JPH07304606A - Germicidal composition - Google Patents

Abstract

PURPOSE:To obtain a germicidal composition, containing a specific germicidal compound and a compound selected from a cyanopyrrole-based germicidal compound and an anilino heterocyclic germicidal compound in combination and capable of manifesting remarkable effects on the control of plant disease injuries due to Botrytis cinerea. CONSTITUTION:This germicidal composition is obtained by combining a compound expressed by 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> are each H or a lower alkyl)] with one or more compounds selected from a cyanopyrrole-based germicidal compound and an anilino heterocyclic germicidal compound. For example, N-methyl-alpha-methoxyimino-2-[(4-chloro-2-methylphenoxy) methyl]phenylacetamide and compounds expressed by formulas III, IV, V, etc., are cited as the compound expressed by formula I. Fludioxonil is preferred as the cyanopyrrole-based germicidal compound and fluazinam is preferred as the anilino heterocyclic germicidal compound. The composition is effective in controlling gray mold.

Description

Detailed Description of the Invention

[0001]

This invention relates to fungicidal compositions, especially B
The present invention relates to a fungicide composition which is excellent in controlling plant diseases caused by otrytis cinerea.

[Prior Art and Problems to be Solved by the Invention] Botr
Since ytis cinerea causes gray mold disease in various crops such as grapes, fruit trees such as citrus fruits, cucumbers, tomatoes, and vegetables such as legumes, its control is important.
There has been a demand for excellent fungicides for controlling diseases caused by otrytis cinerea.

[0002]

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

[Chemical 4] [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 bactericidal composition which contains the compound shown by these and the 1 or more types of compounds chosen from a cyanopyrrole bactericidal compound and an anilino heterocyclic bactericidal compound as an active ingredient.

The compounds represented by the general formula 5 used in the present invention are the compounds described in JP-A-63-23852, JP-A-3-246268, JP-A-4-288045 and the like, On the other hand, as a cyanopyrrole sterilizing compound, 4- (2,2-difluoro-1,3)
-Benzodioxol-4-yl) -1H-pyrrole-3
-Carbonitrile {fludioxonil} and other compounds having a 4-aryl-1H-pyrrole-3-carbonitrile structure, and examples of the anilino heterocyclic bactericidal compound include 2-anilino-4,6-dimethylpyrimidine {pyrimethanil}. , 2-anilino-4methyl-6- (1-propynyl) pyrimidine {mepanipyrim} and other compounds having a 2-anilinopyrimidine structure, and 3-chloro-N-
(3-chloro-5-trifluoromethyl-2-pyridyl) -α, α, α-trifluoro-2,6-dinitro-
N-aryl- such as p-toluidine {fluazinam}
Examples thereof include compounds having a 2,6-dinitroaniline structure.

In the compound represented by the general formula 4, Ar
The optionally substituted phenyl group represented by is, for example, an alkyl group having 1 to 4 carbon atoms such as a methyl group and an ethyl group, a halogen atom such as a chlorine atom and a bromine atom, and a carbon number such as a trifluoromethyl group. 1 to 4 haloalkyl group, methoxy group or other alkoxy group having 1 to 4 carbon atoms, trifluoromethoxy group or other haloalkoxy group having 1 to 4 carbon atoms, phenyl optionally substituted with a substituent such as cyano group Represents a group.

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

[Chemical 5]

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

[Chemical 6]

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

[Chemical 7]

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

[Chemical 8]

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

[Chemical 9]

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

[Chemical 10]

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

[Chemical 11]

The fungicidal composition of the present invention is, for example, rice blast (Pyricularia oryzae), sesame leaf blight (Cochliob).
olus miyabeanus), blight (Rhizoctonia solani),
Powdery mildew of wheat (Erysiphe graminis f. Sp. Hordei,
f.sp.tritici), Fusarium head blight (Gibberella zeae), Rust (Puccinia striiformis, P.graminis, P.recondita,
P.hordei), snow rot (Typhula sp., Micronectriella)
nivalis), naked smut (Ustilago tritici, U.nuda),
White squirrel smut (Tilletia caries), eye blight (Pseudo
cercosporella herpotrichoides), strain rot (Rhizocto
nia cerealis), cloud disease (Rhynchosporium secalis),
Leaf blight (Septoria tritici), wilt disease (Leptosphaeria)
nodorum), citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium)
digitatum, P.italicum), apple monili disease (Scle
rotinia mali), rot (Valsa mali), powdery mildew (Podosphaera leucotricha), leaf spot disease (Alternar)
ia mali), scab (Venturia inaequalis), pear scab (Venturia nashicola), black spot (Alternaria k)
ikuchiana), scab (Gymnosporangium haraeanum)
), Peach scab (Sclerotinia cinerea), scab (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), Downy mildew (Plasmopara vit)
icola), black rot (Elsinoe ampelina), late rot (Gl)
omerella cingulata), powdery mildew (Uncinula necato)
r), rust (Phakopora ampelopsidis), anthracnose of oysters (Gloeosporium kaki), leaf blight (Cercospora kaki,
Mycosphaerella nawae), downy mildew of cucumber (Pseudo
peronospora cubensis), anthracnose of cucumber (Colletotri)
chum lagenarium), powdery mildew (Sphaerotheca fulig)
inea), vine blight (Mycosphaerella melonis), tomato rot (Alternaria solani), leaf mold (Cladospo)
rium fulvum), plague (Phytophthora infestans), brown leaf spot of eggplant (Phomopsis vexans), powdery mildew (Erysip)
he cichoracearum), Black spot of cruciferous vegetables (Altern
aria japonica), White spot (Cercosporella brassicae)
), Green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black spot (Elsinoe glyce)
ines), Black spot (Diaporthe phaseolorum var.sajae
), Kidney anthracnose (Colletotrichum lindemthianu)
m), peanut black sickness (Mycosphaerellapersonatum)
), Brown spot (Cercospora arachidicola), powdery mildew of pea (Erysiphe pisi), downy mildew (Peronospor)
a pisi), downy mildew of broad bean (Peronospora viciae),
Plague (Phytophthora nicotianae), Potato summer plague (Alternaria solani), Plague (Phytophthora infes)
tans), powdery mildew of strawberry (Sphaerotheca humuli
), Plague (Phytophthora nicotianae), tea net blast (Exobasidium recticulatum), white scab (Erysiphe)
leucospila), tobacco scab (Alternaria longipe)
s), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), plague (Phytophthora par)
asitica), brown leaf spot of sugar beet (Cercospora beticola)
), Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), plague (Phytophthora meg)
asperma), brown spot of chrysanthemum (Septoria chrysanthemiind)
ici), white rust (Puccinia horiana), gray mold of various crops (Botrytis cinerea), sclerotini (Sclerotini)
a sclerotiorum), etc., but in particular, gray mold (Botr disease) of various crops such as fruit trees and vegetables.
ytis cinerea) shows excellent effects due to its excellent synergistic bactericidal effect.

In the fungicidal composition of the present invention, the mixing ratio of the compound represented by the general formula 4 which is an active ingredient compound and one or more compounds selected from cyanopyrrole fungicides and anilino heterocyclic fungicides is Although not particularly limited, usually, 0.001 to 100 parts by weight of the cyanopyrrole-based bactericidal compound or the anilinoheterocyclic bactericidal compound, preferably 1 part by weight of the compound represented by the general formula 4
It is in the range of 0.002 to 20 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 solid carriers 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.), salts for chemical fertilizers (ammonium sulphate, ammonium phosphide, ammonium nitrate, urea, ammonium saccharin, etc.), and the like, and liquid carriers include 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, fludioxonil, pyrimethanil, mepanipyrim or fluazinam 5
Parts, synthetic hydrous silicon oxide 1 part, calcium lignin sulfonate 2 parts, bentonite 30 parts and kaolin clay 6
One part is well pulverized and mixed, water is added and kneaded well, and then granulated and dried to obtain granules. Formulation Example 2 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 5 parts, fludioxonil, pyrimethanil, mepanipyrim or fluazinam 5
Parts, 1 part synthetic hydrous silicon oxide, 2 parts calcium lignin sulfonate, 30 parts bentonite and 5 kaolin clay
7 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, fludioxonil, pyrimethanil, mepanipyrim or fluazinam
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, fludioxonil, pyrimethanil, mepanipyrim or fluazinam 2
5 parts, polyoxyethylene sorbitan monooleate 3
Parts, 3 parts of carboxymethyl cellulose and 64 parts of water are mixed and wet-ground 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, fludioxonil, pyrimethanil, mepanipyrim or fluazinam 5
A wettable powder is obtained by thoroughly pulverizing and mixing 0 part, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 35 parts of synthetic hydrous silicon oxide. Formulation Example 6 Compounds (Ia), (Ib), (Ic), (Id), (I
e), (If) or (IIa) 5 parts, fludioxonil, pyrimethanil, mepanipyrim or fluazinam 2
5 parts, polyoxyethylene styryl phenyl ether 1
An emulsion is obtained by mixing 4 parts, 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, the leaf surface of the seedling was inoculated with gray mold and grown at 10 ° C. in the dark and humid for 4 days.
investigated. The results are shown in Table 1.

[Table 1]

[0022]

The fungicidal composition of the present invention exhibits excellent efficacy against Botrytis cinerea, particularly in various crops such as fruit trees and vegetables, due to its excellent synergistic fungicidal effect.

Claims (7)

[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 one or more compounds selected from a cyanopyrrole fungicidal compound and an anilino heterocyclic fungicidal compound as an active ingredient. 2. 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 bactericidal composition of Claim 1 containing the compound shown by these and a cyanopyrrole bactericidal compound as an active ingredient. 3. The fungicidal composition according to claim 2, wherein the cyanopyrrole fungicidal compound is fludioxonil. 4. 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 an anilino heterocyclic type | system | group fungicide compound as an active ingredient. 5. The fungicide composition according to claim 4, wherein the anilino heterocyclic bactericidal compound is a compound having a 2-anilinopyrimidine structure. 6. The compound having a 2-anilinopyrimidine structure is pyrimethanil or mepanipyrim.
The disinfectant composition described. 7. The fungicide composition according to claim 4, wherein the anilino heterocyclic fungicidal compound is fluazinam.