JPH09235262A - New benzamidoxime derivative, its production and fungicide for agriculture and horticulture - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful as a fungicide for agriculture and horticulture. SOLUTION: This new benzamidoxime derivative is represented by formula I [R1 is a 1-4C alkyl, a 2-4C alkenyl or a 2-4C alkynyl; R2 is phenyl or a heterocyclic ring; X' is a 1-4C haloalkoxy; X<2> to X<5> are each H, a halogen, a 1-4C alkyl, a 1-4C haloalkyl, a 1-4C alkoxy, etc.; X<1> and X<2> may together form a 1-4C haloalkylenedioxy; (r1 ) and (r2 ) are each H, a halogen, a 1-4C alkyl, a 1-4C alkoxy, etc.; (r1 ) and (r2 ) may together form carbonyl], e.g. N'- cyclopropylmethyloxy-Nphenylacetyl-2,3-dichloro6-trifluoromethoxybenza midine. The compound of formula I is obtained by reacting a compound of formula II with a compound of formula III (Hal is a halogen) in a solvent (e.g. toluene) and necessary, in the presence of a base at 0 deg.C to at a boiling point of the solvent for 10min to several 10min. The compound is effective in controlling disease damage of powdery mildew of wheat, powdery mildew of cucumber, powdery mildew of strawberry, etc.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel benzamide oxime derivative, a production method and an agricultural / horticultural fungicide.

[0002]

2. Description of the Related Art Conventionally, when cultivating agricultural and horticultural crops, many controlling agents have been used for disease of crops.
It is not always satisfactory because its control efficacy is insufficient, its use is restricted by the emergence of drug-resistant pathogens, it causes phytotoxicity and pollution to plants, and has strong toxicity to humans and fishes. There are many difficult control agents to call. Therefore, there is a strong demand for the emergence of a drug that can be used safely with few such drawbacks.

The benzamide oxime derivatives related to the compounds of the present invention and their fungicides are disclosed in
No. 6,453 is known. However, the biological activity is not always sufficient for practical use.

[0004]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a novel compound which can be used as an agricultural and horticultural fungicide which can be synthesized industrially advantageously, has a certain effect, and can be used safely.

[0005]

The present invention relates to a benzamide oxime derivative represented by the formula [I], a production method and a fungicide for agricultural and horticultural use.

[0006]

[Chemical 6]

[In the formula, R ₁ is an optionally substituted C _1-
A C ₄ alkyl group, an optionally substituted C ₂ -C ₄ alkenyl group or an optionally substituted C ₂ -C ₄ alkynyl group, R ₂ is a phenyl group which may have a substituent or a substituted group Represents a heterocycle which may have a group, X
¹ represents a C ₁ -C ₄ haloalkoxy group, X ² ,
X ^3, X ^4, X ^5, independently of one another, a hydrogen atom, a halogen atom, C ₁ -C ₄ alkyl group, C ₁ -C ₄ haloalkyl groups, C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ A haloalkoxy group, a C ₁ -C ₄ alkylthio group, a C ₁ -C ₄ alkylsulfinyl group, a C ₁ -C ₄ alkylsulfonyl group, a nitro group, an amino group or a C ₁ -C ₄ alkylcarbonylamino group, and X ¹ and X ² may together form a C ₁ -C ₄ haloalkylenedioxy group. r ₁ and r ₂ are each independently a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₄ alkoxy group, a C ₁ -C ₄ alkylthio group or It represents an optionally substituted amino group, and r ₁ and r ₂ may together form a carbonyl group. ]

[0008] In the present invention, the C ₁ -C ₄ alkyl group substituted C ₁ -C ₄ may be an alkyl group R _1, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group , T-butyl group and the like. The C ₂ -C ₄ alkenyl group optionally substituted C ₂ -C ₄ alkenyl group R _1, a vinyl group, 1-
A propenyl group, a 2-propenyl group, an isopropenyl group,
Examples thereof include a 1-butenyl group, a 2-butenyl group and a 3-butenyl group. Further, R ₁ may be substituted C ₂ -C
The C ₂ -C ₄ alkynyl group ₄ alkynyl group, an ethynyl group, propargyl group, 2-butynyl group, 3-butynyl group.

As the substituent of R ₁ which may be substituted, C ₁ -C ₄ alkyl group, C ₂ -C ₄ alkenyl group which may be substituted and C ₂ -C ₄ alkynyl group which may be substituted, C ₃ -C ₈ cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, fluorine,
Halogen atom such as chlorine, bromine, iodine, methoxy group, ethoxy group, propyloxy group, isopropyloxy group,
Examples thereof include a C ₁ -C ₄ alkoxy group such as a butyloxy group, an isobutyloxy group and a t-butyloxy group, a cyano group and the like.

Examples of the optionally substituted hetero ring of R ₂ include a pyridine ring optionally substituted with a halogen atom, a lower alkyl group, a lower haloalkyl group or a lower alkoxy group, a thiophene ring, a pyrazole ring, an imidazole ring, 1 hetero atom such as N, O, S such as pyrrole ring, pyrimidine ring, oxazole ring or thiazole ring
Examples include 5- to 6-membered aromatic heterocycles containing 4 to 4.

Examples of the substituent of the phenyl group which may have a substituent and the heterocyclic group which may have a substituent of R ₂ include a halogen atom such as fluorine, chlorine and bromine, methyl, ethyl and propyl. , C _2, such as C ₁ -C ₄ alkyl groups, methoxy, ethoxy, propoxy, isopropoxy, butoxy, C ₁ -C ₄ alkoxy groups, such as t-butoxy group, an allyloxy group such as isopropyl, butyl, t- butyl group -C ₄ alkenyloxy group, propargyl C ₁ -C ₄ alkynyloxy groups such as oxy group, chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, Jifururoromechiru, trichloromethyl, trifluoromethyl, tribromomethyl, trifluoroethyl, pentafluoroethyl C ₁ -C ₄ haloalkyl groups, such as fluoroethyl group, chloromethoxy, Furorome Alkoxy, bromo, methoxy, dichloromethoxy, difluoromethyl Rollo, trichloromethoxy, trifluoromethoxy, tribromomethoxy, such as C ₁ -C ₄ haloalkoxy groups such as trifluoroethoxy group.

Examples of the C ₁ -C ₄ haloalkoxy group for X ¹ include chloromethoxy, fluoromethoxy, bromomethoxy, dichloromethoxy, difluromethoxy, trichloromethoxy, trifluoromethoxy, tribromomethoxy, trifluoroethoxy and tetrafluoro. Ethoxy,
Examples include pentafluoroethoxy group.

Examples of X ² , X ³ , X ⁴ and X ⁵ are halogen atoms such as fluorine, chlorine, bromine and iodine,
A linear or branched C ₁ -C ₄ alkyl group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, Difluoromethyl group, trifluoromethyl group, bromomethyl group, dibromomethyl group chloroethyl group, fluoroethyl group, dichloroethyl group, difluoroethyl group, trifluoroethyl group, tetrafluoroethyl group, pentafluoroethyl group, chloropropyl group, fluoropropyl group, Perfluoropropyl group, chloroisopropyl group, fluoroisopropyl group, perfluoroisopropyl group, chlorobutyl group, fluorobutyl group, perfluorobutyl group, chloroisobutyl group, fluoroisobutyl group, pafluoroisobutyl group, chloro-s-
A linear or branched C ₁ -C ₄ group such as a butyl group, a fluoro-s-butyl group, a perfluoro-s-butyl group, a chloro-t-butyl group, a fluoro-t-butyl group, and a perfluoro-t-butyl group. C ₁ -C ₄ alkoxy groups such as haloalkyl group, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, t-butyloxy group, trifluoromethoxy group, trifluoroethoxy group, pentafluoro C ₁ -C ₄ haloalkoxy group such as ethoxy group and trichloromethoxy group, C ₁ -C ₄ alkylthio group such as methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group and t-butylthio group. , Methylsulfinyl group, ethylsulfinyl group, propylsulfinyl group, iso Russia Pils sulfinyl group,
C ₁ -C ₄ alkylsulfinyl group such as butylsulfinyl group, methylsulfonyl group, ethylsulfonyl group,
C ₁ -C ₄ alkylsulfonyl group such as propylsulfonyl group, isopropylsulfonyl group, butylsulfonyl group, nitro group, amino group, acetylamino group, C ₁ -C ₄ alkylcarbonylamino group such as propionylamino group, benzoylamino group And X ¹ and X ²
Together, a difluoromethylenedioxy group, a dichloromethylenedioxy group, a 1,1-difluoroethylenedioxy group, a 1,2-difluoroethylenedioxy group,
The case of forming a C ₁ -C ₄ haloalkylenedioxy group such as a 1,1,2,2-tetrafluoroethylenedioxy group can be mentioned.

Further, as r ₁ and r ₂ , a hydrogen atom, a halogen atom such as fluorine, chlorine, bromine and iodine, methyl, ethyl, propyl, isopropyl, butyl and s-
Butyl, C ₁ -C ₄ alkyl group such as t- butyl, trifluoromethyl group, trichloromethyl group, trifluoroethyl group, C ₁ -C ₄ haloalkyl group such as a pentafluoroethyl group, a methoxy group, an ethoxy group, a propoxy C ₁ such as group, isopropoxy group, butoxy group, t-butoxy group, etc.
-C ₄ alkoxy group, methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, t
A C ₁ -C ₄ alkylthio group such as a -butylthio group, or a (C ₁ -C ₄ alkyl group such as a methyl group or an ethyl group,
Acetyl group, a benzoyl group which may have a substituent,
Represents a mono- or di-N-substituted amino group with a substituent (such as a phenyl group which may have a substituent), and r ₁ and r ₂ together form a carbonyl group. The case etc. can be illustrated.

[0015]

BEST MODE FOR CARRYING OUT THE INVENTION

(Production of Compound) The compound of the present invention can be produced by the following method.

[0016]

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(In the formula, Hal represents a halogen atom and R
₁ , R ₂ , X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as described above. The reaction is carried out by reacting compound (II) with compound (III) in an organic solvent, optionally in the presence of a base, in the temperature range from 0 ° C. to the boiling point of the solvent used for 10 minutes to several tens of hours. . As the solvent that can be used here, aromatic hydrocarbons such as benzene and toluene, ethers such as THF and diethyl ether, halogenated hydrocarbons such as chloroform and dichloromethane, D
Examples thereof include amides such as MF, DMSO, acetonitrile and the like. The solvent may be used alone or as a mixture of several solvents. As the base, pyridine, triethylamine, DBU, sodium hydride, sodium carbonate, potassium carbonate and the like can be used. After the completion of the reaction, the desired product can be obtained by subjecting to ordinary post-treatment and purification by silica gel column chromatography or the like. The starting compound (II) of the present invention can be synthesized, for example, by the following method.

[0018]

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(In the formula, L represents a leaving group such as a halogen atom, a paratoluenesulfonyloxy group and a methanesulfonyloxy group, and R ₁ , X ¹ , X ² , X ³ , X ⁴ and X ⁵ are as defined above. The first step reaction is the reaction of the nitrile compound (IV) and hydroxylamine hydrochloride in the presence of a base in a solvent in the temperature range from 0 ° C. to the boiling point of the solvent used for 10 minutes to several tens of hours. The benzamide oxime compound (V) is thus obtained. As the solvent to be used, alcohols such as methanol, ethanol and propanol, ethers such as THF and diethyl ether, DMF
And amides such as DMSO, water, etc.
Used alone or as a mixture of several kinds. As a base,
Sodium carbonate, sodium bicarbonate, potassium carbonate,
Sodium hydroxide, potassium hydroxide, triethylamine, pyridine and the like can be used.

The next reaction is carried out in the presence of a base in an inert solvent,
The compound (V) is reacted with the compound (VI) or (VII) in the temperature range from -15 ° C to the boiling point of the solvent used for 10 minutes to several tens of hours to obtain the starting compound (II). Here, the solvent can be used alone or as a mixture of several kinds, and as the solvent used, benzene,
Examples thereof include aromatic hydrocarbons such as toluene, ethers such as THF and diethyl ether, ketones such as acetone and methyl ethyl ketone, amides such as DMF and DMA, DMSO, acetonitrile, water and the like. Examples of the base include metal alkoxides such as sodium methoxide and sodium ethoxide, inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate and sodium hydrogen carbonate, and organic bases such as triethylamine and pyridine. Can be used.

Further, depending on the solvent system and the base, the following catalysts can be used. As the catalyst, ethers such as 18-crown-6 and dicyclohexyl-18-crown-6, tetrabutylammonium bromide, its chloride, quaternary ammonium salts such as methyltrioctylammonium chloride and benzyltriethylammonium chloride, tetraphenyl Examples include phosphonium compounds such as phosphonium bromide and hexadecyltributylphosphonium iodide. The structure of the compound of the present invention was determined by NMR, IR, MS and the like.

[0022]

The present invention will be described in more detail with reference to the following examples. Example 1 Production of N'-cyclopropylmethyloxy-N-phenylacetyl-2,3-dichloro-6-trifluoromethoxybenzamidine (Compound No. 40)

[0023]

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N'-cyclopropylmethyloxy-2,
0.30 g of 3-dichloro-6-trifluoromethoxybenzamidine was dissolved in 5 ml of toluene, 0.16 g of phenylacetyl chloride was added, and the mixture was heated under reflux for 2.6 hours. After cooling, water and benzene were added, the layers were separated, and the organic layer was dried over anhydrous magnesium sulfate. This was concentrated and purified by silica gel column chromatography to obtain 0.32 g of the desired product. Melting point 94-97 ° C

Next, production examples of these raw material compounds will be shown as reference examples. Reference Example 1 Production of 2,3-dichloro-6-trifluoromethoxybenzamide oxime

[0026]

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Hydroxylamine hydrochloride (5.95 g) was dissolved in methanol (45 ml) to give sodium carbonate (4.99).
An aqueous solution prepared by dissolving g in 10 ml of water was added. To this, with stirring, 5.48 g of 2,3-dichloro-6-trifluoromethoxybenzonitrile was added at 55 ° C., and further 60
Stirred at C for 3 hours. Methanol was distilled off from the reaction solution under reduced pressure and then extracted with ethyl acetate. After 50 ml of 3N hydrochloric acid aqueous solution was added thereto to separate the layers, the aqueous layer was cooled to 10
% Aqueous sodium hydroxide solution to neutralize the pH to 9 and extract again with ethyl acetate. After drying over anhydrous magnesium sulfate,
The solvent was distilled off under reduced pressure to obtain 3.0 g of the title compound. Melting point 10
6-109 ° C

Reference Example 2 N'-Cyclopropylmethyloxy-2,3-dichloro-6-trifluoromethoxybenzamidine

[0029]

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2.0 g of 2,3-dichloro-6-trifluoromethoxybenzamide oxime and 1.12 g of cyclopropylmethyl bromide were dissolved in 20 ml of DMF and 0.28 g of 60% oily sodium hydride was added at about 5 ° C.
Was slowly added. Furthermore, it stirred at 10 degreeC or less for 3 hours. The reaction solution was poured into ice water, extracted with diethyl ether, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.46 g of the title compound. Melting point 74-76 ° C

Reference Example 3 N'-Cyclopropylmethyloxy-2,3-difluoro-6-trifluoromethoxybenzamidine

[0032]

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2,3-difluoro-6-trifluoromethoxybenzamide oxime (4.48 g) and cyclopropylmethyl bromide (3.54 g) were added to 45 m of chloroform.
The solution was dissolved in 1 and at room temperature, 0.56 g of tetrabutylammonium bromide and then 10 ml of 10% sodium hydroxide aqueous solution were added with stirring. 18 at 30-40 ° C
Stirred for hours. Water and chloroform were added to the reaction solution, the layers were separated, washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound.2.
0 g was obtained. Melting point 69-70 ° C

The compounds of the present invention produced in the same manner as in Example 1 are summarized in Table 1. Incidentally, X ¹ to X ⁵ in Table 1, R _1, R _2, r ₁ and r ₂ are, X ¹ to X ^5, R ₁ in the compound represented by the general formula [I],
Corresponds to R ₂ , r ₁ and r ₂ .

[0035]

[Table 101]

[0036]

[Table 102]

[0037]

[Table 103]

[0038]

[Table 104]

[0039]

[Table 105]

[0040]

[Table 106]

[0041]

[Table 107]

[0042]

[Table 108]

Since the compound of the present invention has an excellent bactericidal activity against a wide variety of filamentous fungi,
It can be used for controlling various diseases that occur during cultivation of agricultural and horticultural crops including grass and grass. For example, rice blast (Pyricularia oryzae) sheath blight (Rhizoctonia solani) stupid seedling (Gibberella fujikuroi) sesame leaf blight (Cochliobolus miyabeanus) barley brown smut (Ustilago nuda) wheat red mold (Gibberella zeae) Puccinia recondita) Eye spot disease (Pseudocercosporella herpotrichoides) Fusarium wilt (Leptosphaeria nodorum) Powdery mildew (Erysiphe graminis f. Sp. Tritici) Red snow rot (Micronectriella nivalis) Potato plague (Phytophthora infestans discolor) ) Sugar beet Brown leaf spot (Cercospora beticola) Cucumber Powdery mildew (Sphaerotheca fuliginea) Sclerotinia (Sclerotinia sclerotiorum) Gray mold (Botrytis cinerea) Downy mildew (Pseudoperonospora cubensis) ) Eggplant Black Blight (Corynespora melongenae) Onion Gray Rot (Botrytis allii) Strawberry Powdery mildew (Sohaerotheca humuli) Apple Powdery mildew (Podosphaera leucotricha) Black scab (Venturia inaequalis) Moniliania mali (Monilinia mali) Oyster Anthracnose (Gloeosporium kaki) Peach ash (Monilinia fructicola) Grape powdery mildew necator cin Downy mildew (Plasmopara viticola) Pear Red scab (Gymnosporangium asiaticum) Black spot (Alternaria kikuchiana) Tea Ring spot (Pestalotia theae) Anthrax (Colletotrichum theae-sinensis) Citrus scab (Elisinoe fawcetti) Blue illium (Pills) italicum) It can be used for the control of western turf, Sclerotinia borealis, etc.

In recent years, resistance to benzimidazole agents and ergosterol biosynthesis inhibitors has been developed in various pathogenic bacteria, resulting in lack of efficacy of these agents.
There is a need for a drug that is also effective against pathogenic bacteria of the resistant strain. The compound of the present invention is a drug having an excellent bactericidal effect not only on susceptible strains but also on pathogenic bacteria of benzimidazole agents and ergosterol biosynthesis inhibitor resistant strains. Diseases more preferably applied include various powdery mildews such as wheat powdery mildew, cucumber powdery mildew, and strawberry powdery mildew. The compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contacts such as ship bottoms and fish nets. Further, by mixing the compound of the present invention with paints, fibers, etc., it can be used as an antibacterial and antifungal agent for walls, bathtubs, shoes and clothes. Further, some of the compounds of the present invention exhibit insecticidal, acaricidal and herbicidal activities.

When the compound of the present invention thus obtained is actually applied, it can be used in a pure form without adding other components, and a general pesticide can be used for the purpose of use as an agricultural chemical, that is, , Wettable powder, granules, powder, emulsion, water solvent,
It can also be used in the form of a suspension, flowable or the like.
When a solid agent is intended as an additive and a carrier,
Soybean grains, plant powders such as wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite, mineral fine powders such as clay, and organic and inorganic compounds such as sodium benzoate, urea, and mirabilite are used. When a liquid dosage form is intended, petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethylsulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, water Is used as a solvent.
In order to obtain a uniform and stable form in these preparations, a surfactant may be added, if necessary.

The amount of active ingredient is preferably 5 to 70%. The wettable powder, emulsion, and flowable obtained in this manner are diluted to a predetermined concentration with water to prepare a suspension or an emulsion, and the powder and granules are used as they are by spraying them on plants. The compound of the present invention exerts a sufficient effect when used alone, but may be used in combination with one or more kinds of various fungicides, insecticides, acaricides, or synergists.

Examples of the fungicides, insecticides, acaricides, nematicides and plant growth regulators which can be used by mixing with the compound of the present invention include the following. Bactericide: Copper agent: basic copper chloride, basic copper sulfate, etc. Sulfur agent: thiuram, manneb, mancozeb, polycarbamate, propineb, ziram, zineb, etc. Polyhaloalkylthio agent: captan, dichlorfluanid, folpet, etc. Organic Chlorine agent: chlorothalonil, phthalide, etc.Organic phosphorus agent: IBP, EDDP, tolclofos-methyl,
Pyrazophos, fosetyl, etc. Benzimidazole agents: thiophanate methyl, benomyl, carbendazim, thiabendazole, etc. Dicarboximide agents: iprodione, vinclozolin, procymidone, fluorimide, etc. Carboxamide agents: oxycarboxin, mepronil, furtranil, teclophthalam, trichlamide, pencyclone, etc. Acyl alanine Agents: metalaxyl, oxadixyl, furalaxyl, etc. SBI agents: triadimefon, triadimenol, bitertanol, microbutanyl, hexaconazole, propiconazole, trifumizole, prochloraz, pefrazoate, phenalimol, pyrifenox, triphorin, flucylazole, etaconazole, diclobone. Sol, fluotrimazole, flutriafen, penco Zole, diniconazole, cyproconazole, imazalil, tridemorph, fenpropimorph, butiobate, etc. Antibiotic agents: polyoxin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin, etc. Others: propamocarb hydrochloride, quintozene, hydroxyisoxazole, meta Sulfocarb, anilazine,
Isoprothiolane, probenazole, quinomethionate, dithianon, dinocab, diclomedine, mepanipyrim, ferimzone, fluazinam, pyroquilon, tricyclazole, oxolinic acid, dithianon, iminoctadine acetate, simoxanil, pyrrole nitrine, metasulfocarb, dietofencarb, fenapacryl, vinapacryl, vinapacryl, vinapacryl, vinapacryl. , Dodine, dimethomorph, phenazine oxide, etc.

Insecticides and acaricides: Organophosphorus and carbamate insecticides: fenthion, fenitrothion, diazinon, chlorpyrifos, ES
P, bamidothion, fentoate, dimethoate, formothion, marathon, trichlorfon, thiomethone,
Hosmet, dichlorvos, acephate, EPBP,
Methyl parathion, oxydimetone methyl, ethion,
Salithion, cyanophos, isoxathion, pyridafenthion, phosalone, methithione, sulprophos, chlorfenbinphos, tetrachlorbinphos, dimethylvinphos, propaphos, isofenphos, ethylthiomethone, profenophos, pyraclofos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, Carbofuran, Carbosulfan, Benfuracarb, Fratiocarb, Propoxur, BPMC,
MTMC, MIPC, carbaryl, pirimicarb, ethiophencarb, phenoxycarb, cartap, thiocyclam, bensultap and the like. Pyrethroid insecticides: permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, protrin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, Cycloprothrin, trolametrin, silafluofen,
Blofenprox, Acrinasuri etc.

Benzoylurea-based and other insecticides: diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, methoprene, benzoepine, diafenthiu. Ron, imidacloprid, fipronil, nicotine sulfate, rotenone, methaaldehyde, machine oil, microbial pesticides such as BT and insect pathogenic viruses.

Nematicides: fenamiphos, fosthiazate and the like. Acaricide: chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate,
Hexthiazox, fenbutatin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentezine, cyhexatin, pyridaben, fenpyroximate, tebufenpyrad, pyrimidifen, phenothiocarb, dienochlor and the like. Plant growth regulator: gibberellins (eg gibberellin A3
, Gibberellin A4, Gibberellin A7) IAA, NA
A.

[0051]

Next, some examples of the composition of the present invention will be shown, but the additives and the addition ratios should not be limited to these examples, but can be widely varied. The parts in the formulation examples are parts by weight.

[0052]

【Example】

[Bactericide] Next, some examples of the composition of the present invention will be described. However, the additives and the addition ratio are not limited to these examples, and can be varied in a wide range. Parts in Formulation Examples are parts by weight.

Example 2 Wettable powder Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate ester 4 parts Alkylnaphthalene sulfonate 3 parts Active ingredient 40 if uniformly mixed and finely ground
% Wettable powder.

Example 3 Emulsion Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts By mixing and dissolving the above, an emulsion of 30% of the active ingredient is obtained.

Example 4 Dust formulation Compound of the present invention 10 parts Talc 89 parts Polyoxyethylene alkylallyl ether 1 part The above ingredients are uniformly mixed and finely pulverized to obtain 10 parts of active ingredient.
% Powder.

Example 5 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Sodium phosphate 1 part The above components are well pulverized and mixed, and water is added and kneaded well,
The granules are dried by granulation to obtain granules having an active ingredient of 5%.

Example 6 Suspension Compound of the present invention 10 parts Sodium lignin sulfonate 4 parts Sodium dodecylbenzene sulfonate 1 part Xanthan gum 0.2 parts Water 84.8 parts The above are mixed until the particle size becomes 1 micron or less. Wet milling gives a suspension with 10% active ingredient.

Next, it is shown in Test Examples that the compound of the present invention is useful as an effective component of various plant disease controlling agents. Regarding the control effect, the condition of the test plant at the time of the investigation, that is, the degree of lesions appearing on leaves, stems, etc. was visually observed.

Test Example 1 Wheat Powdery Mildew Control Test (Prevention) Wheat seedlings cultivated in unglazed pots (cultivar "Chihoku")
A sufficient amount of the emulsion of the compound of the present invention was sprinkled on the active ingredient at a concentration of 12.5 ppm. After spraying, it is naturally dried at room temperature, and the wheat powdery mildew (Erysiphe graminia)
f. sp. The conidia of Tritici) were shaken off and inoculated, and the disease was developed in a greenhouse at about 20 ° C. for 7 days. The appearance of spots on the leaves was compared with that of no treatment, and the control effect was determined. As a result, the following compounds were confirmed to have a remarkable controlling effect.
Compound No. in Table 1 1, 2, 16, 18, 40, 4
1, 42, 43, 45, 48, 51, 57, 228

Test Example 2 Cucumber Powdery Mildew Control Test (Prevention) An emulsion of the compound of the present invention was added to a cucumber seedling (cultivar "Sagamihanjiro") cultivated in a unglazed pot with an active ingredient of 12.5 ppm.
Was sprayed at a concentration of. After spraying, air-dry at room temperature, and then cucumber powdery mildew (Sphaerotheca fulig)
The conidia of (inea) were shaken off and inoculated, and the disease was caused to occur in a thermostatic chamber at about 25 ° C for 11 days. The state of lesion appearance on the leaves was compared with that of the untreated seeds to determine the control effect. As a result, the following compounds were confirmed to have excellent control effects. Compound No. in Table 1 1, 2, 16, 18, 40, 41, 42, 4
3,57

On the other hand, the following Japanese Unexamined Patent Publication No.
With the compound described in No. 6453 (compound No. 87 in Table 1 on page 12 of the specification), almost no control effect against wheat powdery mildew and cucumber powdery mildew was observed.

[0062]

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From the above, it can be seen that the compound of the present invention has an excellent preventive effect against not only wheat powdery mildew but also cucumber powdery mildew as compared with the control drug.

Test Example 3 Cucumber powdery mildew control test (volatility) At a concentration of 50 ppm of the active ingredient, 10 μl of an emulsion of the compound of the present invention was dripped onto an aluminum foil having a diameter of 1 cm, and naturally dried at room temperature and then placed in a unglazed pot. It was adhered on the leaves of a cultivated cucumber seedling (cultivar "Sagamihanshiro"). 24 hours later, the conidia of the powdery mildew of cucumber were shaken off and inoculated, and the disease was caused for 11 days in a thermostatic chamber at about 25 ° C. The appearance state of lesions on the leaves was compared and investigated with no treatment, and the case where an inhibition circle having a diameter of 2 cm or more was formed around the aluminum foil was determined to have a volatile effect.
As a result of the test, the following compounds were found to have a volatile effect. Compound No. in Table 1 1, 16, 18

No volatile effect was observed with the control compound. Since the compound of the present invention has volatility, even if there is uneven spraying of the drug, it exerts an excellent bactericidal / control effect even on leaves and fruits to which the drug does not adhere.

[Table 109]

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication location C07C 323/40 7419-4H C07C 323/40 (72) Inventor Takashi Yamanaka Takada character Yanagicho, Odawara City, Kanagawa Prefecture 345 Inside Soda Co., Ltd. Odawara Research Center

Claims (3)

[Claims] 1. A compound of the formula [I] [In the formula, R ₁ represents an optionally substituted C ₁ -C ₄ alkyl group, an optionally substituted C ₂ -C ₄ alkenyl group or an optionally substituted C ₂ -C ₄ alkynyl group, and R 1
₂ represents a phenyl group which may have a substituent or a heterocyclic ring which may have a substituent, X ¹ represents a C ₁ -C ₄ haloalkoxy group, X ² , X ³ , X ⁴ and X ⁵ are independently of each other a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄
Haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄
Haloalkoxy groups, C ₁ -C ₄ alkylthio group, C ₁ -
A C ₄ alkylsulfinyl group, a C ₁ -C ₄ alkylsulfonyl group, a nitro group, an amino group or a C ₁ -C ₄ alkylcarbonylamino group, and X ¹ and X ² together represent a C ₁ -C ₄ A haloalkylenedioxy group may be formed. r ₁ and r ₂ are each independently a hydrogen atom, a halogen atom, a C ₁ -C ₄ alkyl group, C ₁ -C ₄
Haloalkyl group, C ₁ -C ₄ alkoxy group, C ₁ -C ₄
It represents an alkylthio group or an optionally substituted amino group, and r ₁ and r ₂ may be taken together to form a carbonyl group. ] The benzamide oxime derivative represented by these. 2. A compound of the formula [II] [In the formula, R ₁ , X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as described above. ] And a compound of the formula [III] [In the formula, Hal represents a halogen atom, and R ₂ has the same meaning as described above. And a compound represented by the formula [I]: [In the formula, R ₁ , R ₂ , X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as described above. ] A method for producing a benzamide oxime derivative represented by the formula: 3. A compound of the formula [I] [In the formula, R ₁ , R ₂ , X ¹ , X ² , X ³ , X ⁴ and X ⁵ have the same meanings as described above. ] A fungicide for agricultural and horticultural use, comprising one or more benzamide oxime derivatives represented by the following as an active ingredient.