JPH07304607A - Germicidal composition - Google Patents

Abstract

PURPOSE:To obtain a germicidal composition, containing a specific germicidal compound and a compound selected from among an anilide-based germicidal compound, cymoxanil and fosetyl as active ingredients and capable of manifesting remarkable effects on plant disease injuries due to phycomycetes. CONSTITUTION:This germicidal composition contains a compound expressed by formula I [Ar is a (substitutedbhenyl; 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)] and one or more compounds selected from an anilide-based germicidal compound, cymoxanil and fosetyl in combination. N-Methyl-alpha-methoxyimino-2-[(3- trifluoromethylphenoxy)methyl] phenylacetamide expressed by formula II and compounds expressed by formulas III, IV, V, etc., are cited as the compound expressed by formula I. A compound selected from metalaxyl, benalaxyl, furalaxyl, ofurace, oxadixyl and cyprofuram is preferred as the anilide-based germicidal compound.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fungicide composition, and more particularly to a fungicide composition exhibiting excellent effects in controlling plant diseases caused by algae.

BACKGROUND OF THE INVENTION Many fungicides have been known so far, but it is difficult to sufficiently control plant diseases caused by algae fungi, and it is difficult to control plant diseases caused by algae fungi. There is a need for a fungicide with excellent efficacy.

[0002]

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

[Chemical 5] [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 compound and anilide series germicidal compound,
Cyano-N-[(ethylamino) carbonyl] -2-
The present invention provides a fungicide composition containing, as an active ingredient, one or more compounds selected from (methoxyimino) acetamide} and fosetyl {ethyl hydrogen phosphonate}.

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, the anilide-based bactericidal compounds include metalaxyl {methyl N- (2,6-dimethylphenyl) -N- (methoxyacetyl) alaninate}, benalaxyl {methyl N- (2,6-dimethylphenyl) -N- (phenylacetyl ) Alaninato}, fulleraxyl {methyl N- (2,6-dimethylphenyl) -N- (2-furanylcarbonyl) alaninate}, offlace {2-chloro-N- (2,6-dimethylphenyl) -N- (Tetrahydro-2-oxo-3
-Furanyl) acetamide}, oxadixyl {2-methoxy-N- (2-oxo-1,3-oxazolidine-
3-yl) aceto-2 ′, 6′-xylidide and other compounds having a 2,6-dimethylanilide structure, and ciproflam {N- (3-chlorophenyl) -N- (tetrahydro-
2-oxo-3-furanyl) cyclopropanecarboxamide} and the like, which mean a compound having a 3-chloroanilide structure. The fosetyl used in the present invention can also be used as a salt such as an aluminum salt.

In the compound represented by the general formula 5, 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 5 are shown below. (Ia) N-methyl-α-methoxyimino-2-
[(4-chloro-2-methylphenoxy) methyl] phenylacetamide

[Chemical 6]

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

[Chemical 7]

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

[Chemical 8]

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

[Chemical 9]

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

[Chemical 10]

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

[Chemical 11]

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

[Chemical 12]

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) and various diseases caused by Pythium sp. can be used to control various algal fungal diseases such as downy mildew, epidemics and diseases caused by Pythium. It exhibits excellent effects due to the bactericidal effect.

In the fungicide composition of the present invention, the mixing ratio of the compound represented by the general formula 5 as an active ingredient compound and one or more compounds selected from anilide fungicidal compounds, cimoxanil and fosetyl is not particularly limited. Usually, 0.01 to 100 parts by weight, preferably 0.1 to 50 parts by weight of one or more compounds selected from anilide fungicidal compounds, cimoxanil and fosetyl are used per 1 part by weight of the compound represented by the general formula 5. is there.

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, anilide fungicidal compound, simoxanil or focetylaluminum 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, anilide fungicidal compound, cimoxanil or focetyl aluminum 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, anilide fungicidal compound, cimoxanil or focetyl aluminum
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, anilide fungicidal compound, cimoxanil or focetyl aluminum 25
Part, 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, anilide fungicidal compound, simoxanil or focetylaluminum 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, anilide fungicidal compound, cimoxanil or focetyl aluminum 25
Part, polyoxyethylene styryl phenyl ether 14
Parts, 6 parts of calcium dodecylbenzenesulfonate and 50 parts of xylene are mixed to obtain an emulsion.

Test Example 1 A plastic pot was filled with sandy loam soil, sown with grape (berry A), and grown in a greenhouse for 40 days. A seedling of grape having three true leaves developed was spray-inoculated with a zoosporangium suspension of downy mildew bacterium. After inoculation, the mixture was left overnight under high humidity at 23 ° C., and then the reagent solution made into a wettable powder according to Formulation Example 5 was diluted with water to a predetermined concentration and sprayed on foliage so as to adhere sufficiently to the leaf surface. Then, it was grown in a greenhouse for 7 days, and the disease degree (%) was investigated. The results are shown in Table 1.

[Table 1]

Test Example 2 A plastic pot was filled with sandy loam soil, tomatoes (Ponterosa) were sown and grown in a greenhouse for 20 days. 2 true leaves
The tomato seedlings thus developed were diluted with water to give a predetermined concentration as a suspending agent according to Formulation Example 4, and sprayed on foliage so as to sufficiently adhere to the leaf surface. Then, a zoosporangia suspension of Phytophthora infestans was spray-inoculated. After the inoculation, the plate was left overnight at 23 ° C and high humidity, and then grown in a greenhouse for 4 days, and the disease degree (%) was investigated. The results are shown in Table 2.

[Table 2]

[0023]

The bactericidal composition of the present invention is particularly effective in controlling plant diseases caused by algae such as downy mildew and epidemics due to its excellent synergistic bactericidal effect.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display area A01N 57/12 Z

Claims (5)

[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 anilide type | system | group germicidal compound, cimoxanil, and fosetyl 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 an anilide type | system | group bactericidal compound as an active ingredient. 3. Anilide bactericidal compound is metalaxyl,
The fungicide composition according to claim 2, which is one or more selected from benalaxyl, furalaxyl, offlace, oxadixyl, and ciproflam. 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 a cimoxanil as an active ingredient. 5. 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 fosetyl as an active ingredient.