JPH05294948A - N-@(3754/24)substituted benzyloxy)imine derivative, its production and agricultural and horticultural germicide - Google Patents

Abstract

PURPOSE:To provide the subject new compound useful as an agricultural and horticultural germicide. CONSTITUTION:A compound of formula I (R is a halogen, nitro, a lower alkyl, a lower alkoxy, etc.; R<1> is a lower alkyl; R<2> is a lower alkoxy, a mono (lower alkyl) amino, etc.; R<3> is a lower alkyl, phenyl, etc.; R<4> and R<5> are each a lower alkyl, phenyl, etc.; (CH2)n may be formed in combination of R<4> with R<5>; n is 4 to 6; X is O, S, CHR<8> or NR<9>; R<8> and R<9> are each H, a lower alkyl, phenyl, etc.; m is 0 to 4; p and q are each 0 to 2), e.g. methyl-2-[2(morpholinoethylideneaminoxymethyl)phenyl]-2-methoxyiminoac etate. The compound of formula I is obtained by reacting a compound of formula II (R<2>' is a lower alkoxy; Hal is a halogen) with a compound of formula III in the presence of a base or a silver compound in an inert solvent at -40 to 30 deg.C.

Description

Detailed Description of the Invention

[0001]

The present invention relates to the general formula (I)

[Chemical 12] [In the formula, R may be the same or different, and a halogen atom,
A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, m represents an integer of 0 to 4, R ¹ represents a lower alkyl group, R ² is a lower alkoxy group or —N (R ⁶ ) R ⁷ (in the formula, R ⁶ and R ⁷ may be the same or different, and is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxyalkyl group, a cyanoalkyl group. Group, cycloalkyl group, lower alkenyl group, lower alkynyl group, phenyl group or phenylalkyl group, and R ⁶ and R ⁷ may each represent an alkylene group which may be interrupted by an oxygen atom, a sulfur atom or a nitrogen atom. .)
R ³ is a lower alkyl group, a lower haloalkyl group,
Lower haloalkoxyalkyl group, lower alkoxyalkyl group, cycloalkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group , A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, A substituted phenylcarbonyl group having 1 to 5 substituents selected from a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. R ⁴ and R ⁵ may be the same or different and may be a lower alkyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a phenyl group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkyl group, A substituted phenyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, and p and q each represent an integer of 0 to 2 ,
R ⁴ and R ⁵ may also be taken together at adjacent substitution positions to represent a methylene group having 4 to 6 carbon atoms. X is O, S, CH—R ⁸ (wherein R ⁸ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, and may be a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group. , A lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a substituted phenyl group having 1 to 5 substituents selected from a lower haloalkylthio group, a phenylalkyl group or the same or different,
Halogen atom, nitro group, cyano group, lower alkyl group,
A substituted phenylalkyl group having 1 to 5 substituents selected from a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. ),

[Chemical 13] Or N—R ⁹ (in the formula, R ⁹ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, Lower haloalkoxy group,
A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower group A substituted phenylcarbonyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, a phenylalkyl group, which may be the same or different, and may be halogen. A substituted phenylalkyl group having 1 to 5 substituents selected from an atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. Alternatively, it represents a pyridyl group. ) Is shown. ] It is related with the N- (substituted benzyloxy) imine derivative represented by these or its salt, its manufacturing method, and an agricultural and horticultural fungicide.

[0002]

2. Description of the Related Art EPC Publication No. 460575, JP-A-3
-246268, EPC Publication Nos. 464,388 and 472300, the N- (substituted benzyloxy) of the present invention.
It has been disclosed that compounds similar to imine derivatives are useful as fungicides.

[0003]

DISCLOSURE OF INVENTION Problems to be Solved by the Invention As a result of intensive studies by the present inventors to create a novel fungicide for agricultural and horticultural use, the N- (substituted benzyloxy group represented by the general formula (I) of the present invention has been obtained. The present invention has been completed by finding that an imine derivative is a novel compound not described in the literature and its bactericidal activity is more remarkable than that of the compounds disclosed in the prior art. The N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention has E and Z isomers due to the double bond of carbon atom-nitrogen atom. It also includes E-form and Z-form and a mixture containing the E-form and Z-form at an arbitrary ratio.

[0004]

As a typical method for producing the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention, the following production methods are exemplified. it can.

[Chemical 14] [In the formula, R, R ¹ , R ² ′, R ² ″, R ³ , R ⁴ , R ⁵ ,
m, p, q, X and Hal are the same as above. ]

The N- (substituted benzyloxy) imine derivative represented by the general formula (I) including the general formula (I-1) and the general formula (I-2) is represented by the general formula (III). N- (substituted benzyloxy) represented by the general formula (I-1) by reacting a compound with a compound represented by the general formula (II) in the presence of a base or a silver compound and in the presence of an inert solvent.
An imine derivative, and the derivative (I-1) is reacted with an amine represented by the general formula (IV) in the presence of an inert solvent to form an N-represented by the general formula (I-2).
A (substituted benzyloxy) imine derivative can be produced.

1. General formula (III) + general formula (II) → general formula (I-1) As the inert solvent which can be used in this reaction, any inert solvent which does not significantly inhibit the progress of this reaction, for example, isopropanol, tert. -Alcohols such as butanol and diethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane,
Ethers such as monoglyme and diglyme, halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride and tetrachloroethane, aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene and toluene,
Examples thereof include nitriles such as acetonitrile, dimethylformamide, dimethylsulfoxide, water and the like, and these inert solvents can be used alone or in a mixture. When the two-phase reaction is carried out using a mixed solvent of water and an organic solvent, a phase transfer catalyst such as triethylbenzylammonium chloride or trioctylmethylammonium chloride can also be used.

As the base used in the present invention, an inorganic base or an organic base can be used. As the inorganic base,
For example, carbonates of alkali metal atoms or alkaline earth metal atoms such as sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, etc., alkali metal atoms or alkaline earth metal atoms such as sodium hydroxide, potassium hydroxide, calcium hydroxide, etc. Alkali metal hydrides such as hydroxide, lithium hydride and sodium hydride can be used, and examples of the organic base include alkoxides of alkali metal atoms such as sodium methoxide and potassium tert-butoxide, and diethylamine. , Triethylamine, pyridine, benzyltrimethylammonium hydroxide and the like can be used. As the silver compound, for example, silver oxide or the like can be used.

The amount of the base used may be appropriately selected from the equimolar to excess molar range with respect to the compound represented by the general formula (III). The reaction temperature may be selected from the range of -70 ° C to the boiling point range of the inert solvent used, and is preferably -40 ° C to 30 ° C. The reaction time varies depending on the reaction scale, reaction temperature, etc., but is generally within the range of several minutes to 48 hours. Since this reaction is an equimolar reaction, the compound represented by the general formula (III) and the compound represented by the general formula (II) may be used in equimolar amounts, but either of them may be used in excess. .. After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system by a conventional method, for example, by solvent extraction, and if necessary, purifying it by column chromatography, recrystallization and the like.

2. General formula (I-1) + general formula (IV) → general formula (I-2) Examples of the inert solvent usable in this reaction include methanol, ethanol, propanol and butanol. Alcohols, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and xylene, nitriles such as acetonitrile and benzonitrile, methyl cellosolve, diethyl ether and diglyme. , Ethers such as dioxane and tetrahydrofuran, dimethylformamide, dimethylacetamide, dimethylsulfoxide, water and the like can be used as an inert solvent, and these inert solvents should be used alone or in a mixture. You can also Since this reaction is an equimolar reaction, an N- (substituted benzyloxy) imine derivative represented by the general formula (I-1) and an amine represented by the general formula (IV) may be used in an equimolar amount. , Preferably of the general formula (I
It is preferable to use the amines represented by the general formula (IV) in excess with respect to the N- (substituted benzyloxy) imine derivative represented by -1).

The reaction temperature may be selected from the range of 0 ° C. to the boiling point range of the inert solvent used. The reaction time varies depending on the reaction scale, reaction temperature, etc., but is generally within the range of several minutes to 48 hours. After completion of the reaction, the desired product can be produced by isolating the desired product from the reaction system by a conventional method, for example, by solvent extraction, and if necessary, purifying it by column chromatography, recrystallization and the like. The general formula (II) and the general formula which are the raw material compounds of the production method of the present invention
The compound represented by (III) is, for example, EPC Publication No. 460.
575, JP-A-3-246268, EPC Publication No. 4
It can be produced by the production method described in No. 63488 and No. 472300.

N represented by the general formula (I) of the present invention will be described below.
First representative examples of-(substituted benzyloxy) imine derivatives
Although illustrated in the table, the present invention is not limited to the exemplified compounds. General formula (I)

[Chemical 15]

[Table 1]

[Table 2]

[Table 3]

[0012]

[Table 4]

[Table 5]

[Table 6]

[0013]

EXAMPLES Representative examples of the present invention will be shown below. Example 1 1-1. Methyl 2- (2-bromomethylphenyl)
Preparation of 2-methoxyiminoacetate

[Chemical 16] 5.34 g of 2-methylphenylglyoxylic acid methyl ester and 5.35 g of N- in 60 ml of carbon tetrachloride.
Bromosuccinimide and 0.05 g of azabisisobutyronitrile were added, and the mixture was heated under reflux for 3 hours to carry out a reaction. After completion of the reaction, the reaction solution was cooled to room temperature, the insoluble matter was filtered off, the solvent was concentrated, and the resulting residue was purified by silica gel dry column chromatography to obtain the desired product 6.83.
g was obtained. Physical properties Oily substance

1-2. Production of methyl 2- [2- (morpholinoethylideneaminooxymethyl) phenyl] -2-methoxyiminoacetate (Compound No1)

[Chemical 17] 0.72 g of 1-morpholinoacetaldoxime was dissolved in 15 ml of dimethylformamide, 0.33 g of potassium hydroxide powder was added to the solution, and the mixture was stirred at 0 ° C. for 10 minutes, and then methyl 2- (2-bromomethylphenyl)- 2-
Add 1.43 g of methoxyiminoacetate and add 6 at room temperature.
A time reaction was performed. After the reaction is complete, add 30 ml of ice water to the reaction mixture.
And extract the desired product with ethyl acetate, wash the extract with water, dry the organic layer over anhydrous magnesium sulfate, and concentrate the solvent under reduced pressure to purify the residue obtained by silica gel dry column chromatography. Target product 0.4 g
Got Physical properties mp91.4-92.3 ° C Yield 20.6
%

Example 2 N-methyl-2- [2- (morpholinoethylideneaminooxymethyl) phenyl]-
Production of 2-methoxyiminoacetic acid amide (Compound No2)

[Chemical 18] 0.4 g of methyl 2- [2- (morpholinoethylideneaminooxymethyl) phenyl] -2-methoxyiminoacetate was dissolved in 10 ml of methanol, and 3 ml of a 40% aqueous methylamine solution was added thereto, followed by 8 at room temperature. The reaction was carried out over time. After completion of the reaction, the solvent was distilled off under reduced pressure, and 100 ml of ethyl acetate and 50 ml of water were added to the obtained residue to extract the desired product. The extract was washed with water and the organic layer was dried over anhydrous magnesium sulfate. Was concentrated under reduced pressure and the resulting residue was purified by silica gel dry column chromatography to obtain 0.36 g of the desired product. Physical properties mp117-128.7 ° C Yield 90%

The N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention is useful as an agricultural and horticultural fungicide, for example, rice blast (Pyricularia oryza).
e), Rhizoctonia solani, Rice sesame leaf blight (Cochiobolus miyabeanus), Powdery mildew of various host plants such as barley and wheat (Erysiphe graminis), oat crown rust Disease (Puccinia cor
onata) and other plant rusts, tomato blight (Phytop
hthora infestans) and other plant diseases, and cucumber downy mildew (Pseudoperonospora cubensis).

The agricultural and horticultural fungicide of the present invention has a remarkable bactericidal effect against the above-mentioned diseases that damage paddy field crops, field crops, fruit trees, vegetables, other crops, flowers and the like. According to the time when the outbreak is predicted, before the occurrence of the disease or at the time when the outbreak is confirmed, paddy fields, fields, fruit trees,
The intended effect of the fungicide for agricultural and horticultural use of the present invention can be obtained by treating vegetables, other crops, paddy water such as flowers, foliage or soil.

When the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention is used as a fungicide for agricultural and horticultural use, it is formed into a convenient shape according to a conventional method for agricultural chemicals. It is generally used as a formulation. That is, the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention is blended with a suitable inert carrier or, if necessary, an auxiliary agent in a suitable ratio. And then dissolved, separated, suspended, mixed, impregnated, adsorbed or adhered, and formulated into an appropriate dosage form such as a suspension, emulsion, solution, wettable powder, granule, powder, tablet, etc. good.

The inert carrier which can be used in the present invention may be either solid or liquid, and examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust powder, Tobacco stem powder, walnut shell powder, bran, fibrin powder, residue after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay, etc.), talcs (eg talc, pyrophyllide) Etc.), silicas (for example, diatomaceous earth, silica sand, mica, white carbon [hydrogenated finely divided silicon, synthetic highly dispersed silicic acid also referred to as hydrous silicic acid, and some products include calcium silicate as a main component]), activated carbon, Sulfur powder, pumice stone, calcined diatomaceous earth, crushed brick, fly ash, sand, calcium carbonate, inorganic mineral powder such as calcium phosphate, ammonium sulfate,
Examples thereof include chemical fertilizers such as ammonium phosphate, ammonium nitrate, urea, ammonium chloride, and compost, which are used alone or in the form of a mixture of two or more kinds.

The material which can be used as a liquid carrier is selected from those having solvent ability per se, and those having no solvent ability but capable of dispersing the active ingredient compound with the aid of an auxiliary agent. The following carriers can be mentioned as typical examples, and these carriers are used alone or in the form of a mixture of two or more kinds, and for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol). -, Ethylene glycol, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (eg ethyl acetate, diisopropyl phthalate, dibutyl phthalate, diocluphthalate etc.), amides (eg dimethylformamide, diethylformamide, dimethylacetamide) Etc.), nitriles (for example, acetonitrile, etc.), dimethyl sulfoxides, and the like.

As the other auxiliary agents, there may be mentioned the following representative auxiliary agents. These auxiliary agents may be used depending on the purpose and may be used alone or in some cases in combination of two or more kinds of auxiliary agents. However, in some cases it is also possible to use no adjuvant at all.

Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, for example polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxy. Ethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Examples thereof include surfactants such as lignin sulfonate and higher alcohol sulfate. In addition, for the purpose of stabilizing the dispersion of active ingredient compounds, adhering and / or binding, auxiliary agents exemplified below can be used, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose. It is also possible to use auxiliary agents such as gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite and lignin sulfonate.

It is also possible to use the following auxiliaries for improving the flowability of the solid product, for example waxes, stearates, alkyl phosphates and the like. As a peptizer for a suspending product, an auxiliary agent such as a naphthalene sulfonic acid condensate or a condensed phosphate can be used. As the defoaming agent, for example, an auxiliary agent such as silicone oil can be used. The compounding ratio of the active ingredient compound can be adjusted as required. For example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 50% in the case of emulsion or wettable powder. Weight percent is suitable.

The agricultural and horticultural fungicide containing the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention as an active ingredient is used as it is for controlling various diseases, or appropriately with water or the like. The amount effective for disease control in a diluted or suspended form may be applied to a crop where the disease is predicted to occur or a place where the disease is not expected to be used. The amount of the agricultural or horticultural fungicide containing the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention as an active ingredient depends on various factors such as the purpose, the target disease and the growing condition of the crop. However, it varies depending on the disease occurrence tendency, weather, environmental conditions, dosage form, application method, application place, application time, etc.
It may be appropriately selected from the range of g to 1 kg according to the purpose. An agricultural and horticultural fungicide containing the N- (substituted benzyloxy) imine derivative represented by the general formula (I) of the present invention as an active ingredient is further used for controlling disease to be controlled, for expanding a suitable control period, or for reducing the dose. It is also possible to use it by mixing with other agricultural and horticultural fungicides for the purpose of measuring.

[0025]

[Prescription Examples and Test Examples] Typical prescription examples and test examples of the present invention are shown below, but the present invention is not limited thereto. In the prescription examples, “part” means “part by weight”.

Formulation Example 1 Compound of the present invention 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above components are uniformly mixed and dissolved to obtain an emulsion. Formulation Example 2 Compound of the present invention 3 parts Cray powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain a powder. Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts The above components are uniformly mixed, an appropriate amount of water is added and kneaded, granulated and dried to obtain granules. Formulation Example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.

Test Example 1 Control Test for Barley Powdery Mildew On a barley plant (2 leaf stage) planted in a pot, powdery mildew (Erysiphe)
graminis f. sp. ho-rdei) sprinkled with spores, and one day later, a drug solution containing the compound of the present invention as an active ingredient (20
(0 ppm) was sprinkled and left in a thermostatic chamber at 25 ° C. The lesion area was investigated one week after the inoculation, and the effect was judged by the following criteria in comparison with the untreated plot. A: Control value 100-95% B: Control value 94-80% C: Control value 79-60% D: Control value 59-0% The results are shown in Table 3.

[0028]

[Table 7]

[Table 8]

Test Example 2 Control test against cucumber downy mildew A 200 ppm chemical solution containing the compound of the present invention as an active ingredient was sprayed on potted cucumbers (two-leaf stage), and one day later, zoospores of downy mildew (Pseudoperonospora cubenois). The suspension was spray inoculated. After inoculation, leave it in a humid chamber at 25 ° C for 1 day and leave it in a greenhouse for 6 days to allow sufficient disease to be caused, and then investigate the degree of lesions on each leaf,
The judgment was made according to the same criteria as in Test Example 1. The results are shown in Table 4.

[Table 9]

Test Example 3 Rice blast control test by spraying Rice plant (variety: Nipponbare, 5 leaf stage, 10 plants) planted in a biscuit pot with a diameter of 9 cm contains the compound of the present invention as an active ingredient 20
Spray 0ppm chemical solution thoroughly with a spray gun and spray 1
After a day, spray inoculate a spore suspension of rice blast fungus (Pyricularia oryzae), leave it in a moist chamber for 20 hours, and then move it to a greenhouse. After 6 days from the inoculation, the number of lesions was investigated, and it was controlled in comparison with the untreated plot. The value was calculated, and the judgment was made according to the same criteria as in Test Example 1.
The results are shown in Table 5.

[Table 10]

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location A01N 43/84 102 8930-4H C07D 211/14 9165-4C 241/04 8615-4C 265/30 279 / 12 491/113 7019-4C

Claims (4)

[Claims] 1. A compound represented by the general formula (I): [In the formula, R may be the same or different, and a halogen atom,
A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, m represents an integer of 0 to 4, R ¹ represents a lower alkyl group, R ² is a lower alkoxy group or —N (R ⁶ ) R ⁷ (in the formula, R ⁶ and R ⁷ may be the same or different, and is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxyalkyl group, a cyanoalkyl group. Group, cycloalkyl group, lower alkenyl group, lower alkynyl group, phenyl group or phenylalkyl group, and R ⁶ and R ⁷ may each represent an alkylene group which may be interrupted by an oxygen atom, a sulfur atom or a nitrogen atom. .)
R ³ is a lower alkyl group, a lower haloalkyl group,
Lower haloalkoxyalkyl group, lower alkoxyalkyl group, cycloalkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group , A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, A substituted phenylcarbonyl group having 1 to 5 substituents selected from a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. R ⁴ and R ⁵ may be the same or different and may be a lower alkyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a phenyl group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkyl group, A substituted phenyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, and p and q each represent an integer of 0 to 2 ,
R ⁴ and R ⁵ may also be taken together at adjacent substitution positions to represent a methylene group having 4 to 6 carbon atoms. X is O, S, CH—R ⁸ (wherein R ⁸ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, and may be a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group. , A lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a substituted phenyl group having 1 to 5 substituents selected from a lower haloalkylthio group, a phenylalkyl group or the same or different,
Halogen atom, nitro group, cyano group, lower alkyl group,
A substituted phenylalkyl group having 1 to 5 substituents selected from a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. ), [Chemical formula 2] Or N—R ⁹ (in the formula, R ⁹ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, Lower haloalkoxy group,
A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower group A substituted phenylcarbonyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, a phenylalkyl group, which may be the same or different, and may be halogen. A substituted phenylalkyl group having 1 to 5 substituents selected from an atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. Alternatively, it represents a pyridyl group. ) Is shown. ] The N- (substituted benzyloxy) imine derivative represented by these, or its salt. 2. A compound represented by the general formula (III): [In the formula, R may be the same or different, and a halogen atom,
A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, m represents an integer of 0 to 4, R ¹ represents a lower alkyl group, R ² 'represents a lower alkoxy group and Hal represents a halogen atom. ]
And a compound represented by the general formula (II): [Wherein R ³ is a lower alkyl group, a lower haloalkyl group,
Lower haloalkoxyalkyl group, lower alkoxyalkyl group, cycloalkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group , A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, A substituted phenylcarbonyl group having 1 to 5 substituents selected from a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. R ⁴ and R ⁵ may be the same or different and may be a lower alkyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a phenyl group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkyl group, A substituted phenyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, and p and q each represent an integer of 0 to 2 ,
R ⁴ and R ⁵ may also be taken together at adjacent substitution positions to represent a methylene group having 4 to 6 carbon atoms. X is O, S, CH—R ⁸ (wherein R ⁸ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, and may be a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group. , A lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a substituted phenyl group having 1 to 5 substituents selected from a lower haloalkylthio group, a phenylalkyl group or the same or different,
Halogen atom, nitro group, cyano group, lower alkyl group,
A substituted phenylalkyl group having 1 to 5 substituents selected from a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. ), [Chemical 5] Or N—R ⁹ (in the formula, R ⁹ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, Lower haloalkoxy group,
A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower group A substituted phenylcarbonyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, a phenylalkyl group, which may be the same or different, and may be halogen. A substituted phenylalkyl group having 1 to 5 substituents selected from an atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. Alternatively, it represents a pyridyl group. ) Is shown. ] The compound of the general formula (I-1) characterized by reacting with a compound represented by (In the formula, R, R ¹ , R ² ′, R ³ , R ⁴ , R ⁵ p, q and X are the same as above.) A method for producing an N- (substituted benzyloxy) imine derivative. 3. A compound represented by the general formula (I-1): [In the formula, R may be the same or different, and a halogen atom,
A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, m represents an integer of 0 to 4, R ¹ represents a lower alkyl group, R ² 'represents a lower alkoxy group, R ³ represents a lower alkyl group, a lower haloalkyl group, a lower haloalkoxyalkyl group, a lower alkoxyalkyl group, a cycloalkyl group, a phenyl group, which may be the same or different, a halogen atom, a nitro group. Group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group, lower alkylthio group or substituted phenyl group having 1 to 5 substituents selected from the same or different. May be a halogen atom, nitro group, cyano group, lower alkyl group, lower halo group. Kill group, a lower alkoxy group, lower haloalkoxy group, a substituted phenylcarbonyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group. R ⁴ and R ⁵ may be the same or different and may be a lower alkyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a phenyl group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkyl group, A substituted phenyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, and p and q are 0 to 2
And R ⁴ and R ⁵ may be combined at adjacent substitution positions to represent a methylene group having 4 to 6 carbon atoms. X is O, S, CH—R ⁸ (wherein R ⁸ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, and may be a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group. , A lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a substituted phenyl group having 1 to 5 substituents selected from a lower haloalkylthio group, a phenylalkyl group or the same or different, a halogen atom, a nitro group. A substituted phenylalkyl group having 1 to 5 substituents selected from a group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. ), Or N—R ⁹ (in the formula, R ⁹ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, Lower haloalkoxy group,
A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower group A substituted phenylcarbonyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, a phenylalkyl group, which may be the same or different, and may be halogen. A substituted phenylalkyl group having 1 to 5 substituents selected from an atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. Alternatively, it represents a pyridyl group. ) Is shown. ] An N- (substituted benzyloxy) imine derivative represented by the following general formula (IV) R ² ″ H (IV) [in the formula, R ² ″ is —N (R ⁶ ) R ⁷ (in the formula, R ⁶ and R ⁷ may be the same or different and each is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxyalkyl group, a cyanoalkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, a phenyl group or a phenylalkyl group. R ⁶ and R ⁷ may each represent an alkylene group which may be interrupted by an oxygen atom, a sulfur atom or a nitrogen atom.)
Show. ] The compound represented by the general formula (I-2): [Wherein R, R ¹ , R ² ″, R ³ , R ⁴ , R ⁵ m, p,
q and X are the same as above. ] The manufacturing method of the N- (substituted benzyloxy) imine derivative represented by these. 4. A compound represented by the general formula (I): [In the formula, R may be the same or different, and a halogen atom,
A nitro group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, m represents an integer of 0 to 4, R ¹ represents a lower alkyl group, R ² is a lower alkoxy group or —N (R ⁶ ) R ⁷ (in the formula, R ⁶ and R ⁷ may be the same or different, and is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxyalkyl group, a cyanoalkyl group. Group, cycloalkyl group, lower alkenyl group, lower alkynyl group, phenyl group or phenylalkyl group, and R ⁶ and R ⁷ may each represent an alkylene group which may be interrupted by an oxygen atom, a sulfur atom or a nitrogen atom. .)
R ³ is a lower alkyl group, a lower haloalkyl group,
Lower haloalkoxyalkyl group, lower alkoxyalkyl group, cycloalkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, lower alkyl group, lower haloalkyl group, lower alkoxy group, lower haloalkoxy group , A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, A substituted phenylcarbonyl group having 1 to 5 substituents selected from a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. R ⁴ and R ⁵ may be the same or different and may be a lower alkyl group, a lower haloalkyl group, a lower alkoxyalkyl group, a phenyl group or the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower alkyl group, A substituted phenyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, and p and q each represent an integer of 0 to 2 ,
R ⁴ and R ⁵ may also be taken together at adjacent substitution positions to represent a methylene group having 4 to 6 carbon atoms. X is O, S, CH—R ⁸ (wherein R ⁸ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, and may be a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group. , A lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a substituted phenyl group having 1 to 5 substituents selected from a lower haloalkylthio group, a phenylalkyl group or the same or different,
Halogen atom, nitro group, cyano group, lower alkyl group,
A substituted phenylalkyl group having 1 to 5 substituents selected from a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group is shown. ), Or N—R ⁹ (in the formula, R ⁹ may be a hydrogen atom, a lower alkyl group, a phenyl group, the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, Lower haloalkoxy group,
A substituted phenyl group having 1 to 5 substituents selected from a lower alkylthio group or a lower haloalkylthio group, a phenylcarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a lower alkyl group, a lower group A substituted phenylcarbonyl group having 1 to 5 substituents selected from a haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group, a phenylalkyl group, which may be the same or different, and may be halogen. A substituted phenylalkyl group having 1 to 5 substituents selected from an atom, a nitro group, a cyano group, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group or a lower haloalkylthio group. Alternatively, it represents a pyridyl group. ) Is shown. ] The N- (substituted benzyloxy) imine derivative represented by these or its salt is contained as an active ingredient, The fungicide for agricultural and horticultural use characterized by the above-mentioned.