JPH0826912A - Fungicidal composition - Google Patents

Abstract

PURPOSE:To exhibit excellent sterilizing effect by synergistic effect and effective ly control extremely broad kinds of various plant diseases by combinedly using a compound such as N-methyl-alpha-methoxyimino-2-phenoxyphenylacetamide and a copper compound. CONSTITUTION:This fungicidal composition is obtained by combinedly using a compound of formula I [Ar is a (substituted) phenyl; Y is O, oxymethylene or methyleleoxy; X is NR<1>R<2> or OR<3> (R<1> to R<3> are each H or an alkyl)] and a copper compound. The compound of formula I includes e.g. a compound of formula II, III, IV, V, VI, VII or VIII. Various inorganic salts (e.g. chloride or oxychloride) and organic salts (e.g. acetic acid salt or citric acid salt) used as a germicidal agents for agriculture and horticulture are preferably used as the copper compound. The fungicidal composition is effective in controlling e.g. blast, helminthosporium leaf spot an sheath blight of rice and powdery mildew, scab, rust and snow blight of wheats. The composition is preferably used in an amount of 1-80 pts.wt. of the copper compound based on 1 pt.wt. of the compound of formula I.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fungicide composition, particularly to a fungicide composition used for agriculture and horticulture.

2. Description of the Related Art Although many agricultural and horticultural fungicides are conventionally known, the types of diseases to be controlled are very large. It is difficult to select and control an appropriate fungicide against the above, and in view of the emergence of new diseases due to changes in agricultural form, a fungicide with a high activity and a broad antibacterial spectrum is required.

[0002]

SUMMARY OF THE INVENTION The present invention is to solve the above-mentioned problems and has the general formula

Embedded image [Wherein Ar represents an optionally substituted phenyl group, Y represents an oxygen atom, an oxymethylene group or a methyleneoxy group, X represents NR ¹ R ² or OR ³ , and R ¹ , R ² and R ^{3 s} are the same or different and each represents a hydrogen atom or a lower alkyl group (for example, an alkyl group having 1 to 4 carbon atoms such as a methyl group). ] The disinfectant composition which contains the compound shown by these and a copper compound as an active ingredient is provided.

The compound represented by the general formula 2 used in the present invention is a compound described in JP-A-63-23852, JP-A-3-246268, JP-A-4-288045 and the like. In the compound represented by the general formula 2, an optionally substituted phenyl group represented by Ar is, for example, a methyl group, an ethyl group or the like having 1 carbon atom.
~ 4 alkyl group, halogen atom such as chlorine atom, bromine atom, haloalkyl group having 1 to 4 carbon atoms such as trifluoromethyl group, alkoxy group having 1 to 4 carbon atoms such as methoxy group,
It represents a phenyl group which may be substituted with a substituent such as a haloalkoxy group having 1 to 4 carbon atoms such as a trifluoromethoxy group or a cyano group.

On the other hand, as the copper compound used in the present invention, various inorganic salts (for example, chlorides, oxychlorides, carbonates, oxides, etc.) used as agricultural and horticultural germicides.
Hydroxides, sulphates, phosphates, silicates, zinc chromates, hydrazinium sulphates) and organic salts (eg acetate, 8-hydroxyquinoline salts, oxalates, bis (3-phenylsalicylate) ), Naphthenate, linolenate, oleate and the like).

Some specific examples of the compound represented by the general formula 2 are shown below. (Ia) N-methyl-α-methoxyimino-2-
[(4-chloro-2-methylphenoxy) methyl] phenylacetamide

Embedded image

(Ib) N-methyl-α-methoxyimino-2-[(3-chlorophenoxy) methyl] phenylacetamide

[Chemical 4]

(Ic) N-methyl-α-methoxyimino-2-[(2,4-dichlorophenoxy) methyl] phenylacetamide

Embedded image

(Id) N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide

[Chemical 6]

(Ie) N-methyl-α-methoxyimino-2-[(3-trifluoromethylphenoxy) methyl] phenylacetamide

[Chemical 7]

(If) N-methyl-α-methoxyimino-2-phenoxyphenylacetamide

Embedded image

(IIa) α-methoxyimino-2-
[(2-Methylphenoxy) methyl] phenylacetic acid methyl ester

[Chemical 9]

The fungicidal composition of the present invention has an extremely wide variety of plant diseases that can be controlled by combining the compound represented by the above general formula 2 with a copper compound. Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhiz)
octonia solani), powdery mildew of wheat (Erysiphe grami)
nis f. sp.hordei, f.sp.tritici), Fusarium head blight (Gibber)
ella zeae), rust (Puccinia striiformis, P.gram
inis, P.recondita, P.hordei), snow rot (Typhula s)
p., Micronectriella nivalis), naked smut (Ustilago
tritici, U.nuda), lintel smut (Tilletia caries)
), Eyeblight (Pseudocercosporella herpotrichoides
), Strain rot (Rhizoctonia cerealis), scab (Rhync)
hosporium secalis), leaf blight (Septoria tritici),
Fusarium wilt (Leptosphaeria nodorum), Black spot of citrus fruit (Di
aporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P.italicum), apple monili disease (Sclerotinia mali), rot (Va)
lsa mali), powdery mildew (Podosphaera leucotricha)
), Leaf spot disease (Alternaria mali), scab (Ventu)
ria inaequalis), Pear scab (Venturia nashicol)
a), Black spot (Alternaria kikuchiana), Red scab (Gym
nosporangium haraeanum), peach scab (Sclerotin)
ia cinerea), scab (Cladosporium carpophilu)
m), Phomopsis rot (Phomopsis sp.), downy mildew of grapes (Plasmopara viticola), black rot (Elsino)
e ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopora ampe)
lopsidis), anthracnose of oysters (Gloeosporium kaki), leaf scab (Cercospora kaki, Mycosphaerella nawae), downy mildew of cucumber (Pseudoperonosporacubensis), anthracnose of cucumber (Colletotrichum lagenarium), powdery mildew (Sphaeroerotheca) , Vine blight (Mycosphaer
ella melonis), tomato ring spot (Alternaria solani)
), Leaf mold (Cladosporium fulvum), plague (Phyto)
phthora infestans), brown leaf spot of eggplant (Phomopsis vexan)
s), powdery mildew (Erysiphe cichoracearum), black spot of cruciferous vegetables (Alternaria japonica), white spot (Cercosporella brassicae), rust of green onion (Puccin)
ia allii), purpura of soybean (Cercospora kikuchii)
), Black spot (Elsinoe glycines), black spot (Diaport)
he phaseolorum var.sajae), anthracnose of kidney bean (Col
letotrichum lindemthianum), peanut black scab (M
ycosphaerella personatum), brown spot (Cercospora ar)
achidicola), powdery mildew of pea (Erysiphe pisi
), Downy mildew (Peronospora pisi), downy mildew (Peronospora viciae), plague (Phytophthora nicotia)
nae), summer blight of potato (Alternaria solani),
Plague (Phytophthora infestans), strawberry powdery mildew (Sphaerotheca humuli), plague (Phytophthora nicot)
ianae), tea leaf blast (Exobasidium recticulatu)
m), white scab (Erysiphe leucospila), tobacco scab (Alternaria longipes), powdery mildew (Erysiphe ci)
choracearum), anthracnose (Colletotrichum tabacum),
Plague (Phytophthora parasitica), brown spot of sugar beet (Cercospora beticola), scab of rose (Diplocarpo)
n rosae), powdery mildew (Sphaerotheca pannosa), plague (Phytophthora megasperma), brown spot of chrysanthemum (Sept)
oria chrysanthemiindici), white rust (Puccinia hor)
iana), gray mold of various crops (Botrytis cinere
a), it is effective in controlling a wide variety of plant diseases such as sclerotinia sclerotiorum.

In the disinfectant composition of the present invention, the mixing ratio of the compound represented by the general formula 2 as an active ingredient compound and the copper compound is not particularly limited, but usually 1 weight of the compound represented by the general formula 2 is used. 0.01 to 1 for copper compound
It is in the range of 000 parts by weight, preferably 0.1 to 100 parts by weight, more preferably 1 to 80 parts by weight.

The bactericidal composition of the present invention is usually mixed with a solid carrier, a liquid carrier or a gaseous carrier, and if necessary, auxiliary agents for formulation such as a surfactant, a sticking agent, a dispersant and a stabilizer are added. Then, it is used by formulating into emulsions, wettable powders, suspensions, granules, powders, dry flowables, aqueous liquids, oils, smokers, aerosols, microcapsules and the like. In these formulations, the total amount of active ingredient compounds is usually 0.1
˜99% by weight, preferably 0.2 to 90% by weight.

Examples of the solid carrier include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, attapulgite clay, bentonite, acid clay, etc.), talc and other inorganic minerals (sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate, hydrated silica, etc.), salts for chemical fertilizers (ammonium sulphate, ammonium phosphide, ammonium nitrate, urea, ammonium saccharin, etc.), and the like, and liquid carriers include, for example, water, alcohols ( Methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, kerosene, etc.), esters (Ethyl acetate, butyl acetate, etc.), Nitriles (acetonitrile, isobutyronitrile) ), Ethers (dioxane, diisopropyl ether), acid amides (dimethylformamide, dimethylacetamide), halogenated hydrocarbons (dichloroethane, trichlorethylene,
Carbon tetrachloride and the like), and the gaseous carrier includes butane gas, carbon dioxide gas, fluorocarbon gas and the like.

Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. And so on. As a fixing agent or a dispersant, casein,
Gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (polyvinyl alcohol,
Polyvinylpyrrolidone, polyacrylic acid, etc.) and the like, and as the stabilizer, PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl) A mixture of -4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or its ester, and the like.

The above-mentioned preparation is applied to a plant or soil as it is or after diluted with water or the like. For soil application,
It may be applied to the surface of the soil or mixed with the soil and applied. It can also be applied by various methods such as seed treatment and ULV. When used as a seed treatment agent, it is used by seed dressing treatment, seed dipping treatment, or the like. Further, it can be used in combination with other fungicides, insecticides, acaricides, nematicides, herbicides, seed disinfectants, fertilizers, soil conditioners and the like.

The application rate of the fungicide composition of the present invention varies depending on the type of active ingredient compound, mixing ratio, weather conditions, formulation form, application time, method, place, target disease, target crop, etc., but usually 1 0.001-1000g per are, preferably
0.1 to 100 g, and when the emulsion, wettable powder, suspension, liquid, etc. are diluted with water before application, the application concentration is 0.0001 to
It is 1% by weight, preferably 0.001 to 0.5% by weight, and granules, powders and the like are applied as they are without dilution. In the seed treatment, 0.001 to 50 g, preferably 0.01 to 10 g, of the total amount of the active ingredient compounds is generally used per 1 kg of seeds.

[0019]

EXAMPLES The present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified. Formulation Example 1 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 1 part, copper compound 5 parts, synthetic hydrous silicon oxide 1 part, lignin sulfonate calcium 2
Well, 30 parts of bentonite and 61 parts of kaolin clay are thoroughly pulverized and mixed, water is added and well kneaded, and then granulated and dried to obtain granules. Formulation Example 2 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 5 parts, copper compound 5 parts, synthetic hydrous silicon oxide 1 part, lignin sulfonate calcium 2
Parts, bentonite 30 parts and kaolin clay 57 parts are well pulverized and mixed, water is added and well kneaded, and then granulated and dried to obtain granules.

Formulation Example 3 Compounds (Ia), (Ib), (Ic), (Id) and (I
e), (If) or (IIa) 0.5 part, copper compound 2.5
Parts, 86 parts of kaolin clay and 11 parts of talc are well pulverized and mixed to obtain a powder. Formulation Example 4 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 5 parts, copper compound 25 parts,
3 parts of polyoxyethylene sorbitan monooleate, 3 parts of carboxymethyl cellulose and 64 parts of water are mixed and wet-milled until the particle size becomes 5 microns or less to obtain a suspension agent. Formulation Example 5 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 10 parts, copper compound 50
Parts, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 35 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain a wettable powder. Formulation Example 6 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 5 parts, copper compound 25 parts,
14 parts of polyoxyethylene styryl phenyl ether,
An emulsion is obtained by mixing 6 parts of calcium dodecylbenzene sulfonate and 50 parts of xylene.

Test Example 1 One plant of tomato (Pontelosa) was planted in a plastic pot filled with sandy loam soil, and when the third leaf developed, Formulation Example 5
According to the above, a diluting solution of the test agent at a predetermined concentration, which was made into a wettable powder, was sprayed so as to sufficiently adhere to the leaf surface. After air drying, spore fluid of Phytophthorainfestans (5 × 10 ⁴ cells / m 2)
l) was spray-inoculated on the leaf surface. After inoculation, the plants were cultivated at 24 ° C. for 1 week, and then the disease degree (%) was investigated. The results are shown in Table 1.

[Table 1]

Test Example 2 One strain of grape (berry A) was planted in a plastic pot filled with sandy loam soil, and at the time when the fourth leaf developed, a predetermined concentration of a reagent agent made into a wettable powder according to Formulation Example 5 The diluted solution was sprayed so as to adhere well to the leaf surface. After air-drying, spore fluid of Plasmopara viticola (2 × 10 ⁵ cells / ml)
Was spray-inoculated on the leaf surface. After inoculation, the plants were cultivated at 24 ° C. for 1 week, and then the disease degree (%) was investigated. Table 2 shows the results.

[Table 2] As shown in Table 1 and Table 2, the bactericidal composition of the present invention exhibits an excellent bactericidal effect due to the synergistic effect.

[0023]

INDUSTRIAL APPLICABILITY The fungicidal composition of the present invention is effective for controlling a wide variety of various plant diseases, and exhibits excellent bactericidal effect due to a synergistic effect, and therefore is useful as a fungicide. .

Claims (1)

[Claims] 1. A general formula: [Wherein Ar represents an optionally substituted phenyl group, Y represents an oxygen atom, an oxymethylene group or a methyleneoxy group, X represents NR ¹ R ² or OR ³ , and R ¹ , R ² and R ^{3 s} are the same or different and each represents a hydrogen atom or a lower alkyl group. ] The fungicide composition characterized by containing the compound shown by these and a copper compound as an active ingredient.