JPH0686442B2 - New heterocyclic compound - Google Patents

Description

The present invention relates to novel heterocyclic compounds, a process for their preparation and their use as insecticides.

West German Patent No. 1,019,122 known before the filing date of the present application has the formula: In the formula, n represents 0 or 1, and R _{1 to} R ₇ represent a hydrogen atom, alkyl, aryl, alkylaryl, aralkyl or alkoxy, and it is described that the compound represented by the formula has bactericidal activity.

The present inventors have now discovered the existence of a novel heterocyclic compound of formula (I) below and have succeeded in its synthesis. Furthermore,
It has been discovered that the compounds of formula (I) exhibit insecticidal activity and are useful, for example, as insecticides.

formula: In the formula, W represents a heterocyclic group which contains a heteroatom arbitrarily selected from N, O and S, at least one of which is an N atom and which may be optionally substituted, and R is A hydrogen atom or an alkyl group having 1 to 4 carbon atoms is shown, A is an ethylene group or a trimethylene group, and Y and Z are an oxygen atom, a sulfur atom, an imino group or a methylene group, and Z is further May represent a methylene group together with the carbon atom to which is bonded.

The compound of the formula (I) of the present invention can be synthesized, for example, by the following method.

Process a): In [-((I)], Y represents an oxygen atom, a sulfur atom or an imino group, and Z represents an oxygen atom or a sulfur atom. Let Y be Y ¹ and Z be Z ¹ ] Formula: Wherein W, R, and A are the same as above, and Y ¹ is an oxygen atom,
A compound represented by, which represents a sulfur atom or an imino group, and a compound represented by the formula: Wherein Z ¹ represents an oxygen atom or a sulfur atom, and T and T ′ represent halogen, alkoxy or phenoxy, characterized by reacting with a compound represented by the formula: In the formula, W, R, A, Y ¹ and Z ¹ are the same as defined above, and a process for producing a novel heterocyclic compound.

Manufacturing method b):-Formula: Wherein W, R and A are the same as above, and Hal is a halogen atom, and a compound of the formula: Z ¹ ═C = Y ¹ (V) wherein Y ¹ and Z ¹ are as described above. Characterized by reacting with a compound represented by
A method for producing the compound of formula (Ia).

Process c):-[In the formula (I), when Z represents an oxygen atom, an imino group or a methylene group, and when Z represents a methylene group together with the carbon atom to which it is bonded. Let Z be Z ² ] Formula: In the formula, W, R and Hal are the same as above, and a compound represented by the formula: Wherein A and Y are the same as defined above, and Z ² is an oxygen atom, an imino group or a methylene group, and is reacted with a compound represented by the formula: In the formula, W, R, A, Y and Z ² are the same as defined above, and a method for producing the compound.

The heterocyclic compound of formula (I) of the present invention exhibits a strong insecticidal action.

According to the invention, the compounds of the formula (I) surprisingly show a very outstanding insecticidal action, in comparison with, for example, fungicidally active compounds similar to the compounds according to the invention described in the aforementioned publications. I knew I forgot.

In the compound of formula (I) of the present invention, W preferably contains 1 to 2 heteroatoms selected from N, O and S,
And 5 to 6 in which at least one of them is a nitrogen atom
Member heterocyclic group, wherein the group is halogen, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons, haloalkyl having 1 to 4 carbons, alkylthio having 1 to 4 carbons, carbon Optionally substituted by a haloalkoxy having 1 to 4 carbon atoms or a haloalkylthio having 1 to 4 carbon atoms, R represents a hydrogen atom or a methyl group, A represents an ethylene group or a trimethylene group, Y and Z represent an oxygen atom, a sulfur atom, an imino group or a methylene group.

Further, in formula (I), it is preferable that W contains 1 to 2 heteroatoms selected from N, O and S,
And 5 to 6 in which at least one of them is a nitrogen atom
A membered heterocyclic group, wherein the group is fluoro, chloro, bromo, methyl, ethyl, methoxy, methylthio,
It may be substituted with any one selected from trifluoromethyl and trifluoromethoxy.

R represents a hydrogen atom, A represents an ethylene group or a trimethylene group, Y represents an oxygen atom, a sulfur atom, an imino group or a methylene group, and Z represents a sulfur atom.

Specific examples of the compound of the formula (I) of the present invention include the following compounds.

3- (2-chloro-5-pyridylmethyl) thiazolidine-2-thione, 3- (2-chloro-5-pyridylmethyl) tetrahydro-1,3-thiazin-2-thione, 3- (2-chloro-5) -Pyridylmethyl) oxazolidin-2-one, 3- (2-chloro-5-pyridylmethyl) tetrahydro-1,3-oxazin-2-one.

In the production method a), when N- (2-chloro-5-pyridylmethyl) ethylenediamine and diphenyl carbonate are used as raw materials, the production method a) can be represented by the following reaction formula. it can.

In the production method b), as a raw material, for example, N-2-chloroethyl-N- (2-chloropyridin-5-ylmethyl)
When amine and carbon disulfide are used, the production method b) can be represented by the following reaction formula.

In the production method c), as a raw material, for example, 2-chloro-
When 5-chloromethylthiazole and 2-oxazolidinone are used, the production method c) can be represented by the following reaction formula.

In the above production method a), the compound of the formula (II) as a raw material means one based on the above definitions of W, R, A and Y ¹ .

In formula (II), W, R, and A preferably have the same meanings as defined above, and Y ¹ preferably represents an oxygen atom, a sulfur atom or an imino group.

The compound of formula (II) is, for example, a known compound before the application of the present invention described in JP-A-60-218,336 and JP-A-61-178981.
Specific examples thereof include N- (2-chloro-5-pyridylmethyl) aminoethanethiol, N- (2-chloro-5-pyridylmethyl) aminopropanethiol, N- (2-chloro-5-pyridylmethyl). ) Aminoethanol, N- (2-chloro-5-pyridylmethyl) ethylenediamine and the like can be exemplified.

Similarly, the compound of the formula (III) as a raw material is the above Z ¹ , T and T ′.
Means based on the definition of.

In formula (III), Z ¹ preferably represents an oxygen atom or a sulfur atom, T and T ′ are preferably phenoxy,
Indicates chloro or methoxy.

The compound of the formula (III) is well known in the field of organic chemistry, and specific examples thereof include diphenyl carbonate, phosgene, thiophosgene, diethyl carbonate and the like.

In the production method b), the compound of the formula (IV) as a raw material means one based on the above definitions of W, R, A and Hal.

In formula (IV), W, R and A preferably have the same meanings as defined above, and Hal preferably represents chlorine or bromine.

The compound of the formula (IV) can be obtained by halogenating the corresponding substituted aminoalkanol known in the present application by a conventional method with a halogenating agent such as thionyl chloride.

Similarly, the compound of the formula (V) as a raw material means the compound based on the definition of Y ¹ and Z ¹ .

In formula (V), Y ¹ and Z ¹ preferably have the same meaning as defined above.

The compounds of formula (V) are already well known compounds,
Specific examples thereof include carbon disulfide and carbonyl sulfide.

In the production method c), the compound of the formula (VI) as a raw material means one based on the above definitions of W, R and Hal.

In formula (VI), W and R preferably have the same meanings as defined above, and Hal preferably represents chlorine or bromine.

The compound of formula (VI) is a known compound before the application of the present application, and specific examples thereof include 2-chloro-5.
Examples include -chloromethylpyridine and 2-chloro-5-chloromethylthiazole.

Similarly, the starting compound of the formula (VII) means the compound based on the definitions of A, Y and Z ² .

In formula (VII), A and Y preferably have the same meanings as defined above, and Z ² preferably represents an oxygen atom, an imino group or a methylene group.

The compounds of formula (VII) are already well known compounds. For example, 2-oxazolidinone is described in Ber. (Berichte), vol. 21, p. 58, tetrahydro-1,3-oxazin-2-one is described in West German patent 858402, and
-Imidazolidinone is described in J. Chem. Soc. (Journal of Chemical Society), 1929, p. 50,
Or, tetrahydropyrimidin-2-one is J. Am. Chem.
Soc. (Journal of American Chemical Society), Vol. 71, pp. 766-770. These compounds are also obtained, for example, by reaction of the corresponding aminoalkanol or alkylenediamine with diphenyl carbonate.

2-Thiazolidinone is described in J. Chem. Soc., 1952, pages 3094-3102, oxazolidine-2-thione is described in J. Ger, Che.
m. (The Journal of The Jerman Chemistry), 7
Vol., 1495-1500, imidazolidine-2-thione is described in J. Am. Chem. Soc., 63, 1058-1060, tetrahydropyrimidine-2-thione is described in U.S. Pat.
No. 2544746, thiazolidine-2-thione is
Tetrahydro-1,3 as described in U.S. Pat.
-Thiazin-2-thione, J. Chem. Soc., 1943, 243-
Described on page 249, these compounds can be obtained, for example, by reaction of the corresponding alkylenediamines, aminoalkanols or aminoalkanethiols with carbon disulfide or thiophosgene. Here, the 2-thione type is tautomeric and synonymous with the 2-mercapto type.

2-Amino-2-thiazoline is described in J. Am. Chem. Soc., 63.
2-Amino-5,6-dihydro-1,3-thiazine is described in Angew. Chem. (Angevante Fuemii), vol. 64, p. 643, and cyclic guanidine. The classes are described in J. Am. Chem. Soc., 77, 761-762.

2-Pyrrolidinone and 2-piperidinone are known, and thiazolidine, imidazolidine, pyrrolidine and the like are also well known.

The compound of the formula (I) of the present invention can be present as a tautomer when Y in the formula (I) represents an imino group, and is included in the compound of the present invention. That is, In carrying out the process a) mentioned above, use may be made, as suitable diluent, of any inert solvent.

Examples of such diluents are aliphatic, cycloaliphatic and aromatic hydrocarbons, which may optionally be chlorinated, such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene. Chloride, chloroform, carbon tetrachloride, ethylene chloride and trichloroethylene, chlorobenzene; other ethers such as diethyl ether, methyl ethyl ether, di-iso-propyl ether, dibutyl ether, propylene oxide, dioxane,
Tetrahydrofuran; Ketones such as acetone, methyl ethyl ketone, methyl-iso-propiniketone, methyl-iso-butyl ketone; Nitriles such as acetonitrile, propionitrile, acrylonitrile; Alcohols such as methanol, ethanol, iso-propanol, butanol, ethylene glycol; Mention may be made of esters such as ethyl acetate, amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfones, sulfoxides such as dimethylsulfoxide, sulfolane; and bases such as pyridine.

The above method can be carried out within a wide temperature range. For example, it can be carried out between about -20 ° C and the boiling point of the mixture, preferably between about 0 and about 100 ° C. Further, the reaction is preferably carried out under normal pressure, but it is also possible to operate under increased pressure or reduced pressure.

In carrying out the above-mentioned production method, for example, an equimolar amount of the compound of the formula (III) to about 1 mol of the compound of the formula (II) to about
The desired novel compound of formula (I) can be obtained by refluxing a 1.2-fold molar amount, preferably an equimolar amount to about 1.1-fold molar amount in an inert solvent.

Furthermore, in the formula (III), when T and T'are halogens, inorganic and organic bases can be used.

In carrying out the process b), suitable diluents may include the same inert solvents as those exemplified in the process a).

The above production method b) can be carried out within a wide temperature range, for example, about -20 ° C to about 100 ° C, preferably about 0 ° C to about 80 ° C.

Further, the reaction is preferably carried out under normal pressure, but it may be carried out under pressure or reduced pressure.

In carrying out the production method b), for example, the compound of the formula (V) is used in an equimolar amount to a small excess with respect to 1 mol of the compound of the formula (IV), and it is used in the presence of an inorganic or organic base. The desired compound of formula (I) can be obtained by reacting in an active solvent.

In carrying out the above-mentioned production method (c), suitable diluents include water, inert organic solvents excluding alcohols among the examples in the production method a), and further, as a base,
Examples thereof include hydrides such as sodium hydride and potassium hydride, and potassium carbonate and sodium hydroxide.

The above-mentioned production method c) can be carried out within a wide temperature range, for example, about 0 ° C to about 100 ° C, preferably about 10 ° C.
It can be carried out between 0 ° C and about 50 ° C.

Further, the reaction is preferably carried out under normal pressure, but it may be carried out under pressure or reduced pressure.

In carrying out the above-mentioned production method, for example, with respect to 1 mol of the compound of the formula (VII), sodium hydride as a base is about 1.1 to 1.2 times the molar amount, and the compound of the formula (VI) is at an equimolar amount to The desired compound of formula (I) can be obtained by reacting about 1.2-fold molar amount, preferably equimolar amount to about 1.1-fold molar amount in an inert solvent such as dimethylformamide.

The compound of formula (I) of the present invention exhibits a strong insecticidal action.
Therefore, they can be used as insecticides. Then, the active compound of formula (I) of the present invention exerts a proper controlling effect against harmful insects without giving phytotoxicity to cultivated plants. Further, the compound of the present invention can be used for controlling a wide variety of pests, harmful sucking insects, biting insects and other plant parasitic pests, storage pests, sanitary pests and the like, and can be applied for exterminating and eradicating them.

Examples of such pests include the following pests. Examples of insects include Coleoptera pests such as azuki bean weevil (Callosobruchus chinensis), a weevil (Sitophilus zeamais), and a peanut beetle (Tr
ibolium castaneum), Yellow-tailed ladybird (E)
pilachna vigitioctomaculata), Red-breasted beetle (Agriotes fuscicollis), Red beetle (Anomal)
a rufocuprea), Colorado potato beetle (Leptinotar)
sa decemlineata), Diablotheca (Diabrotica sp.
p.), pine woodpecker (Monochamus alternatu)
s), rice weevil (Lissorhoptrus oryzophilu)
s), flat beetle (Lyctus bruneus); Lepidoptera, for example, gypsy moth (Lymantria dispar), plum bug (Malaco)
soma neustria), Pteris rapae, Spodoptera litura, Spodoptera litura, Mamestra br
assicae), Nikameichiyu (Chilo suppressalis),
Pyrausta nubilalis, Ephestia cautella, Adoxoph
yes orana), Codling moth (Carpocapsa pomonella),
Cabbage moth (Agrotis fucosa), Honey moth (Galleria)
mellonella), diamondback moth (Plutella maculipennis), Heliothis virescens, citrus fruit moth (Phyllocnistis citrella); Scale insects (Unaspis yanonensis), green peach aphids (Myzus)
persicae), apple aphid (Aphis pomi), cotton aphid (Aphis gossypii), radish aphid (Rhopalosiphum pseudobrassicas), nasi gumbai (S
tephanitis nashi), blue stink bug (Nezara spp.),
Bed Bug (Cimex lectularius), Whitefly (Trialeurodes vaporariorum), Whitefly (Psylla)
spp.); Orthoptera, for example, German cockroaches (Blatella germanica), American cockroaches (Periplaneta americana), Gera (Gryllotalpa a)
fricana), grasshopper (Locusta migratoria migratoriode
s); Isoptera, for example, Yamato termite (Deucotermes speratus), Coptotermes formosanus; Diptera, for example, Musca domestica, Aedes
aegypti), sandfly (Hylemia platura), Culex pipiens, Anopheles sin
ensis), Culex tritaeniorhynchu
s), etc.

Furthermore, in the veterinary medicine field, the novel compounds of the present invention are effective for use against various harmful animal parasites (endo- and ectoparasites), such as insects and helminths. Examples of such animal parasites include the following pests.

Examples of insects include the fruit fly (Gastrophilus spp.) And the sand fly (Stomoxys).
spp.), white lice (Trichodectes spp.), reed turtle (R
hodnius spp.), dog flea (Ctenocephalides canis)
Etc. can be mentioned.

In the present invention, a substance having an insecticidal action against insects including all of them may be called an insecticide.

The active compound of formula (I) of the present invention can be made into a usual pharmaceutical form. And as such forms, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active compound infiltration-natural and synthetic, microcapsules, seed coatings, formulations with combustion devices (For example, fumigation and fumigation cartridges, cans and coils for combustion equipment), and ULV [cold mist (cold mis
t), warm mist].

These formulations can be manufactured by a known method.
Such a process comprises, for example, applying an active compound to a developing agent, ie a liquid diluent; a liquefied gas diluent; a solid diluent or carrier, optionally a surfactant, ie an emulsifier and / or dispersant and / or Or by using a foam forming agent and mixing.

If water is used as the developing agent, for example, organic solvents can also be used as auxiliary solvents.

Examples of the liquid diluent or carrier include aromatic hydrocarbons (eg, xylene, toluene, alkylnaphthalene, etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (eg, chlorobenzenes, ethylene chloride, chlorinated compounds). Methylene etc.), aliphatic hydrocarbons [eg cyclohexane etc., paraffins (eg mineral oil fraction etc.)], alcohols (eg butanol, glycol and their ethers, esters etc.), ketones (eg acetone,
Mention may also be made of methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strongly polar solvents (eg dimethylformamide, dimethylsulfoxide etc.) and water.

The liquefied gas diluent or carrier is a gas at room temperature and atmospheric pressure, examples of which include aerosol propellants such as butane, propane, nitrogen gas, carbon dioxide, and halogenated hydrocarbons.

As the solid diluent, soil natural minerals (for example, kaolin, clay, talc, chiyoke, quartz, attapal guide, montmorillonite, diatomaceous earth, etc.), soil synthetic minerals (for example, highly dispersed silicic acid, alumina, silicates, etc.) Can be mentioned.

Solid carriers for granules include ground and fractionated rocks (eg, calcite, marble, pumice, sepiolite, dolomite, etc.), synthetic particles of inorganic and organic powders, and organic materials (eg sawdust, Coconut seeds, corn cobs, tobacco stems, etc.) can be mentioned.

Emulsifiers and / or foaming agents include nonionic and anionic emulsifiers [eg, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid alcohol ether (eg, alkylaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aryl sulfone] Acid salt, etc.)], and albumin hydrolysis products.

Dispersants include, for example, lignin sulfite waste liquor and methylcellulose.

Adhesives may also be used in the formulation (powder, granules, emulsions), such adhesives including carboxymethyl cellulose and natural and synthetic polymers (eg gum arabic, polyvinyl alcohol and polyvinyl acetate). You can

Colorants can also be used, such as inorganic pigments (for example iron oxide, titanium oxide and Prussian blue) and organic dyes such as alizarin dyes, azo dyes or metal phthalocyanine dyes, and also iron. , Manganese, boron, copper, cobalt, molybdenum, zinc and their salts.

The formulation generally comprises from 0.1 to 95% by weight of the active ingredient,
Preferably 0.5 to 90% by weight can be contained.

The formula (I) active compounds of the present invention are in their commercially useful formulations and in the use forms prepared according to these formulations other active compounds, such as insecticides, baits, fungicides,
It can also be present as a mixture with acaricides, centrifuges, fungicides, growth regulators or herbicides. Here, examples of the vapor insecticide include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, and insecticidal substances produced by microorganisms.

Further, the active compound of formula (I) of the present invention can be present as a mixture with a synergist, and such preparations and usage forms can include those which are commercially useful. The synergist is a compound which amplifies the action of the active compound, which need not be active in and of itself.

The content of the active compounds of the formula (I) according to the invention in the commercially useful use forms can be varied within wide limits.

Useful concentrations of the active compounds of formula (I) according to the invention are, for example:
0.0000001 to 100% by weight, preferably 0.00001
~ 1% by weight.

The compound of formula (I) of the present invention can be used by a usual method adapted to the use form.

When used as hygiene pests, pests on stored materials, active compounds are distinguished by their good residual stability in wood and soil, as well as their good stability to alkalis on lime materials. ing.

Next, the contents of the present invention will be specifically described with reference to Examples.
The present invention should not be limited to this.

Manufacturing Example: Example 1 (Compound No. 1) N-2-chloroethyl-N- (2-chloro-5-pyridylmethyl) amine hydrochloride (4.8 g) was added to ethanol (30 ml).
And add carbon disulfide (1.8 g) at room temperature. Subsequently, a 20% ethanol solution of potassium hydroxide (12.3 g) is added to this solution while stirring so that the temperature does not exceed 30 ° C. After adding, stir at room temperature for a while, then
Reflux for 30 minutes.

After concentrating the alcohol under reduced pressure, dichloromethane is added to the residue and washed with water. After concentrating dichloromethane, the residue is purified by silica gel column chromatography to obtain the desired 3- (2-chloro-5-pyridylmethyl) thiazolidine-2-thione (2.2 g). mp.75-80 ° C Example 2 (Compound No. 6) 60% oily sodium hydride (0.8 g) was added to a solution of 2-oxazolidine (1.7 g) in 20 ml of dimethylformamide.
Add below ℃. Stir at room temperature until the evolution of hydrogen stops,
Then 2-chloro-5-chloromethylthiazole (3.4 g)
Is added little by little at room temperature. After the addition is complete, the contents are heated to 50 ° C.
The reaction is completed by stirring for 1 hour. After allowing to cool, the contents are poured into ice water and extracted with dichloromethane. If the dichloromethane layer is dehydrated and then concentrated, the desired product is obtained as crystals, so the product is washed with a small amount of ether and dried to obtain the desired product (1.7 g).

mp.75-78 ° C Example 3 A solution of N- (2-chloro-5-pyridylmethyl) ethylenediamine (1.9 g) and diphenyl carbonate (2.1 g) in dioxane (30 ml) is refluxed for 24 hours. After evaporating the solvent under reduced pressure, the volatile matter was removed at 1 mmHg and 80 ° C. to obtain the desired product as crystals, which was washed with ether and dried to obtain the desired product (1.3 g). mp.141-144 ° C Example 4 (Compound No. 34) 2-chloro-5-chloromethylpyridine (1.6 g), 2-
A solution of aminothiazoline (1.0 g) in ethanol (20 ml)
Reflux for 48 hours. When ethanol is concentrated under reduced pressure, the desired product is obtained as the hydrochloride, so if the product is washed well with ether and dried, the desired product (2.3 g) is obtained as the hydrochloride.

mp.214-215 ° C Example 5 (Compound No. 33) A mixture of 2-chloro-5-chloromethylpyridine (1.6 g), thiazolidine (0.9 g), anhydrous potassium carbonate (1.4 g) and acetonitrile (20 ml) is refluxed for 3 hours while stirring. Subsequently, acetonitrile is concentrated under reduced pressure, dichloromethane is added to the residue, and the mixture is washed with water. The dichloromethane layer is dehydrated, and dichloromethane is distilled off under reduced pressure to obtain the target substance (2.0 g) as a colorless oil. N ²⁰ _D 1.6090 Formula (I) synthesized according to the methods of Examples 1 to 5 above.
The compounds of the present invention are shown in Table 1 together with the compounds of Examples 1 to 5.

Biological test example: Comparative compound Example 6 (Biological test) Test against organophosphorus agent resistant leafhopper Greenhouse Preparation of reagent solution Solvent: 3 parts by weight of xylol Emulsifier: 1 part by weight of polyoxyethylene alkylphenyl ether Active to make suitable active compound formulations 1 part by weight of the compound was mixed with the above amount of solvent containing the above amount of emulsifier and the mixture was diluted with water to the specified concentration.

Test method: To a rice plant having a plant height of about 10 cm planted in a pot having a diameter of 12 cm, 10 ml of a diluted solution of the active compound prepared as above at a predetermined concentration was sprayed per pot. After spraying the spray solution, cover it with a wire net with a diameter of 7 cm and a height of 14 cm, release 30 female adults of the leafhopper leafhopper, a strain that is resistant to the organophosphorus agent, and place it in a temperature-controlled room for 2 days. Insect kill rates were calculated.

The results are shown in Table 2 with a representative example.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C07D 417/06 213 9051-4C 263 9051-4C // A01N 43/40 101 C 9159-4H 43 / 50 G 9159-4H 43/76 9159-4H 43/78 F 9159-4H 43/86 102 9159-4H

Claims (3)

[Claims] 1. A formula: In the formula, W represents a heterocyclic group which contains a heteroatom arbitrarily selected from N, O and S, at least one of which is an N atom and which may be optionally substituted, and R is A hydrogen atom or an alkyl group having 1 to 4 carbon atoms is shown, A is an ethylene group or a trimethylene group, and Y and Z are an oxygen atom, a sulfur atom, an imino group or a methylene group, and Z is further The novel heterocyclic compound represented by: may represent a methylene group together with the carbon atom to which is bonded. 2. A 5- or 6-membered heterocyclic group in which W contains 1-2 heteroatoms selected from N, O and S, and at least 1 of which is a nitrogen atom, wherein: The group includes halogen, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons, haloalkyl having 1 to 4 carbons, alkylthio having 1 to 4 carbons, haloalkoxy having 1 to 4 carbons, and 1 carbon. Optionally substituted by any one selected from haloalkylthio of 4 to 4, R represents a hydrogen atom or a methyl group, A represents an ethylene group or a trimethylene group, and Y and Z represent an oxygen atom, a sulfur atom, or imino. The compound according to claim 1, which represents a group or a methylene group. 3. A 5- to 6-membered heterocyclic group in which W contains 1-2 heteroatoms selected from N, O and S, and at least one of them is a nitrogen atom, wherein: The group is fluoro, chloro, bromo, methyl, ethyl, methoxy,
It may be substituted with any one selected from methylthio, trifluoromethyl and trifluoromethoxy, R represents a hydrogen atom, A represents an ethylene group or trimethylene group, and Y represents an oxygen atom, a sulfur atom or an imino group. Or a methylene group and Z is a sulfur atom.