JP2002205991A - 1,2,4-oxadiazol-5-(thi)one derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an insecticide having a new molecular structure and extremely high insecticidal activity against various harmful insect pests. SOLUTION: This insecticide comprises a compound of the formula (wherein, W is O or S), a salt or amide derivative thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazol-5 (4H) -one derivative, 3- (4-trifluoro) The present invention relates to a methyl-3-pyridyl) -1,2,4-oxadiazole-5 (4H) -thione derivative, a salt thereof, an amide derivative thereof, and an agricultural chemical containing the same as an active ingredient.

[0002]

2. Description of the Related Art Conventionally, 1,2,3 having a pyridyl group at the 3-position.
The 4-oxadiazole derivative is described, for example, in WO 9857969 and JP-A-2000-38385. However, 1,2,4-oxadiazole derivatives having a pyridyl group at the 3-position described in these publications have the general formula

[0003]

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As shown in the above formula, no hydrogen atom is bonded to the nitrogen atom at position 4 of the oxadiazole ring, the bond at positions 4 and 5 is a double bond, and an oxo group or thioxo Because they have no groups, their insecticidal activity is inadequate.

[0005] For example, chemical abstracts
Chem. Abstr., 62 , 5283 (1965)

[0006]

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1,2,4-oxadiazol-5 (4H) -one having an unsubstituted 3-pyridyl group at the 3-position represented by Phosphorus Sulfur and Silicon Phosphorus, Sulfur and Silicon, 1991, 6
2 , 47-51

[0008]

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A 1,2,4-oxadiazol-5 (4H) -one derivative having an unsubstituted 3-pyridyl group at the 3-position and a 1- and 2-unsubstituted 3-pyridyl group at the 3-position ,
The 2,4-oxadiazole-5 (4H) -thione derivatives are described as compounds (2e) and (3e), respectively. However, in these compounds, a benzene ring is covalently bonded to the nitrogen atom at the 4-position of the oxadiazole ring, a hydrogen atom cannot be bonded to the nitrogen atom, and the 4-position of the pyridyl group has no atom. Since it is a substitution and is not substituted by a trifluoromethyl group, it is known to have pharmacological activity, but it is not known to have insecticidal activity and is not suggested in the literature. .

[0010]

The inventors of the present invention have conducted intensive studies on 1,2,4-oxadiazole derivatives having a pyridyl group at the 3-position, and as a result, have found that 4
A compound in which a hydrogen atom is bonded to the nitrogen atom at position 1, a bond at positions 4 and 5 is a single bond, and a compound having an oxo group or a thioxo group at position 5 has extremely excellent insecticidal activity against various harmful insects. And completed the present invention. Further, an amide derivative in which the bond between the nitrogen atom at the 4-position of the oxadiazole ring and the acyl group is broken in the soil or the plant and converted into a compound in which a hydrogen atom is bonded to the nitrogen atom, The present inventors have found that they have the same insecticidal activity and completed the present invention.

[0011]

According to the present invention, there is provided a compound represented by the general formula:

[0012]

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[Wherein, W represents an oxygen atom or a sulfur atom. A salt or amide derivative thereof, and an agricultural chemical containing them as an active ingredient.

In the present invention, the “amide derivative” is
A compound in which an acyl group is bonded to the 1-position nitrogen atom of a 1,2,4-oxadiazole ring, for example, a C ₂ -C ₈ alkylcarbonyl group and a C ₂ -C ₈ alkoxycarbonyl group are bonded to a nitrogen atom Compound.

In the present invention, "C ₂ -C ₈ alkylcarbonyl group" includes, for example, acetyl, propionyl, propylcarbonyl, isopropylcarbonyl, cyclopropylcarbonyl, butylcarbonyl, sec-butylcarbonyl, isobutylcarbonyl, tert-butylcarbonyl A straight-chain having 2 to 8 carbon atoms, such as cyclobutylcarbonyl, pentylcarbonyl, pentyl-2-carbonyl, 2,2-dimethyl-1-propylcarbonyl, cyclopentylcarbonyl, hexylcarbonyl, heptylcarbonyl and octylcarbonyl. A straight-chain or branched-chain or cyclic alkylcarbonyl group, preferably a straight-chain or branched-chain or cyclic alkylcarbonyl having 2 to 6 carbon atoms, more preferably acetyl, propionyl or cyclopropyl. A ylcarbonyl group.

In the present invention, "C ₂ -C ₈ alkoxycarbonyl group" includes, for example, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, sec-butoxycarbonyl, isobutoxycarbonyl, cyclobutoxycarbonyl, tert-butoxycarbonyl Pentoxycarbonyl, pentyl-2-oxycarbonyl, 2,2-dimethylpentyl-1-oxycarbonyl, pentyl-3-oxycarbonyl, hexyloxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1,2,2-trimethyl A carbonyl group to which a linear or branched or cyclic alkoxy group having 1 to 7 carbon atoms such as propoxycarbonyl and 1-isopropyl-2-methylpropoxycarbonyl is bonded;
Preferably, it is a carbonyl group to which a straight-chain or branched-chain alkoxy group having 1 to 4 carbon atoms is bonded, and more preferably, a straight-chain or branched-chain alkoxy group having 1 to 3 carbon atoms is It is a bonded carbonyl group, still more preferably a carbonyl group to which an alkoxy group having 1 or 2 carbon atoms is bonded, and particularly preferably a methoxycarbonyl group.

In X of the present invention, the "leaving group" is not particularly limited as long as it is a substituent capable of leaving by a usual nucleophilic substitution reaction, and is preferably a halogen atom or a C ₁ -C ₆ alkoxy group. It is.

In the present invention, the "halogen atom" is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
Preferably, it is a chlorine atom or a bromine atom.

In the present invention, "C ₁ -C ₆ alkoxy group" includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy,
-Methylbutoxy, neopentoxy, 1-ethylpropoxy, hexyloxy, 1-methylpentoxy, 3,3
-Dimethylbutoxy, 1,1-dimethylbutoxy, 1,
It is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as 2-dimethylbutoxy and 2-ethylbutoxy, preferably a straight-chain or branched-chain alkoxy group having 1 to 4 carbon atoms. And more preferably a methoxy or ethoxy group.

The compound (I) of the present invention can be converted into a salt used for ordinary pesticides, for example, an alkali metal salt, an alkaline earth metal salt or an ammonium salt. If there is a basic moiety, it can be made into a salt such as, for example, sulfate, hydrochloride, nitrate or phosphate. These salts are included in the present invention as long as they can be used as agricultural and horticultural herbicides.

In the present invention, the “alkali metal salt” is
For example, it can be a sodium, potassium or lithium salt, preferably a sodium or potassium salt.

In the present invention, "alkaline earth metal salt"
Can be, for example, a calcium salt or a magnesium salt, preferably a calcium salt.

The solvates of the compound of the present invention are also included in the present invention.

The compounds of the present invention include compounds having an asymmetric carbon. In such a case, the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio. .

In the compound (I) of the present invention, W is preferably an oxygen atom.

The amide derivative of the present invention is preferably an amide derivative in which a C ₂ -C ₈ alkylcarboxylic group or a C ₂ -C ₈ alkoxycarbonyl group is bonded to a nitrogen atom, more preferably, acetyl, An amide derivative in which a propionyl, cyclopropylcarbonyl or methoxycarbonyl group is bonded to a nitrogen atom.

In the compound (I) of the present invention, a salt thereof or an amide derivative thereof, W is preferably an oxygen atom or a sulfur atom, and the amide derivative is preferably a C ₂ -C ₈ alkylcarboxylic group or a C ₂ -C ₄ Compound (I), which is an amide derivative having a C ₈ alkoxycarbonyl group bonded to a nitrogen atom, a salt thereof or an amide derivative thereof, more preferably W is an oxygen atom, and the amide derivative is acetyl, propionyl,
Compound (I), which is an amide derivative in which a cyclopropylcarbonyl or methoxycarbonyl group is bonded to a nitrogen atom,
A salt thereof or an amide derivative thereof.

Representative compounds of the present invention are shown in the following Tables 1 to 12, but the present invention is not limited to these compounds.

Hereinafter, "Me" is a methyl group, "Et" is an ethyl group, "Pr" is a propyl group, "iPr" is an isopropyl group, "cPr" is a cyclopropyl group, and "Bu" is a Butyl group, “iBu” is isobutyl group, “sBu” is sec-butyl group, “cBu” is cyclobutyl group, “tBu” is tert-
Butyl group, “Pent” is a pentyl group, “cPent” is a cyclopentyl group, “Hex” is a hexyl group, “cHex”
Represents a cyclohexyl group, respectively.

[0030]

[Table 1]

[0031]

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化合物 Compound number WR ──────────────── 1-1 OH 1-2 O COMe 1- 3 O COEt 1-4 O COPr 1-5 O COiPr 1-6 O COcPr 1-7 O COBu 1-8 O COiBu 1-9 O COsBu 1-10 O COcBu 1-11 O COtBu 1-12 O COPent 1- 13 O COcPent 1-14 O COHex 1-15 O COcHex 1-16 O CO ₂ Me 1-17 O CO ₂ Et 1-18 O CO ₂ Pr 1-19 O CO ₂ iPr 1-20 O CO ₂ Bu 1- 21 O CO ₂ iBu 1-22 O CO ₂ Pent 1-23 O CO ₂ Hex 1-24 SH 1-25 S COMe 1-26 S COEt 1-27 S COPr 1-28 S COiPr 1-29 S COcPr 1- 30 S COBu 1-31 S COiBu 1-32 S COsBu 1-33 S COcBu 1-34 S COtBu 1-35 S COPent 1-36 S COcPent 1-37 S COHex 1-38 S COcHex 1-39 S CO ₂ Me 1-40 S CO ₂ Et 1-41 S CO ₂ Pr 1-42 S CO ₂ iPr 1-43 S CO ₂ Bu 1-44 S CO ₂ iBu 1-45 S CO ₂ Pent 1-46 S CO ₂ Hex ─ ───────────────

[0033]

[Table 2]

[0034]

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化合物 Compound number W X 2-1 2-1 O OMe 2-2 O OEt 2 -3 O OPr 2-4 O OiPr 2-5 O OBu 2-6 O OiBu 2-7 O OtBu 2-8 S OMe 2-9 S OEt 2-10 S OPr 2-11 S OiPr 2-12 S OBu 2 -13 S OiBu 2-14 S OtBu 中 Among the above exemplified compounds, a suitable compound is Compound No. 1-
1, 1-2, 1-3, 1-6, 1-16, 1-24, 1-25, 1-26, 1-29 or
No. 1-39, more preferably compound No. 1-1
Or the compound of No. 1-24.

[0036]

DETAILED DESCRIPTION OF THE INVENTION The 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazol-5 (4H) -one derivative or 3- (4-trifluoromethyl) of the present invention -3-Pyridyl) -1,2,4-oxadiazole-5 (4H) -thione derivative can be produced by the following step A.

(Step A)

[0038]

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In the above formula, W and X are as defined above,
Z is the same leaving group as X or a leaving group having a higher reactivity than X (when X is a halogen atom or a C ₁ -C ₆ alkoxy group, Z is preferably a C ₁ -C ₆ alkoxy group; Group,
More preferably, it is a methoxy group or an ethoxy group. ).

(Step A-1) In this step, a 4-trifluoromethylnicotinamide oxime derivative represented by the formula (III) is converted to a compound of the formula (I) in the presence of a base in an inert solvent.
V) to react with a compound represented by the formula (V) to obtain an O-substituted-4-trifluoromethylnicotinamide oxime derivative (II)
This is the step of manufacturing.

In this step, the base used is not particularly limited as long as it generally has a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; calcium hydroxide and water Hydroxides of alkaline earth metals such as magnesium oxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate; sodium and hydrogen hydride Metal hydrides such as potassium iodide; alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; triethylamine, N,
Organic bases such as N-dimethylaniline and pyridine; or organic metals such as methyllithium, butyllithium, methylmagnesium bromide, lithium diisopropylamide, and the like, preferably alkali metal carbonates and alkali metal. Bicarbonates or organic bases, more preferably sodium carbonate, potassium carbonate, pyridine or triethylamine.

The amount of the base to be used depends on the amount of the compound (III)
The amount is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, per 1 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used depends on the amount of the compound (III)
It is usually 1.0 to 20 liters per 1 mol,
Preferably, it is 1.0 to 10 liters.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually from 6 minutes to 48 hours, preferably from 10 minutes to 24 hours.

As the compound 4-trifluoromethylnicotinamide oxime used in this step, a commercially available product can be used.

(Step A-2) In this step, compound (II)
Is cyclized in the presence or absence of a base in an inert solvent to give 3- (4-trifluoromethyl-3-pyridyl) -1,2,4 represented by the general formula (I) of the present invention. This is a step of producing -oxadiazol-5 (4H) -one or 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-5 (4H) -thione.

In the present step, the base used is not particularly limited as long as it generally shows a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; calcium hydroxide and water Hydroxides of alkaline earth metals such as magnesium oxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate; sodium and hydrogen hydride Hydrides of alkali metals such as potassium iodide; sodium methoxide, sodium ethoxide and potassium te
alkoxides such as rt-butoxide; organic bases such as triethylamine, N, N-dimethylaniline and pyridine; or methyllithium, butyllithium,
Methyl magnesium bromide, organic metals such as lithium diisopropylamide, etc., preferably alkali metal carbonates, alkali metal bicarbonates or organic bases, more preferably sodium carbonate, potassium carbonate, Pyridine or triethylamine.

The amount of the base used is the same as in the compound (II) 1
It is usually 1.0 to 10.0 mol with respect to mol,
Preferably, it is 1.0 to 5.0 mol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting materials to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used depends on the amount of the compound (II)
It is usually 1.0 to 20 liters, preferably 1.0 to 10 liters, based on mol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually from -40 ° C to 150 ° C, preferably from 20 ° C to 130 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually 6 minutes to 48 hours, preferably 10 minutes to 24 hours.

The compound (I) of the present invention can be converted to the amide derivative of the present invention by the following step B.

(Step B)

[0057]

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In the above formula, W is as defined above, and Y is
A leaving group (preferably a halogen atom, more preferably a chlorine atom), and R represents an acyl group (preferably a C _{2 to} C ₈ alkylcarbonyl group or a C _{2 to} C ₈ alkoxycarbonyl group, more preferably, acetyl,
A propionyl, cyclopropylcarbonyl or methoxycarbonyl group. ).

In this step, the compound (I) of the present invention is reacted with a compound represented by the general formula (V) in an inert solvent in the presence of a base to produce the amide derivative (Ia) of the present invention. It is a process.

In the present step, the base used is not particularly limited as long as it generally has a pH of 8 or more. For example, hydroxides of alkali metals such as sodium hydroxide and potassium hydroxide; calcium hydroxide and water Hydroxides of alkaline earth metals such as magnesium oxide; carbonates of alkali metals such as sodium carbonate and potassium carbonate; bicarbonates of alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate; sodium and hydrogen hydride Hydrides of alkali metals such as potassium iodide; sodium methoxide, sodium ethoxide and potassium te
alkoxides such as rt-butoxide; organic bases such as triethylamine, N, N-dimethylaniline and pyridine; or methyllithium, butyllithium,
Organic metals such as methylmagnesium bromide and lithium diisopropylamide may be used, preferably hydrides or alkoxides of alkali metals, and more preferably sodium hydride or sodium methoxide.

The amount of the base used is 1 m of compound (I)
The amount is usually 1.0 to 10.0 mol, preferably 1.0 to 5.0 mol, relative to ol.

The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent.
For example, ethers such as diethyl ether, dimethoxyethane, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; nitriles such as acetonitrile;
Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidone; sulfoxides such as dimethylsulfoxide and sulfolane; halogenated hydrocarbons such as methylene chloride and chloroform; Esters such as ethyl acetate and ethyl propionate; aliphatic hydrocarbons such as hexane, cyclohexane and heptane; pyridines such as pyridine and picoline; or a mixed solvent thereof, preferably ether. , Halogenated hydrocarbons, esters, aliphatic hydrocarbons or aromatic hydrocarbons, more preferably tetrahydrofuran, methylene chloride, ethyl acetate or toluene.

The amount of the solvent used is 1 m of compound (I)
It is usually 1.0 to 20 liters, preferably 1.0 to 10 liters, based on ol.

The reaction temperature varies depending on the starting compound, reaction reagent, solvent and the like, but is usually -40 ° C to 150 ° C, preferably 0 to 100 ° C.

The reaction time varies depending on the starting compound, reaction reagent, solvent, reaction temperature and the like, but is usually from 6 minutes to 48 hours, preferably from 10 minutes to 24 hours.

After completion of each of the above reaction steps, the target compound of each step can be collected from the reaction mixture according to a conventional method. For example, it can be obtained by appropriately neutralizing the reaction mixture, removing any insoluble matter by filtration, adding an organic solvent immiscible with water, washing with water, and distilling off the solvent. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography. In addition, the target compound of each step may be used in the next reaction step without generation.

The compound (I) of the present invention can be converted to a salt with an acid in the presence of a solvent in addition to the above-mentioned alkali metal salt, alkaline earth metal salt or ammonium salt.

When the compound of the present invention is used as an active ingredient of a pesticide, the compound of the present invention may be used as it is, but it may be used as a carrier, a surfactant and other additives generally used for formulation as a pesticide adjuvant. Mixing auxiliary agents, for example, emulsions, suspensions, powders, granules, tablets, wettable powders, aqueous solvents, liquids, flowables, wettable powders, aerosols,
It can be formulated in various forms such as pastes, oils and emulsions. These compounding ratios are usually 0.1 to 9.0 parts by mass of the active ingredient and 10 to 99.9 parts by mass of the pesticide adjuvant.

Carriers used in the above formulation include, for example, animal and plant powders such as starch, activated carbon, soybean powder, flour, wood powder, fish powder, milk powder, and talc, kaolin, bentonite, calcium carbonate, zeolite, diatomaceous earth, Solid carriers such as mineral powders such as white carbon, clay and alumina; or water, alcohols such as isopropyl alcohol and ethylene glycol, ketones such as cyclohexane and methyl ethyl ketone, ethers such as dioxane and tetrahydrofuran, kerosene and light oil. Such as aliphatic hydrocarbons, xylene, trimethylbenzene, tetramethylbenzenemethylnaphthalene, aromatic hydrocarbons such as solvent naphtha, halogenated hydrocarbons such as chlorobenzene, acid amides such as dimethylacetamide, and glycerin ester of fatty acid Esters etc., it can be a liquid carrier such as nitriles and dimethylsulfoxide sulfur-containing compounds such as de as acetonitrile, preferably a solid carrier or liquid carrier.

The surfactants used include, for example, metal salts of alkylbenzenesulfonic acid, metal salts of dinaphthylmethanedisulfonic acid, alcohol sulfates, alkylarylsulfonates, ligninsulfonates, polyoxyethylene glycol ethers, polyoxyethylene glycol ethers It can be an ethylene alkyl aryl ether or a polyoxyethylene sorbitan monoalkylate, preferably a metal alkylbenzene sulfonic acid salt, a lignin sulfonate, a polyoxyethylene alkyl aryl ether or a polyoxyethylene sorbitan monoalkylate.

Other adjuvants include, for example, fixing or thickening agents such as carboxydimethylcellulose, gum arabic, sodium alginate, xanthan gum, guar gum, tragacanth gum and polyvinyl alcohol; antifoaming agents such as metal soaps; It may be a physical property enhancer coloring agent such as alkyl phosphate, silicone and paraffin, and is preferably guar gum or xanthan gum.

These preparations can be used as they are in actual use, or can be used after being diluted to a predetermined concentration with a diluent such as water. The application of various preparations containing the compound of the present invention or a diluent thereof is generally carried out by general application methods, that is, spraying (for example, spraying, misting, atomizing, dusting, dusting, water application) , Box application, etc.), soil application (eg, mixing, irrigation, etc.), surface application (eg, application, dressing, coating, etc.), dipping or bait and the like. Further, it is also possible to feed the livestock with the above-mentioned active ingredient mixed with feed and control the occurrence and growth of harmful insects, particularly harmful insects, in the excrement. It can also be applied by a so-called ultra-high concentration small amount spraying method. In this method, it is possible to contain 100% of the active ingredient.

The concentration of the active ingredient at the time of application of the pesticide of the present invention is usually 0.1 to 50,000 ppm, preferably 1 to 50,000 ppm.
10,000 ppm. However, the concentration of the active ingredient can be appropriately changed depending on the form of the preparation and the method of application, purpose, timing, place and occurrence of pests.For example, in the case of aquatic pests, the drug solution with the above concentration is applied to the place of occurrence. Therefore, the concentration of the active ingredient in water is lower than the above. In the case of soil mixing treatment, the amount of the pesticide of the present invention is, for example, 0.1 to 5000 g, preferably 1 to 10 g, per 10 ares as an active ingredient compound.
00 g.

It is needless to say that the compound of the present invention alone is sufficiently effective, but if necessary, fertilizers and other pesticides such as insecticides, acaricides, nematicides, fungicides, antibacterial agents, It can be mixed or used in combination with a virus agent, an attractant, a herbicide, a plant regulator, and the like, and in this case, a more excellent effect may be exhibited.

Other pesticides which can be used in combination with the compounds of the present invention include, for example, insecticides, acaricides, nematicides, fungicides, antivirals, attractants, herbicides and plant regulators. Preferably, it is an insecticide, acaricide, nematicide, fungicide or herbicide.

The insecticides used can be, for example, organophosphorus and carbamate insecticides, pyrethroid insecticides or other insecticides.

Organophosphorus and carbamate insecticides include, for example, fenthion, fenitrothion, diazinon, chlorpyrifos, oxydepphos, bamidione,
Fentoate, dimethoate, formothion, malathion, trichlorfon, thiomethone, phosmet, dichlorphos, acephate, EPBP, methyl parathion, oxydimetone methyl, ethion, dioxabenzophos, cyanophos, isoxathion, pyridafenthion, hosalone, methidathione, sulprophos, cloprophochlor. Tetrachlorvinphos, dimethylvinphos, propaphos, isofenphos, disulfoton, propenophos, pyraclofos, monocrotophos, azinphosmethyl, aldicarb, mesomil, thiodicarb, carbofuran, carbosulfan, benfracarb, fratiothiocarb, propoxur, fenobucarb, metrucarb, isoprocarb, carbaryl Pirimicarb, ethiophenecarb, Black fenthion, pirimiphos-methyl, quinalphos, chlorpyrifos-methyl, prothiofos, naled, EPN, XMC, bendiocarb, oxamyl, may be alanycarb or chlorobutyl phosphite.

The pyrethroid insecticides include, for example, permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatrin, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, prothrin, fluvalinate, cyfluthrin, cyhalothrin, flucitrin. Nate,
It can be etofenprox, cycloprothrin, tralomethrin, silafluofen, tefluthrin, bifenthrin or acrinatrine.

Other insecticides include, for example, diflubenzuron, chlorfluazuron, hexaflumuron, triflumuron, teflubenzuron, flufenoxuron, flucycloxuron, buprofezin, pyriproxyfen, lufenuron, cyromazine, methoprene, endosulfan, dia Fenthiuron, imidacloprid, fipronil, phenoxycarb, cartap, thiocyclam, bensultap, tebufenozide, chlorfenapyr, emamectin benzoate, acetamiprid, nitenpyram, pymetrozine, sodium oleate, nicotine sulfate, rotenone, metaldehyde, machine oil, T or oil It may be a microbial pesticide such as an insect pathogenic virus.

The acaricides to be used include, for example, chlorbenzylate, phenisobromolate, dicofol, amitraz, propargite, benzomate, hexthiazox, fenbutatin oxide, polynactin, quinomethionate, chlorfenson, tetradihon, abamectin , Milbemectin, Clofenthedine, Pyridabene, Fenpyroximate, Tebufenpyrad, Pyrimidifen, Fenothiocarb, Dienochlor, Ethoxazole, and Harfenprox.

The nematicide used can be, for example, phenamiphos, phosthiazate, etoprophos, methyl isothiocyanate, 1,3-dichloropropene or DCIP.

The fungicides used include, for example, thiophanate methyl, benomyl, carbendazole, thiabendazole, forvet, thiuram, ziram, zineb, maneb, manzeb, polycarbamate, iprobenphos, edifenfos, fusaride, probenazole,
Isoprothiolane, chlorothalonil, captan, polyoxin, blasticidin S, kasugamycin, streptomycin, validamycin, tricyclazole,
Pyroquilon, phenazine oxide, mepronil, flutranyl, pencyclon, iprodione, hymexazole, metalaxyl, triflumizole, triforine, triadimefon, bitertanol, fenarimol, propiconazole, simoxanil, polochloraz, pefurazoate, hexaconazole, microbutane, diclometane, diclometane, diclometane , Dithianon, fosetyl, vinclozolin, procymidone, oxadixyl,
It can be guazatine, propamocarb hydrochloride, fluazinam, oxolinic acid, hydroxyisoxazole, imibenconazole or mepanipyrim.

The herbicides used are, for example, diflufenican, propanil, dichloropicolinic acid, dicamba,
Picoloram, 2,4-D, 2,4-DB, 2,4-D
P, fluroxypyr, MCPA, MCPP, triclopyr, diclohop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, quizalofop-ethyl, norflurazon, chlorbropam, desmedifam, fenmedipham, profam, alachlor, acetochlor, Butachlor, metazachlor, metolachlor, pretilachlor, propachlor, oryzalin, trifluralin, acifluorfen, bifenox, fluorogligofen, fomesafen, halosaphen, lactofen, oxyfluorfen, chlortoluron, diuron, fluometuron, isoproturon, linuron, metabenzulone Alloxydim, Cletodim, Cycloxydim, Sethoxydim, Trakoxydim, Ima Tapil, imazamethabenz, imazapyr, imazaquin, bromoxynil, diclobenil, ioxinyl, mefenacet, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, sinosulfuron, metsulfuron-methyl, nicosulfuron, pyrimisulfuron, pyrazosulfuron-ethyl, Thifensulfuron-methyl,
Triasulfuron, tribenuron-methyl, butyrate, cycloate, gialate, EPTC, esprocalp, molinate, prosulfocalp, benthiocalp, trilate, atrazine, cyanazine, simazine, simetrine, terbutrin, terbutyrazine, hexazinone, metamitrone, metribuzine, amitriazole, amitriazole , Bentazone, cinmethirin, chromazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinclorac, quinmethac, sulfosate or tridiphane.

The compounds of the present invention include, for example, Hemiptera, Lepidoptera, Coleoptera, Diptera, Hymenoptera, Orthoptera, Termites, Thrips, Spider mites and plants It shows an excellent control effect on parasitic nematodes.
In addition, the compound of the present invention has an excellent control effect on other pests, unpleasant animals, sanitary pests and parasites.

As the insects of the order Hemiptera, for example, Riptortus clavatus, southern stink bug (Nezara viridula),
Red stink bugs (Lygus sp.), American green stink bug (Blissus leucter)
us), Nashigumbai (Stephanitis na)
shi) and other stink bugs (Heteroptera; Heteropte)
ra), leafhopper (Nephotettix)
cincticeps), leafhopper (Empoas)
ca sp. , Erythroneura sp. ,
Circulifer sp. ) And leafhoppers such as the brown planthopper (Nilaparvatalugen)
s), staghorn planthopper (Sogatalla furci)
fera), Japanese brown planthopper (Laodelfax)
grasshoppers such as striatellas), Psylla
sp. Lice such as white lice, whitefly (Bemi)
sia tabaci), Whitefly on whitefly (Tri)
whiteflies, such as Aleurodes vapororiorum, and grape aphids (Viteusv)
itifolii), peach aphid (Myzus)
persicae) and apple aphids (Aphis)
pomi), Cotton Aphid (Aphisgossy)
pii), Aphis fabae, Aphid aphid (Liphis erysimi), Potato beetle aphid (Aulacorthum sol)
ani), wheat midge aphid (Schizaphi)
aphids such as sgraminum, etc., and Pseudococcus comstoc
ki), Ruby beetle (Ceroplastesru)
bens), San Jose scale insects (Comstoc)
caespis perniciosa, Unapsis yanoensis, and other scales such as scales and scales (Rhodnius sp.).
Is mentioned.

Examples of lepidopteran pests include, for example, Hohama magnanima, Adlerophora oradina (Adoxophys orana), and Sparganothis pilarian.
a), Nasihime Shingui (Grapholitham)
olesta), Mameshin iga (Leguminiv)
ora glycinivorella), codling moth (Laspeyresia pomonella), E
ucosma sp. , Lobesia botran
a, etc., and Grape Hosohamaki (Eupoeci)
llia ambiguella), Bombalina sp. , Moths (Nemapogon granellus), squirrels (Tineapellionella), etc., ginseng molymoga (Lyonetiapruni)
folliella, etc., and the typhoon moth moth (Phylnolyctor ringoniel)
la) etc .;
Scutellaria moth, such as Cnistis citellella, and Plutella xylostell
a), Suga such as Plays citri, grape sashiba (Nokona vegale), Synanth
edon sp. Scabby, cotton red bug (P
ectinophora gossypiella),
Potato moth (Phthorimaeapercul)
ella), Stopteryx sp. Mosquitoes, peach sink moth (Carposina nipo)
nensis), Iruga (Monem)
a flavescens, etc., Japanese squid (Chilo suppressalis), and the Japanese frog (Cnaphalocrocis median)
is), Ostrinia nubilalis, Awanomeiga (Ostrinia furnacali)
s), Himuradanomeiga (Hellula unda)
lis) Honey (Galleria mellon)
ella), Elasmopalpus lignos
ellus, Loxostege scientific
moss such as is, cabbage butterfly (Pieris r)
apae) and white butterflies, Artemisia japonicus (As
pterodactyls such as Cotisselenaria, Kalehaga such as Malcosomaneustria, sparrows such as Manduca sexta, and Eupoctis pseudodoc.
onspersa), Gypsy moth (Lymantria)
dispar, etc., Hokutriga, such as Hyphantria cunea, and tobacco badworm (Heliothis vir)
escens), ball worm (Helikoverp)
a zea), Spodoptera litura (Spodopte)
ra exigua) and Helicov (Helicov)
erpa armigera), Spodoptera litura (Sp)
podoptera litura) and the armyworm (Mam)
estra brassicae), Tamanayaga (Ag)
rotis ipsilon), armyworm (Pseu)
and noctuids such as daleia separata and Trichoplusia ni.

Examples of the insects of the order Coleoptera include, for example, Anagala cuprea, Anopheles japonica, Anomala rufocuprea, and Euth.
beetles such as eolalugiceps, wire worms (Agricotes sp.), Conode
us sp. Beetles such as the beetle, and the Japanese lady beetle (Epilachna vicientoctop)
uncata), Ladybug (Epila)
ladybirds such as chna varivestis, and Tribolium cast
anemon), beetles such as beetles, Anoplophora malasiaca, and Monochamus alte
beetles such as C. rnatas, bean weevil (Acanthoscelides obect)
us), adzuki beetle (Callosobruchu)
bean weevil, such as S. chinensis, and Colorado potato beetle (Leptinotarsa decemli)
neata), corn rootworm (Diabroti)
ca sp. ), Olema o
ryzae), Tency beetle (Chaetocn)
ema concinna), Phaedon coc
hlearias, Olema melanopu
s, leaf beetles such as Dicladospa armigera, weevil weevil such as Apion godmani, and rice weevil (Lissorhoprus)
oryzophilus, cotton weevil (Ant)
weevil such as Homomus grandis, and weevil (Sitophilus Zeamais)
And weevil, bark beetle, beetle beetle, and beetle.

Examples of the dipteran insect pests include, for example, the giant crab (Tipula aino) and the rice midge (Ch).
ironomus oryzae), rice scintillation fly (Orseolia oryzae), medfly (Ceratitis capitata),
Rice Flies (Hydrellia griseol)
a), Drosophila (Drosophil)
a suzukii), Fritz fries (Oscine)
lla frit), rice flies (Chlorops)
oryzae), haricot fly (Ophiom)
yia phaseoli)
riomyza trifolii, Pegomya hyoscyami, Tanfly (Delia platura), Sorghum fry (Atherigona soccata), Musca domestica (Musca domesica)
trophilus sp. ), Fly (Stom)
oxys sp. ), Aedes aegypti (Aedes a)
egypti), Culex pipiens
ns), Anopheles sln
ensis) and Culex pipiens (Culex tr)
itaeniorhynchus).

Examples of the hymenoptera pests include, for example, wasps (Cephus sp.) And honey bees (Harm).
olita sp. ), Alaska bee (Athalia)
rosae), hornet (Vespa manda)
rina) and fire ant.

Examples of pests of the order Orthoptera include German cockroaches (Blattella germanica) and American cockroaches (Periplaneta americic).
ana), Kera (Grylotalpa afric)
ana), grasshopper (Locusta migrator)
ia migratriodes) and Melano
plus sanguinipes.

As a thrips pest, for example, Thrips thrips dor
salis) and Thrips palmi (Thrips)
palmi), Croton thrips (Helioth)
rips haemorrhoidalis, Citrus thrips (Frankliniella oc)
C. centralis) and Thrips palmi (Ha)
plothripsaculeatus).

As spider mites, for example, spider mites (T
etranychus urticae), Kanzawa spider mite (Tetranychus kanzawa),
Citrus red mite (Panonychus citri),
Apple spider mite (Panonychus ulmi), yellow mites (Eotetranychus carp)
ini), Texas Citrus Mite (Eotetran)
ychus banksi), citrus red mite (Acu)
lops pelekassi, Polyphagotarsonemus latu
s), Red-bodied spider mite (Brevipalpus s)
p. ), Robin mite (Rhizoglyphus r)
obini) and Tyrophagu
s putresentiae).

As plant parasitic nematodes, for example, sweet potato nematodes (Meloidogyne in
cognita), Negusaresenchu (Pratyl)
enchus sp. ) Soy cyst nematode (He
terodera glycines), rice squirrel nematode (Apelenchoides bess)
eyi) and pine wood nematode (Bursaphe)
Lenchus lignicolus).

As other pests, unpleasant animals, sanitary pests and parasites, for example, screaming mussel (Pomac
ea canaliculata, slugs (Inc.)
ilaria sp. ), African Maimai (Acha
Gastropods (Gastro) such as tina fulica
poda), dung beetle (Armadillidium)
sp. ), Isopoda, Isopoda, Centipede, etc. (Iso
poda), Liposcelis sp. Etc., Ctenolepisma sp. Stains such as Pulex sp. , Ctenocephalid
es sp. Fleas, etc., Trichodicts
sp. Lice such as Cimex sp. Bed lice such as bed bugs and ox tick (Boophilus micr)
opulus), Haemaphys
animal parasitic mites such as Aris longicornis and Dermatophagoides pteronyssinus.

The compounds of the present invention are also effective against organophosphorus compounds, carbamate compounds, synthetic pyrethroid compounds, acylurea compounds or pests which are resistant to existing insecticides.

The compound of the present invention will be specifically described below with reference to Examples, Preparation Examples and Test Examples, but the present invention is not limited to these.

[0097]

【Example】

[0098]

Example 1 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-5 (4H)-
ON (Compound No. 1-1) (1) N- (ethoxycarbonyloxy) -4-trifluoromethylpyridine-3-carboxamidine (Compound No. 2-2, Step A-1)

[0099]

Embedded image

4- (trifluoromethyl) pyridine-3
-Carboxamide oxime (0.41 g) and triethylamine (0.33 ml) in dichloromethane (4 m
l), ethyl chlorocarbonate (0.21 ml) was added to this solution at 0 ° C, and the mixture was stirred at the same temperature for 2 hours.
After completion of the reaction, the reaction solution was washed with a saturated saline solution and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4) to obtain the title compound (0.42 g, yield 76%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.92 (1H, s), 8.90 (1H, d, J
= 5.9Hz), 7.62 (1H, d, J = 4.8Hz), 5.19 (2H, brd.s),
4.34 (2H, q, J = 7.1Hz), 1.38 (3H, t, J = 7.1Hz). Melting point: 155-158 ° C. (2) 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazol-5 (4H) -one (Compound No. 1-1, Step A-2)

[0101]

Embedded image

The N- (ethoxycarbonyloxy) -4-trifluoromethylpyridine-3-carboxamidine (0.42 g) obtained in (1) was dissolved in xylene (9 ml), and the mixture was heated under reflux for 5 hours. The solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4) to obtain the title compound (0.23 g, yield 66%). ¹ H-NMR (CDCl ₃ ) δ (ppm): 9.08-9.07 (2H, m), 7.77 (1H,
d, J = 5.1 Hz). Melting point: 121-123 ° C.

[0103]

Example 2 3- (4-trifluoromethyl-3-pyridyl) -4-methoxycarbonyl-1,2,4-oxadiazol-5 (4H) -one (compound No. 1-16,
Step B)

[0104]

Embedded image

The 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazol-5 (4H) -one (68.2 mg) obtained in Example 1 was dissolved in toluene (1 ml). Sodium hydride (13.0 mg in 60% mineral oil) and methyl chlorocarbonate (0.03 m
l) was added at 0 ° C, and the mixture was heated and stirred at 90 ° C for 1 hour. A saturated saline solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off, and the resulting residue was subjected to thin-layer silica gel chromatography (elution solvent: ethyl acetate /
Purified with hexane = 1/2) to give the title compound (25.0).
mg, 29% yield). _{^{1 H-NMR (CDCl 3)}} δ (ppm): 9.05 (1H, d, J = 5.1Hz), 8.84
(1H, s), 7.72 (1H, d, J = 5.1 Hz), 3.92 (3H, s). Melting point: 125-127 ° C.

[0106]

Example 3 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-5 (4H)-
Thione (Compound No. 1-24, Steps A-1 and A-2)

[0107]

Embedded image

4- (trifluoromethyl) pyridine-3
-Carboxamide oxime (0.10 g) was dissolved in acetonitrile (2 ml) and thiocarbonyldiimidazole (0.14 g) and 1,8-diazabicyclo [5.
4.0] -7-undecene (0.29 g) was added at room temperature, and the mixture was stirred at the same temperature for 3 hours. A saturated saline solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was distilled off, and the obtained residue was dissolved in toluene (1.0 ml).
The mixture was heated and stirred at 100 ° C. for 20 minutes. The solvent was distilled off, and the obtained residue was purified by thin-layer silica gel chromatography (elution solvent: ethyl acetate / hexane = 1/1) to obtain the title compound (18.3 mg, yield: 15%). . ¹ H-NMR (CDCl ₃ ) δ (ppm): 8.93 (1H, s), 8.89 (1H, d, J
= 4.8Hz), 7.62 (1H, d, J = 5.1Hz), 5.91 (1H, brd.s). Melting point: 157-159 ° C. Further, the following compounds were produced according to Example 2.

[0109]

Example 4 3- (4-trifluoromethyl-3-pyridyl) -4-pivaloyl-1,2,4-oxadiazol-5 (4H) -one (Compound No. 1-11)

[0110]

Embedded image

¹ H-NMR (CDCl ₃ ) δ (ppm): 9.00 (1H, d, J =
5.1Hz), 8.84 (1H, s), 7.68 (1H, d, J = 5.1Hz), 1.40
(9H, s). Melting point: 93-95 ° C.

In the following preparation examples, the types and mixing ratios of the compounds and auxiliary agents are not limited to these, and can be changed in a wide range. Also, in the following description,% indicates mass percentage.

[0113]

Formulation Example 1 Emulsion Compound No. 1-1 (5%) was added to xylene (4%).
2.5%) and dimethyl sulfoxide (42.5%), and then dissolved, and then mixed with a mixture of polyoxyethylene castor oil ether and calcium alkylbenzene sulfonate (8: 2, 10%) to obtain an emulsion. . The drug is diluted with water and used as a spray liquid.

[0114]

Formulation Example 2 Wettable powder Compound No. 1-1 (5%) was added to kaolin (79%).
%) And diatomaceous earth (10%), then sodium lauryl sulfate (3%) and sodium ligninsulfonate (3%), and pulverize to obtain a wettable powder. This drug is diluted with water and used as a spray liquid.

[0115]

Formulation Example 3 Dust A mixture of talc and calcium carbonate (1: 1, 99%) is added to the compound of Compound No. 1-1 (1%), and after mixing, the mixture is pulverized to obtain a dust. To use.

[0116]

Formulation Example 4 Granules Compound No. 1-1 (2%) was mixed with bentonite fine powder (30%), talc (66%) and sodium ligninsulfonate (2%), and water was added. Knead until uniform. Next, granulate through a granulator and granulator,
Granules having a particle size of 0.6 to 1.0 mm are obtained by passing through a dryer and a sieve. Spray this agent as it is on the soil surface.

[0117]

Formulation Example 5 Oil Agent The compound of Compound No. 1-1 (0.1%) is dissolved in white kerosene to make the whole 100% to obtain an oil agent.

[0118]

Test Example 1 Insecticidal test of peach aphid Water (30 ml) was placed in a beaker, and one leaf of Komatsuna was placed in a beaker so that the petiole was immersed in water. Release five peach peach aphids on the back of the leaf of Komatsuna,
They were born. Two days after release, the adults were removed and the larvae were counted.

Surfactant Newcol NE-710F
2% (registered trademark, manufactured by Nippon Emulsifier Co., Ltd.) was dissolved in 98% aqueous acetone (95% aqueous) to obtain a solution 1. Next, 0.2% of dispersant Gohsenol GLO5-S (registered trademark, manufactured by Nippon Emulsifier Co., Ltd., 0.2% aqueous solution) was added to water 9
The solution was dissolved in 9.8% to obtain a solution 2.

The compound of the present invention (8 mg) was added to the solution 1
(0.4 ml), the solution 2 (0.4 ml) and water (8
ml), and diluted with water so that the compound of the present invention becomes 100 ppm and 10 ppm, respectively.
It was added to 1%. ｝.

8 ml of the above chemical solution was sprayed on the leaves of the komatsuna using a rotary spray tower. Return the komatsuna leaf to the beaker,
25 ° C., 16 hours: light, 8 hours: dark.
Five days after spraying, the number of dead insects was examined, and the mortality was calculated. Table 3 shows the results.

A similar test was performed using compounds described in the literature as comparative compounds. Comparative compound a is WO 98579
Compound No. 694 described in No. 69 and JP-A-2000-
No. 38385, Compound No. 4 and Comparative Compound b is Compound No. 742 described in WO 9857969.
And Comparative Compound c is Phosphorus Sulfur and Silicon
n, 1991, 62 , 47-51.

[0123]

[Table 3] Peach aphid insecticidal test ──────────────────────────────────── Test number Test compound Death Insect rate (%) 薬 剤 Chemical concentration of spray liquid 100ppm 10ppm ────────────────────── ────────────── 1 Compound 100 of Example 1 (Compound No. 1-1) 100 100 2 Compound 100 of Example 3 (Compound No. 1-24) 100 ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ ─ 3 Comparative compound a 3 0 4 Comparative compound b 0 0 5 Comparative compound c 14 10 ────────────────────構造 The structure of the test compound is shown below.

[0124]

Embedded image

[0125]

According to the present invention, 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-5 is used.
A (4H) -one derivative or a 3- (4-trifluoromethyl-3-pyridyl) -1,2,4-oxadiazole-5 (4H) -thione derivative, a salt thereof and an amide derivative thereof are, for example, semi-anionic derivatives. Against a wide range of pests such as Lepidoptera, Lepidoptera, Coleoptera, Diptera, Hymenoptera, Orthoptera, Termites, Thripidae, Spider mites and plant parasitic nematodes And excellent control effect.

Claims (5)

[Claims] 1. A compound of the general formula [Wherein, W represents an oxygen atom or a sulfur atom. Or a salt or amide derivative thereof. 2. The compound according to claim 1, wherein W is an oxygen atom, a salt thereof or an amide derivative thereof. 3. The compound according to claim 1 or 2, wherein the amide derivative is an amide derivative in which a C ₂ -C ₈ alkylcarbonyl group or a C ₂ -C ₈ alkoxycarbonyl group is bonded to a nitrogen atom, a salt thereof or an amide thereof. Derivatives. 4. The compound according to claim 1, wherein the amide derivative is an amide derivative having an acetyl, propionyl, cyclopropylcarbonyl or methoxycarbonyl group bonded to a nitrogen atom, a salt thereof or an amide derivative thereof. 5. One of the first to fourth aspects
A pesticide comprising the compound according to any one of the above, a salt thereof or an amide derivative thereof as an active ingredient.