JPS59137435A - 2-fluoroethoxy group-substituted benzyl ether, thioether, their preparation and acaricide and insecticide - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (X is O, S; R<1>, R<2> are H, halogen, lower alkyl, lower alkoxy, lower haloalkoxy, lower haloalkylthio, methylenedioxy; R<3>, R<4> are H, methyl). EXAMPLE:3-(2-Fluoroethoxy)benzyl benzyl ether. USE:Acaricide and insecticide: it is effective against various kinds of phytoparasitic acari such as Tetranychus urticae or Panonychus citri to kill them even at their egg and larva stages, whether they are sensitive or resistant to chemicals. Further it is effective against harmful Lepidoptera such as Spodoptera litura FABRICUS and Hemiptera such as Laodelphax striatellus. PREPARATION:The reaction of a compound of formula II [when one of Y and Z is halogen, the other is X-M (M is H, alkali or alkaline earth metal)] with another compound of formula III gives the compound of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel compound 2-fluoroethoxy group jf
5f, a converted benzyl ether compound and a thioether compound, a method for producing the same, and an acaricide/insecticide containing these compounds as active ingredients.

Specifically, general formula (1) (in the formula, or an oxygen atom or a sulfur atom is Hl, R2
represents a hydrogen atom, a rogen atom, a lower alkyl group, a lower alkoxy group, a lower alkoxy group, a lower alkylthio group, or a methylenedioxy group, R3 and R
4 represents a hydrogen atom or a methyl group)
The present invention relates to benzyl ether compounds and thioether compounds substituted with -fluoroethoxy groups, methods for producing the same, and acaricides and insecticides containing these compounds as active ingredients.

Various compounds are used to control mites, including organochlorine compounds and organophosphorus compounds, but in recent years,
Mites with reduced susceptibility to these drugs have appeared, making it difficult to control these mites with existing drugs. Therefore, a new type of acaricide different from conventional acaricides is desired.

The present inventors have conducted intensive research with the aim of providing an economical and highly safe acaricide, and have developed a new type of acaricide, which is different from conventional acaricides, and is expressed by the general formula (1). The present invention was completed based on the discovery that the compound has excellent acaricidal activity.

The compounds of the present invention are effective against various plant-parasitic spider mites, such as the two-spotted spider mite, the red-spotted spider mite, and the citrus spider mite.

In particular, it exhibits poor ovicidal and larvae-killing powers in the egg and nymph stages of various desk mites, and is effective in controlling sensitive and resistant mites, which are harmful birds. However, the compound of the present invention not only has an acaricidal effect, but also exhibits effective insecticidal power against Lepidoptera pests such as Spodoptera nigra and Hemiptera pests such as the common planthopper.

The compound of unexploded IJ1 (2-
This compound is a new fluoroethoxy group-substituted benzyl ether blocking conductor and dioether blocking conductor.

Otsu-(2-fluoroethoxy)penzylbenzyl ether which is an example of the compound of the present invention 6-(2-fluoroethoxy)benzyl-4-methylbenzyl ether
d'c h so;)t (general formula 1), R1
, R2, R3 and R4 are all hydrogen atoms, X is an oxygen atom, and the substitution position of the 2'-fluoroethoxy group is 6.
- position) (In general formula (1), R1 is a methyl group, R2, R3 and R4 are all hydrogen atoms, χ is an enzyme atom, and the substitution position of the 2-fluoroethoxy group is 4-
The structural formula is

Specific examples of the compounds of the present invention include R1 in general formula (1).
When the type and substitution position of R2, the type of R3, R' and X, and the substitution position of the 2-fluoroethoxy group are shown, the compounds shown in Table 1 can be obtained.

However, in the general formula (+), when R3 and R4 are methyl groups, optically active forms with asymmetric carbon exist, but these optical isomers and mixtures of these components are included. .

The production method of the present invention comprises a compound represented by the general formula (11) and a compound R' represented by the general formula (ill) [in the general formula (1) and (II), R'1. R2
(d, /i (elementary atom, halogen atom, lower alkyl group,
Lower alkokino group, lower haloalkoxy group, lower haloalkylthio group, or (/i methylene 7oxy group, R'',
R' represents a hydrogen atom or a methyl group, Y and Z (d one of which represents a halogen atom, and the other represents a
where X represents an acid atom or a sulfur atom, and M represents a hydrogen atom or an alkali metal or alkaline earth metal atom.

The raw materials used in the method of the present invention are the compound represented by the general formula (IT) and the compound represented by the general formula (Ill).

Among these, the general compound represented by the general formula (ill) can be produced, for example, from hydroxy/benzaldehyde or hydroxybent r'j t'& ester and 1-chloro-2-fluoroef/ by the following production route. Can be manufactured.

(Y represents a cogen atom, and R5 represents an alkyl group) In the production method of the present invention, a compound of the general formula (0) or (Ill) is used as a raw material compound such as an alcohol, a thiol, or a thiol ( In general formulas (11) and (II), where either Y or Z is X-M, M is a hydrogen atom), or alcohola-1-s (general formulas (U) and )
So, Y.

Where either one of Z is XM, the embodiments differ somewhat depending on whether M is an alkali metal or alkaline earth metal atom.

That is, when a halide is reacted with an alcohol or thiol in which M is a hydrogen atom, the reaction is carried out in the presence of a base as a deoxidizing agent in an appropriate solvent at room temperature or under heating to form the desired compound of general formula (1). A 2-fluoroethoxy group-substituted pencil ether derivative or thioether derivative is obtained. The bases mentioned here include oxides, hydroxides, and carbonates of alkali metals or alkaline earth metals, and amines such as 1-IJ ethyl acetate, such as potassium carbonate, barium oxide, and sodium hydroxide. You can open things like 8
As a medium, water, aromatic hydrocarbons such as benozene and toluene, aliphatic hydrocarbons such as hexane and heptane, etc.
Halogenated hydrocarbons such as chloroform and dichloromethane; non-proton-donating polar solvents such as dimethylformamide and methyl sulfoxide; Nitrile etc. can be used. Further, as a catalyst, a phase transfer catalyst, typified by tetra-n-butylammonium bromide, triethyl-7-fluorammonium chloride, etc., is used.

In the case of reacting alcoholades, which are alkali metal or alkaline earth metal atoms, with halides, the reaction is carried out in a solvent at room temperature or under heating.

As the solvent, any of the above-mentioned @mediums except water can be used.

The acaricidal insecticide of the present invention contains the compound represented by the general formula (II) as an active ingredient.

When the compound represented by general formula (1) is actually used for the purpose of acaricidal and insecticidal purposes, it can be used in the form of sheep flavor without adding any other ingredients, but a carrier may be added to make it easier to use as a control agent. It is common practice to mix them together to make a preparation, dilute it as necessary, and apply it. For formulation, it can be made into any dosage form such as emulsions, wettable powders, powders, granules, oils, aerosols, etc. by methods familiar to those skilled in the art, similar to general agricultural chemicals, which do not require any special conditions. They can be prepared and used for various purposes depending on the purpose.

In the acaricidal insecticide of the present invention, the compound represented by the general formula <1)-C has a weight ratio of 0.001 to 95, preferably 0.
01 to 50 weight ratio.

Furthermore, the acaricidal insecticide of the present invention (also includes other physiologically active substances, such as phosphorus-based insecticides, carnocomate-based insecticides,
By mixing with pyrethroid insecticides, other insecticides, acaricides, fungicides, nematicides, herbicides, and other agricultural chemicals, a multipurpose composition J with excellent efficacy can be obtained (
You can also do 2 and 2, and you can expect a great mutual effect.

Example J: , Hikudafuention (0,0-7ethyl 2
゜3-dihydro-6-oxo-2-phenyl-6-pyridazinyl phosphorothioate), /chlorovos(0-(
2,2-dichlorovinyl)0. O-dimethyl phosphate), fenitrothion (o, o-7notyl o-(
3-) thyl-4-nitrophenyl) phospho-1 cothiony-1-), dianonone (○,○-diethyl○-(2-isopropyl-6-, If-4-biriminonyl) phosphorothionate), cyanophos (o -(4-cyanophenyl)o,o-dimethylphospho-1i-thioate), fuentoate (s-(α-coni)-gisicarponylbenzyl)○,○-tumethylbosphoro-7-thioate), salithion (2-methoxyno-4H-1, ro, 2-benzodioxaphosphorine-2-sulfisodo), /anofenphos (o-t(4-cyanphenyl)〇-ethylphenylphosphonothioate), fenthion (0,0-dimethylo-(3-methyl- 4-methylthiophenyl)phosphorothioate), chlorpyrifos (0- (3,5,
6-)-Lichloro-2-pyridyl)O1○-ethyl phosphorothioate), dimethoate (0,0-methyl s-' (N-methylcarbamoylmethyl) phosphorodithioate), malathion (S-(1,2-bis (Ethoxycarbonyl)ethyl]0.0-diethylphosphorodithioate), acephate (○, S-dimethyl N-
acetylphosphorabadothioate), dialiphos (S
= (2-chloro-1-phthalimidoethyl)O20-diethyl phosphorodithioate), etc. (phosphorus-based insecticides,
Carbaryl (1-naphthyl N-methylcarbamate),
Mpt, ac
Carbamates such as (3,4-xylyl N-methylcarbamate) glopogy/nia (2-isopropoxyphenyl N-methylcarbamate), aldicarb (2-methyl-2-methylthiopropionaldehyde O-methyl-rubamoyloxime), etc. insecticide, allethrin (d
, t-(3-methyl-2-methyl-2-cyclopenten-4-on-1-yl)chrysanthemate), tetramethrine (N-(3,4,5,6-tetrahydrophthalimide)-methylchrysanthemate) mate), resmethrin (
5-Benzyl-ro-furylmethyl-d, 7-cis.

1r21nS-chrysansemate), phenothrin (3
-phenoxybenzyl d, J4-cis, t
rans-Krizanseme-1-), Furanosuwan ((5
-Glopalkil) Furfurir d,! knee cis, t
rans-chrysano-1・), hermesrin (3-
phenoxybendi/l/(1,l-cis,
trans-6-(2,2-dichlorovinyl)-2,2
-dimethylcyclopropanecarboxylate), Zypermethrin (α-cyano-6-noenoxybe7sil d
, f-cis, trans-3-(2,2
-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate), tetramethrin (α-cyano-
6-phenoxybenzyl d, A-cis-3-(2,2
-dibromovinyl) -2,2-dimethylcyclopropanecarboxylate), fenvaleret-1---(α-
Cyano-6-fethoxyben/alpha-ingrovir
2.3
．． Pyrethroid insecticides such as 3-tetramethyl (cyclopropanecarboxylate), tetradifone (4-chlorophenyl-2', <5'-)') chlorophenylsulfone), kelsene (1,1-his (4-I')
(rolophenyl)-2,2,2-)lichloroethanol)
, amitraz(N'-(4-chloro-2-tolyl)-N
, N--7 methylformamicin), Chlorbensyle 1.(Ether 4,4'-dichlorobenzilate), BC
PE (1,1-bis(4-'70 phenyl)ethanol), heso, l-1-(ethyl 0-benzoylro-chloro-2゜6-simethoxybenzohydroxyminate)
, chlorzenamidine (N'-(4-chloro-2-)
It is possible to use the compound of the present invention in combination with acaricides such as IJru) -N,N-dimethylformamidine). Furthermore, benozoyl urea compounds such as cyclubenzuron (1-(4-10 lophenyl)-3-(2,,6-cyfluorobenzoyl)urea) can also be used in combination. Although it is highly stable against oxidation, antioxidants or ultraviolet absorbers such as BIT (2,6-sheet tcrt-butyl-p) may be added as necessary.
-cresol), BHA (2-1ert-butyl-4-
Methoxyphenol and 6-1er 1-butyl-4
- Phenol derivatives such as (mixtures of metquinphenol), bisphenol derivatives, and arylamines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, butylene of phenetidine and acetone, and Compounds suitable as stabilizers:
By adding ::, a composition with stable effects can be obtained.

Hereinafter, the present invention will be deceptively explained by Examples, Test Examples, and Reference Examples.

In addition, comparative compounds (a) to (g) shown below were used as control compounds in test examples showing the effects of the acaricide insecticide of the present invention.

(a) DDVP(0,O-dimethyl-〇-(2,2-
dichlorovinyl)-phosphate) (1)) Dia77(0,○-diethyl-(2-
inopropyl-6-methyl-4-pyrimidyl) phospho 1
Cothioate) (C) Zocofor (1,1-bis(4-chlorophenyl)
-2,2,2-1-lichloroethanol) (d) Chlorophenamine (N' -(4-chloro-2-tolyl)
-N, N-7 methylformamidine) (e) amitraz(ro-methyl-1,5-bis(2,4-xylyl)-
1,ro-5-triazophth-1,4-diene) (f) Butohon (4-chlorophenyl-2,4,5
-Trichlorophenylsulfone) Reference (Y1J1 (Synthesis of raw material 4-(2-fluoroethquin)pensyl chloride) DMFIDDiπg was reacted with 4-hydroxypenzaldehye for a period of time. After the reaction was completed, it was cooled to room temperature and water was added. The toluene layer was extracted with gold water, dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure to obtain crude 4-(2-fluoroethoxy)benzaldehyde 5562.

Next, in 140 + 111 ethanol, 656 ml of the crude 4-(2-fluoroethoxy)benzaldehyde obtained in
7 was dissolved, and thorium borohydride 1107 was carefully added thereto at 47-50°C. Boron hydride. After the reaction was completed, the mixture was cooled to room temperature, water was added, and extraction was performed with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. The toluene was distilled off under reduced pressure to give 32,4F-4-
(2-fluoroethquine) benzyl alcohol (….
1), 37.5-680°C) were obtained.

Next, this crystal was dissolved in 100++ Lg of benzene, and thionyl chloride 2617 was added thereto at 40°C or lower. After further reacting at room temperature for 2 hours, the mixture was poured into water and extracted with l.rueh/. The toluene layer was washed with a cooled saturated hydrocarbon sodium aqueous solution, washed with water, dried over anhydrous sodium sulfate, and distilled off with toluene under reduced pressure to obtain oily 612.
4-(2-fluoroethoxy)pensyl chloride of No. 7 was obtained.

δGZJ-a 4roa (S, 2H), 3.72
-3.80 (n], IH), 4.011~4
, 08 (m, IH) , 4.23~4.30 (m
, '11 () , 4.7 i ~ 4.78 (m, IH
) , 6.7'5(d, 2[() , 7.1 7 (
d.

2H) Reference Example 2 (Synthesis of 5-(2-fluoroethoxy)be/zyl chloride as a raw material) DMF130 Nyrohydroxybenzoic acid ether ester 02, 1-fluoro-2-chloroethane 1497
, added 3747 anhydrous expanded potassium, J";'l 4"
The reaction was carried out at 120° C. for 4 hours while holding 1′. The reaction mixture was cooled with a room temperature agent, dissolved in water, extracted with toluene, and the toluene layer was washed with water, dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure to obtain crude 6-(2-fluoroethane). Benzoic acid dif 32A? I got it. next,
Dry tetrahydrofuran 200+i/? The previously obtained crude ethyl 6-(2-fluoroethoxy)benzoate 32 was added to a solution of lithium aluminum hydride 607 suspended in
75g! ' was added at 40 to 45°C, and the mixture was further heated under reflux for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and decomposed into ethanol and water to form unreacted lithium aluminum hydride, and the water was removed to give 411 J of toluene. After washing the toluene layer with saturated brine, drying with anhydrous sodium sulfate; chestnut, toluene was removed to obtain crude 3-(2-fulmeroethogish)be/nor alcohol-260f. the law of nature. This JM elementalization is ro-(2-fluoroethokeene)-pencyl chloride. o f wo? ! *.

δ"'a 4.47 (s, 2T(), 5.97~
4.06 (m, IH), 4.22~41 (+n
,IH) ,,467~4.50 (m, IH)
, 4.84-4, 95 (m, IH) , 6.7
1 to 7.26 (m, 4H) Real jJf Hayashi jj/:]i (4-(2-fluoroethoxy)ben/4-chlorobenonelether lft. compound, %9)) 4-(2-
Fluoroethoxylate/) Pencil alcohol 9, L ethylbenzyl ammonium fluoride 05 g, 50 water 1 Sodium chloride aqueous solution 207 50
The mixture was stirred at ℃ for 4 hours. After cooling to room temperature, it was poured into water, extracted with toluene, and the toluene layer was washed with saturated brine. After drying over anhydrous sodium sulfate, the toluene was distilled off under reduced pressure, and the resulting lees ether was purified by column chromatography on silica gel 200 mg (developing solvent: benzene) to obtain the desired product and the ) Pale yellow viscous crystals of benzyl 4-chlorobennor ether.

m, I), 43.0・~43.7°C130
5, 1250, 1180, 1070-1085.

1020. 930.820 δ0014 Ro79~Ro90 (m, 1
H), 4.0'5~4.19 (m, 1
H), 4.26-4.37 (m, I H
), 4.72--4.84 (m, 1
H), 4 Otsu 5 (s, 4B), 6.75
(d, J=9.Q, 2H)7.15 (d,
J=9.0, 2H), 7.19 (S, 4)()
Example 2 (3-(2-Fluoroethoxy)benzyl pencil ether (compound A20)) Dry tetrahydrone run 0+n, 13 was charged with 4 g (60% in oil) of hydrogenated 1~lium O2! (2-fluoroethoxy)benzyl alcohol 1. Off: Added. 3 at 50-60℃
After stirring for 0 minutes, benol chloride 1.7? was added, and the mixture was heated to reflux for 6 hours. After cooling to room temperature, it was poured into water and extracted with toluene. The toluene extract was purified with saturated brine, dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure. The obtained crude ether was mixed with silica gel 5
Column chromatography of 02 (Ju Gi) solvent; toluene), 3-(2-fluoroethquin)benzyl hemp ether 1, 2 g
I got this.

+1ゎ° '1.55 [18 1"11+r12830, 1600, 15B5,
1490, 1450.

1360, 127cl, 1075, 1055
,890δCG,p,, 6.82~3.9
6 (rn, 1H) 4.1 0-~4.2
4 (m, 1H),! 1.26~4.42 (m
, IH) 4.74-4.88 (m, IH)4
．． 42(S, 2H) 4.45(S, 2-i()6
．． 62~7.34 (m, 4H)' 7.23 (S
, 4B) Example 3 (ro-(2-fluoroethoxy)hemfur 4-methylbenzyl ether (compound, +71';, 16) 4
-(2-fluoroethoxy)pencilflora()”t
Of/, 4-methylbenzyl alcohol 065Y, +-
1) Ethyl-hensyl ammonium chloride 1-0.2
Six volumes of 50% NaOH aqueous solution were stirred at 50°C for 6 hours.

After cooling at room temperature, drain into water, extract with benzene, and dissolve to saturation/l [
] Washed with saline. After drying with anhydrous thorium sulfur, the benzene was distilled off under reduced pressure, and the obtained citrus ether was purified by column chromatography on 7-Licagel 507 (developing solvent: benzene) to obtain the target toj, *3-(2- fluoroethoxy)hennol 4-methylhensyl ether 11
I got a g.

n 19” 1.5470 v”” 2830 .1600 .1595 .
1490. 1455.

1270, 1080, 1055 δ0014 226 (S, RoH) 4 Ro5 (S, 2
H) 368~ro80 (m, 1H)' 3.9
6-4.07 (m, IH) 4.15-4.27
(m, I H) 463~4.76 (m, I
H) 6.56 to 7.24 (m, 8 H) Example 4 (4-(2-Fluoroethoxy)henfur 4-methoxyfluor ether (compound &25)) in dry sieved acetonitrile 607-1B Sodium hydride 1/2 liters (60 parts, 1 noil) was clouded, and then 4-nodoxyl alcohol 117 was added.

50~6D'C 0 minutes; 4-(2-
Fluoroethoxy)-bennol chloride 1.5 fP
was added and refluxed for 5 Lj (refluxed for 15 hours). After cooling to room temperature 1, it was poured into water at 1:1 and extracted with benzene. The mixture was dried over anhydrous sodium sulfate, and toluene was distilled off under reduced pressure. The obtained crude ether was mixed with Silica Kel 507.
4-(2-Fluoroethoxy)benzyl 4-nodoxybenzyl ether was obtained using column chromatography (developing solvent: benzene/ethene 9/1).

n""" 1.5580 ν11"" 28B0, 2830.1620, 1
595, 1525.

1460, 1260, 11B5, 1090, 8
95δQJ4. 3.56 (S, RoH)
46F3 (s, 4H) 3.78-3.90 (n],
1 H) 4.05-4.16 (m, I H)
4.24-~4.35 (nl, 1H)
4.70-4.82 (m, 1 H) 652-7.
22 (m, 8H) Example 5 20 parts of Toho Chemical registered trade name) and 60 parts of xyl
Mix in one stroke to form an emulsion.

Example 6 (Manufacture of hydrating powder) Add 5 parts of surfactant to 20 parts of the compound of the present invention, mix well, add 75 parts of diatomaceous earth, and hydrate by stirring and mixing in one person. ;ill.

Example 7 (Manufacture of powder) 6 parts of the compound of the present invention are dissolved in 10 parts of Artone, 97 parts of clay for powder are added, and the acetone is evaporated to obtain a powder.

Example 8 (Manufacture of granules) 5 parts of the compound of the present invention, 2 parts of Celogen 7A (Carphoki dimethyl cellulose, Daiichi Kogyo Seiyaku brand name), Sunextract (sodium lignin sulfonate salt, Yama, Nou Kokushaku pulp product)
2 parts were mixed with 91 parts of fillet, water was added to form 111 parts of the mixture, and the granules were sized to an optimal buff diameter to form granules.

The emulsion obtained in Example 5 was suspended with water to a predetermined concentration (during the night, after thoroughly soaking fresh sweet potato leaves in oil, The leaf agent-treated leaves were air-dried to a diameter of 10 C'I.
? The larvae were transferred to a plastic cup with a size of L11A"<6 cm, and the larvae were fed with 10 larvae each. After 721 bites, the survival or death of the larvae was examined.

Test J.19 was conducted in two consecutive sessions, and the results are shown in Figure 2.

Table 2 Test Example 2 Five to six rice fungi at the 6-leaf stage were tied together and hydroponically cultivated in a pot with a diameter of 5 cnt. was sprayed. After air-drying, the bacteria were placed in a metal cylinder 2 times, and 11 sub-adults of the brown planthopper were placed in a bowl.
0 mice were released and left in a room at 25°C.

48 hours after treatment, the number of live and dead insects was examined to calculate the mortality rate.

The test was carried out in two series, and the results are shown in Table 6. 20 animals each were vaccinated. After 24 hours, the emulsion obtained in Example 5 was diluted with water to a predetermined concentration, and the solution was diluted with water to a predetermined concentration.

15cynz At the dispersion tower with a height of 50tx, the medicine at "Leftisf" 2) At night, it was i, 5 +I + 9 /
In a room at 25°C where it was sprayed so that cya
After leaving it for 8 hours, the number of live and dead insects was investigated to calculate the mortality rate.

Test 1 was conducted in triplicate, and the results are shown in Table 4.

Table 4 Test Example 4 10 to 12 adult female spider mites are placed on a leaf disk similar to that in Test Example 6 and left in a room at 25°C. After 48 hours, the adults were removed and the number of eggs laid was investigated, and then the emulsion obtained in step 5 and diluted with water to a predetermined concentration was sprayed. At this time, there were around 1,100 rabbits that were printed on each leaf disk.

After treatment with medicine 1111, leave it for 7 days to investigate the number of insects that have turned 3.
1 effect was determined.

Trial) The yarn was carried out using Roren 11rl) and the results are shown in Table 5.

Table 5 Test Example 5 Cut 15 square pieces of fresh/infested mandarin leaves into 15 square pieces, place them on damp cotton wool, and place them on wet cotton wool.
Five pups were brought into contact with each other and left for 48 hours to spawn.

After removing the adults, the number of eggs laid was investigated, and then the procedure was carried out according to Example 5;
/ I poured this solution into one bowl. After being kept in a room at 25°C for 7 days, the larvae that had lived on the leaf pieces were investigated, and as in Test Example 4, 3. Chemical 1'' RanjIJ effect was determined.

The test was conducted six times in a row, and the results are shown in Table 6.

Table 6

Claims (1)

[Claims] 1) General formula CI) (wherein, X is an oxygen atom or a sulfur atom, Hl, p
, 2 is a hydrogen atom, a halogen atom, or a lower alkyl group. 2-fluoroethoxy group-substituted benzyl ether compounds and thioether compounds represented by a lower alkoxy group, a lower haloalkoxy group, a lower haloalkylthio group or a methylenedioxy group, and R3 and R' represent a hydrogen atom or a methyl group. 2) Compound represented by general formula (11) and general formula (1)
A method for producing a 2-fluoroethoxy group-substituted benzyl ether compound and a thioether compound represented by the general formula (1), which comprises reacting the compound represented by the formula (1) with the compound represented by the formula (1). R' [In general formulas (1), (II) and (Ill), Hl and R2 are hydrogen atom, halogen atom, lower alkyl group, lower alkoxy; rV, lower...roalkoxy group, lower haloargylthio group or methylenedioxy group, R3 and R4 represent a hydrogen atom or a methyl group, and X represents an oxygen atom or a sulfur atom. Furthermore, one group of Y and Z represents a halogen atom, and the other group represents an X-
M (where X represents an oxygen atom or a sulfur atom, and M represents a hydrogen atom or an alkali metal or alkaline earth metal atom)] B) In general formula (11), Y
3. The manufacturing method according to claim 2, wherein is X-M (X and M have the above meanings), and in the general formula (ill), Z is a halogen atom. 4) In the general formula (+1), Y is a halogen atom, and in the general formula (,111), Z is X-M (X, M represent the above meanings), according to claim 2 Production method. 5) General formula (1) (wherein, Xid oxygen atom, sulfur atom, R1゜R
2 is a hydrogen atom, a rogen atom, a lower alkyl group. A 2-fluoroethoxy group-substituted benzyl ether compound or thioether compound represented by a lower alkoxy group, a lower haloalkoxy group, a lower haloargylthio group, or a methylenedioxy group, and R3 and R4 represent a hydrogen atom or a methyl group is effective. An acaricide insecticide characterized by containing it as an ingredient.