JPH07187917A - Fungicide composition - Google Patents

Abstract

PURPOSE:To obtain a fungicide composition for agricultural and horticultural use by combining a compound such as alpha-methoxyimino-2-[(2-methylphenoxy) methyl]phenylacetic acid methyl ester with an N-(3,5-dichlorophenyl)imide-type fungicidal compound. CONSTITUTION:This fungicide composition is produced by combining a compound of formula I [Ar is a (substituted)phenyl; Y is O, oxymethylene or methyleneoxy; X is NR<1>R<2> or OR<3> (R<1> to R<3> each is H or an alkyl)] with an N-(3,5-dichlorophenyl)imide-type compound having a partial structure of formula II. The compound of formula I is e.g. N-methyl-alpha-methoxyimino-2-[(4-chloro-2- methylphenoxy)methyl]phenylacetamide and the N-(3,5-dichlorophenyl)imide-type compound is e.g. procymidone, vinclozolin and iprodione. The composition is effective for controlling rice blast, helminthosporium leaf spot and sheath blight of rice, powdery mildew, scab, rust, snow blight, loose smut and target spot of wheat, blossom blight of fruit tree, etc.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a fungicide composition mainly 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 bactericide against, and also, from the response to the emergence of new diseases due to changes in agricultural form, etc., a bactericide composition having a high activity and a broad antibacterial spectrum is required. There is.

[0002]

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

[Chemical 2] [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 containing the compound shown by these and N- (3,5- dichlorophenyl) imide disinfectant 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, On the other hand, as the N- (3,5-dichlorophenyl) imide-based germicidal compound,

[Chemical 3] N- which is a bactericidal compound having a partial structure represented by
(3,5-Dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (procymidone), 3- (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine -2,4-dione (vinclozolin), 3- (3,5-dichlorophenyl) -N- (1-methylethyl) -2,4-dioxo-
Mention may be made of germicidal compounds such as 1-imidazolidinecarboxamide (iprodione). 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.

Some specific examples of the compound represented by the general formula 2 are shown below. (Ia) α-methoxyimino-2-[(2-methylphenoxy) methyl] phenylacetic acid methyl ester

[Chemical 4]

(IIa) N-methyl-α-methoxyimino-2-[(4-chloro-2-methylphenoxy) methyl] phenylacetamide

[Chemical 5]

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

[Chemical 6]

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

[Chemical 7]

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

[Chemical 8]

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

[Chemical 9]

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

[Chemical 10]

Plant diseases which can be controlled by the composition of the present invention include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoc).
tonia solani), powdery mildew of wheat (Erysiphe gramini)
s f. sp.hordei, f.sp.tritici), Fusarium head blight (Gibberel)
la zeae), rust (Puccinia striiformis, P.gramin
is, P.recondita, P.hordei), snow rot (Typhula sp.,
Micronectriella nivalis), naked smut (Ustilago tri
tici, 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), monili disease of apple (Sclerotinia mali), rot (Va)
lsa mali), powdery mildew (Podosphaera leucotricha)
), Leaf spot disease (Alternaria mali), scab (Ventur)
ia 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 oyster (Gloeosporium kaki), leaf scab (Cercospora kaki, Mycosphaerella nawae), downy mildew of cucumber (Pseudoperonospora cubensis), 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 (Coll
etotrichum lindemthianum), black pepper disease of peanut (My
cosphaerella personatum), brown spot (Cercospora ara)
chidicola), 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 red scab (Alternaria longipes), powdery mildew (Erysiphe c)
ichoracearum), 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), sclerotinia sclerotiorum and the like.

In the fungicide composition of the present invention, the compound represented by the general formula 2 which is an active ingredient compound and N- (3,
The mixing ratio with the 5-dichlorophenyl) imide-based bactericidal compound is not particularly limited, but normally, the N- (3,5-dichlorophenyl) imide-based bactericidal compound is 0.01 to 1 part by weight of the compound represented by the general formula 2. It is in the range of 100 parts by weight, preferably 0.1 to 50 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 (serisite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate, hydrated silica, etc.) and fine powders or granules such as salts for chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, ammonium salt, etc.), and examples of liquid carriers include water and 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.

As the surfactant, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenated products, 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.

[0018]

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 and% represent parts by weight and% by weight unless otherwise specified. Formulation Example 1 Compounds (Ia), (IIa), (IIb), (IIc), (II
d), (IIe) or (IIf) 1 part, procymidone, vinclozolin or iprodione 5 parts, synthetic hydrous silicon oxide 1 part, calcium lignin sulfonate 2 parts, bentonite 30 parts and kaolin clay 61 parts are well ground and mixed, and water is added. After adding and kneading well, it is granulated and dried to obtain granules. Formulation Example 2 Compounds (Ia), (IIa), (IIb), (IIc), (II
d), 5 parts of (IIe) or (IIf), 5 parts of procymidone, vinclozolin or iprodione, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 57 parts of kaolin clay are thoroughly pulverized and mixed, and water is added. After adding and kneading well, it is granulated and dried to obtain granules.

Formulation Example 3 Compounds (Ia), (IIa), (IIb), (IIc) and (II
d), (IIe) or (IIf) 0.5 part, procymidone,
2.5 parts of vinclozolin or iprodione, 86 parts of kaolin clay and 11 parts of talc are well pulverized and mixed to obtain a powder. Formulation Example 4 Compounds (Ia), (IIa), (IIb), (IIc), (II
d), (IIe) or (IIf) 5 parts, procymidone, vinclozolin or iprodione 25 parts, polyoxyethylene sorbitan monooleate 3 parts, carboxymethyl cellulose 3 parts and water 64 parts are mixed to give a particle size of 5 microns or less Wet pulverize to obtain a suspension. Formulation Example 5 Compounds (Ia), (IIa), (IIb), (IIc), (II
d), (IIe) or (IIf) 10 parts, procymidone,
A wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of vinclozolin or iprodione, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 35 parts of synthetic hydrous silicon oxide. Formulation Example 6 Compounds (Ia), (IIa), (IIb), (IIc), (II
An emulsion is obtained by mixing 5 parts of d), (IIe) or (IIf), 25 parts of procymidone, vinclozolin or iprodione, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 50 parts of xylene.

Test Example 1 A plastic pot was filled with sandy loam soil, seeded with cucumber (Sagamihanjiro), and grown in a greenhouse for 14 days. According to the formulation example 5, the reagent solution made into a wettable powder is diluted with water to a predetermined concentration,
The foliage was sprayed so as to adhere well to the leaf surface of the grown cucumber seedling. After air-drying, inoculate the leaf surface of the seedling with gray mold fungus,
The degree of disease (%) was investigated after growing for 4 days at 10 ° C. in the dark and high humidity. The results are shown in Table 1.

[Table 1]

Test Example 2 A plastic pot was filled with sandy loam soil, seeded with cucumber (Sagamihanjiro), and grown in a greenhouse for 14 days. The leaf surface of the cultivated cucumber seedling was inoculated with Botrytis cinerea, grown at 10 ° C. in the dark and humid for 2 days, and then grown in a greenhouse at 23 ° C. for 3 days to give a wettable powder according to Formulation Example 5. The test reagent was diluted with water to a predetermined concentration and sprayed on the foliage of the cucumber seedling so as to adhere sufficiently to the leaf surface. After spraying, the plants were grown at 10 ° C. in the dark and humid for 3 days, and then the disease degree (%) was investigated. The results are shown in Table 2.

[Table 2]

[0022]

The bactericidal composition of the present invention exhibits an excellent bactericidal effect due to a synergistic effect, and is therefore useful for controlling various diseases.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI technical display location A01N 43/76 47/38 B

Claims (2)

[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 germicide composition characterized by containing the compound shown by these and N- (3,5- dichlorophenyl) imide type germicidal compound as an active ingredient. 2. The bactericidal composition according to claim 1, wherein the N- (3,5-dichlorophenyl) imide bactericidal compound is one or more selected from the group consisting of procymidone, vinclozolin and iprodione.