JPS6229594A - Thiazine ring-containing organic phosphorous compound - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula I (R<1> and R<2> are lower alkoxy, lower alkynyloxy, lower alkylthio or arylthio; R<3> and R<4> are H or lower alkyl; R<5>-R<7> are H, lower alkyl, halogen or CF3; Y is methine or N; n is 1 or 2). EXAMPLE:2-( 2,4-Dichlorobenzylimino )-5,5-dimethyl-3,4,5,6-tetrahydro-2H -1,3-thia zine-3-thiolphosphonic acid O-methyl,S-iso-butyl ester. USE:An insecticide. PREPARATION:A compound shown by the formula II is reacted with a compound (e.g., O-methyl S-iso-butylthiophosphoric acid chloride, etc.,) shown by the formula III (Z is eliminable group) preferably in a solvent (e.g., toluene, etc.,) in the presence of a base (e.g., triethylamine, etc.,) at 20-80 deg.C for 2-8hr.

Description

DETAILED DESCRIPTION OF THE INVENTION Industrial Applications The present invention relates to organophosphorus compounds having insecticidal effects. More specifically, the present invention relates to novel organophosphorus compounds having a thiazine ring, methods for producing the same, and insecticides containing them.

BACKGROUND OF THE INVENTION A large number of insecticides are in use today, but there is a desire to develop new insecticides that have better insecticidal effects and are less toxic to humans and livestock. The present applicants conducted intensive research in order to obtain a compound that can be used as an active ingredient in such insecticides, and first synthesized a new phosphonic acid derivative having a thiazine ring and filed a patent application (patent application). 59-188744
issue).

Structure and Purpose of the Invention Applicants have conducted extensive research on organic phosphorus compounds, and have developed the formula (
■): F' (wherein R1 and R2 are each a lower alkoxy group,
lower alkynyloxy group, lower alkylthio group or arylthio group, R3 and R4 are each hydrogen or lower alkyl group, R5, R8 and R7 are each hydrogen,
It was discovered that a compound represented by a lower alkyl group, a halogen or a trifluoromethyl group, Y is a methine group or a nitrogen atom, and n is 1 or 2) has an excellent insecticidal effect, and the present invention was completed. .

The compound of formula (I) is a compound represented by formula (■); (In the formula, R1 and R2 each have the same meaning as defined above, and Z represents a leaving group.) It can be produced by reacting with a compound represented by the following formula.

The compound obtained by the above reaction has the formula (I) in the crystalline state.
It takes an imino type structure (hereinafter referred to as A type) shown by , but in solution it rearranges to an amino type structure (hereinafter referred to as B type) and exists as an equilibrium mixture of A type and B type compounds. do. That is, in solution, the compound according to the present invention is represented as the following equilibrium mixture.

(wherein RI SR2, R3, R', R5, YSm and n follow the above definitions) The compound of formula (I) may be of type A, type B or a mixture of types A and B. It also has an effective insecticidal effect.

Therefore, the present invention provides the formula (
This includes compounds of I). In the following description, for convenience, compounds of type A (i.e., imino) are mainly described, but unless it is clear from the context, this is always to be interpreted as meaning only pure type A compounds. Shouldn't.

Next, the terms used in this specification will be defined.

In the description above and below, the term "lower" is intended, unless otherwise specified, to refer to groups having up to 6 carbon atoms, especially groups having up to 5 carbon atoms.

"Lower alkyl group" refers to a straight-chain or branched saturated hydrocarbon residue, especially groups having 1 to 5 carbon atoms. Examples of suitable lower alkyl groups are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tertiary-butyl, pentyl, isopentyl, tertiary-pentyl, neopentyl, l-methylbutyl, 1.2-
Dimethylpropyl, hexyl, etc.

"Lower alkoxy group" means a group in which a lower alkyl group as described above is bonded to divalent oxygen.

Examples of suitable lower alkoxy groups are methoxy, ethoxy,
These include propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, etc.

"Lower alkynyloxy group" means a group having at least one triple condensation 8 group between carbon atoms among the above-mentioned lower alkoxy groups having 2 or more carbon atoms. Examples of suitable lower alkynyloxy groups are ethynyloxy, 2-propynyloxy, 3-butynyloxy,
4-pentynyloxy and the like.

"Lower alkylthio group" means a group in which a lower alkyl group as described above is bonded to divalent sulfur.

Examples of suitable lower alkylthio groups are methylthio, ethylthio, propylthio, isopropylthio, butylthio,
Pentylthio, hexylthio, etc.

"Arylthio group" means a group in which an aryl group, preferably a monocyclic aryl group, is bonded to divalent sulfur.

Examples of suitable arylthio groups are phenylthio, tolylthio, xylylthio, and the like.

"Halogen" includes fluorine, chlorine, bromine, and iodine.

"Leaving group" means a group that is easily eliminated by reaction. Examples of suitable leaving groups are acid residues such as chlorine, bromine, iodine and the like.

As mentioned above, compound (I) can be produced by reacting compound (I[) and compound (III). Although this reaction can be carried out without a solvent, it is preferably carried out in a solvent. Examples of solvents include inert solvents, such as aliphatic hydrocarbons such as n-hexane and cyclohexane, aromatic hydrocarbons such as benzene, toluene, and xylene;
Ketones such as acetone and methyl isobutyl ketone, ethers such as ethyl ether, tetrahydrofuran and dioxane, and halogenated hydrocarbons such as dichloromethane and chlorobenzene are used. This reaction also occurs at the acid receptor (
It is preferable to carry out the reaction in the presence of a base). As acid acceptors, aliphatic tertiary amines such as trimethylamine, triethylamine, and tributylamine, aromatic amines such as dimethylaniline and diethylaniline, heterocyclic amines such as pyridine, α-picoline, and γ-picoline, sodium carbonate,
An inorganic base such as potassium carbonate is used. The reaction temperature is 0
The reaction temperature is from 1 to 100°C, preferably from 20 to 80°C, and the reaction time is from 1 to 12 hours, preferably from 2 to 8 hours. The reaction product is isolated and purified by conventional methods such as extraction, recrystallization, column chromatography, etc.

The compound of formula I isolated in this way takes form A when it is in crystalline form, but exists as an equilibrium mixture of forms A and B when it is an oil. The ratio varies depending on conditions such as substituents, type of solvent, temperature, etc., but is usually 1:1.

In the above reaction, if the compound of formula (1) is obtained in a crystalline state, an equilibrium mixture of types A and B can be easily obtained by dissolving this type A compound in a suitable solvent. I can do it. The equilibrium ratio between these two types varies depending on conditions such as the substituent, type of solvent, temperature, etc., but under normal usage conditions, it is 1:1.

Starting material (II) is produced, for example, according to the reaction formula below.

↓ (IL) (wherein R3, R4, R5, R8, R7, Y and n are as defined above).

In the above reaction formula, from compound (E) to compound (F)
The process of obtaining is described, for example, in the Journal on Organic Chemistry (J, Org, Chem, ) 2
It is carried out according to the method described in Vol. 9, p. 3098 (1964). Next, the reaction between compound (F) and compound (G) is carried out without using a solvent or using a solvent such as ether or benzene in a solvent at a temperature of 0 to 60°C. This is done by stirring for a minute.

The conversion of compound (■()) to compound (II) is carried out, for example, by refluxing for 1 to 3 hours in the presence of an acid such as hydrochloric acid.

Masukuri Compound (I) has excellent insecticidal power against plant pests belonging to insects such as plant parasitic nematodes, Acarina, Orthoptera, Hemiptera, Lepidoptera, Diptera, and Coleoptera. has.

When compound (I) is used as an insecticide, it may be used as it is, or it may be mixed with an appropriate solid or liquid carrier and auxiliary agent depending on the usage situation, such as powder, etc. It is preferable to formulate and use it in the form of granules, wettable powders, emulsions, suspensions, aerosols, flowables, etc.

The above formulation can be manufactured according to conventional methods. Solid carriers that can be used include vegetable powders (e.g. corn, soybean, wheat, wood), mineral powders (e.g. clay, bentonite, acid clay, vermiculite, talc, diatomaceous earth, pumice, activated carbon), synthetic resins ( Examples include vinyl chloride, polystyrene), etc. Liquid carriers include hydrocarbons (e.g. kerosene, solvent naphtha, toluene, xylene), alcohols (methanol, ethanol, ethylene glycol, polypropylene glycol), ethers (e.g. dioxane, cellosolve),
Ketones (e.g. methyl isobutyl ketone, cyclohexanone), halogenated hydrocarbons (e.g. dichloroethane, trichloroethane), esters (e.g. dioctyl phthalate), amides (e.g. dimethylformamide), nitriles (e.g. acetonitrile), fats and oils, and water. is included.

Formulation auxiliaries include surfactants, wetting agents, fixing agents,
Shino, which acts as a thickener, stabilizer, etc., is used. Examples of these are anionic surfactants such as alkyl sulfonates, lignin sulfonates, alkyl sulfates, alkyl polyoxyethylene ethers, sorbitan esters,
Nonionic surfactants such as polyoxyethylene fatty acid ester and sucrose ester, casein, gelatin, CMC1
These include water-soluble polymers such as PVA, gum arabic, and alginic acid.

These preparations suitably contain Compound (I) as an active ingredient in an amount of about 1 to 70%, preferably about 3 to 50%.

Additionally, the formulation can also contain other insecticides, fungicides, herbicides, soil conditioners, fertilizers, and the like.

The application amount varies depending on the application method, timing, location, target pest or animal, and type of crop, but is usually 1-500 g per 10 are.

Next, this invention will be explained in more detail by Examples and Formulation Examples, and the effects of this invention will be clarified by Experimental Examples.

In addition, the abbreviations used in the following examples have the following meanings.

Me: Methyl Et: Ethyl Pr: Propyl Bu Nibutyl Pe: Pentyl Ph: Phenyl DMF Nidimethylformamide Example 1 2-(2,4-dichlorobenzylimino)-5,5=dimethyl-3,4,5,6- Tetrahydro-2H-1,3
-Thiazine-3-thiolphosponate 〇-methyl, S
-1so-butyl ester (Aυ and 0-methyl-S
-1so-butyl-N-2'.

4°-dichlorobenzyl-N-, ((5,5-dimethyl-5,6-cyhydro-4H-1,3-thiazine)-2-
Il2phosphoramidothioate (B1) 2-(2", 4"-dichlorobenzyl)amino-5,5-dimethyl-5,6-dihyde a-4H-1 in a synthesis flask with a stirrer
, 3-thiazine 1.009 (3,30mM), triethylamine 0.379C3,67+nM), toluene 10
Add chu to each portion and heat at 20 to 30℃ while stirring.
-Methyl 5-iso-butylthiophosphoric acid chloride 0.6
79 (3.30mM) was added dropwise, and the reaction was continued at 25-30°C for 4 hours after the dropwise addition. After filtering off the produced triethylamine hydrochloride, toluene was distilled off under reduced pressure to obtain 1.58 g of a pale yellow viscous oil. This was subjected to silica gel column chromatography (Wakogel C-300, developing solvent: n-
Purify with hexane/acetone (10/1 v/v) to collect both fractions containing the target substance, and evaporate the solvent under reduced pressure to obtain a colorless and transparent viscous oil. This was crystallized in a cold place to obtain 1.07 g of white crystals (yield 69.1%) of the title compound A in imino form with a melting point of 73.5-74.5°C.

get. Dissolve this compound A in chloroporm etc.,
By making it into a solution, it can be converted to the amino form of B.

Elemental analysis (C+aHt7NtOtSyP(J!t)CH
NP Calculated value (%): 46.0B 5.80 5.97
6.60 Actual value (%): 46.02 5.74 6.
02 6.32The equilibrium ratio of the equilibrium mixture of A and E determined by NMR tracking is A+:B+ after 29 hours.
=3:2.

NMR (CD cQs) δppm.

A direct: 0.96 (6H, d, J: 60Hz, 1soBu CH
3) 1.13 (6H, dj: 2.OHz thiazine ring CH
s ) 1.58-1.98 (I H, m, 1soBu-
CH< )2.58-2.98 (2H, m, 1soB
uCHt-< )2.68 (2H,s, Thiazine 08
position (7) CH*) 3.38 (2H, dd, J near, 0H
z, 2.0Hz, thiazine 04-position CH,) 3.67 (3H, d, J: I 3 , OH2, po
CHs)4.43 (2H,s, benzyl position CH,)7
．． 05 (I H, dd, J: 8.OHz, 1.5Hz,
2.4=dichlorophenyl 05-position H) 7.18CIH, d, J: 1.5Hz, 2.4-dichlorophenyl 03-position H) 7.50 (lH, d, J: 8.OHz, 2.4- Dichlorophenyl 08-position H) B,: 0.96 (6H,s, thiazine ring CH3) 0, 98
(6H, d, J:6, OHz, 1soBuCH,
) 1.58 to 1.98 (I H, n+, 1soBu
-CH< )2.58~2.98 (2H, m, 1so
BuCHt-
4th place CH,) 3.69 (3H, d, J: 13.OHz
, P-OCH3) 4.81 (2H, d, J: 11.OH
z, benzylic position CH,) 7.1 (1-7,60 (3H, m, 2, 4-dichlorophenyl H) * Regarding the NMR data of B, the portion excluding the AI signal was assigned.

A is characterized by CH at position 04 of the thiazine ring.

and gemcH3 at position C6 becomes d, d, and d due to long-range coupling with p.

A characteristic of B is that CH, at the benzylic position, becomes d due to long-range coupling with p.

Example 2 2-benzylimino-5,5-dimethyl-3,4°5.
6-tetrahydro-2H-1,3-thiazine-3-thiol phosphonic acid O-methyl, 5-sec-butyl ester (A2) and O-methyl 5-sec-butyl N-benzyl-N
-[(5,5-dimethyl-5,6-sihydro 4H-1
,3-thiazin)-2-yl]phosporamide thioate (2-benzylamino-5,5-
Dimethyl-5,6-cyhydro48-1°3-thiazine 6.00g (25.6mM), triethylamine 2.8
Add 5g (28.2mM) and toluene 5011 (2), and add 0-methyl S-5ec-butylthiophosphoric acid chloride 6.299 (25°6mM) dropwise between 10 and 20°C. After the dropwise addition, 30 to 35°C. After reacting for 5 hours at
Get 9. The residue was purified by column chromatography (silica gel; Fuco-gel C-300 developing solvent n-hexane/acetone 1.
The fractions containing the target compound were collected and the solvent was concentrated under reduced pressure to obtain a colorless and transparent nDI.
Equilibrium mixtures 6, 19 (
Yield: 59.5%).

Elemental analysis (CIs Ht e N x Ot P S
x) CHN P Calculated value (%): 53.9g 7.30 6.99
7.73 Actual value (%): 53.04 7,25
6.9. 7.78 bar' Examples 3 to 40 According to the methods of Examples 1 and 2, various 2-amino-1
, 3-thiazine derivative and an appropriate thiophosphoric acid chloride derivative, an organic phosphorus compound having a desired thiazine ring was produced.

The compounds obtained in the above examples were imino-type (
A) and the amino form (B) exist as an equilibrium mixture. For some compounds, chemical shifts that serve as indicators of NMR (CDc (b)) and their respective equilibrium ratios were determined. Attribution is based on the results of crystal analysis of the compound in Example 1 and NMR (CDc (b)).
C123X benzyl only).

Table I below summarizes the compounds obtained in each example, their characteristic values, and the results of NMR measurements.

* a: R', when R'=Me, chemical shift b of R
: When R'=OMe, chemical shift of R1 c: n=1
When , the chemical shift of CH,※※ The NMR measurement results of the compound of Example 39 are as follows.

NMR (CD C123): 0.99 (3H, t, J=7.OH2,) 1.3-2.
2 (4H', m,) 2.9-3.1li (9H, m,) 7.0-7.8 (3H, m,) 8.55 (I H, d, J=5.0Hz,) Equilibrium ratio of the compound: (A):(B)=2:3 Production examples are given below to show the method for producing the starting material (n) in the production of the compound of the present invention.

Production Example 1 2-(2-pyridylethyl)amino-5,5-dimethyl-Δ'-1,3-thiazine 2-pyridylethylisothiocyanate 6.79 (0,
4.29 (0,041 mol) of 2,2-dimethyl-3-aminopropanol was added to the mixture and heated for 30 minutes. Then, add 15 inches of 12NHCQ and reflux for 3 hours. After cooling, the mixture is made alkaline with 4N NaOH, extracted with chloroform, dried over Na and SO4, and the solvent is distilled off. The residue was recrystallized from n-hexane to give the title compound 9.
．． 49 is obtained as pale yellow needle-like crystals. Yield = 92%,
mp = 89-91.5°C.

Production Example 2 Obtained in the same manner as Production Example I except that 2-(2-pyridylethyl)amino-Δ”-1,3-thiazine HCl2 was added and refluxed for 1 hour. Yield 50%, mp= 57~59°
c.

↓ (II) Production examples 3 to 13 The following starting materials were obtained in the same manner as in Production Example 1.

The melting point, yield, and elemental analysis values of each compound are shown in Table 3.

In the table, in the description of elemental analysis values, C is the calculated value (%),
``represents the actual measured value (%).

Examples of formulations of insecticides of the present invention containing compounds obtained according to Examples as active ingredients are shown below.

Formulation example 1 (parts by weight) Active ingredient (compound obtained in Example 1) 2 Clay
88 talc
IO Mix the above ingredients to make a powder.

Production Example 2 (Parts by weight) Active ingredient (compound obtained in Example 3) 30 diatomaceous earth
45 white carbon
20 Sodium lauryl sulfate
3 Sodium lignin sulfonate
2 Mix the above ingredients to make a hydrating agent.

Production example 3 (parts by weight) Active ingredient 20 xylene
60 Polyoxyethylene phenylphenol polymer emulsifier 20 The above ingredients are mixed to form an emulsion.

The insecticidal action of the compounds of the present invention was tested by the method shown in the following experimental examples.

Experimental Example 1 [Test solution preparation method] Dissolve a small amount of compound (I) in DMF and add Tween (T
Distilled water containing 5een) 20 at a concentration of 100 ppm is added to obtain a predetermined concentration.

[Test method] A. Spodoptera larvaecidal test Cabbage leaf pieces measuring 5×5 cm were immersed in the test solution and then air-dried.

Place 2 of these in a 9cm diameter beetle dish and 1 2nd instar larva.
0 insects were released and kept at 25°C, and the killing rate was determined after 48 hours.

B. Diamondback moth larvicidal test Cabbage leaf pieces measuring 5×5 cm were immersed in the test solution and then air-dried.

This was placed one by one in a Petri dish with a diameter of 9 cm, 10 3rd instar larvae were released and kept at 25°C, and the killing rate was determined after 48 hours.

C. Larvicidal test for Kokakumon hamaki Tea leaves (all British) were immersed in the test solution and then air-dried. Three of these were placed in polyethylene cups each having a diameter of 6 cyt and a depth of 4 cm, and 10 4th instar larvae were released, kept at 25° C., and the killing rate was determined after 48 hours.

D. Leafhopper adult test (susceptibility) 1.5-2
Bundle 6 to 7 leaf-aged rice seedlings, wrap the roots with a sponge, and add a small amount of water to a diameter of 6 ax.

Fixed in a 4ca+ deep polyethylene cup. This was placed in a rotary spray tower, and the test solution 2xQ was sprayed onto the stems and leaves, followed by air drying. Next, the treatment cylinder was covered with a transparent plastic cylinder, 100 female adults were released and kept at 25°C, and the killing rate was determined after 48 hours.

1. J. Momoaca bramun larvicidal (nymphicidal) test (
Susceptibility and Resistance) 0.3% in a polyethylene cup 6 cm diameter and 4 cm deep
It was filled with agar gel, and a 3x3 cm Chinese cabbage leaf piece was placed on top of it. One unreported adult was released on a Chinese cabbage leaf,
The pups were kept at 25°C for 24 hours to give birth.

After removing the adults, two test solutions were sprayed onto the leaves under a rotary spray tower. After the treatment, the insecticide rate was determined after 48 hours at 25°C.

K5 false red spider mite adult insecticidal test, N, red spider mite adult insecticidal test 0.3% in a polyethylene cup with a diameter of 6 cm and a depth of 4 cu
It was filled with agar gel, and a kidney bean leaf piece with a diameter of 2 cm was placed on top of the agar gel. Twelve adult female insects were released onto a leaf of common bean, kept at 25°C for 24 hours, dead insects and weakened insects were removed, and 2 mQ of the test solution was sprayed onto the leaf under a rotary spray tower. After the treatment, the insecticide rate was determined after 48 hours at 25°C.

L, false spider mite larvicidal test, 0. Larvicidal test for two-spotted spider mites 0.3% in a polyethylene cup with a diameter of 6 cm and a depth of 4 cx
It was filled with agar gel, and a kidney bean leaf piece with a diameter of 2 cm was placed on top of the agar gel. Seven adult female insects were released onto a leaf of common bean and kept at 25°C for 24 hours to allow them to lay eggs. After removing the adult insects, 2 m (l) of the test solution was sprayed on the leaf pieces under a rotary spray tower. After treatment, the temperature was kept at 2° 5°C, and the number of dead insects was determined based on the number of dead insects after 7 days. The rate was calculated.

M, ovicidal test for false red spider mites, P, ovicidal test for red spider mites, treated in the same manner as in case 0, and kept at 25°C after treatment to determine the number of dead eggs that did not turn into towns after 7 days, that is, the number of dead eggs and the ovicidal rate. I asked for it.

Q. Nijuya Hoshi ladybug adult insecticidal test 6×6CI eggplant leaf pieces were immersed in the test solution and then air-dried. Diameter 9
Cx was placed in a Petri dish, five adult insects were released per leaf, and the insecticidal rate was determined after 48 hours at 25°C.

R, American cockroach larva killing test After immersing a filter paper placed in a petri dish with a diameter of 9G on the shoulder in the test solution, 5 larvae of 1 to 7 white eyes were released into the petri dish after blinking, and kept at 25°C. The insect killing rate after the time was determined.

S, adzuki bean weevil adult killing test lid and bottom covered with stainless steel mesh, diameter 1. ．． Adults within 24 hours of emergence were placed in a screw tube with a height of 8 cm and a height of 5 cm. The screw tube was submerged in the test liquid, and the insect bodies were immersed in the test liquid, air-dried, kept at 25°C, and the insecticidal rate was determined after 48 hours.

The above test results regarding the compounds obtained according to the present invention are shown in Table 1.

(Note) A is Spodoptera aphid (larvae) B is diamondback moth (larva) C is Coccinoid leafhopper (larva) D is leafhopper (adult) ■ is green peach aphid (susceptible nymph) J is green peach aphid (resistant nymph) K is green peach aphid (susceptible nymph) False spider mite (adult) L: False red spider mite (larva) M: False spider mite (egg) N: False spider mite (adult) 0: False spider mite (larva) P: False spider mite (egg) Q: Black spider mite R: American cockroach (larva) S is the insecticidal effect against the adzuki bean weevil (adult), and the number indicates the mortality rate (%).

Experimental example 2 The nematicidal effect of the compounds of the present invention was investigated by the following method.

Method: Fill a plastic pot with sweet potato knot nematode contaminated soil (sandy loam soil, nematode density: 3000 heads/kq soil), and apply a predetermined amount of a chemical solution (dissolved in a small amount of DMF, Tween 20) on the soil surface. (diluted with distilled water). After being allowed to stand for 24 hours, the soil is thoroughly stirred and sown with sagebrush as an indicator plant for line control activity.

After cultivating Hosenjiki in a glass room for one month, the roots of Hosenjitsu are washed and given a score in the following five stages depending on the degree of root nodules formed on the roots due to the parasitism of Nematode nematode, and a goal index is calculated using the following formula. The control effect is determined based on the magnitude of the value.

0: No root nodule epiphyte observed.

l : Root nodule growth is 25% or less of the entire root 2 Root nodule growth is 50% or less of the entire root 3 : Root nodule growth is 75% or less of the entire root 4 : Root nodule growth is 75% of the entire root The results of the above tests regarding several compounds of the present invention are as follows:
Shown in Table ■.

From the above results, the compound of this invention can be used to treat various plant pests.
In particular, it was found to have an excellent insecticidal effect against black spider mites, peach aphids, and nematodes.

Patent applicant Shionogi & Co., Ltd. 1 other attorney Patent attorney Aobai Ao 1 other attorney Q/'1

Claims (1)

[Claims] 1. Formula (I): ▲Mathematical formula, chemical formula, table, etc.▼(I) (In the formula, R^1 and R^2 are a lower alkoxy group, a lower alkynyloxy group, a lower alkylthio group, respectively) group or arylthio group, R^3 and R^4 are each hydrogen or lower alkyl group, R^5, R^6 and R^7 are each hydrogen, lower alkyl group, halogen or trifluoromethyl group, Y is methine group or nitrogen atom, n is 1
or 2). 2. Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1 and R^2 are lower alkoxy group, lower alkynyloxy group, lower alkylthio group, or arylthio group, R ^3 and R^4 are each hydrogen or lower alkyl group, R^5, R^6 and R^7 are each hydrogen, lower alkyl group, halogen or trifluoromethyl group, Y is methine group or nitrogen atom, n is 1
or 2) as an active ingredient. 3. Formula (II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the formula, R^3 and R^4 are hydrogen or lower alkyl groups, respectively, R^5, R^6 and R^7 are hydrogen, lower alkyl group, halogen or trifluoromethyl group, Y is a methine group or nitrogen atom, and n is 1 or 2, respectively). ▼ (III) (In the formula, R^1 and R^2 are each a lower alkoxy group, a lower alkynyloxy group, a lower alkylthio group, or an arylthio group, and Z represents a leaving group). Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R^1, R^2, R^3, R^4, R^5, R
^6, R^7, Y and n have the same meanings as defined above) A method for producing a compound represented by: