JPH11322509A - Microbicide containing optically active methoximinoacetic acid amide derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a microbicide having a wide and excellent controlling spectrum, and manifesting activities against microorganisms resistant to conventional chemicals. SOLUTION: This microbicide contains an optically active methoximinoacetic acid amide derivative of the formula [Ar is an aryl or a heteroaryl; Y is H, a halogen atom, a 1-4C alkyl, a 1-4C haloalkyl, a 1-4C alkoxy, a 1-4C haloalkoxy, a 1-4C alkylthio, a 2-6C alkynyloxy, cyano, nitro or an aryl; (n) is an integer of 1-3], and having a minus value of the optical rotation in chloroform, and one or more compounds selected from the group of a triazole-based microbicide, a morpholine-based microbicide, a benzimidazole-based microbicide, a dicarboximide-based microbicide, a phenylamide-based microbicide and maleimide-based microbicide.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a fungicide containing a specific optically active methoxyiminoacetic acid amide derivative and other fungicidal components as active ingredients and which can be effectively used in the agricultural and horticultural fields.

[0002]

2. Description of the Related Art Hitherto, fungicides for controlling various diseases in the field of agriculture and horticulture have been developed, and have been put to practical use alone or as a mixture. Methoxyiminoacetic acid amide derivatives, which are actively developed in recent years, are fungicides against agricultural and horticultural diseases, diseases caused by ascomycetes such as powdery mildew fungi, diseases caused by basidiomycetes such as rust fungus, eggs such as downy mildew fungus It is an effective compound against fungal diseases and gray mold and blast diseases.

On the other hand, the fungicide (2RS, 3SR) -1- [3-
(2-Chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1H-1,2,4-triazole (epoxyconazole), (RS) -1-p-chlorophenyl-4 , 4-Dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (tebuconazole), (±) -cis-4- [3- (4
-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (fenpropimorph) is a variety of wheat such as powdery mildew, rust, leaf blight, net spot, and scald. It is known as a compound effective against diseases. Also, methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (benrate), dimethyl 4,4-
(o-phenylene) bis (3-thioallophanate) (Topazin M), N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (procimidon), 3- (3,5-dichlorophenyl) -N-isopropyl-2,4
-Dioxoimidazolidine-1-carboxamide (Robral), 2,3-dichloro-N-4-fluorophenylmaleimide (fluoroimide), etc. are used for gray mold, sclerotium, scab, scab, charcoal It is a compound that is effective against various diseases mainly in the fields of upland crops and horticulture, such as disease, deciduous disease and Monilia disease.

[0004]

However, although pesticides, including fungicides, each have a certain bactericidal effect, a bactericidal spectrum, a bactericidal effect, a residual effect, and a systemic transfer property have been known. However, various properties such as low invasiveness, therapeutic property, low toxicity to various animals, reduction of environmental pollution, frequency of application, and reduction in the amount of applied drug are not fully satisfied.
For example, a single use of a drug having an insufficient sterilization spectrum can control only a specific disease, so that a plurality of drugs must be used, resulting in a problem that the total number of times the drug is used is increased as a whole.

[0005] As a result of repeated use of these drugs, pathogenic bacterial species that have acquired resistance to various drugs have appeared. In particular, many occurrences of strains showing resistance to various drug strains such as gray mold, downy mildew or powdery mildew occurring in various crops have been reported. In addition, in order to use an effective drug for a long period of time, a method of rotating a drug having a different action mechanism has been adopted in an actual control scene, but it has not always achieved sufficient results.

[0006] On the other hand, as described above, methoxyiminoacetic amide derivatives alone have a wide spectrum of disease control, but do not necessarily show a sufficient effect on all diseases. Therefore, when the present derivative is used alone for controlling diseases with insufficient effects, it is necessary to increase the amount of applied drug, and there is a concern about the effect on the environment. Although methoxyiminoacetic acid amide derivatives alone show a high bactericidal effect, it cannot be denied that the same occurs due to the past history of the problem of resistance to other drugs.

[0007] In view of the above, there is a constant need for the development of a drug having a broad and excellent control spectrum and exhibiting an effect on resistant bacteria of an existing drug or a drug capable of suppressing the development of resistance. An object of the present invention is to provide a bactericide meeting such a demand.

[0008]

Means for Solving the Problems The present inventors have designed a specific optically active methoxyiminoacetic acid amide derivative (hereinafter referred to as a methoxyiminoacetic amide derivative).
It may be referred to as “the present derivative”. A) while maintaining the advantages and compensating for the disadvantages, the synergistic effect which cannot be predicted by combining this derivative with one or more compounds selected from the following group A is The present invention was found to be performed, and the present invention was completed. Group A: triazole fungicide, morpholine fungicide, benzimidazole fungicide, dicarboximide fungicide, phenylamide fungicide, maleimide fungicide.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The derivative used in the present invention has the following general formula (I)

[0010]

Embedded image

(In the above general formula, Ar represents an aryl group or
Represents a teloaryl group, Y is a hydrogen atom, a halogen atom,
C₁-C_FourAn alkyl group of C₁-C_FourHaloalkyl
Group, C ₁-C_FourAn alkoxy group of C₁-C_FourNo haloal
Coxy group, C₁-C_FourAn alkylthio group of C_Two-C₆of
Alkynyloxy, cyano, nitro or aryl
And n represents an integer of 1 to 3. ),
Optically active methae with a negative optical rotation in chloroform.
It is a xyiminoacetic acid amide derivative.

The optically active methoxyiminoacetic acid amide derivative used in the present invention is represented by the above general formula (I), and its optical rotation shows a negative value in a chloroform solvent. The optical purity is preferably 50% ee or more, and more preferably 70% ee.
The above is particularly preferable at 85% or more. In the optically active methoxyiminoacetic acid amide derivative of the present invention, there are stereoisomers of the partial E / Z of methoxyimine and 1- (hetero) arylethoxyimine. From the viewpoint of biological activity, any part is preferably E-form, but the present invention includes any stereoisomer of any part.

In the above general formula (I), Ar represents an aryl group such as a phenyl group or a naphthyl group; a heteroaryl group such as a pyridyl group or a thiazolyl group. Of these, an aryl group is preferable, and a phenyl group is more preferable. Y is a substituent bonded to the ring of the aryl or heteroaryl group, and is a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom; a methyl group, an ethyl group, an n-propyl group, an iso- Propyl group,
n- butyl group, an alkyl group of C ₁ -C _4, such as sec- butyl group; methoxy group; trifluoromethyl group, difluoromethyl group, a haloalkyl group of C ₁ -C _4, such as trichloromethyl group or dichlorodifluoromethane ethyl ,
Ethoxy, iso- propoxy, n- alkoxy C ₁ -C _4, such as butoxy group; or a trifluoromethoxy group, difluoromethoxy group or a haloalkoxy group having C ₁ -C _4, such as dichlorodifluoromethane ethoxy; A C ₁ -C ₄ alkylthio group such as a methylthio group or an ethylthio group; a C ₂ -C ₆ alkynyloxy group such as a propargyloxy group; a cyano group; a nitro group; or an aryl group such as a phenyl group. In addition, two adjacent substituents among these substituents may be combined to form a methylenedioxy group, an ethylenedioxy group, or the like to form a condensed ring with an aryl ring or a heteroaryl ring. Of these, a hydrogen atom, a halogen atom, C
Alkyl group of ₁ -C _4, haloalkyl group of C ₁ -C _4,
A C ₁ -C ₄ alkoxy group and a C ₁ -C ₄ haloalkoxy group, more preferably a hydrogen atom, a chlorine atom,
An ₁ -C ₂ haloalkoxy group a haloalkyl group or a C ₁ -C _2, and most preferably a trifluoromethyl group. n represents an integer of 1 to 3. It preferably represents 1 or 2.

As the optically active methoxyiminoacetic acid amide derivative used in the present invention, those represented by the general formula (II) are preferred.

[0015]

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Other fungicides used with the compounds of the present invention are specifically (2RS, 3SR) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl ] -1H-1,2,4-triazole (generic name: epoxyconazole), 1- (biphenyl-4-yloxy) -3,3-dimethyl-1- (1H
-1,2,4-triazol-1-yl) butane-2-
Oar (general name: bittanal), 1-[(2
RS, 4RS: 2RS, 4SR) -4-bromo-2-
(2,4-dichlorophenyl) tetrahydrofurfyl] -1H-1,2,4-triazole (generic name: bromconazole), bis (4-fluorophenyl) (methyl) (1H-1,2,4-triazole -1-ylmethyl) silane (generic name: fursilazole), (2RS, 3
RS; 2RS, 3SR) -2- (4-chlorophenyl)
-3-cyclopropyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol (generic name: cyproconazole), cis, trans-3-chloro-4- [4- Methyl-2- (1H-1,2,4-triazol-1-ylmethyl) -1,3-dioxirane-2
-Yl] phenyl 4-chlorophenyl ether (generic name: diphenoconazole), 4- (4-chlorophenyl) -2-phenyl-2- (1H-1,2,4-triazol-1-ylmethyl) butyronitrile (generic name: phen) Buconazole), 3- (2,4-dichlorophenyl) -6-fluoro-2- (1H-1,2,4-triazol-1-yl) quinazolin-4 (3H) -one (generic name: fluquinonazole ), (RS) -2- (2,4
-Dichlorophenyl) -1- (1H-1,2,4-triazol-1-yl) hexane-2-ol (generic name:
Hexaconazole), (1RS, 5RS: 1RS, 5S
R) -5- (4-Chlorobenzyl) -2,2-dimethyl-1- (1H-1,2,4-triazol-1-ylmethyl) cyclopentanol (generic name: metconazole), 2-p-chlorophenyl -2- (1H-1,2,2,
4-triazol-1-ylmethyl) hexanenitrile (generic name: microbutanyl), (±) -1- [2-
(2,4-dichlorophenyl) -4-propyl-1,3
-Dioxiran-2-ylmethyl] -1H-1,2,4
-Triazole (generic name: propiconazole), (R
S) -1-P-chlorophenyl-4,4-dimethyl-3
-(1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (generic name: teguconazole), (RS) -2- (2,4-dichlorophenyl)-
3- (1H-1,2,4-triazol-1-yl) propyl 1,1,2,2-tetrafluoroethyl ether (generic name: tetraconazole), 1- (4-chlorophenoxy) -3, 3-dimethyl-1- (1H-1,2,4
-Triazol-1-yl) butan-2-one (generic name: triadimefon), (1RS, 2RS; 1RS,
2SR) -1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazole-1-
Il) Triazole fungicides such as butan-2-ol (generic name: triadimenol); (±) -cis-4
-[3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (generic name:
Fenpropimorph), 2,6-dimethyl-4-tridecylmorpholine (generic name: tridemorph),
Morpholine fungicides such as (RS) -1- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (generic name: fenpropidine); methyl-1
-(Butylcarbamoyl) benzimidazol-2-ylcarbamate (generic name: benomyl), dimethyl 4,
4 '-(o-phenylene) bis (3-thioallophanate) (generic name: thiophanate methyl), methylbenzimidazol-2-ylcarbamate (generic name: Car
bendazim), 2- (thiazol-4-yl) benzimidazole (generic name: thiabendazo)
l) and other benzimidazole fungicides; N- (3,5)
-Dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (generic name: brosimidon), 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidin-1 -Carboxamide (generic name: iprodione), (RS) -3-
Dicarboximide fungicides such as (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (generic name: vinclozolin); methyl N- (2-methoxyacetyl) ) -N- (2,
6-xylyl) -DL-alaninate (general name: metalaxyl), 3'-isopropoxy-o-toluanilide (general name: mepronil), α, α, α-trifluoro-
3'-isopropoxy-o-toluanilide (general name: flutranyl), 5,6-dihydro-2-methyl-1,4
-Phenamide bactericides such as -oxathi-in-3-carboxanilide 4,4-dioxide (generic name: oxycarboxine); 2,3-dichloro-N-4-fluorophenylmaleimide (generic name: fluoroimide) And maleimide-based germicides.

Furthermore, in the present invention, when used as a fungicide for wheat, a combination of the present derivative and one selected from epoxyconazole, tebuconazole and fenpropimorph is particularly effective. When used as a fungicide for vegetables, fruit trees, tea plants and turfgrass, a combination of the present derivative and one selected from benomyl, thiophanate methyl, procymidone, iprodione, metalaxyl or fluoroimide is particularly effective.

The main diseases targeted in the present invention are wheat powdery mildew (Erysiphegraminis f.sp.trit).
ici), leaf rust (Pucciniarecondita), leaf blight (Septo)
riatritici), Fusarium wilt (Septoria nodorum), eye spot (Psuedocercosporella herpotrichoides), Fusarium head blight (Gibberella zeae), snow rot (Fusaruim nivale), etc .;
Barley powdery mildew (Erysiphe graminis f.sp.horde)
i), leaf rust (Puccinia hordei), scald disease (Rhynchospo)
rium secalis), net spot (Pyrenophora teres), etc .; rice blast (Pyricularia oryzae), sheath blight (Rhizocto)
nia solani), sesame leaf blight (Cochliobolus miyabeanu)
s), idiot disease (Gibberella fujikuroi), etc .; bean gray mold (Botrytis cinerea), sclerotium disease (Sclerotini)
a sclerotiorum); Potato blight (Phytophtora)
infestans), summer blight (Alternaria solani); sugar beet brown spot (Cercospora viticola); cucumber powdery mildew (Sphaerotheca fuliginea), anthracnose (Colletotri)
chum lagenarium), scab (Cladosporium cucumerinu)
m), gray mold (Botrytis cinerea), downy mildew (Pseud
operonosopora cubensis); Apple scab (Venturi)
a inaequalis), spot leaf blight (Alternaria mali), monilia disease (Monilinia mali), etc .; pear scab (Venturia)
nashicola), black spot (Alternaria kikuchiana), etc .;
Peach ash (Monilinia fructicola), scab (Clados)
porium carpophilum); Grape downy mildew (Plasmopara)
viticola), brown spot (Pseudocercospora vitis), gray mold (Botrytis cinerea), etc .; oyster leaf fall (Cercos
pora kaki, Mycosphaerella nawae); tea anthracnose (Colletotrichum theae-sinensis), ring spot (Pestalot)
ia theae, Pestalotia longiseta), rice blast (Exobasid)
ium vexans) and a wide range of diseases caused by various plant pathogens belonging to ascomycetes, basidiomycetes, oomycetes and incomplete fungi which occur in various cultivated crops, vegetables, fruit trees and flowers. Furthermore, the fungicide of the present invention not only exhibits a synergistic fungicidal effect on the above-mentioned diseases, but also can simultaneously control various diseases in the agricultural and horticultural fields.

In using the fungicide of the present invention,
The derivative and other fungicides may be used as they are, for example, only by mixing them, but it is preferably used as a composition to which a pesticide auxiliary commonly used in the pesticide formulation industry is added. The dosage form is not limited, but it is preferably used in the form of, for example, emulsions, wettable powders, powders, flowables, granules, tablets, oils, sprays, aerosols and the like. It is preferable to use an emulsion or a flowable for wheat and a flowable or wettable powder for vegetables, fruit trees, tea plants and turfgrass.

Upon formulation, various pesticidal auxiliaries are used for the purpose of, for example, improving the effect, stabilizing, and improving the dispersibility. The pesticide adjuvant varies depending on the formulation type, but generally comprises a carrier (diluent) such as a liquid carrier or a solid carrier; and a surfactant. Examples of the liquid carrier include water; alkylbenzenes such as toluene and xylene; alkylnaphthalenes such as methylnaphthalene and dimethylnaphthalene; aromatic hydrocarbons such as chlorobenzene; methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol and benzyl alcohol. Alcohols such as; halogenated hydrocarbons such as ethylene chloride, methylene chloride, chloroform, and carbon tetrachloride; acetone,
Ketones such as methyl ethyl ketone, cyclohexanone and methyl isobutyl ketone; ethers such as ethyl ether, ethylene oxide and dioxane; esters such as ethyl acetate, amyl acetate, γ-butyrolactone, ethylene glycol acetate; nitriles such as acetonitrile and acrylonitrile; , N-dimethylformamide,
Amides such as N, N-dimethylacetamide and N-methylpyrrolidone; sulfoxides such as dimethyl sulfoxide; alcohol ethers such as ethylene glycol monomethyl ether; aliphatic or alicyclic hydrocarbons such as n-hexane and cyclohexane; Industrial gasoline such as petroleum ether and solvent naphtha; petroleum fractions such as paraffins, kerosene and light oil; animal and vegetable oils; and fatty acids.

As the solid carrier, mineral powders such as clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar and quartz;
Plant powders such as starch, crystalline cellulose, and flour; silicates, sugar polymers, alumina, highly dispersed silicic acid, waxes, gum arabic, and the like can be used. When formulating emulsions, wettable powders, flowables and the like, surfactants (or emulsifiers) are used for the purpose of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading and the like. Such surfactants include polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl ether,
Nonionic surfactants such as organic silicons such as polyoxyethylene alkyl ester, polyoxyethylene castor oil ether, polyoxyethylene sorbitan alkyl ester, sorbitan alkyl ester, carboxymethyl cellulose, polyvinyl alcohol, and trisiloxane alkoxylate; alkylbenzene Anionic surfactants such as sulfonates, alkyl sulfosuccinates, alkyl sulfates, polyoxyethylene alkyl sulfates, aryl sulfonates, sodium lignin sulfonate, sodium lauryl sulfate; cationic surfactants alkyl such as alkyldimethylbenzylammonium chloride Examples include cationic surfactants such as ammonium salts, and may be used alone or in combination of two or more depending on the purpose. It is use.

The effects of the addition of these surfactants are various, for example, carboxymethylcellulose, polyvinyl alcohol and the like have a fixing effect; sodium ligninsulfonate and sodium lauryl sulfate have a disintegrating effect; higher alcohol sodium sulfate, stearyltrimethylammonium chloride, Polyoxyethylene lauryl phenyl ether and the like can be expected to have a spreading effect; dialkyl sulfosuccinate and the like can have a wet spreading effect; carboxymethyl cellulose, polyvinyl alcohol and the like can have a fixing effect.

When used as an agricultural chemical, it is incorporated into an organosilicone surfactant such as trisiloxane alkoxylate (Silhouette L-77 or the like) or a formulation, or the surfactant is used in a tank mix. As a result, the spreading effect and spreading effect of the present derivative, which is an active ingredient in the fungicide, and other fungicides are improved, and as a result, the biological effect is significantly increased, which is economically advantageous. When incorporated into the formulation, the amount of the organosilicone surfactant used is 0.1% by weight or more of the active ingredient, and the improvement of the disease control effect is observed.
10 weight times the range, more preferably 0.5 to 2.5
It is preferable to use in the range of the weight amount.

In formulating, the content of the active ingredient is
It is selected from the range of 0.1 to 99.5%, and may be appropriately determined depending on various conditions such as the formulation form and application method. For example, in the case of a powder, about 0.5 to 20% by weight, preferably 1 to 10% by weight, about 1-90% by weight, preferably 10-80% by weight for wettable powders, about 1-90% by weight for emulsions
The active ingredient can be contained in a degree, preferably 10 to 40% by weight. In the fungicide of the present invention, the mixing ratio of the present compound and the other fungicidal components is preferably 1 part by weight of the former and generally 0.01 to 100 parts by weight, more preferably 0.1 to 20 parts by weight of the latter. Parts by weight are good.

In using the formulated pesticide of the present invention, for example, in the case of an emulsion, an active ingredient, a solvent, a surfactant and the like are mixed to prepare an emulsion of a stock solution. Diluted with water and applied.
In the case of a wettable powder, a wettable powder is prepared by mixing an active ingredient, a solid carrier, a surfactant and the like, and the stock solution is usually diluted with water to a predetermined concentration before use. In the case of a powder, the active ingredient, a solid carrier and the like are mixed, and the mixture is usually applied as it is when used. In the case of granules, a mixture of an active ingredient, a solid carrier, a surfactant and the like is prepared by granulation, and is usually applied as it is when used. However, the preparation method in each of the above-mentioned preparation forms is not limited to the above-mentioned method, and can be appropriately selected by those skilled in the art according to the kind of the active ingredient, the purpose of application, and the like.

The method of applying the pesticide of the present invention is not particularly limited, and it can be applied by any method such as foliage application, water application, soil treatment, seed treatment and the like. For example, in the case of foliage application, 50 to 500 liters of an aqueous solution having a concentration range of 5 to 1000 ppm, preferably 10 to 500 ppm may be applied per 10 ares. In the case of water application, the application rate is usually 1 to 10 kg per 10 ares for granules containing 5 to 15% of the active ingredient. In the case of soil treatment, 5 to 1000 ppm, preferably 10 to 500 pp
An aqueous solution having a concentration range of m may be applied in an amount of 1 to 10 liters per m ² . In the case of seed treatment, an aqueous solution having a concentration range of 10 to 1000 ppm per kg of seed
What is necessary is just to apply about 100 liters.

The pesticide of the present invention can also be used in admixture with other active ingredients which do not inhibit the bactericidal and insecticidal effects of the present active ingredient, such as fungicides, insecticides and acaricides. Combining this derivative with a suitable known disinfectant, insecticide or acaricide can complement the control spectrum and thus has a significant effect on reducing the number of applications and consequently the total use. Can demonstrate. Further, the combination of the present derivative and a known fungicide, insecticide or acaricide with different effects has high efficacy in suppressing or delaying the development of resistance, which is a concern with each single use. In some cases, as shown in the examples, the activity is improved by a synergistic effect, which is economically advantageous.

To prepare the above-mentioned mixture, an active ingredient comprising the compound (I) of the present invention and at least one known fungicide, insecticide or acaricide component, a suitable carrier and an auxiliary agent For example, emulsifiers, dispersants, stabilizers, suspending agents, penetrants, etc. are compounded, and wettable powders, aqueous solvents, emulsions, liquids, sols (flowables), oils, powders, granules, aerosols are formed in a conventional manner. It may be formulated into an agent. The carrier that can be used may be either solid or liquid as long as it is commonly used for agricultural chemicals, and is not limited to a specific one. When formulating emulsions, wettable powders and sols, surfactants (or emulsifiers) are used for the purpose of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading, etc. However, the present invention is not limited to this. In addition to these, various auxiliary agents, and if necessary, stabilizers such as antioxidants and ultraviolet absorbers and coloring agents can also be used.

The content (%) of the active ingredient of the present invention in these preparations is in the range of 1 to 90% (weight%: the same applies hereinafter) for wettable powders, aqueous solvents, emulsions, solutions and sols. In the case of oils, powders and granules, it can be in the range of 0.5 to 10%, and in the case of aerosols, it can be in the range of 0.01 to 2%. The mixing ratio of the compound (I) of the present invention to other fungicide, insecticide or acaricide component is generally 1 to 1% by weight, and generally the latter is 0.01 to 99% by weight. However, it is preferably 0.1 to 20% by weight. These preparations can be diluted to an appropriate concentration and applied to various uses by foliage application, seed treatment, soil treatment, water application or direct application depending on the purpose.

[0030]

The present invention will be described more specifically with reference to the following examples. Incidentally, the present invention, unless exceeding the gist, the active ingredients of the formulation examples shown in the following examples and the compounding ratio thereof,
It is not limited to the auxiliary component and the amount added.

Formulation Example 1 10% by weight of the derivative, 10% by weight of compound a or b as other bactericidal ingredients, 35% by weight of xylene, 30% by weight of N, N-dimethylformamide, 3005X sorbol
(Polyoxyethylene-based surfactant: trade name of Toho Chemical Industry Co., Ltd.) was added in an amount of 15% by weight and uniformly mixed and dissolved to obtain each emulsion. Compound a in this case is represented by (2RS,
3SR) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-
Fluorophenyl) propyl] -1H-1,2,4-triazole (epoxyconazole), and compound b is (RS) -1-p-
Each represents chlorophenyl-4,4-dimethyl-3- (1H-1,2,4-triazol-1-ylmethyl) pentan-3-ol (tebuconazole).

Formulation Example 2 10% by weight of the derivative, compound 1 as another bactericidal component
0% by weight, Carplex # 80 (white carbon:
10% by weight of Shionogi & Co., Ltd.), 62% by weight of di-crite SP (mixture of kaolinite and sericite: trade name of D-Crite Industry Co., Ltd.) and 8% by weight of calcium ligninsulfonate In addition, they were uniformly mixed by a jet air-mill to obtain each wettable powder. Compound c in this case represents methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (benlate).

Formulation Example 3 10% by weight of this derivative, 20% by weight of d or e or f as another fungicide, and 10% by weight of Carplex # 80 (white carbon: trade name of Shionogi & Co., Ltd.) %, J-
Klite SP (a mixture of kaolinite and sericite:
52% by weight of Di-Cright Industry Co., Ltd.) and 8% by weight of calcium ligninsulfonate were uniformly mixed by a jet air mill to obtain each wettable powder. Compound d in this case is dimethyl 4,4- (o-phenylene) bis
Compound (e) is N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboxyimide (procimidon)
And compound f represents 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidin-1-carboxamide (Robral), respectively.

Formulation Example 4 10% by weight of the derivative, 5% by weight of g as another fungicide,
Carplex # 80 (white carbon: Shionogi Pharmaceutical Co., Ltd.) 10% by weight and Di-Cryte SP (a mixture of kaolinite and sericite: Di-Crite Industry Co., Ltd.) at 67%. 8% by weight of calcium ligninsulfonate and 8% by weight were mixed uniformly by a jet air mill to obtain each wettable powder. Compound g in this case
Represents methyl-N- (2-methoxyacetyl) -N- (2,6-xylyl) -DL-alaninate.

Formulation Example 5 10% by weight of the derivative, 3 or h or i as other fungicides
0% by weight, Carplex # 80 (white carbon:
10% by weight of Shionogi & Co., Ltd.), 42% by weight of di-crite SP (mixture of kaolinite and sericite: trade name of di-crite industry), and 8% by weight of calcium ligninsulfonate In addition, they were uniformly mixed by a jet air-mill to obtain each wettable powder. In this case, the compound h is 2,3-dichloro-N-4-fluorophenylmaleimide (fluoroimide), and the compound i is (±) -cis
-4- [3- (4-tert-butylphenyl) -2-methylpropyl] -2,
Each represents 6-dimethylmorpholine (fenpropimorph).

Next, test examples using the mixtures prepared as the respective formulations will be described. Test Example 1 Wheat powdery mildew control / mixed effect test Wheat at the 1-2 leaf stage grown in a 6 cm diameter pot (cultivar:
Norin 61) with the disinfectant composition of the present invention and the single agent obtained in Formulation Examples 1 to 5 as a spreading agent (Nonipolsoft SS)
-90: Sanyo Kasei Kogyo Co., Ltd.) was dispersed in water containing 100 ppm, diluted to a predetermined concentration of the active ingredient, and sprayed with foliage at a rate of 10 ml per pot. After air-drying of chemicals, wheat powdery mildew (Erysiphe graminis f.sp)
After exposure and inoculation with spores obtained from wheat leaves infected with Tritici), the leaves were allowed to stand in a greenhouse for 7 to 10 days. For the evaluation, the diseased area ratio of each leaf was evaluated after a predetermined number of days, and the control value was calculated by the following formula.

[0037]

[Equation 1] Control value (%) = {1- (average disease area ratio of treated area) / (average disease area rate of untreated area)} × 100

When determining the degree of synergistic action, the following Limpel equation (Pesticide Science. (19)
87); 19 309-315 p.312).

[0039]

E = (X + Y) −XY / 100

That is, in the above equation, E, X and Y indicate the following, respectively. Agent A (a ppm) and Agent B
(b ppm), E is the theoretically expected control value (%) when treated with a + b ppm, and X is A ppm
Control value (%) when Y was treated with Y
Is the actual control value (%) when treated with. That is, when the control value (%) obtained by mixing the A agent and the B agent is larger than the value of E calculated by the above-described Limpel equation,
It is determined that the combination of the agent A and the agent B has a synergistic effect. Table 1 shows the control value and the degree of synergistic effect calculated by these formulas.

Test Example 2 Wheat Leaf Rust Control Mixing Effect Test Wheat at the 1-2 leaf stage grown in a 6 cm diameter pot (cultivar:
A diluted solution having a predetermined concentration prepared in the same manner as in Test Example 1 was sprayed on foliage at a rate of 10 ml per pot. After air-drying of chemicals, wheat leaf rust (Puccinia recondi
After spraying and inoculating a spore suspension obtained by grinding the wheat leaves affected by ta), the leaves were kept in a moist room at 22 ° C. for 24 hours, and then left in a greenhouse water bath for 7 days. Evaluation evaluated the diseased area ratio of each leaf, calculated the control value by the same method as in Test Example 1,
The degree of synergy was determined. Table 2 shows the results.

[0042]

[Table 1]

[0043]

[Table 2]

Test Example 3 Test for Controlling Mixture of Cucumber Gray Mold Disease A cucumber (variety: four-leaf) at the cotyledon stage grown in a 9 cm-diameter pot was diluted with a predetermined concentration prepared in the same manner as in Test Example 1 per pot. Foliage was sprayed at a rate of 10 ml. After the chemical solution was air-dried, the cucumber cotyledons were cut at the petiole and held in a small vat under wet-room conditions. At the center of the cotyledon, a small piece of filter paper having a diameter of 8 mm containing a spore suspension of Botrytis cinerea cultured on potato decoction agar medium with sucrose was placed and inoculated. 22
It was left for 5 days in a humidity chamber at ℃. For the evaluation, the diameter of the lesion portion of each leaf was measured, and the control value was calculated by the following formula.

[0045]

[Equation 3] Control value (%) = {1− (average lesion diameter of treated section) / (average lesion diameter of untreated section)} × 100

The degree of synergistic effect was determined in the same manner as in Test Example 1. The results are shown in Table-3.

[0047]

[Table 3]

Test Example 4 Tomato Blight Control Effect Mixed Test A 3-5-leaf tomato grown in a 9 cm diameter pot (cultivar:
Red Cherry) was sprayed with foliage at a rate of 10 ml per pot, with a diluted solution having a predetermined concentration prepared in the same manner as in Test Example 1. After air-drying the chemical, Phytophthora inf
estans), spray inoculated with a zoospore sac suspension obtained from tomato leaves, and kept in a humidity chamber at 22 ° C. for 24 hours.
It was left on the water tank in the greenhouse for 7 days. For evaluation, the diseased area ratio of each leaf was evaluated, the control value was calculated in the same manner as in Test Example 1, and the degree of synergistic effect was determined. The results are shown in Table-4.

[0049]

[Table 4]

[0050]

EFFECTS OF THE INVENTION The fungicide of the present invention not only complements the control spectrum but also has a clear synergistic effect as shown in the examples, so that each active ingredient can be reduced. In addition, this leads to a reduction in the total amount of drug used and the total number of times of use, which is economically advantageous. Further, the combination of different effects is also highly effective in suppressing or delaying the development of drug resistance, which is a concern with each single use.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 47/38 A01N 47/38 C

Claims (4)

[Claims] 1. A compound represented by the following general formula (I)(In the above general formula, Ar is an aryl group or a heteroaryl
Y represents a hydrogen atom, a halogen atom, C₁-C_Fourof
Alkyl group, C₁-C_FourHaloalkyl group of C ₁-C_Four
An alkoxy group of C₁-C_FourHaloalkoxy group, C₁
-C_FourAn alkylthio group of C_Two-C₆Alkynyloqui
Represents a cyano group, a cyano group, a nitro group or an aryl group;
Represents an integer of 1 to 3. ), And the optical rotation is chloro.
An optically active method characterized by showing a negative value in the form
Toxiiminoacetamide derivative and one selected from group A
Or agricultural and horticultural products containing multiple compounds as active ingredients
Disinfectant. Group A: Triazole fungicide, morpholine fungicide,
Nzimidazole fungicide, dicarboximide fungicide
Agents, phenylamide fungicides, maleimide fungicides. 2. The agricultural / horticultural fungicide according to claim 1, wherein the optically active methoxyiminoacetic acid amide derivative is represented by the following general formula (II). Embedded image 3. The group A is a wheat fungicide containing a triazole fungicide such as epoxyconazole or tebuconazole, or a morpholine fungicide fenpropimorph. A bactericide according to item 1. 4. Group A: benomyl or thiophanate methyl as a benzimidazole fungicide, procymidone or iprodione as a dicarboximide fungicide, metalaxyl as a phenylamide fungicide, or fluoroimide as a maleimide fungicide. The fungicide according to claim 1 or 2, which is a fungicide for vegetables, fruit trees, and turfgrass containing tea.