、好ましくは0.005~1重量%である。粉剤、粒剤等は通常希釈することなくそのまま処理する。
まず、本カルボキサミド化合物(1R)、本カルボキサミド化合物(2R)および本カルボキサミド化合物(3R)の参考製造例を示す。
(R)−1,1,3−トリメチル−4−アミノインダン(光学純度99%ee)0.15g、トリエチルアミン0.13g、4−ジメチルアミノピリジン5mg、およびTHF1mLからなる溶液に、氷冷下で1−メチル−3−ジフルオロメチルピラゾール−4−カルボン酸クロライド0.17gのTHF溶液を滴下した。室温で15分間攪拌した後、反応混合物に氷水を加え、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄後、硫酸マグネシウムで乾燥し減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付して、(R)−(−)−N−(1,1,3−トリメチルインダン−4−イル)−1−メチル−3−ジフルオロメチルピラゾール−4−カルボン酸アミド(以下、本カルボキサミド化合物(2)と記す。)0.20g(光学純度99%ee)を得た。
本カルボキサミド化合物(2)
1H−NMR(CDCl3)δ:1.25(3H,s),1.28(3H,d,J=7.1Hz),1.34(3H,s),1.67(1H,dd,J=12.9,4.1Hz),2.24(1H,dd,J=12.9,8.5Hz),3.32−3.41(1H,m),3.94(3H,s),6.88(1H,t,J=54.1Hz),6.98(1H,d,J=7.6Hz),7.22−7.27(1H,m),7.79(1H,d,J=7.8Hz),7.96(1H,br s),8.02(1H,s).
[α]D 23=−62°(CHCl3,c0.99)
本カルボキサミド化合物(1)
1H−NMR(CDCl3)δ:1.25(3H,s),1.28(3H,d,J=7.1Hz),1.34(3H,s),1.67(1H,dd,J=12.8,4.3Hz),2.24(1H,dd,J=12.9,8.5Hz),3.29−3.37(1H,m),3.99(3H,s),7.00(1H,d,J=6.8Hz),7.23−7.27(1H,m),7.62(1H,br s),7.76(1H,d,J=7.8Hz),8.04(1H,s).
[α]D 23=−54°(CHCl3,c1.02)
参考製造例3
(R)−1,1,3−トリメチル−4−アミノインダン(光学純度99%ee)0.15g、トリエチルアミン0.13g、4−ジメチルアミノピリジン5mg、およびTHF1mLからなる溶液に、氷冷下で1,3,5−トリメチルピラゾール−4−カルボン酸クロライド0.15gのTHF溶液を滴下した。室温で15分間攪拌した後、反応混合物に氷水を加え、酢酸エチルで抽出した。有機層を飽和炭酸水素ナトリウム水溶液及び飽和食塩水で順次洗浄後、硫酸マグネシウムで乾燥し減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付して、(R)−(−)−N−(1,1,3−トリメチルインダン−4−イル)−1,3,5−トリメチルピラゾール−4−カルボン酸アミド(以下、本カルボキサミド化合物(3)と記す。)0.17g(光学純度99%ee)を得た。
本カルボキサミド化合物(3)
1H−NMR(CDCl3)δ:1.25(3H,s),1.32(3H,d,J=7.1Hz),1.34(3H,s),1.67(1H,dd,J=12.7,4.6Hz),2.24(1H,dd,J=12.9,8.5Hz),2.51(3H,s),2.53(3H,s),3.31−3.39(1H,m),3.76(3H,s),6.96(1H,d,J=7.6Hz),7.21−7.26(2H,m),7.76(1H,d,J=7.8Hz).
[α]D 23=−57°(CHCl3,c1.01)
HPLCを用いて、ラセミ体の1,1,3−トリメチル−4−アミノインダンの4.8gを下記の条件で両鏡像体に分離し、後のピークとして溶出した(R)−1,1,3−トリメチル−4−アミノインダン1.2g(光学純度99%ee)を得た。
カラム:CHIRACEL(登録商標) OD光学活性カラム
カラム温度:室温
移動相:ヘキサンと2−プロパノールとの混合溶媒(99:1)
流量:10mL/分
(R)−1,1,3−トリメチル−4−アミノインダン
[α]D 25=−33.7°(CHCl3,c0.61)
ラセミ体の1,1,3−トリメチル−4−アミノインダン300g、D−酒石酸128gおよびメタノール260mlを混合し、70℃で1時間保温した。ついで混合物を室温まで放冷し、約0.1gの種晶を混合し二日間放置した。生成した固体を濾別し、メタノールで洗浄した。得られた固体をメタノールから5回再結晶して1,1,3−トリメチル−4−アミノインダンD−酒石酸塩100gを得た。得られた1,1,3−トリメチル−4−アミノインダンD−酒石酸塩78gにpHが10以上となるまで5%水酸化ナトリウム水溶液を加え、メチルt−ブチルエーテルで3回抽出した。得られた油層を飽和食塩水で洗浄し飽和炭酸水素ナトリウム水溶液で順次洗浄後、硫酸ナトリウムで乾燥し減圧下濃縮して、1,1,3−トリメチル−4−アミノインダンのエナンチオマー比がR体/S体で99.6/0.4の混合物を38g得た。
本カルボキサミド化合物(1)~(5)のいずれかを2.5部、本化合物(A)を1.25部、ポリオキシエチレンスチリルフェニルエ−テル14部、ドデシルベンゼンスルホン酸カルシウム6部およびキシレン76.25部をよく混合することにより各製剤を得る。
本カルボキサミド化合物(1)~(5)のいずれかを2部、本化合物(A)を8部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物(重量割合1:1)35部および水55部を混合し、湿式粉砕法で微粉砕することにより各製剤を得る。
本カルボキサミド化合物(1)~(5)のいずれかを5部、本化合物(A)を10部、ソルビタントリオレエ−ト1.5部およびポリビニルアルコ−ル2部を含む水溶液28.5部を混合し、湿式粉砕法で微粉砕した後、この中にキサンタンガム0.05部およびアルミニウムマグネシウムシリケ−ト0.1部を含む水溶液45部を加え、さらにプロピレングリコ−ル10部を加えて攪拌混合し各製剤を得る。
本カルボキサミド化合物(1)~(5)のいずれかを1部、本化合物(A)を4部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイト30部およびカオリンクレ−62部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより各製剤を得る。
本カルボキサミド化合物(1)~(5)のいずれかを12.5部、本化合物(A)を37.5部、リグニンスルホン酸カルシウム3部、ラウリル硫酸ナトリウム2部および合成含水酸化珪素45部をよく粉砕混合することにより各製剤を得る。
本カルボキサミド化合物(1)~(5)のいずれかを3部、本化合物(A)を2部、カオリンクレ−85部およびタルク10部をよく粉砕混合することにより製剤を得る。
回転式種子処理機(シードドレッサー、Hans−Ulrich Hege GmbH製)でダイズ(品種;納豆小粒)種子10gに対して、所定の重量の供試化合物を含むシクロヘキサノン溶液100μlを塗沫処理した。
前記処理から1日後、リゾクトニア属菌(Rhizoctonia solani)で汚染された土壌をプラスチックポットに詰め、供試化合物を処理した種子を播種し、ガラス温室で20日間栽培した(これを処理区とする)。その後、各種子から出芽した苗におけるリゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)の発病の有無を観察し、下記式(1)により発病率を求めた。
一方、前記の塗沫処理をしていないダイズ種子を用いて、処理区と同様に栽培した(これを無処理区とする。)。そして処理区と同様に発病率を求めた。
なお、試験例1で使用した式(I)で示されるカルボキサミド化合物および、試験例1で使用した式(A)で示される化合物は、いずれもラセミ混合物を使用した。
処理区及び無処理区それぞれの発病率から、下記式(2)により処理区の効力を求めた。その結果を[表1]及び[表2]に示す。
プラスチックポットに土壌を詰め、ダイズ(品種;納豆小粒)を播種し、温室内で14日間生育させた。供試化合物をCECカクテル(シクロヘキサノン:ソルポール(登録商標)2680X(東邦化学工業製)=5:1(体積比))に溶解し、供試化合物を合計量で5%(w/v)含有する乳剤とした後、水で希釈し所定濃度にし、該希釈液を上記ダイズの葉面に充分に付着するように茎葉散布した。散布後植物を風乾し、1日後にダイズさび病(Phakopsora pachyrhizi)の夏胞子の水懸濁液(約10,000個/ml)を噴霧接種した。接種後はじめは20~23℃多湿下に1日間置き、さらに温室内に10日間栽培した(これを処理区とする。)。その後、ダイズさび病(Phakopsora pachyrhizi)の病斑面積を調査した。
一方、供試化合物の希釈液を茎葉散布しない以外は処理区と同様にダイズを栽培した(これを無処理区とする。)。処理区と同様にダイズさび病(Phakopsora pachyrhizi)の病斑面積を調査した。
なお、試験例2で使用した式(I)で示されるカルボキサミド化合物および、試験例2で使用した式(A)で示される化合物は、いずれもラセミ混合物を使用した。
処理区及び無処理区それぞれの病斑面積から、下記式(3)により処理区の効力を求めた。その結果を[表3]及び[表4]に示す。
回転式種子処理機(シードドレッサー、Hans−Ulrich Hege GmbH製)でダイズ(品種;納豆小粒)種子10gに対して、所定の重量の供試化合物を含むシクロヘキサノン溶液100μlを塗沫処理する。
前記処理から1日後、リゾクトニア属菌(Rhizoctonia solani)で汚染された土壌をプラスチックポットに詰め、供試化合物を処理した種子を播種し、ガラス温室で20日間栽培する(これを処理区とする)。その後、各種子から出芽した苗におけるリゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)の発病の有無を観察し、下記式(4)により発病率を求める。
一方、前記の塗沫処理をしていないダイズ種子を用いて、処理区と同様に栽培する(これを無処理区とする。)。そして処理区と同様に発病率を求める。
なお、試験例3で使用する式(I)で示されるカルボキサミド化合物はR体:S体が80:20~100:0、より好ましくはR体:S体が95:5~99:1の混合物を使用する。また、試験例3で使用する式(A)で示される化合物はラセミ混合物を使用する。処理区及び無処理区それぞれの発病率から、下記式(5)により処理区の効力を求める。その結果、本組成物を処理した処理区では高い効力を得ることができる。
Claims (5)
- カルボキサミド化合物と式(A)で示される化合物との重量比が、カルボキサミド化合物/式(A)で示される化合物=0.1/1~10/1である請求項1記載の植物病害防除組成物。
- カルボキサミド化合物と式(A)で示される化合物との重量比が、カルボキサミド化合物/式(A)で示される化合物=0.1/1~10/1である請求項3記載の植物病害防除方法。
- 植物又は植物を栽培する土壌が、ダイズ又はダイズを栽培する土壌である請求項3又は4記載の植物病害防除方法。
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WO2019096709A1 (en) | 2017-11-15 | 2019-05-23 | Syngenta Participations Ag | Microbiocidal picolinamide derivatives |
WO2019105933A1 (en) | 2017-11-29 | 2019-06-06 | Syngenta Participations Ag | Microbiocidal thiazole derivatives |
WO2019121149A1 (en) | 2017-12-19 | 2019-06-27 | Syngenta Participations Ag | Microbiocidal picolinamide derivatives |
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WO2020002331A1 (en) | 2018-06-29 | 2020-01-02 | Syngenta Crop Protection Ag | Microbiocidal oxadiazole derivatives |
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WO2020070132A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
WO2020070131A1 (en) | 2018-10-06 | 2020-04-09 | Syngenta Participations Ag | Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives |
WO2020084075A1 (en) | 2018-10-24 | 2020-04-30 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfoximine containing substituents |
WO2020141136A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2020141135A1 (en) | 2018-12-31 | 2020-07-09 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
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CA2892693C (en) * | 2012-11-30 | 2021-08-10 | Bayer Cropscience Ag | Binary fungicidal mixtures |
AR105658A1 (es) * | 2015-08-11 | 2017-10-25 | Sumitomo Chemical Co | Composición para el control de enfermedad de las plantas y método para el control de enfermedad de las plantas |
JP2017165716A (ja) * | 2016-03-11 | 2017-09-21 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
JP6875815B2 (ja) | 2016-09-29 | 2021-05-26 | 住友化学株式会社 | 嗅覚受容体共受容体 |
KR101855264B1 (ko) | 2018-01-11 | 2018-05-04 | 한국생명공학연구원 | 핌프리네틴을 유효성분으로 함유하는 소나무재선충병 방제용 조성물 |
CN109452287A (zh) * | 2018-11-14 | 2019-03-12 | 东莞东阳光科研发有限公司 | 一种杀菌组合物及其用途和制备方法 |
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PH12015500119B1 (en) | 2015-03-16 |
CO7200281A2 (es) | 2015-02-27 |
ZA201500808B (en) | 2016-10-26 |
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UA113316C2 (xx) | 2017-01-10 |
BR112015001121A2 (pt) | 2017-06-27 |
CA2879533A1 (en) | 2014-01-23 |
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AU2013291345B2 (en) | 2016-07-21 |
EP2883454A1 (en) | 2015-06-17 |
JP6106976B2 (ja) | 2017-04-05 |
CA2879533C (en) | 2019-09-17 |
JP2014019681A (ja) | 2014-02-03 |
NZ704955A (en) | 2016-08-26 |
EP2883454B1 (en) | 2018-08-01 |
KR20150038079A (ko) | 2015-04-08 |
MX2015000870A (es) | 2015-05-07 |
RU2621574C2 (ru) | 2017-06-06 |
CN104640448A (zh) | 2015-05-20 |
EP2883454A4 (en) | 2016-02-17 |
MY167598A (en) | 2018-09-20 |
US20150181876A1 (en) | 2015-07-02 |
AU2013291345A1 (en) | 2015-02-12 |
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