JP2013100234A - Oxime ether derivative or salt thereof and agriculture and horticulture fungicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an agriculture and horticulture fungicide having a new oxime ether derivative or its salt as an active component.SOLUTION: The agriculture and horticulture fungicide includes at least one kind selected from the oxime ether derivative shown by formula (I) or a salt thereof and these compounds as an active component. In formula (1), X is a 1 to 8C alkyl group or the like, n is the substitution number of X and is an integer of 0 to 4, Rand Rare each independently a hydrogen atom, m is the repeating number of the unit in the parentheses and is an integer of 1 to 8, Ris 1 to 8C alkyl group or the like, Ris 1 to 8C alkyl or the like, Ris a hydrogen atom or the like, Y is an oxygen atom or sulfur atom, Z is an oxygen atom or the like, and Q is a pyrazole ring having no substituent or having a substituent.

Description

  The present invention relates to an oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide. More specifically, the present invention relates to a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivative or a salt thereof.

  In the cultivation of agricultural and horticultural crops, various control agents are used against crop diseases. However, many of these control agents have insufficient control efficacy, their use is limited by the emergence of drug-resistant pathogens, cause phytotoxicity and pollution to plants, or are toxic to human fish and have an impact on the environment. It is difficult to say that it is a satisfactory control agent because of the problems such as large For this reason, there is a strong demand for the emergence of a control agent that has few such problems, has a high control effect, and can be used safely.

  In connection with the present invention, an oxyamine derivative (Patent Document 1), an oxime derivative (Patent Document 2), an oxime ether derivative (Patent Document 3), and the like have been proposed.

JP 2004-168683 A Japanese Patent Laid-Open No. 2003-231672 WO2009 / 075112

The oxyamine derivatives, oxime derivatives, oxime ether derivatives or salts thereof described in Patent Documents 1 to 3 can be easily synthesized industrially, have a high control effect, and can be used as a safe control agent. It was. However, the compounds described in Patent Documents 1 to 3 require a relatively large amount of compound (g / ha) required for use as a control agent depending on the target disease. Due to the low permeability of the compound to crops, there was a case where a sufficient control effect was not obtained in practical use.
In view of such circumstances, the present invention can be easily manufactured industrially, has a large control effect even at a low concentration and a small application amount, and has high penetrability and residual effect on many agricultural and horticultural crops. It is an object of the present invention to provide a novel oxime ether derivative or a salt thereof, and an agricultural and horticultural fungicide, which can be an active ingredient of an agricultural and horticultural fungicide that has a reliable disease control effect and can be used safely. .

  The present inventors diligently studied to solve the above problems. As a result, a novel oxime ether derivative having a pyrazole ring group represented by the formula (I) or a salt thereof was obtained. These oxime ether derivatives or salts thereof can be easily produced industrially, and agricultural and horticultural fungicides containing at least one selected from these compounds as an active ingredient have a low concentration and an application rate. At least, the control effect is large, the penetration and retentivity to many agricultural and horticultural crops is high, and the control effect against diseases is certain, and there is little phytotoxicity and pollution to plants, We found that it has excellent safety because it has little impact on the environment. The present invention has been completed by further studies based on these findings.

  That is, the present invention includes the following aspects.

[1] An oxime ether derivative represented by the formula (I) or a salt thereof (hereinafter sometimes referred to as the present compound).

[In formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer of 0 to 4. When n is 2 or more, Xs may be the same or different.
R ¹ and R ² each independently represents a hydrogen atom, a halogen atom, a C 1-8 alkyl group, a C 1-8 haloalkyl group, or an unsubstituted or substituted C 3-8 cycloalkyl group. R ¹ and R ² may be bonded together to form a ring. m represents the number of repeating units in parentheses and is an integer of 1-8. When m is 2 or more, R ¹ and R ² may be the same or different.
R ³ is a hydrogen atom, a C 1-8 alkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 haloalkenyl group, a C 2-8 haloalkynyl group, or an unsubstituted or A C3-8 cycloalkyl group having a substituent is represented.
R ⁴ is a hydrogen atom, a C 1-8 alkyl group, an unsubstituted or substituted C 3-8 cycloalkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 halo. An alkenyl group or a C2-8 haloalkynyl group is represented.
R ⁵ is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl. A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR ⁶ . R ⁶ represents a hydrogen atom or a C1-8 alkyl group.
Q represents an unsubstituted or substituted pyrazole ring group. ]

[2] X is a C1~8 alkyl group, R ^1, R ^2, R ^3, a hydrogen atom and R ⁴ and R ⁵ are each independently or C1~8 alkyl group, Y and Z is oxygen atom , Q is an unsubstituted or substituted 1H-pyrazol-3-yl group or an unsubstituted or substituted 2H-pyrazol-3-yl group, m is 1, and n is 0 to The oxime ether derivative or a salt thereof according to [1], which is 1.

[3] An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivative or salt thereof according to [1] or [2] (hereinafter sometimes referred to as the present invention fungicide) .)

  The compound of the present invention can be easily produced industrially, has a large control effect at a small application rate for many agricultural and horticultural crops, and has an excellent osmotic migration and residual effect, and therefore has a control effect against diseases. It is a novel compound useful as an active ingredient of an agricultural and horticultural fungicide that is reliable and can be used safely.

  The fungicide of the present invention has an excellent control effect even when the concentration of the compound of the present invention is low and the application amount is small, does not cause phytotoxicity or contamination on the plant body, and is toxic to human and livestock and has an impact on the environment. It is a drug with excellent safety.

  Such an effect of the present invention is difficult to predict from the knowledge of Patent Documents 1 to 3, and has a large control effect even at a low concentration and a small application amount. From the patent document 3, it is impossible to predict the effect that the effect of controlling the disease is certain due to the high permeability and residual effect.

(1) Oxime ether derivative or salt thereof The compound of the present invention is an oxime ether derivative represented by the formula (I) or a salt thereof.

[X]
In formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1. When n is 2 or more, Xs may be the same or different.

Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom.
The C1-8 alkyl group may be linear or branched. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, n- A heptyl group, n-octyl group, etc. are mentioned.
The C1-8 alkoxy group may be linear or branched. For example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, n-pentyloxy group, n-hexyloxy group, etc. Is mentioned.
The C1-8 haloalkyl group is not particularly limited as long as it is an alkyl group substituted with a halogen atom. For example, fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, A 2,2,2-trichloroethyl group, a pentafluoroethyl group, etc. are mentioned.
The C1-8 haloalkoxy group is not particularly limited as long as it is an alkoxy group substituted with a halogen atom. For example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, etc. Can be mentioned.
Of these, X is preferably a C1-8 alkyl group.

[R ^1, R ^2]
R ¹ and R ² each independently represents a hydrogen atom, a halogen atom, a C 1-8 alkyl group, a C 1-8 haloalkyl group, or an unsubstituted or substituted C 3-8 cycloalkyl group. m represents the number of repeating units in parentheses and is an integer of 1 to 8, preferably an integer of 1 to 3, more preferably an integer of 0 to 1. When m is 2 or more, R ¹ and R ² may be the same or different.

The halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in R ¹ and R ² are the same as those described as the halogen atom, C1-8 alkyl group, and C1-8 haloalkyl group in X. Is mentioned.
Examples of the unsubstituted C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
The substituent for the C3-8 cycloalkyl group includes a halogen atom such as a fluorine atom, a chlorine atom or a bromine atom; a C1-6 alkyl group such as a methyl group or an ethyl group; a C1-6 alkoxy group such as a methoxy group or an ethoxy group Nitro group; cyano group; and the like.
R ¹ and R ² may be bonded together to form a ring. The ring may contain a hetero atom such as an oxygen atom, a sulfur atom or a nitrogen atom. Examples of such a ring include a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, and a tetrahydropyran ring.

[R ^3]
R ³ is a hydrogen atom, a C 1-8 alkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 haloalkenyl group, a C 2-8 haloalkynyl group, or an unsubstituted or A C3-8 cycloalkyl group having a substituent is represented.

Examples of the C1-8 alkyl group, the C1-8 haloalkyl group, and the unsubstituted or substituted C3-8 cycloalkyl group represented by R ³ include the C1-8 alkyl group, C1-8, and the like in X or R ¹ above. The same thing as what was described as a haloalkyl group and a C3-8 cycloalkyl group which is unsubstituted or has a substituent is mentioned.

C2-8 alkenyl groups include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2 -Propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl Group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
Examples of the C2-8 alkynyl group include ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl Group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl -2-butynyl group and the like.
Examples of the C2-8 haloalkenyl group include 3-chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-difluoro-3-butenyl group, 3 , 3-dichloro-2-propenyl group and the like.
Examples of the C2-8 haloalkynyl group include 3-chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, and 3-iodo-2. -A propynyl group etc. are mentioned.

[R ^4]
R ⁴ is a hydrogen atom, a C 1-8 alkyl group, an unsubstituted or substituted C 3-8 cycloalkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 halo. An alkenyl group or a C2-8 haloalkynyl group is represented.

Examples of the C1-8 alkyl group in R ⁴ include the same as those described as the C1-8 alkyl group in X.
Examples of the unsubstituted or substituted C3-8 cycloalkyl group in R ⁴ include the same as those described as the unsubstituted or substituted C3-8 cycloalkyl group in R ^{1 and the} like. It is done.
In R ^4, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, and C2-8 as haloalkynyl group, in the R ^3, C2-8 alkenyl group, The same thing as what was described as a C2-8 alkynyl group, a C1-8 haloalkyl group, a C2-8 haloalkenyl group, and a C2-8 haloalkynyl group is mentioned.

[R ^5]
R ⁵ is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl. A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Examples of the C1-8 alkyl group in R ⁵ include the same as those described as the C1-8 alkyl group in X.
Examples of the acyl group include an acetyl group, a propionyl group, a pivaloyl group, a trifluoroacetyl group, a trichloroacetyl group, a benzoyl group, a 4-methylbenzoyl group, and a 2-chlorobenzoyl group.
As C1-8 alkoxy C1-8 alkyl group, methoxymethyl group, ethoxymethyl group, i-propoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 1-ethoxyethyl group, 2-ethoxyethyl group, Examples include 1-methoxy-n-propyl group, 2-methoxy-n-propyl group, 3-methoxy-n-propyl group and the like.
Examples of the C2-8 acyloxy C1-8 alkyl group include an acetoxymethyl group, an acetoxyethyl group, a propenyloxymethyl group, a pivaloyloxymethyl group, a 1-acetoxyethyl group, a 2-acetoxyethyl group, and a 1-acetoxy-n. -Propyl group etc. are mentioned.
Examples of the C1-8 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group, and the like.
Examples of the C1-8 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, and an i-propylsulfonyl group.
Examples of the unsubstituted or substituted phenylsulfonyl group include a phenylsulfonyl group, a 4-methylphenylsulfonyl group, a 2-chlorophenylsulfonyl group, and a 2,4-dimethylphenylsulfonyl group.

In the present invention, it is preferable that R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom or a C1-8 alkyl group.

[Y, Z]
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR ⁶ .
R ⁶ represents a hydrogen atom or a C1~8 alkyl group. Examples of the C1-8 alkyl group for R ⁶ include the same as those described as the C1-8 alkyl group for X.
In the present invention, Y and Z are preferably oxygen atoms.

[Q]
Q represents an unsubstituted or substituted pyrazole ring group. The bonding position of the pyrazole ring group and the carbon having R ¹ and R ² is not particularly limited. Q is preferably an unsubstituted or substituted 1H-pyrazol-3-yl group or an unsubstituted or substituted 2H-pyrazol-3-yl group.

  Examples of the substituent of the pyrazole ring group include halogen atoms such as fluorine atom, chlorine atom, bromine atom; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i -C1-6 alkyl groups such as butyl group and t-butyl group; methoxy group, ethoxy group, propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like A C1-6 alkoxy group such as a chloromethoxy group and a trifluoromethoxy group; a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, C1-6 alkylthio groups such as s-butylthio group and t-butylthio group; methylsulfonyl group, ethylsulfonyl group, i-propylsulfonyl group, n-butyl group A C1-6 alkylsulfonyl group such as a rusulfonyl group; a C1-6 haloalkyl group such as a chloromethyl group, a fluoromethyl group, a trifluoromethyl group; a methylsulfonyloxy group, an ethylsulfonyloxy group, an i-propylsulfonyloxy group, n -C1-6 alkylsulfonyloxy groups such as butylsulfonyloxy group; and the like.

Among the compounds of the present invention, particularly preferred compounds are those in which, in the oxime ether derivative represented by the formula (I) or a salt thereof, X is a C1-8 alkyl group, R ¹ , R ² , R ³ , R ⁴ and R ⁵ is each independently a hydrogen atom or a C 1-8 alkyl group, Y and Z are oxygen atoms, Q is unsubstituted or substituted 1H-pyrazol-3-yl group or unsubstituted or substituted 2H-pyrazol-3-yl group having a group, m is 1 and n is 0 to 1.

  In the oxime ether derivative of the present invention, geometric isomers based on carbon-nitrogen double bonds (cis-trans isomers) may exist, and all of these isomers are included in the present invention.

  The salt of the oxime ether derivative that is the compound of the present invention is not particularly limited as long as it is a chemically acceptable salt. For example, salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; salts of transition metals such as iron and copper; organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine And the like.

  The compound of the present invention has an excellent bactericidal activity against a wide variety of fungi, for example, bacteria belonging to algae fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes) Therefore, it is useful as an active ingredient of agricultural and horticultural fungicides.

  The compound of the present invention can be easily produced industrially in accordance with a known method, for example, the method described in Patent Document 3. The structure of the produced compound can be identified and confirmed by known analytical means such as IR spectrum, NMR spectrum, mass spectrum, and elemental analysis.

(2) Agricultural and horticultural fungicide The fungicide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.

  The fungicides of the present invention, like the compounds of the present invention, are a wide variety of fungi, for example, fungi belonging to algae (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), and basidiomycetes Excellent sterilizing power.

  The disinfectant of the present invention can be used by using means such as seed treatment, foliage application, soil application or water surface application for the control of various diseases that occur during cultivation of agricultural and horticultural crops including flowers, turf and grass. it can.

  For example, “sugar beet” brown spot (Cercospora beticola); “peanut” brown spot (Mycosphaerella arachidis); black astringency (Mycosphaerella berkeleyi); “cucumber” powdery mildew (Sphaerotheca fuliginea), vine blight ( Mycosphaerella melonis), mycorrhizal disease (Sclerotinia sclerotiorum), gray mold disease (Botrytis cinerea), black spot disease (Cladosporium cucumerinum), brown spot disease (Corynespora cassicola), seedling blight (Pythium debaryanam, Rhizoctonia solani) Disease (Pseudomonas syringae pv.Lecrymans); “Tomato” gray mold (Botrytis cinerea), leaf mold (Cladosporium fulvum); “Nasal” gray mold (Botrytis cinerea), black blight (Corynespora melongenae), powdery mildew Erysiphe cichoracearum, Mycovellosiella nattrassii; “Strawberry” gray mold (Botrytis cinerea), powdery mildew (Sohaerotheca humuli), anthracnose (Colletotrichum) acutatum, Colletotrichum fragariae); gray rot (Botrytis allii), gray mold (Botrytis cinerea), white leaf blight (Botrytis squamosa); cabbage root-knot (Plasmodiophora brassicae), soft rot ( Erwinia carotovora); “ring bean” sclerotia (Sclerotinia sclerotiorum), gray mold (Botrytis cinerea); “apple” powdery mildew (Podosphaera leucotricha), black scab (Venturia inaequalis), monilinia mali (Monilinia mali), Rot (Valsa mali), spotted leaf (Alternaria mali), red star (Gymnosporangium yamadae), ring rot (Botryosphaeria berengeriana), anthracnose (Colletotrichum gloeosprioides), brown spot (Diplocarpon mali); Powdery mildew (Phyllactinia kakicola), anthracnose (Gloeosporium kaki), keratophylla (Cercospora kaki); Gray mold disease (Botrytis cinerea), powdery mildew (Uncinula necator), late rot (Glomerella cingulata); “pear” black rot (Venturia nashicola), red rot (Gymnosporangium asiaticum), black spot (Alternaria kikuchiana); “Cha” ring spot disease (Pestalotia theae), anthracnose (Colletotrichum theae-sinensis); “citrus” scab (Elsinoe fawcetti), blue mold (Penicillium italicum), green mold (Penicillium digitatum), gray Mold disease (Botrytis cinerea), sunspot disease (Diaporthe citri), scab (Xanthomonas campestris pv.Citri); “wheat” powdery mildew (Erysiphe graminis f.sp.tritici), red mold disease (Gibberella zeae), red rust Disease (Puccinia recondita), brown snow rot (Pythium iwayamai), red snow rot (Monographella nivalis), eye spot disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), snow rot Small bacteria Nuclear disease (Typhula incarnata), Snow rot, Mycosclerotinia borealis, Gaeumanomyces graminis; “Barley” leafy disease (Pyrenophora graminea), cloud disease (Rhynchosporium secalis), naked smut (Ustilago) tritici, U.nuda); rice blast (Pyricularia oryzae), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), sesame leaf blight (Cochliobolus niyabeanus); (Sclerotinia sclerotiorum), powdery mildew (Erysiphe cichoracearum); “Tulip” gray mold (Botrytis cinerea); “Bentgrass” snow rot (Sclerotinia borealis); “Orchardgrass” powdery mildew (Erysiphe) “Soybean” purpura (Cercospora kikuchii); “Potato tomato” plague (Phytophthora infestans); “Cucumber” downy mildew (Pseudoperonospora cubensis); Doe "of downy mildew (Plasmopara viticola) etc., can be used flowers, grass, for controlling the various diseases that occur in cultivation of agricultural and horticultural crops including grass.

  In addition, the bactericidal agent of the present invention has an excellent bactericidal effect against bacteria that have become resistant to conventional bactericides such as benzimidazole bactericides and dicarboximide bactericides. Such resistant bacteria include botimidazolis cinerea, Cercospora beticola, Venturia inaequalis, and pear black star that are resistant to benzimidazole fungicides such as thiophanate methyl, benomyl, and carbendazim. Examples include Venturia nashicola; Botrytis cinerea, which is resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).

  Diseases to which the fungicide of the present invention is preferably applied include sugar beet brown spot, wheat powdery mildew, rice blast, apple black spot, cucumber gray mold, peanut brown spot, and the like. The fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.

  The fungicide of the present invention is used in a form that can be taken by general agricultural chemicals, that is, in the form of agrochemical preparations such as wettable powder, granules, powders, emulsions, aqueous solvents, suspensions, and granular wettable powders. May be.

  Additives and carriers used for solid preparations include vegetable powders such as soybean flour and wheat flour, mineral fine powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophyllite and clay, benzoic acid Organic and inorganic compounds such as soda, urea and mirabilite can be mentioned.

  Solvents used for liquid formulations include kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water etc. are mentioned.

In these preparations, a surfactant can be added as necessary in order to take a uniform and stable form.
The surfactant that can be added is not particularly limited. For example, alkylphenyl ether added with polyoxyethylene, alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol Examples include ester salts, alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.

  The wettable powder, emulsion, flowable powder, aqueous solvent and granular wettable powder thus obtained are diluted with water to a predetermined concentration and sprayed on plants in the form of a solution, suspension or emulsion. Used in the way. Powders and granules are used as they are sprayed on plants.

  The amount of the active ingredient in the fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the whole preparation.

  The application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application magnetism, application method, application place, disease to be controlled, target crop, etc., but usually 1 to 1,000 g as an active ingredient compound amount per hectare. , Preferably 10 to 100 g.

  When a wettable powder, emulsion, suspension, aqueous solvent, granular wettable powder or the like is diluted with water and applied, the applied concentration is 1-1000 ppm, preferably 10-250 ppm.

  In addition to the compounds of the present invention, other fungicides, insecticides / miticides, synergists and the like can also be mixed with the fungicides of the present invention.

  Typical examples of other fungicides, insecticides, acaricides, and plant growth regulators that can be used in combination are shown below.

Fungicide:
Captan, phorpet, thiuram, ziram, dinebu, manneb, mancozeb, propineb, polycarbamate, chlorothalonil, quintozen, captaphor, iprodione, prosaimidin, vinclozolin, fluoroimide, thymoxanyl, mepronil, flutolanil, pencyclon, oxycarboxyl, fosetyl aluminum, Propamocurve, triadimephone, triadimenol, propiconazole, diclobutrazole, viteltanol, hexaconazole, microbutanyl, flusilazole, metconazole, etaconazole, fluotrimazole, cyproconazole, epoxyconazole, flutriaphene, beconazole , Diniconazole, cyproconazole, phenalimol, triflumizole, prochlor , Imazalyl, pefrazoate, tridemorph, fenpropimorph, triphorin, butiobate, pyrifenox, anilazine, polyoxin, metalaxyl, oxadixyl, furaxyl, isoprothiolane, probenazole, pyrrolnitrin, blasticidin S, kasugamycin, validamycin, dihydrostreptomycin sulfate , Benomyl, carbendazim, thiophanatemethyl, hymexazole, basic copper chloride, basic copper sulfate, fentin acetate, triphenyltin hydroxide, dietofencarb, metasulfocarb, quinomethionate, binapacryl, lecithin, baking soda, dithianone, dinocup, phenaminosulfur, Dichromemedin, Guazatine, Dodin, IBP, Edifenphos, Mepanipyrim, Fermzo , Trichlamide, methasulfocarb, fluazinam, Etokinorakku, dimethomorph, pyroquilon, tecloftalam, fthalide, phenazine oxide, thiabendazole, tricyclazole, vinclozolin, cymoxanil, cyclobutanyl, guazatine, propamocarb hydrochloride, oxolinic acid, hydroxy isoxazole, iminoctadine acetate, and the like.

Insecticides and acaricides:
Organophosphorus and carbamate insecticides:
Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbosulfan, Benhracarb, Furatiocarb Propoxur, BPMC, M MC, MIPC, carbaryl, pirimicarb, ethiofencarb, fenoxycarb, EDDP, and the like.

Pyrethroid insecticides:
Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.

Benzoylurea and other insecticides:
Diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, metoprene, benzoepin, diafenthiuron, acetamiprid, imidacloprid, nitenpyram, fipronil, cartap Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.

Nematicides:
Phenamifos, phostiazates, etc.

Acaricide:
Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.

Plant growth regulator:
Gibberellins (eg, gibberellin A3, gibberellin A4, gibberellin A7), IAA, NAA and the like.

  Next, an Example is shown and this invention is demonstrated concretely. However, the present invention is not limited to the following examples.

  The compound of the present invention was produced according to the method described in Patent Document 3. Table 1 shows the NMR data and Table 2 shows the melting point (° C.) or refractive index of a part of the produced compound of the present invention.

  Next, formulation examples of the fungicide of the present invention are shown below. However, additives and addition ratios are not limited to these formulation examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.

Formulation Example 1 Wetting agent Oxime ether derivative compound of the present invention 40 parts Clay 48 parts Dioctyl sulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more uniformly mixed and finely pulverized, active ingredient 40% Get a wettable powder.

Formulation Example 2 Emulsion Oxime ether derivative compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkyl allyl ether 10 parts Mixing and dissolving the above, an emulsion containing 10% active ingredient obtain.

Formulation Example 3 Powder A oxime ether derivative compound of the present invention 10 parts Clay 90 parts The above is uniformly mixed and finely pulverized to obtain a powder of 10% active ingredient.

Formulation Example 4 Granule Oxime ether derivative compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part After the above is well ground and mixed, water is added and kneaded well Granulation and drying to obtain granules with 5% active ingredient.

Formulation Example 5 Suspension agent Oxime ether derivative compound of the present invention 10 parts Polyoxyethylene alkylallyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts Is pulverized wet until it becomes 3 microns or less to obtain a suspension with 10% active ingredient.

Formulation Example 6 Granule wettable powder Oxime ether derivative compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Ligninsulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt
Mix 5 parts or more uniformly and pulverize finely, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a wettable powder containing 40% of the active ingredient.

A test for confirming the activity of the fungicide of the present invention was performed as follows.
The control effect was calculated as a control value from the following Abbot formula.
Control value (%) = (1−α / β) × 100
α corresponds to the amount of fungal infection in the treated plant,
β corresponds to the amount of fungal infection in untreated (control) plants.
A control value of 0% means that the level of infection of the treated plants is consistent with that of the untreated control plants, and an effect of 100% means that the treated plants were not infected at all.

(Test Example 1) Apple scab control test The emulsion produced according to the formulation of Formulation Example 2 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on apple seedlings (variety “Kokumi”, 3-4 leaf stage) grown in an unglazed pot. Next, it was naturally dried at room temperature. Conidia spores of Venturia inaequalis were inoculated and kept in a room at 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
The apple scab control test was conducted for the oxime ether derivative compounds of Compound Nos. 1, 2, 3, 4, 5, 6, 7, 9, and 10 in Table 1. As a result, all the compounds showed an excellent control value of 75% or more.

(Test Example 2) Wheat powdery mildew control test A wettable powder prepared according to the formulation of Preparation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings grown in an unglazed pot (variety “Chihoku”, 1.0-1.2 leaf stage). The leaves were then air dried. The conidia of wheat powdery mildew (Erysiphe graminis f.sp.tritici) were shaken off and inoculated in a 22-25 ° C. greenhouse for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
A wheat powdery mildew control test was conducted for the oxime ether derivative compounds of Compound Nos. 1, 3, 4, 5, and 7 in Table 1. As a result, all the compounds showed an excellent control value of 75% or more.

(Test Example 3) Wheat red rust control test A wettable powder produced according to the formulation of Preparation Example 1 was diluted with water to adjust the active ingredient concentration to 100 ppm. The diluent was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0-1.2 leaf stage). The leaves were then air dried. The summer spores of wheat rust (Puccinia recondita) were shaken off and inoculated in a greenhouse at 22-25 ° C. for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was examined.
A wheat red rust control test was conducted on the oxime ether derivative compounds Nos. 1, 3, 4, 5, 7, 8, 9, and 10 in Table 1. As a result, all the compounds showed an excellent control value of 75% or more.

Claims (3)

An oxime ether derivative represented by the formula (I) or a salt thereof.

[In formula (I), X represents a halogen atom, a C1-8 alkyl group, a C1-8 alkoxy group, a C1-8 haloalkyl group, or a C1-8 haloalkoxy group. n represents the number of substitutions of X and is an integer of 0 to 4. When n is 2 or more, Xs may be the same or different.
R ¹ and R ² each independently represents a hydrogen atom, a halogen atom, a C 1-8 alkyl group, a C 1-8 haloalkyl group, or an unsubstituted or substituted C 3-8 cycloalkyl group. R ¹ and R ² may be bonded together to form a ring. m represents the number of repeating units in parentheses and is an integer of 1-8. When m is 2 or more, R ¹ and R ² may be the same or different.
R ³ is a hydrogen atom, a C 1-8 alkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 haloalkenyl group, a C 2-8 haloalkynyl group, or an unsubstituted or A C3-8 cycloalkyl group having a substituent is represented.
R ⁴ is a hydrogen atom, a C 1-8 alkyl group, an unsubstituted or substituted C 3-8 cycloalkyl group, a C 2-8 alkenyl group, a C 2-8 alkynyl group, a C 1-8 haloalkyl group, a C 2-8 halo. An alkenyl group or a C2-8 haloalkynyl group is represented.
R ⁵ is a hydrogen atom, C1-8 alkyl group, acyl group, formyl group, C1-8 alkoxy C1-8 alkyl group, C2-8 acyloxy C1-8 alkyl group, C1-8 alkoxycarbonyl group, C1-8 alkyl. A sulfonyl group or an unsubstituted or substituted phenylsulfonyl group is represented.
Y represents an oxygen atom or a sulfur atom.
Z represents a single bond, an oxygen atom, a sulfur atom, or a group represented by NR ⁶ . R ⁶ represents a hydrogen atom or a C1-8 alkyl group.
Q represents an unsubstituted or substituted pyrazole ring group. ] X is a C1-8 alkyl group, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom or a C1-8 alkyl group, Y and Z are oxygen atoms, and Q is An unsubstituted or substituted 1H-pyrazol-3-yl group or an unsubstituted or substituted 2H-pyrazol-3-yl group, m is 1 and n is 0 to 1 The oxime ether derivative or a salt thereof according to claim 1.   An agricultural and horticultural fungicide containing as an active ingredient at least one selected from the oxime ether derivatives or salts thereof according to claim 1 or 2.