JP2018012646A - Hydrazone derivative and pest control agent - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel bactericide, particularly a bactericide for agricultural and horticultural use.SOLUTION: The present invention provides a hydrazone derivative represented by formula (I) [where W is an oxygen atom and the like, A is an oxygen atom and the like, Ris C-Calkyl, C-Calkoxy and the like, Ris a hydrogen atom, C-Calkyl and the like, Ris a hydrogen atom, C-Calkyl and the like, Rand Rindependently represent a hydrogen atom and the like, R, R, Rand Rindependently represent a hydrogen atom, a halogen atom and the like, Ris C-Calkyl and the like] or a salt thereof, and a bactericide for agricultural and horticultural use containing them.SELECTED DRAWING: None

Description

  The present invention relates to a novel hydrazone derivative and a salt thereof, and a pest control agent containing the compound as an active ingredient.

  It is known that certain hydrazone derivatives have bactericidal activity (see, for example, Patent Document 1).

  Moreover, it is known that the compound which has a certain kind of heterocyclic ring, for example, a tetrazolinone ring, has bactericidal activity (for example, refer patent document 2-patent document 3).

  However, no hydrazone derivatives according to the present invention are disclosed, and their usefulness as pest control agents is not known.

JP-A-8-225515 International Publication No. 1996/036229 International Publication No. 2013/162072

  The development of control agents for diseases of agricultural and horticultural crops has progressed, and a wide variety of drugs have been put to practical use until now. However, due to the long-term use of such drugs, in recent years, pathogens have acquired drug resistance, and the number of scenes where it is difficult to control with existing bactericides that have been used in the past has increased. In addition, some existing drugs are highly toxic, or some remain in the environment for a long time, causing problems that disturb the ecosystem. Under such circumstances, development of a new drug having not only high control activity and high safety for target crops but also low toxicity and low persistence is always expected.

  As a result of intensive research aimed at solving the above problems, the present inventors have found that the novel hydrazone derivative represented by the following formula (I) according to the present invention is excellent as a fungicide, particularly an agricultural and horticultural fungicide. The present invention has been found to be a very useful compound having a control activity and a high safety against the target crop, and having almost no adverse effect on non-target organisms such as mammals, fish and beneficial insects. completed.

  That is, the present invention relates to the following [1] to [5].

[1]
Formula (I):

[Wherein W represents an oxygen atom or a sulfur atom,
A represents an oxygen atom or a sulfur atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, (C ₁ -C ₆ ) alkenyl optionally substituted by R ^a , C ₁ -C ₆ alkoxy, phenyl, (Z) _m substituted phenyl, pyridin-2-yl, _(Z) is replaced by _n pyridine-2-yl, pyridin-3-yl, _(Z) pyridine substituted by _n-3-yl, pyridin-4-yl , _(Z) is replaced by _n pyridine-4-yl, thiophen-2-yl, _(Z) is replaced by _p thiophene-2-yl, thiophen-3-yl, thiophene substituted by _{(Z) p} 3-yl, thiazol-2-yl, _(Z) is replaced by _r thiazol-2-yl, thiazol-4-yl, _(Z) thiazol-4-y substituted by _r , Thiazol-5-yl, _(Z) is replaced by _r thiazol-5-yl, naphthalen-1-yl, _(Z) is replaced by _q the naphthalene-1-yl, naphthalene-2-yl or (Z) represents naphthalen-2-yl substituted by _q ,
R ² is a hydrogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C ₆₎ ^alkyl, optionally substituted by ^{R b1} _(C 1 ~C _{6) alkyl,} C 1 -C ₆ alkoxy, _{C 1} -C _{6 alkylcarbonyl,} C 1 -C ₆ alkoxycarbonyl or phenyl,
R ³ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ cycloalkyl, halo _(C 1 ~C ₆₎ alkyl, optionally substituted by ^{R b} _(C 1 ~C ₆₎ alkyl, halo _(C 1 _{~C 6)} cycloalkyl, optionally substituted by ^{R b} _(C 1 ~C _{6) cycloalkyl,} C 1 -C _{6 alkenyl,} C 1 -C _{6 alkynyl,} C 1 -C ₆ alkoxycarbonyl, Represents phenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, oxetan-2-yl or tetrahydrofuran-2-yl;
R ⁴ and R ⁵ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, halogen atom, nitro, cyano, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkenyl. C ₁ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl or C ₁ -C ₆ alkylsulfonyl,
R ¹⁰ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Z is a halogen atom, nitro, cyano, carboxy, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, halo (C ₁ -C ₆ ) alkoxy, C ₁ -C _{6 alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C _{6 alkylcarbonyl,} C 1 -C _{6 alkoxycarbonyl,} C 1 -C _{6 alkylaminocarbonyl,} C 1 -C ₆ alkoxy _(C 1 ~C ₆₎ alkyl, -C (= ^NOR c) represents ^{R d} or phenyl,
m represents an integer of 2, 3, 4 or 5, n represents an integer of 2, 3 or 4, p represents an integer of 2 or 3, q is 2, 3, 4, 5, 6 Or when r represents an integer of 7 or r represents an integer of 2, each Z may be the same as or different from each other;
R ^a represents phenyl or phenyl substituted by (Z) _m ,
R ^b is hydroxy, C ₁ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylcarbonyloxy or (Z) _m Represents substituted phenyl,
R ^b1 is hydroxy, C ₁ -C ₆ cycloalkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C Represents phenyl substituted by ₆ alkylcarbonyloxy or (Z) _m ;
R ^c and R ^d each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
p represents an integer of 1, 2 or 3,
q represents an integer of 1, 2, 3, 4, 5, 6 or 7,
r represents an integer of 1 or 2,
m represents an integer of 1, 2, 3, 4 or 5;
n represents an integer of 1, 2, 3, or 4].

[2]
W represents an oxygen atom,
A represents an oxygen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, (C ₁ -C ₆ ) alkenyl optionally substituted by R ^a , phenyl, (Z) _m substituted phenyl, pyridine- 2-yl, (Z) _n- substituted pyridin-2-yl, pyridin-3-yl, (Z) _n- substituted pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, (Z) represents thiophen-2-yl, thiophen-3-yl, thiazol-2-yl, substituted by _p , (Z) thiazol-2-yl or naphthalen-2-yl substituted by _r ;
R ² represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl or phenyl optionally substituted by R ^b1 ,
R ³ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ cycloalkyl, halo _(C 1 ~C ₆₎ alkyl, optionally substituted by ^{R b} _(C 1 ~C ₆₎ alkyl, halo _(C 1 _{~C 6)} cycloalkyl, _C 1 -C ₆ cycloalkyl optionally substituted by ^{R _b,} C 1 _{~C 6} alkoxycarbonyl, phenyl, pyridin-2-yl, pyridin-3-yl or pyridine - Represents 4-yl,
R ⁴ and R ⁵ represent a hydrogen atom,
R ⁶ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl or C ₁ -C ₆ alkylthio,
R ⁷ represents a hydrogen atom or a halogen atom,
R ⁸ and R ⁹ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
R ¹⁰ represents C ₁ -C ₆ alkyl,
Z is a halogen atom, nitro, cyano, carboxy, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, halo (C ₁ -C ₆ ) alkoxy, C ₁ -C ₆ represents _alkylthio, C 1 -C _{6 alkylcarbonyl,} C 1 -C _{6 alkoxycarbonyl,} C 1 -C ₆ alkylaminocarbonyl, -C a (= ^NOR c) ^{R d} or phenyl,
R ^a represents phenyl substituted by (Z) _m ,
R ^b is hydroxy, C ₁ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylcarbonyloxy or (Z) _m Represents substituted phenyl,
R ^b1 represents C ₁ -C ₆ alkoxy;
R ^c and R ^d independently of one another represent C ₁ -C ₆ alkyl,
The hydrazone derivative or a salt thereof according to the above [1].

[3]
An agrochemical containing one or more selected from the hydrazone derivatives according to the above [1] to [2] and salts thereof as an active ingredient.

[4]
A fungicide containing as an active ingredient one or more selected from the hydrazone derivatives described in [1] to [2] above and salts thereof.

[5]
An agricultural and horticultural fungicide containing, as an active ingredient, one or more selected from the hydrazone derivatives described in the above [1] to [2] and salts thereof.

  The compound of the present invention has an excellent control activity against many pathogenic bacteria, and also exhibits a sufficient control effect against pathogenic bacteria that have acquired resistance to existing fungicides. Furthermore, it does not cause phytotoxicity on the target crop, has almost no adverse effect on mammals, fish and beneficial insects, has low persistence, and has a low environmental impact.

  Therefore, the present invention can provide useful fungicides, particularly agricultural and horticultural fungicides.

  The compounds included in the present invention may have geometrical isomers of E-form and Z-form depending on the type of substituent, and the present invention is not limited to these E-form, Z-form or E-form. And a mixture containing the Z-form in an arbitrary ratio. In addition, the compounds included in the present invention may exist as one or more rotational isomers due to limited bond rotation caused by steric hindrance between substituents, but all of the present invention Or a mixture of diastereomers including any proportions. In addition, the compounds included in the present invention include optically active substances resulting from the presence of one or more asymmetric carbon atoms, but the present invention includes all optically active substances or racemates.

  Among the compounds included in the present invention, those that can be converted into acid addition salts according to a conventional method include, for example, hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, and the like. Salts of inorganic acids such as salts, nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, Salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, succinic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid or the like A salt of an amino acid such as glutamic acid or aspartic acid can be used.

  Alternatively, among the compounds included in the present invention, those that can be converted into a metal salt according to a conventional method include, for example, alkali metal salts such as lithium, sodium, and potassium, and alkaline earth metals such as calcium, barium, and magnesium. It can be a salt or a salt of aluminum.

  Next, specific examples of each substituent shown in the present specification are shown below. Here, n- represents normal, i- represents iso, s- represents secondary, and tert- represents tertiary, and Ph represents phenyl.

  As a halogen atom in this invention compound, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned. In the present specification, the notation “halo” also represents these halogen atoms.

The notation of C _a -C _b alkyl in the present specification represents a linear or branched hydrocarbon group having a carbon number of _a to _b , for example, methyl group, ethyl group, n-propyl group, Specific examples include i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, and the like. Each selected range of carbon atoms is selected.

In the present specification, the notation of halo (C _a -C _b ) alkyl is a straight or branched chain consisting of _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom A chain-like hydrocarbon group is represented, and when substituted by two or more halogen atoms, these halogen atoms may be the same as or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2- Chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1 , 1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3 , 3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group, 1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl group, 2,2,3,3,4, Specific examples include 4,4-heptafluorobutyl group, nonafluorobutyl group and the like, and each is selected within the range of the number of carbon atoms designated.

In the present specification, C _a -C _b cycloalkyl represents a cyclic hydrocarbon group having a carbon number of _a to _b and forms a monocyclic or complex ring structure from 3 to 10 membered rings. I can do it. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms. Specific examples include, for example, cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. Selected in a range of numbers.

The notation of C _a -C _b halocycloalkyl in the present specification represents a cyclic hydrocarbon group having _a to _b carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with a halogen atom. A monocyclic or complex ring structure from a 3-membered ring to a 10-membered ring can be formed. Each ring may be optionally substituted with an alkyl group within the range of the specified number of carbon atoms, and the substitution with a halogen atom may be a ring structure part, a side chain part, They may be both, and when they are substituted by two or more halogen atoms, the halogen atoms may be the same as or different from each other. For example, 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methyl Cyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, 1-trifluoromethylcyclopropyl group, 2-trifluoromethylcyclopropyl group, 1-trichloromethylcyclopropyl group, 2-trichloromethylcyclopropyl group Specific examples include a 2,2,3,3-tetrafluorocyclobutyl group and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkenyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more double bonds in the molecule. Represents a saturated hydrocarbon group, for example, vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 1 , 1-dimethyl-2-propenyl group and the like are listed as specific examples, and each is selected within the range of the designated number of carbon atoms.

In the present specification, C _a -C _b alkynyl is a linear or branched chain composed of _a to _b carbon atoms and has one or more triple bonds in the molecule. Represents a hydrocarbon group, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1,1-dimethyl-2-propynyl group, etc. Each of which is selected for each specified number of carbon atoms.

The notation of C _a -C _b alkoxy in the present specification represents an alkyl-O— group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxy group, ethoxy group, n-propyloxy group, Specific examples include an i-propyloxy group, an n-butyloxy group, an i-butyloxy group, an s-butyloxy group, a tert-butyloxy group, and the like, and each is selected within the range of the designated number of carbon atoms.

In the present specification, the notation of halo (C _a -C _b ) alkoxy represents a haloalkyl-O-group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as a difluoromethoxy group, a trifluoromethoxy group, Chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2-chloro- Specific examples include a 1,1,2-trifluoroethoxy group, a 1,1,2,3,3,3-hexafluoropropyloxy group, and the like are selected in the range of the designated number of carbon atoms.

The notation of C _a -C _b alkylthio in the present specification represents an alkyl-S-group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylthio group, ethylthio group, n-propylthio group, i Specific examples include -propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group and the like, which are selected within the range of the number of carbon atoms specified.

The notation of C _a -C _b alkylsulfinyl in the present specification represents an alkyl-S (O) -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfinyl group, ethylsulfinyl group, Specific examples include n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group and the like. The range is selected.

The notation of C _a -C _b alkylsulfonyl in the present specification represents an alkyl-S (O) ₂ -group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group , N-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group, etc. Selected in a range of numbers.

In the present specification, the expression “C _a -C _b alkylcarbonyl” represents an alkyl-C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, such as an acetyl group, a propionyl group, Specific examples include butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, and the like, and each is selected within the range of the designated number of carbon atoms.

The notation of C _a -C _b alkoxycarbonyl in the present specification represents an alkyl-O—C (O) — group having the above-mentioned meaning consisting of _a to _b carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl Group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, tert-butoxycarbonyl group and the like, and specific ranges of the number of carbon atoms are designated. Selected.

The notation of C _a -C _b alkoxy (C _d -C _e ) alkyl in the present specification indicates that a hydrogen atom bonded to a carbon atom is optionally substituted by any C _a -C _b alkoxy group having the above-mentioned meaning, respectively. Represents an alkyl group having the above-mentioned meaning consisting of de to e carbon atoms, and is selected in the range of each designated number of carbon atoms.

Designation "optionally substituted by R ^a _(C ^a ~C _b) alkenyl" in the present specification, by any R ^a, carbon atoms bonded to hydrogen atoms are optionally replaced by a carbon atom a Represents an alkenyl group having the aforementioned meaning consisting of ˜b, and is selected in the range of the respective designated number of carbon atoms. At this time, when two or more substituents R ^a on each (C _a -C _b ) alkenyl group are present, each R ^a may be the same as or different from each other.

In the present specification, the notation “(C _a -C _b ) alkyl optionally substituted with R ^b ” indicates that the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R ^b is a Represents an alkyl group as defined above consisting of ˜b, and is selected within the range of the respective number of carbon atoms specified. At this time, when two or more substituents R ^b on each (C _a -C _b ) alkyl group are present, each R ^b may be the same as or different from each other.

In the present specification, the notation “(C _a -C _b ) cycloalkyl optionally substituted with R ^b ” refers to the number of carbon atoms in which a hydrogen atom bonded to a carbon atom is optionally substituted with any R ^b . It represents a cycloalkyl group having the above-mentioned meanings consisting of a to b, and is selected in the range of each designated number of carbon atoms. At this time, when two or more substituents ^Rb on each (C _a -C _b ) cycloalkyl group are present, each R ^b may be the same as or different from each other.

  Examples of the pesticidally acceptable salt of the hydrazone derivative of the present invention include hydrochloride, hydrobromide, hydroiodide, formate, acetate or oxalate.

  The compounds of the present invention are generally used as fungicides and fungicides for agricultural and horticultural use in various diseases caused by root-knot fungi, oomycetes, zygomycetes, ascomycetes, basidiomycetes, imperfect fungi, bacteria or viruses. Can be used against.

As plant diseases to be controlled by the compounds of the present invention,
Rice blast (Piculararia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), rice mildew (Claviceps virenk), leaf seedling (Gibberk) P. spinosum, Fusar
Ium avenaceum, Fusarium solani, Fusarium spp. Rhizopus chinensis, R. oryzae, Rhizopus spp. , Trichoderma viride), Burkholderia glumae, Seedling bacterial disease (Burkholderia plantaii), Brown stripe disease (Acidovorax avene), White leaf blight (Xorwoniae in Echinacea)
Wheat stripe atrophy, Barley yellow mosaic virus, wheat powdery mildew (Erysiphe graminis f. Sp. Hordei, E. f. (Pyrenophora graminea), reticular rot (Pyrenophora teres), red mold (Gibberella zeae), rust (Puccinia striformis, P. graminis, P. recondita, P. yhorde) Rot (Tipula sp., Micronelliella nipivais), Bare Scab (Ustil) go tritici, U. nuda), cloud disease (Rhynchosporium secalis), leaf blight (Septoria trihortici), leaf blight (Leptospharia nodorum), small spot disease (Pseudocercosporella pallet) Snow rot large grain sclerotia (Myrioclerotinia borealis), wheat red snow rot (Monographella nivalis), withering disease (Gaeumanomyces graminis),
Citrus spot disease (Diaporthe citri), scab (Elsinoe fawcetii), fruit rot (Penicillium digitatum, P. italicum), scab (Xanthomonas campestris), gray mold (B)
Mongolia disease of Mongolia (Monilinia mali), rot (Valsa mali), powdery mildew (Podosphaera leukotricha), spotted leaf disease (Alternaria maria), scab (Venturia inaequalis)
Pear black spot disease (Venturia nashikocola), black spot disease (Alternaria kikuchiana), red star disease (Gymnosporium erbiotic asiaticum), plague (Phytophthora cergocterun, P. syringae), leaf syringae , Powdery mildew (Phyllactinia mary),
Peach ash streak (Monilinia fracticola), black streak (Cladosporium carpophilum), pomopsis rot (Phomophsis disease), pneumotrophic disease (Pseudocercospora circumscis, saury) deformans), plum scab (Pseudomonas syringae pv. morsprunorum), ash scab (Monilinia fracticola), black spot (Xanthomonas campestri pv. punil disease).
Pseudomonas syringae pv. Morsprunorum, black scab (Cladosporium carpophilum),
Grape downy mildew (Plasmopara viticola), black scab (Elsinoe ampelina), late rot (Glomerella gingulata), powdery mildew (Uncinula necatoris), rust (Amphidiaploid bud) Mold disease (Botrytis cinerea),
Oyster anthracnose (Glomerella orbicula), defoliation (Mycosphaerella nawai), gray mold (Botrytis cinerea), powdery mildew (Phyllactinia kakicola),
Downy mildew (Pseudoperenospora cubensis), anthracnose (Colletotrichumum orbicula), powdery mildew (Sphaerotheca fuliginea), vine blight (Didlymella brionum) , Sclerotia sclerotiorum, Fusarium solani, white silkworm (Sclerotium rolfsii), homopsis root rot (Phomopsis sclerotioides),
Cucumber brown spot (Corynespora casicicola), seedling blight (Pythium cucurbitaceacerum, P. debaryanum, Rhizoctonia solani), root rot (Pytium myriotrum, P.) Disease (Pseudomonas syringae pv. Lacrymans), purple coat rot (Helicobasidium mompa),
Brown rot of watermelon (Phytophthora capsici), plague (Phytophthora cryptogea),
Melon blight (Phythium debaryanum), plague (Phytophthora nicotianae),
Pumpkin plague (Phytophthora capsici),
Eggplant blight (Ralstonia solanacerum), wilt disease (Fusarium oxysporum), gray mold disease (Botrytis cinereaa), mycorrhizal disease (Sclerotinia sclerotiorum), white silkworm (Sclerotium olfactory)
Potato plague (Phytophthora infestans), summer plague (Alternaria solani), black scab (Thanatephorus cucumeris), black scab (Erwinia carotovora), common scab (Streptomyc spp.) Spongespora subterranea,
Phytophthora infestans, Phytophthora criptogea, Phytophathora capsici, Alternaria sulani, leaf mold disease (Fulvia uldus). , Brown rot, Phytophthora nicotianae, scab (Clavibacter michiganensis), brown root rot (Pyrenochaeta lycopersii), anthracnose (Colletotrichum gloesporis), (Verticillium dahliae), leaf spot (Stemphylium lycopersici),
Pepper plague (Phytophthora capsici), powdery mildew (Oidiopsis sicula), seedling blight (Rhizotonia solani), spot disease (Cercospora capsici),
Eggplant plague (Phytophthora infestans), brown rot (Phytophthora capsici), brown rot (Phomopsis vexans), powdery mildew (Erysiphe cichoracerum, Oidiopsis sicula)
Phytophthora sp., Downy mildew (Peronospora effusa), withering disease (Pythium aphanidermatum, P. myriotylum, P. paraecandrum, P. ultimum, sprout disease) ), Root rot (Aphanomyces cochlioides), spot disease (Heterosporia variabile),
White leaf blight of leeks (Phytophthora porori), blight (Phytophthora nicotianae), white silkworm (Sclerotium rolfsiii), seedling blight (Rhizoctonia solanii), black spot disease (Alternaria poultry disease) ), Downy mildew (Peronospora destructor), rust (Puccinia allii),
Leek wilt (Fusarium oxysporum), macular disease (Heterosporia aliii), red root rot (Pyrenochaeta terrestris), bacterium rot (Botrytis squamosa),
Onion dry rot (Fusarium oxysporum), smut (Urocystis cepulae), sclerotia nuclei (Cibolinia alli), gray mold (Botrytis cinerea), gray rot (Botrytis allirp), rot Burkholderia gladioli,
Brassicaceae vegetable downy mildew (Peronospora parasitica), root-knot disease (Plasmodiophora brassicae), white rust (Albuguoma macrospora), black spot (Alternaria japonica), A. brasco disease, A. brasic disease Erwinia carotovora), mycorrhizal disease (Sclerotinia sclerotiorum),
Strains of cabbage (Thanatephorus cucumeris), Verticillium dahliae, yellow cabbage (Verticillium dahliae), rot rot (Rhizotonia solani), gray scab Botrytis cinerea), Pythium ultimum,
Japanese radish anthracnose (Colletotrichum higginsianum), Verticillium albo-atrum,
Legume blight (Ralstonia solanacearum), wilt disease (Verticillium dahlliae), mycorrhizal disease (Sclerotinisia sclerotiorum), black root disease (Thielaviopsis sp.), Rust disease (Phakopsorapirosis) Fusarium oxysporum, Anthracnose (Colletotrichum truncatum, C. trifolii, Glomerella glycines, Gloeosporium sp.), Gray mold (Botrytis cinerea)
Soybean downy mildew (Peronospora manshurica), stem rot (Phytophthora sojae), leaf burning (Xanthomonas campestris pv. Glycines), purpura (Cercospora kikuchii), black spot (Cercospora kikuchii), black spot (Cercospora kikuchii)
Peanut black astringency (Mycosphaerella personata), brown spot (Mycosphaerella arachidis), pea powdery mildew (Erysiphe pisi),
Strawberry powdery mildew (Sphaerotheca aphanis), yellowing (Fusarium oxysporum), wilt (Verticillium dahliae), plague (Phytophthora cactrum, black spot bacterial disease (Xanthomonasca). , Potato disease (Mycosphaerella fragaliae), anthracnose (Colletotrichum acutatum, C. fragariae, Glomerella singularata), root rot (Phytophthora fragriae), gray mold disease lani), Wamadarabyo (Drenerophoma obscurans),
Lettuce sclerotia (Sclerotinia sclerotiorum), Blight blight (Rhizobacter solani), Soft rot (Erwinia carotovora), Blight (Pythium sp.), Root rot (Fusarium oxysporum), Gray rot, and gray rot Bacterial disease (Xanthomonas campestris pv. Vitians), Big vein disease (Lettuce big-vein virus), rot disease (Pseudomonas cichoris, P. marginalis pv. Virgin disease, P. marginalis pv. Virgin disease).
Burdock wilt disease (Fusarium oxysporum), black bruise (Rhizoctonia solani), black stripe disease (Itersonilia perplexans), black spot bacterial disease (Xanthomomonas camphorsis disease pv. irregulare), purple coat feather (Helicobasidium mompa),
Carrot wilt (Fusarium oxysporum), powdery mildew (Erysiphe heraclei), black leaf blight (Alternaria dauci), mildew (Rhizoctonia dauci), leaf rot (Pythium sulcium rot) Disease (Erwinia carotovora), root rot (Rhizoctonia solani), spot disease (Cercospora carrotae), purple coat (Helicobasidium mompa),
Chamochi rice blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), brown scab (Pseudocercospora ocellata, Cerospora chas), rice blast (Exobasidium pex. Disease (Colletotrichum thea-sinensis),
Tobacco Red Star Disease (Alternaria alternata), Powdery Mildew (Erysiphe cichoacearum), Anthracnose (Colletotrichum cichoacearum),
Brown beet disease of sugar beet (Cercospora beticola), black root disease (Aphanomyces cochlioides), root beetle (Beet necrous yellow sp.), Phythium bebarium, Phomae horzole physic rape,
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa),
Chrysanthemum brown spot (Septoria chrysanthemiindicii), white rust (Puccinia horiana),
Fevering disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oradees), pseudoleaf rot (Ceratobasidium spp.), Leaf disease (Gaemnomyces graminis) ), Pythium periplocum, P. graminicola, P. vanterpoulii, Rust (Puccinia spp.), Powdery mildew (Erysiphegramyis DC), Dollar spot disease (Sclerotinoposis) . pp., Typhula incarnata, T. isikariensis, Fusarium nivale, Sclerotinia borealis),
Bentgrass red blight (Pythium aphanidermatum), anthracnose (Colletotrichum sp.) And the like can be mentioned, but the present invention is not limited thereto.

  In addition to use as agricultural and horticultural fungicides, the compounds of the present invention are antibacterial and antifungal agents such as medical antibacterial agents, animal antibacterial agents, wood, paper / pulp, adhesives / paints, fibers, leather, etc. It can also be used as an industrial disinfectant such as a cooling water channel in a manufacturing plant.

The antimicrobial agent for medical use of the compound of the present invention, the pathogenic bacteria that are targeted as animal antimicrobial agents,
Trichophyton rubrum, Trichophyton mentagrophytes, etc. Ringworm fungi, Candida albicans, Candida fungi, Aspergillus fumigatus fungi, E. coli, etc. Gram-negative bacteria such as Haemophilus influenzae, Gram-positive bacteria such as Staphylococcus aureus, Streptococcus pyogenes, and the like. It is not limited to only.

In addition, as strains targeted as antibacterial and antifungal agents for wood, paper / pulp, adhesives / paints, fibers, leather, etc.
Tyromyces palustris, wood-rotting fungi such as Coriolus versicolor, Aspergillus niger, Aspergillus terreus, Eurotium tonophilum, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, Cladosporium cladosporioides, Aureobasidium pullulans, Gliocladium virens, Chaetomium globosum, Fusarium moniliforme, of materials such as Myrothecium verrucaria Examples include degraded microorganisms.

Examples of strains that are targeted as industrial fungicides include slime fungi such as Sphaerotilis natans and Zoogloea ramigera, but the present invention is not limited thereto.

  The compound of the present invention can be used not only as an agricultural and horticultural fungicide but also as an endoparasite control agent for livestock, poultry, pets and the like.

The endoparasite which is a target of the present invention compound as an endoparasite control agent,
Haemonchus, Trichostrongillus, Ostertagia, Nematodirus, Cooperia, Ascarisum, Bnost Genus (Oesophagostoumum), Chabertia (Chabertia), Trichuris (Trichuris), Strongylus (Storongylus), Trichonema (Trichonema), Dictiocaurus (Dictyocaurus), Capriella i ), Toxocara , Asuka Lydia genus (Ascaridia), Okishiurisu genus (Oxyuris), Anne kilometers stoma genus (Ancylostoma), Unshinaria genus (Uncinaria), Tokisasukarisu genus (Toxascaris), nematodes such as Parasukarisu genus (Parascaris),
Filariidae nematodes such as Wuchereria, Brugia, Onchocerca, Dirofilaria, Loa, and the like,
Dracunculus nematodes such as the genus Deacunculus,
Dogpyridium (Dipyridium caninum), caterpillar (Taenia taeniaeformis), potato tapeworm (Taenia solium), scabies tapeworm (Taenia saginata), tapeworm (Hymenolepis diminta), Beneden edenedia C. elegans (Diphyllobothrium latum), C. elegans (Diphyllobothrium erinacei), Echinococcus granulosus, Echinococcus multiloculus, etc.
Fasciola hepatica (F. gigantica), Westermann pulmonary fluke (Paragonimus westermanii), hypertrophic fluke (Fasciolopsic brilliant), C. pulmonary fluke (E.) japonicum), Schistosoma haematobium, Schistosoma mansoni, etc.,
Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria bimetti, Eimeria maxima, Eimeria maxima Eimerias such as Eimeria ovinoidalis (Eimeria spp.),
Trypanosoma cruzi, Leishmania spp., Plasmodium spp., Babesis spp., Trichomonida spp., Trichomonadida spp. (Giadia spp.), Toxoplasma spp., Shigella amoeba (Entamoeba histolytica), Theylerias (Theileria spp.) And the like, but the present invention is not limited thereto.

The compound of the present invention represented by the formula (I) can be produced, for example, by the following method.
(Production method 1)
The compound represented by the formula (I) can be produced, for example, by reacting the compound represented by the formula (II) with the compound represented by the formula (III).

[Wherein, X is a chlorine atom, a bromine atom, an iodine atom, a C ₁ -C ₄ alkylsulfonyloxy (eg, methanesulfonyloxy), a halosulfonyloxy (eg, fluorosulfonyloxy), a halo (C ₁ -C ₄ ) It represents a leaving group such as alkylsulfonyloxy (for example, trifluoromethanesulfonyloxy) or arylsulfonyloxy (for example, benzenesulfonyloxy), and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , A and W represent the same meaning as described above. ]
The compound of the present invention represented by the formula (I) is obtained by reacting the compound represented by the formula (II) and the compound represented by the formula (III) in a solvent or without a solvent, and optionally in the presence of a base. Can be obtained. When a solvent is used, the solvent used may be inert to the reaction. For example, an ether solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, an aromatic such as benzene, xylene, and toluene. Hydrocarbon solvents, aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane, nitrile solvents such as acetonitrile and propionitrile, N, N-dimethyl Examples include amide solvents such as formamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof. Preferably, acetonitrile, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and a mixture thereof can be used.

  The reaction can be performed in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N, N-dimethylaniline, and 1,4-diazabicyclo [2.2.2]. Organic base such as octane (DABCO), 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) or 1,5-diazabicyclo [4.3.0] -5-nonene (DBN), water Examples thereof include inorganic bases such as sodium oxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and the like. As an equivalent of a base, it can be used in the range of 0.1 to 100 equivalents with respect to the compound represented by the formula (II), and a range of 1 to 40 equivalents is preferable.

  The reaction temperature can be set at an arbitrary temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the range of 0 ° C. to the reflux temperature of the reaction mixture is preferable.

  The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours, and preferably in the range of 1 hour to 48 hours.

  As the equivalent of the substrate, compound (II) can be used in the range of 0.5 to 50 equivalents relative to compound (III), and preferably in the range of 1 to 20 equivalents.

After completion of the reaction, the compound represented by the formula (I) can be obtained from the reaction solution by ordinary post-treatment. For example, water and an extraction solvent such as toluene, ethyl acetate, diethyl ether or chloroform are added to the reaction mixture for extraction, and then the organic layer is dried and concentrated to obtain compound (I). When it becomes necessary to purify the compound, it can be separated and purified by any purification method such as recrystallization or column chromatography.
(Production method 2)
Among the compounds of the present invention, the compound represented by the general formula (I-2) in which R ¹ is phenyl substituted by (Z) _m and Z is carboxy is, for example, the general formula (I-1). It can manufacture by making the compound represented and the compound represented by general formula (IV) react.

Wherein, ^{A 1} represents a lithium atom, sodium atom or potassium ^{atom, R 21} represents a _C 1 -C ₆ alkyl (e.g., methyl, ^{ethyl), R 2, R 3,} R 4, R 5, R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , A, W and m have the same meaning as described above. ]
The compound of the present invention represented by the general formula (I-2) is a compound represented by the general formula (I-1) and a compound represented by the general formula (IV) that can be produced by the production method 1. Can be obtained by reacting in a solvent or without solvent. When using a solvent, the solvent used may be inert to the reaction, for example, water, alcohol solvents such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane. Solvents, aromatic hydrocarbon solvents such as benzene, xylene and toluene, aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane, N, N-dimethyl Examples include amide solvents such as formamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof. Preferable examples include water, methanol, ethanol, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and mixtures thereof.

  As the equivalent of the substrate, compound (IV) can be used in the range of 0.5 to 50 equivalents relative to compound (I-1), and preferably in the range of 1 to 20 equivalents.

  The reaction temperature can be set at an arbitrary temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the range of 0 ° C. to the reflux temperature of the reaction mixture is preferable.

  The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours, and preferably in the range of 1 hour to 48 hours.

After completion of the reaction, the compound represented by the general formula (I-2) can be obtained from the reaction solution by ordinary post-treatment. For example, water and an extraction solvent such as toluene, ethyl acetate, diethyl ether or chloroform are added to the reaction mixture for extraction, and then the organic layer is dried and concentrated to obtain the compound represented by the general formula (I-2). . Moreover, if necessary at the time of extraction, the pH of the aqueous layer can be made acidic. When it becomes necessary to purify the compound, it can be separated and purified by any purification method such as recrystallization or column chromatography.
(Production method 3)
Among the compounds of the present invention, the compound represented by the general formula (I-3) in which R ¹ is phenyl substituted by (Z) _m and Z is C ₁ -C ₆ alkylaminocarbonyl is, for example, It can manufacture by making the compound represented by Formula (I-2) and the compound represented by general formula (V) react.

[Wherein R ²² represents C ₁ -C ₆ alkyl (for example, methyl, ethyl), R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , A, W and m represent the same meaning as described above. ]
The compound of the present invention represented by the general formula (I-3) is a compound represented by the general formula (I-2) and a compound represented by the general formula (V) that can be produced by the production method 2. Can be obtained in a solvent or without a solvent by adding a base if necessary, a condensing agent if necessary, and an additive if necessary. When using a solvent, the solvent used may be inert to the reaction, for example, water, alcohol solvents such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane. Solvents, aromatic hydrocarbon solvents such as benzene, xylene and toluene, aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane, N, N-dimethyl Examples include amide solvents such as formamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof. Preferable examples include water, methanol, ethanol, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and mixtures thereof.

  The reaction can be performed in the presence of a base. Examples of the base that can be used include pyridine, 2,6-lutidine, 4-dimethylaminopyridine, triethylamine, diisopropylethylamine, tributylamine, N, N-dimethylaniline, and 1,4-diazabicyclo [2.2.2]. Organic base such as octane (DABCO), 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) or 1,5-diazabicyclo [4.3.0] -5-nonene (DBN), water Inorganic bases such as sodium oxide, potassium hydroxide, sodium hydride, sodium hydrogen carbonate, potassium carbonate, cesium carbonate and the like can be mentioned. As an equivalent of a base, it can be used in the range of 0.1 to 100 equivalents with respect to the compound represented by the formula (I-2), and a range of 1 to 40 equivalents is preferable.

  The reaction can be carried out in the presence of a condensing agent. As the condensing agent that can be used, 1H-benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate, N, N′-dicyclohexylcarbodiimide, 1- (3-dimethylaminopropyl) -3-ethyl Examples thereof include carbodiimide hydrochloride and 2-chloro-1-methylpyridinium iodide. The equivalent of the condensing agent can be used in the range of 0.1 to 100 equivalents relative to the compound represented by formula (I-2), and the range of 1 to 40 equivalents is preferable.

  The reaction can be carried out in the presence of additives. Examples of the additive that can be used include 3H- [1,2,3] triazolo [4,5-b] pyridin-3-ol, 1-hydroxybenzotriazole and the like. The equivalent of the additive can be used in the range of 0.1 to 100 equivalents with respect to the compound represented by the formula (I-2), and the range of 1 to 40 equivalents is preferable.

  As the substrate equivalent, compound (V) can be used in the range of 0.5 to 50 equivalents relative to compound (I-2), and preferably in the range of 1 to 20 equivalents.

  The reaction temperature can be set at an arbitrary temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the range of 0 ° C. to the reflux temperature of the reaction mixture is preferable.

  The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours, and preferably in the range of 1 hour to 48 hours.

After completion of the reaction, the compound represented by the general formula (I-3) can be obtained from the reaction solution by ordinary post-treatment. For example, water and an extraction solvent such as toluene, ethyl acetate, diethyl ether or chloroform are added to the reaction mixture for extraction, and then the organic layer is dried and concentrated to obtain the compound represented by the general formula (I-3). . When it becomes necessary to purify the compound, it can be separated and purified by any purification method such as recrystallization or column chromatography.
(Production Method 4)
Among the compounds of the present invention, the compound represented by the general formula (I-5) in which R ³ is C ₁ -C ₆ alkyl substituted with hydroxy is, for example, a compound represented by the general formula (I-4) And a compound represented by the general formula (IV).

[Wherein, A ¹ represents a lithium atom, a sodium atom, or a potassium atom, and R ^3A represents C _{1 to} C ₆ alkylene (for example, —CH ₂ —, — (CH ₃ ) CH—, —CH ₂ CH ₂ —, -(CH ₃ ) CHCH _2- , -CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ —), R ^3B represents C ₁ -C ₆ alkyl, R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , A And W represent the same meaning as described above. ]
The compound of the present invention represented by the general formula (I-5) is a compound represented by the general formula (I-4) and a compound represented by the general formula (IV) that can be produced by the production method 1. Can be obtained by reacting in a solvent or without solvent. When using a solvent, the solvent used may be inert to the reaction, for example, water, alcohol solvents such as methanol and ethanol, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane. Solvents, aromatic hydrocarbon solvents such as benzene, xylene and toluene, aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane, halogenated hydrocarbon solvents such as dichloromethane, chloroform and 1,2-dichloroethane, N, N-dimethyl Examples include amide solvents such as formamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide, or a mixed solvent thereof. Preferable examples include water, methanol, ethanol, tetrahydrofuran, N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and mixtures thereof.

  As the substrate equivalent, compound (IV) can be used in the range of 0.5 to 50 equivalents relative to compound (I-4), and preferably in the range of 1 to 20 equivalents.

  The reaction temperature can be set at an arbitrary temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the range of 0 ° C. to the reflux temperature of the reaction mixture is preferable.

  The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours, and preferably in the range of 1 hour to 48 hours.

After completion of the reaction, the compound represented by the general formula (I-5) can be obtained from the reaction solution by ordinary post-treatment. For example, water and an extraction solvent such as toluene, ethyl acetate, diethyl ether or chloroform are added to the reaction mixture for extraction, and then the organic layer is dried and concentrated to obtain the compound represented by the general formula (I-5). . When it becomes necessary to purify the compound, it can be separated and purified by any purification method such as recrystallization or column chromatography.
(Production method 5)
Among the compounds of the present invention, the compound represented by the general formula (I-7) in which R ³ is C ₁ -C ₆ alkyl substituted with C ₁ -C ₆ alkylsulfinyl includes, for example, the general formula (I-6) ) And an oxidizing agent are allowed to react with each other.

[Wherein R ^3C represents C ₁ -C ₆ alkylene (eg, —CH ₂ —, — (CH ₃ ) CH—, —CH ₂ CH ₂ —, — (CH ₃ ) CHCH ₂ —, —CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH ₂ CH _2- , -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH _2- ) and R ^3D is C _{1 to} C ₆ alkyl is represented, and R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , A and W represent the same meaning as described above. ]
The compound of the present invention represented by the general formula (I-7) is prepared by reacting the compound represented by the general formula (I-6) that can be produced by the production method 1 and an oxidizing agent in a solvent or without a solvent. Depending on the case, it can be obtained by reacting in the presence of a catalyst. When a solvent is used, the solvent used may be inert to the reaction. For example, water, a carboxylic acid solvent such as acetic acid, an alcohol solvent such as methanol and ethanol, diethyl ether, tetrahydrofuran, 1,4-dioxane, 1, Ether solvents such as 2-dimethoxyethane, aromatic hydrocarbon solvents such as benzene, xylene and toluene, aliphatic hydrocarbon solvents such as pentane, hexane and cyclohexane, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane Solvents, nitrile solvents such as acetonitrile, propionitrile, amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, N, N′-dimethylimidazolidinone, dimethyl sulfoxide or these And mixed solvents The Preferably, water, acetic acid, tetrahydrofuran, dichloromethane, chloroform, N-methylpyrrolidone, and a mixture thereof can be used.

  Examples of the oxidizing agent include aqueous hydrogen peroxide, sodium hypochlorite, 3-chloroperbenzoic acid and the like. The equivalent of the oxidizing agent can be used in the range of 0.5 to 50 equivalents relative to compound (I-6), and preferably in the range of 1 to 20 equivalents.

  The reaction can be carried out in the presence of a catalyst. Examples of the catalyst that can be used include sodium tungstate dihydrate. As an equivalent of a catalyst, it can be used in 0.005-20 equivalent with respect to compound (I-6), and the range of 0.01-5 equivalent is preferable.

  The reaction temperature can be set at an arbitrary temperature from −80 ° C. to the reflux temperature of the reaction mixture, and the range of 0 ° C. to the reflux temperature of the reaction mixture is preferable.

  The reaction time varies depending on the concentration of the reaction substrate and the reaction temperature, but can usually be arbitrarily set in the range of 5 minutes to 100 hours, and preferably in the range of 1 hour to 48 hours.

  After completion of the reaction, the compound represented by the general formula (I-7) can be obtained from the reaction solution by ordinary post-treatment. For example, water and an extraction solvent such as toluene, ethyl acetate, diethyl ether or chloroform are added to the reaction mixture for extraction, and then the organic layer is dried and concentrated to obtain the compound represented by the general formula (I-7). . When it becomes necessary to purify the compound, it can be separated and purified by any purification method such as recrystallization or column chromatography.

The compound represented by the general formula (II) used in the production method 1 can be produced, for example, according to the route represented by the following reaction formula.
(Reaction Formula 1)

[Wherein, R ¹ , R ² , R ³ and A represent the same meaning as described above. ]
By reacting the compound represented by the general formula (VI) with the compound (VII) according to a known method described in the literature, for example, the method described in Synthesis, 1995, Vol. 4, page 435, etc. A compound represented by the formula (II) can be produced.

  Some of the compounds represented by the general formula (VI) used here are known compounds, and some of them are commercially available. Others can also be easily produced according to the synthesis methods of general known compounds described in the literature.

The compound represented by the general formula (II) used in the production method 1 can be produced, for example, according to the route represented by the following reaction formula.
(Reaction Formula 2)

[Wherein J ¹ represents a chlorine atom, a bromine atom, a C ₁ -C ₄ alkylcarbonyloxy group (eg, pivaloyloxy group), a C ₁ -C ₄ alkoxycarbonyloxy group (eg, isobutyloxycarbonyloxy group) or an azolyl group. (For example, imidazol-1-yl group) and the like, and R ¹ , R ² , R ³ and A represent the same meaning as described above. ]
The compound represented by the general formula (VI) is converted into a hydrazine monohydrate according to a known method described in the literature, for example, the method described in Angewante Chemie International Edition, 2013, Volume 52, page 2559. A compound represented by the general formula (VIII) can be produced by reacting with a hydrate.

  The compound represented by formula (VIII) is converted into compound (IX) according to a known method described in the literature, for example, the method described in Asian Journal of Chemistry, 2004, Vol. 16, 525. The compound represented by general formula (II) can be manufactured by making it react.

  Some of the compounds represented by the general formula (VI) used here are known compounds, and some of them are commercially available. Others can also be easily produced according to the synthesis methods of general known compounds described in the literature.

  Some of the compounds represented by the formula (II) are known compounds, and are produced according to known methods described in the literature, for example, synthesis methods described in Synthesis, 1995, Vol. 4, p. 435, etc. can do.

  Some of the compounds represented by the formula (III) are known compounds and can be produced according to known methods described in the literature, for example, synthetic methods described in International Publication No. 2013/162972.

  When the compound of the present invention is applied as a plant disease or plant pest control agent, it is usually mixed with a suitable solid carrier or liquid carrier, and if desired, a surfactant, penetrant, spreading agent, thickener, antifreeze agent. , Binders, anti-caking agents, disintegrants, anti-decomposition agents, etc., to add liquid concentrates, emulsion concentrates, wettable powders, water soluble powders, granules Water dispersible granule, water soluble granule, suspension concentrate, concentrated emulsion, suspoemulsion It can be put to practical use in preparations of any dosage form such as suspension, microemulsion, dust powder, granule, and gel (gel). In addition, from the viewpoint of labor saving and safety improvement, the preparation of any dosage form can be enclosed in a water-soluble package.

  Examples of solid carriers include quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and other minerals, calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. Examples include salts, synthetic silicic acid and synthetic silicates.

  Examples of the liquid carrier include alcohols such as ethylene glycol, propylene glycol and isopropanol, aromatic hydrocarbons such as xylene, alkylbenzene and alkylnaphthalene, ethers such as butyl cellosolve, ketones such as cyclohexanone, and esters such as γ-butyrolactone. And acid amides such as N-methylpyrrolidone and N-octylpyrrolidone, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water.

  These solid and liquid carriers may be used alone or in combination of two or more.

  Examples of the surfactant include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene fatty acid ester, sorbitan fatty acid ester and polyoxyethylene sorbitan. Nonionic surfactant such as fatty acid ester, alkyl sulfate, alkylbenzene sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkyl naphthalene sulfonate, salt of formalin condensate of naphthalene sulfonate, Salt of formalin condensate of alkylnaphthalenesulfonic acid, polyoxyethylene alkylaryl ether sulfate and phosphate, polyoxyethylene polystyrene Anionic surfactants such as phenyl ether sulfate and phosphate, polycarboxylate and polystyrene sulfonate, cationic surfactants such as alkylamine salt and alkyl quaternary ammonium salt, and amphoteric interfaces such as amino acid type and betaine type An activator is mentioned.

  The content of these surfactants is not particularly limited, but is usually preferably in the range of 0.05 to 20 parts by weight with respect to 100 parts by weight of the preparation of the present invention. These surfactants may be used alone or in combination of two or more.

  In addition, when the compound of the present invention is used as an agrochemical, other types of herbicides, various insecticides, acaricides, nematicides, fungicides, plant growth regulators, co-agents, and the like, can be used when formulated or sprayed. You may mix and apply it with a power agent, a fertilizer, a soil conditioner, etc.

  In particular, by applying it in combination with other agricultural chemicals or plant hormones, it can be expected to reduce costs by reducing the amount of applied medicine, expand the bactericidal insecticidal spectrum due to the synergistic action of the mixed drugs, and higher pest control effects. At this time, a combination with a plurality of known agricultural chemicals is also possible. Examples of the type of agrochemical used in combination with the compound of the present invention include compounds described in the 1999 edition of Farm Chemicals Handbook (Farm Chemicals Handbook). Specific examples of common names are as follows, but the general names are not necessarily limited to these.

Bactericides: acibenzolar-S-methyl, acipetacs, aldimorph, allyl alcohol, ametoctradin, amisulbrom, amisulbrom Phos (ampropropylfos), anilazine (anilazine), azaconazole, azithyram, azoxystrobin, barium polysulfide (barium polysulfide), benalaxylb Benodanil, benomyl, benquinox, bentaluron, benchavaricarb-isopropyl, benhiazole, bezmamol (ben), benzacril (ben) Vindiflupyr, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S (blasticin-S), borde liquor (x) ), Bromconazole, bupirimate, butiobate, butyramine, butyl sulfur, calc sulfur, capta b, captan b, capta c Carbendazim, carboxin, carpropamide, carvone, cheshunt mixture, chinomethionate, clobenchon, clobenchazone ifmetane), chloranil, chlorfenazol, chloroneb, chloropicrin, chlorquinolate, chlorquinolate, chlorquinolate, chlorquinolate, chlorquinolate, chlorquinolate (Copper acetate), basic copper carbonate (basic), cupric hydroxide, copper naphthenate, copper oleate, basic copper chloride (copper x) chloride, copper sulfate, copper sulfate, basic, copper zinc chromate, cresol, cufraneb, cuprobum, cuprobum , Cyclfuramid, Cyclofenamide, Cyxendroyl, Cyprodazole, Cyprodazole, Cyprodane, Cyprodane (Dazomet), debacarb, decafentin, dehydroacetic acid, dichlorfluanid, dichlone, dichlorofen, diclozoline, diclozoline Diclobutrazol, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, diflumetrim, diflumetrim, diflumetrim , Dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap-4, dinocap-4, dinocap-4, dinocap-4 (Dinocap-6), dinocton, dinosulfone, dinoterbon, diphenylamine, dipyrithione, disulfiramit, ditalimone (DNO ), Dodemorph, dodine, drazoxolone, edifenphos, enestrobin, epoxizone, ethaboxamet, ethaboxamone , Ethirimol, ethoxyquin, etridiazole, famoxadone, fenamidone, fenaminosulfur, fenapamol Fenbuconazole, Fenfuram, Fenhexamide, Fennitropan, Fenoxanil, Fenpiclonil, Fenpropimine, Fenpropimorphin, Fenpropimorphin Fentin, ferbam, ferimzone, fluazinam, fludioxonil, fluphenoxystrobin, flumetover, flumorph ph), fluopicolide, fluopyram, fluorimide, fluotrimazole, fluoxasolflu, fluquinconazole, fluquinconazole, fluquinconzol
Flutolanil, flutianil, flutriafol, fluxapyroxad, folpetto, fosetyl-aluminum, fotalidol, buverizole Furalaxyl, furametopyr, furcarbanil, fluconazole, furconazole-cis, furmecylur, phlophanate, phlophanate Ofluvin (griseofulvin), guazatine (halacrinete), hexachlorobenzene (hexachloroazole), hexylthiofos (hexylthiofos), oxyquinoline (hixylol) Imazalil, imibenconazole, iminoctadin-albesylate, iminoctadate-triacetate, iodocarba, iodocarb Ipconazole, iprobenfos, iprodione, iprovalicalcarb, isofetamid, isothiaisone, isoprotialine, isoprothiazole , Kresoxim-methyl, laminarin, mancopper, mancozeb, mandestrobin, mandipropamide, manneprop aneb), mebenil, mecarbinzid, mepanipyrim, mepronil, metalaxyl, metalaxyl-M (metaxyl-M), metamol (Metconazole), metasulfocarb (methasulfocarb), metfuroxam (metfuroxam), metyram (methinostrobin), metrafenone (metrafone), metsulfobene (metsulfoven) nil), microzoline, nabam, naphthifine, natamycin, nickel bis (dimethythythiocarbamate), nitrostyrene (nitro-propylene) (Nuarimol), octinoline, offase, oryastrobine, oxadixyl, oxathiapiprolin, oxyquinoline copper (oxine copperx) oconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflurophenol, pentochlorophenol, pentachlorophenol 2-phenylphenol, phosdiphen, phthalide, picarbutrazox, picoxystrobin, piperalin, polycarbam te), polyoxins (polyoxins), polyoxin-D (polyoxorim), potassium azide (potassium hydrogen carbonate), pro salt (pro) zole (pro) azole, procazole (pro salt) propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothiocarb, pyrazophos methyl, pyrazophos, pyrazophos, pyrazophos Pyrifenox, pyrimethanil, pyriminostrobin, pyroquiron, prothiocarb, pioconol, p, piroconol, piroconol, p (Pyridinitol), pyriophenone, pyrisoxazole, pyroxychlor, piroxyfur, quinacetol-sulfate, quinacetol-sulfide amid), quinconazole, quinoxyfen, quintozene, rabenzazole, salicylanilide, silithione, sulthione, sulthiophene hydrocarbylate, sodium hypochlorite, spiroxamine, sulfur, tebuconazole, tebufloquin, teflotamte Nazen (tecnazene), tecolam, tetraconazole, thiabendazole, thiadifluor, thiothiophene, thioflumide, thiflumide, thiflumide ), Thiophanate-methyl, thiuram, thiadinyl, thioxymid, tolcrofos-methyl, tolprocarb, tolylfluoride (tolylfluoride) nid), triadimefon, triadimenol, triamifos, triarimol, triazbutyl, triazoxide, debutyl trioxide, tributyltin oxide (t) Tricyclazole, tridemorph, trifloxystrobin, triflumizole, trifoline, triticonazole, triticonazole, triticonazole, triticonazole Phenalate, vinclozolin, zalilamid, zinc naphthenate, zinc sulfate, zineb, ziram, zymamide, zoxamide, zoxamide Shiitake fruiting body extract, MIF-1002 (test name), OAF-211 (test name), SB-4303 (test name) and the like.

  Insecticides: abamectin, acephate, acetamiprid, aphidopyropen, afoxalaner, phosphine, alancarb, aldharb Ethyl (azinphos-ethyl), azinephos-methyl, bacillus thuringiensis, bendiocarb, benfluthrin, benfurcarb Sultap, bifenthrin, bioallethrin, bioresmethrin, bistrifluron, buprofezin, buprofezin, buprofezin, buprofezin Carbosulfan, cartap, chloranthraniprole, chlorethoxyfos, chlorfenapyr, chlorfenvinphos, chlorfenvinphos Lorfluazuron, chlormefos, chlorpyrifos, chlorpyrifos-methyl, phlocyanoside, crothianidin (clo) Cycliliprole, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin (gamma-cyhal) thrin), lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin (zeta-permethrin) (Cyphenothrin), cyromazine, deltamethrin, diafenthiuron, diazinon, dichlorvos, diflubenzuron, diflubenzuron, diflubenzuron thylvinphos), dinotefuran, diophenolan, disulfoton, emamectin benzoate, empentrin, ulsulfane, endosulfan, endosulfan. Esfenvalerate, etiofencarb, ethiprole, etofenprox, etrimfos, fenitrothion, fenocarb obucarb, phenoxycarb, fenthion, fenvalerate, fipronil, flometoquin, flonicamid, fluadifluron (Flucycloxuron), flucytrinate, fluphenerim, flufenoxuron, flufiprole, flumethrin, flupyradiuron (flupyradiuron) luuralaner, fulvalinate, tau-fulvalinate, fonofos, furathiocarb, halofenozide, heptafluthurflurane Non (hydramethylnon), imidacloprid, imiprothrin, indoxacarb, indoxacarb-MP (indoxacarb-MP), isoprocarb isoprectin, isoxatictin mectin, lufenuron, malathion, meperfluthrin, metaflumizone, metadehyde, methalithone, methamidone, methamidone, methamidone (Methoprene), methoxychlor, methoxyphenozide, methoffluthrin, muscarfure, nitenpyram, novaluron, novaluron Flumuron, ometoate, oxydemethon-methyl, parathion-methyl, permethrin, phenothrin, phenate, phenate, phenate, phenate, phenate. phosalone, phosmet, phoxim, pirimicarb, pirimiphos-methyl, profenofos, prothiofos, pymetrozine, pymetrozine fos), pyrethrins, pyridalyl, pyrifluquinazone, pyriprole, pyriproxyfen, spiroten, resmetrin, rotenon Spinosad, spirotetramat, sulfotep, sulfoxaflor, tebufenozide, teflubenzuron, tefluthrin, tefluthrin Phosbu (terbufos), tetrachlorovinphos (tetrachlorvinphos), tetramethrin, d-T-80-phthalthrin, tetramethylfluthrin, thiacloprid (thiaclopride), thiaclopride (Thiocyclam), thiodicarb, thiophanox, thiomethon, tolfenpyrad, tralomethrin, transfluthrint, triflutrint ), Trichlorfon, triflumuron, ME5382 (test name), NC-515 (test name), and ZDI2501 (test name).

  Acaricides: acequinocyl, acrinathrin, amidoflumet, amitraz, azocyclotin, benzoximate, benzopromate Phentezine, cyenopyrafen, cyflumethofen, dicophor, dienochlor, etoxazole, fenazafen in oxide, phenothiocarb, fenpropathrin, fenpyroximate, fluripyrim, flumethyx, fenfroximate propargite, pyruvumide, pyridaben, pyrimidifene, spirodiclofen, spiromesifen, tebufenpyrad (tebufenpyrad) fenpyrad) and NA-89 (test name).

  Nematicides: kazusafos, diclofenthion, ethoprofos, fenamifos, fluensulfos, fluthiafos, fosthiat, fosthiasto , Isazofos, methyl bromide, methyl isothiocyanate, oxamyl, sodium azide, BYI-1921 (test name) and MAI-08015 Such.

  Anthelmintic: acriflavine, albendazole, atovagone, azithromycin, bisionol, bromfenodac, bromofenfos chloroquine, clazuril, clindamycin, chlorsulon, closantel, coumafos, chlorofendi, dichlorophenol Diethylcarbamazine, diminazene, disophenol, dithizanine iodide, ect, decine, decide, decide, decide ), Fenbendazole, flubendazole, furazolidone, glycalpyramide, imidocarb, ivermectin ( vermectin, levamisole, mebendazole, mefloquine, melarsamine hydrochloride, methiridine, methiridine, metridine Morantel (morantel), moxidectin, nicarbazin, niclosamide, nitroskanate, nitroxynil, omphalo Oxphaltine, oxantellate, oxendazole, oxclodide, oxclodide Piperazine acid, piperazine citrate, piperazine phosphate, PNU-97333 (paraherquamide A), PNU-141962 (2-dexapuy, 2-dex) Radiquaantel, primaquine, propetamphos, dipoxur, sulphine, sulphine, selenium, selenium Sulfadoxine, sulfamerazine, sulfamonomethoxine, sulfamoyldapson, thiabendazole, tinidazole (ti) such as nidazole, toltrazuril, tribromsalan, and triclabendazole.

  Antifungal agents: ketoconazole and miconazole nitrate.

  Antibacterial agents: amoxicillin, ampicillin, betoxazine, bitionol, bronopol, cefapirin, cefazolin, cefazolin, cefazolin, cefazolin, cefazolin, cefazolin (Chlortetracycline), clavulanic acid, danofloxacin, difloxacin, dinitroxine, enrofloxacin, florfenicol (florenicol) , Lincomycin, lomefloxacin, marbofloxacin, miloxacin, milosamycin, nitrapirin, inloxin, norfloxacin (nor) Orbifloxacin, oxolinic acid, oxytetracycline, penicillin, streptomycin, thiamphenicol, thiamphenicol Tiamulin fumarate, tilmicosin phosphate, tylosin isovaleric acid, tyrosin phosphate, turathrneuminum shell Calcium), Talalomyces spp., Trichoderma spp. And Unioniolium spp.

  The application amount of the compound of the present invention varies depending on the application scene, the application time, the application method, the cultivated crops, etc., but generally the amount of the active ingredient is suitably about 0.005 to 50 kg per hectare (ha).

Next, formulation examples of the preparation when the compound of the present invention is used are shown. However, the formulation examples of the present invention are not limited to these. In the following formulation examples, “parts” means parts by weight.
[Wettable powder]
Compound of the present invention 0.1 to 80 parts Solid carrier 5 to 98.9 parts Surfactant 1 to 10 parts Others 0 to 5 parts Others include, for example, anti-caking agents and decomposition inhibitors.
〔emulsion〕
Compound of the present invention 0.1-30 parts Liquid carrier 45-95 parts Surfactant 4.9-15 parts Others 0-10 parts Others include, for example, spreading agents, decomposition inhibitors and the like.
[Suspension]
Compounds of the present invention 0.1 to 70 parts Liquid carrier 15 to 98.89 parts Surfactant 1 to 12 parts Others 0.01 to 30 parts Others include, for example, antifreezing agents and thickeners.
(Granule wettable powder)
Compound of the present invention 0.1 to 90 parts Solid carrier 0 to 98.9 parts Surfactant 1 to 20 parts Others 0 to 10 parts Others include, for example, binders and decomposition inhibitors.
[Liquid]
Compound of the present invention 0.01 to 70 parts Liquid carrier 20 to 99.99 parts Others 0 to 10 parts Other examples include antifreezing agents and spreading agents.
[Granule]
Compound of the present invention 0.01 to 80 parts Solid carrier 10 to 99.99 parts Others 0 to 10 parts Others include, for example, binders, decomposition inhibitors and the like.
[Dust]
Compound of the present invention 0.01 to 30 parts Solid support 65 to 99.99 parts Others 0 to 5 parts Other examples include a drift inhibitor and a decomposition inhibitor.

  In use, the preparation is sprayed diluted with water 1 to 10,000 times or without dilution.

Next, although the formulation example of the agricultural and horticultural fungicide which uses this invention compound as an active ingredient is shown concretely, it is not limited only to these. In the following formulation examples, “parts” means parts by weight.
[Formulation Example 1] Emulsion Compound No. 1 of the present invention. A-1 20 parts Methylnaphthalene 55 parts Cyclohexanone 20 parts Solpol 2680 5 parts (Mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industries, Ltd. trade name)
The following are uniformly mixed to obtain an emulsion. In use, the emulsion is diluted 50 to 20000 times and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[Formulation Example 2] Wetting agent Compound No. A-1 25 parts Pyrophyllite 66 parts Solpol 5039 4 parts (Anionic surfactant: Toho Chemical Industries, Ltd. trade name)
Carplex # 80D 3 parts (White Carbon: Shionogi & Co., Ltd. trade name)
2 parts or more of calcium lignin sulfonate are mixed and ground uniformly to obtain a wettable powder.

In use, the wettable powder is diluted 50 to 20000 times and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[Formulation Example 3] Powder Compound Nos. A-1 3 parts Carplex # 80D 0.5 part (White carbon: Shionogi & Co., Ltd. trade name)
Kaolinite 95 parts Diisopropyl phosphate 1.5 parts or more uniformly mixed and pulverized to form a powder. In use, the powder is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[Formulation Example 4] Granules of the present compound No. A-1 5 parts Bentonite 30 parts Talc 64 parts Calcium lignin sulfonate 1 part The above mixture is uniformly mixed and ground, a small amount of water is added and mixed with stirring, granulated with an extrusion granulator, dried and granulated. And In use, the above granule is sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[Formulation Example 5] Suspending Agent Compound No. A-1 25 parts Solpol 3353 5 parts (Nonionic surfactant: Toho Chemical Co., Ltd. trade name)
Lnox 1000C 0.5 part (Anionic surfactant: Toho Chemical Co., Ltd. trade name)
Xanthan gum (natural polymer) 0.2 parts Sodium benzoate 0.4 parts Propylene glycol 10 parts Water 58.9 parts The above ingredients except the active ingredient (the compound of the present invention) are uniformly dissolved, then the compound of the present invention is added. After thorough stirring, a flowable agent is obtained by wet grinding with a sand mill. In use, the flowable agent is diluted 50 to 20000 times and sprayed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
[Formulation Example 6] Granular wettable powder Compound No. of the present invention. A-1 75 parts Hightenol NE-15 5 parts (Anionic surfactant: trade name of Daiichi Kogyo Seiyaku Co., Ltd.)
Vanillex N 10 parts (anionic surfactant: Nippon Paper Industries Co., Ltd. trade name)
Carplex # 80D 10 parts (White Carbon: Shionogi & Co., Ltd. trade name)
The above mixture is uniformly mixed and pulverized, a small amount of water is added, mixed with stirring, granulated with an extrusion granulator, and dried to obtain a dry flowable agent. In use, it is diluted 50 to 20000 times with water and sprayed so that the active ingredient is 0.005 to 50 kg per hectare.

  Application methods of the compound of the present invention include foliage spraying, soil treatment, seed disinfection and the like, but they are also effective in general methods usually used by those skilled in the art.

  Hereinafter, the present invention will be described in more detail by specifically describing synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

[Synthesis example]
Synthesis example 1
(1E, N′E) -2-Methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl N ′-(1- (4-fluorophenyl) Ethylidene) Preparation of acetohydrazonate (present compound No. B-1)
(E) -N ′-(1- (4-fluorophenyl) ethylidene) acetohydrazide 0.21 g (1.06 mmol) in 3 ml of N, N-dimethylformamide 0.12 g (1.06 mmol) of potassium tert-butoxide Was added at room temperature and stirred for 30 minutes. After completion of stirring, 0.20 g (0.71 mmol) of 1- (2- (bromomethyl) -3-methylphenyl) -4-methyl-1H-tetrazol-5 (4H) -one was added to the reaction mixture at room temperature. And stirring was continued for 5 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture to stop the reaction, and the reaction solution was extracted with ethyl acetate (10 ml × 1). The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography {n-hexane: ethyl acetate = 2: 1 (volume ratio)} to obtain 0.10 g of the desired product as white crystals.
Melting point: 111-113 ° C
Synthesis example 2
4-((E) -1-((E)-(1-((2-methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl) Preparation of oxy) propylidene) hydrazono) ethyl) benzoic acid (Compound No. B-80 of the present invention)
Methyl 4-((E) -1-((E)-(1-((2-methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl) 2 ml of a 0.5 M aqueous sodium hydroxide solution was added to a solution of 60 mg (0.13 mmol) of oxy) propylidene) hydrazono) ethyl) benzoate in 13 ml of ethanol at room temperature and stirred for 2 hours. Further, 2 ml of 0.5M aqueous sodium hydroxide solution was added at room temperature, and stirring was continued for 22 hours. After completion of the stirring, the solvent was distilled off under reduced pressure. 10 ml of water was added to the reaction mixture, and the aqueous layer was washed with chloroform and hexane (each 10 ml × 1). Concentrated hydrochloric acid was added to the obtained aqueous layer under ice cooling to adjust the pH to 1. The crystals precipitated in the aqueous layer were collected by filtration and washed with 1 ml of diisopropyl ether to obtain 35 mg of the desired product as white crystals.
Melting point: 147-151 ° C
Synthesis example 3
(1E, N′E) -2-Methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl N ′-(1- (4- (methylcarbonyl) ) Preparation of phenyl) ethylidene) propionohydrazonate (present compound No. B-79)
4-((E) -1-((E)-(1-((2-methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl) Oxy) propylidene) hydrazono) ethyl) benzoic acid 25 mg (0.06 mmol), methylamine hydrochloride 5 mg (0.07 mmol), 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride 13 mg (0.07 mmol) ), A mixed solution of 14 mg (0.14 mmol) of triethylamine and 3 ml of dichloromethane was stirred at room temperature for 21 hours. After completion of the stirring, 5 ml of water was added to the reaction mixture, and the reaction solution was extracted with dichloromethane (5 ml × 1). The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated crystals were washed with 1 ml of a mixed solution of diisopropyl ether-ethanol (volume ratio 10: 1) to obtain 12 mg of the desired product as white crystals.
Melting point: 164-167 ° C
Synthesis example 4
(1E, N′E) -2-Methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl N ′-(1- (4-fluorophenyl) Ethylidene) -2-hydroxyacetohydrazonate (Compound No. B-88 of the present invention)
(E) -2-((E)-(1- (4-fluorophenyl) ethylidene) hydrazono) -2-((2-methyl-6- (4-methyl-5-oxo-4,5-dihydro-) To a solution of 17 mg (0.04 mmol) of 1H-tetrazol-1-yl) benzyl) oxy) ethyl acetate in 3 ml of ethanol was added 450 mg of 1M aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for 2 hours. After completion of the stirring, the solvent was distilled off under reduced pressure. 5 ml of water was added to the reaction mixture, and the reaction solution was extracted with ethyl acetate (5 ml × 1). The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated crystals were washed with 1 ml of diisopropyl ether to obtain 7 mg of the desired product as white crystals.
Melting point: 106-108 ° C
Synthesis example 5
(1E, N′E) -2-Methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl N ′-(1- (4-fluorophenyl) Ethylidene) -2- (methylsulfinyl) acetohydrazonate (Compound No. B-107 of the present invention)
(1E, N′E) -2-Methyl-6- (4-methyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl) benzyl N ′-(1- (4-fluorophenyl) Ethylidene) -2- (methylthio) acetohydrazonate 0.16 g (0.36 mmol) in dichloromethane 3 ml solution under ice-cooling 70 wt% 3-chloroperbenzoic acid (containing 30 wt% water) 74 mg ( 0.30 mmol) was added and stirred at room temperature for 1 hour. After completion of the stirring, 5 ml of saturated aqueous sodium bicarbonate was added to the reaction mixture to stop the reaction, and the reaction solution was extracted with chloroform (5 ml × 1). The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated crystals were washed with 2 ml of a mixed solution of diisopropyl ether-ethanol (volume ratio 10: 1) to obtain 0.13 g of the desired product as white crystals.
Melting point: 107-110 ° C
[Reference example]
Below, the manufacturing method of the manufacturing intermediate of this invention compound is shown as a reference example.

Reference example 1
Synthesis of (E) -N ′-(1- (4-fluorophenyl) ethylidene) propionohydrazide 0.61 g (4.42 mmol) of 1- (4-fluorophenyl) ethanone, 0.58 g of propionohydrazide (6. 58 mmol), 10 ml of ethanol and 1 ml of acetic acid were heated to reflux and stirred for 1 hour. After completion of the stirring, 50 ml of water was added to the reaction solution. Crystals precipitated in the reaction solution were collected by filtration to obtain 0.69 g of the desired product as white crystals.

Reference example 2
Step 1; Synthesis of (E) -3- (1-hydrazonoethyl) benzonitrile 1.38 g (27.6 mmol) of hydrazine monohydrate in a solution of 2.00 g (13.8 mmol) of 3-acetylbenzonitrile in 15 ml of methanol. ) At room temperature and stirred for 12 hours. After completion of the stirring, 50 ml of water was added to the reaction mixture to stop the reaction, and the reaction solution was extracted with chloroform (50 ml × 1). The obtained organic layer was washed with water, dehydrated and dried over saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.05 g of the desired product as an oil.

Step 2: Synthesis of (E) -N ′-(1- (3-cyanophenyl) ethylidene) propionohydrazide (E) -3- (1-hydrazonoethyl) benzonitrile 1.00 g (6.28 mmol), To a mixed solution of 0.76 g (7.54 mmol) of triethylamine and 20 ml of dichloromethane, 0.64 g (6.91 mmol) of propionic acid chloride was added dropwise under ice cooling. After completion of dropping, the mixture was stirred at room temperature for 1 hour. After completion of the stirring, 20 ml of water was added to stop the reaction, and the reaction solution was extracted with dichloromethane (20 ml × 1). The obtained organic layer was dehydrated and dried with saturated brine and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The precipitated crystals were washed with diisopropyl ether to obtain 1.18 g of the desired product as white crystals.

  This invention compound can be manufactured according to the said manufacturing method and an Example. Examples of hydrazone derivatives included in the present invention produced in the same manner as in Synthesis Example 1 to Synthesis Example 5 are shown in Tables 1 to 16, but the hydrazone derivatives included in the present invention are limited to these. is not.

  In addition, the production intermediate of the compound of the present invention can be produced according to the above Reference Example. The production intermediates of the compound of the present invention produced in the same manner as in Reference Example 1 or Reference Example 2 are shown in Tables 18 to 27, but the production intermediate of the compound of the present invention is not limited thereto.

  In the table, Me represents a methyl group, Et represents an ethyl group, nPr represents an n-propyl group, iPr represents an i-propyl group, cPr represents a cyclopropyl group, sBu represents an s-butyl group, and tBu represents A t-butyl group, cBu represents a cyclobutyl group, cHex represents a cyclohexyl group, Ph represents a phenyl group, Bn represents a benzyl group, and Ac represents an acetyl group.

  In the table, “* 1” means that the property of the compound was oily or resinous.

  Moreover, the substituent represented by U-1a, U-1b, U-1c, U-2a, U-2b, U-2c in a table | surface represents the following structure, respectively.

[Table 1]

------------------------
No. (Z) _m R ² R ³ Melting point (° C)
------------------------
A-1 4-F Me Me 95-97
A-2-Me Me 45-47
A-3 4-Cl Me Me 87-90
A-4 4-CF ₃ Me Me 58-61
A-5 4-OMe Me Me 80-82
A-6 4-Me Me Me 76-78
A-7 4-F Me Et 40-50
A-8 4-F Me iPr * 1
A-9 4-F Me Ph 74-82
A-10 3-F Me Me 74-82
A-11 2-F Me Me 39-45
A-12 4-F Me nPr * 1
A-13 3-F Me Et * 1
A-14 2-Cl Me Me 56-60
A-15 4-FH Me 131-134
A-16 4-F Me cPr 56-59
A-17 2-F Me Et * 1
A-18-Me Et 60-65
A-19 3-OMe Me Me 75-78
A-20 2-OMe Me Me * 1
A-21 2,4-di-F Me Et 40-43
A-22 4-F Me tBu * 1
A-23 3-Cl Me cPr * 1
A-24 3-OMe Me cPr * 1
A-25 3-Br Me Et 59-61
A-26 3-Cl Me Et * 1
------------------------
[Table 2]

------------------------------
No. (Z) _m R ² R ³ R ⁶ Melting point (° C)
------------------------------
B-1 4-F Me Me Me 111-113
B-2 4-F Me Me Cl 105-107
B-3 4-F Me H Me 137-139
B-4 4-F Me Et Me 80-82
B-5 4-F Et Me Me 119-122
B-6-Me Me Me 77-79
B-7 4-Cl Me Me Me 114-116
B-8 4-CF ₃ Me Me Me 98-100
B-9 4-OMe Me Me Me 106-108
B-10 4-Me Me Me Me 80-82
B-11 3-F Me Me Me 92-94
B-12 2-F Me Me Me 114-116
B-13 2,4-di-F Me Me Me 148-150
B-14 4-F Me Me Br 110-114
B-15 3-F Me Et Me 73-77
B-16 2-F Me Et Me 65-72
B-17 4-F Me Me CF ₃ 82-84
B-18-Me Me CF ₃ * 1
B-19 4-F Me nPr Me 62-66
B-20 4-F Me Me F 117-122
B-21 4-F Me iPr Me 81-86
B-22 3-F Me Me Cl 103-105
B-23-Me Me Cl 86-88
B-24 4-F Me Et Cl 66-69
B-25 2-Cl Me Me Me 131-133
B-26 3-OMe Me Me Me 55-61
B-27 2-OMe Me Me Me 55-60
B-28 2-Me Me Me Me 87-89
B-29-Me Et Me 47-51
B-30 3-Me Me Et Me 45-46
B-31 2,6-di-F Me Et Me 98-99
B-32 2,3-di-F Me Me Me 138-141
B-33 3-F Me Et Cl 70-72
B-34 3-Cl Me Et Me 69-70
B-35-Me Et Cl 82-85
B-36 4-F Me cPr Me 83-86
B-37 4-SMe Me Me Me 103-105
B-38 2-F Me Et Cl 69-71
B-39 4-F Me CH ₂ OMe Me 91-93
B-40 4-F Me CF ₃ Me * 1
B-41 2-F Me nPr Me * 1
B-42 4-FH Me Cl 173-175
B-43 4-NO ₂ Me Me Me 132-134
B-44 4-Ph Me Me Me 153-155
B-45 2-OMe Me Et Me 70-74
B-46 4-OMe Me Et Me 98-101
B-47 4-FH Me Me 162-164
B-48-Me cPr Me 63-66
B-49-Ph Et Me * 1
B-50 3-OMe Me Et Me 67-70
B-51 4-F Me Et Et 66-68
B-52 3,4-di-F Me Et Me 83-85
B-53-Ph Me Me * 1
B-54 4-F Me cPr Et * 1
B-55 2,4-di-F Me Et Me 166-168
B-56 2,5-di-F Me Et Me 107-111
B-57 4-F Me CH ₂ (cPr) Me 79-82
B-58 2-F Me cPr Me * 1
B-59 3-F Me cPr Me * 1
B-60 4-CO ₂ Me Me Et Me 109-111
B-61 3-Cl-4-F Me Et Me 102-105
B-62 4-F Me U-1a Me * 1
B-63 4-F Me U-1b Me 87-90
B-64 3-Br Me Et Me 66-68
B-65 3-OCF ₃ Me Et Me * 1
B-66-CH ₂ OMe Et Me 91-93
B-67 3-CF ₃ Me Et Me * 1
B-68 3-CN Me Et Me 52-55
B-69 4-F Me sBu Me * 1
B-70 4-F Me cBu Me 92-95
B-71 4-F Me CH ₂ OEt Me 78-80
B-72 4-F Me tBu Me * 1
B-73 4-F Me C (Me) ₂ OH Me * 1
B-74 3-Cl Me cPr Me * 1
B-75 4-F Me U-2a Me 89-92
B-76 4-F Me U-2b Me 111-113
B-77 4-F Me U-2c Me 127-129
B-78 4-F Me CO ₂ Et Me * 1
B-79 4-C (O) NHMe Me Et Me 164-167
B-80 4-CO ₂ H Me Et Me 147-151
B-81 4-C (= NOMe) Me Me Et Me * 1
B-82 4-tBu Me Et Me 94-96
B-83 4-F Me cPr Cl 93-94
B-84 3-OMe Me cPr Me * 1
B-85 3,5-di-F Me Et Me 88-90
B-86 2,5-di-Me Me Et Me * 1
B-87 2,5-di-Me Me cPr Me * 1
B-88 4-F Me CH ₂ OH Me 106-108
B-89 4-F Me CH ₂ OAc Me 89-92
B-90 3-Cl-4-F Me cPr Me 88-89
B-91 3,4-di-Cl Me Et Me 115-116
B-92 3,4-di-OMe Me Et Me 111-114
B-93 4-F Me Et F 68-70
B-94 4-F Me cPr F 120-122
B-95 4-F Me C (OMe) ₂ Me Me 132-135
B-96 4-F Me U-1c Me 104-107
B-97 4-F Et Et Me 97-99
B-98 4-F Me 4-MeO-Bn Me 126-127
B-99 3-Cl Me Et F * 1
B-100 4-F Me CH ₂ SMe Me 84-86
B-101 4-F Me 4-F-Bn Me 103-106
B-102 3-Br Me Et Cl 91-93
B-103 4-Cl Me cPr Me 113-115
B-104 3-Br Me cPr Me * 1
B-105 3-Br Me Me Me 75-76
B-106 3-Ac Me Et Me * 1
B-107 4-F Me CH ₂ SOMe Me 107-110
B-108 4-F Me Et SMe 48-51
B-109 3-OMe Me Et Cl * 1
B-110 3-Br-4-F Me Et Me 96-97
------------------------------
[Table 3]

----------------------------
No. (Z) _m R ² R ³ R ⁷ Melting point (° C)
----------------------------
C-1 4-F Me Me F 99-103
C-2 4-F Me Et F 70-75
----------------------------
[Table 4]

----------------------------
No. (Z) _m R ² R ³ R ⁸ Melting point (° C)
----------------------------
I-1 4-F Me Et F 70-73
I-2 4-F Me Et Me 81-83
I-3 4-F Me cPr Me 100-102
----------------------------
[Table 5]

----------------------------
No. (Z) _m R ² R ³ R ⁹ Melting point (° C)
----------------------------
J-1 4-F Me Me F 40-42
J-2 4-F Me Et F * 1
J-3 4-F Me Et Me * 1
----------------------------
[Table 6]

------------------------
No. (Z) _n R ² R ³ Melting point (° C)
------------------------
D-1 3,5-di-Cl Me Me 73-78
D-2 6-Me Me Me 78-83
D-3 3,5-di-Cl Me Et 69-74
D-4 6-OMe Me Me 103-105
D-5 6-OMe Me Et 107-109
------------------------
[Table 7]

----------------------------
No. (Z) _n R ² R ³ R ⁶ Melting point (° C)
----------------------------
E-1 3,5-di-Cl Me Me Me 122-124
E-2 3,5-di-Cl Me Et Me 119-124
E-3 3,5-di-Cl Me nPr Me 59-64
E-4 3,5-di-Cl Me Et Cl 108-110
E-5 6-Me Me Me Me 85-87
E-6 6-Cl Me Me Me 117-119
E-7 6-Cl Me Et Me 167-169
E-8 3,5-di-Cl Me iPr Me * 1
E-9 3,5-di-Cl Me Me CF ₃ 85-87
E-10 6-OMe Me Me Me 120-122
E-11-Me Et Me 81-83
E-12 6-Cl Me cPr Me * 1
E-13 6-OMe Me cPr Me 75-78
E-14 6-Cl Me Et Cl 113-114
E-15 6-OMe Me Et Me 103-106
E-16 6-Cl Me Et F 69-72
E-17 6-Br Me Et Me 80-81
E-18 4-Me Me Et Me 118-120
E-19 5,6-di-Me Me Et Me 111-113
----------------------------
[Table 8]

----------------------------
No. (Z) _n R ² R ³ R ⁶ Melting point (° C)
----------------------------
K-1 6-Cl Me Et Me 103-105
K-2 6-Cl Me cPr Me 103-105
K-3-Me Et Me 108-110
----------------------------
[Table 9]

----------------------------
No. (Z) _n R ² R ³ R ⁶ Melting point (° C)
----------------------------
L-1-Me Et Me 93-95
----------------------------
[Table 10]

----------------------------
No. (Z) _p R ² R ³ R ⁶ Melting point (° C)
----------------------------
M-1-Me Me Me 94-96
M-2 5-Cl Me Et Me 109-110
M-3-Me Et Me 79-82
M-4 5-Cl Me cPr Me 122-123
M-5 5-Me Me Et Me 94-96
----------------------------
[Table 11]

----------------------------
No. (Z) _p R ² R ³ R ⁶ Melting point (° C)
----------------------------
N-1-Me Et Me 84-86
----------------------------
[Table 12]

----------------------------
No. (Z) _r R ² R ³ R ⁶ Melting point (° C)
----------------------------
O-1-Me Et Me 78-82
O-2-Me cPr Me * 1
O-3 4-Me Me Et Me 105-107
----------------------------
[Table 13]

---------------------------
No. (Z) _q R ² R ³ R ⁶ Melting point (° C)
---------------------------
F-1-Me Me Me 103-107
---------------------------
[Table 14]

-----------------------
No. (Z) _m R ² R ³ Melting point (° C)
-----------------------
G-1 4-Cl Me Me 78-83
-----------------------
[Table 15]

----------------------------
No. (Z) _m R ² R ³ R ⁶ Melting point (℃)
----------------------------
H-1 4-Cl Me Me Me 99-103
H-2 4-Cl Me Et Me 58-61
----------------------------
[Table 16]

---------------------------
No. R ¹ R ² R ³ R ⁶ Melting point (℃)
---------------------------
P-1 cHex Me Et Me * 1
P-2 cHex Me cPr Me * 1
P-3 Me Me Et Me 56-61
---------------------------
Of the compounds of the present invention shown in Tables 1 to 16, ¹ H-NMR data of compounds having no melting point are shown in Table 17.

Moreover, the symbol in a table | surface represents the following meaning.
s: singlet, d: doublet, t: triplet, q: quartet, sept: septe, bs: broad singlet, m: multiplet.

The proton nuclear magnetic resonance chemical shift value was measured at 300 MHz in deuterated chloroform solvent using Me ₄ Si (tetramethylsilane) as a reference substance.
[Table 17]
------------------------------
No. ¹ H-NMR (CDCl ₃ , Me ₄ Si, 300 MHz)
------------------------------
A-8 δ7.85-7.76 (m, 2H), 7.68-7.60 (m, 1H),
7.56-7.42 (m, 3H), 7.10-7.00 (m, 2H),
5.31 (s, 2H), 3.70 (s, 3H),
3.52 (sept, 1H, J = 6.9Hz), 2.22 (s, 3H),
1.07 (d, 6H, J = 6.9Hz).
A-12 δ7.86-7.75 (m, 2H), 7.68-7.60 (m, 1H),
7.56-7.42 (m, 3H), 7.12-7.00 (m, 2H),
5.32 (s, 2H), 3.71 (s, 3H),
2.57 (t, 2H, J = 7.5Hz), 2.23 (s, 3H),
1.68-1.50 (m, 2H), 0.90 (t, 3H, J = 7.4Hz).
A-13 δ7.70-7.45 (m, 6H), 7.45-7.20 (m, 1H),
7.15-7.00 (m, 1H), 5.33 (s, 2H),
3.71 (s, 3H), 2.61 (q, 2H, J = 7.7Hz),
2.24 (s, 3H), 1.10 (t, 3H, J = 7.7Hz).
A-17 δ7.75-7.45 (m, 5H), 7.45-7.25 (m, 1H),
7.25-7.00 (m, 2H), 5.33 (s, 2H),
3.72 (s, 3H), 2.55 (q, 2H, J = 7.7Hz),
2.24 (d, 3H, J = 3.0Hz),
1.08 (t, 3H, J = 7.7Hz).
A-20 δ7.70-7.60 (m, 1H), 7.58-7.42 (m, 3H),
7.42-7.24 (m, 2H), 7.02-6.88 (m, 2H),
5.33 (s, 2H), 3.84 (s, 3H), 3.72 (s, 3H),
2.18 (s, 3H), 2.07 (s, 3H).
A-22 δ7.85-7.75 (m, 2H), 7.68-7.60 (m, 1H),
7.52-7.44 (m, 3H), 7.13-7.00 (m, 2H),
5.26 (s, 2H), 3.70 (s, 3H), 2.14 (s, 3H),
1.27 (s, 9H).
A-23 δ7.88-7.82 (m, 1H), 7.72-7.66 (m, 1H),
7.60-7.40 (m, 4H), 7.38-7.15 (m, 2H),
5.28 (s, 2H), 3.71 (s, 3H),
2.60-2.44 (m, 1H), 2.26 (s, 3H),
1.02-0.92 (m, 2H), 0.88-0.76 (m, 2H).
A-24 δ7.60-7.35 (m, 6H), 7.35-7.20 (m, 1H),
6.96-6.86 (m, 1H), 5.27 (s, 2H),
3.84 (s, 3H), 3.71 (s, 3H),
2.58-2.42 (m, 1H), 2.27 (s, 3H),
1.00-0.90 (m, 2H), 0.86-0.74 (m, 2H).
A-26 δ7.83-7.78 (m, 1H), 7.70-7.60 (m, 2H),
7.56-7.42 (m, 3H), 7.36-7.24 (m, 2H),
5.33 (s, 2H), 3.70 (s, 3H),
2.59 (q, 2H, J = 7.6Hz), 2.22 (s, 3H),
1.09 (t, 3H, J = 7.6Hz).
B-18 δ7.95-7.87 (m, 1H), 7.87-7.79 (m, 2H),
7.67-7.61 (m, 2H), 7.42-7.35 (m, 3H),
5.47 (s, 2H), 3.65 (s, 3H), 2.30 (s, 3H),
2.04 (s, 3H).
B-40 δ7.90-7.75 (m, 2H), 7.50-7.20 (m, 3H),
7.20-7.00 (m, 2H), 5.41 (s, 2H),
3.70 (s, 3H), 2.53 (s, 3H), 2.22 (s, 3H).
B-41 δ7.68-7.58 (m, 1H), 7.45-7.22 (m, 4H),
7.20-7.02 (m, 2H), 5.24 (s, 2H),
3.70 (s, 3H), 2.52 (s, 3H),
2.55-2.44 (m, 2H), 2.30 (d, 3H, J = 3.3Hz),
1.62-1.45 (m, 2H), 0.88 (t, 3H, J = 7.4Hz).
B-49 δ7.67-7.61 (m, 2H), 7.43-7.15 (m, 11H),
4.88 (s, 2H), 3.68 (s, 3H),
2.61 (q, 2H, J = 7.7Hz), 2.24 (s, 3H),
1.08 (t, 3H, J = 7.7Hz).
B-53 δ7.67-7.61 (m, 2H), 7.42-7.16 (m, 11H),
4.91 (s, 2H), 3.68 (s, 3H), 2.22 (s, 3H),
2.12 (s, 3H).
B-54 δ7.89-7.81 (m, 2H), 7.46-7.37 (m, 2H),
7.26-7.20 (m, 1H), 7.10-7.00 (m, 2H),
5.20 (s, 2H), 3.66 (s, 3H),
2.81 (q, 2H, J = 7.6Hz), 2.57-2.43 (m, 1H),
2.35 (s, 3H), 1.26 (t, 3H, J = 7.6Hz),
0.94-0.86 (m, 2H), 0.79-0.71 (m, 2H).
B-58 δ7.76-7.64 (m, 1H), 7.50-7.20 (m, 4H),
7.20-7.02 (m, 2H), 5.19 (s, 2H),
3.71 (s, 3H), 2.50-2.33 (m, 1H),
2.48 (s, 3H), 2.35 (d, 3H, J = 3.3Hz),
0.98-0.86 (m, 2H), 0.86-0.70 (m, 2H).
B-59 δ7.67-7.56 (m, 2H), 7.46-7.20 (m, 4H),
7.14-7.00 (m, 1H), 5.20 (s, 2H),
3.69 (s, 3H), 2.56-2.45 (m, 1H),
2.47 (s, 3H), 2.34 (s, 3H),
1.00-0.85 (m, 2H), 0.85-0.70 (m, 2H).
B-62 δ7.90-7.80 (m, 2H), 7.43-7.35 (m, 2H),
7.30-7.22 (m, 1H), 7.12-7.00 (m, 2H),
5.16 (s, 2H), 3.68 (s, 3H), 2.50 (s, 3H),
2.20 (s, 3H), 1.26 (s, 3H),
1.02-0.93 (m, 2H), 0.54-0.45 (m, 2H).
B-65 δ7.77-7.68 (m, 2H), 7.44-7.35 (m, 3H),
7.30-7.18 (m, 2H), 5.25 (s, 2H),
3.68 (s, 3H), 2.55 (q, 2H, J = 7.7Hz),
2.51 (s, 3H), 2.28 (s, 3H),
1.06 (t, 3H, J = 7.7Hz).
B-67 δ8.07 (s, 1H), 8.01 (d, 1H, J = 8.1Hz),
7.62 (d, 1H, J = 8.1Hz), 7.54-7.45 (m, 1H),
7.42-7.36 (m, 2H), 7.30-7.23 (m, 1H),
5.25 (s, 2H), 3.68 (s, 3H),
2.56 (q, 2H, J = 7.8Hz), 2.52 (s, 3H),
2.31 (s, 3H), 1.06 (t, 3H, J = 7.8Hz).
B-69 δ7.90-7.77 (m, 2H), 7.45-7.35 (m, 2H),
7.31-7.20 (m, 1H), 7.13-7.00 (m, 2H),
5.27-5.13 (m, 2H), 3.68 (s, 3H),
3.45-3.23 (m, 1H), 2.51 (s, 3H),
2.28 (s, 3H), 1.65-1.25 (m, 2H),
1.03 (d, 3H, J = 6.9Hz),
0.79 (t, 3H, J = 7.4Hz).
B-72 δ7.90-7.75 (m, 2H), 7.45-7.35 (m, 2H),
7.35-7.20 (m, 1H), 7.14-7.00 (m, 2H),
5.17 (s, 2H), 3.68 (s, 3H), 2.51 (s, 3H),
2.17 (s, 3H), 1.21 (s, 9H).
B-73 δ7.84-7.68 (m, 2H), 7.58 (bs, 1H),
7.47-7.36 (m, 2H), 7.35-7.23 (m, 1H),
7.15-7.02 (m, 2H), 5.21 (s, 2H),
3.69 (s, 3H), 2.50 (s, 3H), 2.39 (s, 3H),
1.38 (s, 6H).
B-74 δ7.90-7.85 (m, 1H), 7.80-7.66 (m, 1H),
7.46-7.20 (m, 5H), 5.19 (s, 2H),
3.69 (s, 3H), 2.56-2.40 (m, 1H),
2.47 (s, 3H), 2.33 (s, 3H),
0.98-0.86 (m, 2H), 0.86-0.72 (m, 2H).
B-78 δ7.81-7.72 (m, 2H), 7.45-7.34 (m, 2H),
7.30-7.24 (m, 1H), 7.08-6.98 (m, 2H),
5.39 (s, 2H), 4.30 (q, 2H, J = 7.2Hz),
3.70 (s, 3H), 2.52 (s, 3H), 2.31 (s, 3H),
1.31 (t, 3H, J = 7.2Hz).
B-81 δ8.10-8.06 (m, 1H), 7.88-7.80 (m, 1H),
7.70-7.63 (m, 1H), 7.42-7.36 (m, 3H),
7.29-7.23 (m, 1H), 5.25 (s, 2H),
4.01 (s, 3H), 3.68 (s, 3H),
2.54 (q, 2H, J = 7.7Hz), 2.52 (s, 3H),
2.36 (s, 3H), 2.25 (s, 3H),
1.06 (t, 3H, J = 7.7Hz).
B-84 δ7.47-7.35 (m, 4H), 7.34-7.28 (m, 1H),
7.28-7.20 (m, 1H), 7.00-6.88 (m, 1H),
5.19 (s, 2H), 3.85 (s, 3H), 3.69 (s, 3H),
2.55-2.40 (m, 1H), 2.47 (s, 3H),
2.33 (s, 3H), 0.96-0.84 (m, 2H),
0.82-0.68 (m, 2H).
B-86 δ7.41-7.35 (m, 2H), 7.29-7.21 (m, 1H),
7.12-7.01 (m, 3H), 5.23 (s, 2H),
3.68 (s, 3H), 2.52 (s, 3H),
2.48 (q, 2H, J = 7.6Hz), 2.34 (s, 3H),
2.32 (s, 3H), 2.19 (s, 3H),
1.03 (t, 3H, J = 7.6Hz).
B-87 δ7.42-7.33 (m, 2H), 7.27-7.20 (m, 1H),
7.15-7.00 (m, 3H), 5.17 (s, 2H),
3.69 (s, 3H), 2.47 (s, 3H),
2.42-2.30 (m, 1H), 2.38 (s, 3H),
2.33 (s, 3H), 2.24 (s, 3H),
0.92-0.83 (m, 2H), 0.75-0.65 (m, 2H).
B-99 δ7.82-7.78 (m, 1H), 7.70-7.65 (m, 1H),
7.53-7.43 (m, 1H), 7.38-7.20 (m, 4H),
5.41 (s, 2H), 3.68 (s, 3H),
2.51 (q, 2H, J = 7.8Hz), 2.27 (s, 3H),
1.00 (t, 3H, J = 7.8Hz).
B-104 δ8.05-7.99 (m, 1H), 7.80-7.72 (m, 1H),
7.53-7.46 (m, 1H), 7.44-7.34 (m, 2H),
7.30-7.20 (m, 2H), 5.19 (s, 2H),
3.68 (s, 3H), 2.55-2.42 (m, 1H),
2.46 (s, 3H), 2.32 (s, 3H),
0.96-0.85 (m, 2H), 0.85-0.74 (m, 2H).
B-106 δ8.40-8.37 (m, 1H), 8.09-8.04 (m, 1H),
7.99-7.93 (m, 1H), 7.52-7.44 (m, 1H),
7.42-7.36 (m, 2H), 7.30-7.24 (m, 1H),
5.26 (s, 2H), 3.68 (s, 3H), 2.64 (s, 3H),
2.56 (q, 2H, J = 7.6Hz), 2.52 (s, 3H),
2.33 (s, 3H), 1.07 (t, 3H, J = 7.6Hz).
B-109 δ7.65-7.55 (m, 1H), 7.50-7.34 (m, 4H),
7.34-7.20 (m, 1H), 7.00-6.88 (m, 1H),
5.44 (s, 2H), 3.84 (s, 3H), 3.67 (s, 3H),
2.52 (q, 2H, J = 7.8Hz), 2.29 (s, 3H),
1.03 (t, 3H, J = 7.8Hz).
E-8 δ8.48 (d, 1H, J = 2.3Hz),
7.79 (d, 1H, J = 2.3Hz), 7.46-7.36 (m, 2H),
7.32-7.24 (m, 1H), 5.25 (s, 2H),
3.71 (s, 3H), 3.43 (sept, 1H, J = 6.9Hz),
2.53 (s, 3H), 2.30 (s, 3H),
1.02 (d, 6H, J = 6.9Hz).
E-12 δ8.14-8.06 (m, 1H), 7.68-7.60 (m, 1H),
7.44-7.35 (m, 2H), 7.34-7.20 (m, 2H),
5.22 (s, 2H), 3.69 (s, 3H),
2.50-2.30 (m, 1H), 2.48 (s, 3H),
2.40 (s, 3H), 1.02-0.90 (m, 2H),
0.86-0.70 (m, 2H).
J-2 δ7.84-7.76 (m, 2H), 7.57-7.47 (m, 1H),
7.45-7.38 (m, 1H), 7.28-7.20 (m, 1H),
7.09-7.00 (m, 2H), 5.25 (s, 2H),
3.70 (s, 3H), 2.59 (q, 2H, J = 7.7Hz),
2.24 (s, 3H), 1.10 (t, 3H, J = 7.7Hz).
J-3 δ7.87-7.77 (m, 2H), 7.50-7.40 (m, 2H),
7.38-7.25 (m, 1H), 7.12-7.00 (m, 2H),
5.17 (s, 2H), 3.70 (s, 3H),
2.59 (q, 2H, J = 7.7Hz), 2.28 (s, 3H),
2.22 (s, 3H), 1.10 (t, 3H, J = 7.7Hz).
O-2 δ7.85 (d, 1H, J = 3.3Hz), 7.44-7.34 (m, 2H),
7.30 (d, 1H, J = 3.3Hz), 7.28-7.18 (m, 1H),
5.20 (s, 2H), 3.69 (s, 3H),
2.55-2.44 (m, 2H), 2.46 (s, 3H),
1.00-0.88 (m, 2H), 0.88-0.75 (m, 2H).
P-1 δ7.39-7.32 (m, 2H), 7.29-7.19 (m, 1H),
5.12 (s, 2H), 3.67 (s, 3H), 2.47 (s, 3H),
2.38 (q, 2H, J = 7.7Hz), 2.24-2.10 (m, 1H),
1.87-1.63 (m, 4H), 1.78 (s, 3H),
1.44-1.12 (m, 6H), 0.98 (t, 3H, J = 7.7Hz).
P-2 δ7.40-7.12 (m, 3H), 5.06 (s, 2H),
3.67 (s, 3H), 2.42 (s, 3H),
2.32-2.16 (m, 2H), 1.89-1.64 (m, 4H),
1.85 (s, 3H), 1.46-1.13 (m, 6H),
0.88-0.80 (m, 2H), 0.73-0.64 (m, 2H).
------------------------------
[Table 18]

---------------------------
No. (Z) _m R ² R ³ Melting point (° C)
---------------------------
a-1 4-F Me Me 192-194
a-2 4-CF ₃ Me Me 161-163
a-3 4-F Me Et 125-128
a-4 4-F Me iPr 156-161
a-5 2-F Me Me 134-136
a-6 2-Cl Me Me 165-167
a-7 3-OMe Me Me 113-115
a-8 2-OMe Me Me 142-145
a-9 4-F Me tBu 112-114
a-10 4-F Me H 179-181
a-11 2,4-di-F Me Me 154-156
a-12 2-Me Me Me 155-157
a-13 2,3-di-F Me Me 124-127
a-14 4-SMe Me Me 171-174
a-15 4-F Me CH ₂ OMe 124-126
a-16 2-F Me nPr 106-108
a-17 4-NO ₂ Me Me 210-213
a-18 4-Ph Me Me 203-206
a-19-Ph Et 100-101
a-20-Ph Me 107-108
a-21 2,5-di-F Me Et 110-111
a-22 4-CO ₂ Me Me Et 175-176
a-23 3-Cl-4-F Me Et 175-176
a-24 4-F Me U-1a 132-135
a-25 3-OCF ₃ Me Et 110-111
a-26 3-CF ₃ Me Et 135-137
a-27 4-F Me sBu 162-165
a-28 4-F Me CH ₂ OEt 111-113
a-29 4-F Me C (Me) ₂ OH 158-160
a-30 4-F Me U-2a 146-150
a-31 4-F Me U-2b 169-171
a-32 4-F Me U-2c 192-195
a-33 4-F Me CO ₂ Et 117-119
a-34 4-C (= NOMe) Me Me Et 109-111
a-35 4-tBu Me Et 184-186
a-36 2,5-di-Me Me Et 132-133
a-37 2,5-di-Me Me cPr 152-154
a-38 4-F Me CH ₂ OAc 142-145
a-39 3-Cl-4-F Me cPr 176-180
a-40 3,4-di-OMe Me Et 160-163
a-41 4-F Me C (OMe) ₂ Me 140-142
a-42 4-F Et Et 154-157
a-43 3-Ac Me Et 147-150
a-44-Me Me 127-129
a-45 4-Cl Me Me 167-169
a-46 4-OMe Me Me 157-159
a-47 4-Me Me Me 167-168
a-48 3-F Me Me 130-133
a-49 4-FH Me 169-171
a-50 4-F Et Me 149-150
a-51 4-F Me U-1b 134-138
a-52 4-F Me U-1c 130-132
a-53 4-Cl Me cPr 189-190
a-54 3-Br-4-F Me Et 150-152
---------------------------
[Table 19]

---------------------------
No. (Z) _n R ² R ³ Melting point (° C)
---------------------------
a-1 4-F Me Me 192-194
b-1 3,5-di-Cl Me Me 106-111
b-2 3,5-di-Cl Me Et 171-174
b-3 3,5-di-Cl Me nPr 130-133
b-4 6-Cl Me Me 209-211
b-5 6-Cl Me Et 201-203
b-6 3,5-di-Cl Me iPr 100-105
b-7-Me Et 125-126
b-8 6-Br Me Et 198-200
---------------------------
[Table 20]

---------------------------
No. (Z) _m R ² R ³ Melting point (° C)
---------------------------
c-1 6-Cl Me Et 186-188
c-2 6-Cl Me cPr 213-214
c-3-Me Et 140-142
---------------------------
[Table 21]

---------------------------
No. (Z) _m R ² R ³ Melting point (° C)
---------------------------
d-1-Me Et 149-152
---------------------------
[Table 22]

---------------------------
No. (Z) _p R ² R ³ Melting point (° C)
---------------------------
e-1 5-Cl Me Et 161-163
e-2-Me Et 120-122
e-3 5-Cl Me cPr 212-213
e-4 5-Me Me Et 138-141
---------------------------
[Table 23]

---------------------------
No. (Z) _p R ² R ³ Melting point (° C)
---------------------------
f-1-Me Et 127-131
---------------------------
[Table 24]

---------------------------
No. (Z) _r R ² R ³ Melting point (° C)
---------------------------
g-1-Me cPr 181-183
g-2 4-Me Me Et 190-192
---------------------------
[Table 25]

---------------------------
No. (Z) _q R ² R ³ Melting point (° C)
---------------------------
h-1-Me Me 191-192
---------------------------
[Table 26]

---------------------------
No. (Z) _m R ² R ³ Melting point (° C)
---------------------------
i-1 4-Cl Me Me 183-184
i-2 4-Cl Me Et 175-176
---------------------------
[Table 27]

---------------------------
No. R ¹ R ² R ³ Melting point (℃)
---------------------------
j-1 cHex Me Et 202-204
j-2 cHex Me cPr 100-102
---------------------------
[Test example]
Next, the usefulness of the compound of the present invention as a pest control agent will be specifically described in the following test examples, but the present invention is not limited to these.

  Preparation of the present compound emulsion; emulsified white sample of the present compound (Solpol (registered trademark) 3005XL (manufactured by Toho Chemical Industry): N-methylpyrrolidone: Solvesso (registered trademark) 200 (produced by ExxonMobil)) = 1: 5: 2 To give a 20% emulsion. This emulsion was subjected to the following Test Examples 1 to 7.

Test Example 1 Wheat Blight Control Effect Test 1.3 Into a 90 cm ³ plastic pot planted with wheat at the leaf stage (variety: Haruyutaka), 5 ml of a chemical solution prepared by diluting the compound emulsion of the present invention with water and 500 ppm was sprayed. Processed. One day after spraying, a conidial spore suspension of Wheat fungus (Septoria nodorum) was spray-inoculated on wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 6 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated according to the following formula.

Control value = [1- (treatment area lesion area ratio / non-treatment area lesion area ratio)] × 100
As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1 to A-6, A-7, A-8, A-10, A-14, A-16, A-17, A-18 to A-26, B-1 to B-7, B- 9, B-10, B-15 to B-43, B-45, B-46, B-48 to B-52, B-54 to B-59, B-61 to B-71, B-73, B-74, B-77, B-78, B-81, B-83 to B-87, B-90 to B-94, B-96, B-97, B-99, B-100, B- 102-B-106, B-108-B-110, C-1, C-2, D-1 to D-4, D-5, E-1 to E-7, E-8 to E-19, F-1, G-1, H-1, H-2, I-1 to I-3, J-2, J-3, K-1 to K-3, L-1, M-1 to M- 5, N-1, O-1 to O-3, P-1, P-2
Test Example 2 Wheat Red Rust Control Effect Test 1.3 In a 90 cm ³ plastic pot planted with wheat (variety: Norin 61) at the leaf stage, the compound emulsion of the present invention was diluted with water and 5 ml of a chemical solution prepared to 500 ppm was prepared. Scattered. One day after spraying, a spore suspension of wheat red rust fungus (Puccinia recondita) was spray-inoculated into wheat and placed in an inoculation box at a temperature of 20 ° C. and a humidity of 100% for 1 day. Thereafter, it was placed in an air-conditioned greenhouse (20 ° C.) and held for 8 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1.

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1 to A-6, A-7, A-8, A-10, A-14, A-16, A-17, A-18 to A-22, A-25, A-26, B- 1, B-2, B-4 to B-10, B-15 to B-36, B-38 to B-41, B-45, B-46, B-48, B-50 to B-52, B-54 to B-59, B-61 to B-71, B-74, B-81, B-83 to B-87, B-90 to B-94, B-102 to B-106, B- 108-B-110, C-1, C-2, D-1 to D-4, D-5, E-1 to E-7, E-8 to E-15, E-18, E-19, H-1, H-2, I-1 to I-3, J-1 to J-3, K-1 to K-3, M-1 to M-3, M-5, N-1, O- 1-O-3, P-1, P-2
Test Example 3 Wheat powdery mildew control effect test 1.3 In a 90 cm ³ plastic pot planted with wheat at the leaf stage (variety: Norin 61), the compound emulsion of the present invention was diluted with water, and a chemical solution prepared to 500 ppm was prepared. 5 ml sprayed. One day after spraying, wheat was placed in an air-conditioned greenhouse (20 ° C.), and wheat was inoculated with conidia of wheat powdery mildew (Blumeria graminis). Thereafter, it was held for 7 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1, A-2, A-4, A-6, A-7, A-8, A-10, A-14, A-16, A-17, A-18 to A-26, B- 1, B-2, B-4 to B-6, B-8 to B-10, B-15 to B-19, B-21 to B-31, B-33 to B-36, B-38, B-40 to B-42, B-45, B-46, B-48, B-50 to B-52, B-54 to B-59, B-61 to B-74, B-81 to B- 87, B-90 to B-93, B-96 to B-106, B-109, B-110, C-2, D-3, E-3 to E-7, E-8, E-9, E-11 to E-18, H-1, H-2, I-1 to I-3, J-3, K-2, M-1 to M-5, N-1, O-1 to O- 3, P-1, P-2,
Test Example 4 Cucumber Gray Mold Control Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, the compound emulsion of the present invention was diluted with water at the cotyledon stage, and 5 ml of a chemical solution prepared to 500 ppm was sprayed. After air drying, the treated leaves were cut out and placed in plastic containers. The conidial spore suspension of cucumber gray mold fungus (Botrytis cinerea) and the dissolved PDA medium were mixed at a ratio of 1: 1, and 30 μl of the treated leaves were inoculated dropwise. After inoculation, after placing it at 20 ° C. under high humidity for 3 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1.

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1 to A-3, A-5, A-6, A-7, A-8, A-10, A-14, A-16, A-17, A-18 to A-21, A- 23 to A-26, B-1, B-2, B-4 to B-10, B-15 to B-23, B-26 to B-36, B-38 to B-41, B-46, B-48, B-50 to B-52, B-54 to B-59, B-61 to B-74, B-81, B-83 to B-87, B-89, B-90, B- 93, B-97, B-99, B-100, B-102 to B-106, B-108 to B-110, C-1, D-1 to D-4, D-5, E-1, E-3, E-5 to E-7, E-8 to E-19, F-1, G-1, H-1, I-1 to I-3, J-3, K-1 to K- 3, L-1, M-1, M-3 to M-5, N-1, O-1 to O-3
Test Example 5 Cucumber Nucleus Disease Control Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and the compound emulsion of the present invention was diluted with water at the cotyledon stage and sprayed with 5 ml of a chemical solution prepared to 500 ppm. After air drying, it was put in a plastic container. A cucumber cotyledon of a cucumber treated with a drug was inoculated with a bacterial agar piece (diameter 5 mm) of cucumber sclerotia (Sclerotinia sclerotiorum) previously cultured in a PDA medium. After inoculation, the plastic container was covered with vinyl, humidified, and placed at 20 ° C. for 2 days. Then, the proportion of the lesions formed in the inoculated leaves was measured, and the control value was calculated from the same formula as in Test Example 1. .

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-2, A-4, A-8, A-16, A-17, A-18, A-20, A-21, A-24 to A-26, B-1, B-4 to B- 6, B-9, B-10, B-23, B-24, B-26 to B-30, B-40, B-45, B-46, B-48, B-50 to B-52, B-54, B-55, B-58, B-59, B-61 to B-65, B-67, B-68, B-73, B-74, B-81, B-83 to B- 87, B-89, B-90, B-93, B-99, B-103 to B-106, B-108 to B-110, D-2 to D-4, D-5, E-1, E-5 to E-7, E-8, E-11, E-12, E-14 to E-19, F-1, G-1, H-2, I-1 to I-3, J- 3, K-2, L-1, M-1, M-3, M-5, N-1, O-1 to O-3,
Test Example 6 Cucumber powdery mildew control effect test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, the compound emulsion of the present invention was diluted with water at the cotyledon stage, and 5 ml of a chemical solution prepared to 500 ppm was sprayed. . After air drying, the cucumber was placed in an air-conditioned greenhouse (20 ° C.) and sprayed with a conidial spore suspension of cucumber powdery mildew (Erysiphe polygoni). After 9 days, the ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1.

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1 to A-6, A-7, A-8, A-10 to A-14, A-16, A-17, A-18 to A-26, B-1, B-2, B- 4 to B-10, B-15 to B-36, B-38 to B-42, B-44 to B-46, B-48 to B-74, B-78, B-79, B-81 to B-87, B-89 to B-94, B-96, B-97, B-99 to B-106, B-108 to B-110, C-1, C-2, D-1 to D- 4, D-5, E-1 to E-7, E-8 to E-19, F-1, G-1, H-1, H-2, I-1 to I-3, J-1 J-3, K-1 to K-3, L-1, M-1 to M-5, N-1, O-1 to O-3, P-1, P-2
Test Example 7 Cucumber Anthracnose Control Effect Test Cucumber (variety: Sagamihanjiro) was planted in a 90 cm ³ plastic pot, and the compound emulsion of the present invention was diluted with water at the cotyledon stage and sprayed with 5 ml of a chemical solution prepared to 500 ppm. . One day after spraying, a conidial spore suspension of cucumber anthracnose fungus (Colletotrichum lagenarium) was spray-inoculated on cucumber and placed in an inoculation box at a temperature of 25 ° C. and a humidity of 100% for 2 days. Thereafter, it was placed in an air-conditioned greenhouse (23 ° C.) and held for 7 days. The ratio of the formed lesions to the inoculated leaves was measured, and the control value was calculated from the same calculation formula as in Test Example 1.

As a result, among the compounds tested, the following compounds showed a control value of 70% or more.
Compound of the present invention; A-1 to A-6, A-7, A-8, A-10 to A-17, A-18 to A-26, B-1 to B-10, B-15 to B-43, B- 45-B-59, B-61-B-74, B-78, B-81-B-87, B-89-B-94, B-97, B-99-B-106, B-108- B-110, C-1, C-2, D-1 to D-4, D-5, E-1 to E-7, E-8 to E-19, F-1, G-1, H- 1, H-2, I-1 to I-3, J-1 to J-3, K-1 to K-3, L-1, M-1 to M-5, N-1, O-1 to O-3, P-1, P-2

  The hydrazone derivative according to the present invention is an extremely useful compound that exhibits excellent pest control activity, particularly bactericidal activity, and has almost no adverse effect on non-target organisms such as mammals, fish and useful insects. .

Claims (5)

Formula (I):

[Wherein W represents an oxygen atom or a sulfur atom,
A represents an oxygen atom or a sulfur atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, (C ₁ -C ₆ ) alkenyl optionally substituted by R ^a , C ₁ -C ₆ alkoxy, phenyl, (Z) _m substituted phenyl, pyridin-2-yl, _(Z) is replaced by _n pyridine-2-yl, pyridin-3-yl, _(Z) pyridine substituted by _n-3-yl, pyridin-4-yl , _(Z) is replaced by _n pyridine-4-yl, thiophen-2-yl, _(Z) is replaced by _p thiophene-2-yl, thiophen-3-yl, thiophene substituted by _{(Z) p} 3-yl, thiazol-2-yl, _(Z) is replaced by _r thiazol-2-yl, thiazol-4-yl, _(Z) thiazol-4-y substituted by _r , Thiazol-5-yl, _(Z) is replaced by _r thiazol-5-yl, naphthalen-1-yl, _(Z) is replaced by _q the naphthalene-1-yl, naphthalene-2-yl or (Z) represents naphthalen-2-yl substituted by _q ,
R ² is a hydrogen _atom, C 1 -C ₆ alkyl, halo _(C 1 ~C ₆₎ ^alkyl, optionally substituted by ^{R b1} _(C 1 ~C _{6) alkyl,} C 1 -C ₆ alkoxy, _{C 1} -C _{6 alkylcarbonyl,} C 1 -C ₆ alkoxycarbonyl or phenyl,
R ³ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ cycloalkyl, halo _(C 1 ~C ₆₎ alkyl, optionally substituted by ^{R b} _(C 1 ~C ₆₎ alkyl, halo _(C 1 _{~C 6)} cycloalkyl, optionally substituted by ^{R b} _(C 1 ~C _{6) cycloalkyl,} C 1 -C _{6 alkenyl,} C 1 -C _{6 alkynyl,} C 1 -C ₆ alkoxycarbonyl, Represents phenyl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, oxetan-2-yl or tetrahydrofuran-2-yl;
R ⁴ and R ⁵ each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
R ⁶ , R ⁷ , R ⁸ and R ⁹ are each independently a hydrogen atom, halogen atom, nitro, cyano, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkenyl. C ₁ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl or C ₁ -C ₆ alkylsulfonyl,
R ¹⁰ represents a hydrogen atom or C ₁ -C ₆ alkyl,
Z is a halogen atom, nitro, cyano, carboxy, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, halo (C ₁ -C ₆ ) alkoxy, C ₁ -C _{6 alkylthio,} C 1 -C _{6 alkylsulfinyl,} C 1 -C _{6 alkylsulfonyl,} C 1 -C _{6 alkylcarbonyl,} C 1 -C _{6 alkoxycarbonyl,} C 1 -C _{6 alkylaminocarbonyl,} C 1 -C ₆ alkoxy _(C 1 ~C ₆₎ alkyl, -C (= ^NOR c) represents ^{R d} or phenyl,
m represents an integer of 2, 3, 4 or 5, n represents an integer of 2, 3 or 4, p represents an integer of 2 or 3, q is 2, 3, 4, 5, 6 Or when r represents an integer of 7 or r represents an integer of 2, each Z may be the same as or different from each other;
R ^a represents phenyl or phenyl substituted by (Z) _m ,
R ^b is hydroxy, C ₁ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylcarbonyloxy or (Z) _m Represents substituted phenyl,
R ^b1 is hydroxy, C ₁ -C ₆ cycloalkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C Represents phenyl substituted by ₆ alkylcarbonyloxy or (Z) _m ;
R ^c and R ^d each independently represent a hydrogen atom or C ₁ -C ₆ alkyl,
p represents an integer of 1, 2 or 3,
q represents an integer of 1, 2, 3, 4, 5, 6 or 7,
r represents an integer of 1 or 2,
m represents an integer of 1, 2, 3, 4 or 5;
n represents an integer of 1, 2, 3, or 4]. W represents an oxygen atom,
A represents an oxygen atom,
R ¹ is C ₁ -C ₆ alkyl, C ₁ -C ₆ cycloalkyl, (C ₁ -C ₆ ) alkenyl optionally substituted by R ^a , phenyl, (Z) _m substituted phenyl, pyridine- 2-yl, (Z) _n- substituted pyridin-2-yl, pyridin-3-yl, (Z) _n- substituted pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, (Z) represents thiophen-2-yl, thiophen-3-yl, thiazol-2-yl, substituted by _p , (Z) thiazol-2-yl or naphthalen-2-yl substituted by _r ;
R ² represents a hydrogen atom, C ₁ -C ₆ alkyl, (C ₁ -C ₆ ) alkyl or phenyl optionally substituted by R ^b1 ,
R ³ represents a hydrogen _atom, C 1 -C _{6 alkyl,} C 1 -C ₆ cycloalkyl, halo _(C 1 ~C ₆₎ alkyl, optionally substituted by ^{R b} _(C 1 ~C ₆₎ alkyl, halo _(C 1 _{~C 6)} cycloalkyl, _C 1 -C ₆ cycloalkyl optionally substituted by ^{R _b,} C 1 _{~C 6} alkoxycarbonyl, phenyl, pyridin-2-yl, pyridin-3-yl or pyridine - Represents 4-yl,
R ⁴ and R ⁵ represent a hydrogen atom,
R ⁶ represents a hydrogen atom, a halogen atom, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl or C ₁ -C ₆ alkylthio,
R ⁷ represents a hydrogen atom or a halogen atom,
R ⁸ and R ⁹ each independently represent a hydrogen atom, a halogen atom or C ₁ -C ₆ alkyl;
R ¹⁰ represents C ₁ -C ₆ alkyl,
Z is a halogen atom, nitro, cyano, carboxy, C ₁ -C ₆ alkyl, halo (C ₁ -C ₆ ) alkyl, C ₁ -C ₆ alkoxy, halo (C ₁ -C ₆ ) alkoxy, C ₁ -C ₆ represents _alkylthio, C 1 -C _{6 alkylcarbonyl,} C 1 -C _{6 alkoxycarbonyl,} C 1 -C ₆ alkylaminocarbonyl, -C a (= ^NOR c) ^{R d} or phenyl,
R ^a represents phenyl substituted by (Z) _m ,
R ^b is hydroxy, C ₁ -C ₆ cycloalkyl, C ₁ -C ₆ alkoxy, C ₁ -C ₆ alkylthio, C ₁ -C ₆ alkylsulfinyl, C ₁ -C ₆ alkylcarbonyloxy or (Z) _m Represents substituted phenyl,
R ^b1 represents C ₁ -C ₆ alkoxy;
R ^c and R ^d independently of one another represent C ₁ -C ₆ alkyl,
The hydrazone derivative or a salt thereof according to claim 1.   An agrochemical containing one or more selected from the hydrazone derivative according to claim 1 and a salt thereof as an active ingredient.   A bactericide containing one or more selected from the hydrazone derivative according to claim 1 and a salt thereof as an active ingredient.   An agricultural and horticultural fungicide containing, as an active ingredient, one or more selected from the hydrazone derivative according to claim 1 and a salt thereof.