JPH09176100A - N-[(fluoroalkoxy) phenoxyalkyl] benzamide compounds, intermediates, processes for their production, and pest control agents for agriculture and horticulture - Google Patents

Abstract

(57) [Abstract] [Problem] N-, which is useful as a nematicide, acaricide, and a fungicide
Provided are [(fluoroalkoxy) phenoxyalkyl] benzamide derivatives. The N-[(fluoroalkoxy) of the present invention
The phenoxyalkyl] benzamide compound has the following formula (1): (In the formula, R ¹ and R ³ may be the same or different, a hydrogen atom, a halogen atom, a C1-4 alkyl group, C1-4
Represents an alkoxy group, C1-4 haloalkyl group, C1-4 haloalkoxy group, cyano group, nitro group, hydroxyl group; R
² is a hydrogen atom, a halogen atom, a C1-4 alkyl group,
A represents a C1-4 alkoxy group; A represents an oxygen atom and a sulfur atom; x is 1 to 4, y is 0 to 6, z is 2 to 9 and m is 0.
Represents an integer of ２2. However, 2x + 1 = y + z + m. ).

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound which is a pesticide for agricultural and horticultural use, which is useful as a nematicide, acaricide, fungicide and the like. It is about.

[0002]

2. Description of the Related Art As the benzamide compounds similar to the target compound of the present invention, the following (1) and (2) are known. (1) JP-A-1-105784 discloses the following formula:

[0003]

[Chemical 6]

(Wherein R and R ¹ represent a hydrogen atom, a halogen atom, a nitro group, an alkyl group, an allyl group, a cycloalkyl group, an alkoxy group, an allyloxy group; Z is
Represents an alkylene having 2 to 4 carbon atoms. Note that R, R ¹ and Z defined by this formula are limited to this formula only. )
It is described that the compounds represented by are effective as photographic materials. (2) Japanese Patent Application Laid-Open No. 1-151546 discloses the following formula:

[0005]

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(Where X is O, S or NOH, and R is
¹ is H or CH ₃ , n is 1, 2 or 3, R
² , R ³ and R ⁴ are the following paragraphs: a) R ² and R ³ are individually Cl or Br and R ⁴ is H: b) R ² , R ³ and R ⁴ are individually Cl or Br Br: c) R ² is F, R ³ is Cl, R ⁴ is H: or d) R ² and R ³ are CH ₃ or C ₂ H ₅ , R ⁴ is H Is defined by one of

R ⁵ , R ⁶ and R ⁷ are the following paragraphs: a) one of R ⁶ and R ⁷ is CF ₃ and the other of R ⁵ and R ⁶ and R ⁷ is H: b) R ⁵ And R ⁶ is H and R ⁷ is F, Cl or Br.
C) R ⁵ and R ⁷ are independently F, Cl or Br, and R
⁶ is H: d) R ⁵ and R ⁶ are individually F, Cl or Br, R
⁷ is H: e) R ⁶ and R ⁷ are individually F, Cl or Br, R
⁵ is H: or f) R ⁶ is phenoxy and R ⁵ and R ⁷ are defined as either H. Note that R ¹ defined by this formula
~ R ⁷ , n and X are limited to this formula only. It is described that the compound represented by the formula (1) is effective as a fungicide.

The following (3) to (6) are known as (fluoroalkoxy) phenoxyalkylamine compounds similar to the starting material compounds of the present invention. (3) Japanese Patent Application Laid-Open No. 61-44846 discloses the following formula:

[0009]

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[Wherein, m and m ′ are each independently 0 or 1; n is an integer of 0 to 3; R is C;
1-4 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, C2-8 haloalkynyl, C2-10 alkoxyalkyl, C2-10 alkylthioalkyl, C3-8 cycloalkyl, C3-8 halocycloalkyl, C4-1
2 cycloalkylalkyl, heterocycloalkyl or heterocycloalkylalkyl; R ^{1 to} R ⁴ and R ⁸ are each independently hydrogen or C 1-8 alkyl; R ⁷ is C 1-8 alkyl, C 2-8 alkenyl , C
2-8 alkynyl, C1-8 haloalkyl, C2-8 haloalkenyl, C2-8 haloalkynyl, C3-8 cycloalkyl, C4-12 cycloalkylalkyl or phenyl, which is unsubstituted or of a ring carbon atom. 1,
2 or 3 position is C1-8 alkyl, C1-8 haloalkyl, C1-8 alkoxy, C1-8 haloalkoxy,
Halogen, nitro, phenyl which is substituted by a group selected from cyano and C1~8 alkylthio, provided that when X ¹ is NR ⁹ may, R ⁷ is also substituted or unsubstituted phenylthio and S-C ( SH ₃₎ can be selected from ₂ -CN group; R ⁹ is hydrogen atom or selected from the definition of R ^7; W is oxygen, sulfur, NR ^8,
CR ³ R ⁴ or carbonyl; W ¹ is oxygen, sulfur, NR ⁸ , CR ³ R ⁴ , carbonyl, sulfinyl or sulfonyl; X and Y are oxygen, sulfur or NR ⁸ respectively; X ¹ Is oxygen, sulfur or NR ⁹ ; Z is C 1-8 alkyl, C 1-8 haloalkyl or halogen. In addition, m, m ′ defined by this equation,
n, R, R ^{1 to} R ⁹ , W, W ¹ , X, X ¹ , Y and Z
Is limited to this expression only. ] It is described that the compound shown by these is effective as an insecticide.

(4) Japanese Unexamined Patent Publication No. 61-68470 discloses that
The following formula:

[0012]

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(Wherein R ¹ represents a lower alkyl group, a lower alkoxy-lower alkyl group or a cycloalkyl group having 3 to 8 carbon atoms; R ² represents a fluoro-substituted lower alkyl group; X represents an oxygen atom) Or a sulfur atom; Y is a halogen atom or a lower alkyl group; m is 0, 1 or 2
Is shown; n is an integer of 2 to 6. Note that R ¹ , R ² , X, Y, m and n defined by this formula are limited to this formula only. ] It is described that the compound shown by these is effective as a fungicide. (5) Japanese Patent Laid-Open No. 62-149659 discloses the following formula:

[0014]

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[Wherein R ¹ and R ² represent the same or different lower alkyl groups; R ³ and R ⁴ represent the same or different lower alkyl groups; R ⁵ and R ⁶ represent the same or different , Hydrogen atom, nitro group, cyano group, halogeno lower alkyl group, lower alkenyl group, hydroxyl group, halogeno lower alkoxy group, lower alkenyloxy group, aralkyloxy group, aralkenyloxy group, carboxy group, lower alkoxycarbonyl group, next formula:

[0016]

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[0017] (wherein, R ¹⁰ and R ¹¹ are the same or different, represent a hydrogen atom or a lower alkyl group. However, R ¹⁰
And R ¹¹ may combine with an adjacent nitrogen atom to form a pyrrolidine ring, a piperidine ring, a morpholine ring, or a piperazine ring in which the nitrogen atom at the 4-position may be substituted with a lower alkyl group. ), The following formula:

[0018]

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(Wherein R ¹⁰ and R ¹¹ are as defined above); R ⁷ and R ⁸ are the same or different and each is a hydrogen atom, a halogen atom, a cyano group or a lower alkyl group. Group, a hydroxyl group, a lower alkoxy group, a lower alkanoylamino group, or a naphthyl group which is integrated with a benzene ring when adjacent to each other; A ₁ represents an alkylene group, an alkenylene group, or an alkynylene group; and R ⁹ represents hydrogen. Represents an atom or a lower alkyl group; B represents a single bond or CH ₂ O; n represents 0, 1 or 2. However, R ⁵ and R
^{When 6} is the same or different and is a hydrogen atom or a nitro group, R ⁹ represents a lower alkyl group or A ₁ represents a branched alkylene group, alkenylene group or branched alkynylene group. In addition, R ^{1 to} R ¹¹ defined by this formula,
A ₁ , B, m and n are limited to this equation only. ] It is described that the compound represented by the above [] has a calcium antagonism and a sympathetic nerve β receptor blocker. (6) JP-A-2-142772 discloses the following formula:

[0020]

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[Wherein Ar represents an unsubstituted or one or more halogen, C1-3 alkyl, C1-3 haloalkyl, C
2-4 alkenyl, C2-4 haloalkenyl, C1-3
Represents a phenyl group having alkoxy or C1-4 haloalkoxy as a substituent, unsubstituted or a pyridyl group having one or more halogen or C1-3 haloalkyl as a substituent; K, X and Z independently of each other, O
Or S represents; B ₁ and B ₂ are the same or different and are C
1-6 alkylidene; Rh ₁ is C1-6 haloalkyl having 1-9 halogen atoms, C1-6 haloalkenyl having 1-9 halogen atoms, C3-8 haloalkoxyalkyl, C3-8 haloalkoxy. Represents alkenyl (halogen is preferably fluorine); A
Represents a heterocycle described in Table 1 (wherein R ^{1 to} R ^1
3 may be the same or different, H, C1-6 alkyl, C1-6 haloalkyl, C2-6 alkenyl, C2
~ 6 haloalkenyl, C2-6 alkynyl, C2-6 haloalkynyl; G represents CH or N. ). In addition, Ar, K, X, Z, B ₁ , B ₂ , defined by this equation,
Rh ₁ , A, R ^{1 to} R ³ and G are limited to this formula only. ] It is described that the compound shown by these is effective as a fungicide.

[0022]

[Table 1]

However, the disclosure of N-[(fluoroalkoxy) phenoxyalkyl] benzamide compounds and (fluoroalkoxy) phenoxyalkylamine compounds in which the amine moiety is a (fluoroalkoxy) phenoxyalkylamino group as in the present invention is not recognized. .
Therefore, the N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound and the (fluoroalkoxy) phenoxyalkylamine compound of the present invention are novel compounds, and the N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound is a nematicide. It is not known that it has pest control activity for agricultural and horticultural use which is useful as an acaricide or fungicide.

[0024]

The object of the present invention is to provide a novel N-[(fluoroalkoxy) phenoxyalkyl].
It is an object of the present invention to provide a pesticide for agricultural and horticultural use, which contains a benzamide compound as an active ingredient and is useful as a nematicide, acaricide or fungicide.

[0025]

DISCLOSURE OF THE INVENTION As a result of studies to solve the above problems, the present inventors have found that a novel N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound is a nematicide or acaricide. The present invention has been completed by finding that it has a remarkable controlling activity as a pest control agent for agricultural and horticultural use which is useful as a bactericide and the like. That is, the present invention is as follows. According to a first aspect, the following formula (1):

[0026]

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N-[(fluoroalkoxy) represented by
It relates to a phenoxyalkyl] benzamide compound. Note that R ^{1 to} R ³ , A, n, x, y, z in the formula
And n are as follows. R ¹ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom
~ 4 alkoxy group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, cyano group,
Represents a nitro group or a hydroxyl group. R ² represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms.

R ³ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a group having 1 to 4 carbon atoms. Represents a haloalkoxy group, a cyano group, or a nitro group. A represents an oxygen atom or a sulfur atom. n is 1
Represents an integer of from 6 to 6. x represents an integer of 1 to 4. y is
It represents an integer of 0 to 6. z represents an integer of 2 to 9. m
Represents an integer of 0 to 2. However, 2x + 1 = y + z +
m. The second invention provides the following formula (2):

[0029]

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(Wherein, n, x, y, z and m have the same meanings as defined above) and a (fluoroalkoxy) phenoxyalkylamine compound represented by the following formula (3):

[0031]

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(Wherein R ^{1 to} R ³ have the same meanings as described above, L ¹ represents a halogen atom or a hydroxyl group), and the above-mentioned carboxylic acid compound is reacted. In the formula (1), N- in which A is an oxygen atom
The present invention relates to a method for producing a [(fluoroalkoxy) phenoxyalkyl] benzamide compound. The third invention provides the following formula (2):

[0033]

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(Wherein n, x, y, z and m have the same meanings as defined above) and relates to a (fluoroalkoxy) phenoxyalkylamine compound. 4th
The invention of is represented by the following formula (4):

[0035]

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(In the formula, L ² represents a halogen atom, a methanesulfonyloxy group or a toluenesulfonyloxy group. N, x, y, z and m have the same meanings as described above.)
Wherein the (fluoroalkoxy) phenoxyalkyl compound represented by the formula is aminated.
The present invention relates to a method for producing a (fluoroalkoxy) phenoxyalkylamine compound represented by A fifth invention relates to a pesticide for agricultural and horticultural use, which comprises an N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound represented by the above formula (1) as an active ingredient.

[0037]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below. A novel N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound [compound (1)], which is a target compound, and R ^{1 to} R ³ , A, which are represented by the starting materials [compound (2) to compound (5)], x, y, z, m,
n, L ¹ and L ² and L ³ in the following formula (6) are as follows.

[R ¹ ] R ¹ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom.
~ 4 alkoxy group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, cyano group,
A nitro group and a hydroxyl group can be mentioned. Examples of the halogen atom include a chlorine atom, an iodine atom, a bromine atom, a fluorine atom and the like; a fluorine atom, a chlorine atom and a bromine atom are preferable. Examples of the alkyl group include linear and branched ones; a methyl group is preferable. Examples of the alkoxy group include linear and branched ones; a methoxy group is preferable.

Examples of the haloalkyl group include linear or branched ones; examples of the halogen atom include chlorine atom, iodine atom, bromine atom, and fluorine atom, but fluorine atom is preferable. The alkyl moiety is preferably methyl. The haloalkyl group is preferably CF ₃ . Examples of the haloalkoxy group include linear or branched ones; examples of the halogen atom include chlorine atom, iodine atom, bromine atom and fluorine atom, and preferably fluorine atom; alkyl The moiety is preferably methyl. The haloalkoxy group is preferably CHF ₂ O or CF ₃ O.

[R ² ] R ² is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom.
To 4 alkoxy groups can be mentioned. Examples of the halogen atom include a chlorine atom, an iodine atom, a bromine atom and a fluorine atom; a fluorine atom is preferable.
Examples of the alkyl group include linear and branched ones; a methyl group is preferable. Examples of the alkoxy group include linear and branched ones; a methoxy group is preferable.

[R ³ ] R ³ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, or 1 carbon atom.
~ 4 alkoxy group, haloalkyl group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 4 carbon atoms, cyano group,
A nitro group can be mentioned. Examples of the halogen atom include chlorine atom, iodine atom, bromine atom, and fluorine atom. As the alkyl group, a linear or branched one can be mentioned. As the alkoxy group, a linear or branched one can be mentioned.

Examples of the haloalkyl group include linear or branched ones; examples of the halogen atom include chlorine atom, iodine atom, bromine atom, and fluorine atom, but fluorine atom is preferable. The alkyl moiety is preferably methyl. The haloalkyl group is preferably CF ₃ . Examples of the haloalkoxy group include linear or branched ones; examples of the halogen atom include chlorine atom, iodine atom, bromine atom and fluorine atom, and preferably fluorine atom; alkyl The moiety is preferably methyl. The haloalkoxy group is preferably CF ₃ O. The substitution position of R ³ is not particularly limited; it is preferably the 4-position.

[OC _x H _y F _z Cl _m ] x is 1 to 4,
Preferably it is an integer of 1-3. y is an integer of 0 to 6, preferably 0 to 4. z is 2 to 9, preferably 2
6 to an integer. m is an integer of 0-2. However, 2x + 1 = y + z + m. OC _x H _y F _z Cl
The substitution position of _m is not particularly limited; preferably 3
4th and 4th. [A] Examples of A include an oxygen atom and a sulfur atom. [N] n is an integer of 1 to 6, preferably 2 to 5, and more preferably 2 or 3.

Examples of [L ^{1 to} L ³ ] L ¹ include a halogen atom and a hydroxyl group; the halogen atom is preferably a chlorine atom or a bromine atom. L ² and L
Examples of ³ include a halogen atom, a methanesulfonyloxy group, and a toluenesulfonyloxy group;
The halogen atom is preferably a chlorine atom or a bromine atom. As the compound (1), compounds obtained by combining the above-mentioned various substituents can be mentioned, and preferable compounds from the viewpoint of drug efficacy are as follows.

(A) R ^{1 to} R ³ are hydrogen atoms, and OC _x
H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z, A is an oxygen atom, and n is 2 (1). (b) R ¹ is a halogen atom, R ² and R ³ are hydrogen atoms, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z , and A is oxygen. A compound (1) which is an atom and n is 2. (c) R ¹ and R ² are hydrogen atoms, R ³ is a halogen atom, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z , and A is oxygen. A compound (1) which is an atom and n is 2. (d) R ¹ and R ² are halogen atoms, R ³ is a hydrogen atom, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z , and A is oxygen. A compound (1) which is an atom and n is 2.

(E) R ¹ and R ³ are halogen atoms,
R ² is a hydrogen atom, and OC _x H _y F _z Cl _m is 3-O.
A compound (1) which is C _x F _z or 4-OC _x F _z , A is an oxygen atom, and n is 2. (f) R ^{1 to} R ³ are halogen atoms, and OC _x H _y F _z
Cl _m is 3-OC _x F _z or 4-OC _x F _z , A
Is an oxygen atom, and n is 2 (1). (g) R ¹ is an alkyl group having 1 to 4 carbon atoms, R ²
And R ³ is a hydrogen atom, and OC _x H _y F _z Cl _m is 3
A compound (1) which is —OC _x F _z or 4-OC _x F _z , A is an oxygen atom, and n is 2. (h) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ^1
2 and R ³ are hydrogen atoms, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z , A is an oxygen atom, and n is 2 (1 ).

(I) R ¹ is a haloalkyl group having 1 to 4 carbon atoms, R ² and R ³ are hydrogen atoms, and OC _x H
_y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z, A is an oxygen atom, and n is 2 (1). (j) R ¹ and R ² are halogen atoms, R ³ is a hydrogen atom, and OC _x H _y F _z Cl _m is 4-OC _{x Hy} F _z.
Wherein A is an oxygen atom and n is 2. (k) R ¹ and R ² are halogen atoms, R ³ is a hydrogen atom, and OC _x H _y F _z Cl _m is 4-OC _{x Hy} F _z.
A compound (1) which is Cl _m , A is an oxygen atom, and n is 2. (l) R ¹ and R ² are halogen atoms, R ³ is a hydrogen atom, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z , and A is sulfur. A compound (1) which is an atom and n is 2.

(M) R ¹ is a haloalkoxy group having 1 to 4 carbon atoms, R ² and R ³ are hydrogen atoms, and OC _x
H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F _z, A is an oxygen atom, and n is 2 (1). (n) R ¹ is a nitro group, R ² and R ³ are hydrogen atoms, and OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-.
A compound (1) which is OC _x F _z , A is an oxygen atom, and n is 2. (o) R ¹ and R ² are alkyl groups having 1 to 4 carbon atoms, R ³ is a hydrogen atom, and OC _{x Hy} F _z Cl _m is 3
A compound (1) which is —OC _x F _z or 4-OC _x F _z , A is an oxygen atom, and n is 2. (p) R ¹ and R ² are alkoxy groups having 1 to 4 carbon atoms, R ³ is a hydrogen atom, OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-OC _x F A compound (1) which is _z , A is an oxygen atom, and n is 2. (q) R ¹ is a hydroxyl group, R ² and R ³ are hydrogen atoms, and OC _x H _y F _z Cl _m is 3-OC _x F _z or 4-O.
A compound (1) which is C _x F _z , A is an oxygen atom, and n is 2.

(R) R ¹ is a hydroxyl group, R ² is a hydrogen atom, R ³ is a halogen atom, and OC _x H _y F _z C
The compound (1), wherein 1 _m is 3-OC _x F _z or 4-OC _x F _z , A is an oxygen atom, and n is 2. (s) R ¹ and R ³ are halogen atoms, R ² is a hydrogen atom, and OC _x H _y F _z Cl _m is 3-OC _{x Hy} F _z.
A compound (1) which is Cl _m or 4-OC _x F _z , A is an oxygen atom, and n is 3. As the compound (1) represented by these (a) to (s), the preferred ones shown in the explanation of R ^{1 to} R ³ , A, x, y, z, m, and n are more preferable. The thing can be illustrated. Specific examples of these compounds (1) include compounds {(1-1) to (1-
4), (1-8), (1-10), (1-13) ~ (1-17), (1-19), (1-30),
(1-35), (1-38), (1-40), (1-43), (1-46), (1-52), (1-5
3), (1-55), (1-56)} and the like.

As a preferred embodiment for producing the N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound represented by the above formula (1), in addition to the synthetic method 1 described as the second invention, the following two kinds The production method (Synthesis methods 2 and 3) can be mentioned. (Synthesis Method 2) The following formula (5):

[0051]

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(Wherein R ^{1 to} R ³ and n have the same meanings as described above) and the following formula (6):

[0053]

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(In the formula, L ³ represents a halogen atom, a methanesulfonyloxy group and a toluenesulfonyloxy group. X, y and z have the same meanings as described above.) N-represented by the above formula (1) characterized by reacting in the presence of
Process for producing [(fluoroalkoxy) phenoxyalkyl] benzamide compound. (Synthesis Method 3) The following formula (1a):

[0055]

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(Wherein R ^{1 to} R ³ , x, y, z, m and n have the same meanings as defined above) (1a)
Is reacted in the presence of a sulfiding agent and is referred to as an N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound [compound (1b) in which A is a sulfur atom in the above formula (1). ] Manufacturing method. The synthetic methods 1 to 3 of the compound (1) of the present invention will be described in more detail. [Synthesis Method 1] In Synthesis Method 1, as shown below, compound (2) and compound (3) are reacted in a solvent or without solvent in the presence of a base or a condensing agent to give compound (1a) [Compound (1) wherein A is an oxygen atom]

[0057]

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(Wherein R ^{1 to} R ³ , x, y, z, m, n
And L ¹ are as defined above. ) (1) When L ¹ is a halogen atom The above production method can be carried out by reacting the compound (2) with the compound (3) in a solvent or in the absence of a solvent in the presence of a base. The type of solvent is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroine, hexane, chlorobenzene, dichlorobenzene, methylene chloride, chloroform. Chlorinated or unchlorinated aromatic, aliphatic, cycloaliphatic hydrocarbons such as dichloroethane, trichloroethylene, cyclohexane; ethers such as diethyl ether, tetrahydrofuran, dioxane; acetone, methyl ethyl ketone, etc. Such ketones; nitriles such as acetonitrile, propionitrile, etc .; organic bases such as triethylamine, pyridine, N, N-dimethylaniline, etc .; N, N-dimethylformamide,
Examples thereof include polar solvents such as N, N-dimethylacetamide, dimethylsulfoxide, and dimethylimidazolinone; water; mixtures of the above solvents. Among these solvents, hydrocarbons and ethers are preferable.

The solvent is used in an amount of 5 to 80 for the compound (2).
Weight percent can be used; however, 10
~ 70% by weight is preferred. Although the molar ratio of the raw materials can be arbitrarily set, the ratio of the compound (3) is usually 0.5 to 2 mol per 1 mol of the compound (2). The type of base is not particularly limited, and examples thereof include organic bases such as triethylamine, pyridine, N, N-dimethylaniline, and 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); hydrogenation Inorganic bases such as sodium, sodium amide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate and potassium carbonate can be mentioned.

The amount of the base used is 1 with respect to the compound (2).
It is 10 to 10 times mol; but 1 to 5 times mol is preferable. The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent to be used; preferably 0 to 30.
° C. The reaction time varies depending on the above-mentioned concentration and temperature; it is usually 0.1 to 2 hours. Raw material compound (2)
Can be obtained by reacting compound (4) with potassium phthalimide in a solvent (first step) and then reacting with hydrazine (second step), as shown below.

[0061]

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(Where L ² , n, x, y, z and m are
It is the same as the above. ) First step The type of solvent used in the first step is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include
The hydrocarbons described in (1), ethers, ketones, nitriles, polar solvents, mixtures of the above solvents and the like can be mentioned. The amount of potassium phthalimide used is 1 to 10 times by mole with respect to compound (4); preferably 1
~ 5 times the molar amount. The reaction temperature is not particularly limited,
It is in the temperature range from the ice-cooling temperature to the boiling point of the solvent used or less; preferably 40 to 120 ° C. The reaction time varies depending on the above concentration and temperature; usually 0.5 to 10
Time.

Second Step The reaction with hydrazine can be carried out with or without isolation of the phthalimide compound obtained in the above first step. The type of solvent used in the second step is not particularly limited as long as it does not directly participate in this reaction, and examples thereof include the hydrocarbons, ethers, polar solvents, methanol, ethanol, and the like described in (1) above. Examples thereof include alcohols such as propanol and butanol, water, and a mixture of the above solvents. The amount of hydrazine used is 1 to 10 times mol, preferably 1 to 5 times mol, of the compound (4). The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent used or less; preferably 40 to 120 ° C. The reaction time varies depending on the concentration and temperature described above; it is usually 0.5 to 10 hours.

Compound (2) produced as described above
After completion of the reaction, can be subjected to ordinary post-treatments such as extraction, concentration, and filtration, and can be appropriately purified by a known means such as recrystallization or various types of chromatography, if necessary. The compound (4) can be obtained by the following method.

[0065]

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(Where n, x, y, z, m and L ² are
It is the same as the above. ) Further, the compound (4) can also be obtained by the following method.

[0067]

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(Where n, x, y, z, m and L ² are
It is the same as the above. ) As the compound (3), a commercially available product can be used. (2) When L ¹ is a hydroxyl group The above production method can be carried out by reacting the compound (2) with the compound (3) in a solvent or in the absence of a solvent in the presence of a condensing agent. The type of solvent is not particularly limited as long as it does not directly participate in the reaction, for example,
The same hydrocarbons, ethers, ketones, nitriles, polar solvents, and mixtures thereof as described in (1) above can be used. The amount of the solvent used may be 5 to 80% by weight of the compound (2); preferably 10 to 70% by weight.

The molar ratio of the raw materials can be set arbitrarily, but usually 0.5 mol of the compound (3) to 1 mol of the compound (2).
~ 2 moles. The type of dehydration condensing agent is not particularly limited, and examples thereof include dicyclohexylcarbodiimide (DC
C), diethyl azodicarboxylate, diisopropyl azodicarboxylate, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (WS
C), 1,1'-carbonyldiimidazole, sulfuric acid, 5
Examples thereof include phosphorus chloride. The amount of the dehydration condensing agent used is 1 to 10 times mol of the compound (2);
It is preferably 1 to 5 times mol. The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent used or less; preferably 0 to 50 ° C. The reaction time varies depending on the above-mentioned concentration and temperature;
5 to 8 hours.

Compound (1a) produced as described above
After completion of the reaction, can be subjected to ordinary post-treatments such as extraction, concentration, and filtration, and can be appropriately purified by a known means such as recrystallization or various types of chromatography, if necessary. [Synthesis Method 2] In Synthesis Method 2, as shown below, compound (5) and compound (6) are reacted in the presence of a base in a solvent to give compound (1a) [where A in compound (1) is A compound represented by an oxygen atom] is obtained.

[0071]

Embedded image

(Wherein R ^{1 to} R ³ , n, x, y, z, m
And L ³ are as defined above. ) The type of solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include hydrocarbons, ethers, polar solvents, water and mixtures thereof described in Synthesis Method 1. .

The amount of the solvent used is 5 to 80 for the compound (5).
Weight percent can be used; however, 10
~ 70% by weight is preferred. The type of base is not particularly limited, and examples thereof include the organic bases and inorganic bases described in (1) above; sodium hydroxide and potassium hydroxide are preferable. The amount of the base used is 1 to 10 times mol, but preferably 2 to 5 times mol, of the compound (5). The reaction temperature is not particularly limited, but is within a temperature range from the ice cooling temperature to the boiling point of the solvent used or less; preferably 0 to 100 ° C. The reaction time varies depending on the above concentration and temperature; it is usually 0.5 to 3 hours.

When the reaction is carried out in a two-layer system of an organic solvent and water, a phase transfer catalyst can be used to accelerate the reaction. The phase transfer catalyst is not particularly limited,
For example, tetrabutylammonium bromide, benzyltriethylammonium chloride, tricaprylylmethylammonium chloride, etc. can be mentioned. The amount of the phase transfer catalyst used is 0.01 to 5 times mol, preferably 0.05 to 0.5 times mol, of the compound (5). After completion of the reaction, the compound (1a) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration, and optionally purified by a known means such as recrystallization and various chromatography. can do. The compound (5) can be obtained by the following method.

[0075]

Embedded image

(In the formula, R ^{1 to} R ³ and n have the same meanings as described above.) As the compound (6), a commercially available product can be used, but it can also be obtained by the following procedure. You can

[0077]

Embedded image

(In the formula, x, y, z, m and L ³ have the same meanings as described above.) [Synthesis Method 3] The synthesis method 3 is as follows.
a) is reacted in the presence of a sulfiding agent in a solvent to give compound (1b)
This is a method for obtaining [a compound in which A in compound (1) is a sulfur atom].

[0079]

Embedded image

(In the formula, R ^{1 to} R ³ , n, x, y, z and m have the same meanings as described above.) The kind of the solvent is not particularly limited as long as it does not directly participate in the reaction. Instead, for example, the hydrocarbons, ethers, and mixtures thereof described in Synthesis Method 1 can be mentioned. The amount of the solvent used is 5 to 80% by weight of the compound (1a).
Can be used as follows: 10-70
% By weight is preferred. The type of the sulfiding agent is not particularly limited, and examples thereof include phosphorus pentasulfide, 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4-diphosphetan-2,4-disulfide (Lawson's reagent ), Hydrogen sulfide and the like. The amount of the sulfiding agent used is 1 to 10 times mols of the compound (1a); preferably 1
~ 5 times the molar amount.

The reaction temperature is not particularly limited, but is within the temperature range from the ice cooling temperature to the boiling point of the solvent used or less; preferably 40 to 120 ° C. The reaction time varies depending on the concentration and temperature described above; it is usually 0.5 to 10 hours. After completion of the reaction, the compound (1b) produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration, and optionally purified by a known means such as recrystallization and various chromatography. can do.

Examples of pests in agricultural and horticultural fields where the compound (1) of the present invention has a controlling effect include agricultural and horticultural pests [eg, Hemiptera (planthoppers, leafhoppers, aphids,
Whiteflies, etc.), lepidoptera (armyworms, moths,
Coleoptera, Pests, Pests, and White butterfly, Coleoptera (Tenebrionidae, Weevils,
Chrysomelidae, chafers, etc.), mites (such as citrus mites of the mite family, spider mites, etc.), hygienic pests (eg, flies, mosquitoes, cockroaches), storage pests (Euphorbiaceae, weevil) Etc.), nematodes (root-knot nematodes, cyst nematodes, nebulae nematodes, singale nematodes, pine wood nematodes, etc.), ticks, and the like, and agricultural and horticultural pathogens (eg, wheat red rust, barley powdery mildew, Cucumber downy mildew, rice blast, tomato epidemic, etc.) can be mentioned.

The pesticide for agricultural and horticultural use of the present invention has a particularly remarkable nematicidal, acaricidal and bactericidal effect and contains one or more compounds (1) as active ingredients. The compound (1) can be used alone,
Usually, a carrier, a surfactant, a dispersant, an auxiliary agent, etc. are prepared by a conventional method (eg, a powder, emulsion, fine granule, granule, wettable powder, oily suspension, aerosol, etc.) It is preferable to use.

As the carrier, for example, talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, urea and the like solid carriers; hydrocarbons (kerosene, mineral oil, etc.), aromatic carbonization Hydrogen (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.), esters (ethyl acetate, ethylene) Liquid carriers such as glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethylsulfoxide, etc.), water; air, nitrogen, carbon dioxide, freon, etc. Body carrier (in this case, can be mixed injection), and the like.

Examples of surfactants and dispersants which can be used to improve the performance of the present agent such as adhesion to animals and plants, absorption improvement, drug dispersion, emulsification, spreading and the like include, for example, alcohol sulfates and alkyls. Examples thereof include sulfonate, lignin sulfonate, polyoxyethylene glycol ether and the like. In order to improve the properties of the preparation, for example, carboxymethylcellulose, polyethylene glycol, gum arabic and the like can be used as an auxiliary agent.

In the production of the present agent, the above-mentioned carrier, surfactant, dispersant and auxiliary agent can be used alone or in suitable combination according to the purpose.
When the compound (1) of the present invention is formulated, the concentration of the active ingredient is usually from 1 to 50% by weight in an emulsion, and usually 0.3% in a powder.
25 to 25% by weight, usually 1 to 90% by weight for wettable powders, usually 0.5 to 5% by weight for granules, 0.5 to 5% by weight for oils and 0.1 to 5% by weight for aerosols. is there. These preparations can be diluted to an appropriate concentration and applied to various uses by spraying them on plant foliage, soil, or the water surface of paddy fields, or directly applying them, depending on the purpose.

[0087]

The present invention will be specifically described below with reference to examples. Note that these examples do not limit the scope of the present invention. Example 1 [Synthesis of Compound (2)] (1) Synthesis of 2- (4-trifluoromethoxyphenoxy) ethylamine [Compound (2-2)] Methanesulfonic acid 2- (4-trifluoromethoxyphenoxy) ethyl ester (3.00 g) was dissolved in N, N-dimethylformamide (20 ml), potassium phthalimide (2.04 g) was added, and the mixture was stirred at 100 ° C for 3 hr. After the reaction was completed, water (100 ml) was added and stirred,
The precipitate formed was filtered off. The obtained precipitate was added to ethanol (30 ml) and dissolved by heating, hydrazine hydrate (0.55 g) was added, and the mixture was heated under reflux for 3 hours. After completion of the reaction, ethanol was distilled off under reduced pressure, 5N aqueous sodium hydroxide solution (50 ml) was subsequently added to dissolve the precipitate, and the target compound was extracted with ethyl acetate. Then, the organic layer is washed with saturated brine, dried over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by silica gel chromatography (Wakogel C-200, elution with ethyl acetate followed by elution with ethanol). As a result, 1.54 g of the objective compound which was a pale yellow oily substance was obtained.

¹ H-NMR (CDCl ₃ , δppm) 2.18 to 2.47 (2H, br), 3.11 (2H,
t, J = 5.1 Hz), 3.91 to 4.09 (2H,
m), 6.88 to 7.25 (4H, m)

(2) 2- [4- (2,2,2-trifluoroethoxy) phenoxy] ethylamine [Compound (2-3)
2- [4- (2,2,2-trifluoroethoxy) phenoxy] ethyl bromide (4.50 g) was dissolved in N, N-dimethylformamide (30 ml), and potassium phthalimide (3.05 g) was added. In addition, it stirred at 100 degreeC for 3 hours. After the reaction was completed, water (120 ml) was added and stirred,
The precipitate formed was filtered off. The obtained precipitate was added to ethanol (50 ml) and dissolved by heating, hydrazine hydrate (0.55 g) was added, and the mixture was heated under reflux for 3 hours. After completion of the reaction, 5N hydrochloric acid (50 ml) was added and the mixture was stirred and filtered while hot. The obtained filtrate was washed with toluene,
Subsequently, the aqueous layer was made basic with a 5N sodium hydroxide aqueous solution, and the target compound was extracted with ethyl acetate. Next, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.57 g of the target compound as a pale yellow oily substance.

¹ H-NMR (CDCl ₃ , δppm) 1.39 to 1.54 (2H, br), 2.95 to 3.1
3 (2H, m), 3.87 to 4.37 (4H, m),
6.74-6.97 (4H, m)

(3) 2- [4- (1,1,2,2-tetrafluoroethoxy) phenoxy] ethylamine [compound
(2-5)] Methanesulfonic acid 2- [4- (1,1,2,2-tetrafluoroethoxy) phenoxy] ethyl ester (1.
61 g) with N, N-dimethylformamide (10 ml)
, Potassium phthalimide (1.02 g) was added, and the mixture was stirred at 100 ° C. for 3 hours. After the reaction, water (50
(ml) was added and the precipitated crystals were collected by filtration, pulverized and washed with water. Next, this was dissolved by heating with ethanol (20 ml), hydrazine hydrate (0.28 g) was added, and the mixture was stirred for 3 hours. After the reaction was completed, ethanol was distilled off under reduced pressure,
Next, 5N sodium hydroxide (30 ml) was added to dissolve the precipitate, and the target compound was extracted with ethyl acetate. Next, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and ethyl acetate was distilled off under reduced pressure. By purifying the obtained oily substance by silica gel chromatography (Wakogel C-200, eluting with ethyl acetate to ethanol),
0.89 g of the target compound which was a pale yellow oily liquid crystal was obtained.

¹ H-NMR (CDCl ₃ , δppm) 1.82 to 2.19 (2H, br), 3.01 to 3.2
0 (2H, br), 3.98 (2H, t), 5.89
(1H, m), 6.86 to 7.18 (4H, m)

(4) 2- [4- (2-chloro-1,1,2)
Synthesis of -trifluoroethoxy) phenoxy] ethylamine [Compound (2-6)] 2- [4- (2-chloro-1,1,2-trifluoroethoxy) phenoxy] ethyl bromide (5.00 g) was added to N, Dissolve in N-dimethylformamide (30 ml),
Add potassium phthalimide (3.05g), 100 ℃
For 3 hours. After completion of the reaction, water (120 ml) was added and stirred, and the generated precipitate was taken out by filtration. The obtained precipitate was added to ethanol (50 ml) and dissolved by heating, hydrazine hydrate (0.83 g) was added, and the mixture was heated under reflux for 3 hours. After the reaction was completed, 5N hydrochloric acid (70 ml) was added and the mixture was stirred and filtered while hot. The obtained filtrate was washed with toluene, then the aqueous layer was made basic with 5N aqueous sodium hydroxide solution, and the target compound was extracted with ethyl acetate. Next, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 2.73 g of the target compound as a pale yellow oily substance.

¹ H-NMR (CDCl ₃ , δppm) 1.18 to 1.75 (2H, br), 2.95 to 3.1
4 (2H, m), 3.49 (2H, t, J = 4.9H)
z), 6.14 to 6.35 (1H, m), 6.74 to
7.26 (4H, m)

(5) Synthesis of 2- (3-trifluoromethoxyphenoxy) ethylamine [Compound (2-9)] Methanesulfonic acid 2- (3-trifluoromethoxyphenoxy) ethyl ester (3.00 g) was added to N, It was dissolved in N-dimethylformamide (20 ml), potassium phthalimide (2.04 g) was added, and the mixture was stirred at 100 ° C. for 3 hr. After the reaction was completed, water (100 ml) was added and stirred,
The precipitate formed was filtered off. The obtained precipitate was added to ethanol (30 ml) and dissolved by heating, hydrazine hydrate (0.55 g) was added, and the mixture was heated under reflux for 3 hours. After completion of the reaction, 5N hydrochloric acid (50 ml) was added and the mixture was stirred and filtered while hot. The obtained filtrate was washed with toluene,
Subsequently, the aqueous layer was made basic with a 5N sodium hydroxide aqueous solution, and the target compound was extracted with ethyl acetate. Then, the organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.76 g of a target compound as a pale yellow oily substance.

¹ H-NMR (CDCl ₃ , δppm) 1.61 to 1.92 (2H, br), 3.09 (2H,
t, J = 5.1 Hz), 3.99 (2H, t, J = 5.
1 Hz), 6.67 to 7.35 (4H, m)

(6) Synthesis of 3- (4-trifluoromethoxyphenoxy) propylamine [Compound (2-10)] Methanesulfonic acid 3- (4-trifluoromethoxyphenoxy) propyl ester (3.14 g) was added to N , N-dimethylformamide (20 ml), potassium phthalimide (2.04 g) was added, and the mixture was stirred at 100 ° C. for 3 hr. After the reaction was completed, water (100 ml) was added and the mixture was stirred, and the generated precipitate was taken out by filtration. The obtained precipitate was added to ethanol (30 ml) and dissolved by heating, hydrazine hydrate (0.55 g) was added, and the mixture was heated under reflux for 2 hours. After completion of the reaction, 5N hydrochloric acid (50 ml) was added and the mixture was stirred and filtered while hot. The obtained filtrate was washed with toluene, then the aqueous layer was made basic with 5N aqueous sodium hydroxide solution, and the target compound was extracted with ethyl acetate. Next, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.68 g of the target compound as a pale yellow oily substance.

¹ H-NMR (CDCl ₃ , δppm) 1.81 to 2.06 (2H, m), 2.22 to 2.51
(2H, br), 2.93 (2H, t, J = 6.6H
z), 4.04 (2H, t, J = 5.9Hz), 6.7.
7 to 7.24 (4H, m)

(7) Synthesis of other compounds (2) in Table 2 Other compounds (2) in Table 2 were synthesized according to any one of the methods (1) to (6). Table 2 shows the compounds synthesized as described above and their physical properties.

[0100]

[Table 2]

Example 2 [Synthesis of Compound (1)] The target compound (1) was synthesized using the compound (2) obtained in Example 1. (1) N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2-fluorobenzamide [Compound (1-
2)] Synthesis of 2- (4-trifluoromethoxyphenoxy) ethylamine (1.10 g) and 2-fluorobenzoic acid (0.70
g) in a solution of dichloromethane (20 ml) with WSC
[1-Ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride] (1.10 g) was added, and the mixture was stirred at room temperature for 3 times.
Stirred for hours. After the reaction was completed, water (10 m) was added to the reaction mixture.
l) was added for extraction, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel chromatography (Wako Gel C
-200, toluene: ethyl acetate = 9: 1 elution) to give 1.21 g of the target compound as colorless crystals.
Obtained.

¹ H-NMR (CDCl ₃ , δppm) 3.87 to 4.22 (4H, m), 6.85 to 7.52
(8H, m), 8.06 to 8.14 (1H, m)

(2) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2-chlorobenzamide [Compound (1-3)] 2- (4-trifluoromethoxyphenoxy) ethylamine (1. 10 g) and triethylamine (0.51 g)
A solution of 2-chlorobenzoyl chloride (0.88 g) in tetrahydrofuran (5 ml) was added dropwise to a tetrahydrofuran solution (20 ml) with and under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure.
The obtained residue is subjected to silica gel chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 9: 1 elution) to obtain 1.53 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.78 to 4.22 (4H, m), 6.52 to 6.80
(1H, br), 6.80 to 7.87 (8H, m)

(3) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2,6-difluorobenzamide [Compound (1-10)] 2- (4-trifluoromethoxyphenoxy) ethylamine ( 1.10 g) and triethylamine (0.51 g)
In a solution of tetrahydrofuran (20 ml) with
A solution of difluorobenzoyl chloride (0.88 g) in tetrahydrofuran (5 ml) was added dropwise under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was chromatographed on silica gel (Wakogel C-200, toluene: ethyl acetate = 9: 1 elution).
The desired compound in the form of colorless crystals was purified by 1.
Obtained 48 g.

¹ H-NMR (CDCl ₃ , δppm) 3.78 to 4.22 (4H, m), 6.28 to 6.53
(1H, br), 6.78 to 7.47 (7H, m)

(4) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2,4,6-trifluorobenzamide [Compound (1-14)] 2- (4-trifluoromethoxyphenoxy) ) WSC (1.15 g) was added to a solution of ethylamine (1.10 g) and 2,4,6-trifluorobenzoic acid (0.87 g) in dichloromethane (20 ml), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water (10 ml) was added to the reaction mixture for extraction, the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (Wako Gel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 1.27 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.77 to 4.23 (4H, m), 6.26 to 6.48
(1H, br), 6.61 to 7.26 (6H, m)

(5) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2-methylbenzamide [Compound (1-15)] 2- (4-trifluoromethoxyphenoxy) ethylamine (1. 10 g) and triethylamine (0.51 g)
A solution of 2-methylbenzoyl chloride (0.77 g) in tetrahydrofuran (5 ml) was added dropwise to a tetrahydrofuran solution (20 ml) with and under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure.
The obtained residue is subjected to silica gel chromatography (Wako Gel C-2
00, toluene: ethyl acetate = 9: 1 elution) to obtain 1.31 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 2.44 (3H, s), 3.75 to 4.20 (4H,
m), 6.14 to 6.32 (1H, br), 6.80 to
7.41 (8H, m)

(6) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2-trifluoromethylbenzamide [Compound (1-17)] 2- (4-trifluoromethoxyphenoxy) ethylamine ( 1.10 g) and triethylamine (0.51 g)
A solution of 2-trifluoromethylbenzoyl chloride (1.04 g) in tetrahydrofuran (5 ml) was added dropwise to a tetrahydrofuran (20 ml) solution of and under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wako Gel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 1.67 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.79 to 4.18 (4H, m), 6.15 to 6.31
(1H, br), 6.80 to 7.76 (8H, m)

(7) Synthesis of N- [2- (4-difluoromethoxyphenoxy) ethyl] -2,6-difluorobenzamide [compound (1-35)] N- [2- (4-hydroxyphenoxy) ethyl] −
2,6-Difluorobenzamide (1.16 g), potassium hydroxide (1.10 g) and tetrabutylammonium bromide (0.10 g) were added to dichloromethane (30 m).
1) and water (10 ml) were added to the mixture, and chlorodifluoromethane (3.50 g) was slowly blown in at room temperature with stirring, and the mixture was further stirred at room temperature for 1 hour. After completion of the reaction, dichloromethane was added to the reaction mixture for extraction, the organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 0.87 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.78 to 4.20 (4H, m), 6.42 (1H,
t, J = 74.2), 6.28 to 6.51 (1H, b
r), 6.71 to 7.44 (7H, m)

(8) N- {2- [4- (2-chloro-1,
1,2-trifluoroethoxy) phenoxy] ethyl}
Synthesis of 2,6-difluorobenzamide [Compound (1-38)] 2- [4- (2-chloro-1,1,2-trifluoroethoxy) phenoxy] ethylamine (1.08 g) and triethylamine (0. 40 g) in a solution of tetrahydrofuran (20 ml) and 2,6-difluorobenzoyl chloride (0.71 g) in tetrahydrofuran (5 m
The solution of l) was added dropwise under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 1.76 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.77 to 4.21 (4H, m), 6.14 to 6.35
(1H, m), 6.53 to 6.73 (1H, br),
6.73-7.44 (7H, m)

(9) Synthesis of N- {2- [4- (2,2,2-trifluoroethoxy) phenoxy] ethyl} -2,6-difluorobenzamide [compound (1-40)] 2- [4 Tetrahydrofuran (20 ml) of-(2,2,2-trifluoroethoxy) phenoxy] ethylamine (0.94 g) and triethylamine (0.40 g)
A solution of 2,6-difluorobenzoyl chloride (0.70 g) in tetrahydrofuran (5 ml) was added dropwise to the above solution under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour.
After completion of the reaction, the generated triethylamine hydrochloride was filtered off,
The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wako Gel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 1.18 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 3.80-4.40 (6H, m) 6.28-6.53
(1H, br), 6.72 to 7.44 (7H, m)

(10) Synthesis of N- [3- (4-trifluoromethoxyphenoxy) propyl] -2,6-difluorobenzamide [Compound (1-43)] 3- (4-trifluoromethoxyphenoxy) propylamine (1.18 g) and triethylamine (0.50
g) in a solution of tetrahydrofuran (20 ml) with
2,6-difluorobenzoyl chloride (0.88 g)
A tetrahydrofuran (5 ml) solution of was added dropwise under ice-cooling stirring, and the mixture was further stirred at room temperature for 1 hour. After the reaction was completed, the generated triethylamine hydrochloride was filtered off, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wakogel C-200, eluted with toluene: ethyl acetate = 9: 1) to obtain 1.38 g of the target compound as colorless crystals.

¹ H-NMR (CDCl ₃ , δppm) 2.03 to 2.21 (2H, m), 3.57 to 4.17
(4H, m), 6.19 to 6.38 (1H, br),
6.74 to 7.43 (7H, m)

(11) Synthesis of N- [2- (4-trifluoromethoxyphenoxy) ethyl] -2,6-difluorobenzthioamide [Compound (1-46)] N- [2- (4-trifluoromethoxy) Phenoxy) ethyl] -2,6-difluorobenzamide (1.44
Lawson's reagent (1.94 g) was added to a solution of g) in toluene (20 ml), and the mixture was heated under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Wako Gel C-200, eluted with toluene: ethyl acetate = 20: 1) to obtain 1.56 g of the target compound as pale yellow crystals.

¹ H-NMR (CDCl ₃ , δppm) 4.20 to 4.37 (4H, m), 6.79 to 7.38
(7H, m), 7.71 to 7.89 (1H, br)

(12) Synthesis of other compounds (1) in Tables 3 to 6 Other compounds (1) in Tables 3 to 6 were synthesized according to the methods described in (1) to (11) above. did. The compounds synthesized as above and their physical properties are shown in Table 3 to
6 is shown.

[0124]

[Table 3]

[0125]

[Table 4]

[0126]

[Table 5]

[0127]

[Table 6]

Example 3 [Preparation of preparation] (1) Preparation of granules 5 parts by weight of compound (1-1), 35 parts by weight of bentonite, 57 parts by weight of talc, neoperex powder (trade name; manufactured by Kao Corporation) ) 1 part by weight and 2 parts by weight of sodium lignin sulfonate were uniformly mixed, then a small amount of water was added and kneaded, and then granulated and dried to obtain a granule.

(2) Preparation of Wettable Powder 10 parts by weight of compound (1-1), 70 parts by weight of kaolin, 18 parts by weight of white carbon, 1.5 parts by weight of neoperex powder (trade name; manufactured by Kao Corporation) And 0.5 part by weight of DEMOL (trade name; manufactured by Kao Corporation) were uniformly mixed and then pulverized to obtain a wettable powder.

(3) Preparation of emulsion 20 parts by weight of compound (1-1) and 70 parts by weight of xylene were added,
Toxanone (trade name; manufactured by Sanyo Chemical Industry Co., Ltd.) (10 parts by weight) was added, mixed uniformly, and dissolved to obtain an emulsion.

(4) Preparation of Dust Preparation A powder preparation was obtained by uniformly mixing 5 parts by weight of compound (1-1), 50 parts by weight of talc and 45 parts by weight of kaolin.

Example 4 [Efficacy test] (1) Efficacy test against sweet potato nematode Compound (1) shown in Tables 3 to 6 prepared according to Example 3
Each water dispersible powder was diluted to 300 ppm with water.
1 ml was taken in a test tube, and 0.9 ml of an aqueous solution containing about 500 sweet potato nematodes was added (final concentration 30
ppm). Next, these test tubes were left in a constant temperature room at 25 ° C., and after 2 days, they were observed under a microscope to determine the nematicidal rate.
Evaluation of nematicidal effect depends on the range of nematicidal rate.
4 stages (A: 100%, B: less than 100 to 80%,
C: less than 80 to 60%, D: less than 60%). Table 7 shows the results.

[0133]

[Table 7]

(2) Efficacy test against Nicaria spp. Eggs Compounds (1) shown in Tables 3 to 6 prepared according to Example 3
Each hydration agent in water containing a surfactant (0.01%).
Each bean leaf piece (20 mm in diameter) was diluted to 0 ppm, and 15 adult female adult mites were allowed to produce eggs in each of these drug solutions for 24 hours, and then the adult was removed, and each leaf piece (diameter 20 mm) was immersed for 10 seconds. Next, the test tube containing each of these leaf pieces was left in a constant temperature room at 25 ° C., and after 6 days, the number of unembedded eggs in each leaf piece was counted to determine the ovicidal rate.

The evaluation of the ovicidal effect is carried out according to the range of the ovicidal rate in four stages from A to D (A: 100%, B: less than 100)
80%, C: less than 80 to 60%, D: less than 60%). Table 8 shows the results of evaluation of these ovicidal effects.

[0136]

[Table 8]

(3) Control efficacy test against rice blast (preventive effect) Ten rice (cultivar; Nihonbare) was grown in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage Each wettable powder of the compound (1) shown in Tables 3 to 6 prepared according to Example 3 was diluted to 500 ppm with water containing a surfactant (0.05%), and 20 ml per pot was prepared. Sprayed. After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then the leaves of the conidia of rice blast prepared from the diseased leaves were uniformly spray-inoculated onto the plant leaves. 28 days after inoculation for 5 days
The plants were grown in a humidity chamber at ℃ and the degree of rice blast lesions on the leaves was investigated.

The evaluation of the bactericidal effect is carried out in 6 stages from 0 to 5 (0: whole diseased, 1: lesion area is about 60%, 2: lesion area is compared with the degree of lesion in the untreated section. Is about 40% 3:
Lesion area is about 20%, 4: Lesion area is 10% or less,
5: no lesion). Table 9 shows the results.

[0139]

[Table 9]

(4) Control Efficacy Test for Wheat Leaf Rust (Preventive Effect) 10 wheats (cultivar: Kobushi-komugi) were cultivated in a plastic flower pot with a diameter of 6 cm, and seedlings of 1.5 leaf stage were cultivated. A wettable powder of the compound (1) shown in Tables 3 to 6 prepared according to Example 3 was mixed with a surfactant (0.05
%) To 500 ppm with water containing
Sprayed at 0 ml. After spraying, cultivate in a glass greenhouse for 2 days, and then spore suspension of wheat leaf rust (3 x 10
^The plants were uniformly spray-inoculated with ⁵ spores / ml). After inoculation, the plants were grown for one week in a glass greenhouse, and the degree of wheat leaf rust spots on the first leaves was examined. The result is
Table 6 shows the 6-step evaluation method described in (3).

[0141]

[Table 10]

[0142]

INDUSTRIAL APPLICABILITY The novel N-[(fluoroalkoxy) phenoxyalkyl] benzamide derivative of the present invention has excellent effects such as nematicide, acaricide and sterilization.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI Technical display location C07C 217/20 7457-4H C07C 217/20 231/02 231/02 235/48 9547-4H 235 / 48 235/60 9547-4H 235/60 253/30 8927-4H 253/30 255/57 8927-4H 255/57 327/48 7106-4H 327/48 (72) Inventor Tatsumi Tanaka Ube City, Yamaguchi Prefecture Ogushi At 1978, 5 Ube Kosan Co., Ltd. Ube Laboratory

Claims (5)

[Claims] 1. The following formula (1): An N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound represented by: In the formula, R ¹ ~
R ³ , A, n, x, y, z and m are as follows.
R ¹ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms. , Cyano group, nitro group, or hydroxyl group. R ² is a hydrogen atom, a halogen atom, or a carbon atom number 1 to
4 represents an alkyl group having 4 or an alkoxy group having 1 to 4 carbon atoms. R ³ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, or 1 carbon atom.
4 represents a haloalkoxy group, a cyano group, or a nitro group. A represents an oxygen atom or a sulfur atom. n is 1 to
Represents an integer of 6. x represents an integer of 1 to 4. y is 0
Represents an integer of from 6 to 6. z represents an integer of 2 to 9. m is
It represents an integer of 0 to 2. However, 2x + 1 = y + z + m. 2. The following formula (2): (In the formula, n, x, y, z and m have the same meanings as described in claim 1.) and a (fluoroalkoxy) phenoxyalkylamine compound represented by the following formula (3): (In the formula, R ^{1 to} R ³ and A have the same meanings as described in claim 1. L ¹ represents a halogen atom or a hydroxyl group.). The method for producing an N-[(fluoroalkoxy) phenoxyalkyl] benzamide compound represented by formula (1) according to claim 1, wherein A is an oxygen atom. 3. The following formula (2): (In the formula, n, x, y, z and m are as defined in claim 1.) A (fluoroalkoxy) phenoxyalkylamine compound represented by the formula (1). 4. The following formula (4): (In the formula, L ² represents a halogen atom, a methanesulfonyloxy group, or a toluenesulfonyloxy group. N,
x, y, z and m have the same meanings as described in claim 1. )
The method for producing a (fluoroalkoxy) phenoxyalkylamine compound represented by the formula (2) according to claim 3, wherein the (fluoroalkoxy) phenoxyalkyl compound represented by: is aminated. 5. N-represented by the formula (1) according to claim 1.
[(Fluoroalkoxy) phenoxyalkyl] benzamide compound is an active ingredient for agricultural and horticultural pest control agents.